GB1398291A - Creación de Inventos y Patentes con Inteligencia Artificial

GB1398291A – Prostaglandin analogues and production thereof
– Google Patents

GB1398291A – Prostaglandin analogues and production thereof
– Google Patents
Prostaglandin analogues and production thereof

Info

Publication number
GB1398291A

GB1398291A
GB1970672A
GB1970672A
GB1398291A
GB 1398291 A
GB1398291 A
GB 1398291A
GB 1970672 A
GB1970672 A
GB 1970672A
GB 1970672 A
GB1970672 A
GB 1970672A
GB 1398291 A
GB1398291 A
GB 1398291A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
octenyl
analogues
trans
formulae
Prior art date
1971-04-30
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
GB1970672A
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.)

Ono Pharmaceutical Co Ltd

Original Assignee
Ono Pharmaceutical Co 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.)
1971-04-30
Filing date
1972-04-27
Publication date
1975-06-18

1971-11-17
Priority claimed from JP9211371A
external-priority
patent/JPS4854068A/ja

1972-04-27
Application filed by Ono Pharmaceutical Co Ltd
filed
Critical
Ono Pharmaceutical Co Ltd

1975-06-18
Publication of GB1398291A
publication
Critical
patent/GB1398291A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

229940006138
antiglaucoma drug and miotics prostaglandin analogues
Drugs

0.000
title
1

229940094443
oxytocics prostaglandins
Drugs

0.000
abstract
5

150000003180
prostaglandins
Chemical class

0.000
abstract
5

-1
2-tetrahydropyranyl
Chemical group

0.000
abstract
3

150000002148
esters
Chemical class

0.000
abstract
3

230000003301
hydrolyzing effect
Effects

0.000
abstract
3

229920000858
Cyclodextrin
Polymers

0.000
abstract
2

WTDHULULXKLSOZ-UHFFFAOYSA-N
Hydroxylamine hydrochloride
Chemical compound

Cl.ON
WTDHULULXKLSOZ-UHFFFAOYSA-N
0.000
abstract
2

MZRVEZGGRBJDDB-UHFFFAOYSA-N
N-Butyllithium
Chemical compound

[Li]CCCC
MZRVEZGGRBJDDB-UHFFFAOYSA-N
0.000
abstract
2

150000001298
alcohols
Chemical class

0.000
abstract
2

150000001875
compounds
Chemical class

0.000
abstract
2

150000003839
salts
Chemical class

0.000
abstract
2

HFHDHCJBZVLPGP-UHFFFAOYSA-N
schardinger α-dextrin
Chemical compound

O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO
HFHDHCJBZVLPGP-UHFFFAOYSA-N
0.000
abstract
2

VEVBZRMVHQZQEC-UHFFFAOYSA-N
(4-ethyl-2-methyl-3-oxooctan-2-yl)phosphonic acid
Chemical compound

CCCCC(CC)C(=O)C(C)(C)P(=O)(O)O
VEVBZRMVHQZQEC-UHFFFAOYSA-N
0.000
abstract
1

DFXYFRLRTGSPPR-UHFFFAOYSA-N
1-diethoxyphosphorylheptan-2-one
Chemical class

CCCCCC(=O)CP(=O)(OCC)OCC
DFXYFRLRTGSPPR-UHFFFAOYSA-N
0.000
abstract
1

WIYMDOCSCMPUJI-UHFFFAOYSA-N
1-dimethoxyphosphoryl-3,3-dimethylheptan-2-one
Chemical compound

CCCCC(C)(C)C(=O)CP(=O)(OC)OC
WIYMDOCSCMPUJI-UHFFFAOYSA-N
0.000
abstract
1

RYCSYYMZXSIBJI-UHFFFAOYSA-N
1-dimethoxyphosphoryl-3-methylheptan-2-one
Chemical compound

CCCCC(C)C(=O)CP(=O)(OC)OC
RYCSYYMZXSIBJI-UHFFFAOYSA-N
0.000
abstract
1

AITHRLYLAMRNSQ-UHFFFAOYSA-N
5-(triphenyl-$l^{5}-phosphanylidene)pentanoic acid
Chemical compound

C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CCCCC(=O)O)C1=CC=CC=C1
AITHRLYLAMRNSQ-UHFFFAOYSA-N
0.000
abstract
1

101000692460
Bos taurus Prostaglandin F synthase 1
Proteins

0.000
abstract
1

101000692466
Bos taurus Prostaglandin F synthase 2
Proteins

0.000
abstract
1

YXAGIRHBJJLWHW-UHFFFAOYSA-N
Ethyl 2-ethylhexanoate
Chemical compound

CCCCC(CC)C(=O)OCC
YXAGIRHBJJLWHW-UHFFFAOYSA-N
0.000
abstract
1

ABLZXFCXXLZCGV-UHFFFAOYSA-N
Phosphorous acid
Chemical class

OP(O)=O
ABLZXFCXXLZCGV-UHFFFAOYSA-N
0.000
abstract
1

DHXVGJBLRPWPCS-UHFFFAOYSA-N
Tetrahydropyran
Chemical compound

C1CCOCC1
DHXVGJBLRPWPCS-UHFFFAOYSA-N
0.000
abstract
1

239000000969
carrier
Substances

0.000
abstract
1

125000000118
dimethyl group
Chemical group

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

0.000
abstract
1

VONWDASPFIQPDY-UHFFFAOYSA-N
dimethyl methylphosphonate
Chemical compound

COP(C)(=O)OC
VONWDASPFIQPDY-UHFFFAOYSA-N
0.000
abstract
1

230000000694
effects
Effects

0.000
abstract
1

238000006266
etherification reaction
Methods

0.000
abstract
1

LFLSVOVPJVCWKQ-UHFFFAOYSA-N
ethyl 2-methylhexanoate
Chemical compound

CCCCC(C)C(=O)OCC
LFLSVOVPJVCWKQ-UHFFFAOYSA-N
0.000
abstract
1

ZDAFYPGTJKATQZ-UHFFFAOYSA-N
ethyl 3,3-dimethylhexanoate
Chemical compound

CCCC(C)(C)CC(=O)OCC
ZDAFYPGTJKATQZ-UHFFFAOYSA-N
0.000
abstract
1

238000005984
hydrogenation reaction
Methods

0.000
abstract
1

150000002596
lactones
Chemical class

0.000
abstract
1

150000004702
methyl esters
Chemical class

0.000
abstract
1

125000002496
methyl group
Chemical group

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

0.000
abstract
1

230000001590
oxidative effect
Effects

0.000
abstract
1

239000008194
pharmaceutical composition
Substances

0.000
abstract
1

238000010561
standard procedure
Methods

0.000
abstract
1

Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom

C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems

C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered

C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups

C07C405/0025—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing keto groups

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings

C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members

C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms

C07D309/10—Oxygen atoms

C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM

C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System

C07F9/02—Phosphorus compounds

C07F9/28—Phosphorus compounds with one or more P—C bonds

C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)

C07F9/40—Esters thereof

C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic

C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl

Abstract

1398291 Prostaglandins; acylmethane phosphonates ONO PHARMACEUTICAL CO Ltd 27 April 1972 [30 April 1971 17 Nov 1971] 10 Dec 1971] 19706/72 Headings C2C and C2P [Also in Division C3] The invention comprises optically active prostaglandins of the formulae IX, X, XI, XII XIII and XIV wherein X 1 is 3-(R or S)-hydroxy-4-(R or S) methyl – trans – 1 – octenyl, 3 – (S) – hydroxy- 4,4 – dimethyl – trans – 1 – octenyl, or 4 – ethyl- 3-(S)-hydroxy-trans-1-octenyl, the esters thereof, salts thereof, the cyclodextrin clathrates thereof and the esters thereof, PG alcohol derivatives thereof, and the dihydro-PG 1 derivatives thereof, and optically active prostaglandins of the Formulae XV and XVII wherein THP is 2-tetrahydropyranyl and X 2 is 4-(R or S)-methyl-3-(R or S)-tetrahydropyran- 21 – yloxy – trans – 1 – octenyl, 4,4 – dimethyl – 3- (S) – tetrahydropyran – 21 – yloxy – trans – 1- octenyl, or 4-ethyl-3-(S)-tetrahydropyran-21- yloxy-trans-1-octenyl and their preparation The PGA analogues of Formulae XIII and XIV are prepared by dehydrating the corresponding PGE analogues of the Formulae XI and XII, which are made by oxidizing the 9- hydroxy group in compounds of the Formulae XV and XVII and hydrolysing the resulting products. PGF analogues of the Formulae IX and X are prepared by hydrolysing the corresponding PGF analogues of the Formulae XV and XVII. The dihydro-PG 1 analogues are obtained by hydrogenating the corresponding PG 1 analogues. The corresponding ester, alcohols, salts and cyclodextrin clathrates are prepared by standard methods. PGF 1 analogues of the Formula XVII are made by the selective hydrogenation of the corresponding PGF 2 analogues of the Formula XV which are prepared by reacting 4-carboxybutylidenetriphenylphosphorane with cyclopenta[b]p-urans of the formula obtained by reducing the corresponding lactones, resulting from the etherification of the corresponding 5a-hydroxy-4#-X 1 -3,3a#,4,5,6,6a#-hexahydro-2H-cyclopenta[b]-furan-2-ones, which are made by hydrolysing the appropriate 5α- acetoxy – 4# – X 1 – 3,3a#,4,5,6,6a# – hexahydro – 2H – cyclopenta[b]furan – 2 – ones, obtained by reducing the corresponding 5α- acetoxy – 4# – (3 – oxo – octenyl) – 3,3a#,4,5,6,6a#- hexahydro – 2H – cyclopenta[b]furan – 2 – ones, which are prepared by reacting 5α-acetoxy-4#- formyl – 3,3a#,4,5,6,6a# – hexahydro – 2H – cyclopenta[b]furan-2-one with the appropriate dimethyl or diethyl 2-oxoheptylphosphonates. 4α – Hydroxy – 2α – (7 – hydroxy – cis – 2- heptenyl) – 3# – (3 – (S) – hydroxy – 4 – (S)- methyl – trans – 1 – octenyl)cyclopentanone oxime is obtained by reducing 4α-hydroxy-2α-(6- methoxycarbonyl – cis – 2 – hexenyl) – 3# – (3 – (S)- hydroxy – 4 – (S) – methyl – trans-1-octenyl)cyclopentanone oxime, which is prepared by reacting the methyl ester of 16-(S)-methyl-PGE 2 with hydroxylamine hydrochloride. Dimethyl – 2 – oxo – 3 – methylheptylphosphonate, dimethyl – 2 – oxo – 3,3 – dimethylheptylphosphonate and dimethyl-2-oxo-3-ethylheptylphosphonate are prepared by dimethyl methylphosphonate with ethyl 2-methylhexanoate, ethyl 3,3-dimethylhexanoate and ethyl 2-ethylhexanoate respectively in the presence of butyllithium. Pharmaceutical compositions, suitable for oral, parenteral, sublingual, vaginal and rectal administration, contain the prostaglandins of the Formulae IX to XIV or derivatives thereof and suitable carriers. The compounds possess similar activities to those of naturally occurring prostaglandins. Reference has been directed by the Comptroller to Specification 1,198,071.

GB1970672A
1971-04-30
1972-04-27
Prostaglandin analogues and production thereof

Expired

GB1398291A
(en)

Applications Claiming Priority (3)

Application Number
Priority Date
Filing Date
Title

JP2909671

1971-04-30

JP9211371A

JPS4854068A
(en)

1971-11-17
1971-11-17

JP46099936A

JPS4864073A
(en)

1971-04-30
1971-12-10

Publications (1)

Publication Number
Publication Date

GB1398291A
true

GB1398291A
(en)

1975-06-18

Family
ID=27286426
Family Applications (2)

Application Number
Title
Priority Date
Filing Date

GB1970672A
Expired

GB1398291A
(en)

1971-04-30
1972-04-27
Prostaglandin analogues and production thereof

GB38475A
Expired

GB1398838A
(en)

1971-04-30
1972-04-27
Prostaglandin analogues and production thereof

Family Applications After (1)

Application Number
Title
Priority Date
Filing Date

GB38475A
Expired

GB1398838A
(en)

1971-04-30
1972-04-27
Prostaglandin analogues and production thereof

Country Status (12)

Country
Link

JP
(1)

JPS4864073A
(en)

AR
(1)

AR196490A1
(en)

BE
(1)

BE782822A
(en)

CA
(1)

CA988083A
(en)

CH
(1)

CH575368A5
(en)

DD
(1)

DD99563A5
(en)

DE
(1)

DE2221301A1
(en)

ES
(1)

ES402263A1
(en)

GB
(2)

GB1398291A
(en)

HU
(1)

HU168838B
(en)

NL
(1)

NL7205806A
(en)

SE
(1)

SE7507619L
(en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

JPS4949963A
(en)

1972-09-16
1974-05-15

US3962312A
(en)

1972-09-21
1976-06-08
Ono Pharmaceutical Company
9,11,15-Trihydroxy prost-5-enoic acid analogues

IL50310A
(en)

1972-11-08
1977-08-31
Pfizer
Dimethyl ketophosphonates

JPS5720305B2
(en)

1973-02-28
1982-04-27

JPS5823393B2
(en)

1974-03-14
1983-05-14
オノヤクヒンコウギヨウカブシキガイシヤ

prostaglandin

1971

1971-12-10
JP
JP46099936A
patent/JPS4864073A/ja
active
Pending

1972

1972-04-27
GB
GB1970672A
patent/GB1398291A/en
not_active
Expired

1972-04-27
GB
GB38475A
patent/GB1398838A/en
not_active
Expired

1972-04-28
AR
AR241703A
patent/AR196490A1/en
active

1972-04-28
BE
BE782822A
patent/BE782822A/en
unknown

1972-04-28
CH
CH636272A
patent/CH575368A5/xx
not_active
IP Right Cessation

1972-04-28
NL
NL7205806A
patent/NL7205806A/xx
not_active
Application Discontinuation

1972-04-29
HU
HUOO180A
patent/HU168838B/hu
unknown

1972-04-29
ES
ES402263A
patent/ES402263A1/en
not_active
Expired

1972-04-29
DE
DE19722221301
patent/DE2221301A1/en
active
Pending

1972-05-01
CA
CA141,153A
patent/CA988083A/en
not_active
Expired

1972-05-02
DD
DD162679A
patent/DD99563A5/xx
unknown

1975

1975-07-02
SE
SE7507619A
patent/SE7507619L/en
unknown

Also Published As

Publication number
Publication date

GB1398838A
(en)

1975-06-25

NL7205806A
(en)

1972-11-01

SE7507619L
(en)

1975-07-02

CH575368A5
(en)

1976-05-14

DE2221301A1
(en)

1972-11-23

AR196490A1
(en)

1974-02-06

ES402263A1
(en)

1976-01-01

DD99563A5
(en)

1973-08-12

JPS4864073A
(en)

1973-09-05

BE782822A
(en)

1972-08-16

CA988083A
(en)

1976-04-27

HU168838B
(en)

1976-07-28

Información de contacto