NO323483B1 - Substituerte 3-fenyl-5-alkoksy-1,3,4-oksdiazol-2-on og anvendelse derav for hemning av hormonsensitiv lipase samt fremgangsmate for fremstilling av forbindelsene. - Google Patents
Substituerte 3-fenyl-5-alkoksy-1,3,4-oksdiazol-2-on og anvendelse derav for hemning av hormonsensitiv lipase samt fremgangsmate for fremstilling av forbindelsene. Download PDFInfo
- Publication number
- NO323483B1 NO323483B1 NO20024201A NO20024201A NO323483B1 NO 323483 B1 NO323483 B1 NO 323483B1 NO 20024201 A NO20024201 A NO 20024201A NO 20024201 A NO20024201 A NO 20024201A NO 323483 B1 NO323483 B1 NO 323483B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- substituted
- aryl
- halogen
- alkyloxy
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 55
- 238000000034 method Methods 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 102000000019 Sterol Esterase Human genes 0.000 title claims abstract description 7
- 108010055297 Sterol Esterase Proteins 0.000 title claims abstract description 7
- 230000002401 inhibitory effect Effects 0.000 title claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 59
- 150000002367 halogens Chemical class 0.000 claims abstract description 59
- -1 2-oxopyrrolidin-1-yl Chemical group 0.000 claims abstract description 38
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
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- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 15
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- 102100026020 Hormone-sensitive lipase Human genes 0.000 claims abstract description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 5
- 239000004305 biphenyl Substances 0.000 claims abstract description 4
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- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
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- 208000011580 syndromic disease Diseases 0.000 claims description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
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- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 3
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- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
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- 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
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- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 1
- 125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 claims 1
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- 125000004104 aryloxy group Chemical group 0.000 abstract 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- 238000002844 melting Methods 0.000 description 21
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- 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 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- JHFOWEGCZWLHNW-UHFFFAOYSA-N 4-fluoro-2-methyl-1-nitrobenzene Chemical compound CC1=CC(F)=CC=C1[N+]([O-])=O JHFOWEGCZWLHNW-UHFFFAOYSA-N 0.000 description 1
- LLIOADBCFIXIEU-UHFFFAOYSA-N 4-fluoro-3-nitroaniline Chemical compound NC1=CC=C(F)C([N+]([O-])=O)=C1 LLIOADBCFIXIEU-UHFFFAOYSA-N 0.000 description 1
- UUTYLSKGIIEBRI-UHFFFAOYSA-N 5-phenoxy-3h-1,3,4-oxadiazol-2-one Chemical class O1C(=O)NN=C1OC1=CC=CC=C1 UUTYLSKGIIEBRI-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 102000029816 Collagenase Human genes 0.000 description 1
- 108060005980 Collagenase Proteins 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920002684 Sepharose Polymers 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- YJKPEQVLHCYYRF-UHFFFAOYSA-N [3-[(4-fluorophenyl)methoxy]-4-nitrophenyl]hydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C(OCC=2C=CC(F)=CC=2)=C1 YJKPEQVLHCYYRF-UHFFFAOYSA-N 0.000 description 1
- GFTVEAPFCLTYQF-UHFFFAOYSA-N [4-(4-chlorophenoxy)-3-nitrophenyl]hydrazine Chemical compound [O-][N+](=O)C1=CC(NN)=CC=C1OC1=CC=C(Cl)C=C1 GFTVEAPFCLTYQF-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000003281 allosteric effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- MTMNJFGEKOYMIV-UHFFFAOYSA-N carbonyl dichloride;toluene Chemical compound ClC(Cl)=O.CC1=CC=CC=C1 MTMNJFGEKOYMIV-UHFFFAOYSA-N 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229960002424 collagenase Drugs 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 201000010063 epididymitis Diseases 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000005188 flotation Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 230000002608 insulinlike Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- GZBLKGSLVLNAHG-UHFFFAOYSA-N methyl n-(2-methyl-4-nitroanilino)carbamate Chemical compound COC(=O)NNC1=CC=C([N+]([O-])=O)C=C1C GZBLKGSLVLNAHG-UHFFFAOYSA-N 0.000 description 1
- ORTZJAMOEHDUOA-UHFFFAOYSA-N methyl n-(3-fluoro-4-nitroanilino)carbamate Chemical compound COC(=O)NNC1=CC=C([N+]([O-])=O)C(F)=C1 ORTZJAMOEHDUOA-UHFFFAOYSA-N 0.000 description 1
- UGHNJDHIASTMSR-UHFFFAOYSA-N methyl n-(4-nitro-3-piperidin-1-ylanilino)carbamate Chemical compound COC(=O)NNC1=CC=C([N+]([O-])=O)C(N2CCCCC2)=C1 UGHNJDHIASTMSR-UHFFFAOYSA-N 0.000 description 1
- SCEGCLQQOMZTSX-UHFFFAOYSA-N methyl n-(4-nitroanilino)carbamate Chemical compound COC(=O)NNC1=CC=C([N+]([O-])=O)C=C1 SCEGCLQQOMZTSX-UHFFFAOYSA-N 0.000 description 1
- JWFMBRJKHHCHQU-UHFFFAOYSA-N methyl n-[3-[(4-fluorophenyl)methoxy]-2-nitroanilino]carbamate Chemical compound COC(=O)NNC1=CC=CC(OCC=2C=CC(F)=CC=2)=C1[N+]([O-])=O JWFMBRJKHHCHQU-UHFFFAOYSA-N 0.000 description 1
- YZNUZVKODDCZTI-UHFFFAOYSA-N methyl n-[4-(4-chlorophenoxy)-3-nitroanilino]carbamate Chemical compound [O-][N+](=O)C1=CC(NNC(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1 YZNUZVKODDCZTI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000008188 pellet Substances 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
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 108700022737 rat Fat1 Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005932 reductive alkylation reaction 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
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 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
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000010792 warming 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Enzymes And Modification Thereof (AREA)
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 (3)
| Publication Number | Publication Date |
|---|---|
| NO20024201L NO20024201L (no) | 2002-09-03 |
| NO20024201D0 NO20024201D0 (no) | 2002-09-03 |
| NO323483B1 true NO323483B1 (no) | 2007-05-21 |
Family
ID=26004720
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20024201A NO323483B1 (no) | 2000-03-07 | 2002-09-03 | Substituerte 3-fenyl-5-alkoksy-1,3,4-oksdiazol-2-on og anvendelse derav for hemning av hormonsensitiv lipase samt fremgangsmate for fremstilling av forbindelsene. |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US6369088B2 (hu) |
| EP (1) | EP1263745B1 (hu) |
| JP (1) | JP2003525931A (hu) |
| KR (1) | KR100790763B1 (hu) |
| CN (1) | CN1261419C (hu) |
| AR (1) | AR027611A1 (hu) |
| AT (1) | ATE267184T1 (hu) |
| AU (1) | AU784827B2 (hu) |
| BR (1) | BR0108974A (hu) |
| CA (1) | CA2401953A1 (hu) |
| DE (1) | DE50102325D1 (hu) |
| DK (1) | DK1263745T3 (hu) |
| EE (1) | EE04877B1 (hu) |
| ES (1) | ES2218383T3 (hu) |
| HK (1) | HK1054036B (hu) |
| HR (1) | HRP20020732A2 (hu) |
| HU (1) | HUP0302772A3 (hu) |
| IL (1) | IL151518A (hu) |
| MX (1) | MXPA02008038A (hu) |
| NO (1) | NO323483B1 (hu) |
| NZ (1) | NZ521207A (hu) |
| PL (1) | PL359702A1 (hu) |
| PT (1) | PT1263745E (hu) |
| RU (1) | RU2281283C2 (hu) |
| SK (1) | SK12752002A3 (hu) |
| TR (1) | TR200401217T4 (hu) |
| WO (1) | WO2001066531A1 (hu) |
| YU (1) | YU57802A (hu) |
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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| TW201028406A (en) | 2008-12-23 | 2010-08-01 | Bial Portela & Ca Sa | 5-O-substituted 3-N-aryl-1,3,4-oxadiazolones for medical use |
| WO2011108724A1 (ja) | 2010-03-04 | 2011-09-09 | 味の素株式会社 | 糖尿病又は肥満症の予防又は治療剤 |
| 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 |
| US8778923B2 (en) | 2011-12-12 | 2014-07-15 | Receptos, Inc. | GLP-1 receptor modulators |
| EP3008056B8 (en) | 2013-06-11 | 2021-03-03 | Receptos Llc | Novel glp-1 receptor modulators |
| 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 |
| CN107074820B (zh) | 2014-07-25 | 2021-05-18 | 赛尔基因第二国际有限公司 | Glp-1受体调节剂 |
| AU2015360364B2 (en) | 2014-12-10 | 2020-04-30 | Receptos Llc | 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 |
| KR20210102887A (ko) | 2018-11-14 | 2021-08-20 | 알타반트 사이언시스 게엠베하 | 말초 세로토닌과 관련된 질병 또는 장애를 치료하기 위한 트립토판 하이드록실라제 1 (tph1)의 결정질 스피로사이클릭 화합물 억제제 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| FR2299028A1 (fr) | 1975-02-03 | 1976-08-27 | Rhone Poulenc Ind | Nouvea |
| 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 CN CNB018062156A patent/CN1261419C/zh not_active Expired - Fee Related
- 2001-02-20 PL PL35970201A patent/PL359702A1/xx not_active IP Right Cessation
- 2001-02-20 RU RU2002126556/04A patent/RU2281283C2/ru not_active IP Right Cessation
- 2001-02-20 AT AT01905805T patent/ATE267184T1/de not_active IP Right Cessation
- 2001-02-20 JP JP2001565347A patent/JP2003525931A/ja not_active Abandoned
- 2001-02-20 AU AU33787/01A patent/AU784827B2/en not_active Ceased
- 2001-02-20 DK DK01905805T patent/DK1263745T3/da active
- 2001-02-20 KR KR1020027011634A patent/KR100790763B1/ko not_active IP Right Cessation
- 2001-02-20 EP EP01905805A patent/EP1263745B1/de not_active Expired - Lifetime
- 2001-02-20 CA CA002401953A patent/CA2401953A1/en not_active Abandoned
- 2001-02-20 IL IL151518A patent/IL151518A/en not_active IP Right Cessation
- 2001-02-20 MX MXPA02008038A patent/MXPA02008038A/es active IP Right Grant
- 2001-02-20 HU HU0302772A patent/HUP0302772A3/hu unknown
- 2001-02-20 BR BR0108974-9A patent/BR0108974A/pt not_active IP Right Cessation
- 2001-02-20 YU YU57802A patent/YU57802A/sh unknown
- 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 EE EEP200200498A patent/EE04877B1/xx not_active IP Right Cessation
- 2001-02-20 NZ NZ521207A patent/NZ521207A/en unknown
- 2001-02-20 DE DE50102325T patent/DE50102325D1/de not_active Expired - Lifetime
- 2001-02-20 ES ES01905805T patent/ES2218383T3/es not_active Expired - Lifetime
- 2001-02-20 SK SK1275-2002A patent/SK12752002A3/sk unknown
- 2001-02-20 PT PT01905805T patent/PT1263745E/pt unknown
- 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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