HRP20040783A2 - Use of substituted 3-phenyl-5-alkoxy-1,3,4-oxdiazole-2-one for producing medicaments that inhibit pancreatic lipase - Google Patents
Use of substituted 3-phenyl-5-alkoxy-1,3,4-oxdiazole-2-one for producing medicaments that inhibit pancreatic lipase Download PDFInfo
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- HRP20040783A2 HRP20040783A2 HR20040783A HRP20040783A HRP20040783A2 HR P20040783 A2 HRP20040783 A2 HR P20040783A2 HR 20040783 A HR20040783 A HR 20040783A HR P20040783 A HRP20040783 A HR P20040783A HR P20040783 A2 HRP20040783 A2 HR P20040783A2
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- HR
- Croatia
- Prior art keywords
- alkyl
- substituted
- aryl
- phenyl
- halogen
- Prior art date
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- 102000019280 Pancreatic lipases Human genes 0.000 title claims description 20
- 108050006759 Pancreatic lipases Proteins 0.000 title claims description 20
- 229940116369 pancreatic lipase Drugs 0.000 title claims description 20
- 239000003814 drug Substances 0.000 title claims description 15
- -1 C1-C4-alkyloxy Chemical group 0.000 claims description 114
- 150000001875 compounds Chemical class 0.000 claims description 77
- 229910052736 halogen Inorganic materials 0.000 claims description 64
- 150000002367 halogens Chemical group 0.000 claims description 62
- 239000001257 hydrogen Substances 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 60
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 50
- 150000002431 hydrogen Chemical class 0.000 claims description 41
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 31
- 150000003839 salts Chemical class 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 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 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 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 229940079593 drug Drugs 0.000 claims description 13
- 230000002401 inhibitory effect Effects 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
- 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 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims description 3
- 238000011282 treatment Methods 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 claims description 2
- 125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 claims 1
- 238000002844 melting Methods 0.000 description 133
- 230000008018 melting Effects 0.000 description 133
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 239000000203 mixture Substances 0.000 description 30
- 239000003921 oil Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000013543 active substance Substances 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000013067 intermediate product Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000004367 Lipase Substances 0.000 description 6
- 102000004882 Lipase Human genes 0.000 description 6
- 108090001060 Lipase Proteins 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 229940040461 lipase Drugs 0.000 description 6
- 235000019421 lipase Nutrition 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 239000008298 dragée Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
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- 230000005764 inhibitory process Effects 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 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 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- RKENPFBMIMYICS-UHFFFAOYSA-N [4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)-2-methylphenyl]carbamic acid Chemical compound O=C1OC(OC)=NN1C1=CC=C(NC(O)=O)C(C)=C1 RKENPFBMIMYICS-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000002585 base Substances 0.000 description 3
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- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
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- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CXMSKBSKYRABJH-UHFFFAOYSA-N 1-nitro-4-(3,3,5,5-tetramethylcyclohexyl)oxybenzene Chemical compound C1C(C)(C)CC(C)(C)CC1OC1=CC=C([N+]([O-])=O)C=C1 CXMSKBSKYRABJH-UHFFFAOYSA-N 0.000 description 2
- LAHZJDRGFUXNKQ-UHFFFAOYSA-N 4-(3,3,5,5-tetramethylcyclohexyl)oxyaniline Chemical compound C1C(C)(C)CC(C)(C)CC1OC1=CC=C(N)C=C1 LAHZJDRGFUXNKQ-UHFFFAOYSA-N 0.000 description 2
- GGWFTNFAHXOEBR-UHFFFAOYSA-N 4-(4-chlorophenoxy)-3-nitroaniline Chemical compound [O-][N+](=O)C1=CC(N)=CC=C1OC1=CC=C(Cl)C=C1 GGWFTNFAHXOEBR-UHFFFAOYSA-N 0.000 description 2
- LDBBCISSYGDVIH-UHFFFAOYSA-N 4-(4-fluorophenyl)sulfonylmorpholine Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1CCOCC1 LDBBCISSYGDVIH-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
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- INDBNDHPIXAFCP-UHFFFAOYSA-N (3-fluoro-4-nitrophenyl)hydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C(F)=C1 INDBNDHPIXAFCP-UHFFFAOYSA-N 0.000 description 1
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- 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
- WGICMODWVKZJSF-UHFFFAOYSA-N methyl n-(3-methyl-4-nitroanilino)carbamate Chemical compound COC(=O)NNC1=CC=C([N+]([O-])=O)C(C)=C1 WGICMODWVKZJSF-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
- XMTJPXYNFWIJDV-UHFFFAOYSA-N methyl n-[3-(4-benzylpiperazin-1-yl)-4-nitroanilino]carbamate Chemical compound COC(=O)NNC1=CC=C([N+]([O-])=O)C(N2CCN(CC=3C=CC=CC=3)CC2)=C1 XMTJPXYNFWIJDV-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
- UCFSVTJWVASZPV-UHFFFAOYSA-N methyl n-[3-[(4-fluorophenyl)methoxy]-4-nitroanilino]carbamate Chemical compound COC(=O)NNC1=CC=C([N+]([O-])=O)C(OCC=2C=CC(F)=CC=2)=C1 UCFSVTJWVASZPV-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
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000007932 molded tablet Substances 0.000 description 1
- LBDGRCBSCIFWBO-UHFFFAOYSA-N n-[4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)phenyl]-2,3-diphenylpropanamide Chemical compound O=C1OC(OC)=NN1C(C=C1)=CC=C1NC(=O)C(C=1C=CC=CC=1)CC1=CC=CC=C1 LBDGRCBSCIFWBO-UHFFFAOYSA-N 0.000 description 1
- BVXKRNWDEVBNRO-UHFFFAOYSA-N n-[4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)phenyl]-2,4,6-trimethylbenzamide Chemical compound O=C1OC(OC)=NN1C(C=C1)=CC=C1NC(=O)C1=C(C)C=C(C)C=C1C BVXKRNWDEVBNRO-UHFFFAOYSA-N 0.000 description 1
- JMWJWFLOJPOSAJ-UHFFFAOYSA-N n-[4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)phenyl]-3,3,3-triphenylpropanamide Chemical compound O=C1OC(OC)=NN1C(C=C1)=CC=C1NC(=O)CC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 JMWJWFLOJPOSAJ-UHFFFAOYSA-N 0.000 description 1
- PAQAULLUNKRTHA-UHFFFAOYSA-N n-[4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)phenyl]nonanamide Chemical compound C1=CC(NC(=O)CCCCCCCC)=CC=C1N1C(=O)OC(OC)=N1 PAQAULLUNKRTHA-UHFFFAOYSA-N 0.000 description 1
- VSECUSXXIQWWIY-UHFFFAOYSA-N n-[4-(5-methoxy-2-oxo-1,3,4-oxadiazol-3-yl)phenyl]undecanamide Chemical compound C1=CC(NC(=O)CCCCCCCCCC)=CC=C1N1C(=O)OC(OC)=N1 VSECUSXXIQWWIY-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 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
- 210000000496 pancreas Anatomy 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 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
- LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 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
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
Classifications
-
- 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
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10208986A DE10208986A1 (de) | 2002-02-28 | 2002-02-28 | Verwendung substituierter 3-Phenyl-5-alkoxi-1,3,4-oxdiazol-2-one zur Herstellung von Arzneimitteln mit hemmender Wirkung an der pankreatischen Lipase |
| PCT/EP2003/001560 WO2003072098A1 (de) | 2002-02-28 | 2003-02-17 | Verwendung substituierter 3-phenyl-5-alkoxy-1,3,4-oxdiazol-2-one zur herstellung von arzneimitteln mit hemmender wirkung an der pankreatischen lipase |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20040783A2 true HRP20040783A2 (en) | 2005-04-30 |
Family
ID=27740557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20040783A HRP20040783A2 (en) | 2002-02-28 | 2004-08-27 | Use of substituted 3-phenyl-5-alkoxy-1,3,4-oxdiazole-2-one for producing medicaments that inhibit pancreatic lipase |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP1482929A1 (de) |
| JP (1) | JP2005519079A (de) |
| KR (1) | KR20040101250A (de) |
| CN (1) | CN1638766A (de) |
| AR (1) | AR038702A1 (de) |
| AU (1) | AU2003210292A1 (de) |
| BR (1) | BR0308045A (de) |
| CA (1) | CA2477005A1 (de) |
| CO (1) | CO5611144A2 (de) |
| DE (1) | DE10208986A1 (de) |
| HR (1) | HRP20040783A2 (de) |
| HU (1) | HUP0500093A2 (de) |
| IL (1) | IL163719A0 (de) |
| MA (1) | MA27173A1 (de) |
| MX (1) | MXPA04007480A (de) |
| NO (1) | NO20044091L (de) |
| PL (1) | PL371310A1 (de) |
| RU (1) | RU2004128932A (de) |
| TW (1) | TW200400026A (de) |
| WO (1) | WO2003072098A1 (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL1765327T3 (pl) | 2004-06-17 | 2015-01-30 | Cytokinetics Inc | Związki, kompozycje i sposoby |
| 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 |
| ES2419007T3 (es) | 2005-12-15 | 2013-08-19 | Cytokinetics, Inc. | Ciertas entidades químicas, composiciones y procedimientos |
| US7825120B2 (en) | 2005-12-15 | 2010-11-02 | Cytokinetics, Inc. | Certain substituted ((piperazin-1-ylmethyl)benzyl)ureas |
| WO2007078839A2 (en) | 2005-12-19 | 2007-07-12 | Cytokinetics, Inc. | Compounds, compositions and methods |
| WO2009081891A1 (ja) * | 2007-12-25 | 2009-07-02 | Kissei Pharmaceutical Co., Ltd. | 新規なカテコール誘導体、それを含有する医薬組成物およびそれらの用途 |
| 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 |
| CN103086859B (zh) * | 2011-11-08 | 2015-11-11 | 清华大学 | 2,4-二羟基-5,6-取代-1-卤代苯衍生物、其合成方法及其应用 |
| US20230271915A1 (en) * | 2017-09-01 | 2023-08-31 | Curtin University | Synthetic derivatives of oleoyl-lysophosphatidylinositol (oleoyl-lpi) and uses thereof |
| CN109879839B (zh) * | 2019-03-12 | 2023-04-25 | 沈阳大学 | 6-哌嗪甲基-7-羟基苯并呋喃类化合物及其医药用途 |
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 |
| ATE267184T1 (de) * | 2000-03-07 | 2004-06-15 | Aventis Pharma 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 DE10208986A patent/DE10208986A1/de not_active Withdrawn
-
2003
- 2003-02-17 CA CA002477005A patent/CA2477005A1/en not_active Abandoned
- 2003-02-17 EP EP03742942A patent/EP1482929A1/de not_active Withdrawn
- 2003-02-17 PL PL03371310A patent/PL371310A1/xx not_active Application Discontinuation
- 2003-02-17 IL IL16371903A patent/IL163719A0/xx unknown
- 2003-02-17 MX MXPA04007480A patent/MXPA04007480A/es unknown
- 2003-02-17 AU AU2003210292A patent/AU2003210292A1/en not_active Abandoned
- 2003-02-17 WO PCT/EP2003/001560 patent/WO2003072098A1/de not_active Application Discontinuation
- 2003-02-17 CN CNA038047675A patent/CN1638766A/zh active Pending
- 2003-02-17 RU RU2004128932/15A patent/RU2004128932A/ru not_active Application Discontinuation
- 2003-02-17 KR KR10-2004-7013470A patent/KR20040101250A/ko not_active Application Discontinuation
- 2003-02-17 HU HU0500093A patent/HUP0500093A2/hu unknown
- 2003-02-17 JP JP2003570844A patent/JP2005519079A/ja not_active Withdrawn
- 2003-02-17 BR BR0308045-5A patent/BR0308045A/pt not_active Application Discontinuation
- 2003-02-26 TW TW092103972A patent/TW200400026A/zh unknown
- 2003-02-26 AR ARP030100625A patent/AR038702A1/es unknown
-
2004
- 2004-07-27 MA MA27804A patent/MA27173A1/fr unknown
- 2004-08-26 CO CO04083781A patent/CO5611144A2/es not_active Application Discontinuation
- 2004-08-27 HR HR20040783A patent/HRP20040783A2/hr not_active Application Discontinuation
- 2004-09-27 NO NO20044091A patent/NO20044091L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1482929A1 (de) | 2004-12-08 |
| PL371310A1 (en) | 2005-06-13 |
| WO2003072098A1 (de) | 2003-09-04 |
| MXPA04007480A (es) | 2004-11-10 |
| AU2003210292A1 (en) | 2003-09-09 |
| CO5611144A2 (es) | 2006-02-28 |
| DE10208986A1 (de) | 2003-09-11 |
| IL163719A0 (en) | 2005-12-18 |
| NO20044091L (no) | 2004-09-27 |
| RU2004128932A (ru) | 2005-04-10 |
| MA27173A1 (fr) | 2005-01-03 |
| KR20040101250A (ko) | 2004-12-02 |
| CA2477005A1 (en) | 2003-09-04 |
| AR038702A1 (es) | 2005-01-26 |
| TW200400026A (en) | 2004-01-01 |
| JP2005519079A (ja) | 2005-06-30 |
| BR0308045A (pt) | 2004-12-21 |
| HUP0500093A2 (hu) | 2005-04-28 |
| CN1638766A (zh) | 2005-07-13 |
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