CA2580065A1 - Processes and intermediates for preparing cysteine protease inhibitors - Google Patents

Processes and intermediates for preparing cysteine protease inhibitors Download PDF

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Publication number
CA2580065A1
CA2580065A1 CA002580065A CA2580065A CA2580065A1 CA 2580065 A1 CA2580065 A1 CA 2580065A1 CA 002580065 A CA002580065 A CA 002580065A CA 2580065 A CA2580065 A CA 2580065A CA 2580065 A1 CA2580065 A1 CA 2580065A1
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CA
Canada
Prior art keywords
compound
formula
group
hydrogen
alkyl
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.)
Abandoned
Application number
CA002580065A
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English (en)
French (fr)
Inventor
Jiayao Li
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.)
Virobay Inc
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2580065A1 publication Critical patent/CA2580065A1/en
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
    • C07C321/16—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen 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
    • C07D213/04—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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32—Sulfur 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
    • C07D213/04—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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/32—Sulfur atoms
    • C07D213/34—Sulfur atoms to which a second hetero atom is attached
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings 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
    • C07D309/14—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Pyridine Compounds (AREA)
  • Pyrane Compounds (AREA)
CA002580065A 2004-09-17 2005-09-16 Processes and intermediates for preparing cysteine protease inhibitors Abandoned CA2580065A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US61080604P 2004-09-17 2004-09-17
US60/610,806 2004-09-17
PCT/US2005/033051 WO2006034004A2 (en) 2004-09-17 2005-09-16 Processes and intermediates for preparing cysteine protease inhibitors

Publications (1)

Publication Number Publication Date
CA2580065A1 true CA2580065A1 (en) 2006-03-30

Family

ID=35899659

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002580065A Abandoned CA2580065A1 (en) 2004-09-17 2005-09-16 Processes and intermediates for preparing cysteine protease inhibitors

Country Status (15)

Country Link
US (1) US7737300B2 (OSRAM)
EP (1) EP1799645A2 (OSRAM)
JP (1) JP2008513472A (OSRAM)
KR (1) KR20070061877A (OSRAM)
CN (1) CN101068783A (OSRAM)
AU (1) AU2005287046A1 (OSRAM)
BR (1) BRPI0515470A (OSRAM)
CA (1) CA2580065A1 (OSRAM)
CR (1) CR8993A (OSRAM)
EC (1) ECSP077321A (OSRAM)
IL (1) IL181792A0 (OSRAM)
MX (1) MX2007003118A (OSRAM)
NO (1) NO20071937L (OSRAM)
WO (1) WO2006034004A2 (OSRAM)
ZA (1) ZA200703102B (OSRAM)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4991295B2 (ja) 2003-09-18 2012-08-01 ビロベイ，インコーポレイティド システイン・プロテアーゼ阻害剤としてのハロアルキルを含む化合物
JP5154944B2 (ja) 2004-12-02 2013-02-27 ビロベイ，インコーポレイティド システインプロテアーゼインヒビターとしてのスルホンアミド含有化合物
NZ561681A (en) 2005-03-21 2011-01-28 Virobay Inc Alpha ketoamide compounds as cysteine protease inhibitors
US7893093B2 (en) 2005-03-22 2011-02-22 Virobay, Inc. Sulfonyl containing compounds as cysteine protease inhibitors
WO2008028301A1 (en) * 2006-09-08 2008-03-13 Merck Frosst Canada Ltd. Prodrugs of inhibitors of cathepsin s
US20100048717A1 (en) * 2006-09-25 2010-02-25 MERCK FROSST CANADA LTD, Merk & Co., Inc. Cathepsin b inhibitors
US7893112B2 (en) 2006-10-04 2011-02-22 Virobay, Inc. Di-fluoro containing compounds as cysteine protease inhibitors
EP2079683B1 (en) 2006-10-04 2015-01-21 Virobay, Inc. Di-fluoro containing compounds as cysteine protease inhibitors
CA2672494A1 (en) 2006-12-14 2008-06-19 Nps Pharmaceuticals, Inc. Use of d-serine derivatives for the treatment of anxiety disorders
JP5364695B2 (ja) * 2007-04-02 2013-12-11 メルク カナダ インコーポレイテッド カテプシンｋインヒビターのアミド化調製方法
CN103664973B (zh) 2008-10-17 2017-04-19 泽农医药公司 螺羟吲哚化合物及其作为治疗剂的用途
WO2010148488A1 (en) * 2009-06-22 2010-12-29 Merck Frosst Canada Ltd. Cathepsin cysteine protease inhibitors for the treatment of various diseases
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
WO2012119941A1 (en) 2011-03-04 2012-09-13 Prozymex A/S Peptidyl nitrilcompounds as peptidase inhibitors
US20120329837A1 (en) * 2011-06-17 2012-12-27 Virobay, Inc. Cathepsin inhibitors for treating microglia-mediated neuron loss in the central nervous system
CN106478564B (zh) * 2015-08-29 2021-11-12 广东东阳光药业有限公司 组织蛋白酶k抑制剂及其用途
CN107922315B (zh) * 2015-08-29 2021-03-26 广东东阳光药业有限公司 组织蛋白酶k抑制剂及其用途
EP3946332A1 (en) 2019-04-05 2022-02-09 Université de Bretagne Occidentale Protease-activated receptor-2 inhibitors for the treatment of sensory neuropathy induced by a marine neurotoxic poisoning

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1273444C (zh) * 1997-11-05 2006-09-06 诺瓦提斯公司 二肽腈
GB9723407D0 (en) * 1997-11-05 1998-01-07 Ciba Geigy Ag Organic compounds
JP2002537293A (ja) * 1999-02-20 2002-11-05 アストラゼネカ アクチボラグ カテプシンｌおよび／またはカテプシンｓの阻害剤としてのアセタミドアセトニトリル誘導体
WO2003029200A2 (en) * 2001-10-02 2003-04-10 Boehringer Ingelheim Pharmaceuticals, Inc. Compounds useful as reversible inhibitors of cysteine proteases
ATE395911T1 (de) * 2002-03-05 2008-06-15 Merck Frosst Canada Ltd Cathepsin-cystein-protease-hemmer
WO2003075863A1 (en) * 2002-03-11 2003-09-18 Kanebo Cosmetics Inc. Cosmetics

Also Published As

Publication number Publication date
US7737300B2 (en) 2010-06-15
KR20070061877A (ko) 2007-06-14
CN101068783A (zh) 2007-11-07
ZA200703102B (en) 2009-09-30
CR8993A (es) 2007-10-04
US20080114175A1 (en) 2008-05-15
EP1799645A2 (en) 2007-06-27
ECSP077321A (es) 2007-04-26
WO2006034004A2 (en) 2006-03-30
JP2008513472A (ja) 2008-05-01
BRPI0515470A (pt) 2008-07-22
AU2005287046A1 (en) 2006-03-30
WO2006034004A3 (en) 2006-11-23
IL181792A0 (en) 2007-07-04
NO20071937L (no) 2007-06-15
MX2007003118A (es) 2007-05-24

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Legal Events

Date Code Title Description
FZDE Discontinued