BRPI0922109A2 - composto derivado de benzotiazol, pró-droga, medicamento, e, uso do composto - Google Patents

Info

Publication number

BRPI0922109A2

BRPI0922109A2 BRPI0922109-3A BRPI0922109A BRPI0922109A2 BR PI0922109 A2 BRPI0922109 A2 BR PI0922109A2 BR PI0922109 A BRPI0922109 A BR PI0922109A BR PI0922109 A2 BRPI0922109 A2 BR PI0922109A2

Authority

BR

Brazil

Prior art keywords

compound

group

optionally

cyano

amino

Prior art date

2008-12-02

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims description 389
• 239000003814 drug Substances 0.000 title claims description 85
• 229940002612 prodrug Drugs 0.000 title claims description 17
• 239000000651 prodrug Substances 0.000 title claims description 17
• 229940079593 drug Drugs 0.000 title description 50
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title description 3
• -1 (trifluoromethyl) phenyl Chemical group 0.000 claims description 313
• 125000001424 substituent group Chemical group 0.000 claims description 167
• 125000005843 halogen group Chemical group 0.000 claims description 84
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 81
• 238000004519 manufacturing process Methods 0.000 claims description 67
• 150000003839 salts Chemical class 0.000 claims description 51
• 125000000217 alkyl group Chemical group 0.000 claims description 45
• 239000003112 inhibitor Substances 0.000 claims description 45
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 35
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 35
• 206010028980 Neoplasm Diseases 0.000 claims description 30
• 201000011510 cancer Diseases 0.000 claims description 30
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 29
• 125000003118 aryl group Chemical group 0.000 claims description 29
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 28
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
• 125000000623 heterocyclic group Chemical group 0.000 claims description 22
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
• 125000003277 amino group Chemical group 0.000 claims description 14
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 11
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 10
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
• 125000002947 alkylene group Chemical group 0.000 claims description 8
• 125000005102 carbonylalkoxy group Chemical group 0.000 claims description 8
• 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 5
• 229940126585 therapeutic drug Drugs 0.000 claims description 5
• 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims description 4
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
• 230000000069 prophylactic effect Effects 0.000 claims description 4
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 3
• 241001024304 Mino Species 0.000 claims description 3
• 229940043274 prophylactic drug Drugs 0.000 claims description 3
• 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 2
• 101100502609 Caenorhabditis elegans fem-1 gene Proteins 0.000 claims 1
• 101100334582 Drosophila melanogaster Fem-1 gene Proteins 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 343
• 229910052739 hydrogen Inorganic materials 0.000 description 122
• 239000000243 solution Substances 0.000 description 116
• 230000002829 reductive effect Effects 0.000 description 108
• 238000006243 chemical reaction Methods 0.000 description 99
• 239000000203 mixture Substances 0.000 description 95
• 238000002360 preparation method Methods 0.000 description 94
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 87
• 239000003795 chemical substances by application Substances 0.000 description 78
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 72
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 71
• 235000002639 sodium chloride Nutrition 0.000 description 63
• 239000002904 solvent Substances 0.000 description 63
• 239000000706 filtrate Substances 0.000 description 53
• 239000011541 reaction mixture Substances 0.000 description 53
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 52
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
• 239000002198 insoluble material Substances 0.000 description 52
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
• 229910052757 nitrogen Inorganic materials 0.000 description 48
• 238000000034 method Methods 0.000 description 45
• 239000002253 acid Substances 0.000 description 43
• 238000005160 1H NMR spectroscopy Methods 0.000 description 41
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
• 239000000843 powder Substances 0.000 description 40
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 38
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 37
• 235000017557 sodium bicarbonate Nutrition 0.000 description 35
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 35
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 34
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
• 238000001914 filtration Methods 0.000 description 32
• 239000007924 injection Substances 0.000 description 32
• 238000002347 injection Methods 0.000 description 32
• 238000004440 column chromatography Methods 0.000 description 31
• 229910052731 fluorine Inorganic materials 0.000 description 31
• 239000000741 silica gel Substances 0.000 description 31
• 229910002027 silica gel Inorganic materials 0.000 description 31
• 229910052717 sulfur Inorganic materials 0.000 description 31
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
• 239000007864 aqueous solution Substances 0.000 description 30
• 125000001153 fluoro group Chemical group F* 0.000 description 30
• 229910052801 chlorine Inorganic materials 0.000 description 29
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 27
• 125000001309 chloro group Chemical group Cl* 0.000 description 26
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
• 230000000694 effects Effects 0.000 description 24
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 24
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 23
• 239000000546 pharmaceutical excipient Substances 0.000 description 23
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 22
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
• 239000002585 base Substances 0.000 description 22
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 20
• 238000010438 heat treatment Methods 0.000 description 20
• 239000000126 substance Substances 0.000 description 20
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 19
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 19
• 239000010408 film Substances 0.000 description 19
• 230000035484 reaction time Effects 0.000 description 19
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 18
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 18
• 150000002170 ethers Chemical class 0.000 description 18
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 17
• 150000001298 alcohols Chemical class 0.000 description 17
• 150000008282 halocarbons Chemical class 0.000 description 17
• 229920000642 polymer Polymers 0.000 description 17
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 16
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 16
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
• KKVYYGGCHJGEFJ-UHFFFAOYSA-N 1-n-(4-chlorophenyl)-6-methyl-5-n-[3-(7h-purin-6-yl)pyridin-2-yl]isoquinoline-1,5-diamine Chemical compound N=1C=CC2=C(NC=3C(=CC=CN=3)C=3C=4N=CNC=4N=CN=3)C(C)=CC=C2C=1NC1=CC=C(Cl)C=C1 KKVYYGGCHJGEFJ-UHFFFAOYSA-N 0.000 description 15
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
• 101100381978 Mus musculus Braf gene Proteins 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 15
• 229910052708 sodium Inorganic materials 0.000 description 15
• 239000011734 sodium Substances 0.000 description 15
• 229940083542 sodium Drugs 0.000 description 15
• 239000007858 starting material Substances 0.000 description 15
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
• 230000002401 inhibitory effect Effects 0.000 description 14
• 239000003921 oil Substances 0.000 description 14
• 235000019198 oils Nutrition 0.000 description 14
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
• 229920002472 Starch Polymers 0.000 description 13
• 229920002678 cellulose Polymers 0.000 description 13
• 239000012729 immediate-release (IR) formulation Substances 0.000 description 13
• 239000012046 mixed solvent Substances 0.000 description 13
• 229920006395 saturated elastomer Polymers 0.000 description 13
• 239000008107 starch Substances 0.000 description 13
• 235000019698 starch Nutrition 0.000 description 13
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
• 238000011282 treatment Methods 0.000 description 13
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 12
• 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 12
• 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 description 12
• 238000005917 acylation reaction Methods 0.000 description 12
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• 125000002950 monocyclic group Chemical group 0.000 description 12
• 239000000047 product Substances 0.000 description 12
• 230000002035 prolonged effect Effects 0.000 description 12
• 239000003381 stabilizer Substances 0.000 description 12
• 239000000654 additive Substances 0.000 description 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
• 235000010980 cellulose Nutrition 0.000 description 11
• 230000035772 mutation Effects 0.000 description 11
• 238000001356 surgical procedure Methods 0.000 description 11
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 10
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
• 150000003863 ammonium salts Chemical class 0.000 description 10
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 10
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• 230000032050 esterification Effects 0.000 description 10
• 235000003599 food sweetener Nutrition 0.000 description 10
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 10
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 10
• 239000003446 ligand Substances 0.000 description 10
• 239000000314 lubricant Substances 0.000 description 10
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
• 229910052763 palladium Inorganic materials 0.000 description 10
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• 239000001267 polyvinylpyrrolidone Substances 0.000 description 10
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
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• 125000003226 pyrazolyl group Chemical group 0.000 description 10
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• 229920002125 Sokalan® Polymers 0.000 description 9
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• 229910000073 phosphorus hydride Inorganic materials 0.000 description 8
• ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 8
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