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Last Updated: April 2, 2020

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Claims for Patent: 4,599,361

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Summary for Patent: 4,599,361
Title: Hydroxamic acid based collagenase inhibitors
Abstract:This disclosure relates to a novel class of hydroxamic acid based collagenase inhibitor derivatives. The disclosure further relates to pharmaceutical compositions containing such compounds and to the use of such compounds and compositions in the treatment of collagenase induced diseases.
Inventor(s): Dickens; Jonathan P. (High Wycombe, GB2), Donald; David K. (High Wycombe, GB2), Kneen; Geoffrey (West Wycombe, GB2), McKay; William R. (High Wycombe, GB2)
Assignee: G. D. Searle & Co. (Skokie, IL)
Application Number:06/774,491
Patent Claims:1. A compound of the formula ##STR26## wherein R.sup.1 is C.sub.1 -C.sub.6 alkyl;

R.sup.2 is C.sub.1 -C.sub.6 alkyl, benzyl, benzyloxybenzyl, (C.sub.1 -C.sub.6 alkoxy)benzyl or benzyloxy(C.sub.1 -C.sub.6 alkyl);

a is a chiral center with optional R or S stereochemistry;

A is a ##STR27## group or a --(CR.sup.3 .dbd.CR.sup.4)-- group wherein b and c are chiral centers with optional R or S stereochemistry; R.sup.3 is hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl or phenyl(C.sub.1 -C.sub.6 alkyl) and R.sup.4 is hydrogen or C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.6 alkyl), cycloalkyl or cycloalkyl(C.sub.1 -C.sub.6 alkyl).

2. A compound according to claim 1

wherein chiral center a has S stereochemistry.

3. A compound according to claim 2

wherein A is a ##STR28##

4. A compound according to claim 3 wherein R.sup.2 is (C.sub.1 -C.sub.6 alkoxy)benzyl.

5. A compound according to claim 4

wherein R.sup.2 is 4-methoxybenzyl, R.sup.4 is C.sub.1 -C.sub.4 alkyl and R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or phenyl(C.sub.1 -C.sub.6 alkyl).

6. A compound according to claim 5 wherein R.sup.1 is methyl, R.sup.3 is hydrogen or methyl and R.sup.4 is 2-methylpropyl.

7. A compound according to claim 6 wherein R.sup.3 is hydrogen.

8. A compound according to claim 7 having the following NMR spectrum:

NMR (d.sub.6 -DMSO) 0.7-0.9 (6H, m, {CH.sub.3 }.sub.2 CH); 1.3 (1H, m, {CH.sub.3 }.sub.2 CH); 1.9-2.2 (3H, 2xm, CH.sub.2 CH); 2.50 (3H, m, CHCH.sub.2 CO, +CH.sub.2 CHCO); 2.6 (2H, m, ArCH.sub.2); 2.6 (3H, d, NHCH.sub.3); 3.7 (3H, s, OCH.sub.3); 4.3-4.4 (1H, m, ArCH.sub.3 CH); 6.75-7.1 (4H, 2xd, J=8 Hz, aromatic); 7.9 (1H, m, NHCH.sub.3); 8.05 (1H, d, CONHCH); 8.65 (1H, s, NHOH {D.sub.2 O exchange}); 10.4 (1H, s, NHOH {D.sub.2 O exchange}).

9. A compound according to claim 6 wherein R.sup.3 is methyl.

10. A compound according to claim 9 having the following NMR spectrum:

NMR (d.sub.6 -DMSO) 0.64-0.92 (9H, m, {CH.sub.3 }.sub.2 CHCH.sub.2); 1.30 (3H, m, CH.sub.3 CH); 2.20-2.40 (2H, m, CH.sub.3 CH and CH.sub.3 CHCH); 2.45 (2H, m, ArCH.sub.2); 2.55 (3H, d, J=4 Hz, NHCH.sub.3); 3.68 (3H, s, OCH.sub.3); 4.45 (1H, m, ArCH.sub.2 CH); 6.80 and 7.16 (4H, two d's, J=7 Hz, aromatic); 7.72 (1H, m, NHCH.sub.3); 8.18 (1H, d, J=7 Hz, CONHCH.sub.3); 8.72 (1H, s, NHOH {D.sub.2 O exchange}); 10.37 (1H, s, NHOH {D.sub.2 O exchange}).

11. A method of promoting an antiarthritic effect in a mammal in need thereof comprising administering thereto a collagenase inhibiting effective amount of a compound according to claim 1.

Details for Patent 4,599,361

Applicant Tradename Biologic Ingredient Dosage Form BLA Number Approval Date Patent No. Assignee Estimated Patent Expiration Status Orphan Source
Smith And Nephew SANTYL collagenase OINTMENT;TOPICAL 101995 001 1965-06-04   Start Trial G. D. Searle & Co. (Skokie, IL) 2039-03-29 RX search
>Applicant >Tradename >Biologic Ingredient >Dosage Form >BLA >Number >Approval Date >Patent No. >Assignee >Estimated Patent Expiration >Status >Orphan >Source

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