HRP20020732A2 - Substituted 3-phenyl-5-alkoxi-1,3,4-oxdiazol-2-one and use thereof for inhibiting hormone-sensitive lipase - Google Patents
Substituted 3-phenyl-5-alkoxi-1,3,4-oxdiazol-2-one and use thereof for inhibiting hormone-sensitive lipase Download PDFInfo
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- HRP20020732A2 HRP20020732A2 HRP20020732A HRP20020732A2 HR P20020732 A2 HRP20020732 A2 HR P20020732A2 HR P20020732 A HRP20020732 A HR P20020732A HR P20020732 A2 HRP20020732 A2 HR P20020732A2
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- Prior art keywords
- alkyl
- substituted
- aryl
- halogen
- alkyloxy
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- 102000000019 Sterol Esterase Human genes 0.000 title claims description 15
- 108010055297 Sterol Esterase Proteins 0.000 title claims description 15
- 230000002401 inhibitory effect Effects 0.000 title claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 60
- 150000002367 halogens Chemical group 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 49
- -1 C1-C4-alkyloxy Chemical group 0.000 claims description 35
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
- 238000007385 chemical modification Methods 0.000 claims description 2
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 102100026020 Hormone-sensitive lipase Human genes 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 150000004651 carbonic acid esters Chemical class 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 238000002844 melting Methods 0.000 description 89
- 230000008018 melting Effects 0.000 description 89
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
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- WVEMHEUXDRVXJO-UHFFFAOYSA-N 3-(4-amino-3-methylphenyl)-5-methoxy-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OC)=NN1C1=CC=C(N)C(C)=C1 WVEMHEUXDRVXJO-UHFFFAOYSA-N 0.000 description 6
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 210000001789 adipocyte Anatomy 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 4
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- GDBQQVLCIARPGH-UHFFFAOYSA-N Leupeptin Natural products CC(C)CC(NC(C)=O)C(=O)NC(CC(C)C)C(=O)NC(C=O)CCCN=C(N)N GDBQQVLCIARPGH-UHFFFAOYSA-N 0.000 description 4
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- 230000000694 effects Effects 0.000 description 4
- 229940088598 enzyme Drugs 0.000 description 4
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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- SDNYTAYICBFYFH-TUFLPTIASA-N antipain Chemical compound NC(N)=NCCC[C@@H](C=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 SDNYTAYICBFYFH-TUFLPTIASA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
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- RERPRXPTVXLOFR-UHFFFAOYSA-N (2-methyl-4-nitrophenyl)hydrazine Chemical compound CC1=CC([N+]([O-])=O)=CC=C1NN RERPRXPTVXLOFR-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
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- KHICPASJCVEVBY-UHFFFAOYSA-N 3-[3-[(4-fluorophenyl)methoxy]-4-nitrophenyl]-5-methoxy-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OC)=NN1C1=CC=C([N+]([O-])=O)C(OCC=2C=CC(F)=CC=2)=C1 KHICPASJCVEVBY-UHFFFAOYSA-N 0.000 description 2
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- GFJGXSFOJGLCGD-UHFFFAOYSA-N 4-chloro-n-[4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)-2-methylphenyl]butanamide Chemical compound O=C1OC(OC)=NN1C1=CC=C(NC(=O)CCCCl)C(C)=C1 GFJGXSFOJGLCGD-UHFFFAOYSA-N 0.000 description 2
- KFIXQXHBBYKXBJ-UHFFFAOYSA-N 5-methoxy-3-(4-nitrophenyl)-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OC)=NN1C1=CC=C([N+]([O-])=O)C=C1 KFIXQXHBBYKXBJ-UHFFFAOYSA-N 0.000 description 2
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- 238000011534 incubation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PBNRFAMNCFKUJO-UHFFFAOYSA-N n-[2-fluoro-4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)phenyl]-4-(trifluoromethyl)benzamide Chemical compound O=C1OC(OC)=NN1C(C=C1F)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 PBNRFAMNCFKUJO-UHFFFAOYSA-N 0.000 description 1
- FMWALFXDYBSANK-UHFFFAOYSA-N n-[3-chloro-4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)phenyl]-4-heptylbenzamide Chemical compound C1=CC(CCCCCCC)=CC=C1C(=O)NC1=CC=C(N2C(OC(OC)=N2)=O)C(Cl)=C1 FMWALFXDYBSANK-UHFFFAOYSA-N 0.000 description 1
- JLSLIAMUMMHLHV-UHFFFAOYSA-N n-[4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)-2-methylphenyl]-2-phenylethenesulfonamide Chemical compound O=C1OC(OC)=NN1C(C=C1C)=CC=C1NS(=O)(=O)C=CC1=CC=CC=C1 JLSLIAMUMMHLHV-UHFFFAOYSA-N 0.000 description 1
- KPMUKLJFNDTDSE-UHFFFAOYSA-N n-[4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)-2-methylphenyl]naphthalene-1-sulfonamide Chemical compound O=C1OC(OC)=NN1C(C=C1C)=CC=C1NS(=O)(=O)C1=CC=CC2=CC=CC=C12 KPMUKLJFNDTDSE-UHFFFAOYSA-N 0.000 description 1
- ANSXSXRHYSZEFR-UHFFFAOYSA-N n-[4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)-2-methylphenyl]piperidine-1-carboxamide Chemical compound O=C1OC(OC)=NN1C(C=C1C)=CC=C1NC(=O)N1CCCCC1 ANSXSXRHYSZEFR-UHFFFAOYSA-N 0.000 description 1
- OZKDLPCWKJNTAH-UHFFFAOYSA-N n-[4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)-2-methylphenyl]pyridine-3-carboxamide Chemical compound O=C1OC(OC)=NN1C(C=C1C)=CC=C1NC(=O)C1=CC=CN=C1 OZKDLPCWKJNTAH-UHFFFAOYSA-N 0.000 description 1
- KEZYVRNCEKIFCI-UHFFFAOYSA-N n-[4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)-2-phenylmethoxyphenyl]-4-(trifluoromethyl)benzamide Chemical compound O=C1OC(OC)=NN1C(C=C1OCC=2C=CC=CC=2)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 KEZYVRNCEKIFCI-UHFFFAOYSA-N 0.000 description 1
- GVODTCVMWJMRSF-UHFFFAOYSA-N n-[4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)-3-methylphenyl]-4-(trifluoromethoxy)benzamide Chemical compound O=C1OC(OC)=NN1C(C(=C1)C)=CC=C1NC(=O)C1=CC=C(OC(F)(F)F)C=C1 GVODTCVMWJMRSF-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- KMPKTVKLWXJAPO-UHFFFAOYSA-N phenyl n-[4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)-2-methylphenyl]carbamate Chemical compound O=C1OC(OC)=NN1C(C=C1C)=CC=C1NC(=O)OC1=CC=CC=C1 KMPKTVKLWXJAPO-UHFFFAOYSA-N 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000003905 phosphatidylinositols Chemical class 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- ADMYBPBXNPUKTP-UHFFFAOYSA-N pyridin-3-ylmethyl n-[4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)-2-methylphenyl]carbamate Chemical compound O=C1OC(OC)=NN1C(C=C1C)=CC=C1NC(=O)OCC1=CC=CN=C1 ADMYBPBXNPUKTP-UHFFFAOYSA-N 0.000 description 1
- 108700022737 rat Fat1 Proteins 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2000110968 DE10010968A1 (de) | 2000-03-07 | 2000-03-07 | Substituierte 3-Phenyl-5-alkoxi-1,3,4-oxdiazol-2-one, ihre Herstellung und Verwendung in Arzneistoffen |
| DE2001102265 DE10102265C1 (de) | 2001-01-18 | 2001-01-18 | Substituierte 3-Phenyl-5-alkoxi-1,3,4-oxdiazol-2-one, ihre Herstellung und Verwendung in Arzneistoffen |
| PCT/EP2001/001898 WO2001066531A1 (de) | 2000-03-07 | 2001-02-20 | Substituierte 3-phenyl-5-alkoxi-1,3,4-oxdiazol-2-one (und) ihre verwendung zur hemmung der hormonsensitiven lipase |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20020732A2 true HRP20020732A2 (en) | 2004-12-31 |
Family
ID=26004720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20020732 HRP20020732A2 (en) | 2000-03-07 | 2002-09-05 | Substituted 3-phenyl-5-alkoxi-1,3,4-oxdiazol-2-one and use thereof for inhibiting hormone-sensitive lipase |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US6369088B2 (ko) |
| EP (1) | EP1263745B1 (ko) |
| JP (1) | JP2003525931A (ko) |
| KR (1) | KR100790763B1 (ko) |
| CN (1) | CN1261419C (ko) |
| AR (1) | AR027611A1 (ko) |
| AT (1) | ATE267184T1 (ko) |
| AU (1) | AU784827B2 (ko) |
| BR (1) | BR0108974A (ko) |
| CA (1) | CA2401953A1 (ko) |
| DE (1) | DE50102325D1 (ko) |
| DK (1) | DK1263745T3 (ko) |
| EE (1) | EE04877B1 (ko) |
| ES (1) | ES2218383T3 (ko) |
| HK (1) | HK1054036B (ko) |
| HR (1) | HRP20020732A2 (ko) |
| HU (1) | HUP0302772A3 (ko) |
| IL (1) | IL151518A (ko) |
| MX (1) | MXPA02008038A (ko) |
| NO (1) | NO323483B1 (ko) |
| NZ (1) | NZ521207A (ko) |
| PL (1) | PL359702A1 (ko) |
| PT (1) | PT1263745E (ko) |
| RU (1) | RU2281283C2 (ko) |
| SK (1) | SK12752002A3 (ko) |
| TR (1) | TR200401217T4 (ko) |
| WO (1) | WO2001066531A1 (ko) |
| YU (1) | YU57802A (ko) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6087350A (en) * | 1997-08-29 | 2000-07-11 | University Of Pittsburgh Of The Commonwealth System Of Higher Education | Use of pretreatment chemicals to enhance efficacy of cytotoxic agents |
| DE10208986A1 (de) * | 2002-02-28 | 2003-09-11 | Aventis Pharma Gmbh | Verwendung substituierter 3-Phenyl-5-alkoxi-1,3,4-oxdiazol-2-one zur Herstellung von Arzneimitteln mit hemmender Wirkung an der pankreatischen Lipase |
| US6900233B2 (en) | 2002-02-28 | 2005-05-31 | Aventis Pharma Deutschland Gmbh | Substituted 3-phenyl-5-alkoxy-3H-(1,3,4)-oxadiazol-2-ones, pharmaceutical composition and method for treating obesity thereof |
| DE10208987A1 (de) * | 2002-02-28 | 2003-09-11 | Aventis Pharma Gmbh | Substituierte 3-Phenyl-5-alkoxi-1,3,4-oxidiazol-2-one, ihre Herstellung und Verwendung in Arzneistoffen |
| US20030236288A1 (en) * | 2002-02-28 | 2003-12-25 | Karl Schoenafinger | Use of substituted 3-phenyl-5-alkoxy-3H-(1,3,4)-oxadizol-2-ones for inhibiting pancreatic lipase |
| SE0203754D0 (sv) * | 2002-12-17 | 2002-12-17 | Astrazeneca Ab | New compounds |
| SE0203753D0 (sv) * | 2002-12-17 | 2002-12-17 | Astrazeneca Ab | New compounds |
| US20090082435A1 (en) * | 2005-04-28 | 2009-03-26 | The Regents Of The University Of California | Methods, Compositions, And Compounds For Modulation Of Monoacylglycerol Lipase, Pain, And Stress-Related Disorders |
| CN101225085B (zh) * | 2007-01-17 | 2011-09-21 | 天津天士力集团有限公司 | 苯基呋咱氮类一氧化氮供体型2-苯胺嘧啶衍生物、其制备方法、含有该化合物的组合物及其用途 |
| TW201033163A (en) * | 2008-10-20 | 2010-09-16 | Sumitomo Chemical Co | Method for manufacturing oxadiazolinone compound and intermediate thereof |
| WO2010074587A2 (en) | 2008-12-23 | 2010-07-01 | Bial - Portela & Ca., S.A. | 5-o-substituted 3-n-aryl-1,3,4-oxadiazolones for medical use |
| EP2543660A4 (en) * | 2010-03-04 | 2014-04-30 | Ajinomoto Kk | PROPHYLACTIC OR THERAPEUTIC ACTIVE AGAINST DIABETES OR ADIPOSITAS |
| US8501768B2 (en) * | 2011-05-17 | 2013-08-06 | Hoffmann-La Roche Inc. | Hexahydrocyclopentapyrrolone, hexahydropyrrolopyrrolone, octahydropyrrolopyridinone and octahydropyridinone compounds |
| US9278910B2 (en) | 2011-05-31 | 2016-03-08 | Receptos, Inc. | GLP-1 receptor stabilizers and modulators |
| JP6061949B2 (ja) | 2011-12-12 | 2017-01-18 | レセプトス エルエルシー | 糖尿病などの疾患の治療のためのｇｌｐ−１受容体モジュレーターとして作用する４つの環を含むカルボン酸誘導体 |
| EA030857B1 (ru) | 2013-06-11 | 2018-10-31 | Селджин Интернэшнл Ii Сарл | Новые модуляторы рецептора glp-1 |
| UA119247C2 (uk) | 2013-09-06 | 2019-05-27 | РОЙВЕНТ САЙЕНСИЗ ҐмбГ | Спіроциклічні сполуки як інгібітори триптофангідроксилази |
| WO2015089137A1 (en) | 2013-12-11 | 2015-06-18 | Karos Pharmaceuticals, Inc. | Acylguanidines as tryptophan hydroxylase inhibitors |
| SG11201700364PA (en) | 2014-07-25 | 2017-02-27 | Celgene Internat Ii Sarl | Novel glp-1 receptor modulators |
| EP3230276B1 (en) | 2014-12-10 | 2020-09-02 | Celgene International II Sarl | Glp-1 receptor modulators |
| WO2016109501A1 (en) | 2014-12-30 | 2016-07-07 | Karos Pharmaceuticals, Inc. | Amide compounds as tryptophan hydroxylase inhibitors |
| US9611201B2 (en) | 2015-03-05 | 2017-04-04 | Karos Pharmaceuticals, Inc. | Processes for preparing (R)-1-(5-chloro-[1,1′-biphenyl]-2-yl)-2,2,2-trifluoroethanol and 1-(5-chloro-[1,1′-biphenyl]-2-yl)-2,2,2-trifluoroethanone |
| CN108863774A (zh) * | 2018-06-09 | 2018-11-23 | 石家庄市绿丰化工有限公司 | 一种2,4-二氯苯乙酰氯合成的方法 |
| CA3119912A1 (en) | 2018-11-14 | 2020-05-22 | Altavant Sciences Gmbh | A crystalline spirocyclic compound inhibitor of tryptophan hydroxylase 1 (tph1) for treating diseases or disorders associated with peripheral serotonin |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2299028A1 (fr) | 1975-02-03 | 1976-08-27 | Rhone Poulenc Ind | Nouvea |
| US4076824A (en) | 1975-02-03 | 1978-02-28 | Rhone-Poulenc Industries | Anthelmintic oxadiazolinone derivatives |
| FR2299328A1 (fr) | 1975-02-03 | 1976-08-27 | Rhone Poulenc Ind | Derives de l'alcoyloxy-5 phenyl-3 oxyde azo |
| DK156439C (da) | 1980-09-15 | 1990-01-22 | Shell Int Research | 7-substituerede 2,3-dihydrobenzofuranderivater samt pesticidpraeparater indeholdende disse og en fremgangsmaade til bekaempelse af skadelige organismer |
| DE3267258D1 (en) | 1981-06-15 | 1985-12-12 | Shell Int Research | 7-substituted 2,3-dihydrobenzofurans, their preparation and their use as pesticides or as chemical intermediates |
| DE3931843A1 (de) | 1989-09-23 | 1991-04-04 | Bayer Ag | Substituierte 1,3,4-oxa(thia)diazolinone verfahren zu ihrer herstellung und ihre verwendung der bekaempfung von endoparasiten |
| US5236939A (en) | 1989-09-23 | 1993-08-17 | Bayer Aktiengesellschaft | Substituted 1,3,4-oxa(thia)diazolinones process for their preparation and their use of combating endoparasites |
| US5641796A (en) * | 1994-11-01 | 1997-06-24 | Eli Lilly And Company | Oral hypoglycemic agents |
-
2001
- 2001-02-20 EP EP01905805A patent/EP1263745B1/de not_active Expired - Lifetime
- 2001-02-20 KR KR1020027011634A patent/KR100790763B1/ko not_active IP Right Cessation
- 2001-02-20 IL IL151518A patent/IL151518A/en not_active IP Right Cessation
- 2001-02-20 JP JP2001565347A patent/JP2003525931A/ja not_active Abandoned
- 2001-02-20 EE EEP200200498A patent/EE04877B1/xx not_active IP Right Cessation
- 2001-02-20 TR TR2004/01217T patent/TR200401217T4/xx unknown
- 2001-02-20 WO PCT/EP2001/001898 patent/WO2001066531A1/de active IP Right Grant
- 2001-02-20 CA CA002401953A patent/CA2401953A1/en not_active Abandoned
- 2001-02-20 NZ NZ521207A patent/NZ521207A/en unknown
- 2001-02-20 AU AU33787/01A patent/AU784827B2/en not_active Ceased
- 2001-02-20 ES ES01905805T patent/ES2218383T3/es not_active Expired - Lifetime
- 2001-02-20 BR BR0108974-9A patent/BR0108974A/pt not_active IP Right Cessation
- 2001-02-20 RU RU2002126556/04A patent/RU2281283C2/ru not_active IP Right Cessation
- 2001-02-20 YU YU57802A patent/YU57802A/sh unknown
- 2001-02-20 MX MXPA02008038A patent/MXPA02008038A/es active IP Right Grant
- 2001-02-20 PT PT01905805T patent/PT1263745E/pt unknown
- 2001-02-20 DK DK01905805T patent/DK1263745T3/da active
- 2001-02-20 HU HU0302772A patent/HUP0302772A3/hu unknown
- 2001-02-20 SK SK1275-2002A patent/SK12752002A3/sk unknown
- 2001-02-20 PL PL35970201A patent/PL359702A1/xx not_active IP Right Cessation
- 2001-02-20 DE DE50102325T patent/DE50102325D1/de not_active Expired - Lifetime
- 2001-02-20 AT AT01905805T patent/ATE267184T1/de not_active IP Right Cessation
- 2001-02-20 CN CNB018062156A patent/CN1261419C/zh not_active Expired - Fee Related
- 2001-03-05 AR ARP010101037A patent/AR027611A1/es not_active Application Discontinuation
- 2001-03-06 US US09/799,082 patent/US6369088B2/en not_active Expired - Lifetime
-
2002
- 2002-09-03 NO NO20024201A patent/NO323483B1/no unknown
- 2002-09-05 HR HRP20020732 patent/HRP20020732A2/hr not_active Application Discontinuation
-
2003
- 2003-09-09 HK HK03106394.6A patent/HK1054036B/zh not_active IP Right Cessation
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