UA77002C2 - Combined therapy in cancer treatment - Google Patents
Combined therapy in cancer treatment Download PDFInfo
- Publication number
- UA77002C2 UA77002C2 UA2004031862A UA2004031862A UA77002C2 UA 77002 C2 UA77002 C2 UA 77002C2 UA 2004031862 A UA2004031862 A UA 2004031862A UA 2004031862 A UA2004031862 A UA 2004031862A UA 77002 C2 UA77002 C2 UA 77002C2
- Authority
- UA
- Ukraine
- Prior art keywords
- alkyl
- hydrogen
- trifluoromethyl
- carboxylic acid
- group containing
- Prior art date
Links
- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 81
- 238000011282 treatment Methods 0.000 title claims abstract description 56
- 201000011510 cancer Diseases 0.000 title claims description 43
- 238000002648 combination therapy Methods 0.000 title description 8
- 238000000034 method Methods 0.000 claims abstract description 167
- 108010037462 Cyclooxygenase 2 Proteins 0.000 claims abstract description 28
- 102000010907 Cyclooxygenase 2 Human genes 0.000 claims abstract 12
- 229940124639 Selective inhibitor Drugs 0.000 claims abstract 12
- 150000001875 compounds Chemical class 0.000 claims description 262
- -1 piperazin-1-ylmethyl Chemical group 0.000 claims description 242
- 229910052739 hydrogen Inorganic materials 0.000 claims description 213
- 239000001257 hydrogen Substances 0.000 claims description 210
- 125000000217 alkyl group Chemical group 0.000 claims description 205
- 150000002431 hydrogen Chemical class 0.000 claims description 125
- 125000003118 aryl group Chemical group 0.000 claims description 99
- 125000003545 alkoxy group Chemical group 0.000 claims description 81
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 81
- 150000002367 halogens Chemical class 0.000 claims description 77
- 229910052736 halogen Inorganic materials 0.000 claims description 76
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 74
- 125000001072 heteroaryl group Chemical group 0.000 claims description 65
- 150000003839 salts Chemical class 0.000 claims description 46
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 28
- 239000003909 protein kinase inhibitor Substances 0.000 claims description 26
- 229940043355 kinase inhibitor Drugs 0.000 claims description 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 125000001188 haloalkyl group Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 229910052740 iodine Inorganic materials 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 229940093444 Cyclooxygenase 2 inhibitor Drugs 0.000 claims description 15
- 125000004104 aryloxy group Chemical group 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 239000003112 inhibitor Substances 0.000 claims description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 150000003254 radicals Chemical class 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 12
- 241000566113 Branta sandvicensis Species 0.000 claims description 11
- 241000124008 Mammalia Species 0.000 claims description 10
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 10
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 102000001253 Protein Kinase Human genes 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 8
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 235000013405 beer Nutrition 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000006262 isopropyl amino sulfonyl group Chemical group 0.000 claims description 4
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 claims description 3
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 claims description 3
- 241001415849 Strigiformes Species 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 229910052754 neon Inorganic materials 0.000 claims description 3
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 101000806248 Mus musculus Very-long-chain 3-oxoacyl-CoA reductase Proteins 0.000 claims description 2
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 3
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 2
- 125000004869 2,2-dimethylpropylcarbonyl group Chemical group CC(CC(=O)*)(C)C 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- KJOSDRUNXOPTEP-UHFFFAOYSA-N 5,7-dichloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(Cl)C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1Cl KJOSDRUNXOPTEP-UHFFFAOYSA-N 0.000 claims 1
- HMBUMPBGRPVQME-UHFFFAOYSA-N 6,7-dichloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=C(Cl)C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 HMBUMPBGRPVQME-UHFFFAOYSA-N 0.000 claims 1
- XSYDNZXQHVDCQR-UHFFFAOYSA-N 6,7-difluoro-2-(trifluoromethyl)-1,2-dihydroquinoline-3-carboxylic acid Chemical compound FC1=C(F)C=C2NC(C(F)(F)F)C(C(=O)O)=CC2=C1 XSYDNZXQHVDCQR-UHFFFAOYSA-N 0.000 claims 1
- QOQKUIZOHDRLNJ-UHFFFAOYSA-N 6,8-dibromo-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound BrC1=CC(Br)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 QOQKUIZOHDRLNJ-UHFFFAOYSA-N 0.000 claims 1
- YCPMOEZRKIIFKJ-UHFFFAOYSA-N 6,8-dichloro-2-(trifluoromethyl)-2h-thiochromene-3-carboxylic acid Chemical compound ClC1=CC(Cl)=C2SC(C(F)(F)F)C(C(=O)O)=CC2=C1 YCPMOEZRKIIFKJ-UHFFFAOYSA-N 0.000 claims 1
- UYZVEGRAOSUKSM-UHFFFAOYSA-N 6,8-ditert-butyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(C(C)(C)C)C=C2C(C)(C)C UYZVEGRAOSUKSM-UHFFFAOYSA-N 0.000 claims 1
- XRCIFEVLZNDSDG-UHFFFAOYSA-N 6-(4-hydroxybenzoyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=1C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=1C(=O)C1=CC=C(O)C=C1 XRCIFEVLZNDSDG-UHFFFAOYSA-N 0.000 claims 1
- YKJCXFQLAGEPJU-UHFFFAOYSA-N 6-iodo-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound IC1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 YKJCXFQLAGEPJU-UHFFFAOYSA-N 0.000 claims 1
- ZVWOGLMGGCMZOF-UHFFFAOYSA-N 7,8-dimethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C(C)C(C)=CC=C21 ZVWOGLMGGCMZOF-UHFFFAOYSA-N 0.000 claims 1
- ABNPGORLVYQTCX-UHFFFAOYSA-N 7-phenyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=C1C1=CC=CC=C1 ABNPGORLVYQTCX-UHFFFAOYSA-N 0.000 claims 1
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- DIUCLSCBUOAEQY-UHFFFAOYSA-N 8-chloro-6-methyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=CC(C)=CC(Cl)=C21 DIUCLSCBUOAEQY-UHFFFAOYSA-N 0.000 claims 1
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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AU2003295658A1 (en) * | 2002-11-27 | 2004-06-23 | Allergan, Inc. | Indol derivatives and their use as kinase inhibitors |
CA2510850A1 (en) | 2002-12-19 | 2004-07-08 | Pfizer Inc. | 2-(1h-indazol-6-ylamino)-benzamide compounds as protein kinases inhibitors useful for the treatment of ophthalmic diseases |
US7157577B2 (en) * | 2003-03-07 | 2007-01-02 | Sugen Inc. | 5-sulfonamido-substituted indolinone compounds as protein kinase inhibitors |
US20070123593A1 (en) * | 2003-10-08 | 2007-05-31 | Rose-Marie Dannenfelser | Pharmaceutical composition comprising 5-methyl-2(2'-chloro-6'-fluoroanilino)phenylacetic acid |
WO2005118543A1 (ja) * | 2004-06-03 | 2005-12-15 | Ono Pharmaceutical Co., Ltd. | キナーゼ阻害薬およびその用途 |
US20060009510A1 (en) * | 2004-07-09 | 2006-01-12 | Pharmacia & Upjohn Company Llc | Method of synthesizing indolinone compounds |
WO2006120557A1 (en) * | 2005-05-12 | 2006-11-16 | Pfizer Inc. | Anticancer combination therapy using sunitinib malate |
AU2006268315A1 (en) * | 2005-07-08 | 2007-01-18 | John P. Ford | Metered-dose and safety and compliance packaging for systemic anticancer therapy |
JP2010502741A (ja) * | 2006-09-11 | 2010-01-28 | キュリス,インコーポレイテッド | Ptkインヒビターとしての亜鉛結合部分を含む置換2−インドリノン |
US20090004213A1 (en) | 2007-03-26 | 2009-01-01 | Immatics Biotechnologies Gmbh | Combination therapy using active immunotherapy |
WO2009030270A1 (en) * | 2007-09-03 | 2009-03-12 | Novartis Ag | Dihydroindole derivatives useful in parkinson's disease |
GB0813873D0 (en) * | 2008-07-30 | 2008-09-03 | Univ Dundee | Compounds |
EP2181991A1 (en) * | 2008-10-28 | 2010-05-05 | LEK Pharmaceuticals D.D. | Novel salts of sunitinib |
EP2186809A1 (en) * | 2008-11-13 | 2010-05-19 | LEK Pharmaceuticals D.D. | New crystal form of sunitinib malate |
WO2012042421A1 (en) | 2010-09-29 | 2012-04-05 | Pfizer Inc. | Method of treating abnormal cell growth |
RU2495628C1 (ru) * | 2012-04-18 | 2013-10-20 | Государственное бюджетное учреждение здравоохранения Московской области "Московский областной научно-исследовательский клинический институт им. М.Ф. Владимирского" (ГБУЗ МО МОНИКИ им. М.Ф. Владимирского) | Способ выбора тактики лечения актинического кератоза |
TWI646091B (zh) * | 2012-12-28 | 2019-01-01 | 日商衛斯克慧特股份有限公司 | 鹽類及晶形 |
SG10201806965XA (en) * | 2013-03-13 | 2018-09-27 | Boston Biomedical Inc | 3-(aryl or heteroaryl) methyleneindolin-2-one derivatives as inhibitors of cancer stem cell pathway kinases for the treatment of cancer |
CN103923014A (zh) * | 2014-05-05 | 2014-07-16 | 宁夏宝马药业有限公司 | 环肌酸制备方法 |
KR20180100652A (ko) | 2016-01-08 | 2018-09-11 | 유클리세스 파마슈티컬스 인코포레이티드 | 크로멘 화합물 및 제2활성제의 조합물 |
CN111759883B (zh) * | 2020-07-23 | 2021-09-17 | 浙江农林大学 | 山核桃内果皮提取物在制备抗卵巢癌产品中的应用 |
CN114853736B (zh) * | 2022-07-06 | 2022-10-21 | 北京鑫开元医药科技有限公司 | 具有trk抑制活性的化合物、制备方法、组合物及其用途 |
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