JP6450755B2 - 複素環化合物 - Google Patents
複素環化合物 Download PDFInfo
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- JP6450755B2 JP6450755B2 JP2016526960A JP2016526960A JP6450755B2 JP 6450755 B2 JP6450755 B2 JP 6450755B2 JP 2016526960 A JP2016526960 A JP 2016526960A JP 2016526960 A JP2016526960 A JP 2016526960A JP 6450755 B2 JP6450755 B2 JP 6450755B2
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- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 296
- 125000001424 substituent group Chemical group 0.000 claims description 68
- 150000003839 salts Chemical class 0.000 claims description 59
- 239000003814 drug Substances 0.000 claims description 55
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 54
- 125000005843 halogen group Chemical group 0.000 claims description 53
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 34
- 206010012601 diabetes mellitus Diseases 0.000 claims description 33
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 29
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 27
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- 229940124597 therapeutic agent Drugs 0.000 claims description 15
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 10
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000005049 dihydrooxadiazolyl group Chemical group O1N(NC=C1)* 0.000 claims description 9
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 8
- YCNNISBIWQSGSY-UHFFFAOYSA-N 1-[1-[[5-cyclopropyl-3-fluoro-4-(4-fluorophenyl)-2-propan-2-yloxyphenyl]methyl]piperidin-4-yl]-3-methyl-2-oxopyridine-4-carboxylic acid Chemical compound C1=C(C2CC2)C(C=2C=CC(F)=CC=2)=C(F)C(OC(C)C)=C1CN(CC1)CCC1N1C=CC(C(O)=O)=C(C)C1=O YCNNISBIWQSGSY-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000003449 preventive effect Effects 0.000 claims description 4
- 230000000069 prophylactic effect Effects 0.000 claims description 4
- LPEMKFJSNNTTOS-UHFFFAOYSA-N 1-[1-[[5-cyclopropyl-3-fluoro-4-(4-fluorophenyl)-2-propan-2-yloxyphenyl]methyl]piperidin-4-yl]-3-ethyl-2-oxopyridine-4-carboxylic acid Chemical compound CCc1c(ccn(C2CCN(Cc3cc(C4CC4)c(c(F)c3OC(C)C)-c3ccc(F)cc3)CC2)c1=O)C(O)=O LPEMKFJSNNTTOS-UHFFFAOYSA-N 0.000 claims description 3
- ZKTIADLVQMCKGN-UHFFFAOYSA-N 1-[1-[[5-cyclopropyl-4-(4-fluorophenyl)-2-propan-2-yloxyphenyl]methyl]piperidin-4-yl]-2-oxopyridine-4-carboxylic acid Chemical compound CC(C)Oc1cc(-c2ccc(F)cc2)c(cc1CN1CCC(CC1)n1ccc(cc1=O)C(O)=O)C1CC1 ZKTIADLVQMCKGN-UHFFFAOYSA-N 0.000 claims description 3
- 229940123829 Somatostatin receptor 5 antagonist Drugs 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 528
- -1 1,1-dimethylbutyl Chemical group 0.000 description 327
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 285
- 239000000203 mixture Substances 0.000 description 218
- 239000002904 solvent Substances 0.000 description 124
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 120
- 230000002829 reductive effect Effects 0.000 description 116
- 239000000243 solution Substances 0.000 description 110
- 239000011541 reaction mixture Substances 0.000 description 101
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 91
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 83
- 239000012044 organic layer Substances 0.000 description 82
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 81
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 80
- 238000010898 silica gel chromatography Methods 0.000 description 76
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 72
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 64
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 61
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 61
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 59
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- 239000012299 nitrogen atmosphere Substances 0.000 description 57
- 235000002639 sodium chloride Nutrition 0.000 description 56
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 50
- 239000002585 base Substances 0.000 description 42
- 238000000034 method Methods 0.000 description 42
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 39
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 38
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 38
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 34
- 239000003153 chemical reaction reagent Substances 0.000 description 32
- 229940079593 drug Drugs 0.000 description 32
- 238000001819 mass spectrum Methods 0.000 description 32
- 238000000132 electrospray ionisation Methods 0.000 description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 238000001914 filtration Methods 0.000 description 30
- 125000000623 heterocyclic group Chemical group 0.000 description 30
- 238000002360 preparation method Methods 0.000 description 28
- 239000000706 filtrate Substances 0.000 description 27
- 125000006239 protecting group Chemical group 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- 229920006395 saturated elastomer Polymers 0.000 description 25
- 229910000029 sodium carbonate Inorganic materials 0.000 description 25
- 238000003756 stirring Methods 0.000 description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- 239000008103 glucose Substances 0.000 description 21
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 20
- 208000008589 Obesity Diseases 0.000 description 20
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 20
- 235000020824 obesity Nutrition 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- 125000003277 amino group Chemical group 0.000 description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 19
- 239000003112 inhibitor Substances 0.000 description 19
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 19
- 229910000027 potassium carbonate Inorganic materials 0.000 description 19
- 235000017557 sodium bicarbonate Nutrition 0.000 description 19
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 19
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 19
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 18
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 18
- 229910052731 fluorine Inorganic materials 0.000 description 18
- 239000011737 fluorine Substances 0.000 description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 18
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 17
- 235000019253 formic acid Nutrition 0.000 description 17
- 150000001721 carbon Chemical group 0.000 description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 15
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 13
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 12
- 239000012300 argon atmosphere Substances 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 12
- WLVKDFJTYKELLQ-UHFFFAOYSA-N cyclopropylboronic acid Chemical compound OB(O)C1CC1 WLVKDFJTYKELLQ-UHFFFAOYSA-N 0.000 description 12
- 201000010099 disease Diseases 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 11
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 11
- 208000001145 Metabolic Syndrome Diseases 0.000 description 11
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
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- 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
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- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 10
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- 125000003710 aryl alkyl group Chemical group 0.000 description 10
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- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 8
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- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 7
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- 238000005886 esterification reaction Methods 0.000 description 7
- HUSQCRBMHJMLPS-UHFFFAOYSA-N methyl 3-ethyl-1-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]-2-oxopyridine-4-carboxylate Chemical compound CCc1c(ccn(C2CCN(CC2)C(=O)OC(C)(C)C)c1=O)C(=O)OC HUSQCRBMHJMLPS-UHFFFAOYSA-N 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 6
- 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 6
- 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
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- 241000124008 Mammalia Species 0.000 description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013224093 | 2013-10-29 | ||
| JP2013224093 | 2013-10-29 | ||
| PCT/JP2014/005438 WO2015064083A1 (en) | 2013-10-29 | 2014-10-28 | Heterocyclic compound |
Publications (3)
| Publication Number | Publication Date |
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| JP2016535040A JP2016535040A (ja) | 2016-11-10 |
| JP2016535040A5 JP2016535040A5 (enExample) | 2017-11-09 |
| JP6450755B2 true JP6450755B2 (ja) | 2019-01-09 |
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| JP2016526960A Active JP6450755B2 (ja) | 2013-10-29 | 2014-10-28 | 複素環化合物 |
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| WO2013122029A1 (ja) * | 2012-02-13 | 2013-08-22 | 武田薬品工業株式会社 | 芳香環化合物 |
| US9605000B2 (en) | 2013-03-14 | 2017-03-28 | Takeda Pharmaceutical Company Limited | Spiro azetidine isoxazole derivatives and their use as SSTR antagonists |
| JO3442B1 (ar) | 2013-10-07 | 2019-10-20 | Takeda Pharmaceuticals Co | مضادات ذات نوع فرعي من مستقبل سوماتوستاتين 5 (sstr5) |
| US20230049619A1 (en) * | 2019-12-19 | 2023-02-16 | Universite De Strasbourg | Sigma-1 receptor ligands and uses thereof |
| WO2022052958A1 (en) | 2020-09-10 | 2022-03-17 | Gasherbrum Bio, Inc. | Heterocyclic glp-1 agonists |
| CN116354961B (zh) * | 2021-12-27 | 2025-07-25 | 中国科学院上海药物研究所 | 生长抑素受体5拮抗剂及其药物组合物及用途 |
| WO2024204277A1 (ja) | 2023-03-27 | 2024-10-03 | 株式会社スコヒアファーマ | 成長ホルモン分泌促進剤 |
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| US5356906A (en) | 1989-10-27 | 1994-10-18 | The Du Pont Merck Pharmaceutical Company | (N-phthalimidoalkyl) piperidines useful as treatments for psychosis |
| WO2001096308A1 (en) | 2000-06-12 | 2001-12-20 | Eisai Co., Ltd. | 1,2-dihydropyridine compounds, process for preparation of the same and use thereof |
| GB0129260D0 (en) | 2001-12-06 | 2002-01-23 | Eisai London Res Lab Ltd | Pharmaceutical compositions and their uses |
| JP4736043B2 (ja) | 2003-03-14 | 2011-07-27 | 小野薬品工業株式会社 | 含窒素複素環誘導体およびそれらを有効成分とする薬剤 |
| CN1902171A (zh) | 2003-11-10 | 2007-01-24 | 舍林股份公司 | 用作ccr－5拮抗剂的苄醚胺化合物 |
| KR101117931B1 (ko) * | 2006-08-15 | 2012-04-12 | 에프. 호프만-라 로슈 아게 | 페닐, 피리딘 및 퀴놀린 유도체 |
| US7862825B2 (en) | 2007-02-21 | 2011-01-04 | Mladen Vranic | Method of controlling tight blood glucose by somatostatin receptor antagonists |
| US7799806B2 (en) | 2007-04-04 | 2010-09-21 | Hoffmann-La Roche Inc. | Substituted n-benzyl piperidines as somatostatin receptor modulators |
| US20080306116A1 (en) | 2007-06-08 | 2008-12-11 | Christ Andreas D | Aryloxazole, aryloxadiazole and benzimidazole derivatives |
| TW200918062A (en) | 2007-09-12 | 2009-05-01 | Wyeth Corp | Azacyclylisoquinolinone and-isoindolinone derivatives as histamine-3 antagonists |
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| US8742110B2 (en) | 2010-08-18 | 2014-06-03 | Merck Sharp & Dohme Corp. | Spiroxazolidinone compounds |
| US9000175B2 (en) | 2010-11-26 | 2015-04-07 | Lupin Limited | Bicyclic GPR119 modulators |
| US9605000B2 (en) | 2013-03-14 | 2017-03-28 | Takeda Pharmaceutical Company Limited | Spiro azetidine isoxazole derivatives and their use as SSTR antagonists |
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| LT3063139T (lt) | 2019-02-25 |
| CY1121279T1 (el) | 2020-05-29 |
| EP3063139A1 (en) | 2016-09-07 |
| WO2015064083A1 (en) | 2015-05-07 |
| PL3063139T3 (pl) | 2019-05-31 |
| AR128158A2 (es) | 2024-03-27 |
| UY35801A (es) | 2015-06-30 |
| US20150119412A1 (en) | 2015-04-30 |
| EP3063139B1 (en) | 2018-11-21 |
| JP2016535040A (ja) | 2016-11-10 |
| PT3063139T (pt) | 2019-02-22 |
| ES2710657T3 (es) | 2019-04-26 |
| TR201901986T4 (tr) | 2019-03-21 |
| HUE041792T2 (hu) | 2019-05-28 |
| TW201542539A (zh) | 2015-11-16 |
| TWI668214B (zh) | 2019-08-11 |
| DK3063139T3 (en) | 2019-03-11 |
| SI3063139T1 (sl) | 2019-03-29 |
| US9120777B2 (en) | 2015-09-01 |
| RS58321B1 (sr) | 2019-03-29 |
| SMT201900101T1 (it) | 2019-02-28 |
| AR098215A1 (es) | 2016-05-18 |
| HRP20190133T1 (hr) | 2019-03-22 |
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