JP2017510554A5 - - Google Patents
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- Publication number
- JP2017510554A5 JP2017510554A5 JP2016551710A JP2016551710A JP2017510554A5 JP 2017510554 A5 JP2017510554 A5 JP 2017510554A5 JP 2016551710 A JP2016551710 A JP 2016551710A JP 2016551710 A JP2016551710 A JP 2016551710A JP 2017510554 A5 JP2017510554 A5 JP 2017510554A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- alkyl
- amino
- piperidin
- phenylcyclopropyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 117
- 150000003839 salts Chemical class 0.000 claims 63
- 150000001875 compounds Chemical class 0.000 claims 53
- 125000005843 halogen group Chemical group 0.000 claims 36
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 31
- 125000003118 aryl group Chemical group 0.000 claims 30
- -1 cyanomethyl Chemical group 0.000 claims 30
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 28
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 21
- 229910052799 carbon Inorganic materials 0.000 claims 21
- 125000001424 substituent group Chemical group 0.000 claims 21
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 19
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 16
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 125000005842 heteroatom Chemical group 0.000 claims 9
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 8
- 239000003814 drug Substances 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000000260 trans-2-phenylcyclopropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])[C@]1([H])C([H])([H])[C@@]1([H])* 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 2
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 2
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 claims 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
- 208000032027 Essential Thrombocythemia Diseases 0.000 claims 2
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 2
- 208000033826 Promyelocytic Acute Leukemia Diseases 0.000 claims 2
- 208000017733 acquired polycythemia vera Diseases 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 201000005787 hematologic cancer Diseases 0.000 claims 2
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 206010028537 myelofibrosis Diseases 0.000 claims 2
- 208000037244 polycythemia vera Diseases 0.000 claims 2
- 208000003476 primary myelofibrosis Diseases 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- SOAHNSKFZYGGEX-BJKOFHAPSA-N (1-aminocyclobutyl)-[4-[(4-fluorophenyl)methyl]-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methanone Chemical compound FC1=CC=C(CC2(CCN(CC2)C(=O)C2(CCC2)N)CN[C@H]2[C@@H](C2)C2=CC=CC=C2)C=C1 SOAHNSKFZYGGEX-BJKOFHAPSA-N 0.000 claims 1
- SLTZFKXINVPGSG-RBUKOAKNSA-N (1-aminocyclopentyl)-[4-methyl-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methanone Chemical compound CC1(CCN(CC1)C(=O)C1(CCCC1)N)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 SLTZFKXINVPGSG-RBUKOAKNSA-N 0.000 claims 1
- AQJLQUFCVASXPB-ZWKOTPCHSA-N (1-methylimidazol-4-yl)-[4-methyl-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methanone Chemical compound CC1(CCN(CC1)C(=O)C=1N=CN(C1)C)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 AQJLQUFCVASXPB-ZWKOTPCHSA-N 0.000 claims 1
- HXBXFCQWRMIMLT-VQTJNVASSA-N (1R,2S)-N-[[1-[(4-fluorophenyl)methyl]azetidin-3-yl]methyl]-2-phenylcyclopropan-1-amine Chemical compound FC1=CC=C(CN2CC(C2)CN[C@H]2[C@@H](C2)C2=CC=CC=C2)C=C1 HXBXFCQWRMIMLT-VQTJNVASSA-N 0.000 claims 1
- VONUFLPVRCWPKX-RBUKOAKNSA-N (1R,2S)-N-[[4-(methoxymethyl)-1-(1-methylpyrazol-3-yl)sulfonylpiperidin-4-yl]methyl]-2-phenylcyclopropan-1-amine Chemical compound COCC1(CCN(CC1)S(=O)(=O)C1=NN(C=C1)C)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 VONUFLPVRCWPKX-RBUKOAKNSA-N 0.000 claims 1
- OZAONMXVFGFFDB-VQTJNVASSA-N (1R,2S)-N-[[4-(methoxymethyl)-1-(1-methylpyrazol-4-yl)sulfonylpiperidin-4-yl]methyl]-2-phenylcyclopropan-1-amine Chemical compound COCC1(CCN(CC1)S(=O)(=O)C=1C=NN(C1)C)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 OZAONMXVFGFFDB-VQTJNVASSA-N 0.000 claims 1
- XVKYTMDZBYKDLP-RBUKOAKNSA-N (1R,2S)-N-[[4-(methoxymethyl)-1-(2-methylpyrazol-3-yl)sulfonylpiperidin-4-yl]methyl]-2-phenylcyclopropan-1-amine Chemical compound COCC1(CCN(CC1)S(=O)(=O)C1=CC=NN1C)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 XVKYTMDZBYKDLP-RBUKOAKNSA-N 0.000 claims 1
- VITZMUSBMJOMAU-ZWKOTPCHSA-N (2-aminopyrimidin-5-yl)-[4-methyl-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methanone Chemical compound CC1(CCN(CC1)C(=O)C=1C=NC(=NC1)N)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 VITZMUSBMJOMAU-ZWKOTPCHSA-N 0.000 claims 1
- ADXGOWHSMAENJW-RBUKOAKNSA-N (3-fluorophenyl)-[3-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]azetidin-1-yl]methanone Chemical compound FC=1C=C(C(=O)N2CC(C2)CN[C@H]2[C@@H](C2)C2=CC=CC=C2)C=CC1 ADXGOWHSMAENJW-RBUKOAKNSA-N 0.000 claims 1
- VSNYMMTZRZKBMV-RBUKOAKNSA-N (3-hydroxyazetidin-1-yl)-[4-(methoxymethyl)-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methanone Chemical compound COCC1(CCN(CC1)C(=O)N1CC(C1)O)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 VSNYMMTZRZKBMV-RBUKOAKNSA-N 0.000 claims 1
- LFYBHODARDYZBG-VQTJNVASSA-N (3-methoxyphenyl)-[3-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]azetidin-1-yl]methanone Chemical compound COC=1C=C(C(=O)N2CC(C2)CN[C@H]2[C@@H](C2)C2=CC=CC=C2)C=CC1 LFYBHODARDYZBG-VQTJNVASSA-N 0.000 claims 1
- ZWVPAXGAELUSCM-JLMCIHFGSA-N (3-methoxypiperidin-1-yl)-[3-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]azetidin-1-yl]methanone Chemical compound COC1CN(CCC1)C(=O)N1CC(C1)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 ZWVPAXGAELUSCM-JLMCIHFGSA-N 0.000 claims 1
- QZWXAWCOMNELDT-YDUIRMPASA-N (3-phenoxypiperidin-1-yl)-[3-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]azetidin-1-yl]methanone Chemical compound O(C1=CC=CC=C1)C1CN(CCC1)C(=O)N1CC(C1)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 QZWXAWCOMNELDT-YDUIRMPASA-N 0.000 claims 1
- XPQIIEXKHBFDQX-RBUKOAKNSA-N (4-fluorophenyl)-[3-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]azetidin-1-yl]methanone Chemical compound FC1=CC=C(C(=O)N2CC(C2)CN[C@H]2[C@@H](C2)C2=CC=CC=C2)C=C1 XPQIIEXKHBFDQX-RBUKOAKNSA-N 0.000 claims 1
- CHMTVVVUSLEWPW-XZOQPEGZSA-N (4-hydroxy-4-phenylpiperidin-1-yl)-[3-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]azetidin-1-yl]methanone Chemical compound C1(=CC=CC=C1)C1(CCN(CC1)C(=O)N1CC(C1)CN[C@H]1[C@@H](C1)C1=CC=CC=C1)O CHMTVVVUSLEWPW-XZOQPEGZSA-N 0.000 claims 1
- QIQCCTGHPWVZSM-LEWJYISDSA-N (4-hydroxypiperidin-1-yl)-[4-(methoxymethyl)-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methanone Chemical compound COCC1(CCN(CC1)C(=O)N1CCC(CC1)O)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 QIQCCTGHPWVZSM-LEWJYISDSA-N 0.000 claims 1
- FWIVWIBIZXMCNC-DOTOQJQBSA-N (5-amino-1H-pyrazol-4-yl)-[4-methyl-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methanone Chemical compound CC1(CCN(CC1)C(=O)C=1C(=NNC1)N)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 FWIVWIBIZXMCNC-DOTOQJQBSA-N 0.000 claims 1
- SLBPMFIYCBPGGO-XUZZJYLKSA-N (5-fluorospiro[1,2-dihydroindole-3,4'-piperidine]-1'-yl)-[3-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]azetidin-1-yl]methanone Chemical compound FC=1C=C2C3(CNC2=CC1)CCN(CC3)C(=O)N3CC(C3)CN[C@H]3[C@@H](C3)C3=CC=CC=C3 SLBPMFIYCBPGGO-XUZZJYLKSA-N 0.000 claims 1
- KCHQHSGAMGHQSK-PKOBYXMFSA-N (6-aminopyridazin-3-yl)-[4-(methoxymethyl)-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methanone Chemical compound COCC1(CCN(CC1)C(=O)C1=CC=C(N=N1)N)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 KCHQHSGAMGHQSK-PKOBYXMFSA-N 0.000 claims 1
- JOOYFEVIUSPWJE-FUHWJXTLSA-N (6-aminopyridazin-3-yl)-[4-methyl-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methanone Chemical compound CC1(CCN(CC1)C(=O)C1=CC=C(N=N1)N)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 JOOYFEVIUSPWJE-FUHWJXTLSA-N 0.000 claims 1
- FPSQMGPANOOROJ-LEWJYISDSA-N 1-[(4-fluorophenyl)methyl]-N-[(1R,2S)-2-phenylcyclopropyl]piperidin-4-amine Chemical compound FC1=CC=C(CN2CCC(CC2)N[C@H]2[C@@H](C2)C2=CC=CC=C2)C=C1 FPSQMGPANOOROJ-LEWJYISDSA-N 0.000 claims 1
- VJFSXNAKZDCINM-RBUKOAKNSA-N 1-[3-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]azetidine-1-carbonyl]piperidine-4-carbonitrile Chemical compound C1(=CC=CC=C1)[C@H]1[C@@H](C1)NCC1CN(C1)C(=O)N1CCC(CC1)C#N VJFSXNAKZDCINM-RBUKOAKNSA-N 0.000 claims 1
- ZBPAYLBHWULFPT-RBUKOAKNSA-N 1-[4-(methoxymethyl)-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidine-1-carbonyl]cyclopropane-1-carbonitrile Chemical compound COCC1(CCN(CC1)C(=O)C1(CC1)C#N)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 ZBPAYLBHWULFPT-RBUKOAKNSA-N 0.000 claims 1
- GYNFNBWRBNJQAY-BJKOFHAPSA-N 1-[[4-(cyclobutylmethoxymethyl)-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methyl]cyclobutane-1-carboxylic acid Chemical compound C1(CCC1)COCC1(CCN(CC1)CC1(CCC1)C(=O)O)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 GYNFNBWRBNJQAY-BJKOFHAPSA-N 0.000 claims 1
- HAOQZWCUJFVTPM-XZOQPEGZSA-N 1-[[4-(cyclobutylmethoxymethyl)-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methyl]cyclopropane-1-carboxylic acid Chemical compound C1(CCC1)COCC1(CCN(CC1)CC1(CC1)C(=O)O)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 HAOQZWCUJFVTPM-XZOQPEGZSA-N 0.000 claims 1
- IJWMKGNGHJPQRQ-LOSJGSFVSA-N 1-[[4-(cyclohexyloxymethyl)-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methyl]cyclobutane-1-carboxylic acid Chemical compound C1(CCCCC1)OCC1(CCN(CC1)CC1(CCC1)C(=O)O)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 IJWMKGNGHJPQRQ-LOSJGSFVSA-N 0.000 claims 1
- LHDBDRJSXYLAEY-BJKOFHAPSA-N 1-[[4-(cyclohexyloxymethyl)-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methyl]cyclopropane-1-carboxylic acid Chemical compound C1(CCCCC1)OCC1(CCN(CC1)CC1(CC1)C(=O)O)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 LHDBDRJSXYLAEY-BJKOFHAPSA-N 0.000 claims 1
- SFNUNNPWVAFSIB-LEWJYISDSA-N 1-[[4-(ethoxymethyl)-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methyl]cyclobutane-1-carboxylic acid Chemical compound C(C)OCC1(CCN(CC1)CC1(CCC1)C(=O)O)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 SFNUNNPWVAFSIB-LEWJYISDSA-N 0.000 claims 1
- FITOWUHOVCAWQI-VQTJNVASSA-N 1-[[4-(ethoxymethyl)-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methyl]cyclopropane-1-carboxylic acid Chemical compound C(C)OCC1(CCN(CC1)CC1(CC1)C(=O)O)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 FITOWUHOVCAWQI-VQTJNVASSA-N 0.000 claims 1
- NKYSMFSRMSTFJE-QYAPWVIVSA-N 1-[[4-(methoxymethyl)-4-[1-[[(1R,2S)-2-phenylcyclopropyl]amino]ethyl]piperidin-1-yl]methyl]cyclobutane-1-carboxylic acid Chemical compound COCC1(CCN(CC1)CC1(CCC1)C(=O)O)C(C)N[C@H]1[C@@H](C1)C1=CC=CC=C1 NKYSMFSRMSTFJE-QYAPWVIVSA-N 0.000 claims 1
- WBPWDDPSYSUQJA-VQTJNVASSA-N 1-[[4-(methoxymethyl)-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methyl]cyclobutane-1-carboxylic acid Chemical compound COCC1(CCN(CC1)CC1(CCC1)C(=O)O)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 WBPWDDPSYSUQJA-VQTJNVASSA-N 0.000 claims 1
- OUHFLPHJVJYMBF-LEWJYISDSA-N 1-[[4-(methoxymethyl)-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methyl]cyclopentane-1-carboxylic acid Chemical compound COCC1(CCN(CC1)CC1(CCCC1)C(=O)O)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 OUHFLPHJVJYMBF-LEWJYISDSA-N 0.000 claims 1
- WXVYOBVVDHYKDR-RBUKOAKNSA-N 1-[[4-(methoxymethyl)-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methyl]cyclopropane-1-carboxylic acid Chemical compound COCC1(CCN(CC1)CC1(CC1)C(=O)O)CN[C@H]1[C@@H](C1)C1=CC=CC=C1 WXVYOBVVDHYKDR-RBUKOAKNSA-N 0.000 claims 1
- SLGVTHWQMQIMBW-UHFFFAOYSA-N 1-[[4-(methoxymethyl)-4-[[[2-(2-methoxyphenyl)cyclopropyl]amino]methyl]piperidin-1-yl]methyl]cyclobutane-1-carboxylic acid Chemical compound COCC1(CCN(CC1)CC1(CCC1)C(=O)O)CNC1C(C1)C1=C(C=CC=C1)OC SLGVTHWQMQIMBW-UHFFFAOYSA-N 0.000 claims 1
- CLNSMUQWWKZARQ-LOSJGSFVSA-N 1-[[4-[(2-cyanophenoxy)methyl]-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methyl]cyclobutane-1-carboxylic acid Chemical compound C(#N)C1=C(OCC2(CCN(CC2)CC2(CCC2)C(=O)O)CN[C@H]2[C@@H](C2)C2=CC=CC=C2)C=CC=C1 CLNSMUQWWKZARQ-LOSJGSFVSA-N 0.000 claims 1
- GOIZVSLYXPEOOA-BJKOFHAPSA-N 1-[[4-[(2-cyanophenoxy)methyl]-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methyl]cyclopropane-1-carboxylic acid Chemical compound C(#N)C1=C(OCC2(CCN(CC2)CC2(CC2)C(=O)O)CN[C@H]2[C@@H](C2)C2=CC=CC=C2)C=CC=C1 GOIZVSLYXPEOOA-BJKOFHAPSA-N 0.000 claims 1
- OBPJTNQRLCABSA-LADGPHEKSA-N 1-[[4-[(2-fluorophenoxy)methyl]-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methyl]cyclobutane-1-carboxylic acid Chemical compound FC1=C(OCC2(CCN(CC2)CC2(CCC2)C(=O)O)CN[C@H]2[C@@H](C2)C2=CC=CC=C2)C=CC=C1 OBPJTNQRLCABSA-LADGPHEKSA-N 0.000 claims 1
- STZLGHHZQLGPOW-JTHBVZDNSA-N 1-[[4-[(2-fluorophenoxy)methyl]-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methyl]cyclopropane-1-carboxylic acid Chemical compound FC1=C(OCC2(CCN(CC2)CC2(CC2)C(=O)O)CN[C@H]2[C@@H](C2)C2=CC=CC=C2)C=CC=C1 STZLGHHZQLGPOW-JTHBVZDNSA-N 0.000 claims 1
- SGSBYMOOZWAAGR-IZZNHLLZSA-N 1-[[4-[(3-cyanophenoxy)methyl]-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methyl]cyclobutane-1-carboxylic acid Chemical compound C(#N)C=1C=C(OCC2(CCN(CC2)CC2(CCC2)C(=O)O)CN[C@H]2[C@@H](C2)C2=CC=CC=C2)C=CC1 SGSBYMOOZWAAGR-IZZNHLLZSA-N 0.000 claims 1
- HDCRRCYDJGFTFR-LOSJGSFVSA-N 1-[[4-[(3-cyanophenoxy)methyl]-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methyl]cyclopropane-1-carboxylic acid Chemical compound C(#N)C=1C=C(OCC2(CCN(CC2)CC2(CC2)C(=O)O)CN[C@H]2[C@@H](C2)C2=CC=CC=C2)C=CC1 HDCRRCYDJGFTFR-LOSJGSFVSA-N 0.000 claims 1
- IXTOKMCDFLOINY-IZZNHLLZSA-N 1-[[4-[(3-cyanophenyl)methyl]-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methyl]cyclobutane-1-carboxylic acid Chemical compound C(#N)C=1C=C(CC2(CCN(CC2)CC2(CCC2)C(=O)O)CN[C@H]2[C@@H](C2)C2=CC=CC=C2)C=CC1 IXTOKMCDFLOINY-IZZNHLLZSA-N 0.000 claims 1
- KIKTUCZVZVPEKU-LOSJGSFVSA-N 1-[[4-[(3-cyanophenyl)methyl]-4-[[[(1R,2S)-2-phenylcyclopropyl]amino]methyl]piperidin-1-yl]methyl]cyclopropane-1-carboxylic acid Chemical compound C(#N)C=1C=C(CC2(CCN(CC2)CC2(CC2)C(=O)O)CN[C@H]2[C@@H](C2)C2=CC=CC=C2)C=CC1 KIKTUCZVZVPEKU-LOSJGSFVSA-N 0.000 claims 1
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| BR112016028219B1 (pt) | 2014-05-30 | 2022-12-06 | Istituto Europeo Di Oncologia S.R.L | Composto ou composição farmacêutica para uso no tratamento ou prevenção do câncer, de uma doença infecciosa, ou de uma doença designada por aberração de metabolismo de energia celular em um indivíduo, processo para obtenção de um composto de fórmula (i) e uso do composto ou composição farmacêutica na fabricação de um medicamento para uso no tratamento ou prevenção do câncer, de uma doença infecciosa, ou de uma doença designada por aberração de metabolismo de energia celular em um indivíduo |
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