CA2710046C - N3-heteroaryl substituted triazoles and n5-heteroaryl substituted triazoles useful as axl inhibitors - Google Patents

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Publication number

CA2710046C

CA2710046C CA2710046A CA2710046A CA2710046C CA 2710046 C CA2710046 C CA 2710046C CA 2710046 A CA2710046 A CA 2710046A CA 2710046 A CA2710046 A CA 2710046A CA 2710046 C CA2710046 C CA 2710046C

Authority

CA

Canada

Prior art keywords

optionally substituted

triazole

diamine

methylthieno

pyrimidin

Prior art date

2006-12-29

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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• 150000003852 triazoles Chemical class 0.000 title abstract description 14
• 239000003112 inhibitor Substances 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 394
• 230000000694 effects Effects 0.000 claims abstract description 57
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 44
• 201000010099 disease Diseases 0.000 claims abstract description 43
• 239000008194 pharmaceutical composition Chemical class 0.000 claims abstract description 35
• -1 4,5-dihydro-1H-benzo[b]azepin-2(3H)-onyl Chemical group 0.000 claims description 304
• 125000001072 heteroaryl group Chemical group 0.000 claims description 191
• 125000000217 alkyl group Chemical group 0.000 claims description 171
• 125000000623 heterocyclic group Chemical group 0.000 claims description 166
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 151
• 125000001188 haloalkyl group Chemical group 0.000 claims description 151
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 150
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 148
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 144
• 239000001257 hydrogen Substances 0.000 claims description 129
• 229910052739 hydrogen Inorganic materials 0.000 claims description 129
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 125
• 125000003107 substituted aryl group Chemical group 0.000 claims description 116
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 112
• 125000002947 alkylene group Chemical group 0.000 claims description 108
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 106
• 150000002431 hydrogen Chemical group 0.000 claims description 99
• 229910052757 nitrogen Inorganic materials 0.000 claims description 70
• 125000003342 alkenyl group Chemical group 0.000 claims description 69
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 61
• 125000001424 substituent group Chemical group 0.000 claims description 54
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 53
• 125000004449 heterocyclylalkenyl group Chemical group 0.000 claims description 51
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 48
• 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 47
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 40
• 125000004450 alkenylene group Chemical group 0.000 claims description 38
• 239000000203 mixture Substances 0.000 claims description 37
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
• 125000004076 pyridyl group Chemical group 0.000 claims description 29
• 150000003839 salts Chemical class 0.000 claims description 28
• 125000004043 oxo group Chemical group O=* 0.000 claims description 27
• 125000000464 thioxo group Chemical group S=* 0.000 claims description 27
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 25
• 241000124008 Mammalia Species 0.000 claims description 23
• 125000004419 alkynylene group Chemical group 0.000 claims description 23
• 125000000304 alkynyl group Chemical group 0.000 claims description 19
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 18
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 17
• 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 16
• 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims description 16
• 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 16
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 16
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 11
• 125000004608 5,6,7,8-tetrahydroquinolinyl group Chemical group N1=C(C=CC=2CCCCC12)* 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 10
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 150000001412 amines Chemical class 0.000 claims description 3
• 125000001475 halogen functional group Chemical group 0.000 claims 24
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 4
• CBGPKIVHJMVWJZ-AWEZNQCLSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-[6-[(3s)-4-(cyclopropylmethyl)-3-methylpiperazin-1-yl]pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C([C@@H]1C)N(C=2N=CC(NC3=NN(C(N)=N3)C=3C=4SC=C(C)C=4N=C(Cl)N=3)=CC=2)CCN1CC1CC1 CBGPKIVHJMVWJZ-AWEZNQCLSA-N 0.000 claims 2
• GYNHVJXRCYEKJE-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-(6-cyclopentyl-7,8-dihydro-5h-1,6-naphthyridin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=C1C2)=CN=C1CCN2C1CCCC1 GYNHVJXRCYEKJE-UHFFFAOYSA-N 0.000 claims 1
• SWRZSOFOXQXKQW-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-(6-pyrrolidin-1-yl-5,6,7,8-tetrahydroquinolin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=C1C2)=CN=C1CCC2N1CCCC1 SWRZSOFOXQXKQW-UHFFFAOYSA-N 0.000 claims 1
• RWSGMFHJSIEOLZ-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-(7-cyclopentyl-5,6,8,9-tetrahydropyrido[2,3-d]azepin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=C1CC2)=CN=C1CCN2C1CCCC1 RWSGMFHJSIEOLZ-UHFFFAOYSA-N 0.000 claims 1
• QYUBPVPPQRJCQU-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-(7-pyrrolidin-1-yl-6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=C1CC2)=CN=C1CCC2N1CCCC1 QYUBPVPPQRJCQU-UHFFFAOYSA-N 0.000 claims 1
• PWIDPYCXJIGJCC-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-[2-(4-pyrrolidin-1-ylpiperidin-1-yl)pyrimidin-5-yl]-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=N1)=CN=C1N(CC1)CCC1N1CCCC1 PWIDPYCXJIGJCC-UHFFFAOYSA-N 0.000 claims 1
• XWPAAJDGNIMUTB-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-[2-[4-(piperidin-1-ylmethyl)piperidin-1-yl]pyrimidin-5-yl]-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=N1)=CN=C1N(CC1)CCC1CN1CCCCC1 XWPAAJDGNIMUTB-UHFFFAOYSA-N 0.000 claims 1
• JKWQKFWORJZXSD-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-[6-(1-methylpiperidin-4-yl)-7,8-dihydro-5h-1,6-naphthyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C1CN(C)CCC1N1CC2=CC(NC3=NN(C(N)=N3)C=3C=4SC=C(C)C=4N=C(Cl)N=3)=CN=C2CC1 JKWQKFWORJZXSD-UHFFFAOYSA-N 0.000 claims 1
• WPYRXIXVWRCXEW-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-[6-(4-cyclopentyl-1,4-diazepan-1-yl)pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=N1)=CC=C1N(CC1)CCCN1C1CCCC1 WPYRXIXVWRCXEW-UHFFFAOYSA-N 0.000 claims 1
• GMMXICVAAIWGSF-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-[6-(4-cyclopropylpiperazin-1-yl)pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=N1)=CC=C1N(CC1)CCN1C1CC1 GMMXICVAAIWGSF-UHFFFAOYSA-N 0.000 claims 1
• HLCJVMZCBRJAOO-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-[6-(4-methylpiperazin-1-yl)-5,6,7,8-tetrahydroquinolin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C1CN(C)CCN1C1CC2=CC(NC3=NN(C(N)=N3)C=3C=4SC=C(C)C=4N=C(Cl)N=3)=CN=C2CC1 HLCJVMZCBRJAOO-UHFFFAOYSA-N 0.000 claims 1
• VDPVAYDKOMDMHA-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-[6-(4-methylpiperazin-1-yl)pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C1CN(C)CCN1C(N=C1)=CC=C1NC1=NN(C=2C=3SC=C(C)C=3N=C(Cl)N=2)C(N)=N1 VDPVAYDKOMDMHA-UHFFFAOYSA-N 0.000 claims 1
• HBNLLUFZTJCVTF-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-[6-(4-piperidin-1-ylpiperidin-1-yl)pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=N1)=CC=C1N(CC1)CCC1N1CCCCC1 HBNLLUFZTJCVTF-UHFFFAOYSA-N 0.000 claims 1
• RGWKJDDQLPDDEW-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-[6-(4-pyrrolidin-1-ylpiperidin-1-yl)pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=N1)=CC=C1N(CC1)CCC1N1CCCC1 RGWKJDDQLPDDEW-UHFFFAOYSA-N 0.000 claims 1
• FWTFGHCBZCJPAI-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-[6-(cyclopropylmethyl)-7,8-dihydro-5h-1,6-naphthyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=C1C2)=CN=C1CCN2CC1CC1 FWTFGHCBZCJPAI-UHFFFAOYSA-N 0.000 claims 1
• XPWSIHFLGJXLOU-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-[6-[2-(diethylaminomethyl)pyrrolidin-1-yl]pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound CCN(CC)CC1CCCN1C(N=C1)=CC=C1NC1=NN(C=2C=3SC=C(C)C=3N=C(Cl)N=2)C(N)=N1 XPWSIHFLGJXLOU-UHFFFAOYSA-N 0.000 claims 1
• ONDJRPMCKZZNCN-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-[6-[3-(diethylamino)pyrrolidin-1-yl]pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C1C(N(CC)CC)CCN1C(N=C1)=CC=C1NC1=NN(C=2C=3SC=C(C)C=3N=C(Cl)N=2)C(N)=N1 ONDJRPMCKZZNCN-UHFFFAOYSA-N 0.000 claims 1
• UHOILFJRRJAYEQ-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-[6-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C1CN(C)CCN1C1CCN(C=2N=CC(NC3=NN(C(N)=N3)C=3C=4SC=C(C)C=4N=C(Cl)N=3)=CC=2)CC1 UHOILFJRRJAYEQ-UHFFFAOYSA-N 0.000 claims 1
• MRAHXQIWSUTRMV-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-[6-[4-(cyclopropylmethyl)piperazin-1-yl]-5-methylpyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=C1C)=CN=C1N(CC1)CCN1CC1CC1 MRAHXQIWSUTRMV-UHFFFAOYSA-N 0.000 claims 1
• LJWLAGCGLRQAKD-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-[6-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=N1)=CC=C1N(CC1)CCC1CN1CCCC1 LJWLAGCGLRQAKD-UHFFFAOYSA-N 0.000 claims 1
• RDILVZIOIRILQV-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-spiro[1,3-dioxolane-2,6'-7,8-dihydro-5h-quinoline]-3'-yl-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=C1C2)=CN=C1CCC12OCCO1 RDILVZIOIRILQV-UHFFFAOYSA-N 0.000 claims 1
• UEWDGNZVBNJGNX-UHFFFAOYSA-N 1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-5-n-[5-methyl-6-(4-pyrrolidin-1-ylpiperidin-1-yl)pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N1N=C(N)N=C1NC(C=C1C)=CN=C1N(CC1)CCC1N1CCCC1 UEWDGNZVBNJGNX-UHFFFAOYSA-N 0.000 claims 1
• ULNRKDAJCNVIHR-UHFFFAOYSA-N 1-(6,7-dimethoxyquinazolin-4-yl)-3-n-[2-(4-pyrrolidin-1-ylpiperidin-1-yl)pyrimidin-5-yl]-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC(C=N1)=CN=C1N(CC1)CCC1N1CCCC1 ULNRKDAJCNVIHR-UHFFFAOYSA-N 0.000 claims 1
• XSBHBXJPXDJWDE-UHFFFAOYSA-N 1-(6,7-dimethoxyquinazolin-4-yl)-3-n-[2-[4-(piperidin-1-ylmethyl)piperidin-1-yl]pyrimidin-5-yl]-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC(C=N1)=CN=C1N(CC1)CCC1CN1CCCCC1 XSBHBXJPXDJWDE-UHFFFAOYSA-N 0.000 claims 1
• BMTHCVKOIUTUAN-UHFFFAOYSA-N 1-(6,7-dimethoxyquinazolin-4-yl)-3-n-[5-methyl-6-(4-pyrrolidin-1-ylpiperidin-1-yl)pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC(C=C1C)=CN=C1N(CC1)CCC1N1CCCC1 BMTHCVKOIUTUAN-UHFFFAOYSA-N 0.000 claims 1
• WSIXCPKNQXRDCL-UHFFFAOYSA-N 1-(6,7-dimethoxyquinazolin-4-yl)-3-n-[6-(3-piperidin-1-ylprop-1-enyl)pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC(C=N1)=CC=C1C=CCN1CCCCC1 WSIXCPKNQXRDCL-UHFFFAOYSA-N 0.000 claims 1
• FWLSDICWESUSSU-UHFFFAOYSA-N 1-(6,7-dimethoxyquinazolin-4-yl)-3-n-[6-(4-piperidin-1-ylpiperidin-1-yl)pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC(C=N1)=CC=C1N(CC1)CCC1N1CCCCC1 FWLSDICWESUSSU-UHFFFAOYSA-N 0.000 claims 1
• BEAPWQPYZPDNAI-UHFFFAOYSA-N 1-(6,7-dimethoxyquinazolin-4-yl)-3-n-[6-(4-pyrrolidin-1-ylpiperidin-1-yl)pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC(C=N1)=CC=C1N(CC1)CCC1N1CCCC1 BEAPWQPYZPDNAI-UHFFFAOYSA-N 0.000 claims 1
• UAYXYTMCWUHHLX-UHFFFAOYSA-N 1-(6,7-dimethoxyquinazolin-4-yl)-3-n-[6-[3-(4-piperidin-1-ylpiperidin-1-yl)prop-1-enyl]pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC(C=N1)=CC=C1C=CCN(CC1)CCC1N1CCCCC1 UAYXYTMCWUHHLX-UHFFFAOYSA-N 0.000 claims 1
• LNZWXPRLORWMIK-UHFFFAOYSA-N 1-(6,7-dimethoxyquinazolin-4-yl)-3-n-[6-[3-(4-propan-2-ylpiperazin-1-yl)prop-1-enyl]pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC(C=N1)=CC=C1C=CCN1CCN(C(C)C)CC1 LNZWXPRLORWMIK-UHFFFAOYSA-N 0.000 claims 1
• NTVIWUVDHRGHQK-UHFFFAOYSA-N 1-(6,7-dimethoxyquinazolin-4-yl)-3-n-[6-[3-(4-pyrrolidin-1-ylpiperidin-1-yl)prop-1-enyl]pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC(C=N1)=CC=C1C=CCN(CC1)CCC1N1CCCC1 NTVIWUVDHRGHQK-UHFFFAOYSA-N 0.000 claims 1
• YNDFFIDXJGKHOK-UHFFFAOYSA-N 1-(6,7-dimethoxyquinazolin-4-yl)-3-n-[6-[3-[3-(dimethylamino)pyrrolidin-1-yl]prop-1-enyl]pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC(C=N1)=CC=C1C=CCN1CCC(N(C)C)C1 YNDFFIDXJGKHOK-UHFFFAOYSA-N 0.000 claims 1
• XYWYXFYTBXSZED-UHFFFAOYSA-N 1-(6,7-dimethoxyquinazolin-4-yl)-3-n-[6-[3-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]prop-1-enyl]pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC(C=N1)=CC=C1C=CCN(CC1)CCC1N1CCN(C)CC1 XYWYXFYTBXSZED-UHFFFAOYSA-N 0.000 claims 1
• MUCJTZXTUBBCLP-UHFFFAOYSA-N 1-(6,7-dimethoxyquinazolin-4-yl)-3-n-[6-[3-[4-(dimethylamino)piperidin-1-yl]prop-1-enyl]pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC(C=N1)=CC=C1C=CCN1CCC(N(C)C)CC1 MUCJTZXTUBBCLP-UHFFFAOYSA-N 0.000 claims 1
• CZRPGAIKQRBQFR-UHFFFAOYSA-N 1-(6,7-dimethoxyquinazolin-4-yl)-3-n-[6-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC(C=N1)=CC=C1N(CC1)CCC1CN1CCCC1 CZRPGAIKQRBQFR-UHFFFAOYSA-N 0.000 claims 1
• XXDWPJATMHZZOJ-UHFFFAOYSA-N 1-(6-chloroquinazolin-4-yl)-3-n-[2-(pyrrolidin-1-ylmethyl)-1,3-benzoxazol-5-yl]-1,2,4-triazole-3,5-diamine Chemical compound N=1N(C=2C3=CC(Cl)=CC=C3N=CN=2)C(N)=NC=1NC(C=C1N=2)=CC=C1OC=2CN1CCCC1 XXDWPJATMHZZOJ-UHFFFAOYSA-N 0.000 claims 1
• QXYSOIGTSOXRDX-UHFFFAOYSA-N 1-(6-fluoroquinazolin-4-yl)-3-n-[5-methyl-6-(4-pyrrolidin-1-ylpiperidin-1-yl)pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound CC1=CC(NC2=NN(C(N)=N2)C=2C3=CC(F)=CC=C3N=CN=2)=CN=C1N(CC1)CCC1N1CCCC1 QXYSOIGTSOXRDX-UHFFFAOYSA-N 0.000 claims 1
• KBNVQOBEUSBPGM-UHFFFAOYSA-N 1-(7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-(7-pyrrolidin-1-yl-6,7,8,9-tetrahydro-5h-cyclohepta[b]pyridin-3-yl)-1,2,4-triazole-3,5-diamine Chemical compound N1=CN=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=C1CC2)=CN=C1CCC2N1CCCC1 KBNVQOBEUSBPGM-UHFFFAOYSA-N 0.000 claims 1
• DDQWTKSOVYTDPH-UHFFFAOYSA-N 1-(7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-[6-(3-pyrrolidin-1-ylprop-1-enyl)pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound N1=CN=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=N1)=CC=C1C=CCN1CCCC1 DDQWTKSOVYTDPH-UHFFFAOYSA-N 0.000 claims 1
• MZFZRQOOJVTZRE-UHFFFAOYSA-N 1-(7-methylthieno[3,2-d]pyrimidin-4-yl)-3-n-[6-[3-(4-propan-2-ylpiperazin-1-yl)prop-1-enyl]pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound C1CN(C(C)C)CCN1CC=CC(N=C1)=CC=C1NC1=NN(C=2C=3SC=C(C)C=3N=CN=2)C(N)=N1 MZFZRQOOJVTZRE-UHFFFAOYSA-N 0.000 claims 1
• XXQCIQWFLCWNKU-UHFFFAOYSA-N 1-[3-[[5-amino-1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazol-3-yl]amino]-7,8-dihydro-5h-1,6-naphthyridin-6-yl]-2-(dimethylamino)ethanone Chemical compound C1=C2CN(C(=O)CN(C)C)CCC2=NC=C1NC(=N1)N=C(N)N1C1=NC(Cl)=NC2=C1SC=C2C XXQCIQWFLCWNKU-UHFFFAOYSA-N 0.000 claims 1
• PEWINDSPAVKYAL-UHFFFAOYSA-N 1-furo[3,2-c]pyridin-4-yl-3-n-[5-methyl-6-(4-pyrrolidin-1-ylpiperidin-1-yl)pyridin-3-yl]-1,2,4-triazole-3,5-diamine Chemical compound CC1=CC(NC2=NN(C(N)=N2)C=2C=3C=COC=3C=CN=2)=CN=C1N(CC1)CCC1N1CCCC1 PEWINDSPAVKYAL-UHFFFAOYSA-N 0.000 claims 1
• PVCGZICKHDTJAS-UHFFFAOYSA-N 1-isoquinolin-1-yl-3-n-[2-(pyrrolidin-1-ylmethyl)-1,3-benzoxazol-5-yl]-1,2,4-triazole-3,5-diamine Chemical compound N=1N(C=2C3=CC=CC=C3C=CN=2)C(N)=NC=1NC(C=C1N=2)=CC=C1OC=2CN1CCCC1 PVCGZICKHDTJAS-UHFFFAOYSA-N 0.000 claims 1
• RARVFNHZCRECNA-UHFFFAOYSA-N 3-n-(6-benzyl-7,8-dihydro-5h-1,6-naphthyridin-3-yl)-1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=C1C2)=CN=C1CCN2CC1=CC=CC=C1 RARVFNHZCRECNA-UHFFFAOYSA-N 0.000 claims 1
• XLFUXAZAZPLMRY-UHFFFAOYSA-N 3-n-(6-bromopyridin-3-yl)-1-(6,7-dimethoxyquinazolin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC1=CC=C(Br)N=C1 XLFUXAZAZPLMRY-UHFFFAOYSA-N 0.000 claims 1
• VZJOGODJBKWMIF-UHFFFAOYSA-N 3-n-(6-bromopyridin-3-yl)-1-(7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound N1=CN=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC1=CC=C(Br)N=C1 VZJOGODJBKWMIF-UHFFFAOYSA-N 0.000 claims 1
• VPVCUVZBSUZTJT-UHFFFAOYSA-N 3-n-(6-cyclopentyl-7,8-dihydro-5h-1,6-naphthyridin-3-yl)-1-(7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound N1=CN=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=C1C2)=CN=C1CCN2C1CCCC1 VPVCUVZBSUZTJT-UHFFFAOYSA-N 0.000 claims 1
• QIKVYTOSVDYHGV-UHFFFAOYSA-N 3-n-(7-cyclopentyl-5,6,8,9-tetrahydropyrido[2,3-d]azepin-3-yl)-1-(6,7-dimethoxyquinazolin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC(C=C1CC2)=CN=C1CCN2C1CCCC1 QIKVYTOSVDYHGV-UHFFFAOYSA-N 0.000 claims 1
• OCENWTPHGQLCGO-UHFFFAOYSA-N 3-n-[5-amino-1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazol-3-yl]-5,6,7,8-tetrahydroquinoline-3,6-diamine Chemical compound C1CC(N)CC2=CC(NC3=NN(C(=N3)N)C3=C4SC=C(C4=NC(Cl)=N3)C)=CN=C21 OCENWTPHGQLCGO-UHFFFAOYSA-N 0.000 claims 1
• KHRYCQGPQJHWLV-UHFFFAOYSA-N 3-n-[5-amino-1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazol-3-yl]-6-(3-bicyclo[2.2.1]heptanyl)-5,6,7,8-tetrahydroquinoline-2,3-diamine Chemical compound C1C(C2C3CCC(C3)C2)CCC(N=C2N)=C1C=C2NC(N=C1N)=NN1C1=C2SC=C(C)C2=NC(Cl)=N1 KHRYCQGPQJHWLV-UHFFFAOYSA-N 0.000 claims 1
• HLTVUFFSYOWGEK-UHFFFAOYSA-N 3-n-[5-amino-1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazol-3-yl]-6-n-(1-methylpiperidin-4-yl)-5,6,7,8-tetrahydroquinoline-3,6-diamine Chemical compound C1CN(C)CCC1NC1CC2=CC(NC3=NN(C(N)=N3)C=3C=4SC=C(C)C=4N=C(Cl)N=3)=CN=C2CC1 HLTVUFFSYOWGEK-UHFFFAOYSA-N 0.000 claims 1
• QDGXQAZPANHFQZ-UHFFFAOYSA-N 3-n-[5-amino-1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazol-3-yl]-6-n-cyclohexyl-5,6,7,8-tetrahydroquinoline-3,6-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=C1C2)=CN=C1CCC2NC1CCCCC1 QDGXQAZPANHFQZ-UHFFFAOYSA-N 0.000 claims 1
• IVTPXGKKEIKMLV-UHFFFAOYSA-N 3-n-[5-amino-1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazol-3-yl]-6-n-cyclopentyl-5,6,7,8-tetrahydroquinoline-3,6-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=C1C2)=CN=C1CCC2NC1CCCC1 IVTPXGKKEIKMLV-UHFFFAOYSA-N 0.000 claims 1
• CVJCSJWHJYHENE-UHFFFAOYSA-N 3-n-[5-amino-1-(7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazol-3-yl]-6-n-(1-methylpiperidin-4-yl)-5,6,7,8-tetrahydroquinoline-3,6-diamine Chemical compound C1CN(C)CCC1NC1CC2=CC(NC3=NN(C(N)=N3)C=3C=4SC=C(C)C=4N=CN=3)=CN=C2CC1 CVJCSJWHJYHENE-UHFFFAOYSA-N 0.000 claims 1
• MANZRMPIGJYTAM-UHFFFAOYSA-N 3-n-[5-amino-1-(7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazol-3-yl]-6-n-cyclopentyl-5,6,7,8-tetrahydroquinoline-3,6-diamine Chemical compound N1=CN=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=C1C2)=CN=C1CCC2NC1CCCC1 MANZRMPIGJYTAM-UHFFFAOYSA-N 0.000 claims 1
• YZSQHSFTMIMDGT-UHFFFAOYSA-N 3-n-[5-methyl-6-(4-pyrrolidin-1-ylpiperidin-1-yl)pyridin-3-yl]-1-(2-methylquinazolin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound C=12C=CC=CC2=NC(C)=NC=1N(C(=N1)N)N=C1NC(C=C1C)=CN=C1N(CC1)CCC1N1CCCC1 YZSQHSFTMIMDGT-UHFFFAOYSA-N 0.000 claims 1
• LZFAFFGAFUYSFW-UHFFFAOYSA-N 3-n-[5-methyl-6-(4-pyrrolidin-1-ylpiperidin-1-yl)pyridin-3-yl]-1-(6-phenylpyrimidin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound C=1N=C(N2CCC(CC2)N2CCCC2)C(C)=CC=1NC(=N1)N=C(N)N1C(N=CN=1)=CC=1C1=CC=CC=C1 LZFAFFGAFUYSFW-UHFFFAOYSA-N 0.000 claims 1
• NMGQAQJFYKOHGZ-UHFFFAOYSA-N 3-n-[5-methyl-6-(4-pyrrolidin-1-ylpiperidin-1-yl)pyridin-3-yl]-1-phenanthridin-6-yl-1,2,4-triazole-3,5-diamine Chemical compound CC1=CC(NC2=NN(C(N)=N2)C=2C3=CC=CC=C3C3=CC=CC=C3N=2)=CN=C1N(CC1)CCC1N1CCCC1 NMGQAQJFYKOHGZ-UHFFFAOYSA-N 0.000 claims 1
• RPABPCZXGRYRDY-UHFFFAOYSA-N 3-n-[6-(3-bicyclo[2.2.1]heptanyl)-7,8-dihydro-5h-1,6-naphthyridin-3-yl]-1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=C1C2)=CN=C1CCN2C1C(C2)CCC2C1 RPABPCZXGRYRDY-UHFFFAOYSA-N 0.000 claims 1
• FBPLYLVFMMPBQR-UHFFFAOYSA-N 3-n-[6-(4-cyclopentyl-1,4-diazepan-1-yl)pyridin-3-yl]-1-(6,7-dimethoxyquinazolin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC(C=N1)=CC=C1N(CC1)CCCN1C1CCCC1 FBPLYLVFMMPBQR-UHFFFAOYSA-N 0.000 claims 1
• ASWPQGIBBVOHPZ-INIZCTEOSA-N 3-n-[6-[(3s)-4-(cyclopropylmethyl)-3-methylpiperazin-1-yl]pyridin-3-yl]-1-(6,7-dimethoxyquinazolin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC(C=N1)=CC=C1N(C[C@@H]1C)CCN1CC1CC1 ASWPQGIBBVOHPZ-INIZCTEOSA-N 0.000 claims 1
• ODTZSCMUQHPIPC-HNNXBMFYSA-N 3-n-[6-[(3s)-4-(cyclopropylmethyl)-3-methylpiperazin-1-yl]pyridin-3-yl]-1-(7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound C([C@@H]1C)N(C=2N=CC(NC3=NN(C(N)=N3)C=3C=4SC=C(C)C=4N=CN=3)=CC=2)CCN1CC1CC1 ODTZSCMUQHPIPC-HNNXBMFYSA-N 0.000 claims 1
• YQBRDGJLCFPLEY-JTJHWIPRSA-N 3-n-[6-[(3s)-4-[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]-3-methylpiperazin-1-yl]-5-methylpyridin-3-yl]-1-(7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])([C@H](C1)C)CCN1C(C(=C1)C)=NC=C1NC(=N1)N=C(N)N1C1=NC=NC2=C1SC=C2C YQBRDGJLCFPLEY-JTJHWIPRSA-N 0.000 claims 1
• VHGREDURKMTEHO-NNZWXOEDSA-N 3-n-[6-[(3s)-4-[(3s)-3-bicyclo[2.2.1]heptanyl]-3-methylpiperazin-1-yl]-5-methylpyridin-3-yl]-1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound C([C@@H](N(CC1)[C@@H]2C3CCC(C3)C2)C)N1C(C(=C1)C)=NC=C1NC(=N1)N=C(N)N1C1=NC(Cl)=NC2=C1SC=C2C VHGREDURKMTEHO-NNZWXOEDSA-N 0.000 claims 1
• SLIFFOFIRQCBER-RJPLPAITSA-N 3-n-[6-[(3s)-4-[(3s)-3-bicyclo[2.2.1]heptanyl]-3-methylpiperazin-1-yl]-5-methylpyridin-3-yl]-1-thieno[3,2-d]pyrimidin-4-yl-1,2,4-triazole-3,5-diamine Chemical compound C([C@@H](N(CC1)[C@@H]2C3CCC(C3)C2)C)N1C(C(=C1)C)=NC=C1NC(=N1)N=C(N)N1C1=NC=NC2=C1SC=C2 SLIFFOFIRQCBER-RJPLPAITSA-N 0.000 claims 1
• AGTXUSZAASMJMA-UHFFFAOYSA-N 3-n-[6-[1-(3-bicyclo[2.2.1]heptanyl)piperidin-4-yl]pyridin-3-yl]-1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=N1)=CC=C1C(CC1)CCN1C1C(C2)CCC2C1 AGTXUSZAASMJMA-UHFFFAOYSA-N 0.000 claims 1
• NBCPDNVLFGOODG-UHFFFAOYSA-N 3-n-[6-[1-(3-bicyclo[2.2.1]heptanyl)piperidin-4-yl]pyridin-3-yl]-1-(7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound N1=CN=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=N1)=CC=C1C(CC1)CCN1C1C(C2)CCC2C1 NBCPDNVLFGOODG-UHFFFAOYSA-N 0.000 claims 1
• VDQIHMZMVRCPCP-UHFFFAOYSA-N 3-n-[6-[2-(diethylaminomethyl)pyrrolidin-1-yl]pyridin-3-yl]-1-(6,7-dimethoxyquinazolin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound CCN(CC)CC1CCCN1C(N=C1)=CC=C1NC1=NN(C=2C3=CC(OC)=C(OC)C=C3N=CN=2)C(N)=N1 VDQIHMZMVRCPCP-UHFFFAOYSA-N 0.000 claims 1
• LZVQKPFXHCCQNT-UHFFFAOYSA-N 3-n-[6-[3-(4-cyclopentylpiperazin-1-yl)prop-1-enyl]pyridin-3-yl]-1-(6,7-dimethoxyquinazolin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC(C=N1)=CC=C1C=CCN(CC1)CCN1C1CCCC1 LZVQKPFXHCCQNT-UHFFFAOYSA-N 0.000 claims 1
• YLWDXZGPODUNRE-UHFFFAOYSA-N 3-n-[6-[3-(4-methylpiperazin-1-yl)prop-1-enyl]pyridin-3-yl]-1-(7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound C1CN(C)CCN1CC=CC(N=C1)=CC=C1NC1=NN(C=2C=3SC=C(C)C=3N=CN=2)C(N)=N1 YLWDXZGPODUNRE-UHFFFAOYSA-N 0.000 claims 1
• DXBOAECMPXNJPL-UHFFFAOYSA-N 3-n-[6-[3-(diethylamino)pyrrolidin-1-yl]pyridin-3-yl]-1-(6,7-dimethoxyquinazolin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound C1C(N(CC)CC)CCN1C(N=C1)=CC=C1NC1=NN(C=2C3=CC(OC)=C(OC)C=C3N=CN=2)C(N)=N1 DXBOAECMPXNJPL-UHFFFAOYSA-N 0.000 claims 1
• VASQQTJSFJZLPX-UHFFFAOYSA-N 3-n-[6-[3-[3-(diethylamino)pyrrolidin-1-yl]prop-1-enyl]pyridin-3-yl]-1-(6,7-dimethoxyquinazolin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound C1C(N(CC)CC)CCN1CC=CC(N=C1)=CC=C1NC1=NN(C=2C3=CC(OC)=C(OC)C=C3N=CN=2)C(N)=N1 VASQQTJSFJZLPX-UHFFFAOYSA-N 0.000 claims 1
• MZJNILCHJPLWHK-UHFFFAOYSA-N 3-n-[6-[3-[3-(diethylamino)pyrrolidin-1-yl]prop-1-enyl]pyridin-3-yl]-1-(7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound C1C(N(CC)CC)CCN1CC=CC(N=C1)=CC=C1NC1=NN(C=2C=3SC=C(C)C=3N=CN=2)C(N)=N1 MZJNILCHJPLWHK-UHFFFAOYSA-N 0.000 claims 1
• HPRDLBQRXLEPHE-UHFFFAOYSA-N 3-n-[6-[3-[3-(dimethylamino)pyrrolidin-1-yl]prop-1-enyl]pyridin-3-yl]-1-(7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound C1C(N(C)C)CCN1CC=CC(N=C1)=CC=C1NC1=NN(C=2C=3SC=C(C)C=3N=CN=2)C(N)=N1 HPRDLBQRXLEPHE-UHFFFAOYSA-N 0.000 claims 1
• TXRZXLPLYFWLGS-UHFFFAOYSA-N 3-n-[6-[4-(3-bicyclo[2.2.1]heptanyl)-1,4-diazepan-1-yl]pyridin-3-yl]-1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=N1)=CC=C1N(CC1)CCCN1C1C(C2)CCC2C1 TXRZXLPLYFWLGS-UHFFFAOYSA-N 0.000 claims 1
• HNNAJWPDLMIYOJ-UHFFFAOYSA-N 3-n-[6-[4-(3-bicyclo[2.2.1]heptanyl)-1,4-diazepan-1-yl]pyridin-3-yl]-1-(6,7-dimethoxyquinazolin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC(C=N1)=CC=C1N(CC1)CCCN1C1C(C2)CCC2C1 HNNAJWPDLMIYOJ-UHFFFAOYSA-N 0.000 claims 1
• LRRZKAYPGFPVSE-UHFFFAOYSA-N 3-n-[6-[4-(3-bicyclo[2.2.1]heptanyl)piperazin-1-yl]-5-methylpyridin-3-yl]-1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=C1C)=CN=C1N(CC1)CCN1C1C(C2)CCC2C1 LRRZKAYPGFPVSE-UHFFFAOYSA-N 0.000 claims 1
• GQONIVGBMPPYLT-UHFFFAOYSA-N 3-n-[6-[4-(3-bicyclo[2.2.1]heptanyl)piperazin-1-yl]-5-methylpyridin-3-yl]-1-(7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound N1=CN=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=C1C)=CN=C1N(CC1)CCN1C1C(C2)CCC2C1 GQONIVGBMPPYLT-UHFFFAOYSA-N 0.000 claims 1
• GJGJAZOOIBLDRR-UHFFFAOYSA-N 3-n-[6-[4-(3-bicyclo[2.2.1]heptanyl)piperazin-1-yl]pyridin-3-yl]-1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=N1)=CC=C1N(CC1)CCN1C1C(C2)CCC2C1 GJGJAZOOIBLDRR-UHFFFAOYSA-N 0.000 claims 1
• XINQNGHGVUPKFM-UHFFFAOYSA-N 3-n-[6-[4-(3-bicyclo[2.2.1]heptanyl)piperazin-1-yl]pyridin-3-yl]-1-(6,7-dimethoxyquinazolin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound C=12C=C(OC)C(OC)=CC2=NC=NC=1N(C(=N1)N)N=C1NC(C=N1)=CC=C1N(CC1)CCN1C1C(C2)CCC2C1 XINQNGHGVUPKFM-UHFFFAOYSA-N 0.000 claims 1
• WZWITAZHJGPHDV-UHFFFAOYSA-N 3-n-[6-[4-(azepan-1-yl)piperidin-1-yl]pyridin-3-yl]-1-(2-chloro-7-methylthieno[3,2-d]pyrimidin-4-yl)-1,2,4-triazole-3,5-diamine Chemical compound N1=C(Cl)N=C2C(C)=CSC2=C1N(C(=N1)N)N=C1NC(C=N1)=CC=C1N(CC1)CCC1N1CCCCCC1 WZWITAZHJGPHDV-UHFFFAOYSA-N 0.000 claims 1
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