GB1277264A - 07-acetylgonanes and derivatives therefor - Google Patents

07-acetylgonanes and derivatives therefor

Info

Publication number
GB1277264A
GB1277264A GB3816769A GB3816769A GB1277264A GB 1277264 A GB1277264 A GB 1277264A GB 3816769 A GB3816769 A GB 3816769A GB 3816769 A GB3816769 A GB 3816769A GB 1277264 A GB1277264 A GB 1277264A
Authority
GB
United Kingdom
Prior art keywords
prepared
ethynyl
ethyl
compounds
acetate
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
GB3816769A
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 LLC
Original Assignee
American Home Products Corp
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 Home Products Corp filed Critical American Home Products Corp
Publication of GB1277264A publication Critical patent/GB1277264A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
    • C07J7/004—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa
    • C07J7/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa substituted in position 16
    • C07J7/0055—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0051—Estrane derivatives
    • C07J1/0081—Substituted in position 17 alfa and 17 beta
    • C07J1/0088—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
    • C07J1/0096—Alkynyl derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C07J13/005—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 16 (17)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C07J13/007—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 17 (20)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
    • C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
    • C07J7/0025—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa substituted in position 16
    • C07J7/003—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group

Abstract

1277264 17-Acetylgonanes AMERICAN HOME PRODUCTS CORP 30 July 1969 [30 July 1968] 38167/69 Headings C2C and C2U 17 - Acetyl - gon - 16 - enes and formates and alkanoates of 17α-acetylgonan-17#-ols, and D- homo analogues of these compounds, are prepared by hydrating the corresponding compounds containing an ethynyl group in place of the acetyl group. Hydration may be effected by heating in water in the presence of a catalyst, such as a mercurated cation exchange resin or silver nitrate. The 17-ethynyl-gon-16-enes and their D-homo analogues may in turn be prepared by dehydration of the corresponding 17α-ethynylgonan - 17# - ols and their D - homo analogues, for example using phosphorus oxychloride and pyridine; and the 17α-ethynylgonan-17#- ol formates and their D-homo analogues may in turn be prepared by formylation of the free 17B-ols, for example using DMF in the presence of phosphorus oxychloride. Novel products have the formula wherein R is C 2-6 alkyl; n is 1 or 2; X is a radical containing at least 11 carbon atoms so arranged as to complete a steroid of the cyclopentanoperhydrophenanthrene series or a D- homo analogue thereof; -C 16 -C 17 - is a divalent radical of one of the formulµ (wherein Y is H or CH 2 R<SP>4</SP> in which R<SP>4</SP> is H or C 1-6 alkyl; and R<SP>3</SP> is H or C 1-6 alkyl) provided that when the compounds are 17#-acetoxy-17α- acetyl compounds X is other than The 17 - acetyl - 16 - alkylgon - 16 - enes are prepared from the corresponding 16-unsubstituted compounds by reacting with a diazoalkane and then heating the thus-formed 16α,- 17α-alkyleneazogonane or D-homo analogue thereof. All the above compounds may be racemates or d-enantiomers. d - 17α - Ethynyl - 3 - methoxyestra - 1,3,5(10)- trien - 17# - ol acetate is prepared from the free 17#-ol and acetic anhydride in ethyl acetate containing perchloric acid. dl- 13#-ethyl-17α- ethynyl - 3 - methoxygona - 1,3,5(10) - trien- 17#-ol acetate is prepared similarly. dl-13#- Ethyl - 17α - ethynylgon - 5 - ene - 3#,17# - diol- 3-acetate is prepared by acetylating dl- 13#- ethyl - 17α - ethynyl - 17# - hydroxy - gon - 4- en - 3 - one to give dl - 13# - ethyl - 17α- ethynyl - gona - 3,5 - diene - 3,17# - diol diacetate, reducing this to dl - 13# - ethyl - 17α - ethynylgon - 5 - en - 3#,17# - diol 17 - acetate, hydrolysing this to the free diol and acetylating this. The novel 13-polycarbon alkyl steroids variously have estrogenic and anti-lipemic activity, and they may be made up into pharmaceutical compositions with suitable carriers.
GB3816769A 1968-07-30 1969-07-30 07-acetylgonanes and derivatives therefor Expired GB1277264A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US74859468A 1968-07-30 1968-07-30

Publications (1)

Publication Number Publication Date
GB1277264A true GB1277264A (en) 1972-06-07

Family

ID=25010111

Family Applications (3)

Application Number Title Priority Date Filing Date
GB326671A Expired GB1277267A (en) 1968-07-30 1969-07-30 07-acetylgonanes and derivatives therefor
GB326571A Expired GB1277266A (en) 1968-07-30 1969-07-30 07-acetylgonanes and derivatives therefor
GB3816769A Expired GB1277264A (en) 1968-07-30 1969-07-30 07-acetylgonanes and derivatives therefor

Family Applications Before (2)

Application Number Title Priority Date Filing Date
GB326671A Expired GB1277267A (en) 1968-07-30 1969-07-30 07-acetylgonanes and derivatives therefor
GB326571A Expired GB1277266A (en) 1968-07-30 1969-07-30 07-acetylgonanes and derivatives therefor

Country Status (7)

Country Link
JP (3) JPS504657B1 (en)
BE (1) BE736832A (en)
CH (3) CH594699A5 (en)
DE (1) DE1938788A1 (en)
FR (1) FR2014015B1 (en)
GB (3) GB1277267A (en)
NL (1) NL6911623A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7655746B2 (en) 2005-09-16 2010-02-02 Eastman Chemical Company Phosphorus containing compounds for reducing acetaldehyde in polyesters polymers
US7838596B2 (en) 2005-09-16 2010-11-23 Eastman Chemical Company Late addition to effect compositional modifications in condensation polymers
US8557950B2 (en) 2005-06-16 2013-10-15 Grupo Petrotemex, S.A. De C.V. High intrinsic viscosity melt phase polyester polymers with acceptable acetaldehyde generation rates
US9267007B2 (en) 2005-09-16 2016-02-23 Grupo Petrotemex, S.A. De C.V. Method for addition of additives into a polymer melt

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2647452A1 (en) * 1989-05-24 1990-11-30 Theramex NEW 19-NOR 6-METHYL STEROIDS PROCESSES FOR OBTAINING THEM, THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND THEIR CONVERSION IN 19-NOR PREGNADIAN 17-SUBSTITUTED
FR2700548B1 (en) * 1993-01-20 1995-03-03 Roussel Uclaf New process for the preparation of 16 alpha-methylated steroids.

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8557950B2 (en) 2005-06-16 2013-10-15 Grupo Petrotemex, S.A. De C.V. High intrinsic viscosity melt phase polyester polymers with acceptable acetaldehyde generation rates
US8987408B2 (en) 2005-06-16 2015-03-24 Grupo Petrotemex, S.A. De C.V. High intrinsic viscosity melt phase polyester polymers with acceptable acetaldehyde generation rates
US7655746B2 (en) 2005-09-16 2010-02-02 Eastman Chemical Company Phosphorus containing compounds for reducing acetaldehyde in polyesters polymers
US7799891B2 (en) 2005-09-16 2010-09-21 Eastman Chemical Company Phosphorus containing compounds for reducing acetaldehyde in polyesters polymers
US7838596B2 (en) 2005-09-16 2010-11-23 Eastman Chemical Company Late addition to effect compositional modifications in condensation polymers
US9267007B2 (en) 2005-09-16 2016-02-23 Grupo Petrotemex, S.A. De C.V. Method for addition of additives into a polymer melt

Also Published As

Publication number Publication date
GB1277266A (en) 1972-06-07
CH585767A5 (en) 1977-03-15
JPS504659B1 (en) 1975-02-22
GB1277267A (en) 1972-06-07
FR2014015B1 (en) 1976-09-17
NL6911623A (en) 1970-02-03
JPS504657B1 (en) 1975-02-22
BE736832A (en) 1970-01-30
CH594699A5 (en) 1978-01-31
DE1938788A1 (en) 1970-02-12
JPS505711B1 (en) 1975-03-06
FR2014015A1 (en) 1970-04-10
CH564564A5 (en) 1975-07-31

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee