RU2437877C2 - Новые производные тиофена в качестве агонистов рецептора s1p1/edg1 - Google Patents
Новые производные тиофена в качестве агонистов рецептора s1p1/edg1 Download PDFInfo
- Publication number
- RU2437877C2 RU2437877C2 RU2008132802/04A RU2008132802A RU2437877C2 RU 2437877 C2 RU2437877 C2 RU 2437877C2 RU 2008132802/04 A RU2008132802/04 A RU 2008132802/04A RU 2008132802 A RU2008132802 A RU 2008132802A RU 2437877 C2 RU2437877 C2 RU 2437877C2
- Authority
- RU
- Russia
- Prior art keywords
- isobutyl
- hydroxy
- oxadiazol
- methylthiophen
- compound according
- Prior art date
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- 150000003577 thiophenes Chemical class 0.000 title claims abstract 5
- 101000693265 Homo sapiens Sphingosine 1-phosphate receptor 1 Proteins 0.000 title 1
- 102100025750 Sphingosine 1-phosphate receptor 1 Human genes 0.000 title 1
- 239000000018 receptor agonist Substances 0.000 title 1
- 229940044601 receptor agonist Drugs 0.000 title 1
- -1 2,3-dihydroxypropoxy Chemical group 0.000 claims abstract 36
- 150000001875 compounds Chemical class 0.000 claims abstract 36
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 32
- 239000001257 hydrogen Substances 0.000 claims abstract 32
- 150000002431 hydrogen Chemical class 0.000 claims abstract 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 9
- 150000003839 salts Chemical class 0.000 claims abstract 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 4
- 201000010099 disease Diseases 0.000 claims abstract 4
- 208000035475 disorder Diseases 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 4
- 150000002367 halogens Chemical class 0.000 claims abstract 4
- 210000000987 immune system Anatomy 0.000 claims abstract 4
- 229930192474 thiophene Natural products 0.000 claims abstract 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims abstract 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract 3
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract 2
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims abstract 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 26
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 2
- MDCUXJSPWVQNNI-UHFFFAOYSA-N 1-[3,4-bis(2-methylpropyl)thiophen-2-yl]-3-(4-hydroxy-3,5-dimethylphenyl)propan-1-one Chemical compound CC(C)CC1=CSC(C(=O)CCC=2C=C(C)C(O)=C(C)C=2)=C1CC(C)C MDCUXJSPWVQNNI-UHFFFAOYSA-N 0.000 claims 1
- ADAPMLGFQADHTG-UHFFFAOYSA-N 2-hydroxy-n-[2-hydroxy-3-[3-methoxy-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]propyl]acetamide Chemical compound COC1=CC(OCC(O)CNC(=O)CO)=CC=C1C1=NOC(C=2SC(C)=C(CC(C)C)C=2)=N1 ADAPMLGFQADHTG-UHFFFAOYSA-N 0.000 claims 1
- SSCJNSUMOPTRAW-UHFFFAOYSA-N 3-[2,6-dimethyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]phenoxy]propane-1,2-diol Chemical compound CC(C)CC1=CSC(C=2OC(=NN=2)C=2C=C(C)C(OCC(O)CO)=C(C)C=2)=C1C SSCJNSUMOPTRAW-UHFFFAOYSA-N 0.000 claims 1
- FTBUJOHYQKNAMC-UHFFFAOYSA-N 3-[2,6-dimethyl-4-[5-[4-(2-methylpropyl)-3-propylthiophen-2-yl]-1,3,4-oxadiazol-2-yl]phenoxy]propane-1,2-diol Chemical compound CC(C)CC1=CSC(C=2OC(=NN=2)C=2C=C(C)C(OCC(O)CO)=C(C)C=2)=C1CCC FTBUJOHYQKNAMC-UHFFFAOYSA-N 0.000 claims 1
- WOTLDRBDHUXWGE-UHFFFAOYSA-N 3-[2-ethyl-6-methyl-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenyl]-n-(2-hydroxyethyl)propanamide Chemical compound CC1=C(CCC(=O)NCCO)C(CC)=CC(C=2N=C(ON=2)C=2SC(C)=C(CC(C)C)C=2)=C1 WOTLDRBDHUXWGE-UHFFFAOYSA-N 0.000 claims 1
- JCSASMVQZOFEIX-UHFFFAOYSA-N 3-[3-methoxy-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]propane-1,2-diol Chemical compound COC1=CC(OCC(O)CO)=CC=C1C1=NOC(C=2SC(C)=C(CC(C)C)C=2)=N1 JCSASMVQZOFEIX-UHFFFAOYSA-N 0.000 claims 1
- YAQLSHRLKQDLQB-UHFFFAOYSA-N 3-[4-[5-[3,4-bis(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]-2,6-dimethylphenoxy]propane-1,2-diol Chemical compound CC(C)CC1=CSC(C=2OC(=NN=2)C=2C=C(C)C(OCC(O)CO)=C(C)C=2)=C1CC(C)C YAQLSHRLKQDLQB-UHFFFAOYSA-N 0.000 claims 1
- QQXYBEPBLKPJKL-UHFFFAOYSA-N 3-[4-[5-[3-ethyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]-2,6-dimethylphenoxy]propane-1,2-diol Chemical compound CC(C)CC1=CSC(C=2OC(=NN=2)C=2C=C(C)C(OCC(O)CO)=C(C)C=2)=C1CC QQXYBEPBLKPJKL-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- JGDQODJFFAUBNE-OAQYLSRUSA-N n-[(2r)-3-[2,6-diethyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CCC1=C(OC[C@H](O)CNC(=O)CO)C(CC)=CC(C=2N=C(ON=2)C2=C(C(CC(C)C)=CS2)C)=C1 JGDQODJFFAUBNE-OAQYLSRUSA-N 0.000 claims 1
- IUNDDHWOOJLJCV-QGZVFWFLSA-N n-[(2r)-3-[2-chloro-4-[5-[3,5-dimethyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]-6-methylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=C(C)SC(C=2ON=C(N=2)C=2C=C(Cl)C(OC[C@H](O)CNC(=O)CO)=C(C)C=2)=C1C IUNDDHWOOJLJCV-QGZVFWFLSA-N 0.000 claims 1
- OUIIFEXFZFIDFR-QGZVFWFLSA-N n-[(2r)-3-[2-chloro-6-methyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=CSC(C=2ON=C(N=2)C=2C=C(Cl)C(OC[C@H](O)CNC(=O)CO)=C(C)C=2)=C1C OUIIFEXFZFIDFR-QGZVFWFLSA-N 0.000 claims 1
- UULCTKWNLBKDEG-QGZVFWFLSA-N n-[(2r)-3-[2-chloro-6-methyl-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound S1C(C)=C(CC(C)C)C=C1C1=NC(C=2C=C(Cl)C(OC[C@H](O)CNC(=O)CO)=C(C)C=2)=NO1 UULCTKWNLBKDEG-QGZVFWFLSA-N 0.000 claims 1
- USMRGOCLFZPFTE-HXUWFJFHSA-N n-[(2r)-3-[2-ethyl-6-methyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OC[C@H](O)CNC(=O)CO)C(CC)=CC(C=2N=C(ON=2)C2=C(C(CC(C)C)=CS2)C)=C1 USMRGOCLFZPFTE-HXUWFJFHSA-N 0.000 claims 1
- NSTPEVOOVPYRJA-HXUWFJFHSA-N n-[(2r)-3-[2-ethyl-6-methyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OC[C@H](O)CNC(=O)CO)C(CC)=CC(C=2OC(=NN=2)C2=C(C(CC(C)C)=CS2)C)=C1 NSTPEVOOVPYRJA-HXUWFJFHSA-N 0.000 claims 1
- LQLUYMABVCWDQL-HXUWFJFHSA-N n-[(2r)-3-[2-ethyl-6-methyl-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OC[C@H](O)CNC(=O)CO)C(CC)=CC(C=2OC(=NN=2)C=2SC(C)=C(CC(C)C)C=2)=C1 LQLUYMABVCWDQL-HXUWFJFHSA-N 0.000 claims 1
- ZTSWVCLWOFEETE-JOCHJYFZSA-N n-[(2r)-3-[4-[3-[3,5-dimethyl-4-(2-methylpropyl)thiophen-2-yl]-3-oxopropyl]-2-ethyl-6-methylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OC[C@H](O)CNC(=O)CO)C(CC)=CC(CCC(=O)C2=C(C(CC(C)C)=C(C)S2)C)=C1 ZTSWVCLWOFEETE-JOCHJYFZSA-N 0.000 claims 1
- DCEINVNNEWFREB-HXUWFJFHSA-N n-[(2r)-3-[4-[5-[3,5-dimethyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]-2-ethyl-6-methylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OC[C@H](O)CNC(=O)CO)C(CC)=CC(C=2OC(=NN=2)C2=C(C(CC(C)C)=C(C)S2)C)=C1 DCEINVNNEWFREB-HXUWFJFHSA-N 0.000 claims 1
- JGDQODJFFAUBNE-NRFANRHFSA-N n-[(2s)-3-[2,6-diethyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CCC1=C(OC[C@@H](O)CNC(=O)CO)C(CC)=CC(C=2N=C(ON=2)C2=C(C(CC(C)C)=CS2)C)=C1 JGDQODJFFAUBNE-NRFANRHFSA-N 0.000 claims 1
- RQJFRUJPEPUBJT-NRFANRHFSA-N n-[(2s)-3-[2,6-diethyl-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CCC1=C(OC[C@@H](O)CNC(=O)CO)C(CC)=CC(C=2N=C(ON=2)C=2SC(C)=C(CC(C)C)C=2)=C1 RQJFRUJPEPUBJT-NRFANRHFSA-N 0.000 claims 1
- IUNDDHWOOJLJCV-KRWDZBQOSA-N n-[(2s)-3-[2-chloro-4-[5-[3,5-dimethyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]-6-methylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=C(C)SC(C=2ON=C(N=2)C=2C=C(Cl)C(OC[C@@H](O)CNC(=O)CO)=C(C)C=2)=C1C IUNDDHWOOJLJCV-KRWDZBQOSA-N 0.000 claims 1
- OUIIFEXFZFIDFR-KRWDZBQOSA-N n-[(2s)-3-[2-chloro-6-methyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=CSC(C=2ON=C(N=2)C=2C=C(Cl)C(OC[C@@H](O)CNC(=O)CO)=C(C)C=2)=C1C OUIIFEXFZFIDFR-KRWDZBQOSA-N 0.000 claims 1
- UULCTKWNLBKDEG-KRWDZBQOSA-N n-[(2s)-3-[2-chloro-6-methyl-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound S1C(C)=C(CC(C)C)C=C1C1=NC(C=2C=C(Cl)C(OC[C@@H](O)CNC(=O)CO)=C(C)C=2)=NO1 UULCTKWNLBKDEG-KRWDZBQOSA-N 0.000 claims 1
- USMRGOCLFZPFTE-FQEVSTJZSA-N n-[(2s)-3-[2-ethyl-6-methyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OC[C@@H](O)CNC(=O)CO)C(CC)=CC(C=2N=C(ON=2)C2=C(C(CC(C)C)=CS2)C)=C1 USMRGOCLFZPFTE-FQEVSTJZSA-N 0.000 claims 1
- NSTPEVOOVPYRJA-FQEVSTJZSA-N n-[(2s)-3-[2-ethyl-6-methyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OC[C@@H](O)CNC(=O)CO)C(CC)=CC(C=2OC(=NN=2)C2=C(C(CC(C)C)=CS2)C)=C1 NSTPEVOOVPYRJA-FQEVSTJZSA-N 0.000 claims 1
- LQLUYMABVCWDQL-FQEVSTJZSA-N n-[(2s)-3-[2-ethyl-6-methyl-4-[5-[5-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]phenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OC[C@@H](O)CNC(=O)CO)C(CC)=CC(C=2OC(=NN=2)C=2SC(C)=C(CC(C)C)C=2)=C1 LQLUYMABVCWDQL-FQEVSTJZSA-N 0.000 claims 1
- DCEINVNNEWFREB-FQEVSTJZSA-N n-[(2s)-3-[4-[5-[3,5-dimethyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]-2-ethyl-6-methylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC1=C(OC[C@@H](O)CNC(=O)CO)C(CC)=CC(C=2OC(=NN=2)C2=C(C(CC(C)C)=C(C)S2)C)=C1 DCEINVNNEWFREB-FQEVSTJZSA-N 0.000 claims 1
- WZOXUNBBCJSFKL-UHFFFAOYSA-N n-[3-[2,6-dimethyl-4-[5-[3-methyl-4-(2-methylpropyl)thiophen-2-yl]-1,2,4-oxadiazol-3-yl]phenoxy]-2-hydroxypropyl]-2-(methylamino)acetamide Chemical compound C1=C(C)C(OCC(O)CNC(=O)CNC)=C(C)C=C1C1=NOC(C2=C(C(CC(C)C)=CS2)C)=N1 WZOXUNBBCJSFKL-UHFFFAOYSA-N 0.000 claims 1
- OUCWPDPFPHZXES-UHFFFAOYSA-N n-[3-[4-[3-[3,4-bis(2-methylpropyl)thiophen-2-yl]-3-oxopropyl]-2,6-dimethylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=CSC(C(=O)CCC=2C=C(C)C(OCC(O)CNC(=O)CO)=C(C)C=2)=C1CC(C)C OUCWPDPFPHZXES-UHFFFAOYSA-N 0.000 claims 1
- NMKMMLLRTFHETQ-UHFFFAOYSA-N n-[3-[4-[5-[3,4-bis(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]-2,6-dimethylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=CSC(C=2OC(=NN=2)C=2C=C(C)C(OCC(O)CNC(=O)CO)=C(C)C=2)=C1CC(C)C NMKMMLLRTFHETQ-UHFFFAOYSA-N 0.000 claims 1
- YDRWMNJYXDDCSW-UHFFFAOYSA-N n-[3-[4-[5-[3-ethyl-4-(2-methylpropyl)thiophen-2-yl]-1,3,4-oxadiazol-2-yl]-2,6-dimethylphenoxy]-2-hydroxypropyl]-2-hydroxyacetamide Chemical compound CC(C)CC1=CSC(C=2OC(=NN=2)C=2C=C(C)C(OCC(O)CNC(=O)CO)=C(C)C=2)=C1CC YDRWMNJYXDDCSW-UHFFFAOYSA-N 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- VZBQJKIOAOUYJL-UHFFFAOYSA-N (1-methyl-1h-imidazol-2-yl)-(3-methyl-4-{3-[(pyridin-3-ylmethyl)-amino]-propoxy}-benzofuran-2-yl)-methanone Chemical compound C=12C(C)=C(C(=O)C=3N(C=CN=3)C)OC2=CC=CC=1OCCCNCC1=CC=CN=C1 VZBQJKIOAOUYJL-UHFFFAOYSA-N 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 239000003018 immunosuppressive agent Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- 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
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
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| US10035793B2 (en) | 2015-03-06 | 2018-07-31 | Asahi Glass Company, Limited | Method for producing 1,2,4-oxadiazole derivative |
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| US10111841B2 (en) | 2015-06-19 | 2018-10-30 | University Of South Florida | Stabilization of alcohol intoxication-induced cardiovascular instability |
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| CN119751336A (zh) | 2018-09-06 | 2025-04-04 | 艾尼纳制药公司 | 可用于治疗自身免疫性病症和炎性病症的化合物 |
| US11014897B1 (en) | 2018-10-16 | 2021-05-25 | Celgene Corporation | Solid forms comprising a thiazolidinone compound, compositions and methods of use thereof |
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- 2007-01-09 AR ARP070100083A patent/AR058956A1/es unknown
- 2007-01-10 MY MYPI20082557A patent/MY154909A/en unknown
- 2007-01-10 ES ES07700562T patent/ES2553345T3/es active Active
- 2007-01-10 US US12/160,520 patent/US8003800B2/en not_active Expired - Fee Related
- 2007-01-10 AU AU2007204121A patent/AU2007204121B2/en not_active Ceased
- 2007-01-10 BR BRPI0706476-4A patent/BRPI0706476A2/pt not_active IP Right Cessation
- 2007-01-10 WO PCT/IB2007/050070 patent/WO2007080542A1/en not_active Ceased
- 2007-01-10 KR KR1020087018081A patent/KR101382710B1/ko not_active Expired - Fee Related
- 2007-01-10 EP EP07700562.7A patent/EP1976512B1/en active Active
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- 2007-01-10 RU RU2008132802/04A patent/RU2437877C2/ru not_active IP Right Cessation
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- 2008-07-07 IL IL192657A patent/IL192657A/en not_active IP Right Cessation
- 2008-08-08 NO NO20083462A patent/NO20083462L/no not_active Application Discontinuation
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Also Published As
| Publication number | Publication date |
|---|---|
| AR058956A1 (es) | 2008-03-05 |
| CA2635047A1 (en) | 2007-07-19 |
| KR101382710B1 (ko) | 2014-04-08 |
| CA2635047C (en) | 2014-07-29 |
| NO20083462L (no) | 2008-10-09 |
| CN101370496A (zh) | 2009-02-18 |
| EP1976512B1 (en) | 2015-09-30 |
| NZ570258A (en) | 2011-07-29 |
| MY154909A (en) | 2015-08-28 |
| JP2009523165A (ja) | 2009-06-18 |
| TWI404706B (zh) | 2013-08-11 |
| RU2008132802A (ru) | 2010-02-20 |
| AU2007204121B2 (en) | 2012-06-07 |
| WO2007080542A1 (en) | 2007-07-19 |
| CN101370496B (zh) | 2012-07-04 |
| BRPI0706476A2 (pt) | 2011-04-05 |
| US8003800B2 (en) | 2011-08-23 |
| IL192657A (en) | 2015-09-24 |
| EP1976512A1 (en) | 2008-10-08 |
| KR20080083010A (ko) | 2008-09-12 |
| AU2007204121A1 (en) | 2007-07-19 |
| IL192657A0 (en) | 2009-02-11 |
| ES2553345T3 (es) | 2015-12-07 |
| US20100240717A1 (en) | 2010-09-23 |
| TW200804298A (en) | 2008-01-16 |
| JP5114430B2 (ja) | 2013-01-09 |
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