CA2477031A1 - Substituted 3-phenyl-5-alkoxy-1,3,4-oxadiazol-2-ones, the production thereof and their use in medicaments - Google Patents
Substituted 3-phenyl-5-alkoxy-1,3,4-oxadiazol-2-ones, the production thereof and their use in medicaments Download PDFInfo
- Publication number
- CA2477031A1 CA2477031A1 CA002477031A CA2477031A CA2477031A1 CA 2477031 A1 CA2477031 A1 CA 2477031A1 CA 002477031 A CA002477031 A CA 002477031A CA 2477031 A CA2477031 A CA 2477031A CA 2477031 A1 CA2477031 A1 CA 2477031A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- alkyl
- phenyl
- compound
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000003814 drug Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 208000008589 Obesity Diseases 0.000 claims abstract description 3
- 235000020824 obesity Nutrition 0.000 claims abstract description 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 2
- -1 chlorophenoxy Chemical group 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- 150000002429 hydrazines Chemical class 0.000 claims description 3
- 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
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 102000019280 Pancreatic lipases Human genes 0.000 abstract description 12
- 108050006759 Pancreatic lipases Proteins 0.000 abstract description 12
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- 230000002401 inhibitory effect Effects 0.000 abstract description 6
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 239000013543 active substance Substances 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000004104 aryloxy group Chemical group 0.000 abstract 2
- 239000000203 mixture Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- 239000008194 pharmaceutical composition Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
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- 102000004882 Lipase Human genes 0.000 description 6
- 108090001060 Lipase Proteins 0.000 description 6
- 239000004367 Lipase Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229940049964 oleate Drugs 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 239000000651 prodrug Substances 0.000 description 3
- 229940002612 prodrug Drugs 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000007493 shaping process Methods 0.000 description 3
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- 239000000758 substrate Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 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
- 244000215068 Acacia senegal Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
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- 229910052794 bromium Inorganic materials 0.000 description 2
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- 239000012530 fluid Substances 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
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- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- WWQYTEPUEUNBOM-SANMLTNESA-N (2,5-dioxopyrrolidin-1-yl) (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-(1h-indol-3-yl)propanoate Chemical compound O=C([C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21)ON1C(=O)CCC1=O WWQYTEPUEUNBOM-SANMLTNESA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- JSMHDBKKRKIODL-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-5-dodecoxy-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCCCC)=NN1C1=CC=C(Cl)C(Cl)=C1 JSMHDBKKRKIODL-UHFFFAOYSA-N 0.000 description 1
- XFXATWRVESLWOD-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-dodecoxy-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCCCC)=NN1C1=CC(Cl)=CC(Cl)=C1 XFXATWRVESLWOD-UHFFFAOYSA-N 0.000 description 1
- MSJAIQHIBPBEEV-UHFFFAOYSA-N 3-(3-fluorophenyl)-5-hexadecoxy-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCCCCCCCC)=NN1C1=CC=CC(F)=C1 MSJAIQHIBPBEEV-UHFFFAOYSA-N 0.000 description 1
- DXNJIIBCBHPGSQ-UHFFFAOYSA-N 3-[3,5-bis(trifluoromethyl)phenyl]-5-dodecoxy-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCCCC)=NN1C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 DXNJIIBCBHPGSQ-UHFFFAOYSA-N 0.000 description 1
- USVHPVMUQWBGMQ-UHFFFAOYSA-N 3-[4-(4-chlorophenoxy)phenyl]-5-hexadecoxy-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCCCCCCCC)=NN1C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 USVHPVMUQWBGMQ-UHFFFAOYSA-N 0.000 description 1
- ZWGZPZUDKAILJM-UHFFFAOYSA-N 3-[4-(trifluoromethoxy)phenyl]-5-undecoxy-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCCC)=NN1C1=CC=C(OC(F)(F)F)C=C1 ZWGZPZUDKAILJM-UHFFFAOYSA-N 0.000 description 1
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- KTEODHASAFPODP-UHFFFAOYSA-N 5-(2-butoxyethoxy)-3-[4-(trifluoromethoxy)phenyl]-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCOCCCC)=NN1C1=CC=C(OC(F)(F)F)C=C1 KTEODHASAFPODP-UHFFFAOYSA-N 0.000 description 1
- KAWBGZHWHSUWLS-UHFFFAOYSA-N 5-(2-docosoxyethoxy)-3-[4-(trifluoromethoxy)phenyl]-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCOCCCCCCCCCCCCCCCCCCCCCC)=NN1C1=CC=C(OC(F)(F)F)C=C1 KAWBGZHWHSUWLS-UHFFFAOYSA-N 0.000 description 1
- FCHJQWWCWWMWIO-UHFFFAOYSA-N 5-(2-dodecoxyethoxy)-3-[4-(trifluoromethoxy)phenyl]-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCOCCCCCCCCCCCC)=NN1C1=CC=C(OC(F)(F)F)C=C1 FCHJQWWCWWMWIO-UHFFFAOYSA-N 0.000 description 1
- ANEHBGWFDKFACL-UHFFFAOYSA-N 5-(2-naphthalen-1-yloxyethoxy)-3-[4-(trifluoromethoxy)phenyl]-1,3,4-oxadiazol-2-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1N1C(=O)OC(OCCOC=2C3=CC=CC=C3C=CC=2)=N1 ANEHBGWFDKFACL-UHFFFAOYSA-N 0.000 description 1
- CXWCAERLHPSWPE-UHFFFAOYSA-N 5-(3-phenoxyphenoxy)-3-[4-(trifluoromethoxy)phenyl]-1,3,4-oxadiazol-2-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1N1C(=O)OC(OC=2C=C(OC=3C=CC=CC=3)C=CC=2)=N1 CXWCAERLHPSWPE-UHFFFAOYSA-N 0.000 description 1
- USJCNWJSEUOJHB-UHFFFAOYSA-N 5-(4-octylphenoxy)-3-[4-(trifluoromethoxy)phenyl]-1,3,4-oxadiazol-2-one Chemical compound C1=CC(CCCCCCCC)=CC=C1OC(OC1=O)=NN1C1=CC=C(OC(F)(F)F)C=C1 USJCNWJSEUOJHB-UHFFFAOYSA-N 0.000 description 1
- CFRTWRNZFNJJQX-UHFFFAOYSA-N 5-(7-phenylheptoxy)-3-[4-(trifluoromethoxy)phenyl]-1,3,4-oxadiazol-2-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1N1C(=O)OC(OCCCCCCCC=2C=CC=CC=2)=N1 CFRTWRNZFNJJQX-UHFFFAOYSA-N 0.000 description 1
- VJPXSIAXZGJFFS-KTKRTIGZSA-N 5-[(z)-octadec-9-enoxy]-3-[4-(trifluoromethoxy)phenyl]-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCC\C=C/CCCCCCCC)=NN1C1=CC=C(OC(F)(F)F)C=C1 VJPXSIAXZGJFFS-KTKRTIGZSA-N 0.000 description 1
- RCSTXABZZTZXMV-UHFFFAOYSA-N 5-[2-(2-hexoxyethoxy)ethoxy]-3-[4-(trifluoromethoxy)phenyl]-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCOCCOCCCCCC)=NN1C1=CC=C(OC(F)(F)F)C=C1 RCSTXABZZTZXMV-UHFFFAOYSA-N 0.000 description 1
- VORQVZRCSGBZKE-UHFFFAOYSA-N 5-decoxy-3-[4-(trifluoromethoxy)phenyl]-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCC)=NN1C1=CC=C(OC(F)(F)F)C=C1 VORQVZRCSGBZKE-UHFFFAOYSA-N 0.000 description 1
- AVCWQAFZYHEIDX-UHFFFAOYSA-N 5-dodecoxy-3-(3-fluorophenyl)-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCCCC)=NN1C1=CC=CC(F)=C1 AVCWQAFZYHEIDX-UHFFFAOYSA-N 0.000 description 1
- YOZKBGNPARHOOJ-UHFFFAOYSA-N 5-dodecoxy-3-(3-methoxyphenyl)-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCCCC)=NN1C1=CC=CC(OC)=C1 YOZKBGNPARHOOJ-UHFFFAOYSA-N 0.000 description 1
- DFJDTKQNVOIBSM-UHFFFAOYSA-N 5-dodecoxy-3-(4-methoxyphenyl)-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCCCC)=NN1C1=CC=C(OC)C=C1 DFJDTKQNVOIBSM-UHFFFAOYSA-N 0.000 description 1
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- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
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- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
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- 241000124008 Mammalia Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
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- 239000004743 Polypropylene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 102000000019 Sterol Esterase Human genes 0.000 description 1
- 108010055297 Sterol Esterase Proteins 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 description 1
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- ODUIXUGXPFKQLG-QWRGUYRKSA-N [2-(4-chloro-2-fluoroanilino)-5-methyl-1,3-thiazol-4-yl]-[(2s,3s)-2,3-dimethylpiperidin-1-yl]methanone Chemical compound C[C@H]1[C@@H](C)CCCN1C(=O)C1=C(C)SC(NC=2C(=CC(Cl)=CC=2)F)=N1 ODUIXUGXPFKQLG-QWRGUYRKSA-N 0.000 description 1
- GWFWCTYACJWQKP-UHFFFAOYSA-N [4-(trifluoromethoxy)phenyl]hydrazine Chemical compound NNC1=CC=C(OC(F)(F)F)C=C1 GWFWCTYACJWQKP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 229920006318 anionic polymer Polymers 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 238000003705 background correction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000001952 enzyme assay Methods 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000000543 intermediate 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
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940068917 polyethylene glycols Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229940100467 polyvinyl acetate phthalate Drugs 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid group Chemical group S(N)(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 229960001947 tripalmitin Drugs 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 239000007762 w/o emulsion Substances 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4245—Oxadiazoles
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10208987A DE10208987A1 (de) | 2002-02-28 | 2002-02-28 | Substituierte 3-Phenyl-5-alkoxi-1,3,4-oxidiazol-2-one, ihre Herstellung und Verwendung in Arzneistoffen |
| DE10208987.6 | 2002-02-28 | ||
| PCT/EP2003/001484 WO2003072555A1 (de) | 2002-02-28 | 2003-02-14 | Substituierte 3-phenyl-5-alkoxy-1,3,4-oxadiazol-2-one sowie ihre herstellung und verwendung in arzneistoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2477031A1 true CA2477031A1 (en) | 2003-09-04 |
Family
ID=27740558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002477031A Abandoned CA2477031A1 (en) | 2002-02-28 | 2003-02-14 | Substituted 3-phenyl-5-alkoxy-1,3,4-oxadiazol-2-ones, the production thereof and their use in medicaments |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP1480960B1 (https=) |
| JP (1) | JP4486363B2 (https=) |
| KR (1) | KR20040095240A (https=) |
| CN (1) | CN1639137A (https=) |
| AR (1) | AR038701A1 (https=) |
| AT (1) | ATE557012T1 (https=) |
| AU (1) | AU2003226977A1 (https=) |
| BR (1) | BR0307921A (https=) |
| CA (1) | CA2477031A1 (https=) |
| CO (1) | CO5611146A2 (https=) |
| DE (1) | DE10208987A1 (https=) |
| HR (1) | HRP20040782A2 (https=) |
| HU (1) | HUP0402671A3 (https=) |
| IL (1) | IL163683A0 (https=) |
| MA (1) | MA27172A1 (https=) |
| MX (1) | MXPA04007960A (https=) |
| NO (1) | NO20044090L (https=) |
| PE (1) | PE20030928A1 (https=) |
| PL (1) | PL370423A1 (https=) |
| RU (1) | RU2004128933A (https=) |
| TW (1) | TW200400951A (https=) |
| WO (1) | WO2003072555A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7074822B2 (en) | 2004-02-23 | 2006-07-11 | Solvay Pharmaceuticals Gmbh | Alkyl carbamate-substituted β-lactones, process for their preparation, and pharmaceutical compositions containing them |
| JP2008517976A (ja) | 2004-10-25 | 2008-05-29 | ゾルファイ ファーマスーティカルズ ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｂ１カンナビノイド受容体拮抗薬及びカリウムチャンネルオープナーから成る、真性糖尿病１型、肥満及び関連症状の治療用の医薬組成物 |
| JP2011507952A (ja) * | 2007-12-27 | 2011-03-10 | バイアル−ポルテラ アンド シーエー，エス．エー． | 医療用途用５−ｏ−置換３−ｎ−フェニル−１、３、４−オキサジアゾロン類 |
| 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 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19942354A1 (de) * | 1999-09-04 | 2001-03-08 | Aventis Pharma Gmbh | Substituierte 3-Phenyl-5-alkoxi-1,3,4-oxdiazol-2-one, ihre Herstellung und Verwendung in Arzneimitteln |
| TR200401217T4 (tr) * | 2000-03-07 | 2004-06-21 | Aventis Pharma Deutschland Gmbh | İkameli 3-Fenil-5-Alkoksi-1,3,4-Oksdiazol-2-one (ve) hormona duyarlı lipazın önlenmesinde kullanılması |
-
2002
- 2002-02-28 DE DE10208987A patent/DE10208987A1/de not_active Withdrawn
-
2003
- 2003-02-05 PE PE2003000134A patent/PE20030928A1/es not_active Application Discontinuation
- 2003-02-14 HR HR20040782A patent/HRP20040782A2/hr not_active Application Discontinuation
- 2003-02-14 AT AT03742936T patent/ATE557012T1/de active
- 2003-02-14 AU AU2003226977A patent/AU2003226977A1/en not_active Abandoned
- 2003-02-14 WO PCT/EP2003/001484 patent/WO2003072555A1/de not_active Ceased
- 2003-02-14 JP JP2003571261A patent/JP4486363B2/ja not_active Expired - Fee Related
- 2003-02-14 MX MXPA04007960A patent/MXPA04007960A/es unknown
- 2003-02-14 EP EP03742936A patent/EP1480960B1/de not_active Expired - Lifetime
- 2003-02-14 CN CNA038047837A patent/CN1639137A/zh active Pending
- 2003-02-14 KR KR10-2004-7013485A patent/KR20040095240A/ko not_active Withdrawn
- 2003-02-14 IL IL16368303A patent/IL163683A0/xx unknown
- 2003-02-14 PL PL03370423A patent/PL370423A1/xx not_active Application Discontinuation
- 2003-02-14 HU HU0402671A patent/HUP0402671A3/hu unknown
- 2003-02-14 CA CA002477031A patent/CA2477031A1/en not_active Abandoned
- 2003-02-14 BR BR0307921-0A patent/BR0307921A/pt not_active Application Discontinuation
- 2003-02-14 RU RU2004128933/04A patent/RU2004128933A/ru not_active Application Discontinuation
- 2003-02-26 TW TW092103969A patent/TW200400951A/zh unknown
- 2003-02-26 AR ARP030100624A patent/AR038701A1/es unknown
-
2004
- 2004-07-27 MA MA27803A patent/MA27172A1/fr unknown
- 2004-08-26 CO CO04083779A patent/CO5611146A2/es not_active Application Discontinuation
- 2004-09-27 NO NO20044090A patent/NO20044090L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| TW200400951A (en) | 2004-01-16 |
| AU2003226977A1 (en) | 2003-09-09 |
| BR0307921A (pt) | 2004-12-21 |
| IL163683A0 (en) | 2005-12-18 |
| ATE557012T1 (de) | 2012-05-15 |
| HUP0402671A3 (en) | 2006-07-28 |
| JP2005519085A (ja) | 2005-06-30 |
| MXPA04007960A (es) | 2004-11-26 |
| EP1480960A1 (de) | 2004-12-01 |
| AR038701A1 (es) | 2005-01-26 |
| WO2003072555A1 (de) | 2003-09-04 |
| JP4486363B2 (ja) | 2010-06-23 |
| MA27172A1 (fr) | 2005-01-03 |
| PL370423A1 (en) | 2005-05-30 |
| NO20044090L (no) | 2004-11-04 |
| CN1639137A (zh) | 2005-07-13 |
| EP1480960B1 (de) | 2012-05-09 |
| PE20030928A1 (es) | 2003-12-17 |
| DE10208987A1 (de) | 2003-09-11 |
| CO5611146A2 (es) | 2006-02-28 |
| RU2004128933A (ru) | 2005-04-20 |
| HRP20040782A2 (en) | 2005-02-28 |
| HUP0402671A2 (hu) | 2005-04-28 |
| KR20040095240A (ko) | 2004-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |