GB1495152A - Prostanoic acid derivatives - Google Patents

Prostanoic acid derivatives

Info

Publication number
GB1495152A
GB1495152A GB36165/74A GB3616574A GB1495152A GB 1495152 A GB1495152 A GB 1495152A GB 36165/74 A GB36165/74 A GB 36165/74A GB 3616574 A GB3616574 A GB 3616574A GB 1495152 A GB1495152 A GB 1495152A
Authority
GB
United Kingdom
Prior art keywords
methyl
compounds
tetrahydropyran
trans
hydroxy
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
Application number
GB36165/74A
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries 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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB36165/74A priority Critical patent/GB1495152A/en
Priority to ZA00754492A priority patent/ZA754492B/en
Priority to AU83240/75A priority patent/AU8324075A/en
Priority to NL7509626A priority patent/NL7509626A/en
Priority to SE7509129A priority patent/SE7509129L/en
Priority to BE159250A priority patent/BE832479A/en
Priority to FR7525444A priority patent/FR2281748A1/en
Priority to JP50099415A priority patent/JPS5143744A/en
Priority to HU75IE707A priority patent/HU173223B/en
Priority to DE19752536754 priority patent/DE2536754A1/en
Priority to DD187920A priority patent/DD121102A5/xx
Publication of GB1495152A publication Critical patent/GB1495152A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
    • C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
    • 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
    • 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
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1495152 17-Oxaprostaglandins IMPERIAL CHEMICAL INDUSTRIES Ltd 3 July 1975 [16 Aug 1974] 36165/74 Headings C2C and C2P [Also in Division C3] The invention comprises 17-oxaprostaglandins of the formula wherein R<SP>1</SP> is carboxy or (C 1-10 alkoxy) carbonyl, Y is ethylene or cis-vinylene, R<SP>5</SP> and R<SP>6</SP> each are C 1-4 alkyl, and R<SP>7</SP> is C 1-10 alkyl, and for those compounds wherein R<SP>1</SP> is carboxy, the pharmaceutically or veterinarily acceptable salts thereof and their preparation. The compounds are prepared either by the acidic hydrolysis of compounds of the Formula III wherein R<SP>8</SP> is tetrahydropyran-2-yl or trialkylsilyl, followed by, if desired, esterification, or by the selective oxidation of compounds of the Formula IV The following intermediates are also prepared: compounds of Formula III above in which R<SP>8</SP> is tetrahydropyran-2-yl, Y is cisvinylene, R<SP>5</SP> and R<SP>6</SP> are both methyl and R<SP>7</SP> is propyl or pentyl; 9α-hydroxy-16,16-dimethyl- 17-oxa-11α,15-bis(tetrahydropyran-2-yloxy)-5- cis, 13-trans-prostadrenoic acid, 20-ethyl-9α- hydroxy - 16,16 - dimethyl - 17 - oxa - 11α,15- bis(tetrahydropyran - 2 - yloxy) - 5 - cis, 13- trans-prostadienoic acid, 4#-[4-methyl-4-propoxy (and pentyloxy)-3-(tetrahydropyran-2- yloxy)-1-trans-pentenyl)-5α-(t-etrahydropyran- 2 - yloxy) - 3,3α#,4,5,6,6α# - hexahydro - 2H- cyclopenta[b]furan - 2 - one (and 2 - ol), 4#-[4- methyl-4-propoxy (and pentyloxy)-3-hydroxy- 1 - trans - pentenyl) - 5α - hydroxy - 3,3α#,4,5,6- 6α# - hexahydro - 2H - cyolopenta[b]furan - 2 - one and 4#-[4-methyl-4-propoxy (and pentyloxy) - 3 - hydroxy (and oxo) - 1 - trans - pentenyl) - 5α - (4 - phenylbenzoyloxy) - 3,3α#,4,5- 6,6α# - hexahydro - 2H - cyclopenta[b]furan-2- one. Dimethyl 3-methyl-2-oxo-3-propoxybutylphosphonate and dimethyl 3-methyl-2-oxo-3-pentyloxybutyl phosphonate are prepared by reacting dimethyl methylphosphonate in the presence of butyl-lithium with methyl 2-methyl-2-propoxypropionate and methyl 2-methyl-2-pentyloxypropionate respectively. Pharmaceutical compositions, suitable for oral administration, contain the above 17-oxaprostaglandins or salts thereof together with pharmaceutically or veterinarily acceptable carriers or diluents. The compounds inhibit gastric acid secretion in warm blooded animals.
GB36165/74A 1974-08-16 1974-08-16 Prostanoic acid derivatives Expired GB1495152A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
GB36165/74A GB1495152A (en) 1974-08-16 1974-08-16 Prostanoic acid derivatives
ZA00754492A ZA754492B (en) 1974-08-16 1975-07-14 Prostanoic acid derivatives
AU83240/75A AU8324075A (en) 1974-08-16 1975-07-21 Prostanoic acid derivatives
NL7509626A NL7509626A (en) 1974-08-16 1975-08-13 PROCESS FOR PREPARING NEW PROSTANIC ACID DERIVATIVES AND PROCESS FOR PREPARING THE NEW COMPOUNDS CONTAINING.
SE7509129A SE7509129L (en) 1974-08-16 1975-08-14 PROSTANIC ACID DERIVATIVES AND METHOD OF THEIR PREPARATION.
BE159250A BE832479A (en) 1974-08-16 1975-08-14 PROSTANOIC ACID DERIVATIVES
FR7525444A FR2281748A1 (en) 1974-08-16 1975-08-14 PROSTANOIC ACID DERIVATIVES
JP50099415A JPS5143744A (en) 1974-08-16 1975-08-15 177 okisapurosutansanjudotaino seiho
HU75IE707A HU173223B (en) 1974-08-16 1975-08-15 Process for preparing derivatives of 9-oxo-17-oxa-prostanic acid
DE19752536754 DE2536754A1 (en) 1974-08-16 1975-08-18 PROSTANIC ACID DERIVATIVES
DD187920A DD121102A5 (en) 1974-08-16 1975-08-18

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB36165/74A GB1495152A (en) 1974-08-16 1974-08-16 Prostanoic acid derivatives

Publications (1)

Publication Number Publication Date
GB1495152A true GB1495152A (en) 1977-12-14

Family

ID=10385572

Family Applications (1)

Application Number Title Priority Date Filing Date
GB36165/74A Expired GB1495152A (en) 1974-08-16 1974-08-16 Prostanoic acid derivatives

Country Status (11)

Country Link
JP (1) JPS5143744A (en)
AU (1) AU8324075A (en)
BE (1) BE832479A (en)
DD (1) DD121102A5 (en)
DE (1) DE2536754A1 (en)
FR (1) FR2281748A1 (en)
GB (1) GB1495152A (en)
HU (1) HU173223B (en)
NL (1) NL7509626A (en)
SE (1) SE7509129L (en)
ZA (1) ZA754492B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2453850A1 (en) * 1979-04-10 1980-11-07 Lepetit Spa NOVEL 16-METHOXY-16-METHYL-PROSTAGLANDIN E1 DERIVATIVES USEFUL IN PARTICULAR AS GASTROPROTECTIVE AGENTS AND THEIR PREPARATION PROCESS

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2967236D1 (en) * 1979-07-17 1984-10-31 Pfizer N-ALKANESULFONYL 16,16-DIMETHYL-17-OXAPROSTAGLANDIN CARBOXAMIDES

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2453850A1 (en) * 1979-04-10 1980-11-07 Lepetit Spa NOVEL 16-METHOXY-16-METHYL-PROSTAGLANDIN E1 DERIVATIVES USEFUL IN PARTICULAR AS GASTROPROTECTIVE AGENTS AND THEIR PREPARATION PROCESS
FR2510567A1 (en) * 1979-04-10 1983-02-04 Lepetit Spa OPTICAL ISOMERATE OF METHYL 11A, 15-DIHYDROXY 16-METHOXY-16-METHYL-PROSTA 13 (E) -ENE-1-OATE, PARTICULARLY USEFUL AS A GASTROPROTECTIVE AGENT AND PROCESS FOR PREPARING THE SAME

Also Published As

Publication number Publication date
NL7509626A (en) 1976-02-18
DD121102A5 (en) 1976-07-12
ZA754492B (en) 1976-06-30
FR2281748A1 (en) 1976-03-12
DE2536754A1 (en) 1976-04-01
JPS5143744A (en) 1976-04-14
BE832479A (en) 1976-02-16
SE7509129L (en) 1976-02-17
AU8324075A (en) 1977-01-27
HU173223B (en) 1979-03-28
FR2281748B1 (en) 1978-11-10

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Legal Events

Date Code Title Description
PS Patent sealed
48R Reference inserted (sect. 8/1949)
SP Amendment (slips) printed
PCNP Patent ceased through non-payment of renewal fee