C.sub.14 Phenyl-substituted derivatives of prostaglandin analogues
US4149007A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Jun 24, 1977 |
| Grant date | Apr 10, 1979 |
| Priority date | — |
| Expiry date | Jun 24, 1997 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07F1/08
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Analogues of prostaglandins A, E and F in which a phenyl moiety is attached to the C.sub.14 carbon atom are disclosed. Also disclosed are methods of preparing the analogues and starting materials. The compounds have the structural formula: ##STR1## in which J is methylene, R or S-hydroxymethylene or methine; L is methylene or methine and can be methine only when J is methine; M is carbonyl, R or S-hydroxymethylene; Q is ethylene, Z-vinylene or inter-phenylene; T is an alkoxy-carbonyl having from 2 to 3 carbon atoms inclusive, or carboxyl; and B is a loweralkyl of from 1 to 5 carbon atoms. The prostaglandin analogues of the present invention exhibit a separation of pharmacological activity. The analogues can be used for platelet aggregation (and Methyl 14-Phenyl-11.alpha.,15S-dihydroxy-9-oxoprost-13E-en-1-oate can be used for antagonism for smooth muscle stimulation) without the accompanying undesirable side effects of natural prostaglandins, e.g., flush, headache, abdominal cramps and nausea.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.