GB1062813A - Improvements in or relating to steroids and the manufacture thereof - Google Patents

Improvements in or relating to steroids and the manufacture thereof

Info

Publication number
GB1062813A
GB1062813A GB1077464A GB1077464A GB1062813A GB 1062813 A GB1062813 A GB 1062813A GB 1077464 A GB1077464 A GB 1077464A GB 1077464 A GB1077464 A GB 1077464A GB 1062813 A GB1062813 A GB 1062813A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
carbon atoms
inclusive
hydroxy
free bases
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
GB1077464A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
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
Priority claimed from US278442A external-priority patent/US3178409A/en
Application filed by Upjohn Co filed Critical Upjohn Co
Publication of GB1062813A publication Critical patent/GB1062813A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/18—Ring systems of four or more rings
    • 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
    • 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
    • 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
    • A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (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)
  • Steroid Compounds (AREA)

Abstract

Novel compounds selected from the class consisting of: (a) the free bases having the formulae <FORM:1062813/C2/1> <FORM:1062813/C2/2> <FORM:1062813/C2/3> wherein R is hydrogen, fluorine or methyl, R1 is hydrogen, an aliphatic hydrocarbon radical containing 1-8 carbon atoms, inclusive, aralkyl containing from 7-13 carbon atoms, inclusive, or aryl containing from 6-12 carbon atoms, inclusive, R11 is hydrogen, or the acyl radical of a hydrocarbon carboxylic acid containing from 1-12 carbon atoms, inclusive, W is hydrogen or fluorine, X1 is hydrogen, keto, or a - or b -hydroxy, and X1 and W taken together represent a 9(11)-double bond, X is hydrogen, keto, a -hydroxy, b -hydroxy, or a 9(11)-double bond, Y is hydrogen, hydroxy or acyloxy wherein acyl is as hereinbefore defined, Z is hydrogen or methyl, and -C1-C2- is selected from the class consisting of -CH = CH- and -CH2-CH2-; (b) the acid addition salts of the free bases having the above formulae; (c) the N-oxides and N-oxide acid addition salts of those free bases of the above formulae wherein R1 is other than hydrogen; and (d) the quaternary ammonium salts of those free bases of the above formulae wherein R1 is other than hydrogen; the corresponding compounds having in ring D the following configuration: <FORM:1062813/C2/4> and a compound having the general formula <FORM:1062813/C2/5> wherein R, R1, R11, and X1 are as defined above and Q is hydrogen or fluorine and derivatives thereof as in (b), (c) and (d) above, are obtained by reacting a 16a -(2-oxo-ethyl)-17-isopregnane having in ring D the following configuration: <FORM:1062813/C2/6> wherein Y is hydrogen or acyloxy wherein the acyl radical is that of a hydrocarbon carboxylic acid containing 1-12 carbon atoms, inclusive, with a primary amine R1-NH2 wherein R1 is hydrogen, an aliphatic hydrocarbon radical containing 1-8 carbon atoms inclusive, aralkyl containing from 7-13 carbon atoms inclusive or aryl containing 6-12 carbon atoms inclusive to obtain the corresponding 11,41-dihydroandrostano-[17,16a -C]-pyridine, and if desired optionally dehydrogenating this compound to obtain the compounds having in ring D the following configuration <FORM:1062813/C2/7> or hydrogenating to obtain the saturated piperidine derivative. Pharmaceutical compositions having anti-inflammatory activity, progestational, central nervous system regulating, glucocorticoid, anti-hormonal, lipid-mobilizing, hypotensive, cardiotonic, cholesterol-lowering activity and containing the above compounds are administered orally or parenterally.
GB1077464A 1963-05-06 1964-03-13 Improvements in or relating to steroids and the manufacture thereof Expired GB1062813A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US278442A US3178409A (en) 1963-05-06 1963-05-06 1', 4'-dihydroandrostano-[17, 16alpha-c]-pyridines and derivatives thereof

Publications (1)

Publication Number Publication Date
GB1062813A true GB1062813A (en) 1967-03-22

Family

ID=23064990

Family Applications (2)

Application Number Title Priority Date Filing Date
GB4103166A Expired GB1062814A (en) 1963-05-06 1964-03-13 Improvements in or relating to steroids and the manufacture thereof
GB1077464A Expired GB1062813A (en) 1963-05-06 1964-03-13 Improvements in or relating to steroids and the manufacture thereof

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB4103166A Expired GB1062814A (en) 1963-05-06 1964-03-13 Improvements in or relating to steroids and the manufacture thereof

Country Status (5)

Country Link
CH (1) CH444858A (en)
DE (2) DE1593656A1 (en)
FR (1) FR1561910A (en)
GB (2) GB1062814A (en)
NL (1) NL6404998A (en)

Also Published As

Publication number Publication date
CH444858A (en) 1967-10-15
GB1062814A (en) 1967-03-22
DE1593656A1 (en) 1970-11-26
FR1561910A (en) 1969-04-04
DE1250820B (en) 1967-09-28
NL6404998A (en) 1964-11-09

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