TW200303863A - Substituted indazoles, compositions comprising them, manufacturing process and use - Google Patents

Info

Publication number

TW200303863A

TW200303863A TW092103799A TW92103799A TW200303863A TW 200303863 A TW200303863 A TW 200303863A TW 092103799 A TW092103799 A TW 092103799A TW 92103799 A TW92103799 A TW 92103799A TW 200303863 A TW200303863 A TW 200303863A

Authority

TW

Taiwan

Prior art keywords

indazol

indazole

substituted

formula

phenyl

Prior art date

2002-03-11

Links

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• Global Dossier
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• 238000004519 manufacturing process Methods 0.000 title claims abstract 3
• 239000000203 mixture Chemical class 0.000 title abstract description 28
• 150000002473 indoazoles Chemical class 0.000 title abstract description 8
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 25
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 25
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 19
• -1 lutein amine Chemical class 0.000 claims description 173
• 150000001875 compounds Chemical class 0.000 claims description 121
• 229940124530 sulfonamide Drugs 0.000 claims description 31
• 150000003456 sulfonamides Chemical class 0.000 claims description 23
• 125000000623 heterocyclic group Chemical group 0.000 claims description 18
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 16
• 206010028980 Neoplasm Diseases 0.000 claims description 16
• 125000003118 aryl group Chemical group 0.000 claims description 16
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims description 15
• 125000000217 alkyl group Chemical group 0.000 claims description 15
• HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 15
• 101100481408 Danio rerio tie2 gene Proteins 0.000 claims description 14
• 101100481410 Mus musculus Tek gene Proteins 0.000 claims description 14
• 125000001072 heteroaryl group Chemical group 0.000 claims description 14
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• 125000001424 substituent group Chemical group 0.000 claims description 12
• 201000011510 cancer Diseases 0.000 claims description 11
• 150000003839 salts Chemical class 0.000 claims description 11
• 108090000461 Aurora Kinase A Proteins 0.000 claims description 10
• 102100032311 Aurora kinase A Human genes 0.000 claims description 10
• 125000003342 alkenyl group Chemical group 0.000 claims description 10
• 125000003107 substituted aryl group Chemical class 0.000 claims description 10
• 101150001535 SRC gene Proteins 0.000 claims description 8
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 6
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• 238000011282 treatment Methods 0.000 claims description 5
• YTCROYMIRGBRIQ-UHFFFAOYSA-N 5-[(2-methylsulfonylphenyl)sulfonylamino]-1h-indazole-3-carboxamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC1=CC=C(NN=C2C(N)=O)C2=C1 YTCROYMIRGBRIQ-UHFFFAOYSA-N 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 239000003814 drug Substances 0.000 claims description 4
• 229910052736 halogen Inorganic materials 0.000 claims description 4
• 150000002367 halogens Chemical class 0.000 claims description 4
• 229910052705 radium Inorganic materials 0.000 claims description 4
• 229910052701 rubidium Inorganic materials 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 230000001575 pathological effect Effects 0.000 claims description 3
• 125000004426 substituted alkynyl group Chemical class 0.000 claims description 3
• 208000024891 symptom Diseases 0.000 claims description 3
• MUMNFEPQABVDQS-UHFFFAOYSA-N 2-methylsulfonylbenzenesulfonamide Chemical compound CS(=O)(=O)C1=CC=CC=C1S(N)(=O)=O MUMNFEPQABVDQS-UHFFFAOYSA-N 0.000 claims description 2
• XVCOPODOXQGYFA-UHFFFAOYSA-N 3-fluoro-n-(3-oxo-1,2-dihydroindazol-5-yl)benzenesulfonamide Chemical compound C1=C2C(O)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 XVCOPODOXQGYFA-UHFFFAOYSA-N 0.000 claims description 2
• OZYAXQWHHTUDPI-UHFFFAOYSA-N 5-[(3-fluorophenyl)sulfonylamino]-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)N)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 OZYAXQWHHTUDPI-UHFFFAOYSA-N 0.000 claims description 2
• YIMOCMSIWHYZRI-UHFFFAOYSA-N 5-[(3-fluorophenyl)sulfonylamino]-n-methyl-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=NNC2=CC=C1NS(=O)(=O)C1=CC=CC(F)=C1 YIMOCMSIWHYZRI-UHFFFAOYSA-N 0.000 claims description 2
• 238000006555 catalytic reaction Methods 0.000 claims description 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims description 2
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• 239000000126 substance Substances 0.000 claims 2
• 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 1
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• 150000001336 alkenes Chemical class 0.000 claims 1
• NPLNXWYFAJPNLA-UHFFFAOYSA-N aminosulfamic acid;benzene Chemical compound C1=CC=CC=C1.NNS(O)(=O)=O NPLNXWYFAJPNLA-UHFFFAOYSA-N 0.000 claims 1
• OTCCXZVWOGOSDR-UHFFFAOYSA-N benzene;sulfamic acid Chemical compound NS(O)(=O)=O.C1=CC=CC=C1 OTCCXZVWOGOSDR-UHFFFAOYSA-N 0.000 claims 1
• 238000010586 diagram Methods 0.000 claims 1
• 125000001153 fluoro group Chemical group F* 0.000 claims 1
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• 235000012680 lutein Nutrition 0.000 claims 1
• 239000001656 lutein Substances 0.000 claims 1
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
• 239000002689 soil Substances 0.000 claims 1
• KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 claims 1
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• 230000001225 therapeutic effect Effects 0.000 abstract description 4
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 44
• 239000007787 solid Substances 0.000 description 41
• 238000000034 method Methods 0.000 description 38
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 36
• 210000004027 cell Anatomy 0.000 description 36
• 230000008018 melting Effects 0.000 description 34
• 238000002844 melting Methods 0.000 description 34
• 238000006243 chemical reaction Methods 0.000 description 32
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
• CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 30
• 101000878536 Homo sapiens Focal adhesion kinase 1 Proteins 0.000 description 29
• 230000000694 effects Effects 0.000 description 29
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• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
• 239000000047 product Substances 0.000 description 24
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• 238000012360 testing method Methods 0.000 description 22
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• 238000000921 elemental analysis Methods 0.000 description 21
• 238000002474 experimental method Methods 0.000 description 21
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• 239000000243 solution Substances 0.000 description 21
• 239000003480 eluent Substances 0.000 description 20
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
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• 238000002360 preparation method Methods 0.000 description 14
• 229940086542 triethylamine Drugs 0.000 description 14
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 13
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
• 235000019341 magnesium sulphate Nutrition 0.000 description 13
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• 229910052757 nitrogen Inorganic materials 0.000 description 10
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• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 8
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