BR112016012146B1 - Compostos derivados de aminopiridina como inibidores quinase da família tam, composição farmacêutica compreendendo ditos compostos e uso terapêutico dos mesmos - Google Patents

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Publication number

BR112016012146B1

BR112016012146B1 BR112016012146-5A BR112016012146A BR112016012146B1 BR 112016012146 B1 BR112016012146 B1 BR 112016012146B1 BR 112016012146 A BR112016012146 A BR 112016012146A BR 112016012146 B1 BR112016012146 B1 BR 112016012146B1

Authority

BR

Brazil

Prior art keywords

pyridin

pyrazol

oxadiazol

amine

piperidin

Prior art date

2013-11-27

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• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 49
• 150000001875 compounds Chemical class 0.000 title claims description 315
• 108091077436 Tam family Proteins 0.000 title abstract description 10
• 150000003927 aminopyridines Chemical class 0.000 title abstract description 4
• 229940043355 kinase inhibitor Drugs 0.000 title abstract description 4
• 239000003757 phosphotransferase inhibitor Substances 0.000 title abstract description 4
• 230000001225 therapeutic effect Effects 0.000 title description 3
• -1 benzophthofuranyl Chemical group 0.000 claims description 152
• 238000002360 preparation method Methods 0.000 claims description 119
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 76
• 239000001257 hydrogen Substances 0.000 claims description 71
• 229910052739 hydrogen Inorganic materials 0.000 claims description 71
• 125000003118 aryl group Chemical group 0.000 claims description 59
• 125000000623 heterocyclic group Chemical group 0.000 claims description 58
• 125000000217 alkyl group Chemical group 0.000 claims description 54
• 125000001072 heteroaryl group Chemical group 0.000 claims description 52
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
• 206010028980 Neoplasm Diseases 0.000 claims description 27
• 201000010099 disease Diseases 0.000 claims description 26
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 17
• 125000001188 haloalkyl group Chemical group 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 201000011510 cancer Diseases 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 125000004076 pyridyl group Chemical group 0.000 claims description 12
• 206010006187 Breast cancer Diseases 0.000 claims description 11
• 208000026310 Breast neoplasm Diseases 0.000 claims description 11
• 201000009273 Endometriosis Diseases 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 125000000335 thiazolyl group Chemical group 0.000 claims description 8
• JCTRWHSQGKHHPN-UHFFFAOYSA-N 3-(3-phenyl-1,2,4-oxadiazol-5-yl)-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound C1(=CC=CC=C1)C1=NOC(=N1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCNCC1)N JCTRWHSQGKHHPN-UHFFFAOYSA-N 0.000 claims description 7
• 208000002177 Cataract Diseases 0.000 claims description 7
• 208000032839 leukemia Diseases 0.000 claims description 7
• 125000002971 oxazolyl group Chemical group 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• DIVKPPRZFNTJJY-UHFFFAOYSA-N 3-[5-(4-chlorophenyl)-1,3-oxazol-2-yl]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound ClC1=CC=C(C=C1)C1=CN=C(O1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCNCC1)N DIVKPPRZFNTJJY-UHFFFAOYSA-N 0.000 claims description 6
• 208000007536 Thrombosis Diseases 0.000 claims description 6
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• 201000001441 melanoma Diseases 0.000 claims description 6
• 201000008482 osteoarthritis Diseases 0.000 claims description 6
• 208000037803 restenosis Diseases 0.000 claims description 6
• 208000001132 Osteoporosis Diseases 0.000 claims description 5
• 201000004681 Psoriasis Diseases 0.000 claims description 5
• 206010038933 Retinopathy of prematurity Diseases 0.000 claims description 5
• 206010052779 Transplant rejections Diseases 0.000 claims description 5
• 208000002780 macular degeneration Diseases 0.000 claims description 5
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
• 125000001425 triazolyl group Chemical group 0.000 claims description 5
• RGCPVFHDBYPACT-UHFFFAOYSA-N 3-[5-(3-chlorophenyl)-1,3-oxazol-2-yl]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound ClC=1C=C(C=CC1)C1=CN=C(O1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCNCC1)N RGCPVFHDBYPACT-UHFFFAOYSA-N 0.000 claims description 4
• 201000001320 Atherosclerosis Diseases 0.000 claims description 4
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 4
• 206010025323 Lymphomas Diseases 0.000 claims description 4
• 206010060862 Prostate cancer Diseases 0.000 claims description 4
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 4
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000005870 benzindolyl group Chemical group 0.000 claims description 4
• 125000005605 benzo group Chemical group 0.000 claims description 4
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 4
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 4
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 4
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
• 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims description 4
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
• LMUXUZFXNUNSIF-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-[5-(2,6-dichlorophenyl)-1,3,4-oxadiazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-2-phenylethanone Chemical compound NC1=C(C=C(C=N1)C=1C=NN(C1)C1CCN(CC1)C(CC1=CC=CC=C1)=O)C=1OC(=NN1)C1=C(C=CC=C1Cl)Cl LMUXUZFXNUNSIF-UHFFFAOYSA-N 0.000 claims description 3
• JDZXATSSHQQCKE-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-[5-(2,6-dichlorophenyl)-1,3,4-oxadiazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-4-methylpentan-1-one Chemical compound NC1=C(C=C(C=N1)C=1C=NN(C1)C1CCN(CC1)C(CCC(C)C)=O)C=1OC(=NN1)C1=C(C=CC=C1Cl)Cl JDZXATSSHQQCKE-UHFFFAOYSA-N 0.000 claims description 3
• YWKNLZNQZUWUJN-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-[5-(2,6-dichlorophenyl)-1,3,4-oxadiazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]ethanone Chemical compound CC(=O)N1CCC(CC1)N1C=C(C=N1)C1=CC(C2=NN=C(O2)C2=C(Cl)C=CC=C2Cl)=C(N)N=C1 YWKNLZNQZUWUJN-UHFFFAOYSA-N 0.000 claims description 3
• NQYVWMHYPZYTJQ-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-[5-(3-chlorophenyl)-1,3-oxazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]ethanone Chemical compound NC1=C(C=C(C=N1)C=1C=NN(C1)C1CCN(CC1)C(C)=O)C=1OC(=CN1)C1=CC(=CC=C1)Cl NQYVWMHYPZYTJQ-UHFFFAOYSA-N 0.000 claims description 3
• HJCIOJLLUQLYKS-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-[5-(4-chlorophenyl)-1,3-oxazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]ethanone Chemical compound CC(=O)N1CCC(CC1)N1C=C(C=N1)C1=CC(C2=NC=C(O2)C2=CC=C(Cl)C=C2)=C(N)N=C1 HJCIOJLLUQLYKS-UHFFFAOYSA-N 0.000 claims description 3
• QVQVNNUWZLJWNI-UHFFFAOYSA-N 3-(5-phenyl-1,3-oxazol-2-yl)-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound C1(=CC=CC=C1)C1=CN=C(O1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCNCC1)N QVQVNNUWZLJWNI-UHFFFAOYSA-N 0.000 claims description 3
• ZBTBHQRMQLOGTA-UHFFFAOYSA-N 3-[5-(2,6-dichlorophenyl)-1,3,4-oxadiazol-2-yl]-5-[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound CN1CCC(CC1)N1C=C(C=N1)C1=CN=C(N)C(=C1)C1=NN=C(O1)C1=C(Cl)C=CC=C1Cl ZBTBHQRMQLOGTA-UHFFFAOYSA-N 0.000 claims description 3
• IJLBAXYWKUBUSP-UHFFFAOYSA-N 5-(1-cyclohexylpyrazol-4-yl)-3-(5-phenyl-1,2,4-oxadiazol-3-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NOC(=N1)C1=CC=CC=C1)C1=CN(N=C1)C1CCCCC1 IJLBAXYWKUBUSP-UHFFFAOYSA-N 0.000 claims description 3
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
• 206010039491 Sarcoma Diseases 0.000 claims description 3
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 3
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 3
• 206010064930 age-related macular degeneration Diseases 0.000 claims description 3
• 125000000928 benzodioxinyl group Chemical group O1C(=COC2=C1C=CC=C2)* 0.000 claims description 3
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 3
• 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 3
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
• JFSPBVWPKOEZCB-UHFFFAOYSA-N fenfuram Chemical compound O1C=CC(C(=O)NC=2C=CC=CC=2)=C1C JFSPBVWPKOEZCB-UHFFFAOYSA-N 0.000 claims description 3
• 206010017758 gastric cancer Diseases 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• 201000011549 stomach cancer Diseases 0.000 claims description 3
• ZRZISHTXGMXYAI-UHFFFAOYSA-N tert-butyl 4-[4-[6-amino-5-(5-phenyl-1,3-oxazol-2-yl)pyridin-3-yl]pyrazol-1-yl]piperidine-1-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CCC(CC1)N1N=CC(=C1)C=1C=NC(=C(C1)C=1OC(=CN1)C1=CC=CC=C1)N ZRZISHTXGMXYAI-UHFFFAOYSA-N 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• 201000002510 thyroid cancer Diseases 0.000 claims description 3
• TZHAMZFQCRXJQL-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-(3-phenyl-1,2,4-oxadiazol-5-yl)pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-2-phenylethanone Chemical compound NC1=C(C=C(C=N1)C=1C=NN(C1)C1CCN(CC1)C(CC1=CC=CC=C1)=O)C1=NC(=NO1)C1=CC=CC=C1 TZHAMZFQCRXJQL-UHFFFAOYSA-N 0.000 claims description 2
• BGWDTMSGTXYLFQ-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-(3-phenyl-1,2,4-oxadiazol-5-yl)pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]ethanone Chemical compound NC1=C(C=C(C=N1)C=1C=NN(C1)C1CCN(CC1)C(C)=O)C1=NC(=NO1)C1=CC=CC=C1 BGWDTMSGTXYLFQ-UHFFFAOYSA-N 0.000 claims description 2
• BEZNVVMPNAFFQH-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-[5-(3-chlorophenyl)-1,3-oxazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-2,2-dimethylpropan-1-one Chemical compound CC(C)(C)C(=O)N1CCC(CC1)N1C=C(C=N1)C1=CC(C2=NC=C(O2)C2=CC(Cl)=CC=C2)=C(N)N=C1 BEZNVVMPNAFFQH-UHFFFAOYSA-N 0.000 claims description 2
• UDJOVSNJZDGILO-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-[5-(3-chlorophenyl)-1,3-oxazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-2-phenylethanone Chemical compound NC1=C(C=C(C=N1)C1=CN(N=C1)C1CCN(CC1)C(=O)CC1=CC=CC=C1)C1=NC=C(O1)C1=CC(Cl)=CC=C1 UDJOVSNJZDGILO-UHFFFAOYSA-N 0.000 claims description 2
• UTPPMYCLWHXGRC-UHFFFAOYSA-N 1-[4-[4-[6-amino-5-[5-(4-chlorophenyl)-1,3-oxazol-2-yl]pyridin-3-yl]pyrazol-1-yl]piperidin-1-yl]-2-phenylethanone Chemical compound NC1=C(C=C(C=N1)C1=CN(N=C1)C1CCN(CC1)C(=O)CC1=CC=CC=C1)C1=NC=C(O1)C1=CC=C(Cl)C=C1 UTPPMYCLWHXGRC-UHFFFAOYSA-N 0.000 claims description 2
• RXYFHESTJMGSCY-UHFFFAOYSA-N 3-(3-phenyl-1,2,4-oxadiazol-5-yl)-5-(1H-pyrazol-4-yl)pyridin-2-amine Chemical compound C1(=CC=CC=C1)C1=NOC(=N1)C=1C(=NC=C(C1)C=1C=NNC1)N RXYFHESTJMGSCY-UHFFFAOYSA-N 0.000 claims description 2
• BBAFIJXSLKRXFF-UHFFFAOYSA-N 3-(5-phenyl-1,2,4-oxadiazol-3-yl)-5-(1H-pyrazol-4-yl)pyridin-2-amine Chemical compound C1(=CC=CC=C1)C1=NC(=NO1)C=1C(=NC=C(C1)C=1C=NNC1)N BBAFIJXSLKRXFF-UHFFFAOYSA-N 0.000 claims description 2
• GTVXNXCPIWOXMW-UHFFFAOYSA-N 3-(5-phenyl-1,2-oxazol-3-yl)-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound C1(=CC=CC=C1)C1=CC(=NO1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCNCC1)N GTVXNXCPIWOXMW-UHFFFAOYSA-N 0.000 claims description 2
• YEIHOAOJELGJES-UHFFFAOYSA-N 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-5-(1H-pyrazol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=CC=CC=C1)C1=CNN=C1 YEIHOAOJELGJES-UHFFFAOYSA-N 0.000 claims description 2
• HUDJQOWWQNOZMU-UHFFFAOYSA-N 3-(5-phenylfuran-2-yl)-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound C1(=CC=CC=C1)C1=CC=C(O1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCNCC1)N HUDJQOWWQNOZMU-UHFFFAOYSA-N 0.000 claims description 2
• QOGFSNMJMBNROD-UHFFFAOYSA-N 3-[3-(2,6-dichlorophenyl)-1,2,4-oxadiazol-5-yl]-5-[1-(1-dodecylpiperidin-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound CCCCCCCCCCCCN1CCC(CC1)N1C=C(C=N1)C1=CN=C(N)C(=C1)C1=NC(=NO1)C1=C(Cl)C=CC=C1Cl QOGFSNMJMBNROD-UHFFFAOYSA-N 0.000 claims description 2
• QGXKCALPBVKDSW-UHFFFAOYSA-N 3-[3-(2,6-dichlorophenyl)-1,2,4-oxadiazol-5-yl]-5-[1-(1-ethylpiperidin-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound CCN1CCC(CC1)N1C=C(C=N1)C1=CN=C(N)C(=C1)C1=NC(=NO1)C1=C(Cl)C=CC=C1Cl QGXKCALPBVKDSW-UHFFFAOYSA-N 0.000 claims description 2
• VSCOLQXVVSAKLE-UHFFFAOYSA-N 3-[3-(2,6-dichlorophenyl)-1,2,4-oxadiazol-5-yl]-5-[1-(oxan-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound ClC1=C(C(=CC=C1)Cl)C1=NOC(=N1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCOCC1)N VSCOLQXVVSAKLE-UHFFFAOYSA-N 0.000 claims description 2
• CUCXAKDPZVGKIC-UHFFFAOYSA-N 3-[5-(2,5-difluorophenyl)-1,3,4-oxadiazol-2-yl]-5-(1H-pyrazol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=C(F)C=CC(F)=C1)C1=CNN=C1 CUCXAKDPZVGKIC-UHFFFAOYSA-N 0.000 claims description 2
• ZCLZKGMBFGLEIJ-UHFFFAOYSA-N 3-[5-(2,6-dichloro-3-fluorophenyl)-1,3,4-oxadiazol-2-yl]-5-(1-piperidin-4-ylpyrazol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=C(Cl)C(F)=CC=C1Cl)C1=CN(N=C1)C1CCNCC1 ZCLZKGMBFGLEIJ-UHFFFAOYSA-N 0.000 claims description 2
• IMQAWWNWZMSFBP-UHFFFAOYSA-N 3-[5-(2,6-dichlorophenyl)-1,3,4-oxadiazol-2-yl]-5-(1h-pyrazol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C2=CNN=C2)C=C1C(O1)=NN=C1C1=C(Cl)C=CC=C1Cl IMQAWWNWZMSFBP-UHFFFAOYSA-N 0.000 claims description 2
• FJLRRTVVKQMQDA-UHFFFAOYSA-N 3-[5-(2,6-dichlorophenyl)-1,3,4-oxadiazol-2-yl]-5-[1-(1-dodecylpiperidin-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound CCCCCCCCCCCCN1CCC(CC1)N1C=C(C=N1)C1=CN=C(N)C(=C1)C1=NN=C(O1)C1=C(Cl)C=CC=C1Cl FJLRRTVVKQMQDA-UHFFFAOYSA-N 0.000 claims description 2
• LWRKYLRRDIXJHM-UHFFFAOYSA-N 3-[5-(2,6-dichlorophenyl)-1,3,4-oxadiazol-2-yl]-5-[1-(oxan-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=C(Cl)C=CC=C1Cl)C1=CN(N=C1)C1CCOCC1 LWRKYLRRDIXJHM-UHFFFAOYSA-N 0.000 claims description 2
• BMUXXIXZPXPFGC-UHFFFAOYSA-N 3-[5-(3-chlorophenyl)-1,3-oxazol-2-yl]-5-(1-cyclohexylpyrazol-4-yl)pyridin-2-amine Chemical compound ClC=1C=C(C=CC1)C1=CN=C(O1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCCCC1)N BMUXXIXZPXPFGC-UHFFFAOYSA-N 0.000 claims description 2
• WJWSQCJSOYBLLQ-UHFFFAOYSA-N 3-[5-(3-chlorophenyl)-1,3-oxazol-2-yl]-5-[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound ClC=1C=C(C=CC1)C1=CN=C(O1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCN(CC1)C)N WJWSQCJSOYBLLQ-UHFFFAOYSA-N 0.000 claims description 2
• WXZVALFJKXFFRX-UHFFFAOYSA-N 3-[5-(4-chlorophenyl)-1,3-oxazol-2-yl]-5-(1-cyclohexylpyrazol-4-yl)pyridin-2-amine Chemical compound ClC1=CC=C(C=C1)C1=CN=C(O1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCCCC1)N WXZVALFJKXFFRX-UHFFFAOYSA-N 0.000 claims description 2
• NKXDTNWKAQEPET-UHFFFAOYSA-N 3-[5-(4-chlorophenyl)-1,3-oxazol-2-yl]-5-[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]pyridin-2-amine Chemical compound ClC1=CC=C(C=C1)C1=CN=C(O1)C=1C(=NC=C(C1)C=1C=NN(C1)C1CCN(CC1)C)N NKXDTNWKAQEPET-UHFFFAOYSA-N 0.000 claims description 2
• VMQUDSYSZTXZRK-UHFFFAOYSA-N 3-[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]-5-(1H-pyrazol-4-yl)pyridin-2-amine Chemical compound NC1=NC=C(C=C1C1=NN=C(O1)C1=CC=C(F)C=C1)C1=CNN=C1 VMQUDSYSZTXZRK-UHFFFAOYSA-N 0.000 claims description 2
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