GB1156465A - Prostaglandins - Google Patents
ProstaglandinsInfo
- Publication number
- GB1156465A GB1156465A GB749567A GB749567A GB1156465A GB 1156465 A GB1156465 A GB 1156465A GB 749567 A GB749567 A GB 749567A GB 749567 A GB749567 A GB 749567A GB 1156465 A GB1156465 A GB 1156465A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acids
- prostaglandins
- prepared
- salts
- esters
- 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
- 229940094443 oxytocics prostaglandins Drugs 0.000 title abstract 5
- 150000003180 prostaglandins Chemical class 0.000 title abstract 4
- 239000002253 acid Substances 0.000 abstract 7
- 150000007513 acids Chemical class 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 3
- NLRIJHGYFNZMGB-UHFFFAOYSA-N 8-nonynoic acid Chemical compound OC(=O)CCCCCCC#C NLRIJHGYFNZMGB-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 abstract 2
- ZYJDXFLOQUBABE-UHFFFAOYSA-N 1-bromodeca-2,5-diyne Chemical compound CCCCC#CCC#CCBr ZYJDXFLOQUBABE-UHFFFAOYSA-N 0.000 abstract 1
- PLBPPUBDYCUEGP-UHFFFAOYSA-N 1-bromododeca-2,5-diyne Chemical compound CCCCCCC#CCC#CCBr PLBPPUBDYCUEGP-UHFFFAOYSA-N 0.000 abstract 1
- -1 6 - carboxyhexyl Chemical group 0.000 abstract 1
- 238000006218 Arndt-Eistert homologation reaction Methods 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- 108010024636 Glutathione Proteins 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- 241001494479 Pecora Species 0.000 abstract 1
- 210000001772 blood platelet Anatomy 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 210000004907 gland Anatomy 0.000 abstract 1
- 229960003180 glutathione Drugs 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 238000011534 incubation Methods 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P31/00—Preparation of compounds containing a five-membered ring having two side-chains in ortho position to each other, and having at least one oxygen atom directly bound to the ring in ortho position to one of the side-chains, one side-chain containing, not directly bound 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 at least one oxygen atom bound in gamma-position to the ring, e.g. prostaglandins
-
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/36—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by hydrogenation of carbon-to-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/64—Acyl halides
- C07C57/66—Acyl halides with only carbon-to-carbon double bonds as unsaturation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,156,465. Prostaglandins. UNILEVER Ltd. 14 Feb., 1968 [16 Feb., 1967], No. 7495/67. Heading C2C. The novel prostaglandins 1α - (6 - carboxyhexyl) - 4α - hydroxy - cyclopentan - 2 - one having in the 5#-position a 3S-hydroxy-n-alklt-enyl group of 7 or 9 carbon atoms (alternatively named #-nor- and #-homo-prostaglandins E 1 ) and the novel salts and esters thereof are prepared by aerobic incubation of nonadeca- or heneicosa-8c,11c,14c-trienoic acid with a prostaglandin-synthesizing enzyme prepared from animal tissue, e.g. sheep vesicular gland, desirably in the presence of added glutathione. The required products can be isolated as the free acids and, if desired, converted into salts or esters of the carboxylic group. The free acid can be regenerated from its derivative if required. The starting acids can be prepared by selective partial hydrogenation from the corresponding triynoic acids (themselves prepared from non- 8-ynoic acid, ethyl magnesium bromide and 1 - bromo - deca - 2,5 - diyne or 1 - bromododeca-2,5-diyne) or by chain-lengthening of the corresponding trienoic acids of one carbon atom less by the Arndt-Eistert synthesis. Salts of these acids and their methyl esters are also described. The prostaglandins of the invention are stated to exhibit smooth muscle-contracting hypotensive, heart-stimulating and/or blood platelet aggregation-inhibiting activity, and they may be made up into pharmaceutical compositions with suitable carriers.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB749567A GB1156465A (en) | 1967-02-16 | 1967-02-16 | Prostaglandins |
| FR1560642D FR1560642A (en) | 1967-02-16 | 1968-02-15 | |
| BE710918D BE710918A (en) | 1967-02-16 | 1968-02-16 | |
| NL6802212A NL159375B (en) | 1967-02-16 | 1968-02-16 | PROCESS FOR PREPARING A PHARMACEUTICAL PREPARATION BASED ON AN E-SERIES PROSTAGLANDIN, FORMED PREPARATION, PREPARED ACCORDING TO THIS PROCESS, AND PROCESS FOR PREPARING PROSTAGLANDIN DERIVATIVES OF THE E-SERIES. |
| CH231868A CH527150A (en) | 1967-02-16 | 1968-02-16 | 3-hydroxy-cyclopentanone derivs |
| DE1968U0014673 DE1668809C3 (en) | 1967-02-16 | 1968-02-16 | Prostaglandin compounds, processes for their preparation and therapeutic agents containing them |
| FR151646A FR7885M (en) | 1967-02-16 | 1968-05-14 | |
| US05/343,269 US4163108A (en) | 1967-02-16 | 1973-03-21 | Prostaglandins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB749567A GB1156465A (en) | 1967-02-16 | 1967-02-16 | Prostaglandins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1156465A true GB1156465A (en) | 1969-06-25 |
Family
ID=9834220
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB749567A Expired GB1156465A (en) | 1967-02-16 | 1967-02-16 | Prostaglandins |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE710918A (en) |
| CH (1) | CH527150A (en) |
| DE (1) | DE1668809C3 (en) |
| FR (2) | FR1560642A (en) |
| GB (1) | GB1156465A (en) |
| NL (1) | NL159375B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017223447A1 (en) | 2016-06-23 | 2017-12-28 | The Regents Of The University Of Michigan | 12(s)-hydroxyeicosatrienoic acid compounds and their use as therapeutic agents |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5262437A (en) * | 1990-12-10 | 1993-11-16 | Allergan, Inc. | Homo-prostaglandin derivatives as ocular hypotensives |
| HUT64305A (en) * | 1990-12-10 | 1993-12-28 | Allergan Inc | Method for producing homo-prostagladine derivatives and pharmaceutical preparatives containing them |
| JPH10130196A (en) * | 1996-10-29 | 1998-05-19 | Toray Dow Corning Silicone Co Ltd | Production of fatty acid chloride |
-
1967
- 1967-02-16 GB GB749567A patent/GB1156465A/en not_active Expired
-
1968
- 1968-02-15 FR FR1560642D patent/FR1560642A/fr not_active Expired
- 1968-02-16 CH CH231868A patent/CH527150A/en not_active IP Right Cessation
- 1968-02-16 DE DE1968U0014673 patent/DE1668809C3/en not_active Expired
- 1968-02-16 NL NL6802212A patent/NL159375B/en unknown
- 1968-02-16 BE BE710918D patent/BE710918A/xx not_active IP Right Cessation
- 1968-05-14 FR FR151646A patent/FR7885M/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017223447A1 (en) | 2016-06-23 | 2017-12-28 | The Regents Of The University Of Michigan | 12(s)-hydroxyeicosatrienoic acid compounds and their use as therapeutic agents |
| EP3475442A4 (en) * | 2016-06-23 | 2019-12-04 | The Regents of The University of Michigan | 12(s)-hydroxyeicosatrienoic acid compounds and their use as therapeutic agents |
| US11111222B2 (en) | 2016-06-23 | 2021-09-07 | The Regents Of The University Of Michigan | Hydroxyeicosatrienoic acid compounds and their use as therapeutic agents |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1668809A1 (en) | 1971-09-30 |
| DE1668809C3 (en) | 1980-03-27 |
| FR1560642A (en) | 1969-03-21 |
| DE1668809B2 (en) | 1979-07-12 |
| NL159375B (en) | 1979-02-15 |
| CH527150A (en) | 1972-08-31 |
| BE710918A (en) | 1968-08-16 |
| FR7885M (en) | 1970-05-04 |
| NL6802212A (en) | 1968-08-19 |
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