SI2945632T1 - HETEROBICYL-SUBSTITUTED- (1,2,4) TRIAZOLO (1,5-C) KINAZOLIN-5-AMIN COMPOUNDS SUITABLE FOR TREATMENT AND PREVENTION OF THE EMISSION OF THE CENTRAL LIVING SYSTEM - Google Patents
HETEROBICYL-SUBSTITUTED- (1,2,4) TRIAZOLO (1,5-C) KINAZOLIN-5-AMIN COMPOUNDS SUITABLE FOR TREATMENT AND PREVENTION OF THE EMISSION OF THE CENTRAL LIVING SYSTEM Download PDFInfo
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- SI2945632T1 SI2945632T1 SI201330980T SI201330980T SI2945632T1 SI 2945632 T1 SI2945632 T1 SI 2945632T1 SI 201330980 T SI201330980 T SI 201330980T SI 201330980 T SI201330980 T SI 201330980T SI 2945632 T1 SI2945632 T1 SI 2945632T1
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- SI
- Slovenia
- Prior art keywords
- triazolo
- amine
- methoxy
- quinazolin
- ethyl
- Prior art date
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- 208000015114 central nervous system disease Diseases 0.000 title claims 2
- 230000002265 prevention Effects 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract 43
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 6
- 208000012902 Nervous system disease Diseases 0.000 claims abstract 3
- -1 morpholino, phenyl Chemical group 0.000 claims 67
- KWHDQPVGKVPPPS-UHFFFAOYSA-N quinazolin-5-amine Chemical compound C1=NC=C2C(N)=CC=CC2=N1 KWHDQPVGKVPPPS-UHFFFAOYSA-N 0.000 claims 31
- 150000003839 salts Chemical class 0.000 claims 27
- XYVBVIVKSJMEIW-UHFFFAOYSA-N C1=CC=C2C3=CN=NN3C(N)=NC2=C1 Chemical compound C1=CC=C2C3=CN=NN3C(N)=NC2=C1 XYVBVIVKSJMEIW-UHFFFAOYSA-N 0.000 claims 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 8
- 229910052799 carbon Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- FADASXSDYBZQQS-UHFFFAOYSA-N 2-[2-(2-cyclopropyl-4,6-dihydropyrrolo[3,4-d][1,3]oxazol-5-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(CC=1O2)CC=1N=C2C1CC1 FADASXSDYBZQQS-UHFFFAOYSA-N 0.000 claims 2
- DOXTUZCGFXTMIQ-UHFFFAOYSA-N 2-[2-(2-cyclopropyl-4,6-dihydropyrrolo[3,4-d][1,3]thiazol-5-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(CC=1S2)CC=1N=C2C1CC1 DOXTUZCGFXTMIQ-UHFFFAOYSA-N 0.000 claims 2
- JFYIJBCBFSEIOY-SNVBAGLBSA-N 7-methoxy-2-[(2r)-2-(2-methyl-4,6-dihydropyrrolo[3,4-d][1,3]oxazol-5-yl)propyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C12=NC(C[C@@H](C)N3CC=4OC(C)=NC=4C3)=NN2C(N)=NC2=C1C=CC=C2OC JFYIJBCBFSEIOY-SNVBAGLBSA-N 0.000 claims 2
- YMQFNHHVKFBEMO-NSHDSACASA-N 7-methoxy-2-[(2s)-2-(2-methyl-6,7-dihydro-4h-[1,3]oxazolo[4,5-c]pyridin-5-yl)propyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1N([C@@H](C)CC=2N=C3C=4C=CC=C(C=4N=C(N)N3N=2)OC)CCC2=C1N=C(C)O2 YMQFNHHVKFBEMO-NSHDSACASA-N 0.000 claims 2
- DWMBNNGZDHHEAW-UHFFFAOYSA-N 7-methoxy-2-[2-(1-methyl-4,6-dihydropyrrolo[3,4-c]pyrazol-5-yl)ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C12=NC(CCN3CC=4N(C)N=CC=4C3)=NN2C(N)=NC2=C1C=CC=C2OC DWMBNNGZDHHEAW-UHFFFAOYSA-N 0.000 claims 2
- XBUZINXHGBWRAB-UHFFFAOYSA-N 7-methoxy-2-[2-(2-propan-2-yl-4,6-dihydropyrrolo[3,4-d][1,3]thiazol-5-yl)ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C12=NC(CCN3CC=4SC(=NC=4C3)C(C)C)=NN2C(N)=NC2=C1C=CC=C2OC XBUZINXHGBWRAB-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 101001109792 Homo sapiens Pro-neuregulin-2, membrane-bound isoform Proteins 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 102100022668 Pro-neuregulin-2, membrane-bound isoform Human genes 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- YMNCVDUDIBNLKT-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzoxazin-4-ylmethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1COC2=CC=CC=C2N1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 YMNCVDUDIBNLKT-UHFFFAOYSA-N 0.000 claims 1
- RELRPISMEQUONA-UHFFFAOYSA-N 2-(3,4-dihydro-1h-isoquinolin-2-ylmethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=CC=CC=C2CN1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 RELRPISMEQUONA-UHFFFAOYSA-N 0.000 claims 1
- OBTFFMMVGIVMAN-UHFFFAOYSA-N 2-(3,4-dihydro-2h-1,5-naphthyridin-1-ylmethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CCC2=NC=CC=C2N1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 OBTFFMMVGIVMAN-UHFFFAOYSA-N 0.000 claims 1
- UOFOVOQBUUOJBZ-UHFFFAOYSA-N 2-(3,4-dihydro-2h-1,6-naphthyridin-1-ylmethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CCC2=CN=CC=C2N1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 UOFOVOQBUUOJBZ-UHFFFAOYSA-N 0.000 claims 1
- CUSAMCOAFLUXBG-UHFFFAOYSA-N 2-(3,4-dihydro-2h-1,7-naphthyridin-1-ylmethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CCC2=CC=NC=C2N1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 CUSAMCOAFLUXBG-UHFFFAOYSA-N 0.000 claims 1
- CYAWJODONYWGFZ-UHFFFAOYSA-N 2-(3,4-dihydro-2h-1,8-naphthyridin-1-ylmethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CCC2=CC=CN=C2N1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 CYAWJODONYWGFZ-UHFFFAOYSA-N 0.000 claims 1
- JFWZFOXJMJVYFY-UHFFFAOYSA-N 2-(3,4-dihydro-2h-quinolin-1-ylmethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CCC2=CC=CC=C2N1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 JFWZFOXJMJVYFY-UHFFFAOYSA-N 0.000 claims 1
- DKTFRTHXQMXJFX-UHFFFAOYSA-N 2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-ylmethyl)-7-(methoxymethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CN=C2CN1CC1=NN(C(N)=NC=2C(COC)=CC=CC=22)C2=N1 DKTFRTHXQMXJFX-UHFFFAOYSA-N 0.000 claims 1
- WQERTYMYRDKADL-UHFFFAOYSA-N 2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-ylmethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CN=C2CN1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 WQERTYMYRDKADL-UHFFFAOYSA-N 0.000 claims 1
- VPRCEKNRVFMUCE-UHFFFAOYSA-N 2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-ylmethyl)-9-fluoro-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CN=C2CN1CC1=NN(C(N)=NC=2C(OC)=CC(F)=CC=22)C2=N1 VPRCEKNRVFMUCE-UHFFFAOYSA-N 0.000 claims 1
- RBOUFUVNLOCBAP-UHFFFAOYSA-N 2-(5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)-1-(1,2,4,5-tetrahydro-3-benzazepin-3-yl)ethanone Chemical compound C1CC2=CC=CC=C2CCN1C(=O)CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 RBOUFUVNLOCBAP-UHFFFAOYSA-N 0.000 claims 1
- URLJCVGMSXAGAX-UHFFFAOYSA-N 2-(6,8-dihydro-5h-1,7-naphthyridin-7-ylmethyl)-7-(2-fluoroethoxy)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=CC=CN=C2CN1CC1=NN2C(N)=NC3=C(OCCF)C=CC=C3C2=N1 URLJCVGMSXAGAX-UHFFFAOYSA-N 0.000 claims 1
- MZSVACFTVDTHHR-UHFFFAOYSA-N 2-(6,8-dihydro-5h-1,7-naphthyridin-7-ylmethyl)-7-(methoxymethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=CC=CN=C2CN1CC1=NN(C(N)=NC=2C(COC)=CC=CC=22)C2=N1 MZSVACFTVDTHHR-UHFFFAOYSA-N 0.000 claims 1
- ZJQDAQQPAJWURN-UHFFFAOYSA-N 2-(6,8-dihydro-5h-1,7-naphthyridin-7-ylmethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=CC=CN=C2CN1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 ZJQDAQQPAJWURN-UHFFFAOYSA-N 0.000 claims 1
- OZXWIMCFQCJAKG-UHFFFAOYSA-N 2-(6,8-dihydro-5h-1,7-naphthyridin-7-ylmethyl)-7-methyl-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=CC=CN=C2CN1CC1=NN(C(N)=NC=2C(C)=CC=CC=22)C2=N1 OZXWIMCFQCJAKG-UHFFFAOYSA-N 0.000 claims 1
- BLCGYEQCSVWBHO-UHFFFAOYSA-N 2-(6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-ylmethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=CN=CN=C2CN1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 BLCGYEQCSVWBHO-UHFFFAOYSA-N 0.000 claims 1
- IXYJBAWRRAIICU-UHFFFAOYSA-N 2-(7,8-dihydro-5h-pyrido[3,4-b]pyrazin-6-ylmethyl)-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=NC=CN=C2CN1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 IXYJBAWRRAIICU-UHFFFAOYSA-N 0.000 claims 1
- IMFRSLCSETUKEQ-UHFFFAOYSA-N 2-[(2-chloro-5,6,7,8-tetrahydropyrido[2,3-b]azepin-9-yl)methyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CCCC2=CC=C(Cl)N=C2N1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 IMFRSLCSETUKEQ-UHFFFAOYSA-N 0.000 claims 1
- JCCWPSZKDFSBEG-UHFFFAOYSA-N 2-[(2-chloro-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)methyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=C(Cl)N=C2CN1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 JCCWPSZKDFSBEG-UHFFFAOYSA-N 0.000 claims 1
- ZEWMMZAULZBMFG-GFCCVEGCSA-N 2-[(2r)-2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)propyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CN=C2CN1[C@H](C)CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 ZEWMMZAULZBMFG-GFCCVEGCSA-N 0.000 claims 1
- XGCOILUHPLJBIN-HNNXBMFYSA-N 2-[(2s)-2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)-3,3,3-trifluoropropyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CN=C2CN1[C@H](C(F)(F)F)CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 XGCOILUHPLJBIN-HNNXBMFYSA-N 0.000 claims 1
- ZEWMMZAULZBMFG-LBPRGKRZSA-N 2-[(2s)-2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)propyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CN=C2CN1[C@@H](C)CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 ZEWMMZAULZBMFG-LBPRGKRZSA-N 0.000 claims 1
- MKZFTGMGCXDQOB-UHFFFAOYSA-N 2-[(3-ethyl-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)methyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C12=CC=CC(OC)=C2N=C(N)N2C1=NC(CN1CC3=NN=C(N3CC1)CC)=N2 MKZFTGMGCXDQOB-UHFFFAOYSA-N 0.000 claims 1
- UTGJJHDTWOLYKQ-UHFFFAOYSA-N 2-[(4,4-dimethyl-1,3-dihydroisoquinolin-2-yl)methyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CC=C2C(C)(C)CN1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 UTGJJHDTWOLYKQ-UHFFFAOYSA-N 0.000 claims 1
- OKFPMXKHUFMHGL-UHFFFAOYSA-N 2-[(4-bromo-6,8-dihydro-5h-1,7-naphthyridin-7-yl)methyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=C(Br)C=CN=C2CN1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 OKFPMXKHUFMHGL-UHFFFAOYSA-N 0.000 claims 1
- QRUPAYMJIOJTSY-UHFFFAOYSA-N 2-[(5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)methyl]-3,4-dihydro-1h-isoquinoline-6-carbonitrile Chemical compound C1CC2=CC(C#N)=CC=C2CN1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 QRUPAYMJIOJTSY-UHFFFAOYSA-N 0.000 claims 1
- ONJPAYWCXAUDRZ-UHFFFAOYSA-N 2-[(5-bromo-2,3-dihydropyrrolo[2,3-b]pyridin-1-yl)methyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=CC(Br)=CN=C2N1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 ONJPAYWCXAUDRZ-UHFFFAOYSA-N 0.000 claims 1
- FSACKJCTUKOPDM-UHFFFAOYSA-N 2-[(5-fluoro-1,3-dihydroisoindol-2-yl)methyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=C(F)C=C2CN1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 FSACKJCTUKOPDM-UHFFFAOYSA-N 0.000 claims 1
- QTGJDGVUDVQCDB-UHFFFAOYSA-N 2-[(6-fluoro-3,4-dihydro-1h-isoquinolin-2-yl)methyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=CC(F)=CC=C2CN1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 QTGJDGVUDVQCDB-UHFFFAOYSA-N 0.000 claims 1
- BEXQCHBDKACGMM-UHFFFAOYSA-N 2-[(7-chloro-4-methyl-3,5-dihydro-2h-1,4-benzodiazepin-1-yl)methyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CN(C)CC2=CC(Cl)=CC=C2N1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 BEXQCHBDKACGMM-UHFFFAOYSA-N 0.000 claims 1
- CMYMSVKANRPLAL-UHFFFAOYSA-N 2-[2-(1,3-dihydroisoindol-2-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CC=C2CN1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 CMYMSVKANRPLAL-UHFFFAOYSA-N 0.000 claims 1
- YARPDTVXFOWVDP-UHFFFAOYSA-N 2-[2-(1-cyclopropyl-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(C1)CCC2=C1C=NN2C1CC1 YARPDTVXFOWVDP-UHFFFAOYSA-N 0.000 claims 1
- RMFYXMSHDRFFAK-UHFFFAOYSA-N 2-[2-(2,3-dihydropyrrolo[2,3-b]pyridin-1-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=CC=CN=C2N1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 RMFYXMSHDRFFAK-UHFFFAOYSA-N 0.000 claims 1
- BGCQSPLUKBWQOY-UHFFFAOYSA-N 2-[2-(2,4-dimethyl-6,7-dihydro-4h-[1,3]oxazolo[5,4-c]pyridin-5-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(C1C)CCC2=C1OC(C)=N2 BGCQSPLUKBWQOY-UHFFFAOYSA-N 0.000 claims 1
- OKPXZZONLATGMY-UHFFFAOYSA-N 2-[2-(2,6-dimethyl-6,7-dihydro-4h-[1,3]oxazolo[5,4-c]pyridin-5-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(C(C1)C)CC2=C1N=C(C)O2 OKPXZZONLATGMY-UHFFFAOYSA-N 0.000 claims 1
- RJCSRPVFXLUKEQ-UHFFFAOYSA-N 2-[2-(2-chloro-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=C(Cl)N=C2CN1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 RJCSRPVFXLUKEQ-UHFFFAOYSA-N 0.000 claims 1
- XZDMDELNCJRQIW-UHFFFAOYSA-N 2-[2-(3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-7-fluoro-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=CC=CC=C2CN1CCC1=NN2C(N)=NC3=C(F)C=CC=C3C2=N1 XZDMDELNCJRQIW-UHFFFAOYSA-N 0.000 claims 1
- WCQBEGSIKMZWHD-UHFFFAOYSA-N 2-[2-(3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-7-methyl-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=CC=CC=C2CN1CCC1=NN(C(N)=NC=2C(C)=CC=CC=22)C2=N1 WCQBEGSIKMZWHD-UHFFFAOYSA-N 0.000 claims 1
- ZNSNBSGWCABDMD-UHFFFAOYSA-N 2-[2-(3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-8-fluoro-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=CC=CC=C2CN1CCC1=NN2C(N)=NC3=CC(F)=CC=C3C2=N1 ZNSNBSGWCABDMD-UHFFFAOYSA-N 0.000 claims 1
- PUXNGPVMNSAZGU-UHFFFAOYSA-N 2-[2-(3,4-dihydro-2h-quinolin-1-yl)ethyl]-7-fluoro-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CCC2=CC=CC=C2N1CCC1=NN2C(N)=NC3=C(F)C=CC=C3C2=N1 PUXNGPVMNSAZGU-UHFFFAOYSA-N 0.000 claims 1
- PDBUJZFZVUIJGM-UHFFFAOYSA-N 2-[2-(3,4-dihydro-2h-quinolin-1-yl)ethyl]-8-fluoro-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CCC2=CC=CC=C2N1CCC1=NN2C(N)=NC3=CC(F)=CC=C3C2=N1 PDBUJZFZVUIJGM-UHFFFAOYSA-N 0.000 claims 1
- XSVDEDCAECIWGS-UHFFFAOYSA-N 2-[2-(3-bromo-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CN2C(Br)=NN=C2CN1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 XSVDEDCAECIWGS-UHFFFAOYSA-N 0.000 claims 1
- ZPDNGTMWCPAAGG-UHFFFAOYSA-N 2-[2-(3-cyclopropyl-1,5,6,7-tetrahydropyrazolo[4,3-b]pyridin-4-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(C1=2)CCCC=2NN=C1C1CC1 ZPDNGTMWCPAAGG-UHFFFAOYSA-N 0.000 claims 1
- LNYAYSXYOXNTNA-UHFFFAOYSA-N 2-[2-(4,4-dimethyl-1,3-dihydroisoquinolin-2-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CC=C2C(C)(C)CN1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 LNYAYSXYOXNTNA-UHFFFAOYSA-N 0.000 claims 1
- ZFWQLSZOQXWTKT-UHFFFAOYSA-N 2-[2-(4-bromo-6,8-dihydro-5h-1,7-naphthyridin-7-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=C(Br)C=CN=C2CN1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 ZFWQLSZOQXWTKT-UHFFFAOYSA-N 0.000 claims 1
- XGCOILUHPLJBIN-UHFFFAOYSA-N 2-[2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)-3,3,3-trifluoropropyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CN=C2CN1C(C(F)(F)F)CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 XGCOILUHPLJBIN-UHFFFAOYSA-N 0.000 claims 1
- XETOLLQLKNPWDJ-UHFFFAOYSA-N 2-[2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)-3-fluoropropyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CN=C2CN1C(CF)CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 XETOLLQLKNPWDJ-UHFFFAOYSA-N 0.000 claims 1
- NSRYTSQDLZQHIR-UHFFFAOYSA-N 2-[2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)butyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CN=C2CN1C(CC)CC1=NN2C(N)=NC3=C(OC)C=CC=C3C2=N1 NSRYTSQDLZQHIR-UHFFFAOYSA-N 0.000 claims 1
- LKYWONRSZBRCNV-UHFFFAOYSA-N 2-[2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)ethyl]-7,8-dimethoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CN=C2CN1CCC1=NN(C(N)=NC=2C3=CC=C(C=2OC)OC)C3=N1 LKYWONRSZBRCNV-UHFFFAOYSA-N 0.000 claims 1
- SGDWJBIBXIPJMK-UHFFFAOYSA-N 2-[2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)ethyl]-7,9-difluoro-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CN=C2CN1CCC1=NN2C(N)=NC3=C(F)C=C(F)C=C3C2=N1 SGDWJBIBXIPJMK-UHFFFAOYSA-N 0.000 claims 1
- UTPWUHZUHWSUJG-UHFFFAOYSA-N 2-[2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)ethyl]-7-fluoro-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CN=C2CN1CCC1=NN2C(N)=NC3=C(F)C=CC=C3C2=N1 UTPWUHZUHWSUJG-UHFFFAOYSA-N 0.000 claims 1
- LRVVXXUIEXAKOP-UHFFFAOYSA-N 2-[2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CN=C2CN1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 LRVVXXUIEXAKOP-UHFFFAOYSA-N 0.000 claims 1
- PWENVIQPTDTKKO-UHFFFAOYSA-N 2-[2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)ethyl]-8,9-difluoro-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CN=C2CN1CCC1=NN2C(N)=NC3=CC(F)=C(F)C=C3C2=N1 PWENVIQPTDTKKO-UHFFFAOYSA-N 0.000 claims 1
- FPQDEOUNGIPEMI-UHFFFAOYSA-N 2-[2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)ethyl]-8-fluoro-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CN=C2CN1CCC1=NN2C(N)=NC3=CC(F)=CC=C3C2=N1 FPQDEOUNGIPEMI-UHFFFAOYSA-N 0.000 claims 1
- KOMHKOZOIPFNGA-UHFFFAOYSA-N 2-[2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)ethyl]-9-fluoro-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CN=C2CN1CCC1=NN(C(N)=NC=2C(OC)=CC(F)=CC=22)C2=N1 KOMHKOZOIPFNGA-UHFFFAOYSA-N 0.000 claims 1
- NWMMVJRLYMRWDP-UHFFFAOYSA-N 2-[2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)pentyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CN=C2CN1C(CCC)CC1=NN2C(N)=NC3=C(OC)C=CC=C3C2=N1 NWMMVJRLYMRWDP-UHFFFAOYSA-N 0.000 claims 1
- ZEWMMZAULZBMFG-UHFFFAOYSA-N 2-[2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)propyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CN=C2CN1C(C)CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 ZEWMMZAULZBMFG-UHFFFAOYSA-N 0.000 claims 1
- UKEBRSFAWHFMQR-UHFFFAOYSA-N 2-[2-(5,7-dihydropyrrolo[3,4-d]pyrimidin-6-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CN=CN=C2CN1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 UKEBRSFAWHFMQR-UHFFFAOYSA-N 0.000 claims 1
- PSGJEOJQZPMKIA-UHFFFAOYSA-N 2-[2-(5-fluoro-1,3-dihydroisoindol-2-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=C(F)C=C2CN1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 PSGJEOJQZPMKIA-UHFFFAOYSA-N 0.000 claims 1
- NVVSLEVJRNTGFD-UHFFFAOYSA-N 2-[2-(5-fluoro-1,3-dihydroisoindol-2-yl)propyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=C(F)C=C2CN1C(C)CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 NVVSLEVJRNTGFD-UHFFFAOYSA-N 0.000 claims 1
- VQJDDFFABNPVFV-UHFFFAOYSA-N 2-[2-(6,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-5-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(C1)CCC2=C1SC=N2 VQJDDFFABNPVFV-UHFFFAOYSA-N 0.000 claims 1
- WCSQILLYNAUCPU-UHFFFAOYSA-N 2-[2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(C1)CCC2=C1C=CS2 WCSQILLYNAUCPU-UHFFFAOYSA-N 0.000 claims 1
- LMMQNKUIASIDCM-UHFFFAOYSA-N 2-[2-(6,7-dihydro-5h-pyrazolo[1,5-a]pyrimidin-4-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CCN2N=CC=C2N1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 LMMQNKUIASIDCM-UHFFFAOYSA-N 0.000 claims 1
- NFBMJZSNFIFDNE-UHFFFAOYSA-N 2-[2-(6,8-dihydro-5h-1,7-naphthyridin-7-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=CC=CN=C2CN1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 NFBMJZSNFIFDNE-UHFFFAOYSA-N 0.000 claims 1
- LUHWFFWUVXOKSV-UHFFFAOYSA-N 2-[2-(6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=CN=CN=C2CN1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 LUHWFFWUVXOKSV-UHFFFAOYSA-N 0.000 claims 1
- NNRAXUAUHQOONI-UHFFFAOYSA-N 2-[2-(6-fluoro-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=CC(F)=CC=C2CN1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 NNRAXUAUHQOONI-UHFFFAOYSA-N 0.000 claims 1
- OPAYIMAXQXQHMP-UHFFFAOYSA-N 2-[2-(7,8-dihydro-5h-pyrido[3,4-b]pyrazin-6-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=NC=CN=C2CN1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 OPAYIMAXQXQHMP-UHFFFAOYSA-N 0.000 claims 1
- OSPXGNQVUJKEKN-UHFFFAOYSA-N 2-[2-(7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-6-yl)ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=NC=NC=C2CN1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 OSPXGNQVUJKEKN-UHFFFAOYSA-N 0.000 claims 1
- BFAQOEOHVZUZDS-UHFFFAOYSA-N 2-[2-[2-(2,2-dimethylmorpholin-4-yl)-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(CC1=N2)CC1=CC=C2N1CCOC(C)(C)C1 BFAQOEOHVZUZDS-UHFFFAOYSA-N 0.000 claims 1
- OKJQTENFCXGYKQ-UHFFFAOYSA-N 2-[2-[2-(4-ethylpiperazin-1-yl)-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CN(CC)CCN1C1=CC=C(CN(CCC2=NN3C(N)=NC4=C(OC)C=CC=C4C3=N2)C2)C2=N1 OKJQTENFCXGYKQ-UHFFFAOYSA-N 0.000 claims 1
- MREWMQVWHNWJBX-UHFFFAOYSA-N 2-[2-[2-[4-(4-fluorophenyl)piperazin-1-yl]-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(CC1=N2)CC1=CC=C2N(CC1)CCN1C1=CC=C(F)C=C1 MREWMQVWHNWJBX-UHFFFAOYSA-N 0.000 claims 1
- DDDPVGWXUGKTPE-UHFFFAOYSA-N 2-[2-[4-(3,3-difluoropyrrolidin-1-yl)-6,8-dihydro-5h-1,7-naphthyridin-7-yl]ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(C1)CCC2=C1N=CC=C2N1CCC(F)(F)C1 DDDPVGWXUGKTPE-UHFFFAOYSA-N 0.000 claims 1
- LZEGIOPNRSWJFC-UHFFFAOYSA-N 2-[2-[4-(4-ethylpiperazin-1-yl)-6,8-dihydro-5h-1,7-naphthyridin-7-yl]ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CN(CC)CCN1C1=CC=NC2=C1CCN(CCC1=NN3C(N)=NC4=C(OC)C=CC=C4C3=N1)C2 LZEGIOPNRSWJFC-UHFFFAOYSA-N 0.000 claims 1
- QLEJDIUIRRBSQJ-UHFFFAOYSA-N 2-[2-[4-(diethylamino)-6,8-dihydro-5h-1,7-naphthyridin-7-yl]ethyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C12=CC=CC(OC)=C2N=C(N)N2C1=NC(CCN1CC=3N=CC=C(C=3CC1)N(CC)CC)=N2 QLEJDIUIRRBSQJ-UHFFFAOYSA-N 0.000 claims 1
- PWJYXFFEEVOEKS-UHFFFAOYSA-N 2-[3-(4-fluoro-1,3-dihydroisoindol-2-yl)propyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CC(F)=C2CN1CCCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 PWJYXFFEEVOEKS-UHFFFAOYSA-N 0.000 claims 1
- DIEPDGOBSCLMAC-UHFFFAOYSA-N 2-[3-(5-fluoro-1,3-dihydroisoindol-2-yl)propyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=C(F)C=C2CN1CCCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 DIEPDGOBSCLMAC-UHFFFAOYSA-N 0.000 claims 1
- HLRKPHHRWZPQNC-UHFFFAOYSA-N 2-[[5,5-dimethyl-3-(trifluoromethyl)-6,8-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]methyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=NN=C(C(F)(F)F)N2C(C)(C)CN1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 HLRKPHHRWZPQNC-UHFFFAOYSA-N 0.000 claims 1
- WKOQGKNTILEZSK-UHFFFAOYSA-N 2-[[7-(3,4-difluorophenyl)-3,4-dihydro-1h-isoquinolin-2-yl]methyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CN(CC1=C2)CCC1=CC=C2C1=CC=C(F)C(F)=C1 WKOQGKNTILEZSK-UHFFFAOYSA-N 0.000 claims 1
- ZINQJWTULKHUEN-UHFFFAOYSA-N 2-[[7-[2-amino-4-(trifluoromethyl)pyrimidin-5-yl]-3,4-dihydro-1h-isoquinolin-2-yl]methyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CN(CC1=C2)CCC1=CC=C2C1=CN=C(N)N=C1C(F)(F)F ZINQJWTULKHUEN-UHFFFAOYSA-N 0.000 claims 1
- YTDDNQRVZUAKGL-UHFFFAOYSA-N 2-[[8,8-dimethyl-3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]methyl]-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CN2C(C(F)(F)F)=NN=C2C(C)(C)N1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 YTDDNQRVZUAKGL-UHFFFAOYSA-N 0.000 claims 1
- BVXIWFYCOMRDLK-UHFFFAOYSA-N 5-[2-(5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)ethyl]-4,6,7,8-tetrahydropyrazolo[1,5-a][1,4]diazepine-2-carbonitrile Chemical compound C1CCN2N=C(C#N)C=C2CN1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 BVXIWFYCOMRDLK-UHFFFAOYSA-N 0.000 claims 1
- WZBZSPJUFRGSTG-UHFFFAOYSA-N 5-amino-2-(5,7-dihydropyrrolo[3,4-b]pyridin-6-ylmethyl)-[1,2,4]triazolo[1,5-c]quinazoline-7-carbonitrile Chemical compound C1C2=CC=CN=C2CN1CC1=NN2C(N)=NC3=C(C#N)C=CC=C3C2=N1 WZBZSPJUFRGSTG-UHFFFAOYSA-N 0.000 claims 1
- OGSWAWIYAXJCRD-UHFFFAOYSA-N 5-amino-2-(6,8-dihydro-5h-1,7-naphthyridin-7-ylmethyl)-[1,2,4]triazolo[1,5-c]quinazoline-7-carbonitrile Chemical compound C1CC2=CC=CN=C2CN1CC1=NN2C(N)=NC3=C(C#N)C=CC=C3C2=N1 OGSWAWIYAXJCRD-UHFFFAOYSA-N 0.000 claims 1
- KCLSUMJGPGUKAJ-UHFFFAOYSA-N 6-[2-(5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)ethyl]-2-cyclopropyl-5,7-dihydro-4h-thieno[2,3-c]pyridine-3-carbonitrile Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(C1)CCC(C=2C#N)=C1SC=2C1CC1 KCLSUMJGPGUKAJ-UHFFFAOYSA-N 0.000 claims 1
- JNEDCSLFPMAOBV-UHFFFAOYSA-N 7-[(5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)methyl]-n-tert-butyl-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazine-3-carboxamide Chemical compound C1CN2C(C(=O)NC(C)(C)C)=NN=C2CN1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 JNEDCSLFPMAOBV-UHFFFAOYSA-N 0.000 claims 1
- ZKRZVMJHORWESH-UHFFFAOYSA-N 7-[2-(5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)ethyl]-n-tert-butyl-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazine-3-carboxamide Chemical compound C1CN2C(C(=O)NC(C)(C)C)=NN=C2CN1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 ZKRZVMJHORWESH-UHFFFAOYSA-N 0.000 claims 1
- QVYIKVPSQKREJS-UHFFFAOYSA-N 7-chloro-2-[2-(3,4-dihydro-2h-quinolin-1-yl)ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CCC2=CC=CC=C2N1CCC1=NN2C(N)=NC3=C(Cl)C=CC=C3C2=N1 QVYIKVPSQKREJS-UHFFFAOYSA-N 0.000 claims 1
- QKMSQTHUZWSHKE-UHFFFAOYSA-N 7-chloro-2-[2-(5-fluoro-1,3-dihydroisoindol-2-yl)ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=C(F)C=C2CN1CCC1=NN2C(N)=NC3=C(Cl)C=CC=C3C2=N1 QKMSQTHUZWSHKE-UHFFFAOYSA-N 0.000 claims 1
- KZNUKDRGWSPKMY-UHFFFAOYSA-N 7-fluoro-2-[2-(4-fluoro-1,3-dihydroisoindol-2-yl)ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CC(F)=C2CN1CCC1=NN2C(N)=NC3=C(F)C=CC=C3C2=N1 KZNUKDRGWSPKMY-UHFFFAOYSA-N 0.000 claims 1
- XMGUFHCTHWVDQX-UHFFFAOYSA-N 7-fluoro-2-[2-(5-fluoro-1,3-dihydroisoindol-2-yl)ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=C(F)C=C2CN1CCC1=NN2C(N)=NC3=C(F)C=CC=C3C2=N1 XMGUFHCTHWVDQX-UHFFFAOYSA-N 0.000 claims 1
- CTMOJXGSYHKJPG-UHFFFAOYSA-N 7-methoxy-2-(1,2,4,5-tetrahydro-3-benzazepin-3-ylmethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=CC=CC=C2CCN1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 CTMOJXGSYHKJPG-UHFFFAOYSA-N 0.000 claims 1
- XKDUZHIVMHBSST-UHFFFAOYSA-N 7-methoxy-2-(1,3,4,5-tetrahydro-2-benzazepin-2-ylmethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CCC2=CC=CC=C2CN1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 XKDUZHIVMHBSST-UHFFFAOYSA-N 0.000 claims 1
- UHZUNGVKGNFDQE-UHFFFAOYSA-N 7-methoxy-2-(5,6,7,8-tetrahydropyrido[2,3-b]azepin-9-ylmethyl)-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CCCC2=CC=CN=C2N1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 UHZUNGVKGNFDQE-UHFFFAOYSA-N 0.000 claims 1
- UVKVRPNUJISTRX-UHFFFAOYSA-N 7-methoxy-2-[(2-propan-2-yl-4,6-dihydropyrrolo[3,4-d][1,3]thiazol-5-yl)methyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C12=NC(CN3CC=4SC(=NC=4C3)C(C)C)=NN2C(N)=NC2=C1C=CC=C2OC UVKVRPNUJISTRX-UHFFFAOYSA-N 0.000 claims 1
- XDUNBJRSYKTKLS-UHFFFAOYSA-N 7-methoxy-2-[(2-pyridin-2-yl-5,6,7,8-tetrahydropyrido[2,3-b]azepin-9-yl)methyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CN(C1=N2)CCCCC1=CC=C2C1=CC=CC=N1 XDUNBJRSYKTKLS-UHFFFAOYSA-N 0.000 claims 1
- VOHFIVDIVUBPFF-SNVBAGLBSA-N 7-methoxy-2-[(2r)-2-(2-methyl-4,6-dihydropyrrolo[3,4-d][1,3]thiazol-5-yl)propyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C12=NC(C[C@@H](C)N3CC=4SC(C)=NC=4C3)=NN2C(N)=NC2=C1C=CC=C2OC VOHFIVDIVUBPFF-SNVBAGLBSA-N 0.000 claims 1
- YMQFNHHVKFBEMO-LLVKDONJSA-N 7-methoxy-2-[(2r)-2-(2-methyl-6,7-dihydro-4h-[1,3]oxazolo[4,5-c]pyridin-5-yl)propyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1N([C@H](C)CC=2N=C3C=4C=CC=C(C=4N=C(N)N3N=2)OC)CCC2=C1N=C(C)O2 YMQFNHHVKFBEMO-LLVKDONJSA-N 0.000 claims 1
- GKOGSJDSDASPER-CYBMUJFWSA-N 7-methoxy-2-[(2r)-2-(2-methyl-6,7-dihydro-4h-pyrazolo[1,5-a]pyrazin-5-yl)propyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CN2N=C(C)C=C2CN1[C@H](C)CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 GKOGSJDSDASPER-CYBMUJFWSA-N 0.000 claims 1
- GKOGSJDSDASPER-ZDUSSCGKSA-N 7-methoxy-2-[(2s)-2-(2-methyl-6,7-dihydro-4h-pyrazolo[1,5-a]pyrazin-5-yl)propyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CN2N=C(C)C=C2CN1[C@@H](C)CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 GKOGSJDSDASPER-ZDUSSCGKSA-N 0.000 claims 1
- XXVFVFWHRZSSFJ-JTQLQIEISA-N 7-methoxy-2-[(2s)-2-[2-(trifluoromethyl)-6,7-dihydro-4h-[1,3]thiazolo[4,5-c]pyridin-5-yl]propyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1N([C@@H](C)CC=2N=C3C=4C=CC=C(C=4N=C(N)N3N=2)OC)CCC2=C1N=C(C(F)(F)F)S2 XXVFVFWHRZSSFJ-JTQLQIEISA-N 0.000 claims 1
- BSVCNCOXLGHEAQ-UHFFFAOYSA-N 7-methoxy-2-[(5-pyrimidin-5-yl-1,3-dihydroisoindol-2-yl)methyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CN(CC1=C2)CC1=CC=C2C1=CN=CN=C1 BSVCNCOXLGHEAQ-UHFFFAOYSA-N 0.000 claims 1
- CLZXXIWTXKDUPQ-UHFFFAOYSA-N 7-methoxy-2-[(7-methyl-3,4-dihydro-2h-1,8-naphthyridin-1-yl)methyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CCC2=CC=C(C)N=C2N1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 CLZXXIWTXKDUPQ-UHFFFAOYSA-N 0.000 claims 1
- QBEPVDBKRDYRQZ-UHFFFAOYSA-N 7-methoxy-2-[(7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinolin-2-yl)methyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CN(CC1=C2)CCC1=CC=C2C1=CN=CN=C1 QBEPVDBKRDYRQZ-UHFFFAOYSA-N 0.000 claims 1
- YDLMWKCHZGFIJR-UHFFFAOYSA-N 7-methoxy-2-[(8-pyrimidin-5-yl-3,4-dihydro-1h-isoquinolin-2-yl)methyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CN(CC1=2)CCC1=CC=CC=2C1=CN=CN=C1 YDLMWKCHZGFIJR-UHFFFAOYSA-N 0.000 claims 1
- XBSTWYSGCAVPGB-UHFFFAOYSA-N 7-methoxy-2-[2-(2,7,7-trimethyl-4,6-dihydro-[1,3]thiazolo[5,4-c]pyridin-5-yl)ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(CC1(C)C)CC2=C1N=C(C)S2 XBSTWYSGCAVPGB-UHFFFAOYSA-N 0.000 claims 1
- HLYUEBUGUJLIMG-UHFFFAOYSA-N 7-methoxy-2-[2-(2-methyl-4,6-dihydropyrrolo[3,4-d][1,3]oxazol-5-yl)ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C12=NC(CCN3CC=4OC(C)=NC=4C3)=NN2C(N)=NC2=C1C=CC=C2OC HLYUEBUGUJLIMG-UHFFFAOYSA-N 0.000 claims 1
- QBYFWIPJZYHPKM-UHFFFAOYSA-N 7-methoxy-2-[2-(2-methyl-4,6-dihydropyrrolo[3,4-d][1,3]thiazol-5-yl)ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C12=NC(CCN3CC=4SC(C)=NC=4C3)=NN2C(N)=NC2=C1C=CC=C2OC QBYFWIPJZYHPKM-UHFFFAOYSA-N 0.000 claims 1
- NSVAOGCQTSGLRR-UHFFFAOYSA-N 7-methoxy-2-[2-(2-methyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-6-yl)ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CN=C(C)N=C2CN1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 NSVAOGCQTSGLRR-UHFFFAOYSA-N 0.000 claims 1
- YBQCIJFMPPGXJF-UHFFFAOYSA-N 7-methoxy-2-[2-(2-morpholin-4-yl-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl)ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(CC1=N2)CC1=CC=C2N1CCOCC1 YBQCIJFMPPGXJF-UHFFFAOYSA-N 0.000 claims 1
- AJEFQLPREKYDHS-UHFFFAOYSA-N 7-methoxy-2-[2-(3-methylsulfanyl-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazin-7-yl)ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CN2C(SC)=NN=C2CN1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 AJEFQLPREKYDHS-UHFFFAOYSA-N 0.000 claims 1
- AXRRGPRSOHGZKS-UHFFFAOYSA-N 7-methoxy-2-[2-(3-phenyl-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-5-yl)ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(CC=12)CC=1NN=C2C1=CC=CC=C1 AXRRGPRSOHGZKS-UHFFFAOYSA-N 0.000 claims 1
- DKKWFEICRJIDLC-UHFFFAOYSA-N 7-methoxy-2-[2-(7-pyrimidin-5-yl-3,4-dihydro-1h-isoquinolin-2-yl)ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(CC1=C2)CCC1=CC=C2C1=CN=CN=C1 DKKWFEICRJIDLC-UHFFFAOYSA-N 0.000 claims 1
- FYKAFYKPJHXGEN-UHFFFAOYSA-N 7-methoxy-2-[2-[2-(4-methylpiperazin-1-yl)-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(CC1=N2)CC1=CC=C2N1CCN(C)CC1 FYKAFYKPJHXGEN-UHFFFAOYSA-N 0.000 claims 1
- HNVJCTMAZIUGBX-UHFFFAOYSA-N 7-methoxy-2-[2-[2-(4-morpholin-4-ylpiperidin-1-yl)-5,7-dihydropyrrolo[3,4-b]pyridin-6-yl]ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(CC1=N2)CC1=CC=C2N(CC1)CCC1N1CCOCC1 HNVJCTMAZIUGBX-UHFFFAOYSA-N 0.000 claims 1
- ISEHWJOQIRTNRH-UHFFFAOYSA-N 7-methoxy-2-[2-[2-(trifluoromethyl)-3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl]ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(C1)CCC2=C1NC(C(F)(F)F)=N2 ISEHWJOQIRTNRH-UHFFFAOYSA-N 0.000 claims 1
- JJZVWMXULWLISU-UHFFFAOYSA-N 7-methoxy-2-[2-[3-(trifluoromethyl)-1,4,5,7-tetrahydropyrazolo[3,4-c]pyridin-6-yl]ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(C1)CCC2=C1NN=C2C(F)(F)F JJZVWMXULWLISU-UHFFFAOYSA-N 0.000 claims 1
- CEFPMIQLDPIQSP-UHFFFAOYSA-N 7-methoxy-2-[2-[3-(trifluoromethyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl]ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(C1)CCC2=C1C(C(F)(F)F)=NN2 CEFPMIQLDPIQSP-UHFFFAOYSA-N 0.000 claims 1
- VPJAZLILJXGOKM-UHFFFAOYSA-N 7-methoxy-2-[2-[5-(trifluoromethyl)-1,3-dihydroisoindol-2-yl]ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=C(C(F)(F)F)C=C2CN1CCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 VPJAZLILJXGOKM-UHFFFAOYSA-N 0.000 claims 1
- VWDKMXMLSNNKBT-UHFFFAOYSA-N 7-methoxy-2-[2-[7-[2-(trifluoromethyl)pyrimidin-5-yl]-3,4-dihydro-1h-isoquinolin-2-yl]ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CCN(CC1=C2)CCC1=CC=C2C1=CN=C(C(F)(F)F)N=C1 VWDKMXMLSNNKBT-UHFFFAOYSA-N 0.000 claims 1
- SQEWKUWSYZFAQC-UHFFFAOYSA-N 7-methoxy-2-[3-[5-(trifluoromethyl)-1,3-dihydroisoindol-2-yl]propyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=C(C(F)(F)F)C=C2CN1CCCC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 SQEWKUWSYZFAQC-UHFFFAOYSA-N 0.000 claims 1
- QGPGFKSIMVGOOJ-UHFFFAOYSA-N 7-methoxy-2-[[2-(trifluoromethyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-6-yl]methyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CN=C(C(F)(F)F)N=C2CN1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 QGPGFKSIMVGOOJ-UHFFFAOYSA-N 0.000 claims 1
- PEABSZCMACAHCA-UHFFFAOYSA-N 7-methoxy-2-[[3-(trifluoromethyl)-7,8-dihydro-5h-1,6-naphthyridin-6-yl]methyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1CC2=NC=C(C(F)(F)F)C=C2CN1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 PEABSZCMACAHCA-UHFFFAOYSA-N 0.000 claims 1
- RYYPISAKIYXXSL-UHFFFAOYSA-N 7-methoxy-2-[[5-(trifluoromethyl)-1,3-dihydroisoindol-2-yl]methyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=C(C(F)(F)F)C=C2CN1CC1=NN(C(N)=NC=2C(OC)=CC=CC=22)C2=N1 RYYPISAKIYXXSL-UHFFFAOYSA-N 0.000 claims 1
- YBIUMXDWDYRFDQ-UHFFFAOYSA-N 7-methoxy-2-[[7-[2-(trifluoromethyl)phenyl]-3,4-dihydro-1h-isoquinolin-2-yl]methyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CN(CC1=C2)CCC1=CC=C2C1=CC=CC=C1C(F)(F)F YBIUMXDWDYRFDQ-UHFFFAOYSA-N 0.000 claims 1
- UITVBQLRRKPXFI-UHFFFAOYSA-N 8-fluoro-2-[2-(4-fluoro-1,3-dihydroisoindol-2-yl)ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=CC(F)=C2CN1CCC1=NN2C(N)=NC3=CC(F)=CC=C3C2=N1 UITVBQLRRKPXFI-UHFFFAOYSA-N 0.000 claims 1
- BFCYWWWTNDJASC-UHFFFAOYSA-N 8-fluoro-2-[2-(5-fluoro-1,3-dihydroisoindol-2-yl)ethyl]-[1,2,4]triazolo[1,5-c]quinazolin-5-amine Chemical compound C1C2=CC=C(F)C=C2CN1CCC1=NN2C(N)=NC3=CC(F)=CC=C3C2=N1 BFCYWWWTNDJASC-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- JMYVMOUINOAAPA-UHFFFAOYSA-N cyclopropanecarbaldehyde Chemical compound O=CC1CC1 JMYVMOUINOAAPA-UHFFFAOYSA-N 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- LLWGVHKQDPWXQI-UHFFFAOYSA-N ethyl 7-[2-(5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)ethyl]-6,8-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrazine-3-carboxylate Chemical compound C12=CC=CC(OC)=C2N=C(N)N2C1=NC(CCN1CC3=NN=C(N3CC1)C(=O)OCC)=N2 LLWGVHKQDPWXQI-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- DGMDMWYIRPMRRM-UHFFFAOYSA-N n-[2-[(5-amino-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-2-yl)methyl]-3,4-dihydro-1h-isoquinolin-7-yl]pyridine-2-carboxamide Chemical compound N=1N2C(N)=NC=3C(OC)=CC=CC=3C2=NC=1CN(CC1=C2)CCC1=CC=C2NC(=O)C1=CC=CC=N1 DGMDMWYIRPMRRM-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 101150051188 Adora2a gene Proteins 0.000 abstract 3
- 208000025966 Neurological disease Diseases 0.000 abstract 2
- 239000005557 antagonist Substances 0.000 abstract 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
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- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- General Chemical & Material Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Epidemiology (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
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- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2012/087865 WO2014101120A1 (en) | 2012-12-28 | 2012-12-28 | Heterobicyclo-substituted-7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine compounds with a2a antagonist properties |
| PCT/CN2013/076853 WO2014101373A1 (en) | 2012-12-28 | 2013-06-06 | Heterobicyclo-substituted-[1,2,4]triazolo[1,5-c]quinazolin-5-amine compounds for treatment of central nervous system disorder |
| EP13866588.0A EP2945632B1 (en) | 2012-12-28 | 2013-12-20 | Heterobicyclo-substituted-[1,2,4]triazolo[1,5-c]quinazolin-5-amine compounds suitable for treatment or prevention of central nervous system disorders |
| PCT/US2013/076781 WO2014105666A1 (en) | 2012-12-28 | 2013-12-20 | Heterobicyclo-substituted-[1,2,4]triazolo[1,5-c]quinazolin-5-amine compounds with a2a antagonist properties |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI2945632T1 true SI2945632T1 (en) | 2018-05-31 |
Family
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| HK1257102A1 (zh) | 2015-08-21 | 2019-10-11 | Portola Pharmaceuticals, Inc. | 苯基哌嗪前蛋白转化酶枯草杆菌蛋白酶/kexin9型(pcsk9)调节剂及其应用 |
| HK1260897A1 (zh) | 2015-08-21 | 2019-12-27 | Portola Pharmaceuticals, Inc. | 使用四氢异喹啉小分子来结合并调节pcsk9的蛋白活性的组合物和方法 |
| WO2017107087A1 (en) * | 2015-12-23 | 2017-06-29 | Merck Sharp & Dohme Corp. | 6, 7-dihydro-5h-pyrrolo [3, 4-b] pyridin-5-oneallosteric modulators of the m4 muscarinic acetylcholine receptor |
| WO2017107089A1 (en) | 2015-12-23 | 2017-06-29 | Merck Sharp & Dohme Corp. | 3- (1h-pyrazol-4-yl) pyridineallosteric modulators of the m4 muscarinic acetylcholine receptor |
| ES2789756T3 (es) | 2015-12-23 | 2020-10-26 | Merck Sharp & Dohme | Moduladores alostéricos de 6,7-dihidro-5H-pirrolo[3,4-b]piridin-5-ona del receptor de acetilcolina muscarínico M4 |
| US20190119236A1 (en) | 2016-02-23 | 2019-04-25 | Portola Pharmaceuticals, Inc. | Compounds for binding proprotein convertase subtilisin/kexin type 9 (pcsk9) |
| WO2018112843A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | Heteroaryl piperidine ether allosteric modulators of the m4 muscarinic acetylcholine receptor |
| WO2018112842A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | 6,6-fused heteroaryl piperidine ether allosteric modulators of m4 muscarinic acetylcholine receptor |
| CN108884061B (zh) | 2017-01-13 | 2021-11-16 | 江苏恒瑞医药股份有限公司 | 1,2,4-三嗪-3-胺类衍生物、其制备方法及其在医药上的应用 |
| SG11201907909TA (en) | 2017-02-27 | 2019-09-27 | Betta Pharmaceuticals Co Ltd | Fgfr inhibitor and application thereof |
| CN109963854B (zh) | 2017-03-16 | 2022-04-12 | 江苏恒瑞医药股份有限公司 | 杂芳基并[4,3-c]嘧啶-5-胺类衍生物、其制备方法及其在医药上的应用 |
| EP3686199B9 (en) | 2017-09-28 | 2022-12-07 | Cstone Pharmaceuticals (Suzhou) Co., Ltd. | Fused ring derivative as a2a receptor inhibitor |
| US11498923B2 (en) | 2017-12-13 | 2022-11-15 | Merck Sharp & Dohme Llc | Substituted imidazo[1,2-c]quinazolines as A2A antagonists |
| CA3089159A1 (en) | 2018-02-06 | 2019-08-15 | Jiangsu Hengrui Medicine Co., Ltd. | Pyrazolo[1,5-a][1,3,5]triazine-2-amine derivative, preparation method therefor and medical use thereof |
| WO2020106560A1 (en) | 2018-11-20 | 2020-05-28 | Merck Sharp & Dohme Corp. | Substituted amino triazolopyrimidine and amino triazolopyrazine adenosine receptor antagonists, pharmaceutical compositions and their use |
| KR20210093964A (ko) | 2018-11-20 | 2021-07-28 | 머크 샤프 앤드 돔 코포레이션 | 치환된 아미노 트리아졸로피리미딘 및 아미노 트리아졸로피라진 아데노신 수용체 길항제, 제약 조성물 및 그의 용도 |
| US12263171B2 (en) | 2018-11-30 | 2025-04-01 | Merck Sharp & Dohme Llc | 7-, 8-, and 10-substituted amino triazolo quinazoline derivatives as adenosine receptor antagonists, pharmaceutical compositions and their use |
| CR20210271A (es) | 2018-11-30 | 2021-07-14 | Merck Sharp & Dohme | Derivados de amino triazolo quinazolina 9-sustituidos como antagonistas del receptor de adenosina, composiciones farmacéuticas y su uso |
| CA3126735A1 (en) | 2019-01-11 | 2020-07-16 | Omeros Corporation | Methods and compositions for treating cancer |
| AR117844A1 (es) | 2019-01-22 | 2021-09-01 | Merck Patent Gmbh | Derivados de tiazolopiridina como antagonistas del receptor de adenosina |
| JP7066913B2 (ja) | 2019-03-26 | 2022-05-13 | ノベルファーマ株式会社 | 持続型脂肪酸結合ＧｎＲＨ誘導体及びこれを含む薬剤学的組成物 |
| FI4097099T3 (fi) | 2020-02-07 | 2024-07-30 | Gasherbrum Bio Inc | Heterosyklisiä glp-1-agonisteja |
| WO2022020550A1 (en) * | 2020-07-24 | 2022-01-27 | Merck Sharp & Dohme Corp. | Adenosine a2a and a2b receptor dual antagonists for immuno-oncology |
| WO2022020552A1 (en) * | 2020-07-24 | 2022-01-27 | Merck Sharp & Dohme Corp. | Adenosine a2a and a2b receptor dual antagonists for immuno-oncology |
| CN112159411A (zh) * | 2020-10-15 | 2021-01-01 | 南京工业大学 | 一种三氟甲基取代嘧啶并[1,3]二氮杂*化合物及其制备方法 |
| US12115154B2 (en) | 2020-12-16 | 2024-10-15 | Srx Cardio, Llc | Compounds for the modulation of proprotein convertase subtilisin/kexin type 9 (PCSK9) |
| AU2023252914A1 (en) | 2022-04-13 | 2024-10-17 | Arcus Biosciences, Inc. | Combination therapy for treating trop-2 expressing cancers |
| IL322686A (en) | 2023-02-16 | 2025-10-01 | Gasherbrum Bio Inc | Heterocyclic glp-1 agonists |
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| CA2144330A1 (en) * | 1993-07-27 | 1995-02-09 | Fumio Suzuki | A therapeutic agent for parkinson's disease |
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| IT1277392B1 (it) | 1995-07-28 | 1997-11-10 | Schering Plough S P A | Analoghi eterociclici di 1,2,4-triazolo(1,5-c]pirimidine ad attivita' antagonista per il recettore a2a dell'adenosina |
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| BR0317436A (pt) * | 2002-12-19 | 2005-11-16 | Schering Corp | Usos de antagonistas do receptor a2a de adenosina |
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| WO2012135084A1 (en) * | 2011-03-31 | 2012-10-04 | Merck Sharp & Dohme Corp. | METABOLITES OF 2-(FURAN-2-YL)-7-(2-(4-(4-(2-METHOXYETHOXY)PHENYL)PIPERAZIN-1-YL)ETHYL)-7H-PYRAZOLO[4,3-e][1,2,4]TRIAZOLO[1,5-c]PYRIMIDIN-5-AMINE AND THEIR UTILITY AS ADENOSINE A2a RECEPTOR ANTAGONISTS |
| WO2014101113A1 (en) | 2012-12-28 | 2014-07-03 | Merck Sharp & Dohme Corp. | Piperazine-substituted 7-methoxy-[1,2,4]triazolo[1,5-c]quinazolin-5-amine compounds with a2a antagonist properties |
-
2012
- 2012-12-28 WO PCT/CN2012/087865 patent/WO2014101120A1/en not_active Ceased
-
2013
- 2013-06-06 WO PCT/CN2013/076853 patent/WO2014101373A1/en not_active Ceased
- 2013-12-20 AU AU2013370977A patent/AU2013370977B2/en not_active Ceased
- 2013-12-20 BR BR112015015468A patent/BR112015015468B8/pt not_active IP Right Cessation
- 2013-12-20 EP EP13866588.0A patent/EP2945632B1/en active Active
- 2013-12-20 NO NO13866588A patent/NO2945632T3/no unknown
- 2013-12-20 HR HRP20180678TT patent/HRP20180678T1/hr unknown
- 2013-12-20 RU RU2015131148A patent/RU2671628C2/ru active
- 2013-12-20 WO PCT/US2013/076781 patent/WO2014105666A1/en not_active Ceased
- 2013-12-20 US US14/655,648 patent/US9708347B2/en active Active
- 2013-12-20 HU HUE13866588A patent/HUE037950T2/hu unknown
- 2013-12-20 ME MEP-2018-97A patent/ME03034B/me unknown
- 2013-12-20 MX MX2015008481A patent/MX370017B/es active IP Right Grant
- 2013-12-20 RS RS20180410A patent/RS57162B1/sr unknown
- 2013-12-20 KR KR1020157020147A patent/KR102165113B1/ko not_active Expired - Fee Related
- 2013-12-20 JP JP2015550682A patent/JP6306049B2/ja not_active Expired - Fee Related
- 2013-12-20 CA CA2896056A patent/CA2896056C/en active Active
- 2013-12-20 DK DK13866588.0T patent/DK2945632T3/en active
- 2013-12-20 ES ES13866588.0T patent/ES2667477T3/es active Active
- 2013-12-20 PT PT138665880T patent/PT2945632T/pt unknown
- 2013-12-20 PL PL13866588T patent/PL2945632T3/pl unknown
- 2013-12-20 LT LTEP13866588.0T patent/LT2945632T/lt unknown
- 2013-12-20 RU RU2018136104A patent/RU2018136104A/ru unknown
- 2013-12-20 SI SI201330980T patent/SI2945632T1/en unknown
-
2017
- 2017-02-02 US US15/423,238 patent/US10011615B2/en active Active
-
2018
- 2018-05-04 CY CY20181100472T patent/CY1120258T1/el unknown
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