CA2193178A1 - Matrix metalloprotease inhibitors - Google Patents
Matrix metalloprotease inhibitorsInfo
- Publication number
- CA2193178A1 CA2193178A1 CA002193178A CA2193178A CA2193178A1 CA 2193178 A1 CA2193178 A1 CA 2193178A1 CA 002193178 A CA002193178 A CA 002193178A CA 2193178 A CA2193178 A CA 2193178A CA 2193178 A1 CA2193178 A1 CA 2193178A1
- Authority
- CA
- Canada
- Prior art keywords
- cycloalkyl
- lower alkyl
- cycloalkylalkyl
- hydrogen
- heteroaralkyl
- Prior art date
- 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.)
- Granted
Links
Abstract
Compounds of the formula:
(see fig. I) I
wherein:
n is 0, 1 or 2;
Y is hydroxy or XONH-, where X is hydrogen or lower alkyl;
R1 is hydrogen or lower alkyl;
R2 is hydrogen, lower alkyl, heteroalkyl, aryl, aralkyl, arylheteroalkyl, cycloalkyl, cycloalkylalkyl, heteroaryl, heteroaralkyl, heteroarylheteroalkyl, heterocyclo, heterocylo-lower alkyl, heterocyclo-lower heteroalkyl or -NR6R7, wherein:
R6 is hydrogen, lower alkyl, cycloalkyl or cycloalkylalkyl, aryl, heteroaryl and heteroaralkyl;
R7 is hydrogen, lower alkyl, cycloalkyl or cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, -C(O)R8, -C(O)NR8R9, -SO2NR8R9, -SO2R10, aryloxycarbonyl, or alkoxycarbonyl; or R6 and R7 together with the nitrogen atom to which they are attached represent a heterocyclo group;
wherein R8 and R9 are independently hydrogen, lower alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl or heteroalkyl; and R10 is lower alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, heteroalkyl or heterocyclo; or R1 and R2 together with the carbon atom to which they are attached represent a cycloalkyl or heterocyclo group;
R3 is hydrogen, lower alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, heteroalkyl or lower alkoxy;
R4 is hydrogen, lower alkyl, cycloalkyl or cycloalkylalkyl; or R2 and R3 together with the carbons to which they are attached represent a cycloalkyl or heterocyclo group; or R3 and R4 together with the carbon to which they are attached represent a cycloalkyl or heterocyclo group; and R5 is lower alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, or heteroaralkyl;
or pharmaceutically acceptable salts or esters thereof exhibit useful pharmacological properties, in particular for use as matrix metalloprotease inhibitors, particularly for interstitial collagenases.
(see fig. I) I
wherein:
n is 0, 1 or 2;
Y is hydroxy or XONH-, where X is hydrogen or lower alkyl;
R1 is hydrogen or lower alkyl;
R2 is hydrogen, lower alkyl, heteroalkyl, aryl, aralkyl, arylheteroalkyl, cycloalkyl, cycloalkylalkyl, heteroaryl, heteroaralkyl, heteroarylheteroalkyl, heterocyclo, heterocylo-lower alkyl, heterocyclo-lower heteroalkyl or -NR6R7, wherein:
R6 is hydrogen, lower alkyl, cycloalkyl or cycloalkylalkyl, aryl, heteroaryl and heteroaralkyl;
R7 is hydrogen, lower alkyl, cycloalkyl or cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, -C(O)R8, -C(O)NR8R9, -SO2NR8R9, -SO2R10, aryloxycarbonyl, or alkoxycarbonyl; or R6 and R7 together with the nitrogen atom to which they are attached represent a heterocyclo group;
wherein R8 and R9 are independently hydrogen, lower alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl or heteroalkyl; and R10 is lower alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, heteroalkyl or heterocyclo; or R1 and R2 together with the carbon atom to which they are attached represent a cycloalkyl or heterocyclo group;
R3 is hydrogen, lower alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, heteroalkyl or lower alkoxy;
R4 is hydrogen, lower alkyl, cycloalkyl or cycloalkylalkyl; or R2 and R3 together with the carbons to which they are attached represent a cycloalkyl or heterocyclo group; or R3 and R4 together with the carbon to which they are attached represent a cycloalkyl or heterocyclo group; and R5 is lower alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl, heteroaryl, or heteroaralkyl;
or pharmaceutically acceptable salts or esters thereof exhibit useful pharmacological properties, in particular for use as matrix metalloprotease inhibitors, particularly for interstitial collagenases.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US893995P | 1995-12-20 | 1995-12-20 | |
| US60/008,939 | 1995-12-20 | ||
| US2243996P | 1996-08-07 | 1996-08-07 | |
| US60/022,439 | 1996-08-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2193178A1 true CA2193178A1 (en) | 1997-06-21 |
| CA2193178C CA2193178C (en) | 2001-11-06 |
Family
ID=26678819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2193178 Expired - Fee Related CA2193178C (en) | 1995-12-20 | 1996-12-17 | Matrix metalloprotease inhibitors |
Country Status (2)
| Country | Link |
|---|---|
| CA (1) | CA2193178C (en) |
| TW (1) | TW580491B (en) |
-
1996
- 1996-12-17 CA CA 2193178 patent/CA2193178C/en not_active Expired - Fee Related
-
1997
- 1997-03-05 TW TW86102686A patent/TW580491B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2193178C (en) | 2001-11-06 |
| TW580491B (en) | 2004-03-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20131217 |