US4918105A
Expired / Lapsed
US
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Novel compounds with collagenase-inhibiting activity, a process for their preparation and pharmaceutical compositions in which these compounds are present
Assignee: Laboratoire Roger Bellon SA
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Filing: 1988-01-05
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Granted: 1990-04-17
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Expires: 2008-01-05
Abstract
Abstract The present invention relates to a novel family of chemical compounds possessing a pharmacological activity, in particular a collagenase-inhibiting activity, a process for the production of these compounds and pharmaceutical compositions in which they are present. According to the invention, these compounds correspond to the general formula: ##STR1## in which: W represents an amino acid residue selected from the group comprising valine, lysine, norleucine and methionine, and Z represents an amino radical or an alkylamino radical of which the alkyl part, which contains 1 or 2 carbon atoms, is substituted by a phenyl or trifluorophenyl radical, and also include their diastereoisomers and their addition salts with pharmaceutically acceptable acids. The invention is applicable especially in the pharmaceutical industry.
Inventors
- 👤 Terence Cartwright
- 👤 Romaine Bouboutou-Tello
- 👤 Yves Lelievre
- 👤 Marie-Claude Fournier-Zaluski
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-10 02:36
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/16; A61P; A61P1/00; A61P1/02; A61P17/00; A61P27/00; A61P27/02; A61P29/00; A61P43/00; C; C07; C07C; C07C237/00
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
71 words
Compounds with collagenase-inhibiting activity, corresponding to the general formula: ##STR67## in which: W represents an amino acid residue selected from the group consisting of valine, lysine, norleucine and methionine, and Z represents an amino radical or an alkylamino radical of which the alkyl part, which contains 1 or 2 carbon atoms, is substituted by a phenyl or trifluorophenyl radical, and also their diastereoisomers and their addition salts with pharmaceutically acceptable acids.
Claim 2
Dependent Claim
71 words
Compounds with collagenase-inhibiting activity, corresponding to the general formula: ##STR67## in which: W represents an amino acid residue selected from the group consisting of valine, lysine, norleucine and methionine, and Z represents an amino radical or an alkylamino radical of which the alkyl part, which contains 1 or 2 carbon atoms, is substituted by a phenyl or trifluorophenyl radical, and also their diastereoisomers and their addition salts with pharmaceutically acceptable acids.
Claim 3
Dependent Claim
18 words
Compounds as claimed in claim 1 which correspond to formula I in which W represents an L-valyl group.
Claim 4
Dependent Claim
21 words
Compounds as claimed in claim 1, selected from the group comprising the following: Nα-(N-hydroxy-2-isobutylsuccinamoyl)-L-valinamide, N-benzyl-Nα-(N-hydroxy-2-isobutylsuccinamoyl)-L-valinamide N-(4-trifluoromethylbenzyl)-Nα-(N-hydroxy-2-isobutylsuccinamoyl)-L-valinamide N-phenethyl-Nα-(N-hydroxy-2-isobutylsuccinamoyl)-L-valinamide N-benzyl-Nα-(N-hydroxy-2-isobutylsuccinamoyl)-L-norleucine and N-benzyl-Nα-(N-hydroxy-2-isobutylsuccinamoyl)-L-lysinamide N-benzyl-Nα-(N-hydroxy-2-isobutylsuccinamoyl)-L-methioninamide.
Claim 5
Dependent Claim
32 words
A pharmaceutical composition which contains at least a compound as claimed in one of claims 1 or 3 as the active ingredient, in association with a pharmaceutically acceptable, non-toxic vehicle or excipient.
Claim 6
Dependent Claim
35 words
A pharmaceutical composition with collagenase-inhibiting activity, which contains at least a compound as claimed in one of claims 1 or 3 as the active ingredient, in association with a pharmaceutically acceptable, non-toxic vehicle or excipient.
Claim 7
Dependent Claim
32 words
A pharmaceutical composition according to claim 5, wherein the active ingredient is in the form of the most active isomer, as determined after separation of the distinct isomeric forms of the compound.
Claim 8
Dependent Claim
83 words
A pharmaceutical composition with collagenase inhibiting activity, which contains at least one compound as claimed in claim 2, as the active ingredient, in association with a pharmaceutically acceptable, non-toxic vehicle or excipient, wherein the active ingredient is in the form of the most active isomer, as determined after separation of the distinct isomeric forms of the compound, said active isomer being characterized in NMR by the chemical shift situated at or below 2 ppm and corresponding to the >CH.sub.β -- of the valine.
Claim 9
Dependent Claim
25 words
Method of treatment of diseases which involve excessive destruction of collagen by collagenase, wherein said method comprises administering a pharmaceutical composition according to claim 5.
Claim 10
Dependent Claim
25 words
Method of treatment of diseases which involve excessive destruction of collagen by collagenase, wherein said method comprises administering a pharmaceutical composition according to claim 6.
Claim 11
Dependent Claim
31 words
Compounds as claimed in claim 1, wherein Z represents an alkylamino radical of which the alkyl part, which contains 1 or 2 carbons, is substituted by a phenyl or trifluorophenyl radical.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-04-16 | 1993-10-16 | 1994-04-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-04-16 | 1997-10-16 | 1998-04-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-04-16 | 2001-10-16 | 2002-04-17 | $7700.00 | Window Closed / Lapsed |