CA2121523A1 - Sulfonamide derivatives - Google Patents

Sulfonamide derivatives

Info

Publication number
CA2121523A1
CA2121523A1 CA002121523A CA2121523A CA2121523A1 CA 2121523 A1 CA2121523 A1 CA 2121523A1 CA 002121523 A CA002121523 A CA 002121523A CA 2121523 A CA2121523 A CA 2121523A CA 2121523 A1 CA2121523 A1 CA 2121523A1
Authority
CA
Canada
Prior art keywords
cathepsin
sulfonamide derivatives
amyotrophia
calpain
hypercalcemia
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
CA002121523A
Other languages
French (fr)
Other versions
CA2121523C (en
Inventor
Ryoichi Ando
Toshiro Sakaki
Chizuko Takahashi
Yoshiyuki Fujimura
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.)
Mitsubishi Chemical Corp
Original Assignee
Ryoichi Ando
Toshiro Sakaki
Chizuko Takahashi
Yoshiyuki Fujimura
Mitsubishi Chemical Corporation
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 Ryoichi Ando, Toshiro Sakaki, Chizuko Takahashi, Yoshiyuki Fujimura, Mitsubishi Chemical Corporation filed Critical Ryoichi Ando
Publication of CA2121523A1 publication Critical patent/CA2121523A1/en
Application granted granted Critical
Publication of CA2121523C publication Critical patent/CA2121523C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C07K5/06043—Leu-amino acid
    • 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
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • 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
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/12—Ophthalmic agents for cataracts
    • 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
    • A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
    • A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
    • 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
    • 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
    • A61P9/08—Vasodilators for multiple indications
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C07D213/71—Sulfur atoms to which a second hetero atom is attached

Abstract

The present invention is directed to sulfonamide derivatives of the general formula (I):
(see formula I) wherein R is C6-14 aryl or a heterocyclic residue each of which may have one or more substituents or the salt thereof. The sulfonamide derivatives show strong inhibitory activity against cysteine protease such as calpain papain, cathepsin B, cathepsin H, cathepsin L. They can be used as remedies for muscular dystrophy, cataract, myocardial infarction, stroke, amyotrophia, osteoporosis, hypercalcemia or the like.
CA002121523A 1993-04-28 1994-04-18 Sulfonamide derivatives Expired - Fee Related CA2121523C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP102782/1993 1993-04-28
JP10278293 1993-04-28

Publications (2)

Publication Number Publication Date
CA2121523A1 true CA2121523A1 (en) 1994-10-29
CA2121523C CA2121523C (en) 2006-06-20

Family

ID=14336717

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002121523A Expired - Fee Related CA2121523C (en) 1993-04-28 1994-04-18 Sulfonamide derivatives

Country Status (10)

Country Link
US (1) US5506243A (en)
EP (1) EP0623627B1 (en)
JP (1) JP3599287B2 (en)
AT (1) ATE145214T1 (en)
CA (1) CA2121523C (en)
DE (1) DE69400887T2 (en)
DK (1) DK0623627T3 (en)
ES (1) ES2096370T3 (en)
GR (1) GR3022524T3 (en)
TW (1) TW261608B (en)

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US5804560A (en) * 1995-01-06 1998-09-08 Sibia Neurosciences, Inc. Peptide and peptide analog protease inhibitors
US6017887A (en) * 1995-01-06 2000-01-25 Sibia Neurosciences, Inc. Peptide, peptide analog and amino acid analog protease inhibitors
DE69625622T2 (en) * 1995-10-25 2003-08-14 Senju Pharma Co Angiogenesis inhibitors
EP0928786B1 (en) * 1995-10-25 2003-01-02 Senju Pharmaceutical Co., Ltd. Angiogenesis inhibitor
US6214800B1 (en) 1995-10-25 2001-04-10 Senju Pharmaceutical Co., Ltd. Angiogenesis inhibitor
EP0910564B1 (en) * 1995-11-28 2007-10-31 Cephalon, Inc. D-amino acid derived inhibitors of cysteine and serine proteases
US6653331B2 (en) * 1996-07-03 2003-11-25 Pharmacia & Upjohn Company Targeted drug delivery using sulfonamide derivatives
AU3805497A (en) * 1996-07-19 1998-02-10 Neurotrauma Therapeutics, Inc. Calpain inhibitors for the treatment of traumatic brain injury
WO1998003191A1 (en) * 1996-07-19 1998-01-29 Neurotrauma Therapeutics, Inc. Calpain inhibitors for the treatment of cerebral ischemia, spinal cord injury or stroke
WO1998018485A1 (en) 1996-10-31 1998-05-07 Alcon Laboratories, Inc. The use of calpain inhibitors to treat ocular neural pathology
NZ335480A (en) 1996-12-31 2001-04-27 Guilford Pharm Inc Neurotrophic low molecular weight N-linked sulfonamides of heterocyclic thioesters and their use as inhibitors of immunophilin proteins
US5874449A (en) * 1996-12-31 1999-02-23 Gpi Nil Holdings, Inc. N-linked sulfonamides of heterocyclic thioesters
AR013079A1 (en) * 1997-05-06 2000-12-13 Smithkline Beecham Corp SUBSTITUTED DERIVATIVES OF TETRAHIDROFURANO-3-ONAS, TETRAHIDROPIRANO-3- ONAS AND TETRAHIDROTIOFEN-3-ONAS, A PROCEDURE FOR THE PREPARATION OF A PHARMACEUTICAL COMPOSITION OF A MEDICINAL PRODUCT USEFUL AS INTERMEDIATE PROTEIN INHIBITORS
AU2745599A (en) * 1998-03-05 1999-09-20 Senju Pharmaceutical Co., Ltd. Pharmaceutical composition for prophylaxis and therapy of diseases associated with ocular fundus tissue cytopathy
CN1295561A (en) 1998-06-03 2001-05-16 Gpinil控股公司 N-linked sulfonamides of N-heterocyclic carboxylic acids or carboxylic acid isosteres
US6331537B1 (en) 1998-06-03 2001-12-18 Gpi Nil Holdings, Inc. Carboxylic acids and carboxylic acid isosteres of N-heterocyclic compounds
WO2000021550A2 (en) * 1998-10-13 2000-04-20 President And Fellows Of Harvard College Methods and compositions for treating neurodegenerative diseases
US7253169B2 (en) 1999-11-12 2007-08-07 Gliamed, Inc. Aza compounds, pharmaceutical compositions and methods of use
US6417189B1 (en) 1999-11-12 2002-07-09 Gpi Nil Holdings, Inc. AZA compounds, pharmaceutical compositions and methods of use
EP1244670B1 (en) 1999-12-21 2006-03-08 MGI GP, Inc. Hydantoin derivative compounds, pharmaceutical compositions, and methods of using same
KR20020067702A (en) * 2000-01-26 2002-08-23 오노 야꾸힝 고교 가부시키가이샤 Nitrogen-containing 5-membered cyclic compounds and drugs containing these compounds as the active ingredient
US6803233B2 (en) * 2000-07-31 2004-10-12 The Regents Of The University Of California Model for Alzheimer's disease and other neurodegenerative diseases
AU2001292287A1 (en) * 2000-10-26 2002-05-06 Senju Pharmaceutical Co. Ltd. Drug composition comprising dipeptydyl aldehyde derivative
ATE330950T1 (en) * 2000-12-13 2006-07-15 Wyeth Corp HETEROCYCLIC SULFONAMIDES AS INHIBITORS OF BETA-AMYLOID PRODUCTION
JP4549851B2 (en) * 2002-07-22 2010-09-22 千寿製薬株式会社 Novel α-ketoamide derivatives and uses thereof
US7662849B2 (en) 2003-06-04 2010-02-16 Virobay, Inc. Amidino compounds as cysteine protease inhibitors
SG146658A1 (en) 2003-09-18 2008-10-30 Schering Ag Haloalkyl containing compounds as cysteine protease inhibitors
US8163735B2 (en) 2004-12-02 2012-04-24 Virobay, Inc. Sulfonamide compounds as cysteine protease inhibitors
EA017874B1 (en) 2005-03-21 2013-03-29 Вайробей, Инк. Alpha ketoamide compounds as cysteine protease inhibitors
JP5215167B2 (en) 2005-03-22 2013-06-19 ビロベイ，インコーポレイティド Compounds containing sulfonyl groups as cysteine protease inhibitors
WO2008045017A2 (en) * 2005-06-22 2008-04-17 Diamond Scott L Sars and ebola inhibitors and use thereof, and methods for their discovery
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
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
EP3755352A4 (en) * 2018-02-20 2021-12-22 Edgewise Therapeutics, Inc. Methods and compositions for treating movement disorders
JP7355777B2 (en) 2021-03-31 2023-10-03 本田技研工業株式会社 Cutting tools
WO2024018245A1 (en) 2022-07-22 2024-01-25 INSERM (Institut National de la Santé et de la Recherche Médicale) Use of calpain inhibitors for the treatment of the diabetic kidney disease

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5754157A (en) * 1980-09-19 1982-03-31 Nippon Kayaku Co Ltd L-argininal derivative and its preparation
JP2701932B2 (en) * 1989-04-10 1998-01-21 サントリー株式会社 Protease inhibitor
EP0504938A3 (en) * 1991-03-22 1993-04-14 Suntory Limited Prophylactic and therapeutic agent for bone diseases comprising di- or tripeptide derivative as active ingredient

Also Published As

Publication number Publication date
DE69400887T2 (en) 1997-05-22
US5506243A (en) 1996-04-09
DK0623627T3 (en) 1997-04-28
DE69400887D1 (en) 1996-12-19
GR3022524T3 (en) 1997-05-31
JP3599287B2 (en) 2004-12-08
EP0623627B1 (en) 1996-11-13
JPH0748340A (en) 1995-02-21
ATE145214T1 (en) 1996-11-15
CA2121523C (en) 2006-06-20
TW261608B (en) 1995-11-01
ES2096370T3 (en) 1997-03-01
EP0623627A1 (en) 1994-11-09

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