GB1501864A - Prostaglandin derivatives and their preparation - Google Patents

Prostaglandin derivatives and their preparation

Info

Publication number
GB1501864A
GB1501864A GB13399/74A GB1339974A GB1501864A GB 1501864 A GB1501864 A GB 1501864A GB 13399/74 A GB13399/74 A GB 13399/74A GB 1339974 A GB1339974 A GB 1339974A GB 1501864 A GB1501864 A GB 1501864A
Authority
GB
United Kingdom
Prior art keywords
methyl
trans
methylethoxy
oxo
methoxy
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
GB13399/74A
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.)
Gist Brocades NV
Original Assignee
Gist Brocades NV
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 Gist Brocades NV filed Critical Gist Brocades NV
Priority to GB13399/74A priority Critical patent/GB1501864A/en
Priority to CH382475A priority patent/CH615159A5/de
Priority to AU79498/75A priority patent/AU497219B2/en
Priority to FR7509309A priority patent/FR2265361B1/fr
Priority to BE154743A priority patent/BE827156A/en
Priority to LU72128A priority patent/LU72128A1/xx
Priority to DE19752513222 priority patent/DE2513222A1/en
Priority to JP50036511A priority patent/JPS50135283A/ja
Priority to SE7503438A priority patent/SE7503438L/xx
Priority to DK125975A priority patent/DK125975A/da
Priority to US05/561,895 priority patent/US4054595A/en
Priority to ZA00751882A priority patent/ZA751882B/en
Priority to HU75GI217A priority patent/HU173457B/en
Priority to IE665/75A priority patent/IE42704B1/en
Priority to IT67770/75A priority patent/IT1046092B/en
Priority to NL7503654A priority patent/NL7503654A/en
Priority to US05/831,949 priority patent/US4190670A/en
Priority to US05/831,950 priority patent/US4164446A/en
Publication of GB1501864A publication Critical patent/GB1501864A/en
Priority to US05/955,005 priority patent/USRE30287E/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/08—Copper compounds
    • 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
    • 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
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen 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
    • C07B2200/09—Geometrical isomers

Landscapes

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

Abstract

1501864 Prostaglandins; organometallic compounds GIST-BROCADES NV 25 March 1975 [26 March 1974 (2)] 13399/74 Headings C2C and C2J [Also in Division C3] The invention comprises a process for the preparation of prostaglandins of the Formula I wherein the dotted line in the position 8-12 indicates the optional presence of a double bond; Z is CH 2 CH or cis-CH=CH; R is (a) -CH(OH)CH 2 CH 2 R 1 , (b) CH 2 CH(OH)CH 2 R 1 or (c) CH 2 CH 2 CH(OH)R 1 , wherein R 1 is H, methyl or ethyl; R 2 is oxygen or a #- or α-hydrogen and an α- or #-hydroxyl; R 3 is H or OH; and R 4 is H or methyl, with the provisos (1) when there is a double bond in the 8-12 position, R<SP>3</SP> is not OH and (2) when there is a double bond in the 8-12 position, R 2 is not a #- or α-hydrogen and an α- or #-hydroxyl; and the compounds of the above formula wherein Z, R, R 2 , R 3 and R 4 are as defined above with the further provisos that (3) when R 1 , R 3 and R 4 are H, R 2 is oxygen, a double bond is in the 8-12 position, R is not the group (b) above, and (4) when R 1 , R 3 and R 4 are H, R 2 is oxygen; the 15-hydroxyl group is in the α-configuration, Z is cis CH = CH and the 8-12 position is saturated, R is not the group (a) above, and pharmaceutically acceptable salts and alkyl esters thereof. The process comprises subjecting compounds of Formula II wherein the dotted line in the 10-11 indicates the optional presence of a double bond in which case the 8-12 position is saturated and R 3 is H, to the hydroxylating activity of (i) microorganisms (or enzymes thereof) of the Division of Eumycota or (ii) when it is desired to prepare an 18- or 19-hydroxy-prostaglandin derivative, microorganisms (or enzymes thereof) of the Family of Streptomycetaceae, and, if desired, converting the resulting products into salts or esters, with the proviso that when the microorganism is Cunninghamella blakesleena (ATCC 9245) the compound of Formula II is not PGA 2 . The following intermediates are also prepared: 1 - chloro - trans - 1 - decen - 3 - one, 1 - iodotrans - 1 - decen - 3 - one; 1 - iodo - 3 - hydroxytrans - 1 - decene, 1 - iodo - 3 - (1 - methoxy - 1- methylethoxy) - trans - 1 - decene; methyl dl - 9 - oxo - 15 - (1 - methoxy - 1 - methylethoxy) - 20 - ethyl - trans - 13 - prostenoate; methyl dl - 9 - oxo - 15 - (1 - methoxy - 1- methylethoxy) - trans - 13 - prostenoate; methyl dl - 9 - oxo - 15 - (1 - methoxy - 1- methylethoxy) - 20 - methyl - trans - 13- prostenoate; methyl dl - 9 - oxo - 15 - (1- methoxy - 1 - methylethoxy) - 20 - ethyl (and 20 - methyl) - cis - 5, trans - 13 - prostadienoate; methyl dl - 9 - oxo - 15 - (1 - methoxy- 1 - methylethoxy) - cis, 5, trans - 13 - prostadienoate; compounds of the Formula II above and the methyl esters thereof; methyl dl - 9 - hydroxy - 15 - oxo - 20 - ethyl (and methyl) - trans - 13 - prostenoate, methyl dl - 9 - hydroxy - 15 - oxo - trans - 13 - prostenoate, methyl dl - 9 - hydroxy - 15 - oxo - 20- ethyl (and methyl) - cis - 5, trans - 13 - prostadienoate; and methyl dl - 9 - hydroxy - 15- oxo - cis - 5, trans - 13 - prostadienoate. dl - 1 - Pentynyl - 1 - [3 - (1 - methoxy - 1- methylethoxy)trans - 1 - octenyl (and nonenyl and decenyl)]cuprate is prepared by reacting copper pentyne with dl-1-lithio-3-(1-methoxy-1- methylethoxy)-trans-1-octene (or nonene or decene), obtained by reacting t-butyllithium with dl-1- iodo - 3 - (1 - methoxy - 1 - methylethoxy)- trans-1-octene (or nonene or decene). Pharmaceutical compositions, suitable for oral or parenteral administration, contain the above novel prostaglandins and pharmaceutically acceptable carriers or diluents. The compounds possess similar pharmacological properties to those of the naturally occurring prostaglandins. Reference has been directed by the Comptroller to Specifications 1,040,544; 1,097,533; 1,097,157; 1,120,243; 1,163,762; 1,314,291 and 1,314,292.
GB13399/74A 1974-03-26 1974-03-26 Prostaglandin derivatives and their preparation Expired GB1501864A (en)

Priority Applications (19)

Application Number Priority Date Filing Date Title
GB13399/74A GB1501864A (en) 1974-03-26 1974-03-26 Prostaglandin derivatives and their preparation
DK125975A DK125975A (en) 1974-03-26 1975-03-25
US05/561,895 US4054595A (en) 1974-03-26 1975-03-25 18 OR 19 Hydroxy prostaglandins
FR7509309A FR2265361B1 (en) 1974-03-26 1975-03-25
BE154743A BE827156A (en) 1974-03-26 1975-03-25 PROSTAGLANDINS
LU72128A LU72128A1 (en) 1974-03-26 1975-03-25
DE19752513222 DE2513222A1 (en) 1974-03-26 1975-03-25 18 XI, 19 XI AND 20 XI HYDROXY PROSTAGLANDIN COMPOUNDS
JP50036511A JPS50135283A (en) 1974-03-26 1975-03-25
SE7503438A SE7503438L (en) 1974-03-26 1975-03-25
CH382475A CH615159A5 (en) 1974-03-26 1975-03-25
AU79498/75A AU497219B2 (en) 1974-03-26 1975-03-25 18-19 and 20-HYDROXY PROSTAGLANDIN DERIVATIVES
ZA00751882A ZA751882B (en) 1974-03-26 1975-03-25 Novel prostaglandin derivatives
HU75GI217A HU173457B (en) 1974-03-26 1975-03-25 Process for the microbiological preparation of 18-, 19- and 20-hydroxy-prostaglandin derivatives
IE665/75A IE42704B1 (en) 1974-03-26 1975-03-25 Prostaglandin derivatives and their preparation
IT67770/75A IT1046092B (en) 1974-03-26 1975-03-26 PROSTAGLANDINIC DERIVATIVES AND PROCEDURE FOR THEIR PREPARATION
NL7503654A NL7503654A (en) 1974-03-26 1975-03-26 PROSTAGLANDIN DERIVATIVES.
US05/831,949 US4190670A (en) 1974-03-26 1977-09-09 Prostaglandin derivatives
US05/831,950 US4164446A (en) 1974-03-26 1977-09-09 Prostaglandin derivatives
US05/955,005 USRE30287E (en) 1974-03-26 1978-10-26 19 Hydroxy prostaglandins

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB13399/74A GB1501864A (en) 1974-03-26 1974-03-26 Prostaglandin derivatives and their preparation

Publications (1)

Publication Number Publication Date
GB1501864A true GB1501864A (en) 1978-02-22

Family

ID=10022263

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13399/74A Expired GB1501864A (en) 1974-03-26 1974-03-26 Prostaglandin derivatives and their preparation

Country Status (3)

Country Link
BE (1) BE827156A (en)
GB (1) GB1501864A (en)
ZA (1) ZA751882B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7109371B2 (en) 2004-01-05 2006-09-19 Johnson Matthey Public Limited Company Prostaglandin synthesis

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7109371B2 (en) 2004-01-05 2006-09-19 Johnson Matthey Public Limited Company Prostaglandin synthesis
US7141706B2 (en) 2004-01-05 2006-11-28 Johnson Matthey Public Limited Company Protected and unprotected triols for prostaglandin synthesis
US7161042B2 (en) 2004-01-05 2007-01-09 Johnson Matthey Public Limited Company Protected diols for prostaglandin synthesis

Also Published As

Publication number Publication date
ZA751882B (en) 1976-03-31
BE827156A (en) 1975-09-25

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Legal Events

Date Code Title Description
PS Patent sealed
49R Reference inserted (sect. 9/1949)
429A Application made for amendment of specification (sect. 29/1949)
429H Application (made) for amendment of specification now open to opposition (sect. 29/1949)
429D Case decided by the comptroller ** specification amended (sect. 29/1949)
SPA Amended specification published
PCNP Patent ceased through non-payment of renewal fee