GB1341601A - 4,14-estradiene compounds - Google Patents

4,14-estradiene compounds

Info

Publication number
GB1341601A
GB1341601A GB1160271*[A GB1160271A GB1341601A GB 1341601 A GB1341601 A GB 1341601A GB 1160271 A GB1160271 A GB 1160271A GB 1341601 A GB1341601 A GB 1341601A
Authority
GB
United Kingdom
Prior art keywords
compounds
prepared
dehydro
cor
april
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
GB1160271*[A
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.)
Ochsner Alton Medical Foundation
Original Assignee
Ochsner Alton Medical Foundation
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 Ochsner Alton Medical Foundation filed Critical Ochsner Alton Medical Foundation
Publication of GB1341601A publication Critical patent/GB1341601A/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
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A61K31/567—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in position 17 alpha, e.g. mestranol, norethandrolone
    • 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
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • 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
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A61K31/566—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol having an oxo group in position 17, e.g. estrone
    • 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
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Steroid Compounds (AREA)

Abstract

1341601 4,14-Estradienes ALTON OCHSNER MEDICAL FOUNDATION 27 April 1971 [28 April 1970 5 Feb 1971] 11602/71 Heading C2U The invention comprises compounds of formula wherein R is H or Me and R<SP>1</SP> is H or COR<SP>11</SP>, where R<SP>11</SP> is C 1-10 alkyl, C 6-15 aryl (optionally substituted by one or more C 1-7 alkyl groups), C 3-8 cycloalkyl or C 7-15 aralkyl (optionally substituted on the aryl ring by one or more C 1-7 alkyl groups). Compound I (R = R<SP>1</SP> H) is prepared from estrone 3-methyl ether (II) by the sequence: II -# 16α - bromo - II -# 14 - dehydro - II (+15 - dehydro - 14 - epi - II by-product) -# 14 - dehydroestradiol 3 - methyl ether -# 3- methoxyestra - 2,5(10),14 - trien - 17# - ol -# the #<SP>5(10)</SP>-isomer of I -# I. The penultimate product may not be isolated. Compound I (R=Me, R<SP>1</SP>=H) is prepared analogously. Compounds I (R<SP>1</SP> = COR<SP>11</SP>) are prepared by conventional esterification of I (R<SP>1</SP> = H). Compounds I are said to possess anabolic and androgenic activity, and may be made up with carriers into pharmaceutical compositions for oral and parenteral administration.
GB1160271*[A 1970-04-28 1971-04-27 4,14-estradiene compounds Expired GB1341601A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US3272370A 1970-04-28 1970-04-28

Publications (1)

Publication Number Publication Date
GB1341601A true GB1341601A (en) 1973-12-25

Family

ID=21866473

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1160271*[A Expired GB1341601A (en) 1970-04-28 1971-04-27 4,14-estradiene compounds

Country Status (2)

Country Link
GB (1) GB1341601A (en)
ZA (1) ZA712312B (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001005806A1 (en) * 1999-07-16 2001-01-25 Akzo Nobel N.V. Orally active androgens
WO2002048169A1 (en) * 2000-12-15 2002-06-20 Akzo Nobel N.V. 14(15)-unsaturated 15- and/or 16- substituted androgens with mixed androgen-progestational profile
WO2003045398A1 (en) * 2001-03-30 2003-06-05 The Government Of The United States Of America, Represented By The Secretary, Department Of Health And Human Services Methods of making and pharmaceutical formulations comprising 7alpha, 11beta-dimethy-17beta-hydroxyestra-4, 14-dien-3-one and 17 esters thereof
US7196074B2 (en) 2000-03-31 2007-03-27 The United States Of America As Represented By The Department Of Health And Human Services Methods of making, using and pharmaceutical formulations comprising 7α, 11β-dimethyl-17β-hydroxyestra-4, 14-dien-3-one and 17 esters thereof
US7696190B2 (en) 2000-07-28 2010-04-13 N.V. Organon 16Alpha-methyl or ethyl substituted estrogens
US7838516B2 (en) 2004-09-08 2010-11-23 N.V. Organon 15 β-substituted steroids having selective estrogenic activity
US10351587B2 (en) 2000-03-31 2019-07-16 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Method of making and using 7α, 11β-dimethyl-17β-hydroxyestr-4-en-3-one 17-undecanoate

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001005806A1 (en) * 1999-07-16 2001-01-25 Akzo Nobel N.V. Orally active androgens
US6313108B1 (en) 1999-07-16 2001-11-06 Akzo Nobel N.V. Orally active androgens
US6541465B2 (en) * 1999-07-16 2003-04-01 Akzo Nobel N.V. Orally active androgens
AU770412B2 (en) * 1999-07-16 2004-02-19 Akzo Nobel N.V. Orally active androgens
US6780854B2 (en) 1999-07-16 2004-08-24 Akzo Nobel Nv Orally active androgens
US7196074B2 (en) 2000-03-31 2007-03-27 The United States Of America As Represented By The Department Of Health And Human Services Methods of making, using and pharmaceutical formulations comprising 7α, 11β-dimethyl-17β-hydroxyestra-4, 14-dien-3-one and 17 esters thereof
US10351587B2 (en) 2000-03-31 2019-07-16 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Method of making and using 7α, 11β-dimethyl-17β-hydroxyestr-4-en-3-one 17-undecanoate
US7696190B2 (en) 2000-07-28 2010-04-13 N.V. Organon 16Alpha-methyl or ethyl substituted estrogens
WO2002048169A1 (en) * 2000-12-15 2002-06-20 Akzo Nobel N.V. 14(15)-unsaturated 15- and/or 16- substituted androgens with mixed androgen-progestational profile
WO2003045398A1 (en) * 2001-03-30 2003-06-05 The Government Of The United States Of America, Represented By The Secretary, Department Of Health And Human Services Methods of making and pharmaceutical formulations comprising 7alpha, 11beta-dimethy-17beta-hydroxyestra-4, 14-dien-3-one and 17 esters thereof
US7838516B2 (en) 2004-09-08 2010-11-23 N.V. Organon 15 β-substituted steroids having selective estrogenic activity

Also Published As

Publication number Publication date
ZA712312B (en) 1972-01-26

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Legal Events

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