JP2016164184A5 - - Google Patents
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- Publication number
- JP2016164184A5 JP2016164184A5 JP2016081792A JP2016081792A JP2016164184A5 JP 2016164184 A5 JP2016164184 A5 JP 2016164184A5 JP 2016081792 A JP2016081792 A JP 2016081792A JP 2016081792 A JP2016081792 A JP 2016081792A JP 2016164184 A5 JP2016164184 A5 JP 2016164184A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- pyridin
- triazolo
- methyl
- 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.)
- Granted
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- 229910052739 hydrogen Inorganic materials 0.000 claims 31
- 239000001257 hydrogen Substances 0.000 claims 31
- 125000000217 alkyl group Chemical group 0.000 claims 29
- 150000002431 hydrogen Chemical class 0.000 claims 29
- -1 nitro, hydroxy Chemical group 0.000 claims 25
- 229910052736 halogen Inorganic materials 0.000 claims 23
- 150000002367 halogens Chemical class 0.000 claims 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims 21
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 19
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 19
- 125000003342 alkenyl group Chemical group 0.000 claims 15
- 125000000304 alkynyl group Chemical group 0.000 claims 15
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- 125000000623 heterocyclic group Chemical group 0.000 claims 14
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000005842 heteroatom Chemical group 0.000 claims 11
- 229920006395 saturated elastomer Polymers 0.000 claims 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 10
- 125000004043 oxo group Chemical group O=* 0.000 claims 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims 9
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 9
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- 125000004429 atom Chemical group 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 4
- 150000001204 N-oxides Chemical class 0.000 claims 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 4
- 150000002357 guanidines Chemical class 0.000 claims 4
- 208000027866 inflammatory disease Diseases 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 239000000651 prodrug Substances 0.000 claims 4
- 229940002612 prodrug Drugs 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 208000017169 kidney disease Diseases 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 230000002062 proliferating effect Effects 0.000 claims 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 210000000987 immune system Anatomy 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical group COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- ORMPCQCCZCCYRS-UHFFFAOYSA-N 1-pyrrolidin-1-yl-2-[4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]pyrazol-1-yl]ethanone Chemical compound C1=C(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)C=NN1CC(=O)N1CCCC1 ORMPCQCCZCCYRS-UHFFFAOYSA-N 0.000 claims 1
- ALWGIHOBLHQXHI-UHFFFAOYSA-N 2,6-difluoro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzoic acid Chemical compound C1=C(F)C(C(=O)O)=C(F)C=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 ALWGIHOBLHQXHI-UHFFFAOYSA-N 0.000 claims 1
- GPIHCFYCDZFCDV-UHFFFAOYSA-N 2-[4-[3-(quinolin-6-ylmethyl)imidazo[4,5-b]pyridin-5-yl]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1C1=CC=C(N=CN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 GPIHCFYCDZFCDV-UHFFFAOYSA-N 0.000 claims 1
- UWAXBTWQEMCYOB-UHFFFAOYSA-N 2-[4-[3-[(4-fluorophenyl)methyl]triazolo[4,5-b]pyridin-5-yl]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1C1=CC=C(N=NN2CC=3C=CC(F)=CC=3)C2=N1 UWAXBTWQEMCYOB-UHFFFAOYSA-N 0.000 claims 1
- LJPOWVUYWNNDPJ-UHFFFAOYSA-N 2-chloro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 LJPOWVUYWNNDPJ-UHFFFAOYSA-N 0.000 claims 1
- UYAQGFXNQDLVJN-UHFFFAOYSA-N 2-chloro-4-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyridin-5-yl]benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC=C1C1=CC=C(N=NN2CC=3C(=CC4=NC=CC=C4C=3)F)C2=N1 UYAQGFXNQDLVJN-UHFFFAOYSA-N 0.000 claims 1
- HITBWJDLEMFHPX-UHFFFAOYSA-N 2-fluoro-4-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyridin-5-yl]benzoic acid Chemical compound C1=C(F)C(C(=O)O)=CC=C1C1=CC=C(N=NN2CC=3C(=CC4=NC=CC=C4C=3)F)C2=N1 HITBWJDLEMFHPX-UHFFFAOYSA-N 0.000 claims 1
- MNNQPYIMWLYJPE-UHFFFAOYSA-N 2-fluoro-5-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzoic acid Chemical compound C1=C(F)C(C(=O)O)=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=C1 MNNQPYIMWLYJPE-UHFFFAOYSA-N 0.000 claims 1
- XLJAEALBDQMDPH-UHFFFAOYSA-N 3-[(2-chloro-3,6-difluorophenyl)methyl]-5-(1h-pyrazol-4-yl)triazolo[4,5-b]pyridine Chemical compound FC1=CC=C(F)C(CN2C3=NC(=CC=C3N=N2)C2=CNN=C2)=C1Cl XLJAEALBDQMDPH-UHFFFAOYSA-N 0.000 claims 1
- RHGWLAMTNFNTTC-UHFFFAOYSA-N 3-[(4-fluorophenyl)methyl]-5-(1h-pyrazol-4-yl)triazolo[4,5-b]pyridine Chemical compound C1=CC(F)=CC=C1CN1C2=NC(C3=CNN=C3)=CC=C2N=N1 RHGWLAMTNFNTTC-UHFFFAOYSA-N 0.000 claims 1
- VYQMYFVPYBLEMZ-UHFFFAOYSA-N 3-[(4-fluorophenyl)methyl]-5-[1-[2-(oxan-2-yloxy)ethyl]pyrazol-4-yl]triazolo[4,5-b]pyridine Chemical compound C1=CC(F)=CC=C1CN1C2=NC(C3=CN(CCOC4OCCCC4)N=C3)=CC=C2N=N1 VYQMYFVPYBLEMZ-UHFFFAOYSA-N 0.000 claims 1
- VDAHJTPNAURLGG-UHFFFAOYSA-N 3-[2-fluoro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]anilino]propanoic acid Chemical compound C1=C(F)C(NCCC(=O)O)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 VDAHJTPNAURLGG-UHFFFAOYSA-N 0.000 claims 1
- UFXQSELVQCEGNG-UHFFFAOYSA-N 3-[2-fluoro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]phenoxy]-n,n-dimethylpropan-1-amine Chemical compound C1=C(F)C(OCCCN(C)C)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 UFXQSELVQCEGNG-UHFFFAOYSA-N 0.000 claims 1
- QLQUQUKKUXUUTL-UHFFFAOYSA-N 3-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]phenol Chemical compound OC1=CC=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=C1 QLQUQUKKUXUUTL-UHFFFAOYSA-N 0.000 claims 1
- HWWJLBMAILCFQO-UHFFFAOYSA-N 4-[2-[4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]pyrazol-1-yl]ethyl]morpholine;hydrochloride Chemical compound Cl.C1=C(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)C=NN1CCN1CCOCC1 HWWJLBMAILCFQO-UHFFFAOYSA-N 0.000 claims 1
- NWLGQZOICWXIDQ-UHFFFAOYSA-N 4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]thiophene-2-carbaldehyde Chemical compound S1C(C=O)=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=C1 NWLGQZOICWXIDQ-UHFFFAOYSA-N 0.000 claims 1
- WZOOINDUBKOYLP-UHFFFAOYSA-N 4-[3-[(2-chloro-3,6-difluorophenyl)methyl]triazolo[4,5-b]pyridin-5-yl]-2-fluoro-n-methylbenzamide Chemical compound C1=C(F)C(C(=O)NC)=CC=C1C1=CC=C(N=NN2CC=3C(=C(F)C=CC=3F)Cl)C2=N1 WZOOINDUBKOYLP-UHFFFAOYSA-N 0.000 claims 1
- QNLWFZHIVAIMIX-UHFFFAOYSA-N 4-[3-[(2-chloro-3,6-difluorophenyl)methyl]triazolo[4,5-b]pyridin-5-yl]-2-fluorobenzoic acid Chemical compound C1=C(F)C(C(=O)O)=CC=C1C1=CC=C(N=NN2CC=3C(=C(F)C=CC=3F)Cl)C2=N1 QNLWFZHIVAIMIX-UHFFFAOYSA-N 0.000 claims 1
- RAFIMVFKDKTGCA-UHFFFAOYSA-N 4-[5-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]pyridin-2-yl]morpholine Chemical compound C=1C=C2N=CC=CC2=CC=1CN(C1=N2)N=NC1=CC=C2C(C=N1)=CC=C1N1CCOCC1 RAFIMVFKDKTGCA-UHFFFAOYSA-N 0.000 claims 1
- HWXVFQMRTFVHNM-UHFFFAOYSA-N 5-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 HWXVFQMRTFVHNM-UHFFFAOYSA-N 0.000 claims 1
- BKKFMXBUPHSOLH-UHFFFAOYSA-N 6-[(5-pyridin-3-yltriazolo[4,5-b]pyridin-3-yl)methyl]quinoline Chemical compound C=1C=C2N=CC=CC2=CC=1CN(C1=N2)N=NC1=CC=C2C1=CC=CN=C1 BKKFMXBUPHSOLH-UHFFFAOYSA-N 0.000 claims 1
- FHZXWTLERUQXSJ-UHFFFAOYSA-N 6-[1-[5-(1h-pyrazol-4-yl)triazolo[4,5-b]pyridin-3-yl]ethyl]quinoline Chemical compound C=1C=C2N=CC=CC2=CC=1C(C)N(C1=N2)N=NC1=CC=C2C=1C=NNC=1 FHZXWTLERUQXSJ-UHFFFAOYSA-N 0.000 claims 1
- PZTDNJQKFWDRCA-UHFFFAOYSA-N 6-[2-[5-(1h-pyrazol-4-yl)triazolo[4,5-b]pyridin-3-yl]propan-2-yl]quinoline Chemical compound C=1C=C2N=CC=CC2=CC=1C(C)(C)N(C1=N2)N=NC1=CC=C2C=1C=NNC=1 PZTDNJQKFWDRCA-UHFFFAOYSA-N 0.000 claims 1
- YAHRBSLCKASTSJ-UHFFFAOYSA-N 6-[[5-(1,3-benzodioxol-5-yl)triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound C1=C2OCOC2=CC(C2=CC=C3N=NN(C3=N2)CC=2C=C3C=CC=NC3=CC=2)=C1 YAHRBSLCKASTSJ-UHFFFAOYSA-N 0.000 claims 1
- CSXOGDAIIWKSQA-UHFFFAOYSA-N 6-[[5-(1-methylpyrazol-4-yl)triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound C1=NN(C)C=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 CSXOGDAIIWKSQA-UHFFFAOYSA-N 0.000 claims 1
- SZHOGKOEYCYZDY-UHFFFAOYSA-N 6-[[5-(1-propan-2-ylpyrazol-4-yl)triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound C1=NN(C(C)C)C=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 SZHOGKOEYCYZDY-UHFFFAOYSA-N 0.000 claims 1
- SJBXSAIMLUFQDU-UHFFFAOYSA-N 6-[[5-(2,3-dihydro-1-benzofuran-5-yl)triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound C1=C2OCCC2=CC(C2=CC=C3N=NN(C3=N2)CC=2C=C3C=CC=NC3=CC=2)=C1 SJBXSAIMLUFQDU-UHFFFAOYSA-N 0.000 claims 1
- QZKXDQKEKSAKKF-UHFFFAOYSA-N 6-[[5-(2-chloropyridin-4-yl)triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound C1=NC(Cl)=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=C1 QZKXDQKEKSAKKF-UHFFFAOYSA-N 0.000 claims 1
- HRIPFUDSGLOHJK-UHFFFAOYSA-N 6-[[5-(2-methoxypyrimidin-5-yl)triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound C1=NC(OC)=NC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 HRIPFUDSGLOHJK-UHFFFAOYSA-N 0.000 claims 1
- YHGDKKUDPGIYAX-UHFFFAOYSA-N 6-[[5-(3-ethyl-2h-indazol-6-yl)triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound N1=CC=CC2=CC(CN3N=NC4=CC=C(N=C43)C=3C=C4NN=C(C4=CC=3)CC)=CC=C21 YHGDKKUDPGIYAX-UHFFFAOYSA-N 0.000 claims 1
- NZXKWYYKGUFLDC-UHFFFAOYSA-N 6-[[5-(3-fluoro-4-methoxyphenyl)triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound C1=C(F)C(OC)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 NZXKWYYKGUFLDC-UHFFFAOYSA-N 0.000 claims 1
- UNDZNEMPJSSXBA-UHFFFAOYSA-N 6-[[5-(3-fluoro-4-propan-2-yloxyphenyl)triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound C1=C(F)C(OC(C)C)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 UNDZNEMPJSSXBA-UHFFFAOYSA-N 0.000 claims 1
- BPBRABRIFQMQNN-UHFFFAOYSA-N 6-[[5-(3-methyl-2h-indazol-5-yl)triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound N1=CC=CC2=CC(CN3N=NC4=CC=C(N=C43)C3=CC=C4NN=C(C4=C3)C)=CC=C21 BPBRABRIFQMQNN-UHFFFAOYSA-N 0.000 claims 1
- WZWLRCQHBFCPMJ-UHFFFAOYSA-N 6-[[5-(4-methylpiperazin-1-yl)triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound C1CN(C)CCN1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 WZWLRCQHBFCPMJ-UHFFFAOYSA-N 0.000 claims 1
- PYDGAVYKYVRRBU-UHFFFAOYSA-N 6-[[5-(4-methylthiophen-2-yl)triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound CC1=CSC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=C1 PYDGAVYKYVRRBU-UHFFFAOYSA-N 0.000 claims 1
- KVUBAQLZTUEXJY-UHFFFAOYSA-N 6-[[5-(5-methyl-1h-pyrazol-4-yl)triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound CC1=NNC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 KVUBAQLZTUEXJY-UHFFFAOYSA-N 0.000 claims 1
- QALNKKMNDHKQFK-UHFFFAOYSA-N 6-[[5-(5-methylthiophen-2-yl)triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound S1C(C)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 QALNKKMNDHKQFK-UHFFFAOYSA-N 0.000 claims 1
- DYEJAVYGLJOIMC-UHFFFAOYSA-N 6-[[5-(6-piperidin-1-ylpyridin-3-yl)triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound C=1C=C2N=CC=CC2=CC=1CN(C1=N2)N=NC1=CC=C2C(C=N1)=CC=C1N1CCCCC1 DYEJAVYGLJOIMC-UHFFFAOYSA-N 0.000 claims 1
- IGIUTMDUBFGCAM-UHFFFAOYSA-N 6-[[5-[1-(2-fluoroethyl)pyrazol-4-yl]triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound C1=NN(CCF)C=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 IGIUTMDUBFGCAM-UHFFFAOYSA-N 0.000 claims 1
- VCFLTCNSYFRNTD-SFHVURJKSA-N 6-[[5-[1-[(3s)-pyrrolidin-3-yl]pyrazol-4-yl]triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound C=1C=C2N=CC=CC2=CC=1CN(C1=N2)N=NC1=CC=C2C(=C1)C=NN1[C@H]1CCNC1 VCFLTCNSYFRNTD-SFHVURJKSA-N 0.000 claims 1
- KAHHADLNMIZCIU-FERBBOLQSA-N 6-[[5-[1-[(3s)-pyrrolidin-3-yl]pyrazol-4-yl]triazolo[4,5-b]pyridin-3-yl]methyl]quinoline;hydrochloride Chemical compound Cl.C=1C=C2N=CC=CC2=CC=1CN(C1=N2)N=NC1=CC=C2C(=C1)C=NN1[C@H]1CCNC1 KAHHADLNMIZCIU-FERBBOLQSA-N 0.000 claims 1
- WYHMGKKHEXQPLZ-UHFFFAOYSA-N 6-[[5-[1-[2-(oxan-2-yloxy)ethyl]pyrazol-4-yl]imidazo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound C1=C(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)C=NC3=CC=2)C=NN1CCOC1CCCCO1 WYHMGKKHEXQPLZ-UHFFFAOYSA-N 0.000 claims 1
- SYRZXJREPPVSLQ-UHFFFAOYSA-N 6-[[5-[1-[2-(oxan-2-yloxy)ethyl]pyrazol-4-yl]triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound C1=C(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)C=NN1CCOC1CCCCO1 SYRZXJREPPVSLQ-UHFFFAOYSA-N 0.000 claims 1
- MGVOQNWFIKYNRQ-UHFFFAOYSA-N 6-[[5-[3-(2,2,2-trifluoroethoxy)phenyl]triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound FC(F)(F)COC1=CC=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=C1 MGVOQNWFIKYNRQ-UHFFFAOYSA-N 0.000 claims 1
- KDLQLIDBKPAYPG-UHFFFAOYSA-N 6-[[5-[3-(difluoromethoxy)phenyl]triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound FC(F)OC1=CC=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=C1 KDLQLIDBKPAYPG-UHFFFAOYSA-N 0.000 claims 1
- KFCJESDVMBISFX-UHFFFAOYSA-N 6-[[5-[3-(trifluoromethoxy)phenyl]triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound FC(F)(F)OC1=CC=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=C1 KFCJESDVMBISFX-UHFFFAOYSA-N 0.000 claims 1
- LJDJZKISZSVCNZ-UHFFFAOYSA-N 6-[[5-[3-fluoro-4-(2-methoxyethoxy)phenyl]triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound C1=C(F)C(OCCOC)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 LJDJZKISZSVCNZ-UHFFFAOYSA-N 0.000 claims 1
- FNZWPWVGNLXRLO-UHFFFAOYSA-N 6-[[5-[3-fluoro-4-(2-methylpropoxy)phenyl]triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound C1=C(F)C(OCC(C)C)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 FNZWPWVGNLXRLO-UHFFFAOYSA-N 0.000 claims 1
- SDZUYTJIZLNDPN-UHFFFAOYSA-N 6-[[5-[3-fluoro-4-(oxan-4-yloxy)phenyl]triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound FC1=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=CC=C1OC1CCOCC1 SDZUYTJIZLNDPN-UHFFFAOYSA-N 0.000 claims 1
- SAXRTVKOLWFSFL-UHFFFAOYSA-N 6-[[5-[4-(cyclopropylmethoxy)-3-fluorophenyl]triazolo[4,5-b]pyridin-3-yl]methyl]quinoline Chemical compound FC1=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=CC=C1OCC1CC1 SAXRTVKOLWFSFL-UHFFFAOYSA-N 0.000 claims 1
- RKUJPBFUCQBRTP-UHFFFAOYSA-N C1(=CC=CC=C1)NC1=CC=C2C(=N1)N(N=N2)CC=2C=C1C=CC=NC1=CC2.N2=CC=CC1=CC(=CC=C21)CN2N=NC=1C2=NC(=CC1)NCCO Chemical compound C1(=CC=CC=C1)NC1=CC=C2C(=N1)N(N=N2)CC=2C=C1C=CC=NC1=CC2.N2=CC=CC1=CC(=CC=C21)CN2N=NC=1C2=NC(=CC1)NCCO RKUJPBFUCQBRTP-UHFFFAOYSA-N 0.000 claims 1
- HUPIYYWGUNFYQA-UHFFFAOYSA-N COC(C=CC(C1=CC=C2N=NN(CC(C=C3C=C4)=CC=C3N=C4NC(C=C3)=CC=C3C3=CC=C4N=NN(CC5=CC=C6N=CC=CC6=C5)C4=N3)C2=N1)=C1)=C1OC Chemical compound COC(C=CC(C1=CC=C2N=NN(CC(C=C3C=C4)=CC=C3N=C4NC(C=C3)=CC=C3C3=CC=C4N=NN(CC5=CC=C6N=CC=CC6=C5)C4=N3)C2=N1)=C1)=C1OC HUPIYYWGUNFYQA-UHFFFAOYSA-N 0.000 claims 1
- HJBFOVDCEJKURK-UHFFFAOYSA-N N1=CC=CC2=CC(=CC=C12)C(C)(C)N1N=NC=2C1=NC(=CC2)C=2C=NN(C2)CCO.N2=CC=CC1=CC=CC=C21 Chemical compound N1=CC=CC2=CC(=CC=C12)C(C)(C)N1N=NC=2C1=NC(=CC2)C=2C=NN(C2)CCO.N2=CC=CC1=CC=CC=C21 HJBFOVDCEJKURK-UHFFFAOYSA-N 0.000 claims 1
- PTQCZUCQIIDTLH-UHFFFAOYSA-N N1=CC=CC2=CC(=CC=C12)CN1N=NC=2C1=NC(=CC2)C(C)=O.O(C2=CC=CC=C2)C2=CC=C1C(=N2)N(N=N1)CC=1C=C2C=CC=NC2=CC1 Chemical compound N1=CC=CC2=CC(=CC=C12)CN1N=NC=2C1=NC(=CC2)C(C)=O.O(C2=CC=CC=C2)C2=CC=C1C(=N2)N(N=N1)CC=1C=C2C=CC=NC2=CC1 PTQCZUCQIIDTLH-UHFFFAOYSA-N 0.000 claims 1
- GSJADQZCDDDYJK-UHFFFAOYSA-N N1=CC=CC2=CC(=CC=C12)CN1N=NC=2C1=NC(=CC2)C2=CC=C(C=O)C=C2.N2=CC=CC1=CC(=CC=C21)CN2N=NC=1C2=NC(=CC1)C=1C=C(C=O)C=CC1 Chemical compound N1=CC=CC2=CC(=CC=C12)CN1N=NC=2C1=NC(=CC2)C2=CC=C(C=O)C=C2.N2=CC=CC1=CC(=CC=C21)CN2N=NC=1C2=NC(=CC1)C=1C=C(C=O)C=CC1 GSJADQZCDDDYJK-UHFFFAOYSA-N 0.000 claims 1
- GTLUBJXAXRRVMG-UHFFFAOYSA-N N1C=CC2=CC=C(C=C12)C1=CC=C2C(=N1)N(N=N2)CC=2C=C1C=CC=NC1=CC2.N2C=CC1=CC(=CC=C21)C2=CC=C1C(=N2)N(N=N1)CC=1C=C2C=CC=NC2=CC1 Chemical compound N1C=CC2=CC=C(C=C12)C1=CC=C2C(=N1)N(N=N2)CC=2C=C1C=CC=NC1=CC2.N2C=CC1=CC(=CC=C21)C2=CC=C1C(=N2)N(N=N1)CC=1C=C2C=CC=NC2=CC1 GTLUBJXAXRRVMG-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- KMBSLDHUDPDCBQ-UHFFFAOYSA-N [1-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]ethylideneamino]urea Chemical compound N1=CC=CC2=CC(CN3N=NC4=CC=C(N=C43)C(=NNC(N)=O)C)=CC=C21 KMBSLDHUDPDCBQ-UHFFFAOYSA-N 0.000 claims 1
- MZFIFYQYUZGDPI-UHFFFAOYSA-N [4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]thiophen-2-yl]methanol Chemical compound S1C(CO)=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=C1 MZFIFYQYUZGDPI-UHFFFAOYSA-N 0.000 claims 1
- MURJOSYVAGPAQD-UHFFFAOYSA-N [4-[3-[(4-fluorophenyl)methyl]triazolo[4,5-b]pyridin-5-yl]phenyl]methanol Chemical compound C1=CC(CO)=CC=C1C1=CC=C(N=NN2CC=3C=CC(F)=CC=3)C2=N1 MURJOSYVAGPAQD-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- KSSLZZVHAGGQFQ-UHFFFAOYSA-N methyl 2,6-difluoro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzoate Chemical compound C1=C(F)C(C(=O)OC)=C(F)C=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 KSSLZZVHAGGQFQ-UHFFFAOYSA-N 0.000 claims 1
- RSBOXYMVOHVEMI-UHFFFAOYSA-N methyl 2-chloro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 RSBOXYMVOHVEMI-UHFFFAOYSA-N 0.000 claims 1
- MKHLTJXMPGNSKU-UHFFFAOYSA-N methyl 2-chloro-4-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyridin-5-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC)=CC=C1C1=CC=C(N=NN2CC=3C(=CC4=NC=CC=C4C=3)F)C2=N1 MKHLTJXMPGNSKU-UHFFFAOYSA-N 0.000 claims 1
- XXNRZVVXHYGCPH-UHFFFAOYSA-N methyl 2-fluoro-4-[3-[(7-fluoroquinolin-6-yl)methyl]triazolo[4,5-b]pyridin-5-yl]benzoate Chemical compound C1=C(F)C(C(=O)OC)=CC=C1C1=CC=C(N=NN2CC=3C(=CC4=NC=CC=C4C=3)F)C2=N1 XXNRZVVXHYGCPH-UHFFFAOYSA-N 0.000 claims 1
- QINQZHIEGPUZBW-UHFFFAOYSA-N methyl 2-fluoro-5-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzoate Chemical compound C1=C(F)C(C(=O)OC)=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=C1 QINQZHIEGPUZBW-UHFFFAOYSA-N 0.000 claims 1
- IZVPOZNJDPRWCL-UHFFFAOYSA-N methyl 3-[2-fluoro-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]anilino]propanoate Chemical compound C1=C(F)C(NCCC(=O)OC)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 IZVPOZNJDPRWCL-UHFFFAOYSA-N 0.000 claims 1
- PBZOJLDUWZQLIV-UHFFFAOYSA-N methyl 3-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzoate Chemical compound COC(=O)C1=CC=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=C1 PBZOJLDUWZQLIV-UHFFFAOYSA-N 0.000 claims 1
- FGVXKWQRBSXXSX-UHFFFAOYSA-N methyl 4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 FGVXKWQRBSXXSX-UHFFFAOYSA-N 0.000 claims 1
- HFDSLIGWNYUQCZ-UHFFFAOYSA-N methyl 4-[3-[(2-chloro-3,6-difluorophenyl)methyl]triazolo[4,5-b]pyridin-5-yl]-2-fluorobenzoate Chemical compound C1=C(F)C(C(=O)OC)=CC=C1C1=CC=C(N=NN2CC=3C(=C(F)C=CC=3F)Cl)C2=N1 HFDSLIGWNYUQCZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- VRWGLCYXMBLWHN-UHFFFAOYSA-N n-[1-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]ethylideneamino]acetamide Chemical compound N1=CC=CC2=CC(CN3N=NC4=CC=C(N=C43)C(C)=NNC(=O)C)=CC=C21 VRWGLCYXMBLWHN-UHFFFAOYSA-N 0.000 claims 1
- ZUEJGCCADGGVFR-UHFFFAOYSA-N n-[1-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]ethylideneamino]pyridine-4-carboxamide Chemical compound C=1C=C2N=NN(CC=3C=C4C=CC=NC4=CC=3)C2=NC=1C(C)=NNC(=O)C1=CC=NC=C1 ZUEJGCCADGGVFR-UHFFFAOYSA-N 0.000 claims 1
- UVPUOLXMNDESPM-UHFFFAOYSA-N n-[3-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=C1 UVPUOLXMNDESPM-UHFFFAOYSA-N 0.000 claims 1
- UDZWLEIFSUEXEW-UHFFFAOYSA-N n-[4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 UDZWLEIFSUEXEW-UHFFFAOYSA-N 0.000 claims 1
- XSCNIMXHISBTPW-UHFFFAOYSA-N n-propan-2-yl-4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC(C)C)=CC=C1C1=CC=C(N=NN2CC=3C=C4C=CC=NC4=CC=3)C2=N1 XSCNIMXHISBTPW-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- BPKZMLAITURJBG-UHFFFAOYSA-N tert-butyl 3-ethyl-6-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]indazole-1-carboxylate Chemical compound N1=CC=CC2=CC(CN3N=NC4=CC=C(N=C43)C=3C=C4N(C(=O)OC(C)(C)C)N=C(C4=CC=3)CC)=CC=C21 BPKZMLAITURJBG-UHFFFAOYSA-N 0.000 claims 1
- ZPCUSVRPYLKXHE-UHFFFAOYSA-N tert-butyl 4-[4-[3-(quinolin-6-ylmethyl)triazolo[4,5-b]pyridin-5-yl]pyrazol-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N1N=CC(C=2N=C3N(CC=4C=C5C=CC=NC5=CC=4)N=NC3=CC=2)=C1 ZPCUSVRPYLKXHE-UHFFFAOYSA-N 0.000 claims 1
- CZWFKGHNFYZUGX-UHFFFAOYSA-N tert-butyl 4-[4-[3-[(2-chloro-3,6-difluorophenyl)methyl]triazolo[4,5-b]pyridin-5-yl]pyrazol-1-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N1N=CC(C=2N=C3N(CC=4C(=C(F)C=CC=4F)Cl)N=NC3=CC=2)=C1 CZWFKGHNFYZUGX-UHFFFAOYSA-N 0.000 claims 1
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| NZ604040A (en) | 2010-06-03 | 2015-02-27 | Pharmacyclics Inc | The use of inhibitors of bruton’s tyrosine kinase (btk) |
| US8906910B2 (en) | 2011-12-20 | 2014-12-09 | Glaxosmithkline Llc | Imidazopyridine derivatives as PI3 kinase |
| KR102164317B1 (ko) * | 2012-03-30 | 2020-10-13 | 리젠 파마슈티컬스 소시에떼 아노님 | C-met 단백질 키나제의 조절제로서의 신규한 3,5-디치환-3h-이미다조[4,5-b]피리딘 및 3,5- 디치환 -3h-[1,2,3]트리아졸로[4,5-b] 피리딘 화합물 |
| KR20150032340A (ko) | 2012-07-24 | 2015-03-25 | 파마시클릭스, 인코포레이티드 | 브루톤 티로신 키나제(btk)의 억제제에 대한 내성과 관련된 돌연변이 |
| EP3092235A2 (en) * | 2014-01-06 | 2016-11-16 | Rhizen Pharmaceuticals S.A. | Novel inhibitors of glutaminase |
| DK3174868T3 (da) | 2014-08-01 | 2021-11-08 | Nuevolution As | Forbindelser, der er aktive mod bromodomæner |
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