GB2299334A - Metalloproteinase inhibitors - Google Patents

Metalloproteinase inhibitors

Info

Publication number
GB2299334A
GB2299334A GB9611280A GB9611280A GB2299334A GB 2299334 A GB2299334 A GB 2299334A GB 9611280 A GB9611280 A GB 9611280A GB 9611280 A GB9611280 A GB 9611280A GB 2299334 A GB2299334 A GB 2299334A
Authority
GB
United Kingdom
Prior art keywords
ring
metalloproteinase inhibitors
oxidised
phenyl
rings
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
Application number
GB9611280A
Other versions
GB9611280D0 (en
GB2299334B (en
Inventor
Raymond Paul Beckett
Mark Whittaker
Andrew Miller
Fionna Mitchell Martin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Vernalis R&D Ltd
Original Assignee
British Biotech Pharmaceuticals Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from GB9401034A external-priority patent/GB9401034D0/en
Priority claimed from GB9415619A external-priority patent/GB9415619D0/en
Application filed by British Biotech Pharmaceuticals Ltd filed Critical British Biotech Pharmaceuticals Ltd
Priority to GB9611280A priority Critical patent/GB2299334B/en
Priority to GB9722619A priority patent/GB2316078B/en
Priority claimed from PCT/GB1995/000111 external-priority patent/WO1995019956A1/en
Publication of GB9611280D0 publication Critical patent/GB9611280D0/en
Publication of GB2299334A publication Critical patent/GB2299334A/en
Application granted granted Critical
Publication of GB2299334B publication Critical patent/GB2299334B/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Abstract

Matrix metalloproteinase inhibiting compounds of formula (I), wherein X is a -CO 2 H or -CONHOH group; R 4 is a phenyl or 5- or 6-membered heteroaryl ring wherein any ring nitrogen atom may be oxidised as an N-oxide, which may be optionally fused to a benzene ring or to a 5-, 6- or 7-membered heterocyclic ring, and wherein any of the rings may be optionally substituted.
GB9611280A 1994-01-20 1995-01-20 Metalloproteinase inhibitors Expired - Fee Related GB2299334B (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB9611280A GB2299334B (en) 1994-01-20 1995-01-20 Metalloproteinase inhibitors
GB9722619A GB2316078B (en) 1994-01-20 1995-01-20 L-tert-leucine-2-pyridylamide

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB9401034A GB9401034D0 (en) 1994-01-20 1994-01-20 Metalloproteinase inhibitors
GB9415619A GB9415619D0 (en) 1994-08-02 1994-08-02 Metalloprotease inhibitors
GB9611280A GB2299334B (en) 1994-01-20 1995-01-20 Metalloproteinase inhibitors
PCT/GB1995/000111 WO1995019956A1 (en) 1994-01-20 1995-01-20 Metalloproteinase inhibitors

Publications (3)

Publication Number Publication Date
GB9611280D0 GB9611280D0 (en) 1996-07-31
GB2299334A true GB2299334A (en) 1996-10-02
GB2299334B GB2299334B (en) 1998-05-13

Family

ID=27267020

Family Applications (2)

Application Number Title Priority Date Filing Date
GB9722619A Expired - Fee Related GB2316078B (en) 1994-01-20 1995-01-20 L-tert-leucine-2-pyridylamide
GB9611280A Expired - Fee Related GB2299334B (en) 1994-01-20 1995-01-20 Metalloproteinase inhibitors

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB9722619A Expired - Fee Related GB2316078B (en) 1994-01-20 1995-01-20 L-tert-leucine-2-pyridylamide

Country Status (1)

Country Link
GB (2) GB2316078B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2300188B (en) * 1994-01-22 1998-07-01 British Biotech Pharm Metalloproteinase inhibitors

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993020047A1 (en) * 1992-04-07 1993-10-14 British Bio-Technology Limited Hydroxamic acid based collagenase and cytokine inhibitors
WO1994024140A1 (en) * 1993-04-17 1994-10-27 British Bio-Technology Limited Hydroxamic acid derivatives

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993020047A1 (en) * 1992-04-07 1993-10-14 British Bio-Technology Limited Hydroxamic acid based collagenase and cytokine inhibitors
WO1994024140A1 (en) * 1993-04-17 1994-10-27 British Bio-Technology Limited Hydroxamic acid derivatives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
STN-INFORMATION SERVICE FILE:REG;RN=56266-03-6 & J. CHEM. SOC., PERKIN TRANS. 1 (1975), (9), 857-860 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2300188B (en) * 1994-01-22 1998-07-01 British Biotech Pharm Metalloproteinase inhibitors

Also Published As

Publication number Publication date
GB9722619D0 (en) 1997-12-24
GB9611280D0 (en) 1996-07-31
GB2316078A (en) 1998-02-18
GB2316078B (en) 1998-06-03
GB2299334B (en) 1998-05-13

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Legal Events

Date Code Title Description
PCNP Patent ceased through non-payment of renewal fee

Effective date: 20070120