AU663303B2 - Creation of Inventions and Patents with Artificial Intelligence

AU663303B2 – Compositions containing sumatriptan
– Google Patents

AU663303B2 – Compositions containing sumatriptan
– Google Patents
Compositions containing sumatriptan

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Info

Publication number
AU663303B2

AU663303B2
AU13264/92A
AU1326492A
AU663303B2
AU 663303 B2
AU663303 B2
AU 663303B2
AU 13264/92 A
AU13264/92 A
AU 13264/92A
AU 1326492 A
AU1326492 A
AU 1326492A
AU 663303 B2
AU663303 B2
AU 663303B2
Authority
AU
Australia
Prior art keywords
film
international
pharmaceutical composition
document
methyl
Prior art date
1991-03-08
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Ceased

Application number
AU13264/92A
Other versions

AU1326492A
(en

Inventor
John Malcolm Padfield
Anthony John Phillips
Ian Keith Winterborn
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Glaxo Group Ltd

Original Assignee
Glaxo Group Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
1991-03-08
Filing date
1992-03-02
Publication date
1995-10-05

1992-03-02
Application filed by Glaxo Group Ltd
filed
Critical
Glaxo Group Ltd

1992-10-06
Publication of AU1326492A
publication
Critical
patent/AU1326492A/en

1995-10-05
Application granted
granted
Critical

1995-10-05
Publication of AU663303B2
publication
Critical
patent/AU663303B2/en

2012-03-02
Anticipated expiration
legal-status
Critical

Status
Ceased
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

KQKPFRSPSRPDEB-UHFFFAOYSA-N
sumatriptan
Chemical compound

CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1
KQKPFRSPSRPDEB-UHFFFAOYSA-N
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abstract
description
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239000000203
mixture
Substances

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title
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description
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sumatriptan
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description
3

239000004480
active ingredient
Substances

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claims
abstract
description
19

239000008194
pharmaceutical composition
Substances

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claims
abstract
description
19

239000007909
solid dosage form
Substances

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abstract
description
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150000003839
salts
Chemical class

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abstract
description
13

238000011282
treatment
Methods

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abstract
description
10

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Diseases

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migraine
Diseases

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abstract
description
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solvate
Substances

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description
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208000002193
Pain
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abstract
description
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239000007888
film coating
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description
26

238000009501
film coating
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239000003826
tablet
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239000001866
hydroxypropyl methyl cellulose
Substances

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description
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235000010979
hydroxypropyl methyl cellulose
Nutrition

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description
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hydroxypropyl methyl cellulose
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description
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239000000546
pharmaceutical excipient
Substances

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hydroxypropyl methyl cellulose
Chemical compound

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succinate salts
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ethyl group
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Methyl methacrylate
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dependent effect
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dimethylamino group
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water
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Lactose
Natural products

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Titan oxide
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granular material
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final product
Substances

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magnesium stearate
Chemical compound

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Substances

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triacetin
Chemical compound

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Dichloromethane
Chemical compound

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Propylene glycol
Chemical compound

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titanium dioxide
Substances

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CSCPPACGZOOCGX-UHFFFAOYSA-N
Acetone
Chemical compound

CC(C)=O
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Corn starch
Polymers

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Croscarmellose sodium
Polymers

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Ethanol
Chemical compound

CCO
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Iron oxide
Chemical compound

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235000019759
Maize starch
Nutrition

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Polymers

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239000002202
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Substances

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Silicium dioxide
Chemical compound

O=[Si]=O
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DPXJVFZANSGRMM-UHFFFAOYSA-N
acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium
Chemical compound

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description
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239000007891
compressed tablet
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croscarmellose sodium
Drugs

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235000010947
crosslinked sodium carboxy methyl cellulose
Nutrition

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description
2

FLKPEMZONWLCSK-UHFFFAOYSA-N
diethyl phthalate
Chemical compound

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239000007919
dispersible tablet
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dye
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239000012458
free base
Substances

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description
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230000007160
gastrointestinal dysfunction
Effects

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description
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239000001087
glyceryl triacetate
Substances

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235000013773
glyceryl triacetate
Nutrition

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239000000314
lubricant
Substances

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description
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235000019359
magnesium stearate
Nutrition

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235000019813
microcrystalline cellulose
Nutrition

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description
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239000008108
microcrystalline cellulose
Substances

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microcrystalline cellulose
Drugs

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polyethylene glycol
Polymers

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description
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VZCYOOQTPOCHFL-UHFFFAOYSA-N
trans-butenedioic acid
Natural products

OC(=O)C=CC(O)=O
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description
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triacetin
Drugs

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description
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GUBGYTABKSRVRQ-XLOQQCSPSA-N
Alpha-Lactose
Chemical compound

O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O
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Citrate
Chemical compound

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D-Mannitol
Chemical compound

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Dextrotartaric acid
Chemical compound

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Chemical compound

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Fumaric acid
Chemical compound

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Hydrochloric acid
Chemical compound

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Hydrogen bromide
Chemical compound

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Impaired gastric emptying
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Mannitol
Natural products

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Methanesulfonic acid
Chemical compound

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NO3
Inorganic materials

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Nitrate
Chemical compound

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PO4
Inorganic materials

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Sodium laurylsulphate
Chemical compound

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Sucrose
Chemical compound

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Sulfate
Chemical compound

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Vomiting
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WIN1 gene
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acute effect
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alcohols
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aluminium
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aluminium
Chemical compound

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aluminium
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aqueous solution
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benzoic acid
Chemical compound

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calcium hydrogenphosphate
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dicalcium phosphate
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iron(III) oxide
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maleic acid
Chemical compound

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octadecanoic acid
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octadecanoic acid
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phosphate
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polyvinylpyrrolidone
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potato starch
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powder
Substances

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prophylaxis
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sesame oil
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sesame oil
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silicon dioxide
Substances

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sodium laurylsulphate
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sodium starch
Drugs

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stearic acid
Substances

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succinate(2-)
Chemical compound

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sucrose
Substances

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sulphate ion
Inorganic materials

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PORMUFZNYQJOEI-UHFFFAOYSA-N
sumatriptan succinate
Chemical group

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symptom
Diseases

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talc
Substances

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talc
Inorganic materials

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tartrate
Drugs

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therapeutic dose
Methods

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description
1

239000005526
vasoconstrictor agent
Substances

0.000
description
1

239000000080
wetting agent
Substances

0.000
description
1

Classifications

A—HUMAN NECESSITIES

A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE

A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES

A61K9/00—Medicinal preparations characterised by special physical form

A61K9/20—Pills, tablets, discs, rods

A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating

A61K9/2806—Coating materials

A61K9/2833—Organic macromolecular compounds

A61K9/286—Polysaccharides, e.g. gums; Cyclodextrin

A61K9/2866—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose

A—HUMAN NECESSITIES

A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE

A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES

A61K31/00—Medicinal preparations containing organic active ingredients

A61K31/33—Heterocyclic compounds

A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins

A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil

A—HUMAN NECESSITIES

A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE

A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES

A61K31/00—Medicinal preparations containing organic active ingredients

A61K31/33—Heterocyclic compounds

A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins

A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole

A61K31/404—Indoles, e.g. pindolol

A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin

A—HUMAN NECESSITIES

A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE

A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

A61P25/00—Drugs for disorders of the nervous system

A61P25/06—Antimigraine agents

Abstract

A pharmaceutical composition for oral adminstration comprising a film-coated solid dosage form including 3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulphonamide or a pharmaceutically acceptable salt or solvate thereof as active ingredient. The film-coated solid dosage forms are of use in the treatment of conditions associated with cephalic pain, in particular migraine.

Description

s OPI DATE 06/10/92 AOJP DATE 12/11/92
INI
(51) International Patent Classification 5 A61K 31/40, 9/28 APPLN. ID 13264 92 LTION TREATY (PCT) PCT NUMBER PCT/EP92/00460 Al (11) International Publication Number: WO 92/15295 (43) International Publication Date: 17 September 1992 (!7.09.92) (21) International Application Number: (22) International Filing Date: Priority data: 9104890.0 8 March PCT/EP92/00460 2 March 1992 (02.03.92) 1991 (08.03.91) (74)Agents: FILLER, Wendy, Anne et al.; Glaxo Holdings plc, Glaxo House, Berkeley Avenue, Greenford, Middlesex UB6 ONN (GB).
(81) Designated States: AT, AU, BB, BF (OAPI patent), BG, BJ (OAPI patent), BR, CA, CF (OAPI patent), CG (OA- PI patent), CH, CI (OAPI patent), CM (OAPI patent), CS, DE, DK, ES, Fl, GA (OAPI patent), GB, GN (OA- PI patent), HU, JP, KP, KR, LK, LU, MG, ML (OAPI patent), MN, MR (OAPI patent), MW, NL, NO, PL, RO, RU, SD, SE, SN (OAPI patent), TD (OAPI patent), TG (OAPI patent), US.
Published With international search report.
(71) Applicant (for all designated States except US): GLAXO GROUP LIMITED [GB/GB]; Glaxo House, Berkeley Avenue, Greenford, Middlesex UB6 ONN (GB).
(72) Inventors; and Inventors/Applicants (for US only) PADFIELD, John, Malcolm [GB/GB]; Glaxo Manufacturing Services Limited, Stockley Park West, Uxbridge, Middlesex UBII IBU PHILLIPS, Anthony, John [GB/GB]; WIN1 BORN, lan, Keith [GB/GB]; Glaxo Group Research Limited, Park Road, Ware, Hertfordshire SG 12 DG (GB).
663303 (54) Title: COMPOSITIONS CONTAINING SUMATRIPTAN (57) Abstract A pharmaceutical composition for oral administration comprising a film-coated solid dosage form including 3-[2-(dimethylamino)ethyl]-N-methyl- I H-indole-5-methanesulphonamide or a pharmaceutically acceptable salt or solvate thereof as active ingredient. The film-coated solid dosage forms are of use in the treatment of conditions associated with cephalic pain, in particular migraine.
r_ i;- WO 92/15295 PCT/EP92/00460 -1- Compositions containing Sumatriptan The present invention relates to a pharmaceutical composition containing as active ingredient 3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5methanesulphonamide, in particular a composition for oral administration.
3-[2-(dimethylamino)ethyl]-N-methyl- which may be represented by the formula (I)
H
3 C CH3
NSO
2 CH CH 2
CH
2
N
2 Il I 2 N CH 3
N
H
and its physiologically acceptable salts and solvates are disclosed in UK Patent Specification No. 2162522. The compound of formula exhibits selective vasoconstrictor activity and is useful in the treatment of migraine.
Oral administration constitutes the generally preferred route for administration of pharmaceuticals since this route is particularly convenient and acceptable to patients. Unfortunately oral compositions may be associated with certain disadvantages in the treatment of conditions associated with cephalic pain. For example, such conditions, particularly migraine are associated with gastrointestinal dysfunction in the form of delayed gastric emptying. This leads to both a delay and an impairment of drug absorption and it is generally accepted that oral formulations of drugs for the treatment of such conditions should be administered in the form of a liquid preparation.
Numerous clinical studies have demonstrated the effectiveness of the compound of formula in migraineurs. Hitherto, the drug has always been administered either by parenteral injection or in the form of a dispersible tablet which is dispersed in drinking water prior to oral administration. This mode of oral i -2administration was believed to minimise the potential problems associated with gastrointestinal dysfunction in migraineurs.
However, it has been found that the compound of formula has a particularly unpleasant taste. When the compound of formula is administered orally this unpleasant taste may exacerbate the nausea and vomiting associated wmi migraine.
The present invention provides a particularly advantageous formulation suitable for oral administration of the compound of formula There is thus provided a pharmaceutical composition for oral administration comprising a film-coated solid dosage form including 25 to 200 mg of 3-[2- (dimethylamino)ethyl]-N-methyl-1 H-indole-5-methanesulphonamide as active ingredient or a pharmaceutically acceptable salt or solvate thereof, wherein the film-coating comprises 2 to 5% w/w of hydroxypropyl methylcellulose based on the weight of the solid dosage form.
The present invention also provides a pharmaceutical composition for oral administration comprising a film-coated solid dosage form including 25 to 200 mg of 3-[2-(dimethylamino)ethyl]-N-methyl-lH-indole-5-methanesulphonamide as active ingredient or a pharmaceutically acceptable salt or solvate thereof, wherein the filmcoating comprises hydroxypropyl cellulose, methyl cellulose or a copolymer of methacrylic acid and methyl methacrylate.
As used herein the term “film-coated solid dosage form” means a solid core comprising the active ingredient, which solid core is substantially covered with a film coating.
i.
a.
YI
95073 1,p:\opcr\dab, I3264.spe,2 i I 2a The compositions of the invention may comprise, for example, granules, tablets or capsules. Preferably the compositions of the invention will comprise tablets, most preferably compressed tablet.
There is provided in a preferred aspect of the invention a film coated tablet comprising a tablet core containing 25 to 200 mg of 3-[2-(dimethylamino)ethyl]-Nas active ingredient in the form of its succinate salt, together with one or more pharmaceutically acceptable carriers and excipients, and a polymeric film coat on said tablet core.
We have found that the unpleasant taste associated with oral administration of the compound of formula is substantially eliminated by the formulations of the present invention. The film coating also makes the formulations easier to handle and reduces potentially hazardous dust formation occurring during the packaging or administration of the drug. Surprisingly these advantages are attained without any significant loss in the bioavailability of the compound of formula when compared to aqueous solutions or dispersible tablet formulations for oral administration to 4 .r V r4 1 3 tiJJ’ 950623,p:\opr\dab,13264.spe,2 WO 92/15295 PCT/EP92/00460 -3migraineurs. Film-coated tablets according to the invention are therefore surprisingly effective in the treatment of migraine.
It is preferred that 3-[2-(dimethylamino)ethyl]-N-methyl-lH-indole-5methanesulphonamide should be employed in the compositions of the invention in the form of a physiologically acceptable salt. Such salts include salts of inorganic or organic acids such as hydrochloride, hydrobromide, sulphate, nitrate, phosphate, formate, mesylate, citrate, benzoate, fumarate, maleate, tartrate and succinate salts.
Most preferably 3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5methanesulphonamide will be employed in the compositions of the invention in the form of its succinate salt.
The film coating comprises a polymer. Suitable polymers include cellulose ethers, for example, hydroxypropyl methylcellulose, hydroxypropyl cellulose or methylcellulose, and copolymers of methacrylic acid and methyl methacrylate.
Preferably the film coating will comprise hydroxypropylmethyl cellulose.
The total film coating solids are generally applied to the solid dosage form, for example the tablet core, in an amount of from 2 to 5% w/w, preferably from 3 to 4% w/w, based on the weight of the solid dosage form.
The film coating may additionally comprise any pharmaceutically acceptable colourants or opacifiers including water soluble dyes, aluminium lakes of water soluble dyes and inorganic pigments such as titanium dioxide and iron oxide.
Suitable colourants or opacifiers may comprise from 5% to 65% w/w, preferably from 25 to 50% w/w, based on the dry weight of film coating.
The film coating may also contain one or more plasticizing agents conventionally used in polymeric film coatings, for example polyethylene glycol, propylene glycol, dibutyl sebecate, mineral oil, sesame oil, diethyl phthalate and triacetin. Suitable plasticizing agents may comprise 1 to 40% preferably 5 to w/w based on the dry weight of the film coating.
In addition to the compound of formula or a physiologically acceptable salt or solvate thereof, compositions of the invention will preferably comprise pharmaceutically acceptable carriers and excipients, such as binding agents (e.g.
pregelatinised maize starch, polyvinylpyrrolidone or
I
I WO 92/15295 PCT/EP92/00460 -4hydroxypropylmethylcellulose); fillers lactose, sucrose, mannitol, maize starch, microcrystalline cellulose or calcium hydrogen phosphate); lubricants stearic acid, polyethylene glycol, magnesium stearate, talc or silica); disintegrants (e.g.
potato starch, sodium starch glycollate or croscarmellose sodium); or wetting agents sodium lauryl sulphate).
For the preparation of compositions according to the invention 3-[2or a physiologically acceptable salt or solvate thereof may be blended with suitable excipients and, if desired, granulated. Preferably 3-[2-(dimethylamino)ethyl]-Nwill be granulated with a filler before admixture with the other excipients. Most preferably the filler employed will be lactose. Tablets in uncoated form may be prepared, for example, by compression of the powder blend or granulate, using a lubricant as an aid to tabletting. Compressed tablets are preferred.
The solid dosage form is then film-coated using a suspension comprising a suitable polymer in a suitable solvent. The preferred solvent for the film coating components is purified water but various classes of organic solvents commonly used in this art such as alcohols, ketones, ethers and chlorinated hydrocarbons, for example ethanol, acetone, methylene chloride and the like, may also be used. The solvent does not appear in the final product. The amount of solvent may be varied according to the equipment and coating conditions used to produce an aesthetically coated tablet.
The amount of 3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5methanesulphonamide, preferably in the form of a physiologically acceptable salt, employed in the compositions of the invention wtrin the range of about 25mg to about 200mg,mwe preferably about 50mg or 100mg, expressed as the weight of free base.
A further aspect of the invention provides a method of treating a mammal, including man, suffering from or susceptible to conditions associated with cephalic pain such as cluster headache, chronic paroxysmal hemicrania, headache associated S’ with vascular disorders, headache associated with substances or their withdrawal (for
L~
WO 92/15295 PCT/EP92/00460 example drug withdrawal), tension headache and in particular migraine which comprises oral administration of a pharmaceutical composition 6i NajkM- o g VK trf -2-t ,y i l) hylJ-N- T y i -ratanelpnmide or phrmapetienal p abnlehlsf~orsol-va4-et fag _aci,-.ineie-. t. It will be appreciated that reference to treatment is intended to include prophylaxis as well as the alleviation of established symptoms.
It will be appreciated that the precise therapeutic dose of the active ingredient will depend on the age and condition of the patient and the nature of the condition to be treated and will be at the ultimate discretion of the attendant physician.
However, in general effective doses for the treatment of conditions associated with cephalic pain, for example acute treatment of migraine, will lie in the range of to 500mg, preferably 20 to 300mg, most preferably 25 to 200mg, for example or 100mg of the ,ctive ingredient per unit dose which could be administered in single or divided doses, for example, 1 to 4 times per day.
The invention is further illustrated by the following non-limiting examples wherein the active ingredient is 3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5methanesulphonamide succinate.
Example 1 Tablet cores Unit formula (mg/tablet) Active ingredient/lactose granule 280.0 Microcrystalline Cellulose Ph Eur 15.5 Croscarmellose Sodium USNF Magnesium Stearate Ph Eur 1.25 1.75 *Active ingredient/lactose granule WO 92/15295 PCT/EP92/00460 -6- Compound of formula succinate 140.0** Lactose Ph Eur 170 mesh 140.0 Purified water Ph Eur qs The water does not appear in the final product. Typical range 100-140g per kg of blend Equivalent to 100mg free base Coating Suspension w/w Hydroxypropyl methylcellulose Ph Eur 10.0 Opaspray white Purified Water Ph Eur to 100.0++ The water does not appear in the final product. The maximum theoretical weight of solids applied during coating is 1 Img/tablet.
Opaspray white is a proprietory film coating suspension, obtainable from Colorcon Ltd, UK, which contains hydroxypropyl methylcellulose and titanium dioxide.
The active ingredient and lactose were mixed together and granulated by the addition of purified water. The granules obtained after mixing were dried and St. passed through a screen, and the resulting granules were then mixed with the other tablet core excipients. The mix was compressed into tablets. The tablets were then film coated using the coating suspension in conventional film coating equipment.
Example 2 ICL I i i ‘i -7- The tablet cores were prepared as described in Example 1. The tablets were then film coated using the coating suspension given below and conventional film coating equipment.
Coating Suspension w/w Opadry pink 5.3 Purified water Ph. Eur. to 100.0++ The water does not appear in the final product. The maximum theoretical weight of solids applied during coating is 9mg/tablet.
Opadry pink is a proprietory film coating material, obtainable from Colorcon Ltd, UK which contains hydroxypropyl methylcullulose, titanium dioxide, red iron oxide and triacetin.
Throughout this specification and the claims which follow, unless the context requires otherwise, the word “comprise”, or variations such as “comprises” or “comprising”, will be understood to imply the inclusion of a stated integer or group of integers but not the exclusion of any other integer or group of integers.
941209,p:\opt\dab, 13264.92.342,7

Claims (13)

1. A pharmaceutical composition for oral administration comprising a film-coated solid dosage form including 25 to 200 mg of 3-[2-(dimethylamino)ethyl]-N-methyl-1H- indole-5-methanesulphonamide as active ingredient or a pharmaceutically acceptable salt or solvate thereof, wherein the film-coating comprises 2 to 5% w/w of hydroxypropyl methylcellulose based on the weight of the solid dosage form.

2. A pharmaceutical composition for oral administration comprising a film-coated solid dosage form including 25 to 200 mg of 3-[2-(dimethylamino)ethyl]-N-methyl-lH- as active ingredient or a pharmaceutically acceptable salt or solvate thereof, wherein the film-coating comprises hydroxypropyl cellulose, methyl cellulose or a copolymer of methacrylic acid and methyl methacrylate.

3. A pharmaceutical composition as claimed in Claim 1 or Claim 2 wherein the active ingredient is in the form of its succinate salt.

4. A pharmaceutical composition as claimed in any one of Claims 1 to 3 in the form of a tablet. A pharmaceutical composition as claimed in Claim 4 in the form of a compression tablet.

6. A pharmaceutical composition as claimed in any one of Claims 2 to 5 wherein the film-coating comprises 2 to 5% w/w based on the weight of the solid dosage form.

7. A pharmaceutical composition as claimed in any one of Claims 1 to 6 wherein the film-coating additionally comprises one or more pharmaceutically acceptable colourants or opacifiers.

8. A pharmaceutical composition as claimed in Claim 7 wherein the colourants or opacifiers comprise 5 to 65% w/w based on the dry weight of the film-coating. ~95073 I,p\opcr\lnb,13264sp,8 t A I YI~I~_ -9-

9. A pharmaceutical composition as claimed in any one of Claims 1 to 8 wherein the film-coating further comprises one or more pharmaceutically acceptable plasticizing agents.

10. A pharmaceutical composition as claimed in Claim 9 wherein the plasticizing agents comprise 1 to 40% w/w based on the dry weight of the film-coating.

11. A film-coated tablet comprising a tablet core containing 25 to 200 mg of 3-[2- (dimethylamino)ethyl]-N-methyl-1 H-indole-5-methanesulphonamide as active ingredient in the form of its succinate salt, together with one or more pharmaceutically acceptable carriers and excipients, and a polymeric film-coat on said tablet core.

12. A film-coated tablet comprising a tablet core containing 25 to 200 mg of 3-[2- (dimethylamino)ethyl]-N-methyl- H-indole-5-methanesulphonamide as active ingredient in the form of its succinate salt, together with one or more pharmaceutically acceptable carriers and excipients, and a film-coat of hydroxypropyl methyl cellulose on said tablet core.

13. A film-coated tablet comprising a tablet core containing 25 to 200 mg of 3-[2- (dimethylamino)ethyl]-N-methyl-lH-indole-5-methanesulphonamide as active ingredient in the form of its succinate salt, together with one or more pharmaceutically acceptable carriers and excipients, and a film-coat of hydroxypropyl cellulose, methyl cellulose or a copolymer of methacrylic acid and methyl methacrylate on said tablet core. S14. A method of treating a mammal, including man, suffering from or susceptible to conditions associated with cephalic pain such as cluster headache, chronic paroxysmal hemicrania, headache associated with vascular disorders, headache associated with substances or their withdrawal (for example drug withdrawal), tension headache and in particular migraine which comprises oral administration of a pharmaceutical composition as claimed in any one of Claims 1 to 13. trU.. 950731,p:\perdab, 13264.spc,9 I 1 i 1- i.l .I I- Iii ii A process for the preparation of a pharmaceutical composition as claimed in any one of Claims 1 to 13 which comprises applying a film coating to a solid dosage form of the active ingredient by a film coating technique.

16. Pharmaceutical compositions or processes for their preparation, substantially as hereinbefore described with reference to the Examples. DATED this 1st day of August, 1995 Glaxo Group Limited By Its Patent Attorneys DAVIES COLLISON CAVE I.~r 0o r c’. S’I 95073 1,p:\opcr\dab,13264.spe, O r I c -I INTERNATIONAL SEARCH REPORT Internationf Applicatit- No PCT/EP 92/00460 PC/P9/06 I. CLASSIFICATION OF SUBJECT MATTER (if several classification symbols apply, indicate all) 6 According to International Patent Classification (IPC) or to both National Classification and IPC A 61 K 31/40 A 61 K 9/28 U. FIELDS SEARCHED Minimum Documentation Searched 7 Classification System Classification Symbols A 61 K Documentation Searched other than Minimum Documentation to the Extent that such Documents are Included in the Fields Searched’ Il. DOCUMENTS CONSIDERED TO BE RELEVANT 9 Category Citation of Document, 1 with indication, where appropriate, of the relevant passages 12 Relevant to Claim No. 1 3 X GB,A,2162522 (GLAXO) 5 February 1-10 1986, see the claims; page 10, lines 2-4 (cited in the application) A EP,A,0147107 (GLAXO) 3 July 1985, 1-10 see the claims 1,8; page 37, lines 8-10 Special categories of cited documents: to later document published after the international filing date or priority date and not in conflict with the application but document defining the general state of the art which is not cited to understand the principle or theory underlying the considered to be of particular relevance invention earlier document but published on or after the international document of particular relevance; the claimed invention filing date cannot be considered novel or cannot be considered to document which may throw doubts on priority claim(s) or involve an inventive step which is cited to establish the publication date of another document of particular relevance; the claimed invention citation or other special reason (as specified) cannot be considered to involve an inventive step when the 0O’ document referring to an oral disclosure, use, exhibition or document is combined with one or more other such docu- other means ments, such combination being obvious to a person skilled document published prior to the international filing date but in the at. later than the priority date claimed document member of the same patent family IV. CERTIFICATION Date of the Actual Completion of the International Search Date of Mailing of this International Search Report 14-04-1992 0.2 International Searching Authority Signature of Authorized Officer EUROPEAN PATENT OFFICE Y L Form PCTIISA/210 (tecmid ttjt IJanuary 19&51 M rm De;mar FRANK ~Lmru-^u^– International At ation No. PCTI EP92 100460 FURTHER INFORMATION CONTNUED FROM THE SECOND SHEET FURTHER INFORMATION CONTINUED FROM THE SECOND SHEET V. OBSERVATION WHERE CERTAIN CLAIMS WERE FOUND UNSEARCHABLE 1 This International search report has not been established in respect of certain claims under Article 17(2)(a) for the following reasons: 1. [I Claim numbers PLS. SEE REMARK because they relat to subject mattr not requird to be searched by this Authonty, namely ALTHOUGH CLAIM 9 IS DIRECTED TO A METHOD OF TREATMENT OF THE HUMAN/ANIMAL BODY BY THERAPY, THE SEARCH HAS BEEN CARRIED OUT AND BASED ON THE ALLEGED EFFECTS OF THE COMPOSITION. 2. 0 Claim numbers because they relate to parts of the International application that do not comply with the prescribed requirements to such an extent that no meaningful International search can be camed out, specifically. 3. -O Claim numbers the second and third sentenc of PCT Rule 6.4(a). because they are dependent claims and are not drafted in accordance with pk VI_ OBSERVATIONS WHERE UNITY OF INVENTION IS LACKING 2 This I;ternational Searching Authority found multiple Inventions in this International application as follows: 1. O As all requlred additional search fees were timely paid by the cppllcant, this International search report covrs all searchable claims of the International application 2. EO As only some of the required additional search fees were timely paid by the applicant, this nternational search report covers only those claims of the International application for which fees were paid, specifically claims: 3. O No required additional search fees were timely paid by the applicant. Consequently, this International search rport Is restricted to the invention first mentioned in the claims; It is covered by claim numbers: 4. FO As all searchable claims could be searched without effort justifying an additional fee, the Intemational Searching Authority did not invite payment of any additional fee. Remark on Protest I The additional search fees were accompanied by applicant’s protest, S]No protest accompanied the payment of additional search fees. Form PCT/ISA/210 (supplemental sheet P9412B 05/91 I ANNEX TO THE INTERNATIONAL SEARCH REPORT ON INTERNATIONAL PATENT APPLICATION NO. EP 9200460 SA 56867 This annex lists the patent family members relating to the patent documents cited in the above-mentioned international search report. The members are as contained in the European Patent Office EDP file on 28/04/92 The European Patent Office is in no way liable for these particulars which are merely given for the purpose of information. Patent document Publication Patent family Publication cited in search report date member(s) date GB-A- 2162522 05-02-86 AT-B- 386196 11-07-88 AU-B- 573878 23-06-88 AU-A- 4568985 06-02-86 BE-A- 903006 03-02-86 CA-A- 1241004 23-08-88 CH-A- 666026 30-06-88 DE-A- 3527648 13-02-86 FR-A,B 2568571 07-02-86 JP-A- 61047464 07-03-86 LU-A- 86032 18-02-86 NL-A- 8502171 03-03-86 SE-B- 452460 30-11-87 SE-A- 8503680 02-02-86 SU-A- 1498386 30-07-89 US-A- 5037845 06-08-91 EP-A- 0147107 03-07-85 AU-B- 574744 14-07-88 AU-A- 3636684 13-06-85 JP-A- 60139670 24-07-85 US-A- 4894387 16-01-90 a For more details about this annex :see Oficial Journal of the European Patent Oficc, No. 12/82 2 For more details about this annex :see Official Journal of the European Patent Office, No. 12/8z

AU13264/92A
1991-03-08
1992-03-02
Compositions containing sumatriptan

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Applications Claiming Priority (3)

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GB919104890A

GB9104890D0
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1991-03-08
1991-03-08
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1991-03-08

PCT/EP1992/000460

WO1992015295A1
(en)

1991-03-08
1992-03-02
Compositions containing sumatriptan

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1995-10-05

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Families Citing this family (56)

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Publication date
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GB9104890D0
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1991-03-08
1991-04-24
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Compositions

DE69222006T2
(en)

1991-10-30
1998-01-22
Glaxo Group Ltd

Multilayer compositions containing histamine or serotonin antagonists

DE4314976C1
(en)

1993-05-06
1994-10-06
Lohmann Therapie Syst Lts
Transdermal therapeutic systems for the administration of drugs, process for their production and their use

US8022095B2
(en)

1996-08-16
2011-09-20
Pozen, Inc.
Methods of treating headaches using 5-HT agonists in combination with long-acting NSAIDs

US6066092A
(en)

1997-11-06
2000-05-23
Cady; Roger K.
Preemptive prophylaxis of migraine device and method

US7189753B1
(en)

1997-11-06
2007-03-13
Cady Roger K
Preemptive prophylaxis of migraine

GB9924717D0
(en)

1999-10-19
1999-12-22
Glaxo Group Ltd
Diagnostic

AT500063A1
(en)

1999-11-23
2005-10-15
Sandoz Ag

COATED TABLETS

US20020064555A1
(en)

2000-09-29
2002-05-30
Dan Cullen
Proton pump inhibitor formulation

AU4061702A
(en)

2001-05-15
2003-04-03
Mcneil-Ppc, Inc.
Dip coating compositions containing starch or dextrin

US20030070584A1
(en)

2001-05-15
2003-04-17
Cynthia Gulian
Dip coating compositions containing cellulose ethers

US8329734B2
(en)

2009-07-27
2012-12-11
Afgin Pharma Llc
Topical therapy for migraine

EP1435945B1
(en)

2001-06-05
2008-08-13
Aung-din, Ronald
Topical migraine therapy

US8309118B2
(en)

2001-09-28
2012-11-13
Mcneil-Ppc, Inc.
Film forming compositions containing sucralose

GB0129117D0
(en)

2001-12-05
2002-01-23
Glaxo Group Ltd
Pharmaceutical composition

US20040052843A1
(en)

2001-12-24
2004-03-18
Lerner E. Itzhak
Controlled release dosage forms

US20030228363A1
(en)

2002-06-07
2003-12-11
Patel Mahendra R.
Stabilized pharmaceutical compositons containing benzimidazole compounds

WO2004009085A2
(en)

2002-07-19
2004-01-29
Ranbaxy Laboratories Limited
Taste masked sumatriptan tablets and processes for their preparation

US7429619B2
(en)

2002-08-02
2008-09-30
Mcneil Consumer Healthcare
Polyacrylic film forming compositions

US20040068000A1
(en)

2002-10-02
2004-04-08
Mintong Guo
Compression coated tablets

EP1575566B1
(en)

2002-12-26
2012-02-22
Pozen, Inc.
Multilayer dosage forms containing naproxen and triptans

US20080213363A1
(en)

2003-01-23
2008-09-04
Singh Nikhilesh N
Methods and compositions for delivering 5-HT3 antagonists across the oral mucosa

WO2004076403A1
(en)

2003-02-24
2004-09-10
Transform Pharmaceuticals, Inc.
Sumatriptan crystalline forms, pharmaceutical compositions and methods

JP2006527195A
(en)

2003-06-06
2006-11-30
グラクソ　グループ　リミテッド

Composition comprising triptan and NSAID

EP1644004A4
(en)

2003-06-20
2010-10-06
Ronald Aung-Din
Tropical therapy for the treatment of migraines, muscle sprains, muscle spasm, spasticity and related conditions

GB2407498B
(en)

2003-10-30
2008-06-11
Cipla Ltd
Oral formulations for 5-HT receptor agonists with reduced degradation of active ingredient

GB0400452D0
(en)

2004-01-09
2004-02-11
Norton Healthcare Ltd
A pharmaceutical composition

GB0403628D0
(en)

2004-02-18
2004-03-24
Arrow Group Ltd
Compression-coated tablets and the manufacture thereof

US8216610B2
(en)

2004-05-28
2012-07-10
Imaginot Pty Ltd.
Oral paracetamol formulations

JP2008500288A
(en)

2004-05-28
2008-01-10
イメイジノットピーティーワイエルティーディー

Oral therapeutic compound delivery system

EP1765300A2
(en)

2004-06-10
2007-03-28
Duramed Pharmaceuticals, Inc.
Formulations of sumatriptan for absorption across biological membranes, and methods of making and using the same

MY147767A
(en)

2004-06-16
2013-01-31
Janssen Pharmaceutica Nv
Novel sulfamate and sulfamide derivatives useful for the treatment of epilepsy and related disorders

MX2007014613A
(en)

2005-05-20
2008-04-02
Johnson & Johnson
Process for preparation of sulfamide derivatives.

WO2007059591A1
(en)

2005-11-28
2007-05-31
Imaginot Pty Ltd
Oral therapeutic compound delivery system

US20070166336A1
(en)

2005-12-13
2007-07-19
David Delmarre
Stable and palatable oral liquid sumatriptan compositions

US8492431B2
(en)

2005-12-19
2013-07-23
Janssen Pharmaceutica, N.V.
Use of benzo-fused heterocycle sulfamide derivatives for the treatment of obesity

US8497298B2
(en)

2005-12-19
2013-07-30
Janssen Pharmaceutica Nv
Use of benzo-fused heterocycle sulfamide derivatives for lowering lipids and lowering blood glucose levels

US8691867B2
(en)

2005-12-19
2014-04-08
Janssen Pharmaceutica Nv
Use of benzo-fused heterocycle sulfamide derivatives for the treatment of substance abuse and addiction

US8937096B2
(en)

2005-12-19
2015-01-20
Janssen Pharmaceutica Nv
Use of benzo-fused heterocyle sulfamide derivatives for the treatment of mania and bipolar disorder

US8716231B2
(en)

2005-12-19
2014-05-06
Janssen Pharmaceutica Nv
Use of benzo-fused heterocycle sulfamide derivatives for the treatment of pain

JP2009537635A
(en)

2006-05-19
2009-10-29
ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ

Co-therapy for treatment of hemorrhoids

EP2124556B1
(en)

2006-10-09
2014-09-03
Charleston Laboratories, Inc.
Pharmaceutical compositions

AU2007310949A1
(en)

2006-10-19
2008-04-24
Auspex Pharmaceuticals, Inc.
Substituted indoles

ES2620672T3
(en)

2008-01-09
2017-06-29
Charleston Laboratories, Inc.

Double layer tablets comprising oxycodone and promethazine

US20090252791A1
(en)

2008-04-02
2009-10-08
Venkata Nookaraju Sreedharala
Pharmaceutical compositions comprising a triptan and a nonsteroidal anti-inflammatory drug

WO2009152551A1
(en)

2008-06-20
2009-12-23
Alphapharm Pty Ltd
Pharmaceutical formulation

BRPI0915890A2
(en)

2008-06-23
2015-11-03
Janssen Pharmaceutica Nv

(2s) – (-) – n- (6-chloro-2,3-dihydro-benzo [1,4] dioxin-2-ylmethyl) sulfamide crystalline form

CA2729346A1
(en)

2008-06-30
2010-01-14
Afgin Pharma, Llc
Topical regional neuro-affective therapy

US8815939B2
(en)

2008-07-22
2014-08-26
Janssen Pharmaceutica Nv
Substituted sulfamide derivatives

CA2767576C
(en)

2009-07-08
2020-03-10
Charleston Laboratories Inc.
Pharmaceutical compositions comprising an antiemetic and an opioid analgesic

US11337962B2
(en)

2009-09-25
2022-05-24
Upsher-Smith Laboratories, Llc
Formulations comprising triptan compounds

MX338110B
(en)

2009-09-25
2016-04-01
Reddys Lab Ltd Dr
Formulations comprising triptan compounds.

CN107530318A
(en)

2015-03-02
2018-01-02
阿福金制药有限责任公司
Sex therapy is influenceed with the regional area nerve of cannboid

US10383816B2
(en)

2015-03-02
2019-08-20
Afgin Pharma, Llc
Topical regional neuro-affective therapy with cannabinoid combination products

CA3055170A1
(en)

2016-03-04
2017-09-08
Charleston Laboratories, Inc.
Pharmaceutical compositions

US20180049994A1
(en)

2016-08-16
2018-02-22
Afgin Pharma, Llc
Topical regional neuro-affective therapy with caryophyllene

Citations (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

GB2162522A
(en)

1984-08-01
1986-02-05

Glaxo Group Ltd

An indole derivative

Family Cites Families (5)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

GR79215B
(en)

1982-06-07
1984-10-22
Glaxo Group Ltd

GB8332437D0
(en)

1983-12-06
1984-01-11
Glaxo Group Ltd
Chemical compounds

GB8419575D0
(en)

1984-08-01
1984-09-05
Glaxo Group Ltd
Chemical compounds

GB8928208D0
(en)

1989-12-13
1990-02-14
Glaxo Group Ltd
Medicaments

GB9104890D0
(en)

1991-03-08
1991-04-24
Glaxo Group Ltd
Compositions

1991

1991-03-08
GB
GB919104890A
patent/GB9104890D0/en
active
Pending

1992

1992-03-02
EP
EP92103592A
patent/EP0503440B1/en
not_active
Expired – Lifetime

1992-03-02
KR
KR1019930702672A
patent/KR100202042B1/en
not_active
IP Right Cessation

1992-03-02
DE
DE69225421T
patent/DE69225421T2/en
not_active
Expired – Fee Related

1992-03-02
GE
GEAP19922601A
patent/GEP20012549B/en
unknown

1992-03-02
AU
AU13264/92A
patent/AU663303B2/en
not_active
Ceased

1992-03-02
WO
PCT/EP1992/000460
patent/WO1992015295A1/en
active
IP Right Grant

1992-03-02
DK
DK92103592T
patent/DK0503440T3/en
active

1992-03-02
JP
JP4504967A
patent/JP2986546B2/en
not_active
Expired – Fee Related

1992-03-02
RU
RU9393057724A
patent/RU2098093C1/en
not_active
IP Right Cessation

1992-03-02
CA
CA002105180A
patent/CA2105180C/en
not_active
Expired – Fee Related

1992-03-02
ES
ES92103592T
patent/ES2117015T3/en
not_active
Expired – Lifetime

1992-03-02
US
US08/381,422
patent/US5863559A/en
not_active
Expired – Fee Related

1992-03-02
CZ
CS931849A
patent/CZ282352B6/en
not_active
IP Right Cessation

1992-03-02
AT
AT92103592T
patent/ATE165973T1/en
not_active
IP Right Cessation

1992-03-05
GB
GB9204761A
patent/GB2254784B/en
not_active
Expired – Fee Related

1992-03-06
CH
CH727/92A
patent/CH684242A5/en
not_active
IP Right Cessation

1992-03-06
ZA
ZA921690A
patent/ZA921690B/en
unknown

1992-03-06
NL
NL9200423A
patent/NL9200423A/en
active
Search and Examination

1992-03-06
MX
MX9200992A
patent/MX9200992A/en
not_active
IP Right Cessation

1992-03-06
IL
IL101162A
patent/IL101162A/en
unknown

1992-03-06
NZ
NZ241873A
patent/NZ241873A/en
unknown

1992-03-06
BE
BE9200230A
patent/BE1005086A5/en
not_active
IP Right Cessation

1992-03-06
FR
FR9202709A
patent/FR2673538B1/en
not_active
Expired – Fee Related

1992-03-06
IE
IE072692A
patent/IE920726A1/en
not_active
IP Right Cessation

1992-03-06
IT
ITRM920155A
patent/IT1271495B/en
active
IP Right Grant

1993

1993-08-19
OA
OA60402A
patent/OA09812A/en
unknown

1994

1994-12-01
SG
SG169294A
patent/SG169294G/en
unknown

1995

1995-02-09
HK
HK19395A
patent/HK19395A/en
not_active
IP Right Cessation

1998

1998-02-20
CY
CY201198A
patent/CY2011A/en
unknown

1998-07-24
US
US09/121,530
patent/US6020001A/en
not_active
Expired – Fee Related

2000

2000-01-13
US
US09/481,933
patent/US6368627B1/en
not_active
Expired – Fee Related

2002

2002-02-28
US
US10/084,683
patent/US20020197318A1/en
not_active
Abandoned

Patent Citations (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

GB2162522A
(en)

1984-08-01
1986-02-05
Glaxo Group Ltd
An indole derivative

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GB2254784B
(en)

1994-11-16

DK0503440T3
(en)

1999-01-18

IL101162A
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1997-11-20

CY2011A
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1998-02-20

NL9200423A
(en)

1992-10-01

FR2673538B1
(en)

1995-05-12

MX9200992A
(en)

1992-09-01

ATE165973T1
(en)

1998-05-15

ZA921690B
(en)

1993-08-02

CZ184993A3
(en)

1994-06-15

EP0503440B1
(en)

1998-05-13

BE1005086A5
(en)

1993-04-13

ES2117015T3
(en)

1998-08-01

OA09812A
(en)

1994-04-15

NZ241873A
(en)

1994-06-27

CA2105180C
(en)

1999-08-17

JP2986546B2
(en)

1999-12-06

JPH06505020A
(en)

1994-06-09

SG169294G
(en)

1995-04-28

US20020197318A1
(en)

2002-12-26

IL101162A0
(en)

1992-11-15

AU1326492A
(en)

1992-10-06

CH684242A5
(en)

1994-08-15

RU2098093C1
(en)

1997-12-10

DE69225421D1
(en)

1998-06-18

DE69225421T2
(en)

1998-10-15

GB9104890D0
(en)

1991-04-24

WO1992015295A1
(en)

1992-09-17

EP0503440A1
(en)

1992-09-16

ITRM920155D0
(en)

1992-03-06

GB9204761D0
(en)

1992-04-15

IT1271495B
(en)

1997-05-30

US6368627B1
(en)

2002-04-09

CZ282352B6
(en)

1997-07-16

US6020001A
(en)

2000-02-01

FR2673538A1
(en)

1992-09-11

CA2105180A1
(en)

1992-09-09

US5863559A
(en)

1999-01-26

GEP20012549B
(en)

2001-10-25

IE920726A1
(en)

1992-09-09

GB2254784A
(en)

1992-10-21

ITRM920155A1
(en)

1993-09-06

KR100202042B1
(en)

1999-06-15

HK19395A
(en)

1995-02-17

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