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GB1471070A - Prostenoic acid derivatives and method for preparing same - Google Patents

Prostenoic acid derivatives and method for preparing same

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Publication number
GB1471070A
GB1471070A GB1874974A GB1874974A GB1471070A GB 1471070 A GB1471070 A GB 1471070A GB 1874974 A GB1874974 A GB 1874974A GB 1874974 A GB1874974 A GB 1874974A GB 1471070 A GB1471070 A GB 1471070A
Authority
GB
United Kingdom
Prior art keywords
alkoxy
alkyl
trans
compounds
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
GB1874974A
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
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB1471070A publication Critical patent/GB1471070A/en
Expired legal-status Critical Current

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    • 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
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/13—Monohydroxylic alcohols containing saturated rings
    • C07C31/133—Monohydroxylic alcohols containing saturated rings monocyclic
    • C07C31/1333—Monohydroxylic alcohols containing saturated rings monocyclic with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/40—Halogenated unsaturated alcohols
    • C07C33/44—Halogenated unsaturated alcohols containing rings other than six-membered aromatic rings
    • 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
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/14—Preparation of ethers by exchange of organic parts on the ether-oxygen for other organic parts, e.g. by trans-etherification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/48—Preparation of compounds having groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/164—Unsaturated ethers containing six-membered aromatic rings
    • C07C43/166—Unsaturated ethers containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/17—Unsaturated ethers containing halogen
    • C07C43/174—Unsaturated ethers containing halogen containing six-membered aromatic rings
    • C07C43/176—Unsaturated ethers containing halogen containing six-membered aromatic rings having unsaturation outside the aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/30—Compounds having groups
    • C07C43/303—Compounds having groups having acetal carbon atoms bound to acyclic carbon atoms
    • 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
    • C07B2200/07—Optical isomers
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes
    • 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

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

Abstract

1471070 Prostaglandins AMERICAN CYANAMID CO 29 April 1974 [11 May 1973] 18749/74 Heading C2C [Also in Division C3] The invention comprises prostaglandins of the Formula A wherein R 1 is C 1-4 alkoxy, #-hydroxy-C 1-4 alkoxy or #-tetrahydropyran-2<SP>1</SP>-yloxy-C 1-4 alkoxy ; R 2 is H, C 1-4 alkyl or triphenylmethyl; R 3 is straight chain C 2-10 alkyl optionally substituted with 1 or 2 C 1-4 alkyl radicals, straight chain C 3-10 alkenylmethyl, optionally substituted by 1 or 2 C 1-4 alkyl radicals, C 4-9 cycloalkyl, C 5-10 alkylcycloalkyl, C 6-12 cycloalkyl-alkyl, in which the cycloalkyl is optionally substituted by a C 1-4 alkyl radical, C 5-9 cycloalkenyl, C 6-10 alkyl-cycloalkenyl, C 6-12 cycloalkenyl-alkyl in which the cycloalkenyl is optionally substituted by a C 1-4 alkyl radical, adamantyl or adamantyl-C 1-4 alkyl; R 4 is OH, C 1-12 alkoxy, C 1-12 alkoxy or 2-tetrahydropyranyloxy; R 3 is H or C 1-3 alkyl; V is >C=O, and Z is -(CH 2 ) n -, -(CH 2 ) n -C(R 5 ) 2 .CH 2 -, -(CH 2 ) n .CH(R 6 )-, -(CH 2 ) n -O-CH 2 or cis- CH 2 -CH=CH-(CH 2 ) p , wherein n is 3 to 8, p is 2 to 6, R 5 is C 1-3 alkyl and R 6 is C 1-3 alkyl, F or phenyl; and the radical -C 13 -C 14 is ethylene or trans-vinylene, and non-toxic salts thereof when R 4 is OH; subject to the following provisos: (i) when R 1 is #-hydroxy-C 1-4 alkoxy, then R 4 is not 2-tetrahydropyranyloxy; (ii) when R 1 is #-tetrahydropyran-2<SP>1</SP>-yloxy-C 1-4 alkoxy, then R 4 is not OH or R 2 is not alkyl; (iii) when R 2 is H, then R 1 is not #-tetrahydropyran-2<SP>1</SP>- yloxy-C 1-4 alkoxy or R 4 is not 2-tetrahydropyranyloxy; (iv) when R 2 is triphenylmethyl, then R 4 is not OH or R 1 is not #-hydroxy-C 1-4 alkoxy; (v) when R 7 is C 1-3 alkyl, then R 2 must be hydrogen; and (vi) when C 13 -C 14 is ethylene, then Z is not cis-CH 2 CH = CH(CH 2 ) p . The compounds are prepared by reacting cyclopentenones of the Formula B wherein R<SP>1</SP> 1 is C 1-4 alkoxy or #-tetrahydropyran- 2<SP>1</SP>-yloxy-C 1-4 alkoxy; and R<SP>1</SP> 4 is 2-tetrahydrohydropyranyloxy or C 1-12 alkoxy with compounds of the formula wherein R is C 1-7 alkyl and R<SP>1</SP> 2 is C 1-4 alkyl or triphenylmethyl to give cyclopentanones of the formula followed by hydrolysis with weak acids to give compounds of the formula A above in which Y is >C=O, R 1 is C 1-4 alkoxy or #-hydroxy- C 1-4 alkoxy; R 4 is OH or C 1-12 alkoxy, R<SP>9</SP> is H or C 1-4 alkyl and -C 13 -C 14 - is trams-vinylene ; and if desired, reducing said compounds to give corresponding compounds in which Y is >CH(OH), and, when desired oxidizing alkyl or 2-tetrahydropyranyl 9,15-dihydroxy-13-transprostenoates with magnese dioxide or 2,3-dichloro-5,6-dioyano-1,4-benzoquinone to the corresponding alkyl or 2-tetrahydropyranyl 9-hydroxy- 15 - oxo - 13 - trans - prostenoates, protecting all free hydroxy groups and treating the resulting protected compounds with C 1-3 alkylmagnesium halides, and removing the protecting groups; if desired, oxidizing 9-hydroxy groups to 9-oxo groups, and if desired hydrogenating C 12 -C 16 trans-vinylene to ethylene, and if desired hydrolysing any resulting ester, and converting the resulting acids to salts. The following intermediates and starting materials are also prepared: cyclopentenones of Formula B above in which R<SP>1</SP> 1 is R<SP>1</SP> is C 1-4 alkoxy, #-tetrahydropyran-2<SP>1</SP>-yloxy-C 1-4 alkoxy or #-hydroxy-C 1-4 alkoxy, Br and H, and R<SP>1</SP> 4 is H, 2-tetrahydropyronyloxy or C 1-12 alkoxy; cis - 1 - ethyl - 2 - (2,2 - dimethoxyethyl)- cyclopropane, cis-1-ethyl-2-(2-hydroxyethyl)- cyclopropane, cyclopentylacetyl chloride, compounds of the formula HC#C-CH(OR<SP>10</SP>)R 3 and IHC = CHCH(OR<SP>10</SP>)R 3 , wherein R<SP>10</SP> is H, triphenylmethyl, methyl or 2-tetrahydpyronyl; 1 - chloro - 4 - cyclopentyl - 1 - trans - buten -3 - one; 4 - cyclopentyl - 1 - iodo - 1 - trans - buten- 3 - one; 4 - cyclopentyl - triodo - 3 - (p - methoxy phenyl diphenyl-methoxy)-1-traps-butene; 1- chloro - trans - 1 - octen - 3 - one, 1 - iodo - trans- 1 - octen - 3 - one; and 1 - iodo - 3-(p - -methoxy phenyldiphenylmethoxy) - trans-1-octene. Pharmaceutical compositions, suitable for oral or parenteral administration, contain the above prostaglandins or salts thereof, together with pharmaceutically acceptable carriers or diluents. The compounds possess prostaglandin-like pharmacological properties.
GB1874974A 1973-05-11 1974-04-29 Prostenoic acid derivatives and method for preparing same Expired GB1471070A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US359391A US3876690A (en) 1973-05-11 1973-05-11 1-alkoxy-9-keto-prostenoic acid derivatives

Publications (1)

Publication Number Publication Date
GB1471070A true GB1471070A (en) 1977-04-21

Family

ID=23413612

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1874974A Expired GB1471070A (en) 1973-05-11 1974-04-29 Prostenoic acid derivatives and method for preparing same

Country Status (8)

Country Link
US (1) US3876690A (en)
JP (1) JPS5030850A (en)
BE (1) BE814869A (en)
CA (1) CA1027560A (en)
DE (1) DE2422512A1 (en)
FR (1) FR2228498B1 (en)
GB (1) GB1471070A (en)
NL (1) NL7405901A (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1053781B (en) * 1974-09-25 1981-10-10 Erba C S P A Ora Farmitalia OMEGA NOR CICLOALCIL 13.14 DEIDRO PROSTAGLANDINE
US4169145A (en) * 1974-09-25 1979-09-25 Carlo Erba S.P.A. ω-Nor-cycloalkyl-13,14-dehydro-prostaglandins
US3985798A (en) * 1975-01-27 1976-10-12 American Cyanamid Company 11α-HOMO-PROSTANOIC ACIDS AND ESTERS
JPS5361706U (en) * 1976-10-27 1978-05-25
US4189597A (en) * 1977-03-30 1980-02-19 American Cyanamid Company 11-(2-Hydroxyethylthio)prostenoic acid E series derivatives
US4085272A (en) * 1977-03-30 1978-04-18 American Cyanamid Company 11-(2-Hydroxyethylthio)prostenoic acid E2 series derivatives
US4218566A (en) * 1977-03-30 1980-08-19 American Cyanamid Company 11-(2-Hydroxyethylthio) prostenoic acid E and F series derivatives
DK1008588T3 (en) * 1997-02-10 2003-07-28 Ono Pharmaceutical Co 11,15-O-dialkylprostaglandin E derivatives, processes for their preparation and pharmaceutical compositions comprising them as active ingredient

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1330003A (en) * 1970-05-27 1973-09-12 May & Baker Ltd Cyclopentane derivatives
US3735005A (en) * 1970-08-19 1973-05-22 Alza Corp Method for preparing a viable platelet concentrate
US3781325A (en) * 1971-05-04 1973-12-25 Upjohn Co 15-methoxy-pgf2a

Also Published As

Publication number Publication date
DE2422512A1 (en) 1974-11-21
US3876690A (en) 1975-04-08
JPS5030850A (en) 1975-03-27
FR2228498B1 (en) 1977-03-11
CA1027560A (en) 1978-03-07
NL7405901A (en) 1974-11-13
BE814869A (en) 1974-11-12
FR2228498A1 (en) 1974-12-06
AU6803374A (en) 1975-10-23

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee