GB1078478A

GB1078478A – New 3-amino-a-nor-b-homo-steroids and process for their manufacture
– Google Patents

GB1078478A – New 3-amino-a-nor-b-homo-steroids and process for their manufacture
– Google Patents
New 3-amino-a-nor-b-homo-steroids and process for their manufacture

Info

Publication number
GB1078478A

GB1078478A
GB46053/65A
GB4605365A
GB1078478A
GB 1078478 A
GB1078478 A
GB 1078478A
GB 46053/65 A
GB46053/65 A
GB 46053/65A
GB 4605365 A
GB4605365 A
GB 4605365A
GB 1078478 A
GB1078478 A
GB 1078478A
Authority
GB
United Kingdom
Prior art keywords
group
homo
methyl
steroids
steroid
Prior art date
1964-11-12
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
GB46053/65A
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.)

BASF Schweiz AG

Original Assignee
Ciba AG
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.)
1964-11-12
Filing date
1965-11-01
Publication date
1967-08-09

1965-11-01
Application filed by Ciba AG
filed
Critical
Ciba AG

1967-08-09
Publication of GB1078478A
publication
Critical
patent/GB1078478A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07J—STEROIDS

C07J69/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by contraction of only one ring by one atom and expansion of only one ring by one atom

Abstract

Novel A-nor-B-homo-steroids of the formula and their salts (wherein R1 is hydrogen or methyl, R2 is an aliphatic hydrocarbon group of 8 to 10 carbon atoms; and Z is a substituted or unsubstituted amino group) are prepared by reacting a corresponding compound containing in the 3-position a reactive esterified hydroxyl group with ammonia or a primary or secondary amine or with a donor of such compounds, or by reducing corresponding compounds containing in the 3-position a group reducible to an amino group, and, if desired, substituting a resulting 3-amino group in known manner. Substituents in the 3-amino group may be, in particular, alkyl, alkoxyalkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aralkyl groups, or alkylene groups which may be interrupted by heteroatoms, thus forming a saturated, nitrogen-containing heterocyclic ring, e.g. pyrrolidino, piperidino, morpholino, thiamorpholino, piperazino, N-methyl-piperazino, or N-(b -hydroxyethyl)-piperazino, or acyl radicals. R2 is, in particular, a 6-methyl-heptyl-(2), 5,6-dimethylheptyl-(2) or 5-ethyl-6-methyl-heptyl-(2) group or such a group containing a 3,4-double bond. The 3-substituent in the starting materials is preferably a halogen atom or a hydrocarbonsulphonyloxy group, or a hydroxyimino, nitro, nitroso, imino or tautomeric enamino, or an azido group. Amino substituents may be introduced, for example, by reaction with a reactive ester of a suitable alcohol, or by reductive alkylation. A-nor-B-homo-steroid starting materials containing a 3-reactive, esterified hydroxyl group are prepared by u.v. irradiation of a suitable 3-oxo-4,5-oxido-steroid, acylating the 3,6-dioxo-A-nor-B-homo-steroid formed (which is predominantly present in the enol form), and hydrogenating the resulting D 5-3-oxo-6-acyloxy-A-nor-B-homo-steroid. The resulting 6-unsubstituted 3-oxo-A-nor-B-homo-steroids are then reduced and esterified. They may also be reacted with hydroxylamine or an amine to give 3-imino compounds. The A-nor-B-homo-steroids of the invention, which are stated to be tuberculostatic and anti-tumour agents, may be added to feedstuffs or made up into preparations for pharmaceutical or veterinary use with suitable carriers.

GB46053/65A
1964-11-12
1965-11-01
New 3-amino-a-nor-b-homo-steroids and process for their manufacture

Expired

GB1078478A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

CH1463364

1964-11-12

Publications (1)

Publication Number
Publication Date

GB1078478A
true

GB1078478A
(en)

1967-08-09

Family
ID=4402515
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB46053/65A
Expired

GB1078478A
(en)

1964-11-12
1965-11-01
New 3-amino-a-nor-b-homo-steroids and process for their manufacture

Country Status (7)

Country
Link

US
(1)

US3459769A
(en)

AT
(2)

AT267085B
(en)

BE
(1)

BE672157A
(en)

ES
(1)

ES319417A1
(en)

FR
(2)

FR5028M
(en)

GB
(1)

GB1078478A
(en)

NL
(1)

NL6514667A
(en)

0

BE
BE672157D
patent/BE672157A/xx
unknown

1965

1965-10-23
US
US504116A
patent/US3459769A/en
not_active
Expired – Lifetime

1965-11-01
GB
GB46053/65A
patent/GB1078478A/en
not_active
Expired

1965-11-10
ES
ES0319417A
patent/ES319417A1/en
not_active
Expired

1965-11-11
AT
AT610966A
patent/AT267085B/en
active

1965-11-11
AT
AT1018465A
patent/AT267083B/en
active

1965-11-11
NL
NL6514667A
patent/NL6514667A/xx
unknown

1966

1966-02-01
FR
FR47932A
patent/FR5028M/fr
not_active
Expired

1966-02-01
FR
FR47933A
patent/FR5102M/fr
not_active
Expired

Also Published As

Publication number
Publication date

AT267085B
(en)

1968-12-10

ES319417A1
(en)

1966-06-01

AT267083B
(en)

1968-12-10

BE672157A
(en)

FR5028M
(en)

1967-04-24

NL6514667A
(en)

1966-05-13

US3459769A
(en)

1969-08-05

FR5102M
(en)

1967-05-22

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