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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Families Citing this family (33)
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| NZ717373A (en) | 2010-06-03 | 2017-11-24 | Pharmacyclics Llc | The use of inhibitors of bruton’s tyrosine kinase (btk) |
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| BR112014024251A8 (pt) * | 2012-03-30 | 2018-01-23 | Rhizen Pharmaceuticals S A | novos compostos piridina 3,5-dissubstituída-3h-imidazo [4,5-b] e piridina 3,5-dissubstituída -3h-[1,2,3]triazolo[4,5-b] como moduladores de quinases de proteína c-met |
| US10954567B2 (en) | 2012-07-24 | 2021-03-23 | Pharmacyclics Llc | Mutations associated with resistance to inhibitors of Bruton's Tyrosine Kinase (BTK) |
| CN105960405B (zh) * | 2014-01-06 | 2021-02-19 | 理森制药股份公司 | 谷氨酰胺酶抑制剂 |
| KR102633122B1 (ko) | 2014-08-01 | 2024-02-05 | 누에볼루션 에이/에스 | 브로모도메인에 대하여 활성을 갖는 화합물 |
| US9950194B2 (en) | 2014-09-09 | 2018-04-24 | Mevion Medical Systems, Inc. | Patient positioning system |
| WO2016106381A1 (en) * | 2014-12-23 | 2016-06-30 | Pharmacyclics Llc | Btk inhibitor combinations and dosing regimen |
| HK1249104A1 (zh) | 2015-03-13 | 2018-10-26 | Forma Therapeutics, Inc. | 作为HDAC8抑制剂的α-肉桂酰胺化合物和组合物 |
| PH12017502322B1 (en) | 2015-06-25 | 2023-08-30 | Taiho Pharmaceutical Co Ltd | Therapeutic agent for fibrosis |
| CR20180109A (es) * | 2015-07-20 | 2018-05-03 | Genzyme Corp | Inhibidores de receptor del factor estimulador de colonias 1 (csf-1r) |
| TW202246215A (zh) | 2015-12-18 | 2022-12-01 | 美商亞德利克斯公司 | 作為非全身ｔｇｒ５促效劑之經取代之４－苯基吡啶化合物 |
| US12084472B2 (en) | 2015-12-18 | 2024-09-10 | Ardelyx, Inc. | Substituted 4-phenyl pyridine compounds as non-systemic TGR5 agonists |
| US9782370B2 (en) * | 2015-12-21 | 2017-10-10 | Gongwin Biopharm Holdings Co., Ltd. | Pharmaceutical compositions of benzenesulfonamide derivatives for treatment of adenoid cystic carcinoma |
| ES2921855T3 (es) * | 2016-04-07 | 2022-09-01 | Glaxosmithkline Ip Dev Ltd | Amidas heterocíclicas útiles como moduladores de proteínas |
| UA122819C2 (uk) | 2016-05-03 | 2021-01-06 | Байєр Фарма Акцієнгезелльшафт | Ароматичні сульфонамідні похідні |
| KR102323255B1 (ko) | 2017-02-15 | 2021-11-08 | 다이호야쿠힌고교 가부시키가이샤 | 의약 조성물 |
| WO2018210729A1 (en) | 2017-05-18 | 2018-11-22 | Bayer Pharma Aktiengesellschaft | Aromatic sulfonamide derivatives as antagonists or negative allosteric modulators of p2x4 receptor |
| AU2018329881B2 (en) | 2017-09-08 | 2021-12-02 | Taiho Pharmaceutical Co., Ltd. | Antitumor agent and antitumor effect potentiator |
| JP2021501178A (ja) | 2017-10-29 | 2021-01-14 | バイエル アクチェンゲゼルシャフトＢａｙｅｒ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 虚血性脳卒中の治療のための芳香族スルホンアミド誘導体 |
| CN110294751B (zh) * | 2018-03-21 | 2020-11-20 | 湖南化工研究院有限公司 | 具生物活性的咪唑[4,5-b]并吡啶类化合物及其制备方法和应用 |
| CN108822103A (zh) * | 2018-07-28 | 2018-11-16 | 刘凤娟 | 一种咪唑并[4,5-b]吡啶化合物及其制备方法和应用 |
| RS65335B1 (sr) | 2018-10-05 | 2024-04-30 | Annapurna Bio Inc | Jedinjenja i kompozicije za lečenje stanja povezanih sa aktivnošću receptora apj |
| EP3876939A4 (en) | 2018-11-07 | 2022-08-10 | Dana-Farber Cancer Institute, Inc. | Benzothiazole derivatives and 7-aza-benzothiazole derivatives as janus kinase 2 inhibitors and uses thereof |
| CN111116585B (zh) * | 2019-12-31 | 2021-02-05 | 北京鑫开元医药科技有限公司 | 具有c-MET激酶抑制活性化合物、制备方法、组合物及用途 |
| BR112022022409A2 (pt) | 2020-05-06 | 2023-02-07 | Ajax Therapeutics Inc | 6-heteroarilóxi benzimidazóis e azabenzimidazóis como inibidores de jak2 |
| EP4267574B1 (en) | 2020-12-23 | 2025-04-23 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as jak2 inhibitors |
| EP4267573A1 (en) | 2020-12-23 | 2023-11-01 | Genzyme Corporation | Deuterated colony stimulating factor-1 receptor (csf-1r) inhibitors |
| WO2023086320A1 (en) | 2021-11-09 | 2023-05-19 | Ajax Therapeutics, Inc. | Forms and compositions of inhibitors of jak2 |
| US11970494B2 (en) | 2021-11-09 | 2024-04-30 | Ajax Therapeutics, Inc. | 6-heteroaryloxy benzimidazoles and azabenzimidazoles as JAK2 inhibitors |
| CN118834216A (zh) * | 2022-07-15 | 2024-10-25 | 北京达尔文细胞生物科技有限公司 | 一种式ⅰ化合物的制备方法及其用于应激诱导细胞的应用 |
Family Cites Families (94)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3691016A (en) | 1970-04-17 | 1972-09-12 | Monsanto Co | Process for the preparation of insoluble enzymes |
| CA1023287A (en) | 1972-12-08 | 1977-12-27 | Boehringer Mannheim G.M.B.H. | Process for the preparation of carrier-bound proteins |
| US4179337A (en) | 1973-07-20 | 1979-12-18 | Davis Frank F | Non-immunogenic polypeptides |
| US4195128A (en) | 1976-05-03 | 1980-03-25 | Bayer Aktiengesellschaft | Polymeric carrier bound ligands |
| US4330440A (en) | 1977-02-08 | 1982-05-18 | Development Finance Corporation Of New Zealand | Activated matrix and method of activation |
| CA1093991A (en) | 1977-02-17 | 1981-01-20 | Hideo Hirohara | Enzyme immobilization with pullulan gel |
| US4229537A (en) | 1978-02-09 | 1980-10-21 | New York University | Preparation of trichloro-s-triazine activated supports for coupling ligands |
| US4289872A (en) | 1979-04-06 | 1981-09-15 | Allied Corporation | Macromolecular highly branched homogeneous compound based on lysine units |
| JPS6023084B2 (ja) | 1979-07-11 | 1985-06-05 | 味の素株式会社 | 代用血液 |
| US4640835A (en) | 1981-10-30 | 1987-02-03 | Nippon Chemiphar Company, Ltd. | Plasminogen activator derivatives |
| FR2527608B1 (fr) * | 1982-05-28 | 1986-10-10 | Sandoz Sa | Nouveaux composes heterocycliques, leur preparation et leur utilisation comme medicaments |
| BE896797A (fr) * | 1982-05-28 | 1983-11-21 | Sandoz Sa | Nouveaux composes heterocycliques, leur preparation et leur utilisation comme medicaments. |
| US4496689A (en) | 1983-12-27 | 1985-01-29 | Miles Laboratories, Inc. | Covalently attached complex of alpha-1-proteinase inhibitor with a water soluble polymer |
| DE3675588D1 (de) | 1985-06-19 | 1990-12-20 | Ajinomoto Kk | Haemoglobin, das an ein poly(alkenylenoxid) gebunden ist. |
| US4791192A (en) | 1986-06-26 | 1988-12-13 | Takeda Chemical Industries, Ltd. | Chemically modified protein with polyethyleneglycol |
| CH671155A5 (enExample) | 1986-08-18 | 1989-08-15 | Clinical Technologies Ass | |
| US5229490A (en) | 1987-05-06 | 1993-07-20 | The Rockefeller University | Multiple antigen peptide system |
| GB8827305D0 (en) | 1988-11-23 | 1988-12-29 | British Bio Technology | Compounds |
| IL94390A (en) * | 1989-05-30 | 1996-03-31 | Merck & Co Inc | The 6-membered trans-nitrogen-containing heterocycles are compressed with imidazo and pharmaceutical preparations containing them |
| US5013556A (en) | 1989-10-20 | 1991-05-07 | Liposome Technology, Inc. | Liposomes with enhanced circulation time |
| EP0470543A1 (de) * | 1990-08-10 | 1992-02-12 | Dr. Karl Thomae GmbH | Heterocyclische Imidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zur ihrer Herstellung |
| WO1993021259A1 (en) | 1992-04-14 | 1993-10-28 | Cornell Research Foundation Inc. | Dendritic based macromolecules and method of production |
| US5646176A (en) | 1992-12-24 | 1997-07-08 | Bristol-Myers Squibb Company | Phosphonooxymethyl ethers of taxane derivatives |
| US5455258A (en) | 1993-01-06 | 1995-10-03 | Ciba-Geigy Corporation | Arylsulfonamido-substituted hydroxamic acids |
| US5863949A (en) | 1995-03-08 | 1999-01-26 | Pfizer Inc | Arylsulfonylamino hydroxamic acid derivatives |
| FI973974A7 (fi) | 1995-04-20 | 1997-10-16 | Pfizer | Aryylisulfonyylihydroksaamihappojohdannaisia MMP- ja TNF-inhibiittorei na |
| DE69624081T2 (de) | 1995-12-20 | 2003-06-12 | Agouron Pharmaceuticals, Inc. | Matrix-metalloprotease Inhibitoren |
| HUP9903014A3 (en) | 1996-07-18 | 2000-08-28 | Pfizer | Phosphinate derivatives having matrix metalloprotease inhibitor effect and medicaments containing the same |
| IL128189A0 (en) | 1996-08-23 | 1999-11-30 | Pfizer | Arylsulfonylamino hydroxamic acid derivatives |
| ES2224277T3 (es) | 1997-01-06 | 2005-03-01 | Pfizer Inc. | Derivados de sulfonas ciclicas. |
| PT977733E (pt) | 1997-02-03 | 2003-12-31 | Pfizer Prod Inc | Derivados de acido arilsulfonilamino-hidroxamico |
| JP2000507975A (ja) | 1997-02-07 | 2000-06-27 | ファイザー・インク | Ｎ−ヒドロキシ−β−スルホニルプロピオンアミド誘導体類及びそれらのマトリックスメタロプロテイナーゼ阻害薬としての使用 |
| IL131123A0 (en) | 1997-02-11 | 2001-01-28 | Pfizer | Arylsulfonyl hydroxamic acid derivatives |
| US6605599B1 (en) | 1997-07-08 | 2003-08-12 | Bristol-Myers Squibb Company | Epothilone derivatives |
| GB9725782D0 (en) | 1997-12-05 | 1998-02-04 | Pfizer Ltd | Therapeutic agents |
| GB9801690D0 (en) | 1998-01-27 | 1998-03-25 | Pfizer Ltd | Therapeutic agents |
| PA8469501A1 (es) | 1998-04-10 | 2000-09-29 | Pfizer Prod Inc | Hidroxamidas del acido (4-arilsulfonilamino)-tetrahidropiran-4-carboxilico |
| PA8469401A1 (es) | 1998-04-10 | 2000-05-24 | Pfizer Prod Inc | Derivados biciclicos del acido hidroxamico |
| ATE254615T1 (de) | 1999-02-22 | 2003-12-15 | Biotechnolog Forschung Gmbh | C-21 modifizierte epothilone |
| UA75055C2 (uk) * | 1999-11-30 | 2006-03-15 | Пфайзер Продактс Інк. | Похідні бензоімідазолу, що використовуються як антипроліферативний засіб, фармацевтична композиція на їх основі |
| US7579453B2 (en) | 2003-06-19 | 2009-08-25 | The United States Of America As Represented By The Secretary Of The Dapartment Of Health And Human Services | Variants of human taste receptor genes |
| US7250417B2 (en) * | 2003-07-02 | 2007-07-31 | Sugen Inc. | Arylmethyl triazolo- and imidazopyrazines as c-Met inhibitors |
| DE602004012578T2 (de) | 2003-08-15 | 2008-12-11 | Vertex Pharmaceuticals Inc., Cambridge | Als inhibitoren von c-met geeignete pyrrolzusammensetzungen |
| AR045595A1 (es) | 2003-09-04 | 2005-11-02 | Vertex Pharma | Composiciones utiles como inhibidores de proteinas quinasas |
| AU2004284420A1 (en) | 2003-09-24 | 2005-05-06 | Vertex Pharmaceuticals Incorporated | 4-azole substituted imidazole compositions useful as inhibitors or c-Met receptor tyrosine kinase |
| ES2436888T3 (es) | 2003-09-26 | 2014-01-07 | Exelixis, Inc | Moduladores c-Met y métodos de uso |
| TWI332003B (en) | 2004-01-30 | 2010-10-21 | Lilly Co Eli | Kinase inhibitors |
| US7459562B2 (en) | 2004-04-23 | 2008-12-02 | Bristol-Myers Squibb Company | Monocyclic heterocycles as kinase inhibitors |
| US20050288290A1 (en) | 2004-06-28 | 2005-12-29 | Borzilleri Robert M | Fused heterocyclic kinase inhibitors |
| US7432373B2 (en) | 2004-06-28 | 2008-10-07 | Bristol-Meyers Squibb Company | Processes and intermediates useful for preparing fused heterocyclic kinase inhibitors |
| US7439246B2 (en) | 2004-06-28 | 2008-10-21 | Bristol-Myers Squibb Company | Fused heterocyclic kinase inhibitors |
| EP1773826A4 (en) | 2004-07-02 | 2009-06-03 | Exelixis Inc | MODULATORS OF C-MET AND THEIR METHOD OF USE |
| MX2007002312A (es) | 2004-08-26 | 2007-04-16 | Pfizer | Compuestos de aminoheteroarilo enantiomericamente puros como inhibidores de proteina quinasa. |
| EP1786777A1 (en) | 2004-08-26 | 2007-05-23 | Pfizer, Inc. | Aminoheteroaryl compounds as protein tyrosine kinase inhibitors |
| DK1784396T3 (da) | 2004-08-26 | 2011-02-14 | Pfizer | Pyrazol-substituerede aminoheteroaryl-forbindelser som proteinkinase-inhibitorer |
| US7528138B2 (en) | 2004-11-04 | 2009-05-05 | Vertex Pharmaceuticals Incorporated | Pyrazolo[1,5-a]pyrimidines useful as inhibitors of protein kinases |
| US7884109B2 (en) * | 2005-04-05 | 2011-02-08 | Wyeth Llc | Purine and imidazopyridine derivatives for immunosuppression |
| CA2603748A1 (en) | 2005-04-06 | 2006-10-12 | Exelixis, Inc. | C-met modulators and methods of use |
| US7470693B2 (en) | 2005-04-21 | 2008-12-30 | Bristol-Myers Squibb Company | Oxalamide derivatives as kinase inhibitors |
| JO2787B1 (en) | 2005-04-27 | 2014-03-15 | امجين إنك, | Alternative amide derivatives and methods of use |
| WO2006128693A2 (en) * | 2005-06-01 | 2006-12-07 | Ucb Pharma, S.A. | 2 -oxo-i -pyrrolidine derivatives/ processes for preparing them and their therapeutic use on the central nervous system |
| US7348325B2 (en) | 2005-11-30 | 2008-03-25 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| KR20080080584A (ko) | 2005-11-30 | 2008-09-04 | 버텍스 파마슈티칼스 인코포레이티드 | ｃ-Ｍｅｔ의 억제제 및 이의 용도 |
| EP2004625B1 (en) | 2006-03-22 | 2009-12-30 | Vertex Pharmaceuticals Incorporated | C-met protein kinase inhibitors for the treatment of proliferative disorders |
| NL2000613C2 (nl) * | 2006-05-11 | 2007-11-20 | Pfizer Prod Inc | Triazoolpyrazinederivaten. |
| TW200813021A (en) | 2006-07-10 | 2008-03-16 | Merck & Co Inc | Tyrosine kinase inhibitors |
| WO2008021781A1 (en) * | 2006-08-07 | 2008-02-21 | Incyte Corporation | Triazolotriazines as kinase inhibitors |
| US8481538B2 (en) | 2006-09-18 | 2013-07-09 | Vertex Pharmaceuticals Incorporated | Heterocyclic inhibitors of c-Met and uses thereof |
| AU2007309237B2 (en) | 2006-10-23 | 2012-03-22 | Sgx Pharmaceuticals, Inc. | Triazolo-pyridazine protein kinase modulators |
| US9206142B2 (en) | 2006-10-31 | 2015-12-08 | Merck Sharp & Dohme Corp. | Anilinopiperazine derivatives and methods of use thereof |
| WO2008060866A1 (en) | 2006-11-14 | 2008-05-22 | Smithkline Beecham Corporation | Novel compounds |
| US20080119496A1 (en) * | 2006-11-16 | 2008-05-22 | Pharmacopeia Drug Discovery, Inc. | 7-Substituted Purine Derivatives for Immunosuppression |
| CA2669991C (en) | 2006-11-22 | 2016-01-26 | Incyte Corporation | Imidazotriazines and imidazopyrimidines as kinase inhibitors |
| WO2008078085A1 (en) | 2006-12-22 | 2008-07-03 | Astrazeneca Ab | Method |
| WO2008088881A1 (en) | 2007-01-19 | 2008-07-24 | Xcovery, Inc. | Kinase inhibitor compounds |
| JPWO2008102870A1 (ja) | 2007-02-23 | 2010-05-27 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | Ｈｇｆｒ遺伝子増幅細胞株に優れた細胞増殖阻害効果および抗腫瘍効果を示すピリジン誘導体またはピリミジン誘導体 |
| FR2915199B1 (fr) * | 2007-04-18 | 2010-01-22 | Sanofi Aventis | Derives de triazolopyridine-carboxamides et triazolopyrimidine-carboxamides, leur preparation et leur application en therapeutique. |
| FR2915198B1 (fr) * | 2007-04-18 | 2009-12-18 | Sanofi Aventis | Derives de triazolopyridine-carboxamides et triazolopyridine -carboxamides, leur preparation et leur application en therapeutique. |
| JP5425060B2 (ja) | 2007-06-22 | 2014-02-26 | アークル インコーポレイテッド | ピロリジノン、ピロリジン−２，５−ジオン、ピロリジンおよびチオスクシンイミド誘導体、癌の治療のための組成物および方法 |
| WO2009014012A1 (ja) | 2007-07-25 | 2009-01-29 | Kyouwagiken Co., Ltd. | ボール回転調節装置、発射装置用アタッチメント、ボール発射装置 |
| JP5224616B2 (ja) | 2007-10-29 | 2013-07-03 | メルク・シャープ・アンド・ドーム・コーポレーション | プロテインキナーゼ阻害剤としての複素環式エーテルまたはチオエーテル誘導体 |
| WO2009058728A1 (en) | 2007-10-29 | 2009-05-07 | Schering Corporation | Thiazole derivatives as protein kinase inhibitors |
| EP2217595A1 (en) | 2007-10-29 | 2010-08-18 | Schering Corporation | Diamido thiazole derivatives as protein kinase inhibitors |
| MX2010004880A (es) | 2007-10-29 | 2010-07-28 | Schering Corp | Derivados heterociclicos de urea y tiourea, y metodos de uso de los mismos. |
| JP2011515343A (ja) * | 2008-03-03 | 2011-05-19 | タイガー ファーマテック | チロシンキナーゼ阻害薬 |
| WO2009140128A2 (en) * | 2008-05-13 | 2009-11-19 | Irm Llc | Compounds and compositions as kinase inhibitors |
| JPWO2009157196A1 (ja) * | 2008-06-25 | 2011-12-08 | 武田薬品工業株式会社 | アミド化合物 |
| UY32049A (es) * | 2008-08-14 | 2010-03-26 | Takeda Pharmaceutical | Inhibidores de cmet |
| DE102008037790A1 (de) * | 2008-08-14 | 2010-02-18 | Merck Patent Gmbh | Bicyclische Triazolderivate |
| EA201200260A1 (ru) * | 2009-08-12 | 2012-09-28 | Новартис Аг | Гетероциклические гидразоны и их применение для лечения рака и воспаления |
| KR20120089463A (ko) * | 2009-08-20 | 2012-08-10 | 노파르티스 아게 | 헤테로시클릭 옥심 화합물 |
| BR112012016129B1 (pt) * | 2009-12-31 | 2020-11-03 | Hutchison Medipharma Limited | composto, composição e uso dos ditos compostos |
| JP5960688B2 (ja) * | 2010-05-17 | 2016-08-02 | インコゼン セラピューティクス プライベート リミテッド | プロテインキナーゼ調節物質としての新規３，５−二置換−３ｈ−［１，２，３］トリアゾロ［４，５−ｂ］ピリジン化合物 |
| BR112014024251A8 (pt) * | 2012-03-30 | 2018-01-23 | Rhizen Pharmaceuticals S A | novos compostos piridina 3,5-dissubstituída-3h-imidazo [4,5-b] e piridina 3,5-dissubstituída -3h-[1,2,3]triazolo[4,5-b] como moduladores de quinases de proteína c-met |
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