CN118420620A - 杂环化合物 - Google Patents
杂环化合物 Download PDFInfo
- Publication number
- CN118420620A CN118420620A CN202410510968.2A CN202410510968A CN118420620A CN 118420620 A CN118420620 A CN 118420620A CN 202410510968 A CN202410510968 A CN 202410510968A CN 118420620 A CN118420620 A CN 118420620A
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- alkyl
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- 150000002391 heterocyclic compounds Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 340
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 201000011510 cancer Diseases 0.000 claims abstract description 19
- 239000013078 crystal Substances 0.000 claims abstract description 19
- 230000003449 preventive effect Effects 0.000 claims abstract description 9
- 229940126585 therapeutic drug Drugs 0.000 claims abstract description 9
- 239000012453 solvate Substances 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims description 160
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 79
- 125000001424 substituent group Chemical group 0.000 claims description 75
- -1 Imidazolopyridinyl Chemical group 0.000 claims description 74
- 239000003814 drug Substances 0.000 claims description 68
- 229940079593 drug Drugs 0.000 claims description 61
- 125000003545 alkoxy group Chemical group 0.000 claims description 50
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000001425 triazolyl group Chemical group 0.000 claims description 18
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- YASXOENRCPGYQB-VIFPVBQESA-N 1-[5-chloro-6-(difluoromethoxy)pyridin-3-yl]-3-[8-[(1S)-1-methoxyethyl]-2-methylimidazo[1,2-b]pyridazin-7-yl]urea Chemical compound ClC=1C=C(C=NC1OC(F)F)NC(=O)NC1=C(C=2N(N=C1)C=C(N2)C)[C@H](C)OC YASXOENRCPGYQB-VIFPVBQESA-N 0.000 claims description 8
- MKYDKGUTYKFCHS-JTQLQIEISA-N 1-[6-chloro-4-[(1S)-1-methoxyethyl]-1,5-naphthyridin-3-yl]-3-[6-(triazol-2-yl)-5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound ClC=1N=C2C(=C(C=NC2=CC1)NC(=O)NC=1C=NC(=C(C1)C(F)(F)F)N1N=CC=N1)[C@H](C)OC MKYDKGUTYKFCHS-JTQLQIEISA-N 0.000 claims description 8
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- XIZGLLSADFNPPE-LBPRGKRZSA-N 1-[4-[(1S)-1-methoxyethyl]-6-methyl-1,5-naphthyridin-3-yl]-3-[6-(triazol-2-yl)-5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound CO[C@@H](C)C1=C(C=NC2=CC=C(N=C12)C)NC(=O)NC=1C=NC(=C(C1)C(F)(F)F)N1N=CC=N1 XIZGLLSADFNPPE-LBPRGKRZSA-N 0.000 claims description 5
- DPSKUJVVNPRGCG-UHFFFAOYSA-N 1-[5-chloro-6-(difluoromethoxy)pyridin-3-yl]-3-(2-chloro-8-propan-2-ylimidazo[1,2-b]pyridazin-7-yl)urea Chemical compound ClC=1C=C(C=NC1OC(F)F)NC(=O)NC1=C(C=2N(N=C1)C=C(N2)Cl)C(C)C DPSKUJVVNPRGCG-UHFFFAOYSA-N 0.000 claims description 5
- QDTOTZUBNNQTIG-UHFFFAOYSA-N 1-[5-chloro-6-(triazol-2-yl)pyridin-3-yl]-3-(2-methyl-8-propan-2-ylimidazo[1,2-b]pyridazin-7-yl)urea Chemical compound ClC=1C=C(C=NC1N1N=CC=N1)NC(=O)NC1=C(C=2N(N=C1)C=C(N2)C)C(C)C QDTOTZUBNNQTIG-UHFFFAOYSA-N 0.000 claims description 5
- JWALSWVUILVGEM-UHFFFAOYSA-N 1-[5-chloro-6-(triazol-2-yl)pyridin-3-yl]-3-[8-(2-methoxypropan-2-yl)-2-methylimidazo[1,2-b]pyridazin-7-yl]urea Chemical compound ClC=1C=C(C=NC1N1N=CC=N1)NC(=O)NC1=C(C=2N(N=C1)C=C(N2)C)C(C)(C)OC JWALSWVUILVGEM-UHFFFAOYSA-N 0.000 claims description 5
- VDXYKDPULPAMFX-NSHDSACASA-N 1-[8-[(1S)-1-methoxyethyl]-2-methylimidazo[1,2-b]pyridazin-7-yl]-3-[6-(triazol-2-yl)-5-(trifluoromethyl)pyridin-3-yl]urea Chemical compound CO[C@@H](C)C=1C=2N(N=CC1NC(=O)NC=1C=NC(=C(C1)C(F)(F)F)N1N=CC=N1)C=C(N2)C VDXYKDPULPAMFX-NSHDSACASA-N 0.000 claims description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 125000002393 azetidinyl group Chemical group 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- ZRTRVWVBBGGJKA-NSHDSACASA-N 1-[5-chloro-6-(triazol-2-yl)pyridin-3-yl]-3-[8-[(1S)-1-methoxyethyl]-2-methylimidazo[1,2-b]pyridazin-7-yl]urea Chemical compound ClC=1C=C(C=NC1N1N=CC=N1)NC(=O)NC1=C(C=2N(N=C1)C=C(N2)C)[C@H](C)OC ZRTRVWVBBGGJKA-NSHDSACASA-N 0.000 claims description 4
- AGXMSTXRPJQSNW-JTQLQIEISA-N 1-[5-cyano-6-(difluoromethoxy)pyridin-3-yl]-3-[8-[(1S)-1-methoxyethyl]-2-methylimidazo[1,2-b]pyridazin-7-yl]urea Chemical compound C(#N)C=1C=C(C=NC1OC(F)F)NC(=O)NC1=C(C=2N(N=C1)C=C(N2)C)[C@H](C)OC AGXMSTXRPJQSNW-JTQLQIEISA-N 0.000 claims description 4
- TWJGQZBSEMDPQP-UHFFFAOYSA-N 2-chloro-n-[4-[5-(3,4-dichlorophenyl)-3-(2-methoxyethoxy)-1,2,4-triazol-1-yl]phenyl]acetamide Chemical compound C=1C=C(NC(=O)CCl)C=CC=1N1N=C(OCCOC)N=C1C1=CC=C(Cl)C(Cl)=C1 TWJGQZBSEMDPQP-UHFFFAOYSA-N 0.000 claims description 2
- 229940122339 MALT1 inhibitor Drugs 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 22
- 230000002401 inhibitory effect Effects 0.000 abstract description 16
- 102000057613 Mucosa-Associated Lymphoid Tissue Lymphoma Translocation 1 Human genes 0.000 abstract description 2
- 108700026676 Mucosa-Associated Lymphoid Tissue Lymphoma Translocation 1 Proteins 0.000 abstract description 2
- 101150113681 MALT1 gene Proteins 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 321
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 165
- 239000011541 reaction mixture Substances 0.000 description 91
- 239000000243 solution Substances 0.000 description 91
- 230000002829 reductive effect Effects 0.000 description 81
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
- 238000000034 method Methods 0.000 description 64
- 239000000203 mixture Substances 0.000 description 63
- 125000001153 fluoro group Chemical group F* 0.000 description 60
- 239000003112 inhibitor Substances 0.000 description 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 56
- 239000002904 solvent Substances 0.000 description 48
- 125000001309 chloro group Chemical group Cl* 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 46
- 238000010898 silica gel chromatography Methods 0.000 description 45
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 43
- 229910052731 fluorine Inorganic materials 0.000 description 43
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- 239000012044 organic layer Substances 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 35
- 239000002585 base Substances 0.000 description 35
- 238000006243 chemical reaction Methods 0.000 description 35
- 125000006239 protecting group Chemical group 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 229910052801 chlorine Inorganic materials 0.000 description 32
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 31
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 30
- 239000003153 chemical reaction reagent Substances 0.000 description 29
- 238000002360 preparation method Methods 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 26
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000005481 NMR spectroscopy Methods 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 20
- 125000000217 alkyl group Chemical group 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 19
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
- 239000002253 acid Substances 0.000 description 17
- 239000000126 substance Substances 0.000 description 17
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 16
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 16
- 239000010410 layer Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 239000012190 activator Substances 0.000 description 12
- 230000010261 cell growth Effects 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 12
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 11
- RWISYPZSGXHJNJ-UHFFFAOYSA-N 6-(triazol-2-yl)-5-(trifluoromethyl)pyridin-3-amine Chemical compound NC1=CC(=C(N=C1)N1N=CC=N1)C(F)(F)F RWISYPZSGXHJNJ-UHFFFAOYSA-N 0.000 description 11
- 102000018233 Fibroblast Growth Factor Human genes 0.000 description 11
- 108050007372 Fibroblast Growth Factor Proteins 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 11
- 229940126864 fibroblast growth factor Drugs 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 125000003277 amino group Chemical group 0.000 description 10
- 238000005859 coupling reaction Methods 0.000 description 10
- 238000005755 formation reaction Methods 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- 101000957807 Homo sapiens Mucosa-associated lymphoid tissue lymphoma translocation protein 1 Proteins 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 238000006969 Curtius rearrangement reaction Methods 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
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- 102000052696 human MALT1 Human genes 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
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- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical group COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 8
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- 230000002378 acidificating effect Effects 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
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- 238000010534 nucleophilic substitution reaction Methods 0.000 description 7
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- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- 150000001350 alkyl halides Chemical class 0.000 description 6
- PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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- 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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
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- A—HUMAN NECESSITIES
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- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
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- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- 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
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- C—CHEMISTRY; METALLURGY
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
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- Biophysics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicinal Preparation (AREA)
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| JP2018-222530 | 2018-11-28 | ||
| JP2018222530 | 2018-11-28 | ||
| CN201980078144.XA CN113038948B (zh) | 2018-11-28 | 2019-11-27 | 杂环化合物 |
| PCT/JP2019/046261 WO2020111087A1 (ja) | 2018-11-28 | 2019-11-27 | 複素環化合物 |
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| CN201980078144.XA Division CN113038948B (zh) | 2018-11-28 | 2019-11-27 | 杂环化合物 |
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| IL283368B2 (en) * | 2018-11-28 | 2025-01-01 | Takeda Pharmaceuticals Co | Imidazo[2,1-b]pyridazin-7-yl urea compound and medicament containing the compound |
| JP7672402B2 (ja) * | 2020-05-27 | 2025-05-07 | 武田薬品工業株式会社 | 複素環化合物の製造方法 |
| AU2021361057A1 (en) * | 2020-10-16 | 2023-06-08 | Rarefied Biosciences, Inc. | Malt1 modulators and uses thereof |
| GB202018412D0 (en) | 2020-11-23 | 2021-01-06 | Exscientia Ltd | Malt-1 modulators ii |
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| WO2025123039A1 (en) * | 2023-12-08 | 2025-06-12 | Shaman Pharma, LLC | Method for Production of Spiro-Oxindole and Indoxyl Derivatives of Mitragynine |
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| FR2288521A1 (fr) | 1974-10-25 | 1976-05-21 | Merck Patent Gmbh | Nouvelles penicillines et procede pour leur preparation |
| WO1996038445A1 (en) * | 1995-05-31 | 1996-12-05 | Sumitomo Pharmaceuticals Company, Limited | Novel naphthyridine derivatives |
| GB9720052D0 (en) * | 1997-09-19 | 1997-11-19 | Smithkline Beecham Plc | Novel compounds |
| GB201321734D0 (en) * | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic Agents |
| RS59039B1 (sr) * | 2014-05-28 | 2019-08-30 | Novartis Ag | Novi derivati pirazolo pirimidina i njihova primena kao inhibitora malt1 |
| SG11201803480WA (en) * | 2015-11-13 | 2018-05-30 | Novartis Ag | Novel pyrazolo pyrimidine derivatives |
| PE20190656A1 (es) | 2016-07-29 | 2019-05-08 | Lupin Ltd | Compuestos de tiazolo-piridina sustituida como inhibidores de malt1 |
| WO2018085247A1 (en) * | 2016-11-01 | 2018-05-11 | Cornell University | Compounds for malt1 degradation |
| JP7142022B2 (ja) * | 2017-03-08 | 2022-09-26 | コーネル・ユニバーシティー | Ｍａｌｔ１の阻害剤およびそれらの使用 |
| US20200111087A1 (en) * | 2018-10-08 | 2020-04-09 | Jinlei Zhou | Method for encrypting digital contract document between contractors |
| IL283368B2 (en) * | 2018-11-28 | 2025-01-01 | Takeda Pharmaceuticals Co | Imidazo[2,1-b]pyridazin-7-yl urea compound and medicament containing the compound |
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