GB1277266A - 07-acetylgonanes and derivatives therefor - Google Patents

07-acetylgonanes and derivatives therefor

Info

Publication number
GB1277266A
GB1277266A GB326571A GB326571A GB1277266A GB 1277266 A GB1277266 A GB 1277266A GB 326571 A GB326571 A GB 326571A GB 326571 A GB326571 A GB 326571A GB 1277266 A GB1277266 A GB 1277266A
Authority
GB
United Kingdom
Prior art keywords
alkyl
compounds
group
polycarbonalkyl
ols
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
GB326571A
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 GB1277266A publication Critical patent/GB1277266A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1277266 16α - Alkyl - 13 - polycarbonalkylgonane compounds AMERICAN HOME PRODUCTS CORP 30 July 1969 [30 July 1968] 3265/71 Divided out of 1277264 Headings C2C and C2U 13 - Polycarbonalkyl - 17# - acetyl - 16α- alkyl - gonane compounds and the corresponding 17α-ols and the D-homo-analogues of these compounds, are prepared by alkylating or alkylating and oxidizing the corresponding 13- polycarbonalkyl - 17 - acetyl - gon - 16 - ene compounds and their D-homo analogues. The alkylation may be effected with an alkyl magnesium halide with subsequent acid treatment of the enolate first-formed and the oxidation directly with molecular oxygen or by using the Grignard reagent in the presence of an acyl halide, reacting the resulting enol-acylate with a peracid and hydrolysing the product. In the products, a 17α-OH group may be acylated, a 3-alkoxy-gona-1,3,5(10)-triene may be Birch reduced to a corresponding 2,5(10)-diene and this may be hydrolysed to a gon-4-en-3-one, a 17# - (α - hydroxyethyl) group formed in the Birch reduction may be oxidized to a 17#- acetyl group, and a 20-keto group may be protected as an ethylene-ketal and released again after the Birch reduction. Also described are 3-enol-acylation of #<SP>4</SP> - 3 - ones and hydrolysis of the enol acylates, hydrolysis of #<SP>5</SP>-3- acyloxy compounds to #<SP>5</SP>-3-ols and oxidation of these to #<SP>4</SP>-3-ones, and standard introductions of 6-halo, 6-methyl and 10-methyl substituents and #<SP>1</SP>, #<SP>6</SP> and #<SP>9(10)</SP> double bonds, via intermediates including 5α,6α-epoxides, 6α,7α-epoxides, 6# - methyl - 5α - ols and #<SP>3,5</SP> - 3- acyloxy - 6 - hydroxymethyl and #<SP>4</SP> - 3 - keto- 6-methylene compounds. Novel products have the formulµ 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 or D-homosteroid nucleus; G is CO or CH(OR<SP>1</SP>) where R<SP>1</SP> is H or C 1-6 alkanoyl; Q is H, OH or OCOR<SP>2</SP> where R<SP>2</SP> is C 1-6 alkyl; and Z is C 1-6 alkyl, provided that when G is CO and Q is H, X is other than where R<SP>7</SP> is H or CH 3 ; and R<SP>5</SP> is C 1-6 alkyl. All the above compounds may be racemates or d-enantiomers. The novel 13-polycarbonalkyl-16α-alkyl steroids have variously estrogenic, anti-estrogenic, anti-lipemic and progestational properties, and they may be made up into pharmaceutical compositions with suitable carriers.
GB326571A 1968-07-30 1969-07-30 07-acetylgonanes and derivatives therefor Expired GB1277266A (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
GB1277266A true GB1277266A (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
GB3816769A Expired GB1277264A (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

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
GB3816769A Expired GB1277264A (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 (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990015067A2 (en) * 1989-05-24 1990-12-13 Laboratoire Theramex S.A. NOVEL METHODS FOR OBTAINING 6-METHYL 19-NOR STEROIDS AND CONVERTING THEM INTO 17α-SUBSTITUTED 19-NOR PREGNADIENES
FR2700548A1 (en) * 1993-01-20 1994-07-22 Roussel Uclaf New process for the preparation of alpha-methylated steroids

Families Citing this family (4)

* 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
US9267007B2 (en) 2005-09-16 2016-02-23 Grupo Petrotemex, S.A. De C.V. Method for addition of additives into a polymer melt
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

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1990015067A2 (en) * 1989-05-24 1990-12-13 Laboratoire Theramex S.A. NOVEL METHODS FOR OBTAINING 6-METHYL 19-NOR STEROIDS AND CONVERTING THEM INTO 17α-SUBSTITUTED 19-NOR PREGNADIENES
WO1990015067A3 (en) * 1989-05-24 1991-01-24 Theramex NOVEL METHODS FOR OBTAINING 6-METHYL 19-NOR STEROIDS AND CONVERTING THEM INTO 17α-SUBSTITUTED 19-NOR PREGNADIENES
GR900100394A (en) * 1989-05-24 1991-10-10 Theramex New methods for obtaining 6-methyl 19-nor steroides and their conversion in 19-nor pregnadienes 17-a substituted
FR2700548A1 (en) * 1993-01-20 1994-07-22 Roussel Uclaf New process for the preparation of alpha-methylated steroids
EP0608178A1 (en) * 1993-01-20 1994-07-27 Roussel Uclaf New 16-alpha steroid-methylation process
US5508452A (en) * 1993-01-20 1996-04-16 Roussel Uclaf Preparation of 16α-methyl steroids

Also Published As

Publication number Publication date
FR2014015B1 (en) 1976-09-17
NL6911623A (en) 1970-02-03
JPS505711B1 (en) 1975-03-06
BE736832A (en) 1970-01-30
JPS504657B1 (en) 1975-02-22
CH564564A5 (en) 1975-07-31
CH585767A5 (en) 1977-03-15
GB1277264A (en) 1972-06-07
GB1277267A (en) 1972-06-07
DE1938788A1 (en) 1970-02-12
CH594699A5 (en) 1978-01-31
FR2014015A1 (en) 1970-04-10
JPS504659B1 (en) 1975-02-22

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Legal Events

Date Code Title Description
PS Patent sealed
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
PE20 Patent expired after termination of 20 years