IL36682A - 15-alkyl prostaglandins - Google Patents

15-alkyl prostaglandins

Info

Publication number
IL36682A
IL36682A IL36682A IL3668271A IL36682A IL 36682 A IL36682 A IL 36682A IL 36682 A IL36682 A IL 36682A IL 3668271 A IL3668271 A IL 3668271A IL 36682 A IL36682 A IL 36682A
Authority
IL
Israel
Prior art keywords
methyl
inclusive
racemic
compound according
formula
Prior art date
Application number
IL36682A
Other versions
IL36682A0 (en
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
Publication of IL36682A0 publication Critical patent/IL36682A0/en
Publication of IL36682A publication Critical patent/IL36682A/en

Links

Classifications

    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Claims (28)

I f t ( 2711-F WHAT WE CLAIM ISt
1. A process for producing an optically active compound of the f o rmu 1 a : or a racemic compound of that formula and the mirror image thereof, or the 15-epimer of either of those, wherein X is trans-CH=CH- or -CH2CH2-, and Y and Z are both -CH2CH2- , or wherein X is trans-CH=CH- and Y is cis-CHsCH-, and Z is -CH2CH2' in iii I ΓΙΙ111ΓΤΤ wherein R2 is methyl or ethyl, wherein R4 is hydrogen or alkyl of ope to 8 carbon atoms, inclusive, and wherein indicates attachment of hydroxy %o the ring in alpha or beta configuration, which comprises the steps, ( ) reacting an optically active compound of the formula: 0 (A)3-Si- Y- (CH2)3-C-0-R3 (A)3-Si- CH2-Z-CH2CH3 or a racemic compound of that formula and the mirror image thereof, wherein A is alkyl of one to 4 carbon atoms, inclusive,^ phenyl, phenyl substituted with one or 2 fluoro, chloro, or alkyl of one to carbon atoms, inclusive, or alkyl of to 12 carbon atoms, inclusive, wherein R3 is alkyl of one to 8 carbon atoms, inclusive, or -Si (A )3 wherein A i§ as defined above, and wherein X, Y, Z, and ^-τ^ are as defined above, with a compound of the formula R2MgX wherein X is chloro, bromo, or iodOj and R2 is as defined above, and (2) hydrolyzing the reaction product of step (l).
2. A process according to claim 1 wherein the product is optically active, with the formula shown*
3. A process according to claim 1 wherein the product is racemic, with the formula shown and the mdaror image thereof.
4. . A process according to claim 1 wherein the product is optically active, with the formula shown but epimeric at C-15»
5. A purocess according to claim 1 wherein the product is racemic, with the formula shown and the mirror image thereof but both epimeric at C-15.
6. An optically active compound of the formula t or a racemic compound of that formula and the mirror image thereof, wherein is hydrogen, alkyl of one to 8 carbon atoms, inclusive, or a pharmacologically acceptable cation, wherein R9 is methyl or ethyl, wherein A is - erein X is trans -CH=CH- or -CHgCHg- and Y and Z are both -CH2CH2-, or wherein X is trans-CH=CH- , Y is cis-CH=CH- , and Z proviso that R9 is ethyl when A is =0 or , and Y and Z are both -CH2CH2-.
7. * A compound according to claim 6 wherein A is =0.
8. A compound according to claim 6 wherein A is
9. A compound according to claim 6 wherein A is ^OH.
10. A compound according to any one of claims 6 to 9i inclusive, wherein X, Y, and Z are all -CHgCHg-.
11. A compound according to any one of claims 6 to 9» inclusive, wherein X is trans-CH=CH- , and Y and Z are both -CHgCHg-.
12. A compound according to any one of claims 6 to 9, inclusive, wherein X is trans-CH==CH, Y is cis-CH=CH-, and Z is -CH2CH2-.
13. A compound according to any one <£ claims to 12, inclusive wherein R^ is hydrogen.
14. A compound according to any one of claims 6 to 12, inclusive wherein R^ is methyl.
15. An optically active compound according to any one of claims 6 to 14, inclusive.
16. A racemic compound according to any one of claims 6 to 14, Inclusive.
17. Dihydro-15-methyl-K^ methyl ester.
18. Dihydro-15-methyl-PGF methyl ester. la
19. Dihydro-15-methyl-PGF^.
20. 15-Eth l-PGF2a- -methyl ester.
21. 15- ethyl-PGF .
22. 15-Methyl-PGE2its methyl ester and isopropyl ester.
23. 15-Methyl-PGF2a, its methyl ester and THAM salt.
24. 15-Methyl-PGF2£ and its methyl ester.
25. Racemic 15-methyl-PGFnQ. Ip
26. Racemlc 15-methyl-PGE2.
27. Racemic 15-methyl-PGF^ .
28. Racemic 15-methyl-PGF
IL36682A 1970-05-04 1971-04-21 15-alkyl prostaglandins IL36682A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US3454970A 1970-05-04 1970-05-04
US3451870A 1970-05-04 1970-05-04
US3730870A 1970-05-14 1970-05-14
US3730770A 1970-05-14 1970-05-14

Publications (2)

Publication Number Publication Date
IL36682A0 IL36682A0 (en) 1971-06-23
IL36682A true IL36682A (en) 1976-04-30

Family

ID=27488226

Family Applications (1)

Application Number Title Priority Date Filing Date
IL36682A IL36682A (en) 1970-05-04 1971-04-21 15-alkyl prostaglandins

Country Status (9)

Country Link
CA (1) CA959485A (en)
DE (2) DE2166630C3 (en)
FR (1) FR2100627B1 (en)
GB (2) GB1314293A (en)
IL (1) IL36682A (en)
MY (1) MY7400305A (en)
NL (1) NL154729B (en)
NO (2) NO135935C (en)
SE (1) SE388852B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2258668C3 (en) * 1971-12-03 1981-08-06 Syntex Corp., Panama-City New prostaglandins, processes for their production and pharmaceuticals containing them
US3887587A (en) * 1972-04-17 1975-06-03 Pfizer Synthesis of prostaglandins of the one-series

Also Published As

Publication number Publication date
DE2166630B2 (en) 1979-02-22
NL154729B (en) 1977-10-17
FR2100627B1 (en) 1981-12-18
NO135935B (en) 1977-03-21
NO140422C (en) 1979-08-29
DE2121980C3 (en) 1980-02-14
FR2100627A1 (en) 1972-03-24
NO135935C (en) 1977-06-29
SE388852B (en) 1976-10-18
DE2166630A1 (en) 1974-12-12
GB1314291A (en) 1973-04-18
DE2121980A1 (en) 1971-11-25
NO140422B (en) 1979-05-21
CA959485A (en) 1974-12-17
DE2121980B2 (en) 1979-06-07
MY7400305A (en) 1974-12-31
NL7105999A (en) 1971-11-08
DE2166630C3 (en) 1979-10-11
IL36682A0 (en) 1971-06-23
GB1314293A (en) 1973-04-18

Similar Documents

Publication Publication Date Title
US4107213A (en) 2-Decarboxy-2-hydroxy-methyl-5-oxa-ω-phenoxy-PGD1 compounds
ES8107148A1 (en) Fluoroalkenyl-substituted cyclopropanecarboxylic acid esters, intermediate products therefor, preparation of the compounds and their utilization as insecticides and/or acaricides.
US4122100A (en) Cis-4,5-didehydro-11-deoxy-PGF1 analogs
ES8505650A1 (en) Fat emulsion containing prostaglandin.
AR241593A1 (en) PROCEDURE FOR PREPARING DERIVATIVES OF QUINOLIN-3-CARBOXYLIC ACID.
IL33949A (en) 5,6-dehydro pge2,pgf2alpha and pgf2beta derivatives
IE46036L (en) Prostacyclin and derivatives thereof
IL36682A (en) 15-alkyl prostaglandins
GB1471070A (en) Prostenoic acid derivatives and method for preparing same
HUT41015A (en) Process for preparing amino-thiazole-acetic acid derivatives
KR850000026A (en) Method and composition for preparing bicyclo (3.2.1) -octane carboxylic acid
ES390720A1 (en) Cyclopentanone derivatives
US3974192A (en) 16-Fluoro prostaglandin B1 analogs
US4209615A (en) Phenyl-substituted 9-deoxy-6,9α-epoxymethano-PG analogs
US4208538A (en) 2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-ω-phenyl-PGF2 compounds
US4041066A (en) 4,5-Cis-didehydro-PGE1 compounds
GB1338749A (en) Process for the preparation of phenothiazine derivatives
ES8103742A2 (en) 1,3-Benzodioxin derivatives
ES395036A2 (en) Prostaglandins and the preparation thereof
US3983163A (en) 5-Oxa phenyl- and phenoxy-substituted prostaglandin β, analogs
US4337337A (en) 2,5-Inter-o-phenylene-3,4-dinor-5,9α-epoxy-6-iodo-PGF1 compounds
GB1269658A (en) Improvements in or relating to prostaglandins and the manufacture thereof
GB1414383A (en) Prostatrienoic acid derivatives and process
GB1211761A (en) Improvements in or relating to cyclohexene - and cyclohexane - carboxylic acid derivatives
GB1455665A (en) Mono- and dialkylated prostynoic acid derivatives