RU2010109455A - Производные 1,2-диамидоэтилена в качестве антагонистов орексина - Google Patents
Производные 1,2-диамидоэтилена в качестве антагонистов орексина Download PDFInfo
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- RU2010109455A RU2010109455A RU2010109455/04A RU2010109455A RU2010109455A RU 2010109455 A RU2010109455 A RU 2010109455A RU 2010109455/04 A RU2010109455/04 A RU 2010109455/04A RU 2010109455 A RU2010109455 A RU 2010109455A RU 2010109455 A RU2010109455 A RU 2010109455A
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- Prior art keywords
- carbonyl
- amino
- carboxylic acid
- ethyl
- methyl
- Prior art date
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- 102000002512 Orexin Human genes 0.000 title 1
- 239000005557 antagonist Substances 0.000 title 1
- 108060005714 orexin Proteins 0.000 title 1
- -1 bromo, cyclopropyl Chemical group 0.000 claims abstract 268
- 150000001875 compounds Chemical class 0.000 claims abstract 29
- 150000003839 salts Chemical class 0.000 claims abstract 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 12
- 239000001257 hydrogen Substances 0.000 claims abstract 12
- 125000001424 substituent group Chemical group 0.000 claims abstract 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract 11
- 150000002367 halogens Chemical class 0.000 claims abstract 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 11
- 125000003118 aryl group Chemical group 0.000 claims abstract 10
- 150000002431 hydrogen Chemical group 0.000 claims abstract 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 3
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 4
- VSQMBZXCDDTZAF-UHFFFAOYSA-N 6-methylimidazo[2,1-b][1,3]thiazole-5-carboxylic acid Chemical compound S1C=CN2C(C(O)=O)=C(C)N=C21 VSQMBZXCDDTZAF-UHFFFAOYSA-N 0.000 claims 3
- HMVYYTRDXNKRBQ-UHFFFAOYSA-N 1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC=N1 HMVYYTRDXNKRBQ-UHFFFAOYSA-N 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- 208000025966 Neurological disease Diseases 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 230000035622 drinking Effects 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 229940001470 psychoactive drug Drugs 0.000 claims 2
- 239000004089 psychotropic agent Substances 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 238000011282 treatment Methods 0.000 claims 2
- 125000004565 2,3-dihydrobenzofuran-4-yl group Chemical group O1CCC2=C1C=CC=C2* 0.000 claims 1
- DTXHGXYFPXKGSL-UHFFFAOYSA-N 2-amino-5-(3-chlorophenyl)-1,3-thiazole-4-carboxylic acid Chemical compound S1C(N)=NC(C(O)=O)=C1C1=CC=CC(Cl)=C1 DTXHGXYFPXKGSL-UHFFFAOYSA-N 0.000 claims 1
- CSEWYJMWIQZIJJ-UHFFFAOYSA-N 2-amino-n-cyclopropyl-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(N)=NC=1C(=O)N(CCNC(=O)C=1C=2OCCOC=2C=CC=1)C1CC1 CSEWYJMWIQZIJJ-UHFFFAOYSA-N 0.000 claims 1
- ARWWRJHTXVCJPY-UHFFFAOYSA-N 2-cyclopropyl-n-(cyclopropylmethyl)-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-5-(3-methoxyphenyl)-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(S2)C2CC2)C(=O)N(CCNC(=O)C=2C=3OCCOC=3C=CC=2)CC2CC2)=C1 ARWWRJHTXVCJPY-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- DLNAGSPCJPDFRS-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-cyclopropyl-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2OCCOC=2C=CC=1)C1CC1 DLNAGSPCJPDFRS-UHFFFAOYSA-N 0.000 claims 1
- UJMIGFGAFXZFKU-UHFFFAOYSA-N 6-methylimidazo[2,1-b][1,3]thiazole-5-carboxamide Chemical compound S1C=CN2C(C(N)=O)=C(C)N=C21 UJMIGFGAFXZFKU-UHFFFAOYSA-N 0.000 claims 1
- VCUCXOAGBHLXPB-UHFFFAOYSA-N CC1=NC(C(O)=O)=C(C2=CC(C(F)(F)F)=CC=C2)S1.O=C(C1=CC=CC2=C1OCCO2)NCCNCC1CC1 Chemical compound CC1=NC(C(O)=O)=C(C2=CC(C(F)(F)F)=CC=C2)S1.O=C(C1=CC=CC2=C1OCCO2)NCCNCC1CC1 VCUCXOAGBHLXPB-UHFFFAOYSA-N 0.000 claims 1
- SNYVJHGZTHFIPT-UHFFFAOYSA-N COC1=CC=CC(C(S2)=C(C(O)=O)N=C2Br)=C1.O=C(C1=CC=CC2=C1OCCO2)NCCNCC1CC1 Chemical compound COC1=CC=CC(C(S2)=C(C(O)=O)N=C2Br)=C1.O=C(C1=CC=CC2=C1OCCO2)NCCNCC1CC1 SNYVJHGZTHFIPT-UHFFFAOYSA-N 0.000 claims 1
- JTLKRCUKQZNOLN-UHFFFAOYSA-N COC1=CC=CC(C2=C(C(O)=O)N=C(N)S2)=C1.O=C(C1=CC=CC2=C1OCCO2)NCCNCC1CC1 Chemical compound COC1=CC=CC(C2=C(C(O)=O)N=C(N)S2)=C1.O=C(C1=CC=CC2=C1OCCO2)NCCNCC1CC1 JTLKRCUKQZNOLN-UHFFFAOYSA-N 0.000 claims 1
- FDRPXJYBJSEVLB-UHFFFAOYSA-N N-[2-(cyclopropylamino)ethyl]-1-benzofuran-4-carboxamide Chemical compound C=1C=CC=2OC=CC=2C=1C(=O)NCCNC1CC1 FDRPXJYBJSEVLB-UHFFFAOYSA-N 0.000 claims 1
- JWRKIQPISSTIRN-UHFFFAOYSA-N N-[2-(cyclopropylmethylamino)ethyl]-1-benzofuran-4-carboxamide Chemical compound C=1C=CC=2OC=CC=2C=1C(=O)NCCNCC1CC1 JWRKIQPISSTIRN-UHFFFAOYSA-N 0.000 claims 1
- YKRWQKPONMRVTG-UHFFFAOYSA-N N-[2-(methylamino)propyl]-1-benzofuran-4-carboxamide Chemical compound CNC(C)CNC(=O)C1=CC=CC2=C1C=CO2 YKRWQKPONMRVTG-UHFFFAOYSA-N 0.000 claims 1
- OCGJYVIFSNXQBI-UHFFFAOYSA-N NC1=NC(C(O)=O)=C(C2=CC(F)=CC=C2)S1.O=C(C1=CC=CC2=C1OCCO2)NCCNCC1CC1 Chemical compound NC1=NC(C(O)=O)=C(C2=CC(F)=CC=C2)S1.O=C(C1=CC=CC2=C1OCCO2)NCCNCC1CC1 OCGJYVIFSNXQBI-UHFFFAOYSA-N 0.000 claims 1
- HWSDQCXRGVWLBE-UHFFFAOYSA-N OC(=O)C=1N=C(C2CC2)SC=1C1=CC=CC=C1.C=1C=CC=2OCCOC=2C=1C(=O)NCCNCC1CC1 Chemical compound OC(=O)C=1N=C(C2CC2)SC=1C1=CC=CC=C1.C=1C=CC=2OCCOC=2C=1C(=O)NCCNCC1CC1 HWSDQCXRGVWLBE-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004245 indazol-3-yl group Chemical group [H]N1N=C(*)C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
- 125000004254 isoquinolin-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C2C(*)=N1 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- BFGBDNZFQITTNB-UHFFFAOYSA-N n,2-dicyclopropyl-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-5-(3-methoxyphenyl)-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(S2)C2CC2)C(=O)N(CCNC(=O)C=2C=3OCCOC=3C=CC=2)C2CC2)=C1 BFGBDNZFQITTNB-UHFFFAOYSA-N 0.000 claims 1
- FUNMRDFBHDMWPV-UHFFFAOYSA-N n,2-dicyclopropyl-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-5-(3-methylphenyl)-1,3-thiazole-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(S2)C2CC2)C(=O)N(CCNC(=O)C=2C=3OCCOC=3C=CC=2)C2CC2)=C1 FUNMRDFBHDMWPV-UHFFFAOYSA-N 0.000 claims 1
- HTKSRXGRZWLSIH-UHFFFAOYSA-N n,2-dicyclopropyl-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=2OCCOC=2C=1C(=O)NCCN(C(=O)C1=C(SC(=N1)C1CC1)C=1C=CC=CC=1)C1CC1 HTKSRXGRZWLSIH-UHFFFAOYSA-N 0.000 claims 1
- ZULYRSVGHJKXEP-UHFFFAOYSA-N n-(cyclopropylmethyl)-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-5-(3,4-dimethylphenyl)-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=C(C)C(C)=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2OCCOC=2C=CC=1)CC1CC1 ZULYRSVGHJKXEP-UHFFFAOYSA-N 0.000 claims 1
- ZVLBPKWMTJCQHY-UHFFFAOYSA-N n-(cyclopropylmethyl)-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-5-(3-fluorophenyl)-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC(F)=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2OCCOC=2C=CC=1)CC1CC1 ZVLBPKWMTJCQHY-UHFFFAOYSA-N 0.000 claims 1
- WSNKRFQSACKASX-UHFFFAOYSA-N n-(cyclopropylmethyl)-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-5-(3-methoxyphenyl)-2-methyl-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(C)S2)C(=O)N(CCNC(=O)C=2C=3OCCOC=3C=CC=2)CC2CC2)=C1 WSNKRFQSACKASX-UHFFFAOYSA-N 0.000 claims 1
- XXDTXKBYGODIEM-UHFFFAOYSA-N n-[1-(1-benzofuran-4-carbonylamino)-3-methylbutan-2-yl]-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=2OC=CC=2C=1C(=O)NCC(C(C)C)NC(=O)C=1N=C(C)SC=1C1=CC=CC=C1 XXDTXKBYGODIEM-UHFFFAOYSA-N 0.000 claims 1
- MWKQRFXZZPLKAU-UHFFFAOYSA-N n-[1-(1-benzofuran-4-carbonylamino)-3-phenylpropan-2-yl]-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)NC(CNC(=O)C=1C=2C=COC=2C=CC=1)CC1=CC=CC=C1 MWKQRFXZZPLKAU-UHFFFAOYSA-N 0.000 claims 1
- QARPMDZQRPJBEC-UHFFFAOYSA-N n-[1-(1-benzofuran-4-carbonylamino)-4-methylpentan-2-yl]-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=2OC=CC=2C=1C(=O)NCC(CC(C)C)NC(=O)C=1N=C(C)SC=1C1=CC=CC=C1 QARPMDZQRPJBEC-UHFFFAOYSA-N 0.000 claims 1
- KVUKIKWBGPQYEU-UHFFFAOYSA-N n-[1-(1-benzofuran-4-carbonylamino)-4-phenylbutan-2-yl]-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)NC(CNC(=O)C=1C=2C=COC=2C=CC=1)CCC1=CC=CC=C1 KVUKIKWBGPQYEU-UHFFFAOYSA-N 0.000 claims 1
- DPYQTKLUMRYXAH-UHFFFAOYSA-N n-[1-(1-benzofuran-4-carbonylamino)propan-2-yl]-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=2OC=CC=2C=1C(=O)NCC(C)NC(=O)C=1N=C(C)SC=1C1=CC=CC=C1 DPYQTKLUMRYXAH-UHFFFAOYSA-N 0.000 claims 1
- CMIJOZZEYALWLU-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)-1-cyclopropylethyl]-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)NC(CNC(=O)C=1C=2C=COC=2C=CC=1)C1CC1 CMIJOZZEYALWLU-UHFFFAOYSA-N 0.000 claims 1
- VEERWIQYZQSXKM-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-2-methyl-5-phenyl-n-(3-phenylpropyl)-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CCCC1=CC=CC=C1 VEERWIQYZQSXKM-UHFFFAOYSA-N 0.000 claims 1
- LIWSOLYYTOKZNY-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-2-methyl-5-phenyl-n-[[4-(trifluoromethyl)phenyl]methyl]-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CC1=CC=C(C(F)(F)F)C=C1 LIWSOLYYTOKZNY-UHFFFAOYSA-N 0.000 claims 1
- RAJRGIUOYNWFOA-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-(3,3-dimethylbutyl)-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound S1C(C)=NC(C(=O)N(CCNC(=O)C=2C=3C=COC=3C=CC=2)CCC(C)(C)C)=C1C1=CC=CC=C1 RAJRGIUOYNWFOA-UHFFFAOYSA-N 0.000 claims 1
- CIYYQKOMGUQNOO-UHFFFAOYSA-N n-[2-(1-benzofuran-4-carbonylamino)ethyl]-n-[(4-fluorophenyl)methyl]-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2C=COC=2C=CC=1)CC1=CC=C(F)C=C1 CIYYQKOMGUQNOO-UHFFFAOYSA-N 0.000 claims 1
- IXWPDBHGEQPSFL-UHFFFAOYSA-N n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-2-methyl-5-phenyl-n-[[4-(trifluoromethyl)phenyl]methyl]-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2OCCOC=2C=CC=1)CC1=CC=C(C(F)(F)F)C=C1 IXWPDBHGEQPSFL-UHFFFAOYSA-N 0.000 claims 1
- QNVHVWLPZXUBHM-UHFFFAOYSA-N n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-n-(3,3-dimethylbutyl)-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound S1C(C)=NC(C(=O)N(CCNC(=O)C=2C=3OCCOC=3C=CC=2)CCC(C)(C)C)=C1C1=CC=CC=C1 QNVHVWLPZXUBHM-UHFFFAOYSA-N 0.000 claims 1
- KRQYNEARPNJSMY-UHFFFAOYSA-N n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-n-[(4-fluorophenyl)methyl]-2-methyl-5-phenyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2OCCOC=2C=CC=1)CC1=CC=C(F)C=C1 KRQYNEARPNJSMY-UHFFFAOYSA-N 0.000 claims 1
- KNBOJLAYSNCYRZ-UHFFFAOYSA-N n-[2-[cyclopropylmethyl-[2-(4-fluorophenyl)benzoyl]amino]ethyl]-1-benzofuran-4-carboxamide Chemical compound C1=CC(F)=CC=C1C1=CC=CC=C1C(=O)N(CC1CC1)CCNC(=O)C1=CC=CC2=C1C=CO2 KNBOJLAYSNCYRZ-UHFFFAOYSA-N 0.000 claims 1
- MPVRZAJOFYQSAR-UHFFFAOYSA-N n-benzyl-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-5-(4-fluorophenyl)-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=C(F)C=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2OCCOC=2C=CC=1)CC1=CC=CC=C1 MPVRZAJOFYQSAR-UHFFFAOYSA-N 0.000 claims 1
- JQGMAXJWXAJBLK-UHFFFAOYSA-N n-benzyl-n-[2-(2,3-dihydro-1-benzofuran-7-carbonylamino)ethyl]-5-(4-fluorophenyl)-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=C(F)C=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2OCCC=2C=CC=1)CC1=CC=CC=C1 JQGMAXJWXAJBLK-UHFFFAOYSA-N 0.000 claims 1
- YBERNQFNYUIMIO-UHFFFAOYSA-N n-cyclopropyl-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-5-(3,4-dimethylphenyl)-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=C(C)C(C)=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2OCCOC=2C=CC=1)C1CC1 YBERNQFNYUIMIO-UHFFFAOYSA-N 0.000 claims 1
- PNIHOHPZFKJAFN-UHFFFAOYSA-N n-cyclopropyl-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-5-(3-fluorophenyl)-2-methyl-1,3-thiazole-4-carboxamide Chemical compound C=1C=CC(F)=CC=1C=1SC(C)=NC=1C(=O)N(CCNC(=O)C=1C=2OCCOC=2C=CC=1)C1CC1 PNIHOHPZFKJAFN-UHFFFAOYSA-N 0.000 claims 1
- FEDNFMQZEDJWGC-UHFFFAOYSA-N n-cyclopropyl-n-[2-(2,3-dihydro-1,4-benzodioxine-5-carbonylamino)ethyl]-5-(3-methoxyphenyl)-2-methyl-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=CC(C2=C(N=C(C)S2)C(=O)N(CCNC(=O)C=2C=3OCCOC=3C=CC=2)C2CC2)=C1 FEDNFMQZEDJWGC-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 208000020685 sleep-wake disease Diseases 0.000 claims 1
- 239000010802 sludge Substances 0.000 claims 1
- GGNIKGLUPSHSBV-UHFFFAOYSA-N thiazole-5-carboxamide Chemical compound NC(=O)C1=CN=CS1 GGNIKGLUPSHSBV-UHFFFAOYSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 0 *C(CNC(*)=O)N(*)C(*)=O Chemical compound *C(CNC(*)=O)N(*)C(*)=O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
-
- 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
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
-
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| KR101859409B1 (ko) | 2009-10-23 | 2018-05-18 | 얀센 파마슈티카 엔.브이. | 오렉신 수용체 조절제로서의 이치환된 옥타하이드로피롤로［3,4-ｃ］피롤 |
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| US9440982B2 (en) | 2012-02-07 | 2016-09-13 | Eolas Therapeutics, Inc. | Substituted prolines/piperidines as orexin receptor antagonists |
| NZ628491A (en) | 2012-02-07 | 2016-06-24 | Eolas Therapeutics Inc | Substituted prolines / piperidines as orexin receptor antagonists |
| AR098436A1 (es) * | 2013-11-19 | 2016-05-26 | Actelion Pharmaceuticals Ltd | Compuestos tricíclicos de piperidina |
| JP6663909B2 (ja) | 2014-08-13 | 2020-03-13 | エオラス セラピューティクス， インコーポレイテッド | オレキシンレセプターモジュレーターとしてのジフルオロピロリジン |
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| SI3414241T1 (sl) | 2016-02-12 | 2022-10-28 | Astrazeneca Ab | Halo-substituitani piperidini kot modulatorji receptorja oreksina |
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| EP2188282B1 (en) | 2013-01-23 |
| KR20100055464A (ko) | 2010-05-26 |
| CN101778846A (zh) | 2010-07-14 |
| CA2694993A1 (en) | 2009-02-19 |
| WO2009022311A2 (en) | 2009-02-19 |
| BRPI0815079A2 (pt) | 2015-02-03 |
| ES2400830T3 (es) | 2013-04-12 |
| MX2010001575A (es) | 2010-03-15 |
| JP2010536740A (ja) | 2010-12-02 |
| AU2008288151A1 (en) | 2009-02-19 |
| EP2188282A2 (en) | 2010-05-26 |
| WO2009022311A3 (en) | 2009-04-09 |
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