GB1214508A - 03-alkyl-11-oxygenated-18,19-dinorpregnenes - Google Patents

03-alkyl-11-oxygenated-18,19-dinorpregnenes

Info

Publication number
GB1214508A
GB1214508A GB27161/70A GB2716170A GB1214508A GB 1214508 A GB1214508 A GB 1214508A GB 27161/70 A GB27161/70 A GB 27161/70A GB 2716170 A GB2716170 A GB 2716170A GB 1214508 A GB1214508 A GB 1214508A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
oxo
protected
group
alkyl
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
GB27161/70A
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 GB1214508A publication Critical patent/GB1214508A/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)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,214,508. 13 - Alkyl - 11 - oxygenated - -18,- 19-dinor-pregnenes. AMERICAN HOME PRODUCTS CORP. 19 Dec., 1967 [19 Dec., 1966 (2)], No. 27161/70. Divided out of 1,214,506. Heading C2U. Novel steroids of the formula where W is a hydroxy, oxo, protected hydroxy or protected oxo group; Y is a hydroxy or protected hydroxy group and ring A is aromatic or Y is etherified hydroxy and there is a 2,5(10)- diene system or Y is protected oxo and there is a 4-, 5(10)- or 5-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; R<SP>1</SP> is alkyl of at least 2 carbon atoms and R<SP>2</SP> is hydroxy or protected hydroxy and X is α- or #-hydroxy or protected hydroxy or oxo or protected oxo, or R<SP>1</SP> is alkyl and X and R<SP>2</SP> together form an epoxy group; and corresponding novel steroids of the above formula wherein R<SP>1</SP> is ethyl or n-propyl, the 17#-side chain is replaced by a vinyl group, R<SP>2</SP> is OH, W is protected OH and Y is oxo and there is a 4-double bond; are prepared, in the case of the first-mentioned group, by oxidation of 17- ethylidene steroids followed, where the groups R<SP>2</SP>, X, W and Y and the unsaturation are not the ones required, by one or more appropriate after-processes, and, in the case of the secondmentioned group, by elimination of p-toluenesulphonic acid from a corresponding 17-(1<SP>1</SP>- tosyloxyethyl) compound. Figs. 1 and 2 illustrate 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. The 13#- enantiomers may be in resolved or racemate form according as to whether the starting materials are resolved or racemic. dl - 11# - Acetoxy - 13# - ethyl - 3 - methoxygona- 1,3,5(10)-trien-17-one is a by-product in the oxidation of dl - 11# - acetoxy - 3 - methoxy- 13# - ethyl - 18,19 - dinorpregna - 1,3,5(10),17- (20)-tetraene with N-methylmorpholine oxidehydrogen peroxide in presence of osmium tetroxide. The novel 13#-alkyl-11-substituted-18,19-dinorpregnenes of Formula (II) above, which have corticoidal and/or other hormonal activities and some of which have antimicrobial activity may be made up into pharmaceutical compositions with suitable carriers.
GB27161/70A 1966-12-19 1967-12-19 03-alkyl-11-oxygenated-18,19-dinorpregnenes Expired GB1214508A (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
GB1214508A true GB1214508A (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 After (2)

Application Number Title Priority Date Filing Date
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

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
US5083517A (en) * 1989-12-07 1992-01-28 Stevens Joel H Sod planting machine

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101652142B (en) * 2007-03-29 2013-01-02 Msd欧斯股份有限公司 Mineralocorticoid receptor antagonists

Cited By (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

Also Published As

Publication number Publication date
GB1214507A (en) 1970-12-02
GB1214506A (en) 1970-12-02

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Legal Events

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