FR2408587A1 - 11-Deoxy-10-hydroxy-prostaglandin=e-1 derivs. prepn. - by reacting cyclopentenyl-alkanoic acid derivs. with 1-alkenyl lithium cpds. in presence of copper cpds. - Google Patents

11-Deoxy-10-hydroxy-prostaglandin=e-1 derivs. prepn. - by reacting cyclopentenyl-alkanoic acid derivs. with 1-alkenyl lithium cpds. in presence of copper cpds.

Info

Publication number
FR2408587A1
FR2408587A1 FR7735157A FR7735157A FR2408587A1 FR 2408587 A1 FR2408587 A1 FR 2408587A1 FR 7735157 A FR7735157 A FR 7735157A FR 7735157 A FR7735157 A FR 7735157A FR 2408587 A1 FR2408587 A1 FR 2408587A1
Authority
FR
France
Prior art keywords
cpds
formula
derivs
cpd
xiv
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.)
Pending
Application number
FR7735157A
Other languages
French (fr)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
May and Baker Ltd
Original Assignee
May and Baker Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by May and Baker Ltd filed Critical May and Baker Ltd
Publication of FR2408587A1 publication Critical patent/FR2408587A1/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

In the prepn. of cyclopentane derivs. of formula (II) (where R2 is 1-12C alkyl; R2 and R3 are H or 1-4C alkyl; R4 is H or 1-10C alkyl; and n is 4,5,6,7 or a cpd. of formula (III) (where R6 is a suitable acid labile protecting group is reacted with a soln. of a cpd. of formula L-CH=CH-CH - (OR6)-CR2R3R4) (VI) in the presence of a copper cpd. so as to give a cpd. of formula (VII) (in which the residues R6 may be identical or different) and this is hydrolysed in moderately acidic medium to give (II). New use of cpds. of formula (II) is in the prepn. of cpds. of formula (XIV) by hydrolysing them with yeast (esp. baker's yeast) in aq. medium, the product of formula (XIV) opt. being converted into a salt. Specifically claimed (I) are (plus-or-minus)-(10R and S, 15S)-11-dexoxy-10-hydroxy-prostaglandin E1 methyl ester (IIb). A specifically claimed cpd. (XIV) is (plus-or-minus)-(10R and S, 15S)-11-deoxy-10-hydroxy-prostaglandin E1 (XIVa). (II), (XIV) and salts of (XIV) are hypotensives, bronchodilators, gastric acid secretion inhibitors, uterine contraction stimulants, and CNS depressants.
FR7735157A 1976-11-24 1977-11-23 11-Deoxy-10-hydroxy-prostaglandin=e-1 derivs. prepn. - by reacting cyclopentenyl-alkanoic acid derivs. with 1-alkenyl lithium cpds. in presence of copper cpds. Pending FR2408587A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4908976 1976-11-24

Publications (1)

Publication Number Publication Date
FR2408587A1 true FR2408587A1 (en) 1979-06-08

Family

ID=10451103

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7735157A Pending FR2408587A1 (en) 1976-11-24 1977-11-23 11-Deoxy-10-hydroxy-prostaglandin=e-1 derivs. prepn. - by reacting cyclopentenyl-alkanoic acid derivs. with 1-alkenyl lithium cpds. in presence of copper cpds.

Country Status (3)

Country Link
JP (1) JPS5365854A (en)
DE (1) DE2752523A1 (en)
FR (1) FR2408587A1 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7169807B2 (en) 2004-04-09 2007-01-30 Allergan, Inc. 10-Hydroxy-11-dihydroprostaglandin analogs as selective EP4 agonists
US7893107B2 (en) 2005-11-30 2011-02-22 Allergan, Inc. Therapeutic methods using prostaglandin EP4 agonist components

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2162213A1 (en) * 1971-12-03 1973-07-13 Syntex Corp
FR2162212A1 (en) * 1971-12-03 1973-07-13 Syntex Corp
FR2195431A1 (en) * 1972-02-18 1974-03-08 May & Baker Ltd

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2162213A1 (en) * 1971-12-03 1973-07-13 Syntex Corp
FR2162212A1 (en) * 1971-12-03 1973-07-13 Syntex Corp
FR2195431A1 (en) * 1972-02-18 1974-03-08 May & Baker Ltd

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
EXBK/72 *

Also Published As

Publication number Publication date
DE2752523A1 (en) 1978-06-01
JPS5365854A (en) 1978-06-12

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