GB1269658A - Improvements in or relating to prostaglandins and the manufacture thereof - Google Patents
Improvements in or relating to prostaglandins and the manufacture thereofInfo
- Publication number
- GB1269658A GB1269658A GB712571A GB712571A GB1269658A GB 1269658 A GB1269658 A GB 1269658A GB 712571 A GB712571 A GB 712571A GB 712571 A GB712571 A GB 712571A GB 1269658 A GB1269658 A GB 1269658A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- substituted
- atoms
- fluorine atoms
- dimethylprostaglandin
- 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
- 150000003180 prostaglandins Chemical class 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- -1 3,3-difluorobutyl Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000001153 fluoro group Chemical group F* 0.000 abstract 3
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- 101000692460 Bos taurus Prostaglandin F synthase 1 Proteins 0.000 abstract 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 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
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000002997 prostaglandinlike Effects 0.000 abstract 1
- 150000003839 salts Chemical class 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
1,269,658. Prostaglandin derivatives. UPJOHN CO. 22 July, 1969 [29 July, 1968 (4)], No. 7125/71. Divided out of 1,269,656. Heading C2C. The invention comprises a process for preparing prostaglandin derivatives of the formula wherein R 1 is H, C 1-8 alkyl, C 3-10 cycloalkyl, C 7-12 aralkyl, phenyl, phenyl substituted with 1 to 3 chlorine atoms or C 1-4 alkyl, or ethyl substituted in the beta position with 3 chlorine atoms, 2 or 3 bromine atoms or 1, 2, or 3 iodine atoms; R 2 is H or C 1-8 alkyl, substituted with 0 to 3 fluorine atoms; R 3 and R 4 are H or C 1-4 alkyl; C n H 2n is C 1-8 alkylene, substituted with 0 to 2 fluorine atoms; and # indicates the attachment of OH and C n H 2n COOR 1 moieties to the ring in alpha or beta configuration, but excluding PGlF 2 and PGF 1# and their salts and esters by reacting carbonyl reducing agents with compounds of the formula and the novel compounds of the formulµ wherein m is 1 to 6, p is 0 to 7, n is 1 to 8, a is 0 to 4, R 13 is H, C 1-4 alkyl or a pharmacologically acceptable cation, Z is ethylene substituted by 1 or 2 fluorine atoms, and Y is 3,3-difluorobutyl, 4,4 - difluorobutyl, or 4,4,4-trifluorobutyl, obtained by the above process. Pharmaceutical compositions. suitable for oral, rectal or parenteral administration and having prostaglandin-like activity, contain the above novel compounds together with pharmaceutically acceptable carriers. 2,2 Dimethylprostaglandin F 1# and 2,2-dimethylprostaglandin F 1α are obtained by hydrolysing the corresponding methyl esters.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US74815868A | 1968-07-29 | 1968-07-29 | |
| US74991768A | 1968-07-29 | 1968-07-29 | |
| US74816768A | 1968-07-29 | 1968-07-29 | |
| US74816968A | 1968-07-29 | 1968-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1269658A true GB1269658A (en) | 1972-04-06 |
Family
ID=27505643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB712571A Expired GB1269658A (en) | 1968-07-29 | 1969-07-22 | Improvements in or relating to prostaglandins and the manufacture thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1269658A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7192940B2 (en) | 1999-04-01 | 2007-03-20 | Esperion Therapeutics, Inc. | Ether compounds |
-
1969
- 1969-07-22 GB GB712571A patent/GB1269658A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7192940B2 (en) | 1999-04-01 | 2007-03-20 | Esperion Therapeutics, Inc. | Ether compounds |
| US7709515B2 (en) | 1999-04-01 | 2010-05-04 | Esperion Therapeutics, Inc. | Compositions comprising ether compounds and pharmaceutical uses therefor |
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