FR2410648A1 - NEW 15-DESOXY-16-VINYL- AND 16-CYCLOPROPYLPROSTAGLANDINS E ALKYL ESTERS, USEFUL IN PARTICULAR AS HYPOTENSORS, AND THEIR PREPARATION PROCESS - Google Patents

NEW 15-DESOXY-16-VINYL- AND 16-CYCLOPROPYLPROSTAGLANDINS E ALKYL ESTERS, USEFUL IN PARTICULAR AS HYPOTENSORS, AND THEIR PREPARATION PROCESS

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Publication number
FR2410648A1
FR2410648A1 FR7834250A FR7834250A FR2410648A1 FR 2410648 A1 FR2410648 A1 FR 2410648A1 FR 7834250 A FR7834250 A FR 7834250A FR 7834250 A FR7834250 A FR 7834250A FR 2410648 A1 FR2410648 A1 FR 2410648A1
Authority
FR
France
Prior art keywords
bopi
hypotensors
vinyl
cyclopropylprostaglandins
desoxy
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.)
Granted
Application number
FR7834250A
Other languages
French (fr)
Other versions
FR2410648B1 (en
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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
Priority claimed from US05/857,715 external-priority patent/US4198521A/en
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of FR2410648A1 publication Critical patent/FR2410648A1/en
Application granted granted Critical
Publication of FR2410648B1 publication Critical patent/FR2410648B1/fr
Granted legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
    • C07C45/305—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation with halogenochromate reagents, e.g. pyridinium chlorochromate
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/203—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/227—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/29—Saturated compounds containing keto groups bound to rings
    • C07C49/293—Saturated compounds containing keto groups bound to rings to a three- or four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1896—Compounds having one or more Si-O-acyl linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/22—Tin compounds
    • C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/09—Geometrical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

LES MEDICAMENTS SELON L'INVENTION SONT DES PROSTAGLANDINES E OPTIQUEMENT ACTIVES DE FORMULE GENERALE: (CF DESSIN DANS BOPI) (CF DESSIN DANS BOPI) OU SON IMAGE SPECULAIRE ET LES MELANGES RACEMIQUES, DANS LAQUELLE R EST UN GROUPE METHYLE OU ETHYLE, R EST UN GROUPE ALKYLE EN C-C, T EST UN RADICAL DIVALENT DE FORMULE: (CF DESSIN DANS BOPI) (CF DESSIN DANS BOPI) DANS LAQUELLE R EST UN GROUPE VINYLE OU CYCLOPROPYLE, Z EST UN GROUPE -CH- OU CIS-CH-CHCH-(CH)-, C-C REPRESENTE UN GROUPE ETHYLENE OU TRANSVINYLENE. APPLICATIONS: AGENTS HYPOTENSEURS, BRONCHODILATATEURS, ANTI-INFLAMMATOIRES ET DIVERSES APPLICATIONS DES PROSTAGLANDINES.THE MEDICINAL PRODUCTS ACCORDING TO THE INVENTION ARE OPTICALLY ACTIVE PROSTAGLANDINS E OF THE GENERAL FORMULA: (CF DRAWING IN BOPI) (CF DRAWING IN BOPI) OR ITS SPECULAR IMAGE AND RACEMIC MIXTURES, IN WHICH R IS A METHYL OR ETHYL GROUP, R IS A ALKYL GROUP IN CC, T IS A RADICAL DIVALENT WITH THE FORMULA: (CF DRAWING IN BOPI) (CF DRAWING IN BOPI) IN WHICH R IS A VINYL OR CYCLOPROPYL GROUP, Z IS A -CH- OR CIS-CH-CHCH- ( CH) -, CC REPRESENTS AN ETHYLENE OR TRANSVINYLENE GROUP. APPLICATIONS: HYPOTENSORS, BRONCHODILATORS, ANTI-INFLAMMATORY AGENTS AND VARIOUS APPLICATIONS OF PROSTAGLANDINS.

FR7834250A 1977-12-05 1978-12-05 NEW 15-DESOXY-16-VINYL- AND 16-CYCLOPROPYLPROSTAGLANDINS E ALKYL ESTERS, USEFUL IN PARTICULAR AS HYPOTENSORS, AND THEIR PREPARATION PROCESS Granted FR2410648A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US05/857,715 US4198521A (en) 1976-07-19 1977-12-05 15-Deoxy-16-hydroxy-16-vinyl and cyclopropyl substituted prostanoic acids and congeners
US88818378A 1978-03-20 1978-03-20

Publications (2)

Publication Number Publication Date
FR2410648A1 true FR2410648A1 (en) 1979-06-29
FR2410648B1 FR2410648B1 (en) 1983-09-23

Family

ID=27127420

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7834250A Granted FR2410648A1 (en) 1977-12-05 1978-12-05 NEW 15-DESOXY-16-VINYL- AND 16-CYCLOPROPYLPROSTAGLANDINS E ALKYL ESTERS, USEFUL IN PARTICULAR AS HYPOTENSORS, AND THEIR PREPARATION PROCESS

Country Status (5)

Country Link
AU (1) AU529836B2 (en)
DK (1) DK548578A (en)
ES (1) ES475787A1 (en)
FR (1) FR2410648A1 (en)
GB (1) GB2009173A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2385696A2 (en) * 1977-03-30 1978-10-27 American Cyanamid Co 15-Desoxy-16-hydroxy-prostaglandin analogues - useful as hypotensives, antiulcer agents etc., more selective than natural cpds.

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2274289A1 (en) * 1974-03-26 1976-01-09 Searle & Co NEW DERIVATIVES OF OXY-16 PROSTANOIC ACID, THEIR PREPARATION PROCESS AND THEIR THERAPEUTIC USE
JPS5283638A (en) * 1976-01-01 1977-07-12 Yamanouchi Pharmaceut Co Ltd Novel 15-cycloalkylprostadienoic acid derivatives
FR2359127A1 (en) * 1976-07-19 1978-02-17 American Cyanamid Co NEW 15-DESOXY-16-HYDROXYPROSTANOIC ACIDS 16-SUBSTITUTES WITH PHARMACEUTICAL ACTIVITIES AND THEIR PROCESS FOR PREPARATION
FR2385696A2 (en) * 1977-03-30 1978-10-27 American Cyanamid Co 15-Desoxy-16-hydroxy-prostaglandin analogues - useful as hypotensives, antiulcer agents etc., more selective than natural cpds.

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2274289A1 (en) * 1974-03-26 1976-01-09 Searle & Co NEW DERIVATIVES OF OXY-16 PROSTANOIC ACID, THEIR PREPARATION PROCESS AND THEIR THERAPEUTIC USE
JPS5283638A (en) * 1976-01-01 1977-07-12 Yamanouchi Pharmaceut Co Ltd Novel 15-cycloalkylprostadienoic acid derivatives
FR2359127A1 (en) * 1976-07-19 1978-02-17 American Cyanamid Co NEW 15-DESOXY-16-HYDROXYPROSTANOIC ACIDS 16-SUBSTITUTES WITH PHARMACEUTICAL ACTIVITIES AND THEIR PROCESS FOR PREPARATION
FR2385696A2 (en) * 1977-03-30 1978-10-27 American Cyanamid Co 15-Desoxy-16-hydroxy-prostaglandin analogues - useful as hypotensives, antiulcer agents etc., more selective than natural cpds.

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CA1977 *
EXBK/78 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2385696A2 (en) * 1977-03-30 1978-10-27 American Cyanamid Co 15-Desoxy-16-hydroxy-prostaglandin analogues - useful as hypotensives, antiulcer agents etc., more selective than natural cpds.

Also Published As

Publication number Publication date
DK548578A (en) 1979-06-06
GB2009173A (en) 1979-06-13
AU529836B2 (en) 1983-06-23
FR2410648B1 (en) 1983-09-23
AU4169778A (en) 1979-06-14
ES475787A1 (en) 1980-02-01

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