JP2015527401A5 - - Google Patents
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- JP2015527401A5 JP2015527401A5 JP2015531259A JP2015531259A JP2015527401A5 JP 2015527401 A5 JP2015527401 A5 JP 2015527401A5 JP 2015531259 A JP2015531259 A JP 2015531259A JP 2015531259 A JP2015531259 A JP 2015531259A JP 2015527401 A5 JP2015527401 A5 JP 2015527401A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- pyrazolo
- fluoro
- pyrimidin
- enenitrile
- Prior art date
- 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.)
- Granted
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- -1 Oxetane-3-yl Chemical group 0.000 claims 54
- 150000001875 compounds Chemical class 0.000 claims 48
- 239000008194 pharmaceutical composition Substances 0.000 claims 31
- 150000003839 salts Chemical class 0.000 claims 29
- 239000000203 mixture Substances 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 8
- 125000001188 haloalkyl group Chemical group 0.000 claims 8
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims 8
- NNGVMERLTTVLQP-DEOSSOPVSA-N 2-[(3s)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-(4-methylpiperazin-1-yl)pent-2-enenitrile Chemical compound C1CN(C)CCN1C(C)(C)C=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 NNGVMERLTTVLQP-DEOSSOPVSA-N 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- LCFFREMLXLZNHE-GBOLQPHISA-N (e)-2-[(3r)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile Chemical compound C12=C(N)N=CN=C2N([C@@H]2CCCN(C2)C(=O)C(/C#N)=C/C(C)(C)N2CCN(CC2)C2COC2)N=C1C(C(=C1)F)=CC=C1OC1=CC=CC=C1 LCFFREMLXLZNHE-GBOLQPHISA-N 0.000 claims 6
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 6
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 125000004193 piperazinyl group Chemical group 0.000 claims 6
- NNGVMERLTTVLQP-XMMPIXPASA-N 2-[(3r)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-(4-methylpiperazin-1-yl)pent-2-enenitrile Chemical compound C1CN(C)CCN1C(C)(C)C=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 NNGVMERLTTVLQP-XMMPIXPASA-N 0.000 claims 5
- LCFFREMLXLZNHE-VWLOTQADSA-N 2-[(3s)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile Chemical compound C12=C(N)N=CN=C2N([C@H]2CCCN(C2)C(=O)C(C#N)=CC(C)(C)N2CCN(CC2)C2COC2)N=C1C(C(=C1)F)=CC=C1OC1=CC=CC=C1 LCFFREMLXLZNHE-VWLOTQADSA-N 0.000 claims 4
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims 4
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 3
- MWAPCVRIQHXPBI-UHFFFAOYSA-N CC(C=CC#N)(C)N1CCN(CC1)C1COC1 Chemical compound CC(C=CC#N)(C)N1CCN(CC1)C1COC1 MWAPCVRIQHXPBI-UHFFFAOYSA-N 0.000 claims 3
- 206010025323 Lymphomas Diseases 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- LCFFREMLXLZNHE-UHFFFAOYSA-N 2-[3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(oxetan-3-yl)piperazin-1-yl]pent-2-enenitrile Chemical compound NC1=C2C(=NC=N1)N(N=C2C1=C(C=C(C=C1)OC1=CC=CC=C1)F)C1CN(CCC1)C(=O)C(C#N)=CC(C)(N1CCN(CC1)C1COC1)C LCFFREMLXLZNHE-UHFFFAOYSA-N 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 208000011691 Burkitt lymphomas Diseases 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 206010012438 Dermatitis atopic Diseases 0.000 claims 2
- 206010013774 Dry eye Diseases 0.000 claims 2
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 2
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims 2
- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010046851 Uveitis Diseases 0.000 claims 2
- 206010047115 Vasculitis Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 201000008937 atopic dermatitis Diseases 0.000 claims 2
- 201000000448 autoimmune hemolytic anemia Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 208000024908 graft versus host disease Diseases 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 206010025135 lupus erythematosus Diseases 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 206010028417 myasthenia gravis Diseases 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- OTSKDHVXZWBYCH-RUZDIDTESA-N 2-[(2R)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-(4-ethylpiperazin-1-yl)-4-methylpent-2-enenitrile Chemical compound CCN1CCN(CC1)C(C)(C)C=C(C#N)C(=O)N1CCC[C@@H]1Cn1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12 OTSKDHVXZWBYCH-RUZDIDTESA-N 0.000 claims 1
- OECSGHDUGHCIMQ-HSZRJFAPSA-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-(2-oxa-6-azaspiro[3.3]heptan-6-yl)pent-2-enenitrile Chemical compound CC(C)(C=C(C#N)C(=O)N1CCC[C@@H]1Cn1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12)N1CC2(COC2)C1 OECSGHDUGHCIMQ-HSZRJFAPSA-N 0.000 claims 1
- UAXREQATXBHJAW-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-(4-methylpiperazin-1-yl)pent-2-enenitrile Chemical compound CN1CCN(CC1)C(C)(C)C=C(C#N)C(=O)N1CCC[C@@H]1Cn1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12 UAXREQATXBHJAW-XMMPIXPASA-N 0.000 claims 1
- ULQLAFJMRPZCJZ-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-(oxetan-3-ylamino)pent-2-enenitrile Chemical compound CC(C)(NC1COC1)C=C(C#N)C(=O)N1CCC[C@@H]1Cn1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12 ULQLAFJMRPZCJZ-JOCHJYFZSA-N 0.000 claims 1
- YELZMARZEBVKBL-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-[methyl(oxetan-3-yl)amino]pent-2-enenitrile Chemical compound CN(C1COC1)C(C)(C)C=C(C#N)C(=O)N1CCC[C@@H]1Cn1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12 YELZMARZEBVKBL-JOCHJYFZSA-N 0.000 claims 1
- VZXQFGIJCJMSFZ-HSZRJFAPSA-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-piperazin-1-ylpent-2-enenitrile Chemical compound CC(C)(C=C(C#N)C(=O)N1CCC[C@@H]1Cn1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12)N1CCNCC1 VZXQFGIJCJMSFZ-HSZRJFAPSA-N 0.000 claims 1
- OTSKDHVXZWBYCH-VWLOTQADSA-N 2-[(2S)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-(4-ethylpiperazin-1-yl)-4-methylpent-2-enenitrile Chemical compound CCN1CCN(CC1)C(C)(C)C=C(C#N)C(=O)N1CCC[C@H]1Cn1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12 OTSKDHVXZWBYCH-VWLOTQADSA-N 0.000 claims 1
- YDXOXEUWKYKVDD-DEOSSOPVSA-N 2-[(2S)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-[cyclopropyl(oxetan-3-yl)amino]-4-methylpent-2-enenitrile Chemical compound CC(C)(C=C(C#N)C(=O)N1CCC[C@H]1Cn1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12)N(C1CC1)C1COC1 YDXOXEUWKYKVDD-DEOSSOPVSA-N 0.000 claims 1
- UAXREQATXBHJAW-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-(4-methylpiperazin-1-yl)pent-2-enenitrile Chemical compound CN1CCN(CC1)C(C)(C)C=C(C#N)C(=O)N1CCC[C@H]1Cn1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12 UAXREQATXBHJAW-DEOSSOPVSA-N 0.000 claims 1
- ULQLAFJMRPZCJZ-QFIPXVFZSA-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-(oxetan-3-ylamino)pent-2-enenitrile Chemical compound CC(C)(NC1COC1)C=C(C#N)C(=O)N1CCC[C@H]1Cn1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12 ULQLAFJMRPZCJZ-QFIPXVFZSA-N 0.000 claims 1
- YELZMARZEBVKBL-QFIPXVFZSA-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-[methyl(oxetan-3-yl)amino]pent-2-enenitrile Chemical compound CN(C1COC1)C(C)(C)C=C(C#N)C(=O)N1CCC[C@H]1Cn1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12 YELZMARZEBVKBL-QFIPXVFZSA-N 0.000 claims 1
- VZXQFGIJCJMSFZ-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-piperazin-1-ylpent-2-enenitrile Chemical compound CC(C)(C=C(C#N)C(=O)N1CCC[C@H]1Cn1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12)N1CCNCC1 VZXQFGIJCJMSFZ-QHCPKHFHSA-N 0.000 claims 1
- YDXOXEUWKYKVDD-XMMPIXPASA-N 2-[(2r)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-[cyclopropyl(oxetan-3-yl)amino]-4-methylpent-2-enenitrile Chemical compound C([C@H]1CCCN1C(=O)C(C#N)=CC(C)(C)N(C1CC1)C1COC1)N(C1=NC=NC(N)=C11)N=C1C(C(=C1)F)=CC=C1OC1=CC=CC=C1 YDXOXEUWKYKVDD-XMMPIXPASA-N 0.000 claims 1
- BYINIOQJRGRANK-HSZRJFAPSA-N 2-[(2r)-2-[[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]pyrrolidine-1-carbonyl]-4-[ethyl(oxetan-3-yl)amino]-4-methylpent-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)=CC(C)(C)N(CC)C1COC1 BYINIOQJRGRANK-HSZRJFAPSA-N 0.000 claims 1
- DEUQAIWVYRNFIH-GIFXNVAJSA-N 2-[(3R)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-[(3S,5R)-3,5-dimethylpiperazin-1-yl]-4-methylpent-2-enenitrile Chemical compound C[C@H]1CN(C[C@@H](C)N1)C(C)(C)C=C(C#N)C(=O)N1CCC[C@H](C1)n1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12 DEUQAIWVYRNFIH-GIFXNVAJSA-N 0.000 claims 1
- NIYAGZIDNIWGFF-AREMUKBSSA-N 2-[(3R)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-[4-(2-methoxyethyl)piperazin-1-yl]-4-methylpent-2-enenitrile Chemical compound COCCN1CCN(CC1)C(C)(C)C=C(C#N)C(=O)N1CCC[C@H](C1)n1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12 NIYAGZIDNIWGFF-AREMUKBSSA-N 0.000 claims 1
- SGXVGVKVFFHVGS-HSZRJFAPSA-N 2-[(3R)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-(4-methyl-3-oxopiperazin-1-yl)pent-2-enenitrile Chemical compound CN1CCN(CC1=O)C(C)(C)C=C(C#N)C(=O)N1CCC[C@H](C1)n1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12 SGXVGVKVFFHVGS-HSZRJFAPSA-N 0.000 claims 1
- MURPPFZYZLNBQN-XMMPIXPASA-N 2-[(3R)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-(4-methylsulfonylpiperazin-1-yl)pent-2-enenitrile Chemical compound CC(C)(C=C(C#N)C(=O)N1CCC[C@H](C1)n1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12)N1CCN(CC1)S(C)(=O)=O MURPPFZYZLNBQN-XMMPIXPASA-N 0.000 claims 1
- BICRABDPLNFWOV-AREMUKBSSA-N 2-[(3R)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-(4-propan-2-ylpiperazin-1-yl)pent-2-enenitrile Chemical compound CC(C)N1CCN(CC1)C(C)(C)C=C(C#N)C(=O)N1CCC[C@H](C1)n1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12 BICRABDPLNFWOV-AREMUKBSSA-N 0.000 claims 1
- ZKIWYNDTGRBYQF-RMTZWNOUSA-N 2-[(3R)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[(3S,5R)-3,4,5-trimethylpiperazin-1-yl]pent-2-enenitrile Chemical compound C[C@H]1CN(C[C@@H](C)N1C)C(C)(C)C=C(C#N)C(=O)N1CCC[C@H](C1)n1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12 ZKIWYNDTGRBYQF-RMTZWNOUSA-N 0.000 claims 1
- NOXVOMASUWKHPG-XMMPIXPASA-N 2-[(3R)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[4-(2,2,2-trifluoroethyl)piperazin-1-yl]pent-2-enenitrile Chemical compound CC(C)(C=C(C#N)C(=O)N1CCC[C@H](C1)n1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12)N1CCN(CC(F)(F)F)CC1 NOXVOMASUWKHPG-XMMPIXPASA-N 0.000 claims 1
- WBBFEPYVCBJYOO-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-[methyl(oxetan-3-yl)amino]pent-2-enenitrile Chemical compound CN(C1COC1)C(C)(C)C=C(C#N)C(=O)N1CCC[C@H](C1)n1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12 WBBFEPYVCBJYOO-JOCHJYFZSA-N 0.000 claims 1
- MURPPFZYZLNBQN-DEOSSOPVSA-N 2-[(3S)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-(4-methylsulfonylpiperazin-1-yl)pent-2-enenitrile Chemical compound CC(C)(C=C(C#N)C(=O)N1CCC[C@@H](C1)n1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12)N1CCN(CC1)S(C)(=O)=O MURPPFZYZLNBQN-DEOSSOPVSA-N 0.000 claims 1
- BICRABDPLNFWOV-SANMLTNESA-N 2-[(3S)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-(4-propan-2-ylpiperazin-1-yl)pent-2-enenitrile Chemical compound CC(C)N1CCN(CC1)C(C)(C)C=C(C#N)C(=O)N1CCC[C@@H](C1)n1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12 BICRABDPLNFWOV-SANMLTNESA-N 0.000 claims 1
- WBBFEPYVCBJYOO-QFIPXVFZSA-N 2-[(3S)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4-methyl-4-[methyl(oxetan-3-yl)amino]pent-2-enenitrile Chemical compound CN(C1COC1)C(C)(C)C=C(C#N)C(=O)N1CCC[C@@H](C1)n1nc(-c2ccc(Oc3ccccc3)cc2F)c2c(N)ncnc12 WBBFEPYVCBJYOO-QFIPXVFZSA-N 0.000 claims 1
- JYZBKNSSHGQRHT-XMMPIXPASA-N 2-[(3r)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carbonyl]-4,4-dimethyl-5-morpholin-4-ylpent-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)CN1CCOCC1 JYZBKNSSHGQRHT-XMMPIXPASA-N 0.000 claims 1
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