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RU2005131502A - Ингибиторы катепсина s - Google Patents

Ингибиторы катепсина s Download PDF

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Publication number
RU2005131502A
RU2005131502A RU2005131502/04A RU2005131502A RU2005131502A RU 2005131502 A RU2005131502 A RU 2005131502A RU 2005131502/04 A RU2005131502/04 A RU 2005131502/04A RU 2005131502 A RU2005131502 A RU 2005131502A RU 2005131502 A RU2005131502 A RU 2005131502A
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Russia
Prior art keywords
compound
alkyl
disease
pharmaceutically acceptable
carbon atom
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RU2005131502/04A
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English (en)
Inventor
Юджин Р. ХИККИ (US)
Юджин Р. ХИККИ
Вейминь ЛЮ (US)
Вейминь Лю
Саньсин СУНЬ (US)
Саньсин СУНЬ
Янси Дейвид УОРД (US)
Янси Дейвид УОРД
Эрик Ричард Рауш ЯНГ (US)
Эрик Ричард Рауш ЯНГ
Original Assignee
Берингер Ингельхайм Фармасьютиклз, Инк. (Us)
Берингер Ингельхайм Фармасьютиклз, Инк.
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Publication of RU2005131502A publication Critical patent/RU2005131502A/ru

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    • 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
    • C07D211/66—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having a hetero atom as the second substituent in position 4
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/06—Antipsoriatics
    • 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
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms 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

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Neurology (AREA)
  • Pulmonology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Obesity (AREA)
  • Rheumatology (AREA)
  • Urology & Nephrology (AREA)
  • Dermatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Hematology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Vascular Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Transplantation (AREA)
  • Pregnancy & Childbirth (AREA)
  • Emergency Medicine (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Pain & Pain Management (AREA)

Claims (11)

1. Соединение формулы (I) или (II)
Figure 00000001
Figure 00000002
в котором Х в каждом случае выбирают из
Figure 00000003
Figure 00000004
Figure 00000005
Figure 00000006
и
Figure 00000007
;
R1 выбирают из водорода или разветвленного алкила, или алкила с прямой цепью, где каждый атом углерода в цепи необязательно заменен одним-тремя гетероатомами, выбранными из О, S и NR2, где R2 означает водород или алкил;
и где R1, кроме того, необязательно замещен одной или несколькими группами, выбранными из алкокси, амина, галогена, карбоцикла, гетероарила или гетероцикла;
или его фармацевтически приемлемые соли.
2. Соединение по п.1, в котором
в формуле (I)
Figure 00000001
Х выбирают из
Figure 00000008
;
R1 выбирают из водорода или C1-С10алкила с разветвленной цепью или С1-С10алкила с прямой цепью, где каждый атом углерода в цепи необязательно заменен одним-тремя гетероатомами, выбранными из О, S или N-R2, где R2 означает водород или С1-С5алкил;
и где R1, кроме того, необязательно замещен одной или несколькими группами, выбранными из С1-С5алкокси, амина, гетероцикла или галогена.
3. Соединение по п.1 или 2, где R1 означает С1-С5алкил.
4. Соединение по п.1 или 2, в котором R1 означает C1-С3алкил, предпочтительно метил.
5. Соединение по п.1 или 2, в котором R1 выбирают из
Figure 00000009
;
Figure 00000010
;
Figure 00000011
и
Figure 00000012
.
6. Соединение по п.1 или 2, где соединение формулы (I) представлено (S) энантиомером, который обладает конфигурацией природной аминокислоты при показанном ниже хиральном атоме углерода.
Figure 00000013
7. Соединение, выбранное из
Figure 00000014
;
Figure 00000015
;
Figure 00000016
;
Figure 00000017
;
Figure 00000018
и
Figure 00000019
или его фармацевтически приемлемые соли.
8. Соединение или его фармацевтически приемлемые соли, где соединение представлено
Figure 00000020
в котором показанный хиральный атом углерода соответствует (S) энантиомеру, обладающему конфигурацией природной аминокислоты.
9. Соединение, выбранное из
Figure 00000021
;
Figure 00000022
;
Figure 00000023
;
Figure 00000024
;
Figure 00000025
и
Figure 00000026
;
или его фармацевтически приемлемых солей.
10. Применение соединений по пп.1-9 для лечения заболевания или состояния, выбранного из ревматоидного артрита, системной волчанки, болезни Крона, язвенного колита, рассеянного склероза, синдрома Гийена-Барра, псориаза, болезни Грейвса, тяжелой псевдопаралитической миастении, склеродермии, гломерулонефрита, дерматитов, включая контактный и аллергический дерматиты, инсулин-зависимого диабета, эндометриоза, астмы, болезни Альцгеймера и атеросклероза.
11. Применение соединений по пп.1-9 для приготовления фармацевтической композиции, подходящей для лечения аутоиммунного заболевания или состояния, нарушений, связанных с неадекватными аутоиммунными ответами, иммунных ответов, опосредованных Т-клетками или внеклеточным протеолизом, опосредованным катепсином S.
RU2005131502/04A 2003-03-13 2004-03-03 Ингибиторы катепсина s RU2005131502A (ru)

Applications Claiming Priority (2)

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US45423903P 2003-03-13 2003-03-13
US60/454,239 2003-03-13

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RU2005131502A true RU2005131502A (ru) 2006-08-27

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US (1) US7326719B2 (ru)
EP (1) EP1606258A1 (ru)
JP (1) JP4455506B2 (ru)
KR (1) KR20050109553A (ru)
CN (1) CN100400511C (ru)
AR (1) AR043563A1 (ru)
AU (1) AU2004221860A1 (ru)
BR (1) BRPI0408299A (ru)
CA (1) CA2518728A1 (ru)
MX (1) MXPA05008240A (ru)
NZ (1) NZ542905A (ru)
PE (1) PE20050312A1 (ru)
RU (1) RU2005131502A (ru)
TW (1) TW200509919A (ru)
WO (1) WO2004083182A1 (ru)
ZA (1) ZA200505418B (ru)

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WO2005028429A2 (en) 2003-09-18 2005-03-31 Axys Pharmaceuticals, Inc. Haloalkyl containing compounds as cysteine protease inhibitors
US7186827B2 (en) * 2003-10-30 2007-03-06 Boehringer Ingelheim Pharmaceuticals, Inc. Dipeptide synthesis
JP2007513972A (ja) * 2003-12-11 2007-05-31 アクシス・ファーマシューティカルズ・インコーポレイテッド 低分子治療剤または生物製剤の投与によって引き起こされる免疫応答を治療するためのカテプシンｓインヒビターの使用
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
CA2602175C (en) 2005-03-21 2012-11-27 Applera Corporation Alpha ketoamide compounds as cysteine protease inhibitors
CA2602112A1 (en) 2005-03-22 2006-09-28 Celera Genomics Sulfonyl containing compounds as cysteine protease inhibitors
KR101486763B1 (ko) 2006-10-04 2015-01-28 비로베이, 인코포레이티드 시스테인 프로테아제 억제제로서의 디­플루오로 함유 화합물
US7893112B2 (en) 2006-10-04 2011-02-22 Virobay, Inc. Di-fluoro containing compounds as cysteine protease inhibitors
EP2216047A4 (en) * 2007-10-24 2011-12-28 Nat Univ Corp Tokyo Med & Dent Regulator for signaling of toll-like receptor, which comprises cathepsin inhibitor as active ingredient
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
DE102009028929A1 (de) * 2009-08-27 2011-07-07 Bayer Schering Pharma Aktiengesellschaft, 13353 Heterocyclisch-substituierte 2-Acetamido-5-Aryl-1,2,4-triazolone und deren Verwendung
US8729114B2 (en) 2010-03-05 2014-05-20 Boehringer Ingelheim International Gmbh Heteroaryl nitrile compounds useful as inhibitors of Cathepsin-S
CN106715472A (zh) * 2014-09-18 2017-05-24 豪夫迈·罗氏有限公司 用于监测组织蛋白酶s抑制的方法
WO2020201572A1 (en) 2019-04-05 2020-10-08 Université De Bretagne Occidentale Protease-activated receptor-2 inhibitors for the treatment of sensory neuropathy induced by a marine neurotoxic poisoning
EP4234014A1 (en) * 2022-02-28 2023-08-30 Insusense ApS Amino acid based carbamates and/or ureas for the treatment of sortilin dependent diseases

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US5776718A (en) * 1995-03-24 1998-07-07 Arris Pharmaceutical Corporation Reversible protease inhibitors
GB9723407D0 (en) * 1997-11-05 1998-01-07 Ciba Geigy Ag Organic compounds
BR9813197A (pt) 1997-11-05 2000-08-29 Novartis Ag Dipeptìdeo nitrilas
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
EP1159273A1 (en) 1999-03-02 2001-12-05 Boehringer Ingelheim Pharmaceuticals Inc. Compounds useful as reversible inhibitors of cathepsin s
JP2002539190A (ja) * 1999-03-15 2002-11-19 アクシス・ファーマシューティカルズ・インコーポレイテッド プロテアーゼ阻害剤としての新規化合物および組成物
US6420364B1 (en) * 1999-09-13 2002-07-16 Boehringer Ingelheim Pharmaceuticals, Inc. Compound useful as reversible inhibitors of cysteine proteases
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US6982263B2 (en) * 2001-06-08 2006-01-03 Boehringer Ingelheim Pharmaceuticals, Inc. Nitriles useful as reversible inhibitors of cysteine proteases

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AU2004221860A1 (en) 2004-09-30
AR043563A1 (es) 2005-08-03
KR20050109553A (ko) 2005-11-21
CN1761652A (zh) 2006-04-19
MXPA05008240A (es) 2005-10-05
WO2004083182A1 (en) 2004-09-30
US20040180886A1 (en) 2004-09-16
JP2006519768A (ja) 2006-08-31
TW200509919A (en) 2005-03-16
ZA200505418B (en) 2007-01-31
JP4455506B2 (ja) 2010-04-21
BRPI0408299A (pt) 2006-03-07
US7326719B2 (en) 2008-02-05
CA2518728A1 (en) 2004-09-30
PE20050312A1 (es) 2005-06-14
NZ542905A (en) 2009-04-30
EP1606258A1 (en) 2005-12-21
CN100400511C (zh) 2008-07-09

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