GB1386870A - Prostaglandins and the preparation thereof - Google Patents
Prostaglandins and the preparation thereofInfo
- Publication number
- GB1386870A GB1386870A GB717172A GB717172A GB1386870A GB 1386870 A GB1386870 A GB 1386870A GB 717172 A GB717172 A GB 717172A GB 717172 A GB717172 A GB 717172A GB 1386870 A GB1386870 A GB 1386870A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- pge
- ethyl
- alkyl
- compounds
- 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 2
- 150000003180 prostaglandins Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 4
- MNWFXJYAOYHMED-UHFFFAOYSA-N hexane carboxylic acid Natural products CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 abstract 3
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 abstract 2
- RQOFITYRYPQNLL-ZWSAOQBFSA-N 16,16-dimethyl-PGE1 Chemical compound CCCCC(C)(C)[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O RQOFITYRYPQNLL-ZWSAOQBFSA-N 0.000 abstract 1
- 101000692460 Bos taurus Prostaglandin F synthase 1 Proteins 0.000 abstract 1
- IQSNJEUPWVWFFR-UHFFFAOYSA-N CC(C=C/C1C2CC(CC12)=O)CCCC Chemical compound CC(C=C/C1C2CC(CC12)=O)CCCC IQSNJEUPWVWFFR-UHFFFAOYSA-N 0.000 abstract 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1386870 Prostaglandins UPJOHN CO 16 Feb 1972 [11 March 1971] 7171/72 Heading C2C [Also in Divisions C3 and A5] The invention comprises optically active compounds of the formulae or racemates thereof, wherein R 1 is H or C 1-8 alkyl, and R 2 and R 3 are H, methyl or ethyl, provided that at least one of R 2 and R 3 is not H, and pharmacologically acceptable salts thereof and their preparation. The 16-alkyl and 16,16-dialkyl PGF 1# compounds are obtained by reducing the corresponding 16-alkyl and 66,16-dialkyl PGE 1 compounds and separating the 9# hydroxy isomer and the 16-alkyl and 16,16-dialkyl PGA 1 and PGB 1 compounds are prepared by dehydrating the corresponding 16-alkyl and 16,16-dialkyl PGE 1 compounds, followed by, if desired, hydrolysis of any resulting esters or esterification of any resulting acids. The following intermediates and starting materials are prepared: 6 - (3 - methyl - cis - 1 - heptenyl)bicyclo [3,1,0]hexan - 3 - one; 7 - [6 - (3 - methyl - cis- 1 - heptenyl) - 3 - oxo - bicyclo[3,1,0]hex - 2α- yl] - heptanoic acid and its methyl and 2,2,2-trichloroethyl esters; methyl 7-[6-(1,2- dihydroxy - 3 - methylheptyl) - 3 - oxobicyclo- [3,1,0]hex - 2α - yl] - heptanoate and its bis - (methane - sulphonate; 16-methyl-PGE 1 , 16,16-dimethyl-PGE 1 , 16-ethyl-PGE 1 , 16-ethyl 16-methyl-PGE 1 , and 16,16-diethyl-PGE 1 , and their methyl and 2,2,2-trichloroethyl esters; 7 - [3 - hydroxy - 6 - (3 - methyl - cis - 1-heptenyl)bicyclo[3,1,0)- hex - 2α - yl]heptanoic acid and its methyl ester; 7-{6-[3-methyl-(or 3,3- dimethyl-, or 3,3-diethyl-, or 3-ethyl-, or 3 - ethyl - 3 - methyl) - cis - 1 - heptenyl) - 3- oxobicyclo[3,1,0]hex-2α-yl}heptanoates.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12338871A | 1971-03-11 | 1971-03-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1386870A true GB1386870A (en) | 1975-03-12 |
Family
ID=22408408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB717172A Expired GB1386870A (en) | 1971-03-11 | 1972-02-16 | Prostaglandins and the preparation thereof |
Country Status (10)
| Country | Link |
|---|---|
| AU (1) | AU459678B2 (en) |
| BE (1) | BE780522A (en) |
| CA (1) | CA927836A (en) |
| CH (3) | CH568974A5 (en) |
| DE (1) | DE2210697A1 (en) |
| FR (1) | FR2128836B1 (en) |
| GB (1) | GB1386870A (en) |
| NL (1) | NL7203126A (en) |
| NO (1) | NO134297C (en) |
| ZA (1) | ZA72646B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3965143A (en) * | 1974-03-26 | 1976-06-22 | G. D. Searle & Co. | 16-Oxygenated prostanoic acid derivatives |
-
1972
- 1972-02-01 ZA ZA720646A patent/ZA72646B/en unknown
- 1972-02-01 CA CA133671A patent/CA927836A/en not_active Expired
- 1972-02-07 AU AU38725/72A patent/AU459678B2/en not_active Expired
- 1972-02-16 GB GB717172A patent/GB1386870A/en not_active Expired
- 1972-03-06 DE DE2210697A patent/DE2210697A1/en active Pending
- 1972-03-08 CH CH910775A patent/CH568974A5/xx not_active IP Right Cessation
- 1972-03-08 CH CH340672A patent/CH568973A5/xx not_active IP Right Cessation
- 1972-03-08 CH CH910875A patent/CH575920A5/xx not_active IP Right Cessation
- 1972-03-09 NL NL7203126A patent/NL7203126A/xx not_active Application Discontinuation
- 1972-03-10 BE BE780522A patent/BE780522A/en not_active IP Right Cessation
- 1972-03-10 FR FR7208467A patent/FR2128836B1/fr not_active Expired
- 1972-03-10 NO NO72771A patent/NO134297C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU3872572A (en) | 1973-08-09 |
| ZA72646B (en) | 1973-09-26 |
| CH568973A5 (en) | 1975-11-14 |
| CA927836A (en) | 1973-06-05 |
| NO134297B (en) | 1976-06-08 |
| NO134297C (en) | 1976-09-15 |
| NL7203126A (en) | 1972-09-13 |
| FR2128836B1 (en) | 1975-08-01 |
| FR2128836A1 (en) | 1972-10-20 |
| AU459678B2 (en) | 1975-03-13 |
| CH575920A5 (en) | 1976-05-31 |
| CH568974A5 (en) | 1975-11-14 |
| DE2210697A1 (en) | 1973-10-25 |
| BE780522A (en) | 1972-09-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |