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GB1282663A - Bicyclo[3,1,0]hexan-3-one derivatives and the manufacture thereof - Google Patents

Bicyclo[3,1,0]hexan-3-one derivatives and the manufacture thereof

Info

Publication number
GB1282663A
GB1282663A GB5802771A GB5802771A GB1282663A GB 1282663 A GB1282663 A GB 1282663A GB 5802771 A GB5802771 A GB 5802771A GB 5802771 A GB5802771 A GB 5802771A GB 1282663 A GB1282663 A GB 1282663A
Authority
GB
United Kingdom
Prior art keywords
alkyl
compounds
formula
water
substituted
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
GB5802771A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn 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
Application filed by Upjohn Co filed Critical Upjohn Co
Priority to GB5802771A priority Critical patent/GB1282663A/en
Publication of GB1282663A publication Critical patent/GB1282663A/en
Expired 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
    • C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
    • C07C35/27—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system containing six carbon atoms
    • 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
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P31/00—Preparation of compounds containing a five-membered ring having two side-chains in ortho position to each other, and having at least one oxygen atom directly bound to the ring in ortho position to one of the side-chains, one side-chain containing, not directly bound 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 at least one oxygen atom bound in gamma-position to the ring, e.g. prostaglandins

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1282663 Bicyclo[3,1,0]hexan-3-one derivatives UPJOHN CO 10 March 1970 [14 March 1969] 58027/71 Divided out of 1282661 Heading C2C The invention comprises novel bicyclo[3,1,0]- hexan-3-one derivatives of the Formula I wherein R 1 is H, C 1-8 alkyl, C 3-10 cycloalkyl, phenyl, phenyl substituted with 1 to 3 chlorine atoms or C 1-4 alkyl-, or ethyl substituted in the #-position with 3 chlorine, 2 or 3 bromine or 1, 2, or 3 iodine atoms; R 2 is H or C 1-10 alkyl substituted with 0 to 3 fluorine atoms; R 3 and R 4 are H or C 1-4 alkyl; A is C 1-10 alkylene substituted with 0 to 2 fluorine atoms, and with 1 to 5 carbon atoms between COOR 1 and V; V is R 10 arid R 11 are H or C 1-5 alkyl sulphonyl, with the provisos that when R 10 is alkyl sulphonyl, R 11 is also alkyl sulphonyl, and when R 1 is H, R 10 and R 11 are both H, and # indicates attachment of the CH 2 -V-A-COOR 1 radical to the cyclopentane ring in alpha or beta configuration, and the C(OR 10 )R 2 -C(OR 11 )R 2 R 3 radical to the cyclopropane ring in oxo or endo configuration, and their preparation. Compounds of the above formula in which R 1 is other than H and R 10 and R 11 are both H are prepared by esterifying the corresponding free acids, and those in which R 1 , R 10 and R 11 are all H by reacting compounds of the formula wherein R 12 and R 13 are C 1-4 alkyl, with acids with pK's less than 5. Compounds in which R 10 and R 11 are both C 1-5 alkylsulphonyl and R 1 is other than H are obtained by reacting the corresponding compounds of Formula I above in which either R 10 and R 11 are both H or R 10 is H and R 11 is C 1-5 allylsulphonyl with the appropriate alkylsulphonyl halides or alkanesulphonic anhydrides, and those in which R 10 is H and R is C 1-5 alkyl sulphonyl by reacting the corresponding disulphonic acid esters with water at temperatures of 0‹ to 60‹ C. or with a combination of water, bases characterized by their water solution having pH's 8 to 12 and sufficient inert water-soluble organic diluents to form basic and substantially homogeneous reaction mixtures at temperatures of 40‹ to 100‹ C. The alpha and beta isomers of those compounds in which R 10 and R 11 are both H may be converted into the corresponding beta and alpha isomers respectively by maintaining them in the presence of inert liquid diluents in the range of 0‹ to 100‹ C. and in the presence of alkali metal amides, alkali metal alkoxides, alkyl metal hydrides or triarylmethyl alkali metals.
GB5802771A 1969-03-14 1970-03-10 Bicyclo[3,1,0]hexan-3-one derivatives and the manufacture thereof Expired GB1282663A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB5802771A GB1282663A (en) 1969-03-14 1970-03-10 Bicyclo[3,1,0]hexan-3-one derivatives and the manufacture thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US80740569A 1969-03-14 1969-03-14
GB5802771A GB1282663A (en) 1969-03-14 1970-03-10 Bicyclo[3,1,0]hexan-3-one derivatives and the manufacture thereof

Publications (1)

Publication Number Publication Date
GB1282663A true GB1282663A (en) 1972-07-19

Family

ID=26267713

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5802771A Expired GB1282663A (en) 1969-03-14 1970-03-10 Bicyclo[3,1,0]hexan-3-one derivatives and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB1282663A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4056554A (en) * 1975-02-24 1977-11-01 The Upjohn Company 2,2-Difluoro-16-phenoxy-13,14-dihydro-PGF1, analogs
US4056556A (en) * 1975-02-24 1977-11-01 The Upjohn Company 2,2-Difluoro-16-phenoxy-PGE2 analogs
US4056555A (en) * 1975-02-24 1977-11-01 The Upjohn Company 2,2-Difluoro-16-phenoxy-PGA2 analogs
US4056557A (en) * 1975-02-24 1977-11-01 The Upjohn Company 2,2-Difluoro-16-phenoxy-PGF1 analogs
US4057574A (en) * 1975-02-24 1977-11-08 The Upjohn Company 2,2-Difluoro-16-phenoxy-13,14-dihydro-PGA2 analogs
US4059614A (en) * 1975-02-24 1977-11-22 The Upjohn Company 2,2-Difluoro-16-phenoxy-PGE1 analogs

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4056554A (en) * 1975-02-24 1977-11-01 The Upjohn Company 2,2-Difluoro-16-phenoxy-13,14-dihydro-PGF1, analogs
US4056556A (en) * 1975-02-24 1977-11-01 The Upjohn Company 2,2-Difluoro-16-phenoxy-PGE2 analogs
US4056555A (en) * 1975-02-24 1977-11-01 The Upjohn Company 2,2-Difluoro-16-phenoxy-PGA2 analogs
US4056557A (en) * 1975-02-24 1977-11-01 The Upjohn Company 2,2-Difluoro-16-phenoxy-PGF1 analogs
US4057574A (en) * 1975-02-24 1977-11-08 The Upjohn Company 2,2-Difluoro-16-phenoxy-13,14-dihydro-PGA2 analogs
US4059614A (en) * 1975-02-24 1977-11-22 The Upjohn Company 2,2-Difluoro-16-phenoxy-PGE1 analogs
US4064160A (en) * 1975-02-24 1977-12-20 The Upjohn Company 2,2-Difluoro-16-phenoxy-13,14 dihydro-PGE, analogs
US4097519A (en) * 1975-02-24 1978-06-27 The Upjohn Company 2,2-Difluoro-16-phenoxy-PGA1 analogs

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees