JP6336598B2 - 抗増殖性化合物 - Google Patents
抗増殖性化合物 Download PDFInfo
- Publication number
- JP6336598B2 JP6336598B2 JP2016540387A JP2016540387A JP6336598B2 JP 6336598 B2 JP6336598 B2 JP 6336598B2 JP 2016540387 A JP2016540387 A JP 2016540387A JP 2016540387 A JP2016540387 A JP 2016540387A JP 6336598 B2 JP6336598 B2 JP 6336598B2
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- JP
- Japan
- Prior art keywords
- alkyl
- carbocyclyl
- heterocyclyl
- alkynyl
- alkenyl
- 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.)
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- 150000001875 compounds Chemical class 0.000 title claims description 278
- 230000001028 anti-proliverative effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 207
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 199
- 239000000203 mixture Substances 0.000 claims description 181
- -1 amino, hydroxyl Chemical group 0.000 claims description 176
- 125000000623 heterocyclic group Chemical group 0.000 claims description 175
- 150000003839 salts Chemical class 0.000 claims description 104
- 125000005843 halogen group Chemical group 0.000 claims description 100
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 85
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 84
- 229910052739 hydrogen Inorganic materials 0.000 claims description 80
- 229910052799 carbon Inorganic materials 0.000 claims description 79
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 78
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 77
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 68
- 238000011282 treatment Methods 0.000 claims description 63
- 206010028980 Neoplasm Diseases 0.000 claims description 59
- 229940127089 cytotoxic agent Drugs 0.000 claims description 57
- 125000003342 alkenyl group Chemical group 0.000 claims description 53
- 125000000304 alkynyl group Chemical group 0.000 claims description 53
- 229910052757 nitrogen Inorganic materials 0.000 claims description 51
- 201000011510 cancer Diseases 0.000 claims description 45
- 125000004043 oxo group Chemical group O=* 0.000 claims description 45
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 43
- 239000002254 cytotoxic agent Substances 0.000 claims description 40
- 231100000599 cytotoxic agent Toxicity 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000004429 atom Chemical group 0.000 claims description 24
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
- 125000002883 imidazolyl group Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 14
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000001246 bromo group Chemical group Br* 0.000 claims description 12
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000004423 acyloxy group Chemical group 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
- 230000002062 proliferating effect Effects 0.000 claims description 9
- 239000002671 adjuvant Substances 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 230000000069 prophylactic effect Effects 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 description 159
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 117
- 239000000243 solution Substances 0.000 description 97
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- 238000005481 NMR spectroscopy Methods 0.000 description 66
- 235000019439 ethyl acetate Nutrition 0.000 description 59
- 239000007787 solid Substances 0.000 description 58
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
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- 239000011734 sodium Substances 0.000 description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 description 15
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 description 15
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 15
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 description 15
- 238000002953 preparative HPLC Methods 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 14
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- 229940088598 enzyme Drugs 0.000 description 14
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- 125000005842 heteroatom Chemical group 0.000 description 13
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- 208000024891 symptom Diseases 0.000 description 11
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
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- A61K31/28—Compounds containing heavy metals
- A61K31/282—Platinum compounds
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- A—HUMAN NECESSITIES
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
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- A—HUMAN NECESSITIES
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- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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| US11124795B2 (en) | 2017-02-28 | 2021-09-21 | University Of Massachusetts | Genetic and pharmacological transcriptional upregulation of the repressed FXN gene as a therapeutic strategy for Friedreich ataxia |
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| UA73073C2 (uk) | 1997-04-03 | 2005-06-15 | Уайт Холдінгз Корпорейшн | Заміщені 3-ціанохіноліни, спосіб їх одержання та фармацевтична композиція |
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| IL135622A0 (en) | 1997-11-06 | 2001-05-20 | American Cyanamid Co | Use of quinazoline derivatives as tyrosine kinase inhibitors for treating colonic polyps |
| CA2349721A1 (en) | 1998-11-19 | 2000-06-02 | Warner-Lambert Company | N-¬4-(3-chloro-4-fluoro-phenylamino)-7-(3-morpholin-4-yl-propoxy)-quinazolin-6-yl|-acrylamide, an irreversible inhibitor of tyrosine kinases |
| TWI271406B (en) | 1999-12-13 | 2007-01-21 | Eisai Co Ltd | Tricyclic condensed heterocyclic compounds, preparation method of the same and pharmaceuticals comprising the same |
| JP4100865B2 (ja) * | 1999-12-13 | 2008-06-11 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 三環式縮合異項環化合物、その製造法およびその医薬 |
| DE60319820T2 (de) | 2002-06-04 | 2009-03-26 | Schering Corp. | Pyrazoloä1,5-aüpyrimidin-verbindungen als antivirale agentien |
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| MX2008016339A (es) * | 2006-06-20 | 2009-01-16 | Abbott Lab | Pirazoloquinazolinonas en la forma de inhibidores parp. |
| WO2010086040A1 (en) | 2009-01-29 | 2010-08-05 | Biomarin Iga, Ltd. | Pyrazolo-pyrimidines for treatment of duchenne muscular dystrophy |
| CN101906105B (zh) * | 2009-06-08 | 2013-01-16 | 河北医科大学 | 吡唑并[1，5-a]嘧啶酮衍生物及其药物组合物以及其用途 |
| WO2012149157A2 (en) * | 2011-04-26 | 2012-11-01 | Bioenergenix | Heterocyclic compounds for the inhibition of pask |
| WO2014066795A1 (en) * | 2012-10-25 | 2014-05-01 | Bioenergenix | Heterocyclic compounds for the inhibition of pask |
| ES2635016T3 (es) * | 2013-03-01 | 2017-10-02 | Fundación Para La Investigación Médica Aplicada | Nuevos compuestos como inhibidores duales de fosfodiesterasas e histonas deacetilasas |
| KR20150130491A (ko) | 2013-03-13 | 2015-11-23 | 제넨테크, 인크. | 피라졸로 화합물 및 그것의 용도 |
-
2014
- 2014-09-04 JP JP2016540387A patent/JP6336598B2/ja active Active
- 2014-09-04 KR KR1020167008823A patent/KR20160049003A/ko not_active Withdrawn
- 2014-09-04 CA CA2922925A patent/CA2922925A1/en not_active Abandoned
- 2014-09-04 US US14/477,566 patent/US9505767B2/en active Active
- 2014-09-04 WO PCT/US2014/054114 patent/WO2015035062A1/en not_active Ceased
- 2014-09-04 CN CN201480055129.0A patent/CN105611933B/zh active Active
- 2014-09-04 EP EP14766355.3A patent/EP3041474B1/en active Active
- 2014-09-04 RU RU2016112568A patent/RU2016112568A/ru not_active Application Discontinuation
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Also Published As
| Publication number | Publication date |
|---|---|
| CN105611933A (zh) | 2016-05-25 |
| MX2016002794A (es) | 2016-09-13 |
| CN105611933B (zh) | 2019-01-25 |
| RU2016112568A (ru) | 2017-10-06 |
| EP3041474A1 (en) | 2016-07-13 |
| US9505767B2 (en) | 2016-11-29 |
| CA2922925A1 (en) | 2015-03-12 |
| KR20160049003A (ko) | 2016-05-04 |
| JP2016529312A (ja) | 2016-09-23 |
| HK1221421A1 (zh) | 2017-06-02 |
| EP3041474B1 (en) | 2020-03-18 |
| WO2015035062A1 (en) | 2015-03-12 |
| RU2016112568A3 (enExample) | 2018-08-08 |
| US20150065522A1 (en) | 2015-03-05 |
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