ES2543050T3 - Inhibidores de serina/treonina quinasa - Google Patents

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Publication number

ES2543050T3

ES2543050T3 ES12709429.0T ES12709429T ES2543050T3 ES 2543050 T3 ES2543050 T3 ES 2543050T3 ES 12709429 T ES12709429 T ES 12709429T ES 2543050 T3 ES2543050 T3 ES 2543050T3

Authority

ES

Spain

Prior art keywords

dihydro

phenyl

pyrido

amide

pyrimidin

Prior art date

2011-02-28

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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• 229940043355 kinase inhibitor Drugs 0.000 title description 3
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 3
• 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 title description 2
• 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 title description 2
• -1 benzoimidazolyl Chemical group 0.000 claims abstract description 1179
• 150000001875 compounds Chemical class 0.000 claims abstract description 182
• 239000001257 hydrogen Substances 0.000 claims abstract description 112
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 112
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 68
• 150000003839 salts Chemical class 0.000 claims abstract description 68
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 66
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 64
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 62
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 59
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 56
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 56
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 52
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 47
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 47
• 150000002367 halogens Chemical class 0.000 claims abstract description 47
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 46
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract description 45
• 125000003118 aryl group Chemical group 0.000 claims abstract description 43
• 150000002431 hydrogen Chemical group 0.000 claims abstract description 32
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 28
• 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 27
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 26
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 23
• 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 21
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract description 21
• 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 21
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 20
• 125000002252 acyl group Chemical group 0.000 claims abstract description 19
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 19
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
• 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 17
• 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 17
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 17
• 125000004429 atom Chemical group 0.000 claims abstract description 16
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 16
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 15
• 125000001041 indolyl group Chemical group 0.000 claims abstract description 15
• 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 15
• 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 14
• 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 14
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
• 125000001425 triazolyl group Chemical group 0.000 claims abstract description 13
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims abstract description 12
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 12
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims abstract description 12
• 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 11
• 125000000842 isoxazolyl group Chemical group 0.000 claims abstract description 10
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims abstract description 9
• 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 9
• 125000001786 isothiazolyl group Chemical group 0.000 claims abstract description 9
• 125000001715 oxadiazolyl group Chemical group 0.000 claims abstract description 9
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 8
• 125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 8
• 125000004306 triazinyl group Chemical group 0.000 claims abstract description 8
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 7
• 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims abstract description 7
• 125000004442 acylamino group Chemical group 0.000 claims abstract description 7
• 125000005843 halogen group Chemical group 0.000 claims abstract description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims abstract description 6
• 125000002393 azetidinyl group Chemical group 0.000 claims abstract description 6
• 125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 6
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract description 6
• 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims abstract description 5
• LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims abstract description 5
• 125000003566 oxetanyl group Chemical group 0.000 claims abstract description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 5
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
• 125000004104 aryloxy group Chemical group 0.000 claims abstract description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
• HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims abstract description 3
• 239000002253 acid Substances 0.000 claims description 185
• 239000000203 mixture Substances 0.000 claims description 63
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 45
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 44
• 208000035475 disorder Diseases 0.000 claims description 35
• 206010028980 Neoplasm Diseases 0.000 claims description 32
• 230000003463 hyperproliferative effect Effects 0.000 claims description 27
• CYZCJADBZVABTN-MRVPVSSYSA-N (2s)-2-amino-2-(3-chloro-4-fluorophenyl)ethanol Chemical compound OC[C@@H](N)C1=CC=C(F)C(Cl)=C1 CYZCJADBZVABTN-MRVPVSSYSA-N 0.000 claims description 26
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
• 238000011282 treatment Methods 0.000 claims description 22
• 201000011510 cancer Diseases 0.000 claims description 21
• UJUFOUVXOUYYRG-RXMQYKEDSA-N (1r)-1-(3,4-dichlorophenyl)ethanamine Chemical compound C[C@@H](N)C1=CC=C(Cl)C(Cl)=C1 UJUFOUVXOUYYRG-RXMQYKEDSA-N 0.000 claims description 20
• 102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 claims description 18
• 108010007457 Extracellular Signal-Regulated MAP Kinases Proteins 0.000 claims description 17
• 230000000694 effects Effects 0.000 claims description 17
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 15
• BLNCONOUQXEUCP-MRVPVSSYSA-N (2s)-2-amino-2-(4-chloro-3-fluorophenyl)ethanol Chemical compound OC[C@@H](N)C1=CC=C(Cl)C(F)=C1 BLNCONOUQXEUCP-MRVPVSSYSA-N 0.000 claims description 14
• QNCIKNHLGKDVGE-UHFFFAOYSA-N 6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid Chemical compound N1=CN=CC=2C1=CN(CC2)C(=O)O QNCIKNHLGKDVGE-UHFFFAOYSA-N 0.000 claims description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
• 201000009030 Carcinoma Diseases 0.000 claims description 9
• 239000003085 diluting agent Substances 0.000 claims description 9
• 125000001188 haloalkyl group Chemical group 0.000 claims description 9
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 230000006872 improvement Effects 0.000 claims description 8
• 206010009944 Colon cancer Diseases 0.000 claims description 7
• 239000002246 antineoplastic agent Substances 0.000 claims description 7
• 229940127089 cytotoxic agent Drugs 0.000 claims description 7
• CYZCJADBZVABTN-UHFFFAOYSA-N 2-amino-2-(3-chloro-4-fluorophenyl)ethanol Chemical compound OCC(N)C1=CC=C(F)C(Cl)=C1 CYZCJADBZVABTN-UHFFFAOYSA-N 0.000 claims description 6
• 208000026310 Breast neoplasm Diseases 0.000 claims description 6
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 6
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 6
• 201000005202 lung cancer Diseases 0.000 claims description 6
• 208000020816 lung neoplasm Diseases 0.000 claims description 6
• 201000002528 pancreatic cancer Diseases 0.000 claims description 6
• QNQUBGPYUVRMSB-SECBINFHSA-N (1r)-1-(4-chloro-3-fluorophenyl)propan-1-amine Chemical compound CC[C@@H](N)C1=CC=C(Cl)C(F)=C1 QNQUBGPYUVRMSB-SECBINFHSA-N 0.000 claims description 5
• MIFMZIPFCNEFBM-SECBINFHSA-N (1r)-1-[4-(difluoromethoxy)phenyl]propan-1-amine Chemical compound CC[C@@H](N)C1=CC=C(OC(F)F)C=C1 MIFMZIPFCNEFBM-SECBINFHSA-N 0.000 claims description 5
• YTHACPLZDAHPTP-MRVPVSSYSA-N (2s)-2-amino-2-[4-(difluoromethoxy)phenyl]ethanol Chemical compound OC[C@@H](N)C1=CC=C(OC(F)F)C=C1 YTHACPLZDAHPTP-MRVPVSSYSA-N 0.000 claims description 5
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 5
• NNZNDGFJDKAJLG-UHFFFAOYSA-N 1h-2,6-naphthyridine-2-carboxylic acid Chemical compound C1=NC=C2C=CN(C(=O)O)CC2=C1 NNZNDGFJDKAJLG-UHFFFAOYSA-N 0.000 claims description 5
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
• BLNCONOUQXEUCP-UHFFFAOYSA-N 2-amino-2-(4-chloro-3-fluorophenyl)ethanol Chemical compound OCC(N)C1=CC=C(Cl)C(F)=C1 BLNCONOUQXEUCP-UHFFFAOYSA-N 0.000 claims description 5
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
• 206010006187 Breast cancer Diseases 0.000 claims description 5
• 206010033128 Ovarian cancer Diseases 0.000 claims description 5
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 5
• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 5
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 5
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 5
• FFQSFXAOMSUUCV-SECBINFHSA-N (1R)-1-(3-fluoro-4-methoxyphenyl)propan-1-amine Chemical compound CC[C@@H](N)C1=CC=C(OC)C(F)=C1 FFQSFXAOMSUUCV-SECBINFHSA-N 0.000 claims description 4
• FCOAUPWCOYGMFE-MRVPVSSYSA-N (1R)-1-[3-fluoro-4-(trifluoromethoxy)phenyl]propan-1-amine Chemical compound CC[C@@H](N)c1ccc(OC(F)(F)F)c(F)c1 FCOAUPWCOYGMFE-MRVPVSSYSA-N 0.000 claims description 4
• BVVJDCFVSXSRBB-RXMQYKEDSA-N (1r)-1-(3-chloro-5-fluorophenyl)ethanamine Chemical compound C[C@@H](N)C1=CC(F)=CC(Cl)=C1 BVVJDCFVSXSRBB-RXMQYKEDSA-N 0.000 claims description 4
• SRVZZCBLNXFARS-RXMQYKEDSA-N (1r)-1-(4-chloro-3-fluorophenyl)ethanamine Chemical compound C[C@@H](N)C1=CC=C(Cl)C(F)=C1 SRVZZCBLNXFARS-RXMQYKEDSA-N 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 4
• 208000027866 inflammatory disease Diseases 0.000 claims description 4
• 201000002510 thyroid cancer Diseases 0.000 claims description 4
• VBWRNUHVGFPJRG-SECBINFHSA-N (1r)-1-(3,4-dichlorophenyl)propan-1-amine Chemical compound CC[C@@H](N)C1=CC=C(Cl)C(Cl)=C1 VBWRNUHVGFPJRG-SECBINFHSA-N 0.000 claims description 3
• QGCLEUGNYRXBMZ-ZCFIWIBFSA-N (1r)-1-(4-fluorophenyl)ethanamine Chemical compound C[C@@H](N)C1=CC=C(F)C=C1 QGCLEUGNYRXBMZ-ZCFIWIBFSA-N 0.000 claims description 3
• KZXMHEBPONONDK-OIBJUYFYSA-N (3S,4R)-4-(4-chloro-3-fluorophenyl)pyrrolidin-3-amine Chemical compound N[C@@H]1CNC[C@H]1C1=CC=C(Cl)C(F)=C1 KZXMHEBPONONDK-OIBJUYFYSA-N 0.000 claims description 3
• JCGNJHHXMLDXRC-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)propane-1,3-diamine Chemical compound NCCC(N)C1=CC=C(Cl)C(Cl)=C1 JCGNJHHXMLDXRC-UHFFFAOYSA-N 0.000 claims description 3
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
• 206010005003 Bladder cancer Diseases 0.000 claims description 3
• DSHGWXMIUPNWEP-CYBMUJFWSA-N C1([C@@H](C)NC(=O)N2CCC3=CN=C(N=C3C2)NC(C)C)=CC=C(F)C=C1 Chemical compound C1([C@@H](C)NC(=O)N2CCC3=CN=C(N=C3C2)NC(C)C)=CC=C(F)C=C1 DSHGWXMIUPNWEP-CYBMUJFWSA-N 0.000 claims description 3
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
• 208000008930 Low Back Pain Diseases 0.000 claims description 3
• 206010060862 Prostate cancer Diseases 0.000 claims description 3
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• 208000015634 Rectal Neoplasms Diseases 0.000 claims description 3
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• 239000003937 drug carrier Substances 0.000 claims description 3
• 208000005017 glioblastoma Diseases 0.000 claims description 3
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• 201000005112 urinary bladder cancer Diseases 0.000 claims description 3
• HVAKTAOFRQKFME-SNVBAGLBSA-N (1R)-1-[4-(2,2,2-trifluoroethoxy)phenyl]propan-1-amine Chemical compound CC[C@@H](N)C1=CC=C(OCC(F)(F)F)C=C1 HVAKTAOFRQKFME-SNVBAGLBSA-N 0.000 claims description 2
• QHARBBFZGIDKLK-RXMQYKEDSA-N (1r)-1-(3-chloro-4-fluorophenyl)ethanamine Chemical compound C[C@@H](N)C1=CC=C(F)C(Cl)=C1 QHARBBFZGIDKLK-RXMQYKEDSA-N 0.000 claims description 2
• BWZFVQWUKNCKQL-SECBINFHSA-N (1r)-1-(4-fluorophenyl)propan-1-amine Chemical compound CC[C@@H](N)C1=CC=C(F)C=C1 BWZFVQWUKNCKQL-SECBINFHSA-N 0.000 claims description 2
• MIFMZIPFCNEFBM-VIFPVBQESA-N (1s)-1-[4-(difluoromethoxy)phenyl]propan-1-amine Chemical compound CC[C@H](N)C1=CC=C(OC(F)F)C=C1 MIFMZIPFCNEFBM-VIFPVBQESA-N 0.000 claims description 2
• CTBPDZHZGYKVRA-UHFFFAOYSA-N (4-chloro-3-fluorophenyl)-(1,3-oxazol-5-yl)methanamine Chemical compound C=1C=C(Cl)C(F)=CC=1C(N)C1=CN=CO1 CTBPDZHZGYKVRA-UHFFFAOYSA-N 0.000 claims description 2
• JLXWGARTNXOMLA-SNVBAGLBSA-N (R)-(4-chloro-3-fluorophenyl)-(1,3-oxazol-4-yl)methanamine Chemical compound C1([C@H](N)C=2C=C(F)C(Cl)=CC=2)=COC=N1 JLXWGARTNXOMLA-SNVBAGLBSA-N 0.000 claims description 2
• UGTQLRZGDVYBRH-LLVKDONJSA-N (R)-(4-chloro-3-fluorophenyl)-(1-methylpyrazol-4-yl)methanamine Chemical compound Cn1cc(cn1)[C@H](N)c1ccc(Cl)c(F)c1 UGTQLRZGDVYBRH-LLVKDONJSA-N 0.000 claims description 2
• JLXWGARTNXOMLA-JTQLQIEISA-N (S)-(4-chloro-3-fluorophenyl)-(1,3-oxazol-4-yl)methanamine Chemical compound C1([C@@H](N)C=2C=C(F)C(Cl)=CC=2)=COC=N1 JLXWGARTNXOMLA-JTQLQIEISA-N 0.000 claims description 2
• BYXLFFDKBZRBOD-ZDUSSCGKSA-N (S)-[3-fluoro-4-(trifluoromethyl)phenyl]-(6-methoxypyridin-2-yl)methanamine Chemical compound COc1cccc(n1)[C@@H](N)c1ccc(c(F)c1)C(F)(F)F BYXLFFDKBZRBOD-ZDUSSCGKSA-N 0.000 claims description 2
• UGTQLRZGDVYBRH-NSHDSACASA-N (s)-(4-chloro-3-fluorophenyl)-(1-methylpyrazol-4-yl)methanamine Chemical compound C1=NN(C)C=C1[C@@H](N)C1=CC=C(Cl)C(F)=C1 UGTQLRZGDVYBRH-NSHDSACASA-N 0.000 claims description 2
• RFWDQVNFSXQMMI-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3,3,3-trifluoropropan-1-amine Chemical compound FC(F)(F)CC(N)C1=CC=C(Cl)C(Cl)=C1 RFWDQVNFSXQMMI-UHFFFAOYSA-N 0.000 claims description 2
• UCOSRTUSVXHIMK-UHFFFAOYSA-N 1h-benzimidazol-2-ylmethanamine Chemical compound C1=CC=C2NC(CN)=NC2=C1 UCOSRTUSVXHIMK-UHFFFAOYSA-N 0.000 claims description 2
• QWSYXQMUSXKUCN-OAHLLOKOSA-N 2-(oxan-4-ylamino)-N-[(1R)-1-phenylethyl]-6,8-dihydro-5H-pyrido[3,4-d]pyrimidine-7-carboxamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(=O)N(CC1=N2)CCC1=CN=C2NC1CCOCC1 QWSYXQMUSXKUCN-OAHLLOKOSA-N 0.000 claims description 2
• ZRKJGGGKZXIGPE-UHFFFAOYSA-N 3-[1-[2-(oxan-4-ylamino)-6,8-dihydro-5H-pyrido[3,4-d]pyrimidine-7-carbonyl]pyrrolidin-2-yl]benzonitrile Chemical compound C1CC2=CN=C(NC3CCOCC3)N=C2CN1C(=O)N1CCCC1C1=CC=CC(C#N)=C1 ZRKJGGGKZXIGPE-UHFFFAOYSA-N 0.000 claims description 2
• MIYUHKALQKBPEW-UHFFFAOYSA-N 4-(aminomethyl)-2-chlorobenzonitrile Chemical compound NCC1=CC=C(C#N)C(Cl)=C1 MIYUHKALQKBPEW-UHFFFAOYSA-N 0.000 claims description 2
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