BR112013028846B1 - Composto ou sal farmaceuticamente aceitável do mesmo, respectivos usos, processo de preparação, intermediários e composição farmacêutica - Google Patents

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Publication number

BR112013028846B1

BR112013028846B1 BR112013028846-9A BR112013028846A BR112013028846B1 BR 112013028846 B1 BR112013028846 B1 BR 112013028846B1 BR 112013028846 A BR112013028846 A BR 112013028846A BR 112013028846 B1 BR112013028846 B1 BR 112013028846B1

Authority

BR

Brazil

Prior art keywords

amino

pyrimidin

carbonyl

pyrazolo

methyl

Prior art date

2011-05-17

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 399
• 150000003839 salts Chemical class 0.000 title claims abstract description 157
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 19
• 239000000543 intermediate Substances 0.000 title description 3
• 238000002360 preparation method Methods 0.000 title description 3
• -1 her4 Proteins 0.000 claims abstract description 116
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 21
• 201000011510 cancer Diseases 0.000 claims abstract description 18
• 206010003246 arthritis Diseases 0.000 claims abstract description 16
• 208000027866 inflammatory disease Diseases 0.000 claims abstract description 16
• 125000000217 alkyl group Chemical group 0.000 claims description 394
• 229910052739 hydrogen Inorganic materials 0.000 claims description 236
• 239000001257 hydrogen Substances 0.000 claims description 234
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 175
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 127
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 114
• 239000011737 fluorine Substances 0.000 claims description 113
• 229910052731 fluorine Inorganic materials 0.000 claims description 113
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 106
• 125000005843 halogen group Chemical group 0.000 claims description 104
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 98
• 125000003545 alkoxy group Chemical group 0.000 claims description 84
• 125000001424 substituent group Chemical group 0.000 claims description 79
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 75
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 64
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 59
• 229910052760 oxygen Inorganic materials 0.000 claims description 48
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 45
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 44
• 239000000460 chlorine Substances 0.000 claims description 44
• 229910052801 chlorine Inorganic materials 0.000 claims description 44
• 125000004476 heterocycloamino group Chemical group 0.000 claims description 43
• 229920006395 saturated elastomer Polymers 0.000 claims description 42
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 40
• 125000005842 heteroatom Chemical group 0.000 claims description 35
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 35
• 239000000203 mixture Substances 0.000 claims description 35
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 30
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
• 239000003814 drug Substances 0.000 claims description 29
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 29
• 229910052799 carbon Inorganic materials 0.000 claims description 28
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 27
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 25
• 210000003719 b-lymphocyte Anatomy 0.000 claims description 22
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 21
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 21
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 21
• MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 claims description 20
• 125000004486 1-methylpiperidin-3-yl group Chemical group CN1CC(CCC1)* 0.000 claims description 19
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 19
• 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 19
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 19
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 18
• 125000004432 carbon atom Chemical group C* 0.000 claims description 18
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 17
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 16
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 16
• 239000002253 acid Substances 0.000 claims description 14
• 239000002246 antineoplastic agent Substances 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 12
• 201000004624 Dermatitis Diseases 0.000 claims description 11
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
• 238000006243 chemical reaction Methods 0.000 claims description 11
• 208000023275 Autoimmune disease Diseases 0.000 claims description 10
• 125000001153 fluoro group Chemical group F* 0.000 claims description 10
• XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 239000005977 Ethylene Substances 0.000 claims description 7
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• NNJAGWVFMOGWLK-XMMPIXPASA-N 2-[(3R)-3-[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-3-[1-(diethylaminomethyl)cyclopentyl]prop-2-enenitrile Chemical compound C([C@@H](CCC1)N2C3=NC=NC(N)=C3C(C=3C(=CC(OC=4C(=C(F)C=CC=4)F)=CC=3)F)=N2)N1C(=O)C(C#N)=CC1(CN(CC)CC)CCCC1 NNJAGWVFMOGWLK-XMMPIXPASA-N 0.000 claims description 2
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• YOEWVNKRGSFIBQ-MUMRKEEXSA-N 2-[(3R)-3-[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-3-pyrrolidin-2-ylprop-2-enenitrile Chemical compound C1=2C(N)=NC=NC=2N([C@H]2CN(CCC2)C(=O)C(=CC2NCCC2)C#N)N=C1C(C(=C1)F)=CC=C1OC1=CC=CC(F)=C1F YOEWVNKRGSFIBQ-MUMRKEEXSA-N 0.000 claims description 2
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• BTWNIXPKIHIIBT-SANMLTNESA-N 2-[(3S)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-3-[1-(diethylaminomethyl)cyclopentyl]prop-2-enenitrile Chemical compound C([C@H](CCC1)N2C3=NC=NC(N)=C3C(C=3C(=CC(OC=4C=CC=CC=4)=CC=3)F)=N2)N1C(=O)C(C#N)=CC1(CN(CC)CC)CCCC1 BTWNIXPKIHIIBT-SANMLTNESA-N 0.000 claims description 2
• SONFNRMAPPWUNU-NRFANRHFSA-N 2-[(3S)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-3-[1-(ethylamino)cyclopropyl]prop-2-enenitrile Chemical compound C([C@H](CCC1)N2C3=NC=NC(N)=C3C(C=3C(=CC(OC=4C=CC=CC=4)=CC=3)F)=N2)N1C(=O)C(C#N)=CC1(NCC)CC1 SONFNRMAPPWUNU-NRFANRHFSA-N 0.000 claims description 2
• GCYHPPFYYPCIBY-FQEVSTJZSA-N 2-[(3S)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-3-[1-(methylamino)cyclopropyl]prop-2-enenitrile Chemical compound C([C@H](CCC1)N2C3=NC=NC(N)=C3C(C=3C(=CC(OC=4C=CC=CC=4)=CC=3)F)=N2)N1C(=O)C(C#N)=CC1(NC)CC1 GCYHPPFYYPCIBY-FQEVSTJZSA-N 0.000 claims description 2
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• AFAVFCVQCOJERG-DEOSSOPVSA-N 2-[(3S)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-3-[1-[(dimethylamino)methyl]cyclopentyl]prop-2-enenitrile Chemical compound C([C@H](CCC1)N2C3=NC=NC(N)=C3C(C=3C(=CC(OC=4C=CC=CC=4)=CC=3)F)=N2)N1C(=O)C(C#N)=CC1(CN(C)C)CCCC1 AFAVFCVQCOJERG-DEOSSOPVSA-N 0.000 claims description 2
• FXSMLAZXJKANGS-IAXKEJLGSA-N 2-[(3S)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-3-piperidin-3-ylprop-2-enenitrile Chemical compound C1=2C(N)=NC=NC=2N([C@@H]2CN(CCC2)C(=O)C(=CC2CNCCC2)C#N)N=C1C(C(=C1)F)=CC=C1OC1=CC=CC=C1 FXSMLAZXJKANGS-IAXKEJLGSA-N 0.000 claims description 2
• KIHVEXSGLLUDHS-LBAQZLPGSA-N 2-[(3S)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-3-pyrrolidin-2-ylprop-2-enenitrile Chemical compound C1=2C(N)=NC=NC=2N([C@@H]2CN(CCC2)C(=O)C(=CC2NCCC2)C#N)N=C1C(C(=C1)F)=CC=C1OC1=CC=CC=C1 KIHVEXSGLLUDHS-LBAQZLPGSA-N 0.000 claims description 2
• JNSZJWMBASVFFG-NRFANRHFSA-N 2-[(3S)-3-[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-3-(1-methylpiperidin-4-yl)prop-2-enenitrile Chemical compound C1CN(C)CCC1C=C(C#N)C(=O)N1C[C@@H](N2C3=NC=NC(N)=C3C(C=3C(=CC(OC=4C(=C(F)C=CC=4)F)=CC=3)F)=N2)CCC1 JNSZJWMBASVFFG-NRFANRHFSA-N 0.000 claims description 2
• NNJAGWVFMOGWLK-DEOSSOPVSA-N 2-[(3S)-3-[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-3-[1-(diethylaminomethyl)cyclopentyl]prop-2-enenitrile Chemical compound C([C@H](CCC1)N2C3=NC=NC(N)=C3C(C=3C(=CC(OC=4C(=C(F)C=CC=4)F)=CC=3)F)=N2)N1C(=O)C(C#N)=CC1(CN(CC)CC)CCCC1 NNJAGWVFMOGWLK-DEOSSOPVSA-N 0.000 claims description 2
• JSELVWXTZQCPKA-SFHVURJKSA-N 2-[(3S)-3-[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C1=2C(N)=NC=NC=2N([C@@H]2CN(CCC2)C(=O)C(=CC2CC2)C#N)N=C1C(C(=C1)F)=CC=C1OC1=CC=CC(F)=C1F JSELVWXTZQCPKA-SFHVURJKSA-N 0.000 claims description 2
• YOEWVNKRGSFIBQ-GGYWPGCISA-N 2-[(3S)-3-[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-3-pyrrolidin-2-ylprop-2-enenitrile Chemical compound C1=2C(N)=NC=NC=2N([C@@H]2CN(CCC2)C(=O)C(=CC2NCCC2)C#N)N=C1C(C(=C1)F)=CC=C1OC1=CC=CC(F)=C1F YOEWVNKRGSFIBQ-GGYWPGCISA-N 0.000 claims description 2
• UQLGRFKOEFQXTK-QFIPXVFZSA-N 2-[(3S)-3-[4-amino-5-(2-fluoro-4-phenoxyphenyl)-6-methylpyrrolo[2,3-d]pyrimidin-7-yl]piperidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C12=C(N)N=CN=C2N([C@@H]2CN(CCC2)C(=O)C(=CC2CC2)C#N)C(C)=C1C(C(=C1)F)=CC=C1OC1=CC=CC=C1 UQLGRFKOEFQXTK-QFIPXVFZSA-N 0.000 claims description 2
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