GB1152450A

GB1152450A – Improvements in or relating to 3-Desoxy-16-Methylene-Pregnenes and Pregnadienes
– Google Patents

GB1152450A – Improvements in or relating to 3-Desoxy-16-Methylene-Pregnenes and Pregnadienes
– Google Patents
Improvements in or relating to 3-Desoxy-16-Methylene-Pregnenes and Pregnadienes

Info

Publication number
GB1152450A

GB1152450A
GB45404/66A
GB4540466A
GB1152450A
GB 1152450 A
GB1152450 A
GB 1152450A
GB 45404/66 A
GB45404/66 A
GB 45404/66A
GB 4540466 A
GB4540466 A
GB 4540466A
GB 1152450 A
GB1152450 A
GB 1152450A
Authority
GB
United Kingdom
Prior art keywords
compounds
methylene
converting
acylates
epoxides
Prior art date
1965-10-22
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
GB45404/66A
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.)
1965-10-22
Filing date
1966-10-11
Publication date
1969-05-21

1966-10-11
Application filed by Roche Palo Alto LLC
filed
Critical
Roche Palo Alto LLC

1969-05-21
Publication of GB1152450A
publication
Critical
patent/GB1152450A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

Classifications

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

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

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

Abstract

1,152,450. 3 – Desoxy – 16 – methylene – pregnane compounds. SYNTEX CORP. 11 Oct., 1966 [22 Oct., 1965], No. 45404/66. Heading C2U. Novel steroids of the formula (wherein R is H or CH 3 ; R1 is H, Cl or F; R2 is H or acyl; R3 is H, CH 3 , Cl or F; and Z is an optional #6 double bond) are prepared from #5,16-pregnadien-3#-ol-20-one or the 19-nor compound by either oxidizing to the #4-3-ones, converting these via the 16α,17α-pyrazolines to the 16-methyl compounds, converting these to the 16α,17α-epoxides and splitting these to give the 16-methylene-17α-ols or their acylates or by converting the starting materials via their 5α,6α-epoxides, the 20-keto group being protected by ketalization, to the 5α-hydroxy-6#- methyl, chloro or fluoro compounds, removing the ketal protecting group, converting to the 16-methylene-17α-ols or their acylates via the 16-methyl and 16α,17α-epoxy compounds and oxidizing the products to give the 6-substituted #4-3-ones, the 3-keto group then being removed from these and the 6-unsubstituted compounds via the #4– or A4‘6-3-thioketals (the #6 double bond having been previously introduced). 21-Halo substituents may be introduced at any stage via the 21-iodo compounds and, optionally, the 21-acetates and 21-mesylates. 17-Acylates may be prepared directly in the 16α, 17α-epoxide splitting stage or subsequently by direct acylation, any 3-enol acylates formed being hydrolysed. A 6-halo substituent may also be introduced into the 16-methylene-#4,6-3-ones via the 6α, 7α-epoxides and 6α-halo-7α-hydroxy compounds, the 3-keto group being subsequently removed via the #4‘6-3-thioketals.

GB45404/66A
1965-10-22
1966-10-11
Improvements in or relating to 3-Desoxy-16-Methylene-Pregnenes and Pregnadienes

Expired

GB1152450A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

US502274A

US3284476A
(en)

1965-10-22
1965-10-22
3-unsubstituted, 16-methylene pregnenes and pregnadienes

Publications (1)

Publication Number
Publication Date

GB1152450A
true

GB1152450A
(en)

1969-05-21

Family
ID=23997090
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB45404/66A
Expired

GB1152450A
(en)

1965-10-22
1966-10-11
Improvements in or relating to 3-Desoxy-16-Methylene-Pregnenes and Pregnadienes

Country Status (2)

Country
Link

US
(1)

US3284476A
(en)

GB
(1)

GB1152450A
(en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US3493588A
(en)

*

1968-03-25
1970-02-03
Schering Corp
Process for the preparation of 6-chloro-16-methylene – 17alpha – lower alkanoyloxy-4,6-pregnadiene-3,20-dione and novel intermediates produced thereby

US3493562A
(en)

*

1968-03-25
1970-02-03
Schering Corp
6alpha,7alpha;16alpha,17alpha – bis – oxido – 16beta – methyl-4-pregnene – 3,20 – dione and method for its manufacture

Family Cites Families (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

US3186985A
(en)

*

1963-05-07
1965-06-01
Schering Corp
Novel 6-keto-4-dehydro-steroids and processes for their manufacture

1965

1965-10-22
US
US502274A
patent/US3284476A/en
not_active
Expired – Lifetime

1966

1966-10-11
GB
GB45404/66A
patent/GB1152450A/en
not_active
Expired

Also Published As

Publication number
Publication date

US3284476A
(en)

1966-11-08

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Legal Events

Date
Code
Title
Description

1969-10-01
PS
Patent sealed [section 19, patents act 1949]

1977-05-11
PLNP
Patent lapsed through nonpayment of renewal fees

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