Hetero-prostaglandin derivatives and processes for preparing them

• US 4,377,704 A
• Filed: 08/03/1981
• Issued: 03/22/1983
• Est. Priority Date: 08/12/1980
• Status: Expired due to Fees

• Current Assignee: Sanofi
• Original Assignee: Sanofi
• Inventors: Barriere, Jean-Claude, Cleophax, Jeanine, Gero, Stephan, Cier, Andre
• Primary Examiner(s): Gerstl, Robert
• Application Number:
  US06/289,391
• Time in Patent Office: 596 Days
• Field of Search: 260/340.9 P, 549/39, 568/442, 568/330, 568/379, 568/440, 544/374, 544/375
• US Class Current: 549/39
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07C 2601/10 the ring being unsaturated
• CPC Class Codes: C07C 405/00 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
• CPC Class Codes: C07C 405/0033 containing sulfur
• CPC Class Codes: C07C 43/196 containing hydroxy or O-metal groups
• CPC Class Codes: C07C 45/29 of hydroxy groups
• CPC Class Codes: C07C 45/60 in six-membered rings
• CPC Class Codes: C07C 45/66 by dehydration
• CPC Class Codes: C07C 47/277 containing ether groups, groups, groups, or groups
• CPC Class Codes: C07C 47/47 containing ether groups, groups, groups, or groups
• CPC Class Codes: C07D 319/06 not condensed with other rings
• CPC Class Codes: C07D 339/06 having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
• CPC Class Codes: C07D 409/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 495/10 Spiro-condensed systems

Abstract

Prostanoic acid derivatives represented by the general formula: ##STR1## in which X represents hydrogen or hydroxy, X₁ represents hydrogen or X and X₁, when they are taken together with the carbon atom to which they are attached, represent a carbonyl group and Z represents hydrogen or hydroxy and pharmaceutically acceptable alkali metal salts thereof.

They can be used as bronchodilators and/or inhibitors of blood-platelet aggregation.

Claims

1. A cyclopentene derivative represented by the formula:

##STR50## in which R represents a hydroxy-protecting group of the formula --CH₂ R₁ in which R₁ represents an phenyl or methylphenyl, B represents ##STR51## and A is such that;

when B represents ##STR52## A represents ##STR53## when B represents ##STR54## A represents ##STR55##

2. A cyclopentene derivative according to claim 1 wherein R₁ is phenyl.

3. 2-Formyl-4(R)-benzyloxy-2-cyclopentenoneethylenedithioacetal.

4. 2-Formylpropyleneacetal-4(R)-benzyloxy-2-cyclopentenone-ethylenedithioacetal.

5. 2-Formylpropyleneacetal-4(R)-benzyloxy-2-cyclopentenone.

6. 2-Formylpropyleneacetal-4(R)-benzyloxy-2-cyclopentenol.

7. 1-Formyl-3(R)-benzyloxy-1-cyclopentene.

8. 1-Formylpropyleneacetal-3(R)-benzyloxy-1-cyclopentene.