US4455430A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for preparing tricholomic acid and derivatives thereof
Assignee: Pharmacia and Upjohn Co
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Filing: 1981-01-28
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Granted: 1984-06-19
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Expires: 2001-01-28
Abstract
Abstract Chemical process for preparing tricholomic acid and its analogs which are useful for the preparation of AT-125.
Inventors
- 👤 Robert C. Kelly
- 👤 Wendell Wierenga
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 01:19
CPC Classifications
C; C07; C07D; C07D413/00; C07D413/02; C07D413/06; A; A47; A47G; A47G33/00
Claims Analysis
Total Claims: 3
Claim 1
Independent Claim
380 words
A process for preparing racemic mixtures and optically active isomers of compounds having the formula ##STR88## which comprises the deprotection of racemic mixtures and optically active isomers of compounds having the formula ##STR89## wherein R is selected from the group consisting of hydrogen, alkyl of from 1 to 12 carbon atoms, inclusive, halogenated alkyl of from 1 to 5 carbon atoms, inclusive, and 1 to 3 halogen atoms, inclusive, aryl of from 6 to 20 carbon atoms, inclusive, aralkyl of from 7 to 20 carbon atoms, inclusive, and substituted aralkyl of from 7 to 20 carbon atoms inclusive; R' 13 is selected from the group ##STR90## wherein R' 6 is alkyl of from 1 to 8 carbon atoms, inclusive, halogenated alkyl of from 1 to 5 carbon atoms, inclusive, and 1 to 3 halogen atoms, and aralkyl of from 7 to 20 carbon atoms, inclusive, R 14 and R 15 are selected from the group consisting of hydrogen, ##STR91## or when taken together with the nitrogen form the group ##STR92## wherein R 6 is alkyl of from 1 to 8 carbon atoms, inclusive, halogenated alkyl of from 1 to 5 carbon atoms, inclusive, and 1 to 3 halogen atoms, inclusive, aralkyl of from 7 to 20 carbon atoms, inclusive, and substituted aralkyl of from 7 to 20 carbon atoms, inclusive, R 7 is selected from the group consisting of alkyl of from 1 to 12 carbon atoms, inclusive, aryl of from 6 to 20 carbon atoms, inclusive, aralkyl of from 7 to 20 carbon atoms, inclusive, and substituted aralkyl of from 7 to 20 carbon atoms, inclusive, and R 8 is selected from the group consisting of ##STR93## Where R 9 , R 10 , R 11 and R 12 are selected from the group consisting of hydrogen and alkyl of from 1 to 5 carbon atoms, inclusive, ##STR94## orthointerphenylene, and substituted orthointerphenylene, with the provisos that other than when R 14 and R 15 form a ring with the nitrogen atom, one of R 14 and R 15 must always be hydrogen; R' 13 must be a group that can be selectively removed in the presence of NR 14 R 15 ; and when R in the formula II" is other than hydrogen the deprotected compound must be esterified.
Claim 2
Dependent Claim
380 words
A process for preparing racemic mixtures and optically active isomers of compounds having the formula ##STR88## which comprises the deprotection of racemic mixtures and optically active isomers of compounds having the formula ##STR89## wherein R is selected from the group consisting of hydrogen, alkyl of from 1 to 12 carbon atoms, inclusive, halogenated alkyl of from 1 to 5 carbon atoms, inclusive, and 1 to 3 halogen atoms, inclusive, aryl of from 6 to 20 carbon atoms, inclusive, aralkyl of from 7 to 20 carbon atoms, inclusive, and substituted aralkyl of from 7 to 20 carbon atoms inclusive; R' 13 is selected from the group ##STR90## wherein R' 6 is alkyl of from 1 to 8 carbon atoms, inclusive, halogenated alkyl of from 1 to 5 carbon atoms, inclusive, and 1 to 3 halogen atoms, and aralkyl of from 7 to 20 carbon atoms, inclusive, R 14 and R 15 are selected from the group consisting of hydrogen, ##STR91## or when taken together with the nitrogen form the group ##STR92## wherein R 6 is alkyl of from 1 to 8 carbon atoms, inclusive, halogenated alkyl of from 1 to 5 carbon atoms, inclusive, and 1 to 3 halogen atoms, inclusive, aralkyl of from 7 to 20 carbon atoms, inclusive, and substituted aralkyl of from 7 to 20 carbon atoms, inclusive, R 7 is selected from the group consisting of alkyl of from 1 to 12 carbon atoms, inclusive, aryl of from 6 to 20 carbon atoms, inclusive, aralkyl of from 7 to 20 carbon atoms, inclusive, and substituted aralkyl of from 7 to 20 carbon atoms, inclusive, and R 8 is selected from the group consisting of ##STR93## Where R 9 , R 10 , R 11 and R 12 are selected from the group consisting of hydrogen and alkyl of from 1 to 5 carbon atoms, inclusive, ##STR94## orthointerphenylene, and substituted orthointerphenylene, with the provisos that other than when R 14 and R 15 form a ring with the nitrogen atom, one of R 14 and R 15 must always be hydrogen; R' 13 must be a group that can be selectively removed in the presence of NR 14 R 15 ; and when R in the formula II" is other than hydrogen the deprotected compound must be esterified.
Claim 3
Dependent Claim
27 words
A process according to claim 1 wherein R' 13 is phenylalkoxycarbonyl and NR 14 R 15 is phthalimido so that the compound prepared is (αS,5S)-3-oxo-2-phthalimido-5-isoxazolidine acetic acid.
References Cited (Backward Citations)
No citation records indexed.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-06-19 | 1987-12-19 | 1988-06-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-06-19 | 1991-12-19 | 1992-06-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-06-19 | 1995-12-19 | 1996-06-19 | $7700.00 | Window Closed / Lapsed |