GB1214507A - 03-alkyl-11-oxygenated-gonenes - Google Patents

03-alkyl-11-oxygenated-gonenes

Info

Publication number
GB1214507A
GB1214507A GB27160/70A GB2716070A GB1214507A GB 1214507 A GB1214507 A GB 1214507A GB 27160/70 A GB27160/70 A GB 27160/70A GB 2716070 A GB2716070 A GB 2716070A GB 1214507 A GB1214507 A GB 1214507A
Authority
GB
United Kingdom
Prior art keywords
protected
alkyl
oxo
group
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
GB27160/70A
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 GB1214507A publication Critical patent/GB1214507A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
    • 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
    • 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
    • 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
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • 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

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Steroid Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,214,507. 13 - Alkyl - 11 - oxygenated - gonenes. AMERICAN HOME PRODUCTS CORP. 19 Dec., 1967 [19 Dec., 1966 (2)], No. 27160/70. Divided out of 1,214,506. Heading C2U. A 13# - alkyl - 17# - ethyl - 11 - oxygenatedgona - 1,3,5(10) - trien - 17# - ol or a 13#- alkyl - 17 - ethylidene - 11 - oxygenated gonane having further unsaturation in ring A is prepared by (a) hydroborating a 3-hydroxy or protected hydroxy 13#-alkyl-17#-ethyl-gona- 1,3,5(10),9(11) - tetraen - 17# - ol to give a corresponding 13# - alkyl - 17# - ethylgona - 1,- 3,5(10)-trien-11,17#-diol, if desired protecting the generated 11-hydroxy group by conversion to an 11-oxo group or a protected hydroxy or oxo group and if desired dehydrating the 11- protected compound to give a 13#-alkyl-11- oxygenated - 17 - ethylidene - gona - 1,3,5(10)- triene. In these products, a protecting group may be removed, an 11α-hydroxy group epimerized or oxidized, a 3-alkoxy-gona-1,3,5(10)- triene Birch reduced and hydrolysed to give a 4-en-3-one or 5(10)-en-3-one, a 3-oxo group protected, an 11-hydroxy group re-protected, or a 3-alkoxy group formed from a 3-hydroxy group or a 3-protected hydroxy group other than a 3-alkoxy group. Novel products have the formula where Y is OH or protected OH and ring A is aromatic or Y is etherified OH and there is a 2,5(10)- diene system, or Y is protected oxo and there is a 4-, 5(6)- or 5(10)-double bond with or without a 2- or 3-double bond, or Y is oxo and there is a 4- or 5(10)-double bond, and (a) R<SP>1</SP> is alkyl, R<SP>2</SP> and R<SP>3</SP> together are ethylidene, and W is α- or #-OH or protected OH or oxo or protected oxo; or (b) R<SP>1</SP> is alkyl other than CH 3 , R<SP>2</SP> is OH or protected OH, R<SP>3</SP> is ethyl, and W is as in (a); or (c) R<SP>1</SP> is CH 3 , R<SP>2</SP> and R<SP>3</SP> are as in (b), and W is α- or #-alkoxy. Fig. 1 illustrates the invention in its preferred embodiments. The protecting groups are those known in the art which are readily convertible, e.g. by hydrolysis, to free hydroxy or oxo groups. In the process the steroid nucleus can contain further substituents other than those specified. The 13#-enantiomers may be in resolved or racemate form according as to whether the starting materials are resolved or racemic. The novel 13#-alkyl-11-oxygenated-gonenes have steroid hormone and anti-microbiological activity and they may be made up into pharmaceutical compositions with suitable carriers.
GB27160/70A 1966-12-19 1967-12-19 03-alkyl-11-oxygenated-gonenes Expired GB1214507A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US60278566A 1966-12-19 1966-12-19
US60276366A 1966-12-19 1966-12-19

Publications (1)

Publication Number Publication Date
GB1214507A true GB1214507A (en) 1970-12-02

Family

ID=27084237

Family Applications (3)

Application Number Title Priority Date Filing Date
GB27161/70A Expired GB1214508A (en) 1966-12-19 1967-12-19 03-alkyl-11-oxygenated-18,19-dinorpregnenes
GB57494/67A Expired GB1214506A (en) 1966-12-19 1967-12-19 03-alkyl-3,11,17,20,21-pentaoxygenated-18,19-dinopregnenes and their derivatives
GB27160/70A Expired GB1214507A (en) 1966-12-19 1967-12-19 03-alkyl-11-oxygenated-gonenes

Family Applications Before (2)

Application Number Title Priority Date Filing Date
GB27161/70A Expired GB1214508A (en) 1966-12-19 1967-12-19 03-alkyl-11-oxygenated-18,19-dinorpregnenes
GB57494/67A Expired GB1214506A (en) 1966-12-19 1967-12-19 03-alkyl-3,11,17,20,21-pentaoxygenated-18,19-dinopregnenes and their derivatives

Country Status (1)

Country Link
GB (3) GB1214508A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010522732A (en) * 2007-03-29 2010-07-08 ナームローゼ・フエンノートチヤツプ・オルガノン Mineralocorticoid receptor antagonist

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5083517A (en) * 1989-12-07 1992-01-28 Stevens Joel H Sod planting machine

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010522732A (en) * 2007-03-29 2010-07-08 ナームローゼ・フエンノートチヤツプ・オルガノン Mineralocorticoid receptor antagonist

Also Published As

Publication number Publication date
GB1214508A (en) 1970-12-02
GB1214506A (en) 1970-12-02

Similar Documents

Publication Publication Date Title
GB1242194A (en) A new oestratriol and a process for its manufacture
GB1190403A (en) 4-Hydroxy-2-Butenoic Acid Lactones
GB1040554A (en) The manufacture of 3-keto-19-alkyl-steroids
GB1214507A (en) 03-alkyl-11-oxygenated-gonenes
GB1211220A (en) 21-aldehydes of the pregnane series and derivatives thereof and process for their manufacture
GB1495531A (en) 11beta-alkyl steroids of the estrane series
GB1158332A (en) New 7alpha-Methyl-19-Nor-Androstadienes and process for their Manufacture
GB1502326A (en) 11-substituted steroids of the estrane series
GB1277266A (en) 07-acetylgonanes and derivatives therefor
GB1190404A (en) 4,4-Dihydroxy-2-Butenoic Acid Lactones
GB1504410A (en) 11beta-fluoroandrostenes
GB1211836A (en) Novel 15,16-alkylidene-steroids and a process for the manufacture thereof
GB1323775A (en) Cardenolide-and bufadienolide-3-2,3-didesoxyglycosides and processes for their preparation
GB1514621A (en) 13-ethynyl-and 13-(2-halovinyl)-steroids and their preparation
GB1383334A (en) 15alpha,16alpha-methylene-steroids
GB1185381A (en) 05,16beta-Methylene Steroids of the 19-Nor-Androstane Series and Process for their Manufacture
ES290864A1 (en) Novel steroid esters, their preparation and employment
GB1272688A (en) Sulphamido-steroids and the preparation thereof
GB1263383A (en) 6-fluoro steroids of the androstane series and their manufacture
GB1311725A (en) 18-cyano pregnane compounds and process for their manufacture
GB1242372A (en) A new oestratriol and a process for its manufacture
GB1089916A (en) Novel 17-alkyl-19-nor-steroids
ES361690A1 (en) 18-methylene-steroids of the pregnane series
GB1128044A (en) 13-(c) alkyl-11-oxygenated gonenes
GB1162769A (en) Delta&lt;,5&gt;-7alpha-Methyl-Estradienes and their preparation

Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees