MXPA04007960A - 3-fenil-5-alcoxi-1,3,4-oxadiazol-2-onas sustituidas, su produccion y su uso en medicamentos. - Google Patents
3-fenil-5-alcoxi-1,3,4-oxadiazol-2-onas sustituidas, su produccion y su uso en medicamentos.Info
- Publication number
- MXPA04007960A MXPA04007960A MXPA04007960A MXPA04007960A MXPA04007960A MX PA04007960 A MXPA04007960 A MX PA04007960A MX PA04007960 A MXPA04007960 A MX PA04007960A MX PA04007960 A MXPA04007960 A MX PA04007960A MX PA04007960 A MXPA04007960 A MX PA04007960A
- Authority
- MX
- Mexico
- Prior art keywords
- group
- formula
- substituted
- compound
- alkyl
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 102000019280 Pancreatic lipases Human genes 0.000 claims abstract description 13
- 108050006759 Pancreatic lipases Proteins 0.000 claims abstract description 13
- 229940116369 pancreatic lipase Drugs 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 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 8
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract description 4
- 208000008589 Obesity Diseases 0.000 claims abstract description 4
- 235000020824 obesity Nutrition 0.000 claims abstract description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- -1 chlorophenoxy group Chemical group 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 150000002148 esters Chemical class 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
- 238000011282 treatment Methods 0.000 claims description 3
- 238000007385 chemical modification Methods 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 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
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 5
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 abstract description 2
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 8
- 239000008194 pharmaceutical composition Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical class ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 102000004882 Lipase Human genes 0.000 description 6
- 108090001060 Lipase Proteins 0.000 description 6
- 239000004367 Lipase Substances 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 229940040461 lipase Drugs 0.000 description 6
- 235000019421 lipase Nutrition 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 230000037396 body weight Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000000651 prodrug Substances 0.000 description 3
- 229940002612 prodrug Drugs 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- DAQCUXYFZBBWOG-UHFFFAOYSA-N 5-dodecoxy-3-[4-(trifluoromethoxy)phenyl]-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCCCC)=NN1C1=CC=C(OC(F)(F)F)C=C1 DAQCUXYFZBBWOG-UHFFFAOYSA-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
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000007891 compressed tablet Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 229940049964 oleate Drugs 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 239000006174 pH buffer Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000007493 shaping process Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229960004793 sucrose Drugs 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 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
- 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 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-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
- 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
- QLCWFCMKOBSFOZ-UHFFFAOYSA-N 3-(3-fluorophenyl)-5-octoxy-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCC)=NN1C1=CC=CC(F)=C1 QLCWFCMKOBSFOZ-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
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 description 1
- WDRJNKMAZMEYOF-UHFFFAOYSA-N 4-(trifluoromethoxy)phenol Chemical compound OC1=CC=C(OC(F)(F)F)C=C1 WDRJNKMAZMEYOF-UHFFFAOYSA-N 0.000 description 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 description 1
- 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
- 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
- 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
- JYEIXTIYFRUDMV-UHFFFAOYSA-N 5-dodecoxy-3-(3-methyl-4-nitrophenyl)-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCCCC)=NN1C1=CC=C([N+]([O-])=O)C(C)=C1 JYEIXTIYFRUDMV-UHFFFAOYSA-N 0.000 description 1
- VRIHMKLCOJEQDE-UHFFFAOYSA-N 5-dodecoxy-3-(3-nitrophenyl)-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCCCC)=NN1C1=CC=CC([N+]([O-])=O)=C1 VRIHMKLCOJEQDE-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
- KZSGDHSOIULPGW-UHFFFAOYSA-N 5-dodecoxy-3-(4-phenylmethoxyphenyl)-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCCCC)=NN1C(C=C1)=CC=C1OCC1=CC=CC=C1 KZSGDHSOIULPGW-UHFFFAOYSA-N 0.000 description 1
- ZXBXMCCGRVLPFN-UHFFFAOYSA-N 5-hexadecoxy-3-(3-phenylmethoxyphenyl)-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCCCCCCCC)=NN1C1=CC=CC(OCC=2C=CC=CC=2)=C1 ZXBXMCCGRVLPFN-UHFFFAOYSA-N 0.000 description 1
- HKIIVKOWULQILO-UHFFFAOYSA-N 5-hexadecoxy-3-(4-methoxyphenyl)-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCCCCCCCC)=NN1C1=CC=C(OC)C=C1 HKIIVKOWULQILO-UHFFFAOYSA-N 0.000 description 1
- AZTCGCZGIUAACA-UHFFFAOYSA-N 5-hexadecoxy-3-(4-nitrophenyl)-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCCCCCCCC)=NN1C1=CC=C([N+]([O-])=O)C=C1 AZTCGCZGIUAACA-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (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 (2)
| 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 |
| 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 |
|---|---|
| MXPA04007960A true MXPA04007960A (es) | 2004-11-26 |
Family
ID=27740558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA04007960A MXPA04007960A (es) | 2002-02-28 | 2003-02-14 | 3-fenil-5-alcoxi-1,3,4-oxadiazol-2-onas sustituidas, su produccion y su uso en medicamentos. |
Country Status (22)
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| 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 |
| RU2007119315A (ru) | 2004-10-25 | 2008-11-27 | Зольвай Фармасьютиклз Гмбх (De) | Фармацевтические композиции, содержащие антагонисты каннабиноидного рецептора св1 и открыватели калиевых каналов, предназначенные для лечения сахарного диабета типа i, ожирения и связанных с ними состояний |
| BRPI0821482A2 (pt) * | 2007-12-27 | 2015-07-14 | Bial Portela & Ca Sa | 3-n-fenil-1,3,4-oxadiazolona 5-o-substituída, seu uso, sua composição e seu processo de preparação |
| AR074978A1 (es) | 2008-12-23 | 2011-03-02 | Bial Portela & Ca Sa | 3-n-aril-1,3,4-oxadiazolonas 5-o-sustituidas para uso en el tratamiento del dolor y procedimiento de obtencion |
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| 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 |
| WO2001066531A1 (de) * | 2000-03-07 | 2001-09-13 | Aventis Pharma Deutschland Gmbh | Substituierte 3-phenyl-5-alkoxi-1,3,4-oxdiazol-2-one (und) ihre verwendung zur hemmung der hormonsensitiven lipase |
-
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 MX MXPA04007960A patent/MXPA04007960A/es unknown
- 2003-02-14 IL IL16368303A patent/IL163683A0/xx unknown
- 2003-02-14 JP JP2003571261A patent/JP4486363B2/ja not_active Expired - Fee Related
- 2003-02-14 RU RU2004128933/04A patent/RU2004128933A/ru not_active Application Discontinuation
- 2003-02-14 CN CNA038047837A patent/CN1639137A/zh active Pending
- 2003-02-14 AT AT03742936T patent/ATE557012T1/de active
- 2003-02-14 KR KR10-2004-7013485A patent/KR20040095240A/ko not_active Withdrawn
- 2003-02-14 BR BR0307921-0A patent/BR0307921A/pt not_active Application Discontinuation
- 2003-02-14 CA CA002477031A patent/CA2477031A1/en not_active Abandoned
- 2003-02-14 WO PCT/EP2003/001484 patent/WO2003072555A1/de not_active Ceased
- 2003-02-14 PL PL03370423A patent/PL370423A1/xx not_active Application Discontinuation
- 2003-02-14 HU HU0402671A patent/HUP0402671A3/hu unknown
- 2003-02-14 HR HR20040782A patent/HRP20040782A2/hr not_active Application Discontinuation
- 2003-02-14 AU AU2003226977A patent/AU2003226977A1/en not_active Abandoned
- 2003-02-14 EP EP03742936A patent/EP1480960B1/de not_active Expired - Lifetime
- 2003-02-26 AR ARP030100624A patent/AR038701A1/es unknown
- 2003-02-26 TW TW092103969A patent/TW200400951A/zh 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 |
|---|---|
| EP1480960A1 (de) | 2004-12-01 |
| AR038701A1 (es) | 2005-01-26 |
| CN1639137A (zh) | 2005-07-13 |
| NO20044090L (no) | 2004-11-04 |
| PE20030928A1 (es) | 2003-12-17 |
| BR0307921A (pt) | 2004-12-21 |
| HRP20040782A2 (en) | 2005-02-28 |
| HUP0402671A3 (en) | 2006-07-28 |
| CO5611146A2 (es) | 2006-02-28 |
| TW200400951A (en) | 2004-01-16 |
| JP2005519085A (ja) | 2005-06-30 |
| JP4486363B2 (ja) | 2010-06-23 |
| DE10208987A1 (de) | 2003-09-11 |
| IL163683A0 (en) | 2005-12-18 |
| ATE557012T1 (de) | 2012-05-15 |
| AU2003226977A1 (en) | 2003-09-09 |
| CA2477031A1 (en) | 2003-09-04 |
| WO2003072555A1 (de) | 2003-09-04 |
| EP1480960B1 (de) | 2012-05-09 |
| PL370423A1 (en) | 2005-05-30 |
| MA27172A1 (fr) | 2005-01-03 |
| RU2004128933A (ru) | 2005-04-20 |
| KR20040095240A (ko) | 2004-11-12 |
| HUP0402671A2 (hu) | 2005-04-28 |
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