RU2470023C2 - 1-цианоциклопропильные производные в качестве ингибиторов катепсина к - Google Patents
1-цианоциклопропильные производные в качестве ингибиторов катепсина к Download PDFInfo
- Publication number
- RU2470023C2 RU2470023C2 RU2010101279/04A RU2010101279A RU2470023C2 RU 2470023 C2 RU2470023 C2 RU 2470023C2 RU 2010101279/04 A RU2010101279/04 A RU 2010101279/04A RU 2010101279 A RU2010101279 A RU 2010101279A RU 2470023 C2 RU2470023 C2 RU 2470023C2
- Authority
- RU
- Russia
- Prior art keywords
- cyanocyclopropyl
- carbonyl
- cyclohexanecarboxamide
- tetrahydro
- pyrido
- Prior art date
Links
- -1 1-cyanocyclopropyl Chemical class 0.000 title claims 34
- 102000005600 Cathepsins Human genes 0.000 title 1
- 108010084457 Cathepsins Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 13
- 150000003839 salts Chemical class 0.000 claims abstract 8
- 102000004171 Cathepsin K Human genes 0.000 claims abstract 7
- 108090000625 Cathepsin K Proteins 0.000 claims abstract 7
- 230000002401 inhibitory effect Effects 0.000 claims abstract 5
- 241000124008 Mammalia Species 0.000 claims abstract 4
- 239000003814 drug Substances 0.000 claims abstract 3
- 241001465754 Metazoa Species 0.000 claims abstract 2
- 230000005764 inhibitory process Effects 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 8
- 125000004122 cyclic group Chemical group 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- HGJTURTZFKNELD-HZPDHXFCSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(8-fluoro-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CCC=2NC3=CC=C(C=C3C=2C1)F)NC1(C#N)CC1 HGJTURTZFKNELD-HZPDHXFCSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- HGEJGPHBRGISQP-HZPDHXFCSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(6-hydroxy-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CC=2C=3C=CC=C(C=3NC=2CC1)O)NC1(C#N)CC1 HGEJGPHBRGISQP-HZPDHXFCSA-N 0.000 claims 1
- ZASVBBCQLDAKGY-RTBURBONSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(6-propoxy-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CC=2C=3C=CC=C(C=3NC=2CC1)OCCC)NC1(C#N)CC1 ZASVBBCQLDAKGY-RTBURBONSA-N 0.000 claims 1
- YXSHPPFCJPOWHN-QZTJIDSGSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(7-methylsulfonyl-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CC=2C3=CC=C(C=C3NC=2CC1)S(=O)(=O)C)NC1(C#N)CC1 YXSHPPFCJPOWHN-QZTJIDSGSA-N 0.000 claims 1
- IJKUEXZNTYMXCX-HZPDHXFCSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-(9-methylsulfonyl-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl)cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CCC=2NC=3C=CC=C(C=3C=2C1)S(=O)(=O)C)NC1(C#N)CC1 IJKUEXZNTYMXCX-HZPDHXFCSA-N 0.000 claims 1
- ACVZLIMCUJMGLB-WOJBJXKFSA-N (1r,2r)-n-(1-cyanocyclopropyl)-2-[6-[2-(dimethylamino)ethoxy]-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carbonyl]cyclohexane-1-carboxamide Chemical compound O=C([C@@H]1CCCC[C@H]1C(=O)N1CC=2C=3C=CC=C(C=3NC=2CC1)OCCN(C)C)NC1(C#N)CC1 ACVZLIMCUJMGLB-WOJBJXKFSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004452 carbocyclyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- NBJSZOLFWBVKSS-UHFFFAOYSA-N n-(1-cyanocyclopropyl)cyclohexanecarboxamide Chemical compound C1CCCCC1C(=O)NC1(C#N)CC1 NBJSZOLFWBVKSS-UHFFFAOYSA-N 0.000 claims 1
- WJTZYIZTLQJOFN-UHFFFAOYSA-N spiro[1h-isoquinoline-4,4'-piperidine] Chemical compound C1CNCCC21C1=CC=CC=C1CN=C2 WJTZYIZTLQJOFN-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract 2
- 102000005927 Cysteine Proteases Human genes 0.000 abstract 1
- 108010005843 Cysteine Proteases Proteins 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
-
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94617807P | 2007-06-26 | 2007-06-26 | |
| US60/946,178 | 2007-06-26 | ||
| US4284008P | 2008-04-07 | 2008-04-07 | |
| US61/042,840 | 2008-04-07 | ||
| PCT/GB2008/050486 WO2009001129A1 (en) | 2007-06-26 | 2008-06-24 | 1-cyanocyclopropyl-derivatives as cathepsin k inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2010101279A RU2010101279A (ru) | 2011-08-10 |
| RU2470023C2 true RU2470023C2 (ru) | 2012-12-20 |
Family
ID=39761131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010101279/04A RU2470023C2 (ru) | 2007-06-26 | 2008-06-24 | 1-цианоциклопропильные производные в качестве ингибиторов катепсина к |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8008279B2 (enExample) |
| EP (1) | EP2170879B1 (enExample) |
| JP (1) | JP2010531344A (enExample) |
| KR (1) | KR20100039862A (enExample) |
| CN (1) | CN101687864A (enExample) |
| AR (1) | AR067156A1 (enExample) |
| AU (1) | AU2008269513B2 (enExample) |
| BR (1) | BRPI0813306A2 (enExample) |
| CA (1) | CA2689945A1 (enExample) |
| CL (1) | CL2008001899A1 (enExample) |
| CO (1) | CO6251264A2 (enExample) |
| EC (1) | ECSP109882A (enExample) |
| IL (1) | IL202519A0 (enExample) |
| NZ (1) | NZ581719A (enExample) |
| PE (1) | PE20090841A1 (enExample) |
| RU (1) | RU2470023C2 (enExample) |
| TW (1) | TW200911806A (enExample) |
| UY (1) | UY31180A1 (enExample) |
| WO (1) | WO2009001129A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009089482A1 (en) | 2008-01-11 | 2009-07-16 | Albany Molecular Research, Inc. | (1-azinone) -substituted pyridoindoles as mch antagonists |
| JP5666036B2 (ja) * | 2008-01-25 | 2015-02-04 | メディベイション テクノロジーズ， インコーポレイテッド | 新規２，３，４，５−テトラヒドロ−１Ｈ−ピリド［４，３−ｂ］インドール化合物およびその使用方法 |
| RU2544856C2 (ru) | 2008-01-25 | 2015-03-20 | Сергей Олегович Бачурин | НОВЫЕ ПРОИЗВОДНЫЕ 2,3,4,5-ТЕТРАГИДРО-1-ПИРИДО[4,3-b]ИНДОЛА И СПОСОБЫ ИХ ПРИМЕНЕНИЯ |
| PA8843701A1 (es) | 2008-09-29 | 2010-05-26 | Abbott Lab | Derivados de indolina y métodos para usarlos |
| US9625475B2 (en) | 2008-09-29 | 2017-04-18 | Abbvie Inc. | Indole and indoline derivatives and methods of use thereof |
| WO2010080253A1 (en) * | 2008-12-18 | 2010-07-15 | Merck Patent Gmbh | Tricyclic azaindoles |
| US7893099B2 (en) * | 2009-06-11 | 2011-02-22 | Hoffman-La Roche Inc. | Cyclopentane derivatives |
| JP2012532144A (ja) * | 2009-07-01 | 2012-12-13 | アルバニー モレキュラー リサーチ， インコーポレイテッド | アジノン置換アゼピノ［ｂ］インドールおよびピリド−ピロロ−アゼピンｍｃｈ−１拮抗薬、ならびにその作製方法および使用 |
| US8629158B2 (en) * | 2009-07-01 | 2014-01-14 | Albany Molecular Research, Inc. | Azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine MCH-1 antagonists, methods of making, and use thereof |
| WO2011003021A1 (en) * | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine mch-1 antagonists, methods of making, and use thereof |
| US8618299B2 (en) * | 2009-07-01 | 2013-12-31 | Albany Molecular Research, Inc. | Azinone-substituted azapolycycle MCH-1 antagonists, methods of making, and use thereof |
| PH12012500775A1 (en) * | 2009-10-21 | 2012-11-26 | Boehringer Ingelheim Int | Indazole and pyrazolopyridine compounds as ccr1 receptor antagonists |
| US8927550B2 (en) | 2009-10-27 | 2015-01-06 | Boehringer Ingelheim International Gmbh | Heterocyclic compounds as CCR1 receptor antagonists |
| WO2011084433A2 (en) | 2009-12-17 | 2011-07-14 | Abbott Laboratories | Aza-bridged ring-fused indoles and indolines |
| US8524703B2 (en) | 2009-12-17 | 2013-09-03 | Abbvie Inc. | Bridgehead amine ring-fused indoles and indolines |
| WO2011137109A1 (en) | 2010-04-30 | 2011-11-03 | Boehringer Ingelheim International Gmbh | Azaindazole amide compounds as ccr1 receptor antagonists |
| WO2012088124A2 (en) | 2010-12-21 | 2012-06-28 | Albany Molecular Research, Inc. | Tetrahydro-azacarboline mch-1 antagonists, methods of making, and uses thereof |
| US8697700B2 (en) | 2010-12-21 | 2014-04-15 | Albany Molecular Research, Inc. | Piperazinone-substituted tetrahydro-carboline MCH-1 antagonists, methods of making, and uses thereof |
| US8815843B2 (en) | 2011-02-18 | 2014-08-26 | Medivation Technologies, Inc. | Compounds and methods of treating diabetes |
| JP6068505B2 (ja) * | 2012-01-11 | 2017-01-25 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | プロテアーゼ阻害剤としてのマクロ環式アミド |
| CN103086923B (zh) * | 2013-01-21 | 2014-04-23 | 吉林大学 | 肼腈类组织蛋白酶k抑制剂及其在治疗骨质疏松症方面的应用 |
| JP6454335B2 (ja) * | 2013-10-08 | 2019-01-16 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | カテプシンシステインプロテアーゼ阻害剤 |
| WO2016027285A2 (en) * | 2014-08-22 | 2016-02-25 | Alkem Laboratories Ltd. | Bicyclic heteroaryl amides as cathepsin cysteine protease inhibitors |
| CN105837479B (zh) * | 2016-04-05 | 2017-10-27 | 吉林大学 | 肼腈类组织蛋白酶k抑制剂及其在制备治疗骨关节炎药物中的应用 |
| IL302144A (en) * | 2017-03-29 | 2023-06-01 | Minerva Biotechnologies Corp | Agents for stem cell differentiation and cancer treatment |
| JP2025503082A (ja) * | 2022-01-21 | 2025-01-30 | 山東新時代薬業有限公司 | カテプシンｋ阻害剤及びその製造方法並びにその応用 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001009110A1 (en) * | 1999-07-30 | 2001-02-08 | Boehringer Ingelheim Pharmaceuticals, Inc. | Novel succinate derivative compounds useful as cysteine protease inhibitors |
| WO2003048123A1 (en) * | 2001-12-04 | 2003-06-12 | F. Hoffmann-La Roche Ag | Substituted 2-amino-cycloalkanecarboxamides and their use as cysteine protease inhibitors |
| US7012075B2 (en) * | 2001-03-02 | 2006-03-14 | Merck & Co., Inc. | Cathepsin cysteine protease inhibitors |
| RU2278863C2 (ru) * | 2001-08-10 | 2006-06-27 | Орто-Макнейл Фармасьютикал, Инк. | Замещенные пиразолы, фармацевтическая композиция и способ ингибирования активности катепсина s |
| EP1248612B1 (en) * | 2000-01-06 | 2008-02-27 | Merck Frosst Canada Ltd. | Novel compounds and compositions as protease inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2001245764A1 (en) | 2000-03-15 | 2001-09-24 | Axys Pharmaceuticals, Inc. | Novel compounds and compositions as protease inhibitors |
| SE0201977D0 (sv) * | 2002-06-24 | 2002-06-24 | Astrazeneca Ab | Novel compounds |
| SE0203712D0 (sv) | 2002-12-13 | 2002-12-13 | Astrazeneca Ab | Novel compounds |
| PL377426A1 (pl) | 2002-12-19 | 2006-02-06 | Bristol-Myers Squibb Company | Podstawione tricykliczne gamma-karboliny jako agoniści i antagoniści receptora serotoninowego |
-
2008
- 2008-06-24 CA CA2689945A patent/CA2689945A1/en not_active Abandoned
- 2008-06-24 RU RU2010101279/04A patent/RU2470023C2/ru not_active IP Right Cessation
- 2008-06-24 CN CN200880021955A patent/CN101687864A/zh active Pending
- 2008-06-24 BR BRPI0813306A patent/BRPI0813306A2/pt not_active IP Right Cessation
- 2008-06-24 NZ NZ581719A patent/NZ581719A/en not_active IP Right Cessation
- 2008-06-24 EP EP08776161A patent/EP2170879B1/en active Active
- 2008-06-24 JP JP2010514135A patent/JP2010531344A/ja active Pending
- 2008-06-24 WO PCT/GB2008/050486 patent/WO2009001129A1/en not_active Ceased
- 2008-06-24 KR KR1020107001848A patent/KR20100039862A/ko not_active Withdrawn
- 2008-06-24 AU AU2008269513A patent/AU2008269513B2/en not_active Ceased
- 2008-06-25 UY UY31180A patent/UY31180A1/es not_active Application Discontinuation
- 2008-06-25 TW TW097123686A patent/TW200911806A/zh unknown
- 2008-06-25 AR ARP080102722A patent/AR067156A1/es not_active Application Discontinuation
- 2008-06-25 US US12/145,855 patent/US8008279B2/en not_active Expired - Fee Related
- 2008-06-26 PE PE2008001087A patent/PE20090841A1/es not_active Application Discontinuation
- 2008-06-26 CL CL2008001899A patent/CL2008001899A1/es unknown
-
2009
- 2009-12-03 IL IL202519A patent/IL202519A0/en unknown
- 2009-12-22 CO CO09146663A patent/CO6251264A2/es not_active Application Discontinuation
-
2010
- 2010-01-15 EC EC2010009882A patent/ECSP109882A/es unknown
Patent Citations (5)
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| WO2001009110A1 (en) * | 1999-07-30 | 2001-02-08 | Boehringer Ingelheim Pharmaceuticals, Inc. | Novel succinate derivative compounds useful as cysteine protease inhibitors |
| EP1248612B1 (en) * | 2000-01-06 | 2008-02-27 | Merck Frosst Canada Ltd. | Novel compounds and compositions as protease inhibitors |
| US7012075B2 (en) * | 2001-03-02 | 2006-03-14 | Merck & Co., Inc. | Cathepsin cysteine protease inhibitors |
| RU2278863C2 (ru) * | 2001-08-10 | 2006-06-27 | Орто-Макнейл Фармасьютикал, Инк. | Замещенные пиразолы, фармацевтическая композиция и способ ингибирования активности катепсина s |
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Also Published As
| Publication number | Publication date |
|---|---|
| PE20090841A1 (es) | 2009-08-02 |
| EP2170879B1 (en) | 2013-01-16 |
| WO2009001129A1 (en) | 2008-12-31 |
| CA2689945A1 (en) | 2008-12-31 |
| KR20100039862A (ko) | 2010-04-16 |
| EP2170879A1 (en) | 2010-04-07 |
| WO2009001129A9 (en) | 2010-02-04 |
| NZ581719A (en) | 2011-08-26 |
| CO6251264A2 (es) | 2011-02-21 |
| JP2010531344A (ja) | 2010-09-24 |
| AR067156A1 (es) | 2009-09-30 |
| AU2008269513B2 (en) | 2011-06-16 |
| BRPI0813306A2 (pt) | 2017-05-16 |
| US8008279B2 (en) | 2011-08-30 |
| UY31180A1 (es) | 2009-01-30 |
| AU2008269513A1 (en) | 2008-12-31 |
| RU2010101279A (ru) | 2011-08-10 |
| US20090012077A1 (en) | 2009-01-08 |
| TW200911806A (en) | 2009-03-16 |
| CN101687864A (zh) | 2010-03-31 |
| IL202519A0 (en) | 2010-06-30 |
| ECSP109882A (es) | 2010-02-26 |
| CL2008001899A1 (es) | 2009-07-17 |
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