GB1058675A - Creation of Inventions and Patents with Artificial Intelligence

GB1058675A – New spiroalkane derivatives
– Google Patents

GB1058675A – New spiroalkane derivatives
– Google Patents
New spiroalkane derivatives

Info

Publication number
GB1058675A

GB1058675A
GB21780/64A
GB2178064A
GB1058675A
GB 1058675 A
GB1058675 A
GB 1058675A
GB 21780/64 A
GB21780/64 A
GB 21780/64A
GB 2178064 A
GB2178064 A
GB 2178064A
GB 1058675 A
GB1058675 A
GB 1058675A
Authority
GB
United Kingdom
Prior art keywords
formula
integer
aza
hal
spiroalkane
Prior art date
1963-05-27
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.)

Expired

Application number
GB21780/64A
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.)

DAUSSE LAB

Original Assignee
DAUSSE LAB
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.)
1963-05-27
Filing date
1964-05-26
Publication date
1967-02-15

1964-05-26
Application filed by DAUSSE LAB
filed
Critical
DAUSSE LAB

1967-02-15
Publication of GB1058675A
publication
Critical
patent/GB1058675A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

150000001875
compounds
Chemical class

0.000
abstract
6

239000002253
acid
Substances

0.000
abstract
3

125000001453
quaternary ammonium group
Chemical group

0.000
abstract
3

150000003839
salts
Chemical class

0.000
abstract
3

-1
C1- 6 alkylene radical
Chemical class

0.000
abstract
2

229930013930
alkaloid
Natural products

0.000
abstract
2

239000000203
mixture
Substances

0.000
abstract
2

230000000054
salidiuretic effect
Effects

0.000
abstract
2

DNXIKVLOVZVMQF-UHFFFAOYSA-N
(3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester
Natural products

C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1
DNXIKVLOVZVMQF-UHFFFAOYSA-N
0.000
abstract
1

SZLZWPPUNLXJEA-UHFFFAOYSA-N
11,17-dimethoxy-18-[3-(3,4,5-trimethoxy-phenyl)-acryloyloxy]-yohimbane-16-carboxylic acid methyl ester
Natural products

C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(OC)C1OC(=O)C=CC1=CC(OC)=C(OC)C(OC)=C1
SZLZWPPUNLXJEA-UHFFFAOYSA-N
0.000
abstract
1

CJDRUOGAGYHKKD-RQBLFBSQSA-N
1pon08459r
Chemical compound

CN([C@H]1[C@@]2(C[C@@]3([H])[C@@H]([C@@H](O)N42)CC)[H])C2=CC=CC=C2[C@]11C[C@@]4([H])[C@H]3[C@H]1O
CJDRUOGAGYHKKD-RQBLFBSQSA-N
0.000
abstract
1

URZHJTCEXXIFLG-UHFFFAOYSA-N
6-chloro-3-(4-fluorophenyl)-3-methyl-1,1-dioxo-2,4-dihydro-1lambda6,2,4-benzothiadiazine-7-sulfonamide
Chemical compound

FC1=CC=C(C=C1)C1(NS(C2=C(N1)C=C(C(=C2)S(N)(=O)=O)Cl)(=O)=O)C
URZHJTCEXXIFLG-UHFFFAOYSA-N
0.000
abstract
1

CJDRUOGAGYHKKD-UHFFFAOYSA-N
Iso-ajmalin
Natural products

CN1C2=CC=CC=C2C2(C(C34)O)C1C1CC3C(CC)C(O)N1C4C2
CJDRUOGAGYHKKD-UHFFFAOYSA-N
0.000
abstract
1

LCGISIDBXHGCDW-VKHMYHEASA-N
L-glutamine amide
Chemical compound

NC(=O)[C@@H](N)CCC(N)=O
LCGISIDBXHGCDW-VKHMYHEASA-N
0.000
abstract
1

244000061121
Rauvolfia serpentina
Species

0.000
abstract
1

SZLZWPPUNLXJEA-FMCDHCOASA-N
Rescinnamine
Natural products

O=C(O[C@H]1[C@@H](OC)[C@@H](C(=O)OC)[C@@H]2[C@H](C1)CN1[C@@H](c3[nH]c4c(c3CC1)ccc(OC)c4)C2)/C=C/c1cc(OC)c(OC)c(OC)c1
SZLZWPPUNLXJEA-FMCDHCOASA-N
0.000
abstract
1

LCQMZZCPPSWADO-UHFFFAOYSA-N
Reserpilin
Natural products

COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12
LCQMZZCPPSWADO-UHFFFAOYSA-N
0.000
abstract
1

QEVHRUUCFGRFIF-SFWBKIHZSA-N
Reserpine
Natural products

O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3
QEVHRUUCFGRFIF-SFWBKIHZSA-N
0.000
abstract
1

VTVQHYQGTTVKDE-FXBSTXGRSA-N
Sarpagine
Natural products

CC=C1CN2[C@H]3Cc4c([nH]c5ccc(O)cc45)[C@@H]2C[C@@H]1[C@H]3CO
VTVQHYQGTTVKDE-FXBSTXGRSA-N
0.000
abstract
1

229960004332
ajmaline
Drugs

0.000
abstract
1

150000003797
alkaloid derivatives
Chemical class

0.000
abstract
1

125000000217
alkyl group
Chemical group

0.000
abstract
1

239000002775
capsule
Substances

0.000
abstract
1

125000002915
carbonyl group
Chemical group

[*:2]C([*:1])=O

0.000
abstract
1

239000008298
dragée
Substances

0.000
abstract
1

239000003937
drug carrier
Substances

0.000
abstract
1

239000012458
free base
Substances

0.000
abstract
1

125000005843
halogen group
Chemical group

0.000
abstract
1

230000001077
hypotensive effect
Effects

0.000
abstract
1

125000002496
methyl group
Chemical group

[H]C([H])([H])*

0.000
abstract
1

125000001570
methylene group
Chemical group

[H]C([H])([*:1])[*:2]

0.000
abstract
1

ADFKWOUMZCHRTD-QDHOPYFXSA-O
raupine
Chemical compound

C1=C(O)C=C2C(C[C@@H]3[N+]4=C/C([C@@H](C[C@H]44)[C@H]3CO)=C/C)=C4NC2=C1
ADFKWOUMZCHRTD-QDHOPYFXSA-O
0.000
abstract
1

SMSAPZICLFYVJS-QEGASFHISA-N
rescinnamine
Chemical compound

O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)\C=C\C1=CC(OC)=C(OC)C(OC)=C1
SMSAPZICLFYVJS-QEGASFHISA-N
0.000
abstract
1

229960001965
rescinnamine
Drugs

0.000
abstract
1

BJOIZNZVOZKDIG-MDEJGZGSSA-N
reserpine
Chemical compound

O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1
BJOIZNZVOZKDIG-MDEJGZGSSA-N
0.000
abstract
1

229960003147
reserpine
Drugs

0.000
abstract
1

MDMGHDFNKNZPAU-UHFFFAOYSA-N
roserpine
Natural products

C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1
MDMGHDFNKNZPAU-UHFFFAOYSA-N
0.000
abstract
1

239000003826
tablet
Substances

0.000
abstract
1

230000001225
therapeutic effect
Effects

0.000
abstract
1

Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 – C07D219/00

C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 – C07D219/00 condensed with carbocyclic rings or ring systems

C07D221/20—Spiro-condensed ring systems

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

Abstract

Novel compounds of the Formula I wherein k represents an integer from 1 to 7, m represents 0 or an integer from 1 to 3 and n represents an integer from 1 to 4, the sum of k, m and n being at least 3 and at most 8, and A is a straight or branched C1- 6 alkylene radical, and acid addition salts and quaternary ammonium derivatives thereof, are prepared by reacting compounds of the Formula II with a compound of the formula Q-NH2, where Q represents a group of the formula R-S-C(: NH)-, R-O-C(: NH)- or NC- where R represents an alkyl group, or by reacting a compound of the Formula III with a compound of the formula Hal-A-NH-C(: NH)-NH2 or Hal-A1-CO-NH-C(: NH)-NH2, where Hal represents a halogen atom and A1 is such that -A1-CH2- is the same as A, and where appropriate converting a carbonyl group to a methylene group and if desired, converting a free base into an acid addition salt or quaternary ammonium derivative thereof. N – (o – Aminoalkyl) – aza – spiroalkanes of the Formula II may be prepared by reacting an unsubstituted aza-spiroalkane with an o -haloalkyl nitrile and reducing the resulting N – (o – cyanoalkyl) – aza – spiroalkane. Unsubstituted aza – spiroalkanes may be obtained by reducing the corresponding cyclicimides.ALSO:Therapeutic compositions with hypotensive properties comprise compounds of the formula wherein k represent an integer from 1 to 7, m represents O or an integer from 1 to 3 and n represents an integer from 1 to 4, the sum of k, m and n being at least 3 and a most 8, and A represents a straight or branched C1-6 alkylene radical or acid addition salts or quaternary ammonium derivatives thereof in association with a pharmaceutically acceptable carrier, optionally in conjunction with a Reuwolfia alkaloid or a salidiuretic. Suitable Reuwolfia alkaloids include reserpine, rescinnamine, raupine, ajmaline and methyl yohimbate and the salidiuretic may be p-fluorophenyl-3-methyl-7- sulphamyl-6- chloro-3,4- dihydro-1,2, 4-benzthiadiazine 1,1-dioxide. The compositions may be administered orally in the forms of tablets, dragees and capsules or parenterally.

GB21780/64A
1963-05-27
1964-05-26
New spiroalkane derivatives

Expired

GB1058675A
(en)

Applications Claiming Priority (2)

Application Number
Priority Date
Filing Date
Title

FR936120A

FR1426082A
(en)

1963-05-27
1963-05-27

New n- (omega-guanidinoalcoyl) azaspiroalkanes

FR936591A

FR3013M
(en)

1963-05-27
1963-05-30

New n- (ω-guanidinoalcoyl) azaspiroalkanes and their salts.

Publications (1)

Publication Number
Publication Date

GB1058675A
true

GB1058675A
(en)

1967-02-15

Family
ID=26201526
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB21780/64A
Expired

GB1058675A
(en)

1963-05-27
1964-05-26
New spiroalkane derivatives

Country Status (12)

Country
Link

US
(1)

US3326925A
(en)

BE
(1)

BE648317A
(en)

BR
(1)

BR6459494D0
(en)

CH
(1)

CH441329A
(en)

DE
(1)

DE1470010B1
(en)

DK
(1)

DK122886B
(en)

FR
(2)

FR1426082A
(en)

GB
(1)

GB1058675A
(en)

LU
(1)

LU46155A1
(en)

NL
(2)

NL6405907A
(en)

OA
(1)

OA00117A
(en)

SE
(1)

SE301651B
(en)

Cited By (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US5939450A
(en)

1995-07-13
1999-08-17
Anormed Inc.
N,N-dimethyl-8,8-dipropyl-2-azaspiro 4.5!decane-2-propanamine dimaleate

Families Citing this family (3)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US4963557A
(en)

1987-09-28
1990-10-16
Smithkline Beecham Corporation
Immunomodulatory azaspiranes

CA1336090C
(en)

1988-08-31
1995-06-27
Isao Hayakawa
Spiro-substituted cyclic amines of quinolone derivatives

US5591748A
(en)

1991-06-07
1997-01-07
Smithkline Beecham Corporation
Immunomodulatory azaspiranes

Family Cites Families (5)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US3078272A
(en)

1963-02-19

N-aza-bicyclo-alkylene-imino

DE1100637B
(en)

1958-06-10
1961-03-02
Ciba Geigy

Process for the preparation of alkyleniminoalkylguanidines, their acyl compounds, salts and quaternary ammonium compounds

US3106552A
(en)

1960-07-19
1963-10-08
Geschickter Fund Med Res
Nu-substituted azaspiranes and azaspirane-diones and processes for their preparation

US3200118A
(en)

1961-10-31
1965-08-10
Geschickter Fund Med Res
Spirocyclic hydrazine imides

US3189601A
(en)

1964-01-10
1965-06-15
Ciba Geigy Corp
N, n-alkylene-imino-lower alkanoamidine compounds

BE
BE648317D
patent/BE648317A/xx
unknown

NL
NL124128D
patent/NL124128C/xx
active

1963

1963-05-27
FR
FR936120A
patent/FR1426082A/en
not_active
Expired

1963-05-30
FR
FR936591A
patent/FR3013M/en
not_active
Expired

1964

1964-05-25
LU
LU46155D
patent/LU46155A1/xx
unknown

1964-05-26
CH
CH683264A
patent/CH441329A/en
unknown

1964-05-26
GB
GB21780/64A
patent/GB1058675A/en
not_active
Expired

1964-05-26
DE
DE19641470010
patent/DE1470010B1/en
active
Pending

1964-05-26
US
US370343A
patent/US3326925A/en
not_active
Expired – Lifetime

1964-05-27
SE
SE6448/64A
patent/SE301651B/xx
unknown

1964-05-27
DK
DK264364AA
patent/DK122886B/en
unknown

1964-05-27
NL
NL6405907A
patent/NL6405907A/xx
unknown

1964-05-27
BR
BR159494/64A
patent/BR6459494D0/en
unknown

1964-05-28
OA
OA50127A
patent/OA00117A/en
unknown

Cited By (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US5939450A
(en)

1995-07-13
1999-08-17
Anormed Inc.
N,N-dimethyl-8,8-dipropyl-2-azaspiro 4.5!decane-2-propanamine dimaleate

Also Published As

Publication number
Publication date

BE648317A
(en)

FR3013M
(en)

1964-12-21

NL6405907A
(en)

1964-11-30

DE1470010B1
(en)

1969-12-18

US3326925A
(en)

1967-06-20

BR6459494D0
(en)

1973-08-02

SE301651B
(en)

1968-06-17

OA00117A
(en)

1966-01-15

FR1426082A
(en)

1966-01-28

DK122886B
(en)

1972-04-24

NL124128C
(en)

LU46155A1
(en)

1972-01-01

CH441329A
(en)

1967-08-15

Contact information