GB1045979A

GB1045979A – Improvements in or relating to 5,10-seco-5,19-cyclo-10-fluoro-steroids
– Google Patents

GB1045979A – Improvements in or relating to 5,10-seco-5,19-cyclo-10-fluoro-steroids
– Google Patents
Improvements in or relating to 5,10-seco-5,19-cyclo-10-fluoro-steroids

Info

Publication number
GB1045979A

GB1045979A
GB33678/63A
GB3367863A
GB1045979A
GB 1045979 A
GB1045979 A
GB 1045979A
GB 33678/63 A
GB33678/63 A
GB 33678/63A
GB 3367863 A
GB3367863 A
GB 3367863A
GB 1045979 A
GB1045979 A
GB 1045979A
Authority
GB
United Kingdom
Prior art keywords
seco
cyclo
fluoro
dione
prepared
Prior art date
1962-08-28
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
GB33678/63A
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.)

Roche Palo Alto LLC

Original Assignee
Roche Palo Alto LLC
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.)
1962-08-28
Filing date
1963-08-26
Publication date
1966-10-19

1963-08-26
Application filed by Roche Palo Alto LLC
filed
Critical
Roche Palo Alto LLC

1966-10-19
Publication of GB1045979A
publication
Critical
patent/GB1045979A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

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

C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07J—STEROIDS

C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07J—STEROIDS

C07J67/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of two rings, each by one atom

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

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07J—STEROIDS

C07J75/00—Processes for the preparation of steroids in general

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

Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC

Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

Y10S435/00—Chemistry: molecular biology and microbiology

Y10S435/8215—Microorganisms

Y10S435/911—Microorganisms using fungi

Abstract

The invention comprises compounds of the formulae wherein R is hydrogen or a hydrocarbon carboxylic acyl radical of less than 12 carbon atoms which may be substituted; R1 is hydrogen, alkyl, alkenyl or alkynyl of at most 6 carbon atoms; Z is a single or double bond between C-1 and C-2 and Z1 is a single or double bond between C-6 and C-7, with at least one of Z and Z1 being a double bond; and Y is hydrogen, b -hydroxy or keto. The androstane derivatives are prepared by dehydrogenation of 5,10-seco – 5,19 – cyclo – 10b – fluoro – D 4 – androsten-17b -ol-3-one or the 17a -R1 homologues thereof. The D 1,4-compounds are prepared by refluxing these starting materials with selenium dioxide in t-butanol in the presence of pyridine or with 2,3 – dichloro – 5,6 -dicyano – 1,4 – benzoquinone, and on a second dehydrogenation with chloranil in t-butanol or with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, these are converted to the D 1,4,6-compounds. When the reaction with chloranil is effected first the D 4,6-compounds are obtained. The same starting materials or the corresponding 3,17-dione yield on reduction, preferably with lithium aluminium hydride in tetrahydrofuran, the corresponding 3,17-diols, which on dehydration with aqueous acetic acid at 75 DEG to 100 DEG C. yield the D 3,5-3-unsubstituted compounds. The pregnane derivatives of formulae are prepared by similar processes from 5,10-seco – 5,19 – cyclo – 10b – fluoro – D 4 – pregnene-3,20-dione, the 3,20-diols obtained in the reduction with lithium aluminium hydride being subsequently re-oxidized in the 20-position. The 17,21-dihydroxy-pregnane derivatives of formulae are prepared similarly from 21-monoesters of 5,10 – seco – 5,19 – cyclo – 10b – fluoro – D 4-pregnene – 17a ,21 – diol – 3,20 – dione which may be 11-substituted. Here, the side chain may also be protected as a 7,20:20,21-bismethylenedioxy group and 11b -ol products may be oxidized to the 11-ones. Elimination of the 21-hydroxy group from these products by conversion to the 21-tosylates and subsequent refluxing with sodium iodide in acetic acid gives products of the formulae All the free ols so produced may be esterified by standard procedures, a list of esterifying acids being provided. Examples are given. 5,10 – Seco – 5,19 – cyclo – 10b – fluoro – D 4 -pregnene – 11b ,17a ,21 – triol – 3,20 – dione 21- acetate is prepared by oxidizing 17,20:20,21-bismethylendioxy – 5,10 – seco – 5,19 – cyclo-10b – fluoro – D 4 – pregnene – 3b ,11b – diol to the corresponding 3-one, hydrolysing this to the free 11b ,17a ,21-triol-3,20-dione, and acetylating this.

GB33678/63A
1962-08-28
1963-08-26
Improvements in or relating to 5,10-seco-5,19-cyclo-10-fluoro-steroids

Expired

GB1045979A
(en)

Applications Claiming Priority (3)

Application Number
Priority Date
Filing Date
Title

MX6872962

1962-08-28

MX7010462

1962-12-10

MX7027362

1962-12-21

Publications (1)

Publication Number
Publication Date

GB1045979A
true

GB1045979A
(en)

1966-10-19

Family
ID=27350867
Family Applications (2)

Application Number
Title
Priority Date
Filing Date

GB33095/63A
Expired

GB1043995A
(en)

1962-08-28
1963-08-21
Improvements in or relating to 5,10-methylene-19-nor-steroids and 5,10-seco-5,19-cyclo-10-fluoro-steroids

GB33678/63A
Expired

GB1045979A
(en)

1962-08-28
1963-08-26
Improvements in or relating to 5,10-seco-5,19-cyclo-10-fluoro-steroids

Family Applications Before (1)

Application Number
Title
Priority Date
Filing Date

GB33095/63A
Expired

GB1043995A
(en)

1962-08-28
1963-08-21
Improvements in or relating to 5,10-methylene-19-nor-steroids and 5,10-seco-5,19-cyclo-10-fluoro-steroids

Country Status (4)

Country
Link

US
(4)

US3184485A
(en)

DE
(1)

DE1240857B
(en)

GB
(2)

GB1043995A
(en)

NL
(1)

NL297205A
(en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

NL297205A
(en)

*

1962-08-28

US3402186A
(en)

*

1964-02-24
1968-09-17
Abbott Lab
5beta, 19-cycloandrostanes

US3296270A
(en)

*

1964-11-13
1967-01-03
Syntex Corp
5, 10-methylene-19-nor-pregnanes and their preparation

US3458503A
(en)

*

1967-03-30
1969-07-29
American Home Prod
Preparation of 10beta-methyl-13-polycarbonalkyl-4-en-3-ones

BR112015028705B1
(en)

2013-06-13
2022-03-15
Ecolab Usa Inc

Water-free surface sizing composition, and method of treating a paper substrate

Family Cites Families (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

NL297205A
(en)

*

1962-08-28

0

NL
NL297205D
patent/NL297205A/xx
unknown

1963

1963-06-11
US
US286913A
patent/US3184485A/en
not_active
Expired – Lifetime

1963-06-11
US
US286914A
patent/US3246037A/en
not_active
Expired – Lifetime

1963-06-11
US
US286931A
patent/US3184484A/en
not_active
Expired – Lifetime

1963-06-11
US
US286912A
patent/US3185714A/en
not_active
Expired – Lifetime

1963-08-21
GB
GB33095/63A
patent/GB1043995A/en
not_active
Expired

1963-08-26
GB
GB33678/63A
patent/GB1045979A/en
not_active
Expired

1963-08-28
DE
DES86954A
patent/DE1240857B/en
active
Pending

Also Published As

Publication number
Publication date

NL297205A
(en)

US3185714A
(en)

1965-05-25

US3184484A
(en)

1965-05-18

GB1043995A
(en)

1966-09-28

US3246037A
(en)

1966-04-12

DE1240857B
(en)

1967-05-24

US3184485A
(en)

1965-05-18

Similar Documents

Publication
Publication Date
Title

US2816902A
(en)

1957-12-17

Hydroxylated steroids

GB1045979A
(en)

1966-10-19

Improvements in or relating to 5,10-seco-5,19-cyclo-10-fluoro-steroids

US3741997A
(en)

1973-06-26

Process for the preparation of pregnane derivatives

US3793350A
(en)

1974-02-19

Process for preparing 17alpha,21-dihydroxy-20-keto-pregnanes,derivatives and intermediates thereof

US3178412A
(en)

1965-04-13

Process for the production of 6beta-fluoro steroids

US2935511A
(en)

1960-05-03

Process of preparing 11 beta-hydroxy steroids

US3023206A
(en)

1962-02-27

Process for introducing delta unsaturation into steroids

US3014936A
(en)

1961-12-26

15-dehydro-cortical hormones

US3646012A
(en)

1972-02-29

Enamine salt protection of steroidal alpha beta-unsaturated ketones

GB855800A
(en)

1960-12-07

New cyclopentanophenanthrene derivatives and process for the production thereof

US3364236A
(en)

1968-01-16

3-keto-delta4-unsaturated-6-formyl steroids and process for the production thereof

US3168537A
(en)

1965-02-02

Process for the manufacture of 16-alkylidene-17alpha-alkanoyloxyprogesterones

US3155695A
(en)

1964-11-03

16-difluoromethyl adrenocorticoids

US3053858A
(en)

1962-09-11

10-fluoro-19-nor steroids

US3101355A
(en)

1963-08-20

Process for 3-keto-delta4,6 steroids

US3069413A
(en)

1962-12-18

16alpha-methyl pregnanes

GB1037772A
(en)

1966-08-03

Improvements in or relating to í¸-steroid compounds

GB843215A
(en)

1960-08-04

Improvements in or relating to steroid compounds

US3205226A
(en)

1965-09-07

19-nor-5(10)-dehydro steroids and methods for their manufacture

GB903049A
(en)

1962-08-09

Steroid compounds, preparation thereof and compositions thereof

GB811867A
(en)

1959-04-15

Dehydro-compounds of the steroid series and process of making same

GB950390A
(en)

1964-02-26

3ª,9ª-epoxy steroids of the androstane and pregnane series

US3414591A
(en)

1968-12-03

Novel method for producing 9beta, 10alpha-6-methylene testosterone

US3005817A
(en)

1961-10-24

12alpha-halo-delta20(22)-furostene-3beta, 26-diol-11-one 3, 26-diacylate and preparation thereof

US3089873A
(en)

1963-05-14

16alpha-alkoxycorticoids

Download PDF in English