JP2008513472A - システインプロテアーゼインヒビターの調製のための方法及び中間体 - Google Patents

システインプロテアーゼインヒビターの調製のための方法及び中間体 Download PDF

Info

Publication number
JP2008513472A
JP2008513472A JP2007532479A JP2007532479A JP2008513472A JP 2008513472 A JP2008513472 A JP 2008513472A JP 2007532479 A JP2007532479 A JP 2007532479A JP 2007532479 A JP2007532479 A JP 2007532479A JP 2008513472 A JP2008513472 A JP 2008513472A
Authority
JP
Japan
Prior art keywords
compound
formula
optionally
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.)
Pending
Application number
JP2007532479A
Other languages
English (en)
Japanese (ja)
Other versions
JP2008513472A5 (OSRAM
Inventor
リ，チィアヤオ
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.)
Bayer Pharma AG
Original Assignee
Bayer Schering Pharma AG
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 Bayer Schering Pharma AG filed Critical Bayer Schering Pharma AG
Publication of JP2008513472A publication Critical patent/JP2008513472A/ja
Publication of JP2008513472A5 publication Critical patent/JP2008513472A5/ja
Pending legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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)
JP2007532479A 2004-09-17 2005-09-16 システインプロテアーゼインヒビターの調製のための方法及び中間体 Pending JP2008513472A (ja)

Applications Claiming Priority (2)

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

Publications (2)

Publication Number Publication Date
JP2008513472A true JP2008513472A (ja) 2008-05-01
JP2008513472A5 JP2008513472A5 (OSRAM) 2008-07-03

Family

ID=35899659

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2007532479A Pending JP2008513472A (ja) 2004-09-17 2005-09-16 システインプロテアーゼインヒビターの調製のための方法及び中間体

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)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008534510A (ja) * 2005-03-22 2008-08-28 セレーラ ジェノミックス システインプロテアーゼ阻害剤としてのスルホニル基含有化合物

Families Citing this family (17)

* 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
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

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001522862A (ja) * 1997-11-05 2001-11-20 ノバルティス アクチエンゲゼルシャフト ジペプチドニトリル
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
JP2005526753A (ja) * 2002-03-05 2005-09-08 メルク　フロスト　カナダ　アンド　カンパニー カテプシンシステインプロテアーゼ阻害剤

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9723407D0 (en) * 1997-11-05 1998-01-07 Ciba Geigy Ag Organic compounds
WO2003029200A2 (en) * 2001-10-02 2003-04-10 Boehringer Ingelheim Pharmaceuticals, Inc. Compounds useful as reversible inhibitors of cysteine proteases
WO2003075863A1 (en) * 2002-03-11 2003-09-18 Kanebo Cosmetics Inc. Cosmetics

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001522862A (ja) * 1997-11-05 2001-11-20 ノバルティス アクチエンゲゼルシャフト ジペプチドニトリル
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
JP2005526753A (ja) * 2002-03-05 2005-09-08 メルク　フロスト　カナダ　アンド　カンパニー カテプシンシステインプロテアーゼ阻害剤

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008534510A (ja) * 2005-03-22 2008-08-28 セレーラ ジェノミックス システインプロテアーゼ阻害剤としてのスルホニル基含有化合物

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
CA2580065A1 (en) 2006-03-30
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

Similar Documents

Publication Publication Date Title
JP2008513472A (ja) システインプロテアーゼインヒビターの調製のための方法及び中間体
AU779177B2 (en) Novel compounds and compositions as protease inhibitors
EA011855B1 (ru) Соединения, содержащие галоидалкил, как ингибиторы цистеиновых протеаз
RU2376285C2 (ru) Процесс получения гидрохлорида 2-амино-2-[2-[4-(3-бензилоксифенилтио)-2-хлорфенилэтил]-1,3-пропандиола] и его гидратов, а также промежуточные продукты их получения
JPWO2004026817A1 (ja) アミノアルコール誘導体とその付加塩及び免疫抑制剤
WO1994025432A1 (fr) Derive amide d'amino acide, bactericide horticole, et procede de production
JP2007519744A (ja) システインプロテアーゼインヒビターとしてのシリナン化合物。
JP4988589B2 (ja) システインプロテアーゼインヒビターとしてのハロアルキル含有化合物
PT1865940E (pt) Compostos alfa-cetoamida como inibidores de proteases de cisteína
EP2361243B1 (en) Haloalkyl containing compounds as cysteine protease inhibitors
RU2191181C2 (ru) Производные тиенилциклогексана, способ их получения и промежуточные продукты
JPWO2010061621A1 (ja) ｔｒａｎｓ−｛４−［（アルキルアミノ）メチル］シクロヘキシル｝酢酸エステルの製造方法
JP3726996B2 (ja) サイトキサゾンの合成方法
US5493047A (en) Method of preparing optically active cyanohydrin derivatives
ES2293587T3 (es) Procedimiento de sintesis e intermediarios de benzoxatiepinas.
JPH10287596A (ja) 含フッ素化合物の製法
JPS6257183B2 (OSRAM)
KR0182192B1 (ko) 광학활성형 (3r,4s)-3-알콕시-4-페닐-2-아제티디논의 선택적 제조방법
CN118894896A (zh) 一种制备线虫蛔苷和木糖苷二聚信息素的方法
JPS6344145B2 (OSRAM)
KR20090085808A (ko) 메틸제람블론의 제조방법 및 이를 위한 중간체

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20080508

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20080725

A711 Notification of change in applicant

Free format text: JAPANESE INTERMEDIATE CODE: A711

Effective date: 20090306

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A821

Effective date: 20090306

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20110816

A02 Decision of refusal

Free format text: JAPANESE INTERMEDIATE CODE: A02

Effective date: 20120124