GB1097533A - Prostanoic acid derivatives - Google Patents
Prostanoic acid derivativesInfo
- Publication number
- GB1097533A GB1097533A GB3233866A GB3233866A GB1097533A GB 1097533 A GB1097533 A GB 1097533A GB 3233866 A GB3233866 A GB 3233866A GB 3233866 A GB3233866 A GB 3233866A GB 1097533 A GB1097533 A GB 1097533A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- trans
- cis
- acyloxy
- hydrogen
- Prior art date
- 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
Links
- WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 10
- 125000001589 carboacyl group Chemical group 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 230000010933 acylation Effects 0.000 abstract 2
- 238000005917 acylation reaction Methods 0.000 abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 206010020772 Hypertension Diseases 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 abstract 1
- 229910000071 diazene Inorganic materials 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 230000002541 vasodepressive effect Effects 0.000 abstract 1
Classifications
-
- 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
Abstract
Novel compounds of the formulae <FORM:1097533/C2/1> <FORM:1097533/C2/2> <FORM:1097533/C2/3> <FORM:1097533/C2/4> wherein in Formulae II and VII, X, Y and are -(CH2)-; or X is trans -CH = CH- and Y and Z are -(CH2)2- (these compounds are not claimed in the present Specification, but 15 - hydroxy - 9 - oxoprosta - 10,trans - 13-dienoic acid and salts thereof are claimed in Specification 1,097,157); or X is trans-CH=CH-Y is cis-CH = CH- and Z is -(CH2)2- or cis-CH = CH-; in Formula VI and VIII X is -(CH2)2- or trans -CH = CH-; R1 is hydrogen, hydrocarbyl or a pharmaceutically acceptable cation; R2 is hydrogen or carboxylic acyl; and R4 is hydrogen or carboxylic acyl; but if R4 is carboxylic acyl, R2 is carboxylic acyl; are prepared by (1) for compounds II, dehydration of the corresponding 10,11-saturated-11a - hydroxy or - acyloxy - compounds with a carboxylic acid; (2) for compounds VI, by catalytic hydrogenation of the corresponding 10,11-saturated compounds; (3) for the 9-ol compounds VII and VIII by complex hydride reduction of the corresponding 9-ones; (4) for compounds II wherein X, Y and Z are all -(CH2)2-, by mixing diimide with the corresponding compounds wherein X is trans -CH = CH-, and Y and Z are both -(CH2)2-or both cis-CH = CH-, or Y is cis -CH = CH- and Z is -(CH2)2-; (5) for 15-acyloxy compounds, by acylation of 15-ols; (6) for 9-15-diacyloxy compounds, by acylation of 9,15 - diols or 9 - ol - 15 - acyloxy - compounds; and (7) for compounds wherein R1 is hydrocarbyl, by esterification of the free acids. Salts of the free acids with metals, ammonia and amines may be prepared. The novel prostanoic acid derivatives of the invention, which are stated to be vasodepressors valuable for treatment of hypertension, may be made up into pharmaceutical compositions with suitable carriers.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48010765A | 1965-08-16 | 1965-08-16 | |
| US52087666A | 1966-01-17 | 1966-01-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1097533A true GB1097533A (en) | 1968-01-03 |
Family
ID=27046471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3233866A Expired GB1097533A (en) | 1965-08-16 | 1966-07-19 | Prostanoic acid derivatives |
Country Status (12)
| Country | Link |
|---|---|
| BE (1) | BE685516A (en) |
| BR (1) | BR6681957D0 (en) |
| CH (2) | CH475936A (en) |
| DE (1) | DE1593644B2 (en) |
| FI (1) | FI49712C (en) |
| FR (2) | FR6042M (en) |
| GB (1) | GB1097533A (en) |
| IL (1) | IL26275A (en) |
| MY (1) | MY7100115A (en) |
| NL (3) | NL6611478A (en) |
| NO (1) | NO123281B (en) |
| SE (2) | SE369597B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3671570A (en) * | 1970-07-30 | 1972-06-20 | Ayerst Mckenna & Harrison | Derivatives of 9-oxo-15-hydroxyprostanoic acid, homologs thereof and their preparation |
-
1966
- 1966-07-19 GB GB3233866A patent/GB1097533A/en not_active Expired
- 1966-07-22 CH CH1065166A patent/CH475936A/en not_active IP Right Cessation
- 1966-07-22 CH CH430469A patent/CH479522A/en not_active IP Right Cessation
- 1966-08-05 IL IL2627566A patent/IL26275A/en unknown
- 1966-08-08 BR BR18195766A patent/BR6681957D0/en unknown
- 1966-08-09 DE DE19661593644 patent/DE1593644B2/en active Granted
- 1966-08-15 SE SE1154170A patent/SE369597B/xx unknown
- 1966-08-15 SE SE1102766A patent/SE350253B/xx unknown
- 1966-08-15 NO NO16430266A patent/NO123281B/no unknown
- 1966-08-16 BE BE685516D patent/BE685516A/xx unknown
- 1966-08-16 FI FI214166A patent/FI49712C/en active
- 1966-08-16 NL NL6611478A patent/NL6611478A/xx unknown
- 1966-11-10 FR FR83374A patent/FR6042M/fr not_active Expired
- 1966-11-10 FR FR83373A patent/FR6017M/fr not_active Expired
-
1971
- 1971-12-31 MY MY7100115A patent/MY7100115A/en unknown
-
1977
- 1977-03-16 NL NL7702818A patent/NL7702818A/en not_active Application Discontinuation
- 1977-03-16 NL NL7702819A patent/NL7702819A/en not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3671570A (en) * | 1970-07-30 | 1972-06-20 | Ayerst Mckenna & Harrison | Derivatives of 9-oxo-15-hydroxyprostanoic acid, homologs thereof and their preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| FI49712C (en) | 1975-09-10 |
| DE1793690A1 (en) | 1972-10-26 |
| BR6681957D0 (en) | 1973-10-25 |
| SE350253B (en) | 1972-10-23 |
| NL7702818A (en) | 1977-06-30 |
| FI49712B (en) | 1975-06-02 |
| BE685516A (en) | 1967-02-16 |
| IL26275A (en) | 1970-08-19 |
| NO123281B (en) | 1971-10-25 |
| DE1593644A1 (en) | 1972-07-27 |
| CH479522A (en) | 1969-10-15 |
| DE1593644C3 (en) | 1974-03-14 |
| FR6042M (en) | 1968-05-20 |
| DE1593644B2 (en) | 1973-08-09 |
| SE369597B (en) | 1974-09-09 |
| NL6611478A (en) | 1967-02-17 |
| CH475936A (en) | 1969-07-31 |
| DE1793690B2 (en) | 1976-04-22 |
| FR6017M (en) | 1968-05-06 |
| MY7100115A (en) | 1971-12-31 |
| NL7702819A (en) | 1977-06-30 |
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