Patent US4342702A successfully refreshed from Google Patents.
US4342702A
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Metallated halogenated acetylene corticoid synthesis
Assignee: Pharmacia and Upjohn Co
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Filing: 1981-05-18
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Granted: 1982-08-03
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Expires: 2001-05-18
Abstract
Abstract A process for the preparation of corticoids (IX) which comprises reacting a 17-keto steroid (I) with a metallated halogenated acetylene (II) followed by reaction with a sulfenylating agent (IV) and C 17 side chain rearrangement.
Inventors
- 👤 Jerry A. Walker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 14:37
CPC Classifications
C; C07; C07J; C07J31/00; C07J31/006; C07J1/00; C07J1/0003; C07J1/0033; C07J5/00; C07J5/0046; C07J5/0053; C07J7/00; C07J7/008; C07J7/0085
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
26 words
A 21-halo allene sulfoxide of the formula: where A, R 6 , R 9 , R 11 , R 16 , R 22 , ˜ and
Claim 2
Dependent Claim
26 words
A 21-halo allene sulfoxide of the formula: where A, R 6 , R 9 , R 11 , R 16 , R 22 , ˜ and
Claim 3
Dependent Claim
13 words
A 21-halo allene sulfoxide according to claim 1 where R 6 is a
Claim 4
Dependent Claim
13 words
A 21-halo allene sulfoxide according to claim 1 where R 16 is a
Claim 5
Dependent Claim
28 words
A 21-halo allene sulfoxide according to claim 1 where R 9 is nothing and R 11 is [H] which gives a Δ 9 (11) functionality in the C
Claim 6
Dependent Claim
13 words
A 21-halo allene sulfoxide according to claim 1 where A is a chlorine
Claim 7
Dependent Claim
12 words
A 21-halo allene sulfoxide according to claim 1 where R 22 is
Claim 8
Dependent Claim
10 words
A 21-halo allene sulfoxide according to claim 1 which is
Claim 9
Dependent Claim
59 words
A process for the preparation of a 21-halo allene sulfoxide of the formula: ##STR2## which comprises contacting a 17α-haloethynyl steroid of the formula: ##STR3## with a sulfenylating agent of the formula: R.sub.22 --S--X (IV) where A, R 6 , R 9 , R 11 , R 16 , R 22 , X, ˜ and are defined in the specification.
Claim 10
Dependent Claim
59 words
A process for the preparation of a 21-halo allene sulfoxide of the formula: ##STR2## which comprises contacting a 17α-haloethynyl steroid of the formula: ##STR3## with a sulfenylating agent of the formula: R.sub.22 --S--X (IV) where A, R 6 , R 9 , R 11 , R 16 , R 22 , X, ˜ and are defined in the specification.
Claim 11
Dependent Claim
19 words
A process according to claim 8 where R 22 is phenyl and X is a chlorine or bromine atom.
Claim 12
Dependent Claim
13 words
A process according to claim 8 where R 6 is a hydrogen atom.
Claim 13
Dependent Claim
13 words
A process according to claim 8 where R 16 is a hydrogen atom.
Claim 14
Dependent Claim
27 words
A process according to claim 8 where R 9 is nothing and R 11 is [H] which gives a Δ 9 (11) functionality in the C ring.
Claim 15
Dependent Claim
14 words
A process according to claim 8 where the 21-halo allene sulfoxide (V) is 21-chloro-21-(phenylsulfinyl)pregna-4,9(11),17(20),20-tetraen-3-one.
Claim 16
Dependent Claim
72 words
A process for the preparation of a sulfoxide of the formula: ##STR4## which comprises (1) contacting a 21-halo allene sulfoxide of the formula: ##STR5## with a base selected from the group consisting of OR 20 and SR 20 and (2) quenching with an acid where A, R 6 , R 9 , R 11 , R 16 , R 20 , R 22 , Z, ˜ and are defined in the specification.
Claim 17
Dependent Claim
72 words
A process for the preparation of a sulfoxide of the formula: ##STR4## which comprises (1) contacting a 21-halo allene sulfoxide of the formula: ##STR5## with a base selected from the group consisting of OR 20 and SR 20 and (2) quenching with an acid where A, R 6 , R 9 , R 11 , R 16 , R 20 , R 22 , Z, ˜ and are defined in the specification.
Claim 18
Dependent Claim
14 words
A process according to claim 14 where the base is methoxide, ethoxide or phenoxide.
Claim 19
Dependent Claim
13 words
A process according to claim 14 where 1.0 equivalents of base are used.
Claim 20
Dependent Claim
28 words
A process according to claim 14 where the acid is selected from the group consisting of p-TSA, hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid or formic acid.
Claim 21
Dependent Claim
13 words
A process according to claim 14 where R 6 is a hydrogen atom.
Claim 22
Dependent Claim
13 words
A process according to claim 14 where R 16 is a hydrogen atom.
Claim 23
Dependent Claim
27 words
A process according to claim 14 where R 9 is nothing and R 11 is [H], which gives a Δ 9 (11) functionality in the C ring.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-08-02 | 1986-02-01 | 1986-08-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-08-02 | 1990-02-01 | 1990-08-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-08-02 | 1994-02-01 | 1994-08-03 | $7700.00 | Window Closed / Lapsed |