TW200848030A - Benzoxazolone derivatives - Google Patents
Benzoxazolone derivatives Download PDFInfo
- Publication number
- TW200848030A TW200848030A TW097121279A TW97121279A TW200848030A TW 200848030 A TW200848030 A TW 200848030A TW 097121279 A TW097121279 A TW 097121279A TW 97121279 A TW97121279 A TW 97121279A TW 200848030 A TW200848030 A TW 200848030A
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- TW
- Taiwan
- Prior art keywords
- phenyl
- methyl
- acid
- group
- ester
- Prior art date
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- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical class C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 129
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- 238000011282 treatment Methods 0.000 claims abstract description 40
- FPYJSJDOHRDAMT-KQWNVCNZSA-N 1h-indole-5-sulfonamide, n-(3-chlorophenyl)-3-[[3,5-dimethyl-4-[(4-methyl-1-piperazinyl)carbonyl]-1h-pyrrol-2-yl]methylene]-2,3-dihydro-n-methyl-2-oxo-, (3z)- Chemical compound C=1C=C2NC(=O)\C(=C/C3=C(C(C(=O)N4CCN(C)CC4)=C(C)N3)C)C2=CC=1S(=O)(=O)N(C)C1=CC=CC(Cl)=C1 FPYJSJDOHRDAMT-KQWNVCNZSA-N 0.000 claims abstract description 20
- -1 hexahydropyridyl group Chemical group 0.000 claims description 175
- 238000000034 method Methods 0.000 claims description 167
- 239000000203 mixture Substances 0.000 claims description 153
- 238000002360 preparation method Methods 0.000 claims description 77
- 150000003839 salts Chemical class 0.000 claims description 66
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 50
- 239000002253 acid Substances 0.000 claims description 48
- 239000003795 chemical substances by application Substances 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 201000010099 disease Diseases 0.000 claims description 37
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 37
- 239000004480 active ingredient Substances 0.000 claims description 31
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 239000012453 solvate Substances 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 108091000080 Phosphotransferase Proteins 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 102000020233 phosphotransferase Human genes 0.000 claims description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
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- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 12
- 239000011734 sodium Substances 0.000 claims description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 230000005764 inhibitory process Effects 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000007789 gas Substances 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 8
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
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- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- JINGUCXQUOKWKH-UHFFFAOYSA-N 2-aminodecanoic acid Chemical compound CCCCCCCCC(N)C(O)=O JINGUCXQUOKWKH-UHFFFAOYSA-N 0.000 claims description 3
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- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
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- YOLHKYWNQMSMDN-UHFFFAOYSA-N 5-methoxy-3h-1,3-benzoxazol-2-one Chemical compound COC1=CC=C2OC(=O)NC2=C1 YOLHKYWNQMSMDN-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- 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
- C07D413/10—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 carbon chain containing aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
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- Oncology (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| DE102007032507A1 (de) | 2007-07-12 | 2009-04-02 | Merck Patent Gmbh | Pyridazinonderivate |
| DE102007038957A1 (de) * | 2007-08-17 | 2009-02-19 | Merck Patent Gmbh | 6-Thioxo-pyridazinderivate |
| DE102007061963A1 (de) | 2007-12-21 | 2009-06-25 | Merck Patent Gmbh | Pyridazinonderivate |
| DE102008019907A1 (de) * | 2008-04-21 | 2009-10-22 | Merck Patent Gmbh | Pyridazinonderivate |
| JP2011520986A (ja) | 2008-05-22 | 2011-07-21 | アムジエン・インコーポレーテツド | タンパク質キナーゼ阻害薬としての複素環類 |
| DE102008028905A1 (de) * | 2008-06-18 | 2009-12-24 | Merck Patent Gmbh | 3-(3-Pyrimidin-2-yl-benzyl)-[1,2,4]triazolo[4,3-b]pyridazinderivate |
| DE102008037790A1 (de) * | 2008-08-14 | 2010-02-18 | Merck Patent Gmbh | Bicyclische Triazolderivate |
| EA201170349A1 (ru) * | 2008-08-18 | 2011-08-30 | Йейл Юниверсити | Модуляторы mif |
| US9540322B2 (en) | 2008-08-18 | 2017-01-10 | Yale University | MIF modulators |
| US9643922B2 (en) | 2008-08-18 | 2017-05-09 | Yale University | MIF modulators |
| MY160526A (en) | 2008-12-22 | 2017-03-15 | Merck Patent Gmbh | Novel polymorphic forms of 6-(1-methyl-1h-pyrazol-4-yl)-2-{3-[5-(2-morpholin-4-yl-ethoxy)-pyrimidin-2-yl]-benzyl}-2h-pyridazin-3-one dihydrogenphosphate and processes of manufacturing thereof |
| DE102009003975A1 (de) * | 2009-01-07 | 2010-07-08 | Merck Patent Gmbh | Benzothiazolonderivate |
| WO2012003338A1 (en) | 2010-07-01 | 2012-01-05 | Takeda Pharmaceutical Company Limited | COMBINATION OF A cMET INHIBITOR AND AN ANTIBODY TO HGF AND/OR cMET |
| CA2840060A1 (en) | 2011-06-27 | 2013-01-03 | Kyorin Pharmaceutical Co., Ltd. | Bridged bicyclic compounds for the treatment of bacterial infections |
| CN103242345B (zh) * | 2012-09-14 | 2015-03-11 | 日出实业集团有限公司 | 甲基吡啶磷中间体6-氯噁唑[4,5-b]吡啶-2(3H)酮的合成方法 |
| AR095883A1 (es) * | 2013-04-18 | 2015-11-18 | Astellas Pharma Inc | Compuestos de acetamida heterocíclica |
| WO2014200872A1 (en) * | 2013-06-09 | 2014-12-18 | Rjs Biologics Llc | Pharmaceutical compounds targeted by mif affinity-tethered moieties |
| EP3229836B1 (en) | 2014-12-09 | 2019-11-13 | Institut National de la Sante et de la Recherche Medicale (INSERM) | Human monoclonal antibodies against axl |
| WO2016135041A1 (en) | 2015-02-26 | 2016-09-01 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Fusion proteins and antibodies comprising thereof for promoting apoptosis |
| KR101798840B1 (ko) | 2017-05-17 | 2017-11-17 | 주식회사 레고켐 바이오사이언스 | 신규 오토탁신 저해 화합물 및 이를 함유하는 약제학적 조성물 |
| JP2020524718A (ja) * | 2017-06-22 | 2020-08-20 | キュラデブ・ファーマ・リミテッドＣｕｒａｄｅｖ Ｐｈａｒｍａ Ｌｉｍｉｔｅｄ | ヒトｓｔｉｎｇの複素環式小分子調節因子 |
| ES2946551T3 (es) | 2017-10-17 | 2023-07-20 | Palau Pharma S L U | Síntesis de compuestos de 4-aminopirimidina |
| WO2020186202A1 (en) | 2019-03-14 | 2020-09-17 | Board Of Regents, The University Of Texas System | Small molecule grb2 stabilizers for ras map kinase inhibition |
| CN115490578B (zh) * | 2022-09-23 | 2023-12-22 | 江苏理工学院 | 一种碳同位素标记的三氯生的制备方法 |
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| BR9707495A (pt) | 1996-02-13 | 1999-07-27 | Zeneca Ltd | Derivado de quinazolina processo para a preparação do mesmo composição farmacêutica e processo para a produç o de um efeito antiangiogênico e/ou de redução de permeabilidade vascular em um animal de sangue quente |
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| JP2005516927A (ja) * | 2001-12-13 | 2005-06-09 | アボット・ラボラトリーズ | 癌治療用のキナーゼ阻害剤としての３−（フェニル−アルコキシ）−５−（フェニル）−ピリジン誘導体および関連化合物 |
| AU2003249597B2 (en) | 2002-03-08 | 2007-06-28 | Merck Sharp & Dohme Corp. | Mitotic kinesin inhibitors |
| UA77526C2 (en) | 2002-06-07 | 2006-12-15 | Sanofi Aventis | Substituted derivatives of 1-piperazineacylpiperidine, a method for the preparation thereof and their use in therapy |
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-
2007
- 2007-06-06 DE DE102007026341A patent/DE102007026341A1/de not_active Withdrawn
-
2008
- 2008-05-08 EP EP08749391A patent/EP2150551B1/de not_active Not-in-force
- 2008-05-08 WO PCT/EP2008/003696 patent/WO2008148449A1/de not_active Ceased
- 2008-05-08 BR BRPI0812293-8A2A patent/BRPI0812293A2/pt not_active IP Right Cessation
- 2008-05-08 KR KR1020107000014A patent/KR20100031531A/ko not_active Withdrawn
- 2008-05-08 ES ES08749391T patent/ES2402540T3/es active Active
- 2008-05-08 EA EA200901611A patent/EA200901611A1/ru unknown
- 2008-05-08 AU AU2008258366A patent/AU2008258366B2/en not_active Ceased
- 2008-05-08 MX MX2009013077A patent/MX2009013077A/es not_active Application Discontinuation
- 2008-05-08 CN CN2008800183950A patent/CN101679401B/zh not_active Expired - Fee Related
- 2008-05-08 US US12/663,206 patent/US8071593B2/en not_active Expired - Fee Related
- 2008-05-08 JP JP2010510658A patent/JP5662143B2/ja not_active Expired - Fee Related
- 2008-05-08 CA CA2689554A patent/CA2689554C/en active Active
- 2008-06-05 PE PE2008000958A patent/PE20090770A1/es not_active Application Discontinuation
- 2008-06-06 AR ARP080102415A patent/AR066892A1/es unknown
- 2008-06-06 TW TW097121279A patent/TW200848030A/zh unknown
-
2009
- 2009-12-03 IL IL202505A patent/IL202505A/en active IP Right Grant
-
2010
- 2010-01-05 ZA ZA201000085A patent/ZA201000085B/xx unknown
-
2011
- 2011-07-06 US US13/177,261 patent/US8431572B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2150551B1 (de) | 2013-01-16 |
| CA2689554C (en) | 2015-12-01 |
| EA200901611A1 (ru) | 2010-06-30 |
| EP2150551A1 (de) | 2010-02-10 |
| AU2008258366A1 (en) | 2008-12-11 |
| IL202505A (en) | 2014-11-30 |
| AR066892A1 (es) | 2009-09-16 |
| DE102007026341A1 (de) | 2008-12-11 |
| AU2008258366B2 (en) | 2013-02-21 |
| BRPI0812293A2 (pt) | 2014-11-25 |
| MX2009013077A (es) | 2010-01-15 |
| WO2008148449A1 (de) | 2008-12-11 |
| CN101679401A (zh) | 2010-03-24 |
| ES2402540T3 (es) | 2013-05-06 |
| CN101679401B (zh) | 2012-12-12 |
| US20100280030A1 (en) | 2010-11-04 |
| ZA201000085B (en) | 2010-09-29 |
| CA2689554A1 (en) | 2008-12-11 |
| US8071593B2 (en) | 2011-12-06 |
| JP2010529051A (ja) | 2010-08-26 |
| US20110263596A1 (en) | 2011-10-27 |
| JP5662143B2 (ja) | 2015-01-28 |
| US8431572B2 (en) | 2013-04-30 |
| KR20100031531A (ko) | 2010-03-22 |
| IL202505A0 (en) | 2010-06-30 |
| PE20090770A1 (es) | 2009-06-24 |
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