EP0337549A1
Expired / Lapsed
EP
⏱️ 0.0 years remaining
New substituted azetidinones as anti-inflammatory and antidegenerative agents
Assignee: Merck and Co Inc
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Filing: 1989-04-06
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Granted: —
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Expires: 2009-04-06
Abstract
Abstract New substituted azetidinones are found to be potent elastase inhibitors and thereby useful anti- inflammatory/antidegenerative agents.
Inventors
- 👤 Shrenik K. Shah
- 👤 Paul E. Finke
- 👤 James B. Doherty
- 👤 Peter L. Barker
- 👤 William Hagmann
- 👤 Conrad P. Dorn
- 👤 Raymond A. Firestone
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-03 22:36
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; A; A61; A61P; A61P29/00; A61P43/00; C07D205/00; C07D205/02; C07D205/06; C07D205/08; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08; C07D401/00; C07D401/02; C07D401/08; C07D401/12; C07D403/00; C07D403/02; C07D403/12; C07D405/00; C07D405/02; C07D405/12; C07D409/00; C07D409/02; C07D409/12
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
303 words
A process for the preparation of a compound of the formula (A) wherein: R and R 1 independently are C 1 - 6 alkyl or C 1 -6 alkoxy C 1 -s alkyl; M is (1) hydrogen, (2) C 1 -s alkyl, (3) C 2 - 6 alkenyl, or (4) C 1 -s alkoxy-C 1-6 alkyl; X 5 is (1) hydrogen, (2) C, - 6 alkyl, (3) halo C, - 6 alkyl, (4) C 2-6 alkenyl, (5) C 2-6 alkynyl, (6) carboxy, (7) carboxy-C, - 6 alkyl, (8) carboxy-C 1-6 alkylcarbonyl, (9) carboxy-C 1-6 alkylcarbonylamino, (10) carboxy-C 2 - 6 alkenyl, (11) hydroxy-C 1-6 alkyl, (12) C 1-6 alkylcarbonyl, (13) C 1-6 alkylcarbonylamino, or (14) di-(C 1-6 alkyl)amino-C 1-6 alkyl; and X 6 is (1) hydrogen, (2) C 1 - 6 alkyl, (3) halo (4) carboxy, (5) C 1 - 6 alkoxy, (6) phenyl, (7) C 1 - 6 alkylcarbonyl, (8) di-(C 1-6 alkyl)amino, (9) phenoxy, (10) methylenedioxy, (11) 2,3-furanyl, or (12) 2,3-thienyl; or a pharmaceutically acceptable salt thereof which comprises (1) reacting a compound of the following formula (B) with a compound of the formula (C) wherein X 5 ' is (1) hydrogen (2) C 1-6 alkyl, (3) halo-C, -6 alkyl, (4) C 2 - 6 alkenyl, (5) C 2-6 alkynyl, (6) C 1-6 alkoxycarbonyl, (7) C 1 -6 alkoxycarbonyl-C 1-6 alkyl, (8) C 1 -6 alkoxycarbonyl-C 1-6 alkylcarbonyl, (9) C 1 -6 alkoxycarbonyl-C 1-6 alkylcarbonylamino, (10) C 1-6 alkoxycarbonyl-C 2-6 alkenyl, (11) hydroxyalkyl, (12) C 1-6 alkylcarbonyl, (13) C 1-6 alkylcarbonylamino, or (14) di-(C 1-6 alkyl)amino-C 1-6 alkyl under basic conditions to afford a compound of the formula (D) and (2) reacting compound (D) with a compound of the formula (E) under basic conditions, and optionally converting X s into X s , to yield the compound of the formula (A)
Claim 2
Dependent Claim
303 words
A process for the preparation of a compound of the formula (A) wherein: R and R 1 independently are C 1 - 6 alkyl or C 1 -6 alkoxy C 1 -s alkyl; M is (1) hydrogen, (2) C 1 -s alkyl, (3) C 2 - 6 alkenyl, or (4) C 1 -s alkoxy-C 1-6 alkyl; X 5 is (1) hydrogen, (2) C, - 6 alkyl, (3) halo C, - 6 alkyl, (4) C 2-6 alkenyl, (5) C 2-6 alkynyl, (6) carboxy, (7) carboxy-C, - 6 alkyl, (8) carboxy-C 1-6 alkylcarbonyl, (9) carboxy-C 1-6 alkylcarbonylamino, (10) carboxy-C 2 - 6 alkenyl, (11) hydroxy-C 1-6 alkyl, (12) C 1-6 alkylcarbonyl, (13) C 1-6 alkylcarbonylamino, or (14) di-(C 1-6 alkyl)amino-C 1-6 alkyl; and X 6 is (1) hydrogen, (2) C 1 - 6 alkyl, (3) halo (4) carboxy, (5) C 1 - 6 alkoxy, (6) phenyl, (7) C 1 - 6 alkylcarbonyl, (8) di-(C 1-6 alkyl)amino, (9) phenoxy, (10) methylenedioxy, (11) 2,3-furanyl, or (12) 2,3-thienyl; or a pharmaceutically acceptable salt thereof which comprises (1) reacting a compound of the following formula (B) with a compound of the formula (C) wherein X 5 ' is (1) hydrogen (2) C 1-6 alkyl, (3) halo-C, -6 alkyl, (4) C 2 - 6 alkenyl, (5) C 2-6 alkynyl, (6) C 1-6 alkoxycarbonyl, (7) C 1 -6 alkoxycarbonyl-C 1-6 alkyl, (8) C 1 -6 alkoxycarbonyl-C 1-6 alkylcarbonyl, (9) C 1 -6 alkoxycarbonyl-C 1-6 alkylcarbonylamino, (10) C 1-6 alkoxycarbonyl-C 2-6 alkenyl, (11) hydroxyalkyl, (12) C 1-6 alkylcarbonyl, (13) C 1-6 alkylcarbonylamino, or (14) di-(C 1-6 alkyl)amino-C 1-6 alkyl under basic conditions to afford a compound of the formula (D) and (2) reacting compound (D) with a compound of the formula (E) under basic conditions, and optionally converting X s into X s , to yield the compound of the formula (A)
Claim 3
Dependent Claim
27 words
A process of Claim 1 wherein: R and R 1 independently are C 1-6 alkyl; and X 5 is carboxy or carboxy C 1 - 6 alkyl.
Claim 4
Dependent Claim
26 words
A process of Claim 2 wherein: M is C 1-3 alkyl or allyl; and X 6 is hydrogen, C, - 6 alkyl, or 3,4-methylenedioxy or phenyl.
Claim 5
Dependent Claim
16 words
A process of Claim 3 wherein: R is ethyl; and R 1 is methyl or ethyl.
Claim 6
Dependent Claim
24 words
A process of Claim 4 wherein: R and R 1 are ethyl; M is n-propyl; X 5 is 4-carboxymethyl; and X 6 is 4-methyl.
Claim 7
Dependent Claim
46 words
A process of Claim 1 wherein: Step (1) is in the presence of an alkali metal hydroxide; Step (2) is in the presence of a tri(Ci - 6 alkyl)amine; and the conversion of Xs into X s is accomplished in the presence of a strong acid.
References Cited (Backward Citations)
EP0199630A1
Cited
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