JP5713999B2 - アミド化合物、その製造方法及びそれを含む薬学組成物 - Google Patents
アミド化合物、その製造方法及びそれを含む薬学組成物 Download PDFInfo
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- JP5713999B2 JP5713999B2 JP2012510756A JP2012510756A JP5713999B2 JP 5713999 B2 JP5713999 B2 JP 5713999B2 JP 2012510756 A JP2012510756 A JP 2012510756A JP 2012510756 A JP2012510756 A JP 2012510756A JP 5713999 B2 JP5713999 B2 JP 5713999B2
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- JP
- Japan
- Prior art keywords
- methyl
- aminophenyl
- benzamide
- oxoisoindoline
- bromo
- 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.)
- Expired - Fee Related
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 245
- 150000001875 compounds Chemical class 0.000 claims description 221
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims description 209
- 239000000126 substance Substances 0.000 claims description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 11
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- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 6
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- KIPJIVDSUCESGM-UHFFFAOYSA-N n-(2-aminophenyl)-4-[[3-oxo-7-(4-phenoxyphenyl)-1h-isoindol-2-yl]methyl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CN1C(=O)C(C=CC=C2C=3C=CC(OC=4C=CC=CC=4)=CC=3)=C2C1 KIPJIVDSUCESGM-UHFFFAOYSA-N 0.000 claims description 3
- OZJARHJCNXYKJQ-UHFFFAOYSA-N n-(2-aminophenyl)-4-[[3-oxo-7-(4-phenylphenyl)-1h-isoindol-2-yl]methyl]benzamide Chemical compound NC1=CC=CC=C1NC(=O)C(C=C1)=CC=C1CN1C(=O)C(C=CC=C2C=3C=CC(=CC=3)C=3C=CC=CC=3)=C2C1 OZJARHJCNXYKJQ-UHFFFAOYSA-N 0.000 claims description 3
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- 150000003460 sulfonic acids Chemical class 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 230000002463 transducing effect Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
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- XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 1
- 229960004276 zoledronic acid Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
-
- 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
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- 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
- 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
- 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
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Oncology (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020090042691A KR101142053B1 (ko) | 2009-05-15 | 2009-05-15 | 이소인돌리논 유도체, 이의 제조방법 및 이를 포함하는 약학 조성물 |
| KR10-2009-0042691 | 2009-05-15 | ||
| KR1020090042585A KR20100123379A (ko) | 2009-05-15 | 2009-05-15 | 벤즈아마이드 유도체, 이의 제조방법 및 이를 포함하는 골 질환의 예방 및 치료용 약학 조성물 |
| KR10-2009-0042585 | 2009-05-15 | ||
| PCT/KR2010/003060 WO2010131922A2 (en) | 2009-05-15 | 2010-05-14 | Amide compound, preparation method thereof and pharmaceutical composition comprising same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012526803A JP2012526803A (ja) | 2012-11-01 |
| JP2012526803A5 JP2012526803A5 (https=) | 2014-09-11 |
| JP5713999B2 true JP5713999B2 (ja) | 2015-05-07 |
Family
ID=43085472
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012510756A Expired - Fee Related JP5713999B2 (ja) | 2009-05-15 | 2010-05-14 | アミド化合物、その製造方法及びそれを含む薬学組成物 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US8716326B2 (https=) |
| EP (1) | EP2429987A4 (https=) |
| JP (1) | JP5713999B2 (https=) |
| WO (1) | WO2010131922A2 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2330894B8 (en) | 2008-09-03 | 2017-04-19 | BioMarin Pharmaceutical Inc. | Compositions including 6-aminohexanoic acid derivatives as hdac inhibitors |
| TWI600638B (zh) * | 2010-01-22 | 2017-10-01 | 艾斯特隆製藥公司 | 作爲蛋白質去乙醯酶抑制劑之反式醯胺化合物及其使用方法 |
| US10059723B2 (en) | 2011-02-28 | 2018-08-28 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US9540395B2 (en) | 2011-02-28 | 2017-01-10 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| US8957066B2 (en) | 2011-02-28 | 2015-02-17 | Biomarin Pharmaceutical Inc. | Histone deacetylase inhibitors |
| CN102850236B (zh) * | 2011-06-27 | 2016-05-18 | 国药一心制药有限公司 | 新型苯甲酰胺类组蛋白去乙酰化酶抑制剂及其应用 |
| US9512083B2 (en) | 2011-07-20 | 2016-12-06 | The General Hospital Corporation | Histone deacetylase 6 selective inhibitors for the treatment of bone disease |
| WO2014143666A1 (en) | 2013-03-15 | 2014-09-18 | Biomarin Pharmaceutical Inc. | Hdac inhibitors |
| EP2801569A1 (en) * | 2013-05-09 | 2014-11-12 | Ikerchem, S.L. | Histone deacetylase inhibitors based on derivatives of tricyclic polyhydroacridine and analogs possessing fused saturated five- and seven-membered rings |
| ES2929576T3 (es) | 2013-10-08 | 2022-11-30 | Acetylon Pharmaceuticals Inc | Combinaciones de inhibidores de histona deacetilasa 6 y el inhibidor de Her2 lapatinib para el uso en el tratamiento del cáncer de mama |
| US10660890B2 (en) | 2013-10-24 | 2020-05-26 | National Institutes Of Health (Nih), U.S. Dept. Of Health And Human Services (Dhhs), U.S. Government Nih Division Of Extramural Inventions And Technology Resources (Deitr) | Treatment of polycystic diseases with an HDAC6 inhibitor |
| CR20160308A (es) | 2013-12-03 | 2016-11-08 | Acetylon Pharmaceuticals Inc | Combinaciones de inhibidores de histona deacetilasa y farmacos inmunomoduladores |
| SG11201700094TA (en) | 2014-07-07 | 2017-02-27 | Acetylon Pharmaceuticals Inc | Treatment of leukemia with histone deacetylase inhibitors |
| US9937174B2 (en) | 2014-12-05 | 2018-04-10 | University of Modena and Reggio Emilia | Combinations of histone deacetylase inhibitors and bendamustine |
| AR104935A1 (es) | 2015-06-08 | 2017-08-23 | Acetylon Pharmaceuticals Inc | Formas cristalinas de un inhibidor de histona deacetilasa |
| AR105812A1 (es) | 2015-06-08 | 2017-11-15 | Acetylon Pharmaceuticals Inc | Métodos para la preparación de inhibidores de proteína deacetilasa |
| EP3365334B1 (en) | 2015-10-21 | 2024-07-17 | Otsuka Pharmaceutical Co., Ltd. | Benzolactam compounds as protein kinase inhibitors |
| EP3445364A4 (en) | 2016-04-19 | 2019-11-27 | Acetylon Pharmaceuticals, Inc. | HDAC INHIBITORS, ONLY OR IN COMBINATION WITH BTK INHIBITORS, FOR THE TREATMENT OF CHRONIC LYMPHOCYTIC LEUKEMIA |
| US11324744B2 (en) | 2016-08-08 | 2022-05-10 | Acetylon Pharmaceuticals Inc. | Methods of use and pharmaceutical combinations of histone deacetylase inhibitors and CD20 inhibitory antibodies |
| GB201706327D0 (en) | 2017-04-20 | 2017-06-07 | Otsuka Pharma Co Ltd | A pharmaceutical compound |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4077998A (en) * | 1975-10-28 | 1978-03-07 | Morton-Norwich Products, Inc. | Phthaloyl amino acid hydroxamic acids |
| KR100194535B1 (ko) * | 1995-12-27 | 1999-06-15 | 우종일 | 아릴 벤조일 우레아 유도체 및 이를 함유하는 농약조성물 |
| KR100194534B1 (ko) * | 1996-06-29 | 1999-06-15 | 우종일 | 2-클로로-3,5-비스 (트피플루오르메틸) 페닐 벤조일 우레아 유도체 및 이의 제조방법 |
| US6174905B1 (en) | 1996-09-30 | 2001-01-16 | Mitsui Chemicals, Inc. | Cell differentiation inducer |
| EP1024134A4 (en) * | 1997-10-09 | 2003-05-14 | Ono Pharmaceutical Co | DERIVATIVES OF AMINOBUTANIC ACID |
| EP1335898B1 (en) * | 2000-09-29 | 2005-11-23 | TopoTarget UK Limited | Carbamic acid compounds comprising an amide linkage as hdac inhibitors |
| JPWO2002074298A1 (ja) * | 2001-03-21 | 2004-07-08 | 小野薬品工業株式会社 | Ｉｌ−６産生阻害剤 |
| US7868204B2 (en) * | 2001-09-14 | 2011-01-11 | Methylgene Inc. | Inhibitors of histone deacetylase |
| US20050215601A1 (en) * | 2002-09-25 | 2005-09-29 | Santen Pharmaceutical Co., Ltd. | Therapeutic agent for rheumatic disease comprising benzamide derivative as active ingredient |
| AU2003292888A1 (en) * | 2002-12-27 | 2004-07-22 | Schering Aktiengesellschaft | Pharmaceutical combinations of phthalazine vegf inhibitors and benzamide hdac inhibitors |
| JP4939941B2 (ja) * | 2003-08-26 | 2012-05-30 | 株式會社アモーレパシフィック | ヒドロキサム酸誘導体及びその製造方法 |
| KR100848073B1 (ko) * | 2004-12-14 | 2008-07-24 | 주식회사바이오러넥스 | Ｒｕｎｘ2를 아세틸화하여 Ｒｕｎｘ2 활성을증가시킴으로써 ＢＭＰ에 의한 골형성 경로를 활성화시키는방법 |
| US20100278782A1 (en) * | 2006-06-12 | 2010-11-04 | Vrije Universiteit Brussel | Differentiation of rat liver epithelial cells into hepatocyte-like cells |
| EP3103791B1 (en) * | 2007-06-27 | 2018-01-31 | Merck Sharp & Dohme Corp. | 4-carboxybenzylamino derivatives as histone deacetylase inhibitors |
| EP2330894B8 (en) * | 2008-09-03 | 2017-04-19 | BioMarin Pharmaceutical Inc. | Compositions including 6-aminohexanoic acid derivatives as hdac inhibitors |
-
2010
- 2010-05-14 US US13/320,117 patent/US8716326B2/en not_active Expired - Fee Related
- 2010-05-14 WO PCT/KR2010/003060 patent/WO2010131922A2/en not_active Ceased
- 2010-05-14 EP EP10775124A patent/EP2429987A4/en not_active Withdrawn
- 2010-05-14 JP JP2012510756A patent/JP5713999B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2012526803A (ja) | 2012-11-01 |
| WO2010131922A2 (en) | 2010-11-18 |
| WO2010131922A4 (en) | 2011-05-26 |
| EP2429987A2 (en) | 2012-03-21 |
| US20120065396A1 (en) | 2012-03-15 |
| EP2429987A4 (en) | 2012-10-03 |
| WO2010131922A3 (en) | 2011-03-24 |
| US8716326B2 (en) | 2014-05-06 |
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