JP2020511452A5 - - Google Patents
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- JP2020511452A5 JP2020511452A5 JP2019548905A JP2019548905A JP2020511452A5 JP 2020511452 A5 JP2020511452 A5 JP 2020511452A5 JP 2019548905 A JP2019548905 A JP 2019548905A JP 2019548905 A JP2019548905 A JP 2019548905A JP 2020511452 A5 JP2020511452 A5 JP 2020511452A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- substituted
- unsubstituted
- aminopiperidin
- methylphenyl
- 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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- -1 4-Aminopiperidin-1-yl Chemical group 0.000 claims 157
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 45
- 229910052739 hydrogen Inorganic materials 0.000 claims 30
- 239000001257 hydrogen Substances 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 19
- 150000002431 hydrogen Chemical class 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 19
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 239000000203 mixture Substances 0.000 claims 18
- 239000012453 solvate Substances 0.000 claims 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 11
- 125000002950 monocyclic group Chemical group 0.000 claims 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 9
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 8
- 229910052801 chlorine Inorganic materials 0.000 claims 8
- 229910052731 fluorine Inorganic materials 0.000 claims 8
- 229910052794 bromium Inorganic materials 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000003944 tolyl group Chemical group 0.000 claims 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- 125000002393 azetidinyl group Chemical group 0.000 claims 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 6
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 5
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 3
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- XBLIVYAMTPLMAP-UHFFFAOYSA-N 6-fluoro-4-methoxy-1H-benzimidazole Chemical compound COc1cc(F)cc2[nH]cnc12 XBLIVYAMTPLMAP-UHFFFAOYSA-N 0.000 claims 2
- 125000003725 azepanyl group Chemical group 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- UPEDCKFLNFMCCW-YLJYHZDGSA-N (3R,4R)-4-amino-1-[2-amino-3-(6-chloro-1H-benzimidazol-2-yl)-5-(3,5-dimethylphenyl)pyridin-4-yl]piperidine-3-carbonitrile Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C(=NC=C1C1=CC(=CC(=C1)C)C)N)C1=NC2=C(N1)C=CC(=C2)Cl)C#N UPEDCKFLNFMCCW-YLJYHZDGSA-N 0.000 claims 1
- BHPQOEOAPQDIEN-UHFFFAOYSA-N 1-[2-(3-fluoroazetidin-1-yl)-3-(6-fluoro-4-methoxy-1H-benzimidazol-2-yl)-5-(3-fluorophenyl)pyridin-4-yl]piperidin-4-amine Chemical compound FC1=CC2=C(NC(=N2)C=2C(=NC=C(C=2N2CCC(CC2)N)C2=CC(=CC=C2)F)N2CC(C2)F)C(=C1)OC BHPQOEOAPQDIEN-UHFFFAOYSA-N 0.000 claims 1
- RNQZIASPEMRGMD-UHFFFAOYSA-N 1-[2-[2-amino-4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-3H-benzimidazol-5-yl]-3-methoxyurea Chemical compound CONC(=O)NC1=CC=C2NC(=NC2=C1)C1=C(N2CCC(N)CC2)C(=CN=C1N)C1=CC(F)=CC(C)=C1 RNQZIASPEMRGMD-UHFFFAOYSA-N 0.000 claims 1
- JQVMUGNWAUNANO-UHFFFAOYSA-N 2-[2-amino-4-(4-aminopiperidin-1-yl)-5-(3-chloro-5-fluorophenyl)pyridin-3-yl]-7-fluoro-3H-benzimidazole-5-carbonitrile Chemical compound NC1CCN(CC1)C1=C(C2=NC3=CC(=CC(F)=C3N2)C#N)C(N)=NC=C1C1=CC(Cl)=CC(F)=C1 JQVMUGNWAUNANO-UHFFFAOYSA-N 0.000 claims 1
- VAERIDPTRUIBSE-UHFFFAOYSA-N 2-[2-amino-4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-1H-benzimidazole-4-carbonitrile Chemical compound NC1=NC=C(C(=C1C1=NC2=C(N1)C(=CC=C2)C#N)N1CCC(CC1)N)C1=CC(=CC(=C1)C)F VAERIDPTRUIBSE-UHFFFAOYSA-N 0.000 claims 1
- FNHZZNBSQHPAKT-UHFFFAOYSA-N 2-[2-amino-4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-1H-indole-6-carbonitrile Chemical compound NC1=NC=C(C(=C1C=1NC2=CC(=CC=C2C=1)C#N)N1CCC(CC1)N)C1=CC(=CC(=C1)C)F FNHZZNBSQHPAKT-UHFFFAOYSA-N 0.000 claims 1
- FHSLBGSYYAWDBT-UHFFFAOYSA-N 2-[2-amino-4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-3H-benzimidazole-5-carbonitrile Chemical compound CC1=CC(=CC(F)=C1)C1=CN=C(N)C(C2=NC3=CC(=CC=C3N2)C#N)=C1N1CCC(N)CC1 FHSLBGSYYAWDBT-UHFFFAOYSA-N 0.000 claims 1
- DZGSAKAITIIKBV-UHFFFAOYSA-N 2-[2-amino-4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-3H-benzimidazole-5-sulfonamide Chemical compound NC1=NC=C(C(=C1C1=NC2=C(N1)C=CC(=C2)S(=O)(=O)N)N1CCC(CC1)N)C1=CC(=CC(=C1)C)F DZGSAKAITIIKBV-UHFFFAOYSA-N 0.000 claims 1
- UQAUUASAHIERPH-UHFFFAOYSA-N 2-[2-amino-4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-7-fluoro-3H-benzimidazole-5-carbonitrile Chemical compound CC1=CC(=CC(F)=C1)C1=CN=C(N)C(C2=NC3=CC(=CC(F)=C3N2)C#N)=C1N1CCC(N)CC1 UQAUUASAHIERPH-UHFFFAOYSA-N 0.000 claims 1
- AQSNQZCNKFIIDY-UHFFFAOYSA-N 2-[2-amino-4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-N-methoxy-1H-benzimidazole-4-carboxamide Chemical compound CONC(=O)C1=C2NC(=NC2=CC=C1)C1=C(N2CCC(N)CC2)C(=CN=C1N)C1=CC(F)=CC(C)=C1 AQSNQZCNKFIIDY-UHFFFAOYSA-N 0.000 claims 1
- RIMFGGAVAYMNAK-UHFFFAOYSA-N 2-[2-amino-4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-N-methoxy-3H-benzimidazole-5-carboxamide Chemical compound CONC(=O)C1=CC=C2NC(=NC2=C1)C1=C(N2CCC(N)CC2)C(=CN=C1N)C1=CC(F)=CC(C)=C1 RIMFGGAVAYMNAK-UHFFFAOYSA-N 0.000 claims 1
- VVWLOPLWSLRSRY-UHFFFAOYSA-N 2-[2-amino-4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-N-methoxy-N-methyl-1H-benzimidazole-4-carboxamide Chemical compound CON(C)C(=O)C1=C2NC(=NC2=CC=C1)C1=C(N2CCC(N)CC2)C(=CN=C1N)C1=CC(F)=CC(C)=C1 VVWLOPLWSLRSRY-UHFFFAOYSA-N 0.000 claims 1
- BHLHRRWJFILZDL-UHFFFAOYSA-N 2-[2-amino-4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-N-methoxy-N-methyl-3H-benzimidazole-5-carboxamide Chemical compound CON(C)C(=O)C1=CC=C2NC(=NC2=C1)C1=C(N2CCC(N)CC2)C(=CN=C1N)C1=CC(F)=CC(C)=C1 BHLHRRWJFILZDL-UHFFFAOYSA-N 0.000 claims 1
- KWRWJULQKJUGLI-UHFFFAOYSA-N 2-[2-amino-5-(3-fluoro-5-methylphenyl)-4-[4-(methylamino)piperidin-1-yl]pyridin-3-yl]-3H-benzimidazole-5-carbonitrile Chemical compound NC1=NC=C(C(=C1C1=NC2=C(N1)C=C(C=C2)C#N)N1CCC(CC1)NC)C1=CC(=CC(=C1)C)F KWRWJULQKJUGLI-UHFFFAOYSA-N 0.000 claims 1
- UKYJACPWBRHJGK-UHFFFAOYSA-N 2-[2-amino-5-(3-fluoro-5-methylphenyl)-4-[4-(methylamino)piperidin-1-yl]pyridin-3-yl]-7-fluoro-3H-benzimidazole-5-carbonitrile Chemical compound CNC1CCN(CC1)C1=C(C2=NC3=CC(=CC(F)=C3N2)C#N)C(N)=NC=C1C1=CC(F)=CC(C)=C1 UKYJACPWBRHJGK-UHFFFAOYSA-N 0.000 claims 1
- HHIKXRXMRPUQJN-UHFFFAOYSA-N 2-[4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)-2-(methylamino)pyridin-3-yl]-3H-benzimidazole-5-carbonitrile Chemical compound NC1CCN(CC1)C1=C(C(=NC=C1C1=CC(=CC(=C1)C)F)NC)C1=NC2=C(N1)C=C(C=C2)C#N HHIKXRXMRPUQJN-UHFFFAOYSA-N 0.000 claims 1
- SIPCJCPKIFBIIU-UHFFFAOYSA-N 2-[4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)-2-(methylamino)pyridin-3-yl]-7-fluoro-3H-benzimidazole-5-carbonitrile Chemical compound CNC1=NC=C(C2=CC(F)=CC(C)=C2)C(N2CCC(N)CC2)=C1C1=NC2=CC(=CC(F)=C2N1)C#N SIPCJCPKIFBIIU-UHFFFAOYSA-N 0.000 claims 1
- VXEKZTDHOQMNBL-UHFFFAOYSA-N 2-[[2-[2-amino-4-(4-aminopiperidin-1-yl)-5-(3-chloro-5-fluorophenyl)pyridin-3-yl]-6-fluoro-1H-benzimidazol-4-yl]oxy]acetonitrile Chemical compound NC1=NC=C(C(=C1C1=NC2=C(N1)C(=CC(=C2)F)OCC#N)N1CCC(CC1)N)C1=CC(=CC(=C1)F)Cl VXEKZTDHOQMNBL-UHFFFAOYSA-N 0.000 claims 1
- RTNVXWYTPYYQLA-UHFFFAOYSA-N 2-[[2-[2-amino-4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-6-fluoro-1H-benzimidazol-4-yl]oxy]acetonitrile Chemical compound NC1=NC=C(C(=C1C1=NC2=C(N1)C(=CC(=C2)F)OCC#N)N1CCC(CC1)N)C1=CC(=CC(=C1)C)F RTNVXWYTPYYQLA-UHFFFAOYSA-N 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- DAIDKJOASFVEQF-UHFFFAOYSA-N 3-(4,6-difluoro-1H-benzimidazol-2-yl)-5-(3-fluoro-5-methylphenyl)-N-(2-methoxyethyl)-4-(4-methylpiperidin-1-yl)pyridin-2-amine Chemical compound COCCNC1=NC=C(C2=CC(F)=CC(C)=C2)C(N2CCC(C)CC2)=C1C1=NC2=CC(F)=CC(F)=C2N1 DAIDKJOASFVEQF-UHFFFAOYSA-N 0.000 claims 1
- GDQRETLEEBQLMT-UHFFFAOYSA-N 3-[6-amino-4-(4-aminopiperidin-1-yl)-5-(6-chloro-1H-benzimidazol-2-yl)pyridin-3-yl]-5-fluorobenzonitrile Chemical compound NC1=C(C(=C(C=N1)C=1C=C(C#N)C=C(C=1)F)N1CCC(CC1)N)C1=NC2=C(N1)C=CC(=C2)Cl GDQRETLEEBQLMT-UHFFFAOYSA-N 0.000 claims 1
- QPWNHOBXMRLINT-UHFFFAOYSA-N 3-[6-amino-4-(4-aminopiperidin-1-yl)-5-(6-chloro-1H-benzimidazol-2-yl)pyridin-3-yl]-5-methylbenzonitrile Chemical compound CC1=CC(=CC(=C1)C1=C(N2CCC(N)CC2)C(C2=NC3=CC(Cl)=CC=C3N2)=C(N)N=C1)C#N QPWNHOBXMRLINT-UHFFFAOYSA-N 0.000 claims 1
- RMKROKPQNXLVHF-UHFFFAOYSA-N 4-(4-aminopiperidin-1-yl)-3-(6-chloro-1H-benzimidazol-2-yl)-5-(3,5-difluorophenyl)pyridin-2-amine Chemical compound NC1CCN(CC1)C1=C(C2=NC3=CC(Cl)=CC=C3N2)C(N)=NC=C1C1=CC(F)=CC(F)=C1 RMKROKPQNXLVHF-UHFFFAOYSA-N 0.000 claims 1
- GQHVMPHABBGKIR-UHFFFAOYSA-N 4-(4-aminopiperidin-1-yl)-3-[4-fluoro-6-(methoxyiminomethyl)-1H-benzimidazol-2-yl]-5-(3-fluoro-5-methylphenyl)pyridin-2-amine Chemical compound CON=CC1=CC(F)=C2NC(=NC2=C1)C1=C(N2CCC(N)CC2)C(=CN=C1N)C1=CC(F)=CC(C)=C1 GQHVMPHABBGKIR-UHFFFAOYSA-N 0.000 claims 1
- IIZKCNRWUFGQEY-UHFFFAOYSA-N 4-(4-aminopiperidin-1-yl)-3-[6-(3-fluoroazetidin-1-yl)-1H-benzimidazol-2-yl]-5-(3-fluoro-5-methylphenyl)pyridin-2-amine Chemical compound NC1CCN(CC1)C1=C(C(=NC=C1C1=CC(=CC(=C1)C)F)N)C1=NC2=C(N1)C=CC(=C2)N1CC(C1)F IIZKCNRWUFGQEY-UHFFFAOYSA-N 0.000 claims 1
- RNVYYQFTBLLDMB-UHFFFAOYSA-N 4-(4-aminopiperidin-1-yl)-5-(3-chlorophenyl)-3-(6-fluoro-4-methoxy-1H-benzimidazol-2-yl)pyridin-2-amine Chemical compound COC1=C2NC(=NC2=CC(F)=C1)C1=C(N2CCC(N)CC2)C(=CN=C1N)C1=CC(Cl)=CC=C1 RNVYYQFTBLLDMB-UHFFFAOYSA-N 0.000 claims 1
- WNJNHLCJFAEHEU-UHFFFAOYSA-N 4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)-3-[4-(methoxyiminomethyl)-1H-benzimidazol-2-yl]pyridin-2-amine Chemical compound NC1CCN(CC1)C1=C(C(=NC=C1C1=CC(=CC(=C1)C)F)N)C1=NC2=C(N1)C=CC=C2C=NOC WNJNHLCJFAEHEU-UHFFFAOYSA-N 0.000 claims 1
- FHPZKWYAJPTFOS-UHFFFAOYSA-N 4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)-3-[4-methoxy-6-(methoxyiminomethyl)-1H-benzimidazol-2-yl]pyridin-2-amine Chemical compound NC1CCN(CC1)C1=C(C(=NC=C1C1=CC(=CC(=C1)C)F)N)C1=NC2=C(N1)C(=CC(=C2)C=NOC)OC FHPZKWYAJPTFOS-UHFFFAOYSA-N 0.000 claims 1
- CBWYBTLUFUXRJZ-UHFFFAOYSA-N 4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)-3-[6-(methoxyiminomethyl)-1H-benzimidazol-2-yl]pyridin-2-amine Chemical compound NC1CCN(CC1)C1=C(C(=NC=C1C1=CC(=CC(=C1)C)F)N)C1=NC2=C(N1)C=CC(=C2)C=NOC CBWYBTLUFUXRJZ-UHFFFAOYSA-N 0.000 claims 1
- SIPXGGQRWBQNNJ-UHFFFAOYSA-N 4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)-3-[6-(oxetan-3-yloxy)-1H-benzimidazol-2-yl]pyridin-2-amine Chemical compound CC1=CC(=CC(F)=C1)C1=CN=C(N)C(C2=NC3=CC(OC4COC4)=CC=C3N2)=C1N1CCC(N)CC1 SIPXGGQRWBQNNJ-UHFFFAOYSA-N 0.000 claims 1
- YDTVBQXYEODCTA-UHFFFAOYSA-N 4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)-3-[6-(trifluoromethoxy)-1H-benzimidazol-2-yl]pyridin-2-amine Chemical compound CC1=CC(=CC(F)=C1)C1=CN=C(N)C(C2=NC3=CC(OC(F)(F)F)=CC=C3N2)=C1N1CCC(N)CC1 YDTVBQXYEODCTA-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 1
- GOBPXOLEZBCACY-UHFFFAOYSA-N N-[[2-[2-amino-4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-1H-benzimidazol-4-yl]methylidene]hydroxylamine Chemical compound CC1=CC(=CC(F)=C1)C1=CN=C(N)C(C2=NC3=CC=CC(C=NO)=C3N2)=C1N1CCC(N)CC1 GOBPXOLEZBCACY-UHFFFAOYSA-N 0.000 claims 1
- ABTRZMHTQMQNTF-UHFFFAOYSA-N N-[[2-[2-amino-4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-1H-imidazo[4,5-b]pyridin-7-yl]methylidene]hydroxylamine Chemical compound NC1CCN(CC1)C1=C(C(=NC=C1C1=CC(=CC(=C1)C)F)N)C1=NC=2C(=NC=CC=2C=NO)N1 ABTRZMHTQMQNTF-UHFFFAOYSA-N 0.000 claims 1
- OIFPARSJWXUKOU-UHFFFAOYSA-N N-[[2-[2-amino-4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-1H-imidazo[4,5-c]pyridin-4-yl]methylidene]hydroxylamine Chemical compound NC1CCN(CC1)C1=C(C(=NC=C1C1=CC(=CC(=C1)C)F)N)C=1NC2=C(C(=NC=C2)C=NO)N=1 OIFPARSJWXUKOU-UHFFFAOYSA-N 0.000 claims 1
- ZQIIPQDMLNZSIN-UHFFFAOYSA-N N-[[2-[2-amino-4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-3H-benzimidazol-5-yl]methylidene]hydroxylamine Chemical compound NC1CCN(CC1)C1=C(C(=NC=C1C1=CC(=CC(=C1)C)F)N)C1=NC2=C(N1)C=CC(=C2)C=NO ZQIIPQDMLNZSIN-UHFFFAOYSA-N 0.000 claims 1
- MYYPRDNTMOEGPP-UHFFFAOYSA-N N-[[2-[2-amino-4-(4-aminopiperidin-1-yl)-5-(3-fluoro-5-methylphenyl)pyridin-3-yl]-6-fluoro-1H-benzimidazol-4-yl]methylidene]hydroxylamine Chemical compound CC1=CC(=CC(F)=C1)C1=CN=C(N)C(C2=NC3=C(C=NO)C=C(F)C=C3N2)=C1N1CCC(N)CC1 MYYPRDNTMOEGPP-UHFFFAOYSA-N 0.000 claims 1
- ZKAKSICHWCVRGU-UHFFFAOYSA-N N-[[2-amino-4-(4-aminopiperidin-1-yl)-5-(3-chloro-5-methylphenyl)pyridin-3-yl]methylidene]hydroxylamine Chemical compound NC1CCN(CC1)C1=C(C(=NC=C1C1=CC(=CC(=C1)C)Cl)N)C=NO ZKAKSICHWCVRGU-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 108050001286 Somatostatin Receptor Proteins 0.000 claims 1
- 102000011096 Somatostatin receptor Human genes 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004212 difluorophenyl group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
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| JP7365347B2 (ja) * | 2018-02-12 | 2023-10-19 | クリネティックス ファーマシューティカルズ，インク． | ソマトスタチンモジュレーターおよびその使用 |
| WO2019240246A1 (ja) * | 2018-06-15 | 2019-12-19 | 小野薬品工業株式会社 | ピペリジノール誘導体の新規な塩および新規結晶形 |
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| TWI841768B (zh) | 2019-08-14 | 2024-05-11 | 美商克林提克斯醫藥股份有限公司 | 非肽生長抑制素(somatostatin)5型受體激動劑及其用途 |
| WO2021076448A1 (en) * | 2019-10-14 | 2021-04-22 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators for treating pituitary adenomas |
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| CA3191084A1 (en) | 2020-09-09 | 2022-03-17 | Gerald Burke | Formulations of a somatostatin modulator |
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| JP7365347B2 (ja) | 2018-02-12 | 2023-10-19 | クリネティックス ファーマシューティカルズ，インク． | ソマトスタチンモジュレーターおよびその使用 |
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2018
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- 2018-03-15 WO PCT/US2018/022665 patent/WO2018170284A1/en not_active Ceased
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- 2018-03-15 UA UAA201910112A patent/UA127346C2/uk unknown
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- 2018-03-15 SG SG11201908512Y patent/SG11201908512YA/en unknown
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2019
- 2019-09-16 US US16/572,453 patent/US11072598B2/en active Active