ES2776175T3 - Pirrolo- o pirazolopirimidinas covalentes reversibles útiles para el tratamiento de cáncer y enfermedades autoinmunes - Google Patents

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Publication number

ES2776175T3

ES2776175T3 ES13731218T ES13731218T ES2776175T3 ES 2776175 T3 ES2776175 T3 ES 2776175T3 ES 13731218 T ES13731218 T ES 13731218T ES 13731218 T ES13731218 T ES 13731218T ES 2776175 T3 ES2776175 T3 ES 2776175T3

Authority

ES

Spain

Prior art keywords

amino

pyrimidin

carbonyl

pyrazolo

methyl

Prior art date

2012-06-18

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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• 206010028980 Neoplasm Diseases 0.000 title claims description 11
• 201000011510 cancer Diseases 0.000 title claims description 11
• 208000023275 Autoimmune disease Diseases 0.000 title claims description 9
• 230000002441 reversible effect Effects 0.000 title description 12
• APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 247
• -1 chloro, fluoro, cyclopropyl Chemical group 0.000 claims abstract description 166
• 239000000203 mixture Substances 0.000 claims abstract description 133
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 115
• 150000003839 salts Chemical class 0.000 claims abstract description 74
• 238000009472 formulation Methods 0.000 claims abstract description 70
• 238000009505 enteric coating Methods 0.000 claims abstract description 69
• 239000002702 enteric coating Substances 0.000 claims abstract description 69
• 238000000576 coating method Methods 0.000 claims abstract description 58
• 239000001257 hydrogen Substances 0.000 claims abstract description 53
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 53
• 239000011248 coating agent Substances 0.000 claims abstract description 52
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 48
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 42
• 239000007787 solid Substances 0.000 claims abstract description 41
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 36
• 125000001424 substituent group Chemical group 0.000 claims abstract description 28
• 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 27
• 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 23
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 22
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 21
• 230000003111 delayed effect Effects 0.000 claims abstract description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 21
• 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 20
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 19
• 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 18
• 150000004820 halides Chemical class 0.000 claims abstract description 18
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 12
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
• 125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 8
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
• LXMLVOPDJHSYST-UHFFFAOYSA-N 2-[2-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethylsulfonyl]-3-cyclopropylprop-2-enenitrile Chemical compound N1=C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)C=2C(N)=NC=NC=2N1CCS(=O)(=O)C(C#N)=CC1CC1 LXMLVOPDJHSYST-UHFFFAOYSA-N 0.000 claims abstract description 6
• NGQSBNHWNCYPJR-UHFFFAOYSA-N 2-[5-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-1,3-oxazol-2-yl]-3-cyclopropylprop-2-enenitrile Chemical compound N1=C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)C=2C(N)=NC=NC=2N1CC(O1)=CN=C1C(C#N)=CC1CC1 NGQSBNHWNCYPJR-UHFFFAOYSA-N 0.000 claims abstract description 6
• HYMDWKLQUKDBKB-UHFFFAOYSA-N N-[2-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-1-cyano-2-cyclopropyl-N-methylethenesulfonamide Chemical compound C1CC1C=C(C#N)S(=O)(=O)N(C)CCN(C1=NC=NC(N)=C11)N=C1C(C(=C1)F)=CC=C1OC1=CC=CC=C1 HYMDWKLQUKDBKB-UHFFFAOYSA-N 0.000 claims abstract description 6
• BHDOETHUPUKOPG-UHFFFAOYSA-N N-[2-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-1-cyano-2-cyclopropylethenesulfonamide Chemical compound N1=C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)C=2C(N)=NC=NC=2N1CCNS(=O)(=O)C(C#N)=CC1CC1 BHDOETHUPUKOPG-UHFFFAOYSA-N 0.000 claims abstract description 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
• GQUJDCOJPFVAOF-UHFFFAOYSA-N [1-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]-2-methylpropan-2-yl] 2-cyano-3-cyclopropylprop-2-enoate Chemical compound C1CC1C=C(C#N)C(=O)OC(C)(C)CN(C1=NC=NC(N)=C11)N=C1C(C(=C1)F)=CC=C1OC1=CC=CC=C1 GQUJDCOJPFVAOF-UHFFFAOYSA-N 0.000 claims abstract description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
• 201000010099 disease Diseases 0.000 claims description 27
• 125000004476 heterocycloamino group Chemical group 0.000 claims description 17
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
• 201000004624 Dermatitis Diseases 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 208000027866 inflammatory disease Diseases 0.000 claims description 7
• KZMQPYCXSAGLTB-HXUWFJFHSA-N 2-[(3R)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4,4-dimethylpent-2-enenitrile Chemical compound C1N(C(=O)C(C#N)=CC(C)(C)C)CCC[C@H]1N1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1 KZMQPYCXSAGLTB-HXUWFJFHSA-N 0.000 claims description 6
• 229920006318 anionic polymer Polymers 0.000 claims description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 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
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 6
• NZIQNLGMMJGSQU-QHCPKHFHSA-N 2-[(2s)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-methyl-4-morpholin-4-ylpent-2-enenitrile Chemical compound C([C@@H]1CCCN1C(=O)C(C#N)=CC(C)(C)N1CCOCC1)N(C1=NC=NC(N)=C11)N=C1C(C(=C1)F)=CC=C1OC1=CC=CC=C1 NZIQNLGMMJGSQU-QHCPKHFHSA-N 0.000 claims description 5
• 229920003174 cellulose-based polymer Polymers 0.000 claims description 5
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 5
• 229920000193 polymethacrylate Polymers 0.000 claims description 5
• 125000004486 1-methylpiperidin-3-yl group Chemical group CN1CC(CCC1)* 0.000 claims description 4
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 4
• DUOXDOVHDJDYMX-XMMPIXPASA-N 2-[(2r)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-methyl-4-piperidin-1-ylpent-2-enenitrile Chemical compound C([C@H]1CCCN1C(=O)C(C#N)=CC(C)(C)N1CCCCC1)N(C1=NC=NC(N)=C11)N=C1C(C(=C1)F)=CC=C1OC1=CC=CC=C1 DUOXDOVHDJDYMX-XMMPIXPASA-N 0.000 claims description 4
• BJBBMHJDZCVALB-XMMPIXPASA-N 2-[(2r)-2-[[4-amino-5-(4-phenoxyphenyl)pyrrolo[2,3-d]pyrimidin-7-yl]methyl]pyrrolidine-1-carbonyl]-4-(dimethylamino)-4-methylpent-2-enenitrile Chemical compound CN(C)C(C)(C)C=C(C#N)C(=O)N1CCC[C@@H]1CN1C2=NC=NC(N)=C2C(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=C1 BJBBMHJDZCVALB-XMMPIXPASA-N 0.000 claims description 4
• DUOXDOVHDJDYMX-DEOSSOPVSA-N 2-[(2s)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-methyl-4-piperidin-1-ylpent-2-enenitrile Chemical compound C([C@@H]1CCCN1C(=O)C(C#N)=CC(C)(C)N1CCCCC1)N(C1=NC=NC(N)=C11)N=C1C(C(=C1)F)=CC=C1OC1=CC=CC=C1 DUOXDOVHDJDYMX-DEOSSOPVSA-N 0.000 claims description 4
• BJBBMHJDZCVALB-DEOSSOPVSA-N 2-[(2s)-2-[[4-amino-5-(4-phenoxyphenyl)pyrrolo[2,3-d]pyrimidin-7-yl]methyl]pyrrolidine-1-carbonyl]-4-(dimethylamino)-4-methylpent-2-enenitrile Chemical compound CN(C)C(C)(C)C=C(C#N)C(=O)N1CCC[C@H]1CN1C2=NC=NC(N)=C2C(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=C1 BJBBMHJDZCVALB-DEOSSOPVSA-N 0.000 claims description 4
• WNLTXZCOYCXQHU-UHFFFAOYSA-N 2-[2-[[4-amino-6-methyl-5-(4-phenoxyphenyl)pyrrolo[2,3-d]pyrimidin-7-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C12=C(N)N=CN=C2N(CC2N(CCC2)C(=O)C(=CC2CC2)C#N)C(C)=C1C(C=C1)=CC=C1OC1=CC=CC=C1 WNLTXZCOYCXQHU-UHFFFAOYSA-N 0.000 claims description 4
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 4
• IDJHMBKQEPOZBR-LJQANCHMSA-N 4-amino-2-[(2r)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-methylpent-2-enenitrile Chemical compound CC(C)(N)C=C(C#N)C(=O)N1CCC[C@@H]1CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1 IDJHMBKQEPOZBR-LJQANCHMSA-N 0.000 claims description 4
• IDJHMBKQEPOZBR-IBGZPJMESA-N 4-amino-2-[(2s)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-methylpent-2-enenitrile Chemical compound CC(C)(N)C=C(C#N)C(=O)N1CCC[C@H]1CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1 IDJHMBKQEPOZBR-IBGZPJMESA-N 0.000 claims description 4
• 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
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• 206010039710 Scleroderma Diseases 0.000 claims description 4
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• PRRNZFGBGPELQP-HXUWFJFHSA-N 2-[(2R)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-[1-(methylamino)cyclopropyl]prop-2-enenitrile Chemical compound N1([C@H](CCC1)CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1)C(=O)C(C#N)=CC1(NC)CC1 PRRNZFGBGPELQP-HXUWFJFHSA-N 0.000 claims description 2
• HAPRCXSAULDFHG-JOCHJYFZSA-N 2-[(2R)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-[1-(propan-2-ylamino)cyclopropyl]prop-2-enenitrile Chemical compound N1([C@H](CCC1)CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1)C(=O)C(C#N)=CC1(NC(C)C)CC1 HAPRCXSAULDFHG-JOCHJYFZSA-N 0.000 claims description 2
• VILCMHIZGWATBW-XMMPIXPASA-N 2-[(2R)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-[1-[(dimethylamino)methyl]cyclopentyl]prop-2-enenitrile Chemical compound N1([C@H](CCC1)CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1)C(=O)C(C#N)=CC1(CN(C)C)CCCC1 VILCMHIZGWATBW-XMMPIXPASA-N 0.000 claims description 2
• QLFDACIJUUSZFJ-LWMIZPGFSA-N 2-[(2R)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-piperidin-3-ylprop-2-enenitrile Chemical compound C([C@@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C=CC=CC=4)=CC=3)F)=N2)N)CCN1C(=O)C(C#N)=CC1CCCNC1 QLFDACIJUUSZFJ-LWMIZPGFSA-N 0.000 claims description 2
• VXMSFRPFOIGCQU-JOCHJYFZSA-N 2-[(2R)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-piperidin-4-ylprop-2-enenitrile Chemical compound C([C@@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C=CC=CC=4)=CC=3)F)=N2)N)CCN1C(=O)C(C#N)=CC1CCNCC1 VXMSFRPFOIGCQU-JOCHJYFZSA-N 0.000 claims description 2
• DJFYWYMNPNZOCD-BPGUCPLFSA-N 2-[(2R)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-pyrrolidin-2-ylprop-2-enenitrile Chemical compound C([C@@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C=CC=CC=4)=CC=3)F)=N2)N)CCN1C(=O)C(C#N)=CC1CCCN1 DJFYWYMNPNZOCD-BPGUCPLFSA-N 0.000 claims description 2
• BESYWHDYQFWATR-HXUWFJFHSA-N 2-[(2R)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-methylpent-2-enenitrile Chemical compound CC(C)C=C(C#N)C(=O)N1CCC[C@@H]1CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1 BESYWHDYQFWATR-HXUWFJFHSA-N 0.000 claims description 2
• YQBZUMLDZJOWCG-OAQYLSRUSA-N 2-[(2R)-2-[[4-amino-3-(3-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@@H]1CN2C=3N=CN=C(C=3C(C=3C=C(F)C(OC=4C=CC=CC=4)=CC=3)=N2)N)CCN1C(=O)C(C#N)=CC1CC1 YQBZUMLDZJOWCG-OAQYLSRUSA-N 0.000 claims description 2
• UDMBWKPTVSCOHR-HXUWFJFHSA-N 2-[(2R)-2-[[4-amino-3-[2-fluoro-4-(3-fluorophenoxy)phenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C=C(F)C=CC=4)=CC=3)F)=N2)N)CCN1C(=O)C(C#N)=CC1CC1 UDMBWKPTVSCOHR-HXUWFJFHSA-N 0.000 claims description 2
• LHDIENGTWJSAQR-OAQYLSRUSA-N 2-[(2R)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-(1-methylpiperidin-4-yl)prop-2-enenitrile Chemical compound C1CN(C)CCC1C=C(C#N)C(=O)N1[C@@H](CN2C3=NC=NC(N)=C3C(C=3C(=CC(OC=4C(=C(F)C=CC=4)F)=CC=3)F)=N2)CCC1 LHDIENGTWJSAQR-OAQYLSRUSA-N 0.000 claims description 2
• TUEXBPMUBUXHDB-HXUWFJFHSA-N 2-[(2R)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-(oxan-4-yl)prop-2-enenitrile Chemical compound C([C@@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C(=C(F)C=CC=4)F)=CC=3)F)=N2)N)CCN1C(=O)C(C#N)=CC1CCOCC1 TUEXBPMUBUXHDB-HXUWFJFHSA-N 0.000 claims description 2
• HZSKWVTYHGCROU-XMMPIXPASA-N 2-[(2R)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-[1-(diethylaminomethyl)cyclopentyl]prop-2-enenitrile Chemical compound N1([C@H](CCC1)CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C(=C(F)C=CC=3)F)=CC=2)F)=N1)C(=O)C(C#N)=CC1(CN(CC)CC)CCCC1 HZSKWVTYHGCROU-XMMPIXPASA-N 0.000 claims description 2
• ALWCTUAHGPPJIV-LJQANCHMSA-N 2-[(2R)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-[1-(ethylamino)cyclopropyl]prop-2-enenitrile Chemical compound N1([C@H](CCC1)CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C(=C(F)C=CC=3)F)=CC=2)F)=N1)C(=O)C(C#N)=CC1(NCC)CC1 ALWCTUAHGPPJIV-LJQANCHMSA-N 0.000 claims description 2
• RYLUGFKKSWCGMS-GOSISDBHSA-N 2-[(2R)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-[1-(methylamino)cyclopropyl]prop-2-enenitrile Chemical compound N1([C@H](CCC1)CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C(=C(F)C=CC=3)F)=CC=2)F)=N1)C(=O)C(C#N)=CC1(NC)CC1 RYLUGFKKSWCGMS-GOSISDBHSA-N 0.000 claims description 2
• KAAXGGACDPUIMN-HXUWFJFHSA-N 2-[(2R)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-[1-(propan-2-ylamino)cyclopropyl]prop-2-enenitrile Chemical compound N1([C@H](CCC1)CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C(=C(F)C=CC=3)F)=CC=2)F)=N1)C(=O)C(C#N)=CC1(NC(C)C)CC1 KAAXGGACDPUIMN-HXUWFJFHSA-N 0.000 claims description 2
• MGSAFDVGUFCXNE-HXUWFJFHSA-N 2-[(2R)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-piperidin-4-ylprop-2-enenitrile Chemical compound C([C@@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C(=C(F)C=CC=4)F)=CC=3)F)=N2)N)CCN1C(=O)C(C#N)=CC1CCNCC1 MGSAFDVGUFCXNE-HXUWFJFHSA-N 0.000 claims description 2
• ALECKWSRFHPUGK-MUMRKEEXSA-N 2-[(2R)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-pyrrolidin-2-ylprop-2-enenitrile Chemical compound C([C@@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C(=C(F)C=CC=4)F)=CC=3)F)=N2)N)CCN1C(=O)C(C#N)=CC1CCCN1 ALECKWSRFHPUGK-MUMRKEEXSA-N 0.000 claims description 2
• JNAYDXFMMRTTAX-OAQYLSRUSA-N 2-[(2R)-2-[[4-amino-3-[4-(2,5-difluorophenoxy)phenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@@H]1CN2C=3N=CN=C(C=3C(C=3C=CC(OC=4C(=CC=C(F)C=4)F)=CC=3)=N2)N)CCN1C(=O)C(C#N)=CC1CC1 JNAYDXFMMRTTAX-OAQYLSRUSA-N 0.000 claims description 2
• WBPYSPBQYMHIEC-GOSISDBHSA-N 2-[(2R)-2-[[4-amino-3-[4-(2,6-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C(=CC=CC=4F)F)=CC=3)F)=N2)N)CCN1C(=O)C(C#N)=CC1CC1 WBPYSPBQYMHIEC-GOSISDBHSA-N 0.000 claims description 2
• CHUVQXPESSHLOM-JOCHJYFZSA-N 2-[(2R)-2-[[4-amino-5-(2-fluoro-4-phenoxyphenyl)-6-methylpyrrolo[2,3-d]pyrimidin-7-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C12=C(N)N=CN=C2N(C[C@@H]2N(CCC2)C(=O)C(=CC2CC2)C#N)C(C)=C1C(C(=C1)F)=CC=C1OC1=CC=CC=C1 CHUVQXPESSHLOM-JOCHJYFZSA-N 0.000 claims description 2
• XGIYERXTGLEFID-OAQYLSRUSA-N 2-[(2R)-2-[[4-amino-5-(2-fluoro-4-phenoxyphenyl)pyrrolo[2,3-d]pyrimidin-7-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C=CC=CC=4)=CC=3)F)=C2)N)CCN1C(=O)C(C#N)=CC1CC1 XGIYERXTGLEFID-OAQYLSRUSA-N 0.000 claims description 2
• XLALLISGANRDDC-HSZRJFAPSA-N 2-[(2R)-2-[[4-amino-5-(4-phenoxyphenyl)pyrrolo[2,3-d]pyrimidin-7-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@@H]1CN2C=3N=CN=C(C=3C(C=3C=CC(OC=4C=CC=CC=4)=CC=3)=C2)N)CCN1C(=O)C(C#N)=CC1CC1 XLALLISGANRDDC-HSZRJFAPSA-N 0.000 claims description 2
• UETBUVYLRUIFIP-OAQYLSRUSA-N 2-[(2R)-2-[[4-amino-5-[4-(2,3-difluorophenoxy)phenyl]pyrrolo[2,3-d]pyrimidin-7-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@@H]1CN2C=3N=CN=C(C=3C(C=3C=CC(OC=4C(=C(F)C=CC=4)F)=CC=3)=C2)N)CCN1C(=O)C(C#N)=CC1CC1 UETBUVYLRUIFIP-OAQYLSRUSA-N 0.000 claims description 2
• SOHZZOWWQLHMBF-XMMPIXPASA-N 2-[(2R)-2-[[4-amino-5-[4-(3,5-difluorophenoxy)phenyl]-6-methylpyrrolo[2,3-d]pyrimidin-7-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C12=C(N)N=CN=C2N(C[C@@H]2N(CCC2)C(=O)C(=CC2CC2)C#N)C(C)=C1C(C=C1)=CC=C1OC1=CC(F)=CC(F)=C1 SOHZZOWWQLHMBF-XMMPIXPASA-N 0.000 claims description 2
• FQEGACSJFGTHBB-HSZRJFAPSA-N 2-[(2R)-2-[[4-amino-5-[4-(3,5-difluorophenoxy)phenyl]pyrrolo[2,3-d]pyrimidin-7-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@@H]1CN2C=3N=CN=C(C=3C(C=3C=CC(OC=4C=C(F)C=C(F)C=4)=CC=3)=C2)N)CCN1C(=O)C(C#N)=CC1CC1 FQEGACSJFGTHBB-HSZRJFAPSA-N 0.000 claims description 2
• SLYGDRWTJRPLPE-FQEVSTJZSA-N 2-[(2S)-2-[[4-amino-3-(2-chloro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C=CC=CC=4)=CC=3)Cl)=N2)N)CCN1C(=O)C(C#N)=CC1CC1 SLYGDRWTJRPLPE-FQEVSTJZSA-N 0.000 claims description 2
• QWENXYFISYOVAE-IBGZPJMESA-N 2-[(2S)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-4,4-difluoropyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C=CC=CC=4)=CC=3)F)=N2)N)C(F)(F)CN1C(=O)C(C#N)=CC1CC1 QWENXYFISYOVAE-IBGZPJMESA-N 0.000 claims description 2
• OTEPSQCCLGCTHS-QFIPXVFZSA-N 2-[(2S)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-(oxan-4-yl)prop-2-enenitrile Chemical compound C([C@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C=CC=CC=4)=CC=3)F)=N2)N)CCN1C(=O)C(C#N)=CC1CCOCC1 OTEPSQCCLGCTHS-QFIPXVFZSA-N 0.000 claims description 2
• VWKLJHJZMCQRTA-NRFANRHFSA-N 2-[(2S)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-[1-(ethylamino)cyclopropyl]prop-2-enenitrile Chemical compound N1([C@@H](CCC1)CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1)C(=O)C(C#N)=CC1(NCC)CC1 VWKLJHJZMCQRTA-NRFANRHFSA-N 0.000 claims description 2
• PRRNZFGBGPELQP-FQEVSTJZSA-N 2-[(2S)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-[1-(methylamino)cyclopropyl]prop-2-enenitrile Chemical compound N1([C@@H](CCC1)CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1)C(=O)C(C#N)=CC1(NC)CC1 PRRNZFGBGPELQP-FQEVSTJZSA-N 0.000 claims description 2
• HAPRCXSAULDFHG-QFIPXVFZSA-N 2-[(2S)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-[1-(propan-2-ylamino)cyclopropyl]prop-2-enenitrile Chemical compound N1([C@@H](CCC1)CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1)C(=O)C(C#N)=CC1(NC(C)C)CC1 HAPRCXSAULDFHG-QFIPXVFZSA-N 0.000 claims description 2
• VILCMHIZGWATBW-DEOSSOPVSA-N 2-[(2S)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-[1-[(dimethylamino)methyl]cyclopentyl]prop-2-enenitrile Chemical compound N1([C@@H](CCC1)CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1)C(=O)C(C#N)=CC1(CN(C)C)CCCC1 VILCMHIZGWATBW-DEOSSOPVSA-N 0.000 claims description 2
• QLFDACIJUUSZFJ-IAXKEJLGSA-N 2-[(2S)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-piperidin-3-ylprop-2-enenitrile Chemical compound C([C@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C=CC=CC=4)=CC=3)F)=N2)N)CCN1C(=O)C(C#N)=CC1CCCNC1 QLFDACIJUUSZFJ-IAXKEJLGSA-N 0.000 claims description 2
• VXMSFRPFOIGCQU-QFIPXVFZSA-N 2-[(2S)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-piperidin-4-ylprop-2-enenitrile Chemical compound C([C@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C=CC=CC=4)=CC=3)F)=N2)N)CCN1C(=O)C(C#N)=CC1CCNCC1 VXMSFRPFOIGCQU-QFIPXVFZSA-N 0.000 claims description 2
• DJFYWYMNPNZOCD-LBAQZLPGSA-N 2-[(2S)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-pyrrolidin-2-ylprop-2-enenitrile Chemical compound C([C@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C=CC=CC=4)=CC=3)F)=N2)N)CCN1C(=O)C(C#N)=CC1CCCN1 DJFYWYMNPNZOCD-LBAQZLPGSA-N 0.000 claims description 2
• NDLULCUHFGKSRR-FQEVSTJZSA-N 2-[(2S)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4,4-dimethylpent-2-enenitrile Chemical compound CC(C)(C)C=C(C#N)C(=O)N1CCC[C@H]1CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1 NDLULCUHFGKSRR-FQEVSTJZSA-N 0.000 claims description 2
• BESYWHDYQFWATR-FQEVSTJZSA-N 2-[(2S)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-methylpent-2-enenitrile Chemical compound CC(C)C=C(C#N)C(=O)N1CCC[C@H]1CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1 BESYWHDYQFWATR-FQEVSTJZSA-N 0.000 claims description 2
• FFNPAVVGSXGKFD-QFIPXVFZSA-N 2-[(2S)-2-[[4-amino-3-(2-methyl-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C=1C=C(C=2C3=C(N)N=CN=C3N(C[C@H]3N(CCC3)C(=O)C(=CC3CC3)C#N)N=2)C(C)=CC=1OC1=CC=CC=C1 FFNPAVVGSXGKFD-QFIPXVFZSA-N 0.000 claims description 2
• YQBZUMLDZJOWCG-NRFANRHFSA-N 2-[(2S)-2-[[4-amino-3-(3-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@H]1CN2C=3N=CN=C(C=3C(C=3C=C(F)C(OC=4C=CC=CC=4)=CC=3)=N2)N)CCN1C(=O)C(C#N)=CC1CC1 YQBZUMLDZJOWCG-NRFANRHFSA-N 0.000 claims description 2
• LHDIENGTWJSAQR-NRFANRHFSA-N 2-[(2S)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-(1-methylpiperidin-4-yl)prop-2-enenitrile Chemical compound C1CN(C)CCC1C=C(C#N)C(=O)N1[C@H](CN2C3=NC=NC(N)=C3C(C=3C(=CC(OC=4C(=C(F)C=CC=4)F)=CC=3)F)=N2)CCC1 LHDIENGTWJSAQR-NRFANRHFSA-N 0.000 claims description 2
• TUEXBPMUBUXHDB-FQEVSTJZSA-N 2-[(2S)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-(oxan-4-yl)prop-2-enenitrile Chemical compound C([C@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C(=C(F)C=CC=4)F)=CC=3)F)=N2)N)CCN1C(=O)C(C#N)=CC1CCOCC1 TUEXBPMUBUXHDB-FQEVSTJZSA-N 0.000 claims description 2
• HZSKWVTYHGCROU-DEOSSOPVSA-N 2-[(2S)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-[1-(diethylaminomethyl)cyclopentyl]prop-2-enenitrile Chemical compound N1([C@@H](CCC1)CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C(=C(F)C=CC=3)F)=CC=2)F)=N1)C(=O)C(C#N)=CC1(CN(CC)CC)CCCC1 HZSKWVTYHGCROU-DEOSSOPVSA-N 0.000 claims description 2
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• RPLMHDNWGHMMSD-IJHRGXPZSA-N 2-[(2S)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-piperidin-3-ylprop-2-enenitrile Chemical compound C([C@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C(=C(F)C=CC=4)F)=CC=3)F)=N2)N)CCN1C(=O)C(C#N)=CC1CCCNC1 RPLMHDNWGHMMSD-IJHRGXPZSA-N 0.000 claims description 2
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• YIDJEMDQRXSZRP-NRFANRHFSA-N 2-[(2S)-2-[[4-amino-3-[4-(2-fluorophenoxy)phenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@H]1CN2C=3N=CN=C(C=3C(C=3C=CC(OC=4C(=CC=CC=4)F)=CC=3)=N2)N)CCN1C(=O)C(C#N)=CC1CC1 YIDJEMDQRXSZRP-NRFANRHFSA-N 0.000 claims description 2
• DIRBFYTXWMNIIA-FQEVSTJZSA-N 2-[(2S)-2-[[4-amino-3-[4-(3,5-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C=C(F)C=C(F)C=4)=CC=3)F)=N2)N)CCN1C(=O)C(C#N)=CC1CC1 DIRBFYTXWMNIIA-FQEVSTJZSA-N 0.000 claims description 2
• HWXKECVQNNJJPE-QFIPXVFZSA-N 2-[(2S)-2-[[4-amino-3-[4-(3,5-difluorophenoxy)phenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@H]1CN2C=3N=CN=C(C=3C(C=3C=CC(OC=4C=C(F)C=C(F)C=4)=CC=3)=N2)N)CCN1C(=O)C(C#N)=CC1CC1 HWXKECVQNNJJPE-QFIPXVFZSA-N 0.000 claims description 2
• ODTVIGFDPJLHPJ-QFIPXVFZSA-N 2-[(2S)-2-[[4-amino-3-[4-(3-fluorophenoxy)phenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@H]1CN2C=3N=CN=C(C=3C(C=3C=CC(OC=4C=C(F)C=CC=4)=CC=3)=N2)N)CCN1C(=O)C(C#N)=CC1CC1 ODTVIGFDPJLHPJ-QFIPXVFZSA-N 0.000 claims description 2
• CHUVQXPESSHLOM-QFIPXVFZSA-N 2-[(2S)-2-[[4-amino-5-(2-fluoro-4-phenoxyphenyl)-6-methylpyrrolo[2,3-d]pyrimidin-7-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C12=C(N)N=CN=C2N(C[C@H]2N(CCC2)C(=O)C(=CC2CC2)C#N)C(C)=C1C(C(=C1)F)=CC=C1OC1=CC=CC=C1 CHUVQXPESSHLOM-QFIPXVFZSA-N 0.000 claims description 2
• XGIYERXTGLEFID-NRFANRHFSA-N 2-[(2S)-2-[[4-amino-5-(2-fluoro-4-phenoxyphenyl)pyrrolo[2,3-d]pyrimidin-7-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C=CC=CC=4)=CC=3)F)=C2)N)CCN1C(=O)C(C#N)=CC1CC1 XGIYERXTGLEFID-NRFANRHFSA-N 0.000 claims description 2
• UETBUVYLRUIFIP-NRFANRHFSA-N 2-[(2S)-2-[[4-amino-5-[4-(2,3-difluorophenoxy)phenyl]pyrrolo[2,3-d]pyrimidin-7-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@H]1CN2C=3N=CN=C(C=3C(C=3C=CC(OC=4C(=C(F)C=CC=4)F)=CC=3)=C2)N)CCN1C(=O)C(C#N)=CC1CC1 UETBUVYLRUIFIP-NRFANRHFSA-N 0.000 claims description 2
• SOHZZOWWQLHMBF-DEOSSOPVSA-N 2-[(2S)-2-[[4-amino-5-[4-(3,5-difluorophenoxy)phenyl]-6-methylpyrrolo[2,3-d]pyrimidin-7-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C12=C(N)N=CN=C2N(C[C@H]2N(CCC2)C(=O)C(=CC2CC2)C#N)C(C)=C1C(C=C1)=CC=C1OC1=CC(F)=CC(F)=C1 SOHZZOWWQLHMBF-DEOSSOPVSA-N 0.000 claims description 2
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• CBXYWKLJGUCHPH-LJQANCHMSA-N 2-[(2r)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-4,4-difluoropyrrolidine-1-carbonyl]-4-methylpent-2-enenitrile Chemical compound CC(C)C=C(C#N)C(=O)N1CC(F)(F)C[C@@H]1CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1 CBXYWKLJGUCHPH-LJQANCHMSA-N 0.000 claims description 2
• DJFYWYMNPNZOCD-LEWJYISDSA-N 2-[(2r)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-[(2s)-pyrrolidin-2-yl]prop-2-enenitrile Chemical compound C([C@@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C=CC=CC=4)=CC=3)F)=N2)N)CCN1C(=O)C(C#N)=C[C@@H]1CCCN1 DJFYWYMNPNZOCD-LEWJYISDSA-N 0.000 claims description 2
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• NDLULCUHFGKSRR-HXUWFJFHSA-N 2-[(2r)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4,4-dimethylpent-2-enenitrile Chemical compound CC(C)(C)C=C(C#N)C(=O)N1CCC[C@@H]1CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1 NDLULCUHFGKSRR-HXUWFJFHSA-N 0.000 claims description 2
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• PVBDQCRWZPYKOP-OAQYLSRUSA-N 2-[(2r)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-ethoxy-4-methylpent-2-enenitrile Chemical compound CCOC(C)(C)C=C(C#N)C(=O)N1CCC[C@@H]1CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1 PVBDQCRWZPYKOP-OAQYLSRUSA-N 0.000 claims description 2
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• CDQOCVPNUKEIQE-JOCHJYFZSA-N 2-[(2r)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-methyl-4-(propan-2-ylamino)pent-2-enenitrile Chemical compound CC(C)NC(C)(C)C=C(C#N)C(=O)N1CCC[C@@H]1CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1 CDQOCVPNUKEIQE-JOCHJYFZSA-N 0.000 claims description 2
• DPEOIHCRFGFQBA-JOCHJYFZSA-N 2-[(2r)-2-[[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4,4-dimethylpent-2-enenitrile Chemical compound CC(C)(C)C=C(C#N)C(=O)N1CCC[C@@H]1CN1C2=NC=NC(N)=C2C(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 DPEOIHCRFGFQBA-JOCHJYFZSA-N 0.000 claims description 2
• QJBVYURBZSGGMS-HXUWFJFHSA-N 2-[(2r)-2-[[4-amino-3-[2-fluoro-4-(3-fluorophenoxy)phenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-methylpent-2-enenitrile Chemical compound CC(C)C=C(C#N)C(=O)N1CCC[C@@H]1CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=C(F)C=CC=3)=CC=2)F)=N1 QJBVYURBZSGGMS-HXUWFJFHSA-N 0.000 claims description 2
• ZSLSVCCZNWZIRV-GOSISDBHSA-N 2-[(2r)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C(=C(F)C=CC=4)F)=CC=3)F)=N2)N)CCN1C(=O)C(C#N)=CC1CC1 ZSLSVCCZNWZIRV-GOSISDBHSA-N 0.000 claims description 2
• IMGDSBFPBQIDLG-GOSISDBHSA-N 2-[(2r)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4,4-dimethylpent-2-enenitrile Chemical compound CC(C)(C)C=C(C#N)C(=O)N1CCC[C@@H]1CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C(=C(F)C=CC=3)F)=CC=2)F)=N1 IMGDSBFPBQIDLG-GOSISDBHSA-N 0.000 claims description 2
• RZJWGRSPUSIWDU-HXUWFJFHSA-N 2-[(2r)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-(2-methoxyethylamino)-4-methylpent-2-enenitrile Chemical compound COCCNC(C)(C)C=C(C#N)C(=O)N1CCC[C@@H]1CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C(=C(F)C=CC=3)F)=CC=2)F)=N1 RZJWGRSPUSIWDU-HXUWFJFHSA-N 0.000 claims description 2
• MZGCGLBHUPHJPP-HXUWFJFHSA-N 2-[(2r)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-(cyclopropylamino)-4-methylpent-2-enenitrile Chemical compound N1([C@H](CCC1)CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C(=C(F)C=CC=3)F)=CC=2)F)=N1)C(=O)C(C#N)=CC(C)(C)NC1CC1 MZGCGLBHUPHJPP-HXUWFJFHSA-N 0.000 claims description 2
• ANEDRESITAZMQR-LJQANCHMSA-N 2-[(2r)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-(dimethylamino)-4-methylpent-2-enenitrile Chemical compound CN(C)C(C)(C)C=C(C#N)C(=O)N1CCC[C@@H]1CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C(=C(F)C=CC=3)F)=CC=2)F)=N1 ANEDRESITAZMQR-LJQANCHMSA-N 0.000 claims description 2
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• WBIAKBCGGASHPE-AREMUKBSSA-N 2-[(2r)-2-[[4-amino-5-(4-phenoxyphenyl)pyrrolo[2,3-d]pyrimidin-7-yl]methyl]pyrrolidine-1-carbonyl]-4-methyl-4-morpholin-4-ylpent-2-enenitrile Chemical compound C([C@H]1CCCN1C(=O)C(C#N)=CC(C)(C)N1CCOCC1)N(C1=NC=NC(N)=C11)C=C1C(C=C1)=CC=C1OC1=CC=CC=C1 WBIAKBCGGASHPE-AREMUKBSSA-N 0.000 claims description 2
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• UDMBWKPTVSCOHR-FQEVSTJZSA-N 2-[(2s)-2-[[4-amino-3-[2-fluoro-4-(3-fluorophenoxy)phenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C=C(F)C=CC=4)=CC=3)F)=N2)N)CCN1C(=O)C(C#N)=CC1CC1 UDMBWKPTVSCOHR-FQEVSTJZSA-N 0.000 claims description 2
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• ZSLSVCCZNWZIRV-SFHVURJKSA-N 2-[(2s)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-3-cyclopropylprop-2-enenitrile Chemical compound C([C@H]1CN2C=3N=CN=C(C=3C(C=3C(=CC(OC=4C(=C(F)C=CC=4)F)=CC=3)F)=N2)N)CCN1C(=O)C(C#N)=CC1CC1 ZSLSVCCZNWZIRV-SFHVURJKSA-N 0.000 claims description 2
• IMGDSBFPBQIDLG-SFHVURJKSA-N 2-[(2s)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4,4-dimethylpent-2-enenitrile Chemical compound CC(C)(C)C=C(C#N)C(=O)N1CCC[C@H]1CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C(=C(F)C=CC=3)F)=CC=2)F)=N1 IMGDSBFPBQIDLG-SFHVURJKSA-N 0.000 claims description 2
• RZJWGRSPUSIWDU-FQEVSTJZSA-N 2-[(2s)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-(2-methoxyethylamino)-4-methylpent-2-enenitrile Chemical compound COCCNC(C)(C)C=C(C#N)C(=O)N1CCC[C@H]1CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C(=C(F)C=CC=3)F)=CC=2)F)=N1 RZJWGRSPUSIWDU-FQEVSTJZSA-N 0.000 claims description 2
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• BKCICBNLQFMNEZ-IBGZPJMESA-N 2-[(2s)-2-[[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-ethoxy-4-methylpent-2-enenitrile Chemical compound CCOC(C)(C)C=C(C#N)C(=O)N1CCC[C@H]1CN1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C(=C(F)C=CC=3)F)=CC=2)F)=N1 BKCICBNLQFMNEZ-IBGZPJMESA-N 0.000 claims description 2
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• JCDAJUALOINUEJ-IJHRGXPZSA-N 2-[(3S)-3-[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]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(F)=C1F JCDAJUALOINUEJ-IJHRGXPZSA-N 0.000 claims description 2
• GWSGAXGNGOQTFG-FQEVSTJZSA-N 2-[(3S)-3-[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-3-piperidin-4-ylprop-2-enenitrile Chemical compound C1=2C(N)=NC=NC=2N([C@@H]2CN(CCC2)C(=O)C(=CC2CCNCC2)C#N)N=C1C(C(=C1)F)=CC=C1OC1=CC=CC(F)=C1F GWSGAXGNGOQTFG-FQEVSTJZSA-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
• HRTOJHBVIFYGJC-DEOSSOPVSA-N 2-[(3S)-3-[4-amino-5-[4-(3,5-difluorophenoxy)phenyl]-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)=CC=C1OC1=CC(F)=CC(F)=C1 HRTOJHBVIFYGJC-DEOSSOPVSA-N 0.000 claims description 2
• UKURDKADUIBPHB-QHCPKHFHSA-N 2-[(3S)-3-[4-amino-5-[4-(3,5-difluorophenoxy)phenyl]pyrrolo[2,3-d]pyrimidin-7-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)C=C1C(C=C1)=CC=C1OC1=CC(F)=CC(F)=C1 UKURDKADUIBPHB-QHCPKHFHSA-N 0.000 claims description 2
• YVXFHBBAHIDQJL-DEOSSOPVSA-N 2-[(3S)-3-[4-amino-6-methyl-5-(4-phenoxyphenyl)pyrrolo[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)=CC=C1OC1=CC=CC=C1 YVXFHBBAHIDQJL-DEOSSOPVSA-N 0.000 claims description 2
• HDRKIVDDSOTVRP-HSZRJFAPSA-N 2-[(3r)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)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=CC=CC=4)=CC=3)F)=N2)CCC1 HDRKIVDDSOTVRP-HSZRJFAPSA-N 0.000 claims description 2
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• OYEWCPLOZQWRTA-JOCHJYFZSA-N 2-[(3r)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-(cyclopropylamino)-4-methylpent-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)=CC(C)(C)NC1CC1 OYEWCPLOZQWRTA-JOCHJYFZSA-N 0.000 claims description 2
• MTMFUKIPDNCURW-OAQYLSRUSA-N 2-[(3r)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-(ethylamino)-4-methylpent-2-enenitrile Chemical compound C1N(C(=O)C(C#N)=CC(C)(C)NCC)CCC[C@H]1N1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1 MTMFUKIPDNCURW-OAQYLSRUSA-N 0.000 claims description 2
• STNWYIXKAQCFQK-HXUWFJFHSA-N 2-[(3r)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-(methylamino)pent-2-enenitrile Chemical compound C1N(C(=O)C(C#N)=CC(C)(C)NC)CCC[C@H]1N1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1 STNWYIXKAQCFQK-HXUWFJFHSA-N 0.000 claims description 2
• IDUOQDBNMAPXQQ-JOCHJYFZSA-N 2-[(3r)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-(propan-2-ylamino)pent-2-enenitrile Chemical compound C1N(C(=O)C(C#N)=CC(C)(C)NC(C)C)CCC[C@H]1N1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1 IDUOQDBNMAPXQQ-JOCHJYFZSA-N 0.000 claims description 2
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• BMHNUHSSZQGNFZ-HXUWFJFHSA-N 2-[(3r)-3-[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-(2-methoxyethylamino)-4-methylpent-2-enenitrile Chemical compound C1N(C(=O)C(C#N)=CC(C)(C)NCCOC)CCC[C@H]1N1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C(=C(F)C=CC=3)F)=CC=2)F)=N1 BMHNUHSSZQGNFZ-HXUWFJFHSA-N 0.000 claims description 2
• SOECMCJOWVYWNB-HXUWFJFHSA-N 2-[(3r)-3-[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-(cyclopropylamino)-4-methylpent-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)=CC(C)(C)NC1CC1 SOECMCJOWVYWNB-HXUWFJFHSA-N 0.000 claims description 2
• SQQLZKRKYFKTLJ-LJQANCHMSA-N 2-[(3r)-3-[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-(ethylamino)-4-methylpent-2-enenitrile Chemical compound C1N(C(=O)C(C#N)=CC(C)(C)NCC)CCC[C@H]1N1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C(=C(F)C=CC=3)F)=CC=2)F)=N1 SQQLZKRKYFKTLJ-LJQANCHMSA-N 0.000 claims description 2
• ZGHDUMGETQJRHI-GOSISDBHSA-N 2-[(3r)-3-[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-(methylamino)pent-2-enenitrile Chemical compound C1N(C(=O)C(C#N)=CC(C)(C)NC)CCC[C@H]1N1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C(=C(F)C=CC=3)F)=CC=2)F)=N1 ZGHDUMGETQJRHI-GOSISDBHSA-N 0.000 claims description 2
• GUWMWABHJKWLKX-HXUWFJFHSA-N 2-[(3r)-3-[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-(propan-2-ylamino)pent-2-enenitrile Chemical compound C1N(C(=O)C(C#N)=CC(C)(C)NC(C)C)CCC[C@H]1N1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C(=C(F)C=CC=3)F)=CC=2)F)=N1 GUWMWABHJKWLKX-HXUWFJFHSA-N 0.000 claims description 2
• NMPVOGJLOPRRNR-OAQYLSRUSA-N 2-[(3r)-3-[4-amino-3-[4-(2,3-difluorophenoxy)-2-fluorophenyl]pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-morpholin-4-ylpent-2-enenitrile Chemical compound C12=C(N)N=CN=C2N([C@@H]2CCCN(C2)C(=O)C(C#N)=CC(C)(C)N2CCOCC2)N=C1C(C(=C1)F)=CC=C1OC1=CC=CC(F)=C1F NMPVOGJLOPRRNR-OAQYLSRUSA-N 0.000 claims description 2
• HDRKIVDDSOTVRP-QHCPKHFHSA-N 2-[(3s)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)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=CC=CC=4)=CC=3)F)=N2)CCC1 HDRKIVDDSOTVRP-QHCPKHFHSA-N 0.000 claims description 2
• KZMQPYCXSAGLTB-FQEVSTJZSA-N 2-[(3s)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4,4-dimethylpent-2-enenitrile Chemical compound C1N(C(=O)C(C#N)=CC(C)(C)C)CCC[C@@H]1N1C2=NC=NC(N)=C2C(C=2C(=CC(OC=3C=CC=CC=3)=CC=2)F)=N1 KZMQPYCXSAGLTB-FQEVSTJZSA-N 0.000 claims description 2
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