WO2001068645A3 - N-cyanomethylcarboxamides and their use as protease inhibitors - Google Patents

N-cyanomethylcarboxamides and their use as protease inhibitors Download PDF

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Publication number
WO2001068645A3
WO2001068645A3 PCT/US2001/008332 US0108332W WO0168645A3 WO 2001068645 A3 WO2001068645 A3 WO 2001068645A3 US 0108332 W US0108332 W US 0108332W WO 0168645 A3 WO0168645 A3 WO 0168645A3
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WO
WIPO (PCT)
Prior art keywords
protease inhibitors
cyanomethylcarboxamides
oxides
novel
pharmaceutically acceptable
Prior art date
Application number
PCT/US2001/008332
Other languages
French (fr)
Other versions
WO2001068645A2 (en
Inventor
James T Palmer
Eduardo L Setti
Zong-Qiang Tian
Shankar Venkatraman
Dan-Xiong Wang
Original Assignee
Axys Pharm Inc
James T Palmer
Eduardo L Setti
Tian Zong Qiang
Shankar Venkatraman
Wang Dan Xiong
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
Application filed by Axys Pharm Inc, James T Palmer, Eduardo L Setti, Tian Zong Qiang, Shankar Venkatraman, Wang Dan Xiong filed Critical Axys Pharm Inc
Priority to AU2001245764A priority Critical patent/AU2001245764A1/en
Publication of WO2001068645A2 publication Critical patent/WO2001068645A2/en
Publication of WO2001068645A3 publication Critical patent/WO2001068645A3/en

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    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D207/14—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
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    • 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
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    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
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    • 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
    • C07D277/22—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • 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
    • C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
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    • 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
    • C07D417/04—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 directly linked by a ring-member-to-ring-member bond
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    • C07—ORGANIC CHEMISTRY
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    • C07D417/06—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 carbon chain containing only aliphatic carbon atoms
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    • 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

The present invention relates to novel N-cyanomethyl amides which are cysteine protease inhibitors, the pharmaceutically acceptable salts and N-oxides thereof, their uses as therapeutic agents and the methods of their making.
PCT/US2001/008332 2000-03-15 2001-03-14 N-cyanomethylcarboxamides and their use as protease inhibitors WO2001068645A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001245764A AU2001245764A1 (en) 2000-03-15 2001-03-14 Novel compounds and compositions as protease inhibitors

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US18969400P 2000-03-15 2000-03-15
US60/189,694 2000-03-15

Publications (2)

Publication Number Publication Date
WO2001068645A2 WO2001068645A2 (en) 2001-09-20
WO2001068645A3 true WO2001068645A3 (en) 2002-03-07

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AU (1) AU2001245764A1 (en)
WO (1) WO2001068645A2 (en)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2002221080A1 (en) 2000-12-08 2002-06-18 Masami Kusaka Substituted thiazole derivatives bearing 3-pyridyl groups, process for preparingthe same and use thereof
AU2002254099B2 (en) 2001-03-02 2006-07-06 Axys Pharmaceuticals, Inc. Cathepsin cysteine protease inhibitors
WO2003039534A1 (en) * 2001-11-08 2003-05-15 Merck & Co., Inc. Compositions and methods for treating osteoporosis
RU2278659C9 (en) 2002-02-01 2007-02-20 Пфайзер Продактс Инк. Method of getting homogenous, hard amorhous dispersions of medicinal preparation dried by dispersion while using modified dispersion-drying modified plant
US7101880B2 (en) 2002-06-24 2006-09-05 Schering Aktiengesellschaft Peptidic compounds as cysteine protease inhibitors
SE0203712D0 (en) 2002-12-13 2002-12-13 Astrazeneca Ab Novel compounds
JP4553899B2 (en) * 2003-08-21 2010-09-29 メルク フロスト カナダ リミテツド Cathepsin cysteine protease inhibitor
ES2534222T3 (en) * 2003-09-18 2015-04-20 Virobay, Inc. Compounds containing haloalkyl as cysteine protease inhibitors
EP1819667B1 (en) 2004-12-02 2012-10-17 ViroBay, Inc. Sulfonamide compounds as cysteine protease inhibitors
PT1865940E (en) 2005-03-21 2013-04-08 Virobay Inc Alpha ketoamide compounds as cysteine protease inhibitors
MX2007011739A (en) 2005-03-22 2008-03-14 Celera Genomics Sulfonyl containing compounds as cysteine protease inhibitors.
US7893112B2 (en) 2006-10-04 2011-02-22 Virobay, Inc. Di-fluoro containing compounds as cysteine protease inhibitors
CA2664878A1 (en) 2006-10-04 2008-04-10 Virobay, Inc. Di-fluoro containing compounds as cysteine protease inhibitors
RU2485114C2 (en) * 2006-12-29 2013-06-20 Эбботт Гмбх Унд Ко.Кг Carboxamide compounds and use thereof as calpain inhibitors
WO2009001129A1 (en) 2007-06-26 2008-12-31 Astrazeneca Ab 1-cyanocyclopropyl-derivatives as cathepsin k inhibitors
TWI453019B (en) * 2007-12-28 2014-09-21 Abbvie Deutschland Carboxamide compounds
EP2240491B1 (en) 2008-01-09 2015-07-15 Amura Therapeutics Limited TETRAHYDROFURO(2,3-b)PYRROL-3-ONE DERIVATIVES AS INHIBITORS OF CYSTEINE PROTEINASES
US8324417B2 (en) 2009-08-19 2012-12-04 Virobay, Inc. Process for the preparation of (S)-2-amino-5-cyclopropyl-4,4-difluoropentanoic acid and alkyl esters and acid salts thereof
CN106928113B (en) * 2015-12-29 2020-07-07 广东东阳光药业有限公司 Cathepsin K inhibitors and uses thereof

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999024460A2 (en) * 1997-11-05 1999-05-20 Novartis Ag Dipeptide nitriles
WO2000055125A2 (en) * 1999-03-15 2000-09-21 Axys Pharmaceuticals, Inc. N-cyanomethyl amides as protease inhibitors

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999024460A2 (en) * 1997-11-05 1999-05-20 Novartis Ag Dipeptide nitriles
WO2000055125A2 (en) * 1999-03-15 2000-09-21 Axys Pharmaceuticals, Inc. N-cyanomethyl amides as protease inhibitors
WO2000055126A2 (en) * 1999-03-15 2000-09-21 Axys Pharmaceuticals, Inc. N-cyanomethylamides as protease inhibitors

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WO2001068645A2 (en) 2001-09-20
AU2001245764A1 (en) 2001-09-24

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