CA2730231C - Polycyclic heteroaryl substituted triazoles useful as axl inhibitors - Google Patents
Polycyclic heteroaryl substituted triazoles useful as axl inhibitors Download PDFInfo
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- CA2730231C CA2730231C CA2730231A CA2730231A CA2730231C CA 2730231 C CA2730231 C CA 2730231C CA 2730231 A CA2730231 A CA 2730231A CA 2730231 A CA2730231 A CA 2730231A CA 2730231 C CA2730231 C CA 2730231C
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- CA
- Canada
- Prior art keywords
- benzo
- tetrahydro
- annulene
- dihydro
- cyclohepta
- 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.)
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- 239000003112 inhibitor Substances 0.000 title abstract description 6
- 150000003852 triazoles Chemical class 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 371
- 239000000203 mixture Substances 0.000 claims abstract description 113
- 150000003839 salts Chemical class 0.000 claims abstract description 75
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 48
- 239000001257 hydrogen Substances 0.000 claims abstract description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 48
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 35
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 34
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 32
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 31
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 27
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 27
- 125000001424 substituent group Chemical group 0.000 claims abstract description 23
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 8
- -1 5-chlorothien-2-yl Chemical group 0.000 claims description 89
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 53
- 201000010099 disease Diseases 0.000 claims description 43
- 230000000694 effects Effects 0.000 claims description 39
- 239000008194 pharmaceutical composition Substances 0.000 claims description 35
- 241000124008 Mammalia Species 0.000 claims description 23
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims 12
- UBAAHDCJBVMPCK-QHCPKHFHSA-N 1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-3-n-[(7s)-7-(propan-2-ylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=CC=CC=C2C(N=N2)=C1C=C2N1C(N)=NC(NC2=CC=C3CC[C@@H](CCC3=C2)NC(C)C)=N1 UBAAHDCJBVMPCK-QHCPKHFHSA-N 0.000 claims 2
- LVCPKOMFJZAWIW-VWLOTQADSA-N 3-n-[(7s)-7-(cyclopentylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound N([C@H]1CCC2=CC=C(C=C2CC1)NC=1N=C(N(N=1)C=1N=NC=2C3=CC=CC=C3CCCC=2C=1)N)C1CCCC1 LVCPKOMFJZAWIW-VWLOTQADSA-N 0.000 claims 2
- CDKLEXAJBHUVIZ-VWLOTQADSA-N 3-n-[(7s)-7-(diethylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=CC=CC=C2C(N=N2)=C1C=C2N1C(N)=NC(NC2=CC=C3CC[C@@H](CCC3=C2)N(CC)CC)=N1 CDKLEXAJBHUVIZ-VWLOTQADSA-N 0.000 claims 2
- SQYDXKZXQCAOJD-UHFFFAOYSA-N 1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-3-n-(7-pyrrolidin-1-yl-6,7,8,9-tetrahydro-5h-benzo[7]annulen-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound N=1N(C=2N=NC=3C4=CC=CC=C4CCCC=3C=2)C(N)=NC=1NC(C=1CC2)=CC=CC=1CCC2N1CCCC1 SQYDXKZXQCAOJD-UHFFFAOYSA-N 0.000 claims 1
- KWYXLWSWWHDWCS-SANMLTNESA-N 1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-3-n-[(7s)-7-(2-ethylbutylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=CC=CC=C2C(N=N2)=C1C=C2N1C(N)=NC(NC2=CC=C3CC[C@@H](CCC3=C2)NCC(CC)CC)=N1 KWYXLWSWWHDWCS-SANMLTNESA-N 0.000 claims 1
- YHFBUVNVTQCFOG-DEOSSOPVSA-N 1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-3-n-[(7s)-7-(2-methylpropylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=CC=CC=C2C(N=N2)=C1C=C2N1C(N)=NC(NC2=CC=C3CC[C@@H](CCC3=C2)NCC(C)C)=N1 YHFBUVNVTQCFOG-DEOSSOPVSA-N 0.000 claims 1
- NQPDJPQIHCZBRK-KUXBLMNESA-N 1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-3-n-[(7s)-7-(3,3-dimethylbutan-2-ylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=CC=CC=C2C(N=N2)=C1C=C2N1C(N)=NC(NC2=CC=C3CC[C@@H](CCC3=C2)NC(C)C(C)(C)C)=N1 NQPDJPQIHCZBRK-KUXBLMNESA-N 0.000 claims 1
- VIKZFDFSYDOZEN-VWLOTQADSA-N 1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-3-n-[(7s)-7-(3-methylbutylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=CC=CC=C2C(N=N2)=C1C=C2N1C(N)=NC(NC2=CC=C3CC[C@@H](CCC3=C2)NCCC(C)C)=N1 VIKZFDFSYDOZEN-VWLOTQADSA-N 0.000 claims 1
- SBSRNWKAWADMOO-QHCPKHFHSA-N 1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-3-n-[(7s)-7-(dimethylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=CC=CC=C2C(N=N2)=C1C=C2N1C(N)=NC(NC2=CC=C3CC[C@@H](CCC3=C2)N(C)C)=N1 SBSRNWKAWADMOO-QHCPKHFHSA-N 0.000 claims 1
- MQHHNNRKHMVMJR-MHZLTWQESA-N 1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-3-n-[(7s)-7-(dipropylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=CC=CC=C2C(N=N2)=C1C=C2N1C(N)=NC(NC2=CC=C3CC[C@@H](CCC3=C2)N(CCC)CCC)=N1 MQHHNNRKHMVMJR-MHZLTWQESA-N 0.000 claims 1
- AVQQXOHZLAYZEH-VWLOTQADSA-N 1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-3-n-[(7s)-7-(pentan-3-ylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=CC=CC=C2C(N=N2)=C1C=C2N1C(N)=NC(NC2=CC=C3CC[C@@H](CCC3=C2)NC(CC)CC)=N1 AVQQXOHZLAYZEH-VWLOTQADSA-N 0.000 claims 1
- YQLHBRVIPXLMRR-QHCPKHFHSA-N 1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-3-n-[(7s)-7-(propylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=CC=CC=C2C(N=N2)=C1C=C2N1C(N)=NC(NC2=CC=C3CC[C@@H](CCC3=C2)NCCC)=N1 YQLHBRVIPXLMRR-QHCPKHFHSA-N 0.000 claims 1
- QTDLUUCYXBLQGG-UHFFFAOYSA-N 1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-5-n-(7-pyrrolidin-1-yl-6,7,8,9-tetrahydro-5h-benzo[7]annulen-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound C=1C=2CCCC3=CC=CC=C3C=2N=NC=1N1N=C(N)N=C1NC(C=1CC2)=CC=CC=1CCC2N1CCCC1 QTDLUUCYXBLQGG-UHFFFAOYSA-N 0.000 claims 1
- UZSWXPOKCCSEQO-NRFANRHFSA-N 1-(6,7-dihydro-5h-pyrido[4,5]cyclohepta[1,2-d]pyridazin-3-yl)-3-n-[(7s)-7-(dimethylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=NC=CC=C2C(N=N2)=C1C=C2N1C(N)=NC(NC2=CC=C3CC[C@@H](CCC3=C2)N(C)C)=N1 UZSWXPOKCCSEQO-NRFANRHFSA-N 0.000 claims 1
- UNLIZDNGFMLFHW-VWLOTQADSA-N 1-(6,7-dihydro-5h-pyrido[4,5]cyclohepta[1,2-d]pyridazin-3-yl)-3-n-[(7s)-7-(dipropylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=NC=CC=C2C(N=N2)=C1C=C2N1C(N)=NC(NC2=CC=C3CC[C@@H](CCC3=C2)N(CCC)CCC)=N1 UNLIZDNGFMLFHW-VWLOTQADSA-N 0.000 claims 1
- KDXFSIPXCZLHDK-NRFANRHFSA-N 1-(6,7-dihydro-5h-pyrido[4,5]cyclohepta[1,2-d]pyridazin-3-yl)-3-n-[(7s)-7-(propan-2-ylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=NC=CC=C2C(N=N2)=C1C=C2N1C(N)=NC(NC2=CC=C3CC[C@@H](CCC3=C2)NC(C)C)=N1 KDXFSIPXCZLHDK-NRFANRHFSA-N 0.000 claims 1
- FSPOKNMNFBNRON-UHFFFAOYSA-N 1-[3-[[5-amino-1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-1,2,4-triazol-3-yl]amino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-7-yl]piperidine-4-carboxylic acid Chemical compound N=1N(C=2N=NC=3C4=CC=CC=C4CCCC=3C=2)C(N)=NC=1NC(C=C1CC2)=CC=C1CCC2N1CCC(C(O)=O)CC1 FSPOKNMNFBNRON-UHFFFAOYSA-N 0.000 claims 1
- CHJJYJREFIVXAY-UHFFFAOYSA-N 2-[4-[3-[[5-amino-1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-1,2,4-triazol-3-yl]amino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-7-yl]piperazin-1-yl]acetic acid Chemical compound N=1N(C=2N=NC=3C4=CC=CC=C4CCCC=3C=2)C(N)=NC=1NC(C=C1CC2)=CC=C1CCC2N1CCN(CC(O)=O)CC1 CHJJYJREFIVXAY-UHFFFAOYSA-N 0.000 claims 1
- OHFHJFLDYUYOBZ-YQAGWJQESA-N 3-n-[(7s)-7-(1-cyclopentylethylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound N([C@@H]1CCC2=CC(NC3=NN(C(N)=N3)C=3N=NC=4C5=CC=CC=C5CCCC=4C=3)=CC=C2CC1)C(C)C1CCCC1 OHFHJFLDYUYOBZ-YQAGWJQESA-N 0.000 claims 1
- FNFVSBGPVGBOMM-ILEDHWTGSA-N 3-n-[(7s)-7-(5-bicyclo[2.2.1]hept-2-enylmethylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=CC=CC=C2C(N=N2)=C1C=C2N1N=C(NC=2C=C3CC[C@H](CCC3=CC=2)NCC2C3CC(C=C3)C2)N=C1N FNFVSBGPVGBOMM-ILEDHWTGSA-N 0.000 claims 1
- OKETXTLCKYVVGS-DEOSSOPVSA-N 3-n-[(7s)-7-(but-2-enylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=CC=CC=C2C(N=N2)=C1C=C2N1C(N)=NC(NC2=CC=C3CC[C@@H](CCC3=C2)NCC=CC)=N1 OKETXTLCKYVVGS-DEOSSOPVSA-N 0.000 claims 1
- CIAVBPWKMZQOBR-YSYXNDDBSA-N 3-n-[(7s)-7-(butan-2-ylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1-(6,7-dihydro-5h-pyrido[4,5]cyclohepta[1,2-d]pyridazin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=NC=CC=C2C(N=N2)=C1C=C2N1C(N)=NC(NC2=CC=C3CC[C@@H](CCC3=C2)NC(C)CC)=N1 CIAVBPWKMZQOBR-YSYXNDDBSA-N 0.000 claims 1
- PSOLXTLGQVOFNW-DEOSSOPVSA-N 3-n-[(7s)-7-(cyclobutylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound N([C@H]1CCC2=CC=C(C=C2CC1)NC=1N=C(N(N=1)C=1N=NC=2C3=CC=CC=C3CCCC=2C=1)N)C1CCC1 PSOLXTLGQVOFNW-DEOSSOPVSA-N 0.000 claims 1
- FPAPTNJCGJVHKK-QFIPXVFZSA-N 3-n-[(7s)-7-(cyclobutylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1-(6,7-dihydro-5h-pyrido[4,5]cyclohepta[1,2-d]pyridazin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound N([C@H]1CCC2=CC=C(C=C2CC1)NC=1N=C(N(N=1)C=1N=NC=2C3=CC=CN=C3CCCC=2C=1)N)C1CCC1 FPAPTNJCGJVHKK-QFIPXVFZSA-N 0.000 claims 1
- YOEAUOGMBGPMMT-SANMLTNESA-N 3-n-[(7s)-7-(cyclohexylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound N([C@H]1CCC2=CC=C(C=C2CC1)NC=1N=C(N(N=1)C=1N=NC=2C3=CC=CC=C3CCCC=2C=1)N)C1CCCCC1 YOEAUOGMBGPMMT-SANMLTNESA-N 0.000 claims 1
- DYYDWJPYZAHRRQ-DEOSSOPVSA-N 3-n-[(7s)-7-(cyclohexylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1-(6,7-dihydro-5h-pyrido[4,5]cyclohepta[1,2-d]pyridazin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound N([C@H]1CCC2=CC=C(C=C2CC1)NC=1N=C(N(N=1)C=1N=NC=2C3=CC=CN=C3CCCC=2C=1)N)C1CCCCC1 DYYDWJPYZAHRRQ-DEOSSOPVSA-N 0.000 claims 1
- AORQXLBAZAEXDL-MHZLTWQESA-N 3-n-[(7s)-7-(cyclohexylmethylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound N([C@H]1CCC2=CC=C(C=C2CC1)NC=1N=C(N(N=1)C=1N=NC=2C3=CC=CC=C3CCCC=2C=1)N)CC1CCCCC1 AORQXLBAZAEXDL-MHZLTWQESA-N 0.000 claims 1
- KLFMEFCCQLKUQV-QHCPKHFHSA-N 3-n-[(7s)-7-(diethylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1-(6,7-dihydro-5h-pyrido[4,5]cyclohepta[1,2-d]pyridazin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=NC=CC=C2C(N=N2)=C1C=C2N1C(N)=NC(NC2=CC=C3CC[C@@H](CCC3=C2)N(CC)CC)=N1 KLFMEFCCQLKUQV-QHCPKHFHSA-N 0.000 claims 1
- RQRWWCGUPNGDFC-MHZLTWQESA-N 3-n-[(7s)-7-[(3-bromophenyl)methylamino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound N([C@H]1CCC2=CC=C(C=C2CC1)NC=1N=C(N(N=1)C=1N=NC=2C3=CC=CC=C3CCCC=2C=1)N)CC1=CC=CC(Br)=C1 RQRWWCGUPNGDFC-MHZLTWQESA-N 0.000 claims 1
- QMHNCYIHCBASJY-LJAQVGFWSA-N 3-n-[(7s)-7-[bis(3-methylbutyl)amino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1-(6,7-dihydro-5h-pyrido[4,5]cyclohepta[1,2-d]pyridazin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=NC=CC=C2C(N=N2)=C1C=C2N1C(N)=NC(NC2=CC=C3CC[C@@H](CCC3=C2)N(CCC(C)C)CCC(C)C)=N1 QMHNCYIHCBASJY-LJAQVGFWSA-N 0.000 claims 1
- MYVORLVWAKHHQJ-WYDGGWBJSA-N 3-n-[(7s)-7-[bis(5-bicyclo[2.2.1]hept-2-enylmethyl)amino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=CC=CC=C2C(N=N2)=C1C=C2N1N=C(NC=2C=C3CC[C@H](CCC3=CC=2)N(CC2C3CC(C=C3)C2)CC2C3CC(C=C3)C2)N=C1N MYVORLVWAKHHQJ-WYDGGWBJSA-N 0.000 claims 1
- KHNYYIPWKKQAJM-XIFFEERXSA-N 3-n-[(7s)-7-[bis(cyclopentylmethyl)amino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound C1CCCC1CN([C@H]1CCC2=CC=C(C=C2CC1)NC=1N=C(N(N=1)C=1N=NC=2C3=CC=CC=C3CCCC=2C=1)N)CC1CCCC1 KHNYYIPWKKQAJM-XIFFEERXSA-N 0.000 claims 1
- BCLWHSHMYCWVGD-LJAQVGFWSA-N 3-n-[(7s)-7-[bis(cyclopropylmethyl)amino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound C1CC1CN([C@H]1CCC2=CC=C(C=C2CC1)NC=1N=C(N(N=1)C=1N=NC=2C3=CC=CC=C3CCCC=2C=1)N)CC1CC1 BCLWHSHMYCWVGD-LJAQVGFWSA-N 0.000 claims 1
- WZLAMPGFENXANI-MHZLTWQESA-N 3-n-[(7s)-7-[bis(cyclopropylmethyl)amino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1-(6,7-dihydro-5h-pyrido[4,5]cyclohepta[1,2-d]pyridazin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound C1CC1CN([C@H]1CCC2=CC=C(C=C2CC1)NC=1N=C(N(N=1)C=1N=NC=2C3=CC=CN=C3CCCC=2C=1)N)CC1CC1 WZLAMPGFENXANI-MHZLTWQESA-N 0.000 claims 1
- NXPBSZXADCHBAM-LJAQVGFWSA-N 3-n-[(7s)-7-[but-2-enyl(butyl)amino]-6,7,8,9-tetrahydro-5h-benzo[7]annulen-3-yl]-1-(6,7-dihydro-5h-benzo[2,3]cyclohepta[2,4-d]pyridazin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound C1CCC2=CC=CC=C2C(N=N2)=C1C=C2N1C(N)=NC(NC2=CC=C3CC[C@@H](CCC3=C2)N(CC=CC)CCCC)=N1 NXPBSZXADCHBAM-LJAQVGFWSA-N 0.000 claims 1
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
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Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7940308P | 2008-07-09 | 2008-07-09 | |
| US61/079,403 | 2008-07-09 | ||
| PCT/US2009/049617 WO2010005876A2 (en) | 2008-07-09 | 2009-07-02 | Polycyclic heteroaryl substituted triazoles useful as axl inhibitors |
Publications (2)
| Publication Number | Publication Date |
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| CA2730231A1 CA2730231A1 (en) | 2010-01-14 |
| CA2730231C true CA2730231C (en) | 2016-10-18 |
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| CA2730231A Active CA2730231C (en) | 2008-07-09 | 2009-07-02 | Polycyclic heteroaryl substituted triazoles useful as axl inhibitors |
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| US (3) | US8349838B2 (enExample) |
| EP (1) | EP2326641B1 (enExample) |
| JP (1) | JP5592884B2 (enExample) |
| CA (1) | CA2730231C (enExample) |
| ES (1) | ES2537480T3 (enExample) |
| WO (1) | WO2010005876A2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1922310A2 (en) * | 2005-09-07 | 2008-05-21 | Rigel Pharmaceuticals, Inc. | Triazole derivatives useful as axl inhibitors |
| PT2114955E (pt) | 2006-12-29 | 2013-04-18 | Rigel Pharmaceuticals Inc | Triazoles substituídos com arilo bicíclico em ponte ou heteroarilo bicíclico em ponte úteis como inibidores de axl |
| US7872000B2 (en) | 2006-12-29 | 2011-01-18 | Rigel Pharmaceuticals, Inc. | Bicyclic aryl and bicyclic heteroaryl substituted triazoles useful as Axl inhibitors |
| JP2010514810A (ja) | 2006-12-29 | 2010-05-06 | ライジェル ファーマシューティカルズ， インコーポレイテッド | Ａｘｌインヒビターとして有用な置換トリアゾール |
| ES2607065T3 (es) * | 2006-12-29 | 2017-03-29 | Rigel Pharmaceuticals, Inc. | Triazoles N3-heteroaril sustituidos y triazoles N5-heteroaril sustituidos útiles como inhibidores de axl |
| PL2078010T3 (pl) | 2006-12-29 | 2014-07-31 | Rigel Pharmaceuticals Inc | Triazole podstawione policyklicznym heteroarylem użyteczne jako inhibitory Axl |
| CA2704052C (en) * | 2007-10-26 | 2015-04-21 | Rigel Pharmaceuticals, Inc. | Polycyclic aryl substituted triazoles and polycyclic heteroaryl substituted triazoles useful as axl inhibitors |
| CA2715658C (en) | 2008-02-15 | 2016-07-19 | Rigel Pharmaceuticals, Inc. | Pyrimidine-2-amine compounds and their use as inhibitors of jak kinases |
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| WO2010005876A3 (en) | 2010-07-01 |
| CA2730231A1 (en) | 2010-01-14 |
| US9173882B2 (en) | 2015-11-03 |
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| US8349838B2 (en) | 2013-01-08 |
| US20110105511A1 (en) | 2011-05-05 |
| ES2537480T3 (es) | 2015-06-08 |
| EP2326641B1 (en) | 2014-09-03 |
| WO2010005876A2 (en) | 2010-01-14 |
| US20150216864A1 (en) | 2015-08-06 |
| US9079898B2 (en) | 2015-07-14 |
| US20130109695A1 (en) | 2013-05-02 |
| JP5592884B2 (ja) | 2014-09-17 |
| HK1158625A1 (en) | 2012-07-20 |
| EP2326641A2 (en) | 2011-06-01 |
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