RU2460732C2 - Производные 2-аза-бицикло[3.1.0.]гексана в качестве антагонистов рецептора орексина - Google Patents
Производные 2-аза-бицикло[3.1.0.]гексана в качестве антагонистов рецептора орексина Download PDFInfo
- Publication number
- RU2460732C2 RU2460732C2 RU2009128739/04A RU2009128739A RU2460732C2 RU 2460732 C2 RU2460732 C2 RU 2460732C2 RU 2009128739/04 A RU2009128739/04 A RU 2009128739/04A RU 2009128739 A RU2009128739 A RU 2009128739A RU 2460732 C2 RU2460732 C2 RU 2460732C2
- Authority
- RU
- Russia
- Prior art keywords
- hex
- aza
- bicyclo
- ylmethyl
- carbonyl
- Prior art date
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- WSSDGZWSPMAECX-UHFFFAOYSA-N 2-azabicyclo[3.1.0]hexane Chemical class C1CNC2CC21 WSSDGZWSPMAECX-UHFFFAOYSA-N 0.000 title claims abstract 3
- 229940123730 Orexin receptor antagonist Drugs 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract 24
- 150000003839 salts Chemical class 0.000 claims abstract 10
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims abstract 2
- 206010022437 insomnia Diseases 0.000 claims abstract 2
- -1 2,3-dihydrobenzofuranyl Chemical group 0.000 claims 47
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000001424 substituent group Chemical group 0.000 claims 13
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 150000001408 amides Chemical class 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 5
- BURBCLDNKTXYCU-ILXRZTDVSA-N [(1s,3s,5s)-3-(aminomethyl)-2-azabicyclo[3.1.0]hexan-2-yl]-[2-methyl-5-(3-methylphenyl)-1,3-thiazol-4-yl]methanone Chemical compound S1C(C)=NC(C(=O)N2[C@@H](C[C@@H]3C[C@@H]32)CN)=C1C1=CC=CC(C)=C1 BURBCLDNKTXYCU-ILXRZTDVSA-N 0.000 claims 5
- KMAKOBLIOCQGJP-UHFFFAOYSA-N indole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CNC2=C1 KMAKOBLIOCQGJP-UHFFFAOYSA-N 0.000 claims 5
- BHXVYTQDWMQVBI-UHFFFAOYSA-N 1h-indazole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=NNC2=C1 BHXVYTQDWMQVBI-UHFFFAOYSA-N 0.000 claims 4
- UXYRXGFUANQKTA-UHFFFAOYSA-N 1,2-oxazole-3-carboxylic acid Chemical compound OC(=O)C=1C=CON=1 UXYRXGFUANQKTA-UHFFFAOYSA-N 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- GLZXZPAHANTQJE-USWWRNFRSA-N [2-amino-5-(3-fluorophenyl)-1,3-thiazol-4-yl]-[(1s,3s,5s)-3-(aminomethyl)-2-azabicyclo[3.1.0]hexan-2-yl]methanone Chemical compound N1([C@H]2C[C@H]2C[C@H]1CN)C(=O)C=1N=C(N)SC=1C1=CC=CC(F)=C1 GLZXZPAHANTQJE-USWWRNFRSA-N 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 229910052717 sulfur Chemical group 0.000 claims 3
- 239000011593 sulfur Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- PXUXUJPEQCJYIM-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazine-5-carboxylic acid Chemical compound O1CCNC2=C1C=CC=C2C(=O)O PXUXUJPEQCJYIM-UHFFFAOYSA-N 0.000 claims 2
- HWBALMSPYAUMMB-UHFFFAOYSA-N 6-fluoro-4h-1,3-benzodioxine-8-carboxylic acid Chemical compound C1OCOC2=C1C=C(F)C=C2C(=O)O HWBALMSPYAUMMB-UHFFFAOYSA-N 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- CYCAKXWCBTXQHL-HOJAQTOUSA-N C(C1=CC=CC=C1)(=O)NC[C@H]1N([C@H]2C[C@H]2C1)C(=O)C=1N=C(SC1C1=CC(=CC=C1)F)C Chemical compound C(C1=CC=CC=C1)(=O)NC[C@H]1N([C@H]2C[C@H]2C1)C(=O)C=1N=C(SC1C1=CC(=CC=C1)F)C CYCAKXWCBTXQHL-HOJAQTOUSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- MUFAPVOEYKGQMC-VBHSOAQHSA-N [(1S,3S,5S)-3-(aminomethyl)-2-azabicyclo[3.1.0]hexan-2-yl]-[2-(2-fluorophenyl)phenyl]methanone Chemical compound N1([C@H]2C[C@H]2C[C@H]1CN)C(=O)C1=CC=CC=C1C1=CC=CC=C1F MUFAPVOEYKGQMC-VBHSOAQHSA-N 0.000 claims 2
- MDBYOYRKNWHOFL-XUWXXGDYSA-N [(1S,3S,5S)-3-(aminomethyl)-2-azabicyclo[3.1.0]hexan-2-yl]-[2-(3-chlorophenyl)phenyl]methanone Chemical compound N1([C@H]2C[C@H]2C[C@H]1CN)C(=O)C1=CC=CC=C1C1=CC=CC(Cl)=C1 MDBYOYRKNWHOFL-XUWXXGDYSA-N 0.000 claims 2
- DSNCWJUOJMOACG-XBFCOCLRSA-N [(1S,3S,5S)-3-(aminomethyl)-2-azabicyclo[3.1.0]hexan-2-yl]-[5-(3-chlorophenyl)-2-methyl-1,3-thiazol-4-yl]methanone Chemical compound S1C(C)=NC(C(=O)N2[C@@H](C[C@@H]3C[C@@H]32)CN)=C1C1=CC=CC(Cl)=C1 DSNCWJUOJMOACG-XBFCOCLRSA-N 0.000 claims 2
- NESUJRTUYRQKLV-XBFCOCLRSA-N [(1s,3s,5s)-3-(aminomethyl)-2-azabicyclo[3.1.0]hexan-2-yl]-[5-(3-fluorophenyl)-2-methyl-1,3-thiazol-4-yl]methanone Chemical compound S1C(C)=NC(C(=O)N2[C@@H](C[C@@H]3C[C@@H]32)CN)=C1C1=CC=CC(F)=C1 NESUJRTUYRQKLV-XBFCOCLRSA-N 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- LXOHISCRPIDIIG-UHFFFAOYSA-N 1,4-dioxine-2-carboxylic acid Chemical compound OC(=O)C1=COC=CO1 LXOHISCRPIDIIG-UHFFFAOYSA-N 0.000 claims 1
- ZGAQVJDFFVTWJK-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1OC(F)(F)O2 ZGAQVJDFFVTWJK-UHFFFAOYSA-N 0.000 claims 1
- CHDSHBWEGSCEDX-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1CCO2 CHDSHBWEGSCEDX-UHFFFAOYSA-N 0.000 claims 1
- VFMGOJUUTAPPDA-UHFFFAOYSA-N 2-ethyl-5-methylpyrazole-3-carboxylic acid Chemical compound CCN1N=C(C)C=C1C(O)=O VFMGOJUUTAPPDA-UHFFFAOYSA-N 0.000 claims 1
- QMVZMKJWEQFJDP-UHFFFAOYSA-N 2h-chromene-5-carboxylic acid Chemical compound O1CC=CC2=C1C=CC=C2C(=O)O QMVZMKJWEQFJDP-UHFFFAOYSA-N 0.000 claims 1
- KZGWWOCYVZVDPN-UHFFFAOYSA-N 3,4-dihydro-2h-chromene-5-carboxamide Chemical compound O1CCCC2=C1C=CC=C2C(=O)N KZGWWOCYVZVDPN-UHFFFAOYSA-N 0.000 claims 1
- AZAHJSDNHZYCDQ-DXIQSLLYSA-N 3-chloro-2-methyl-n-[[(1s,3s,5s)-2-[2-methyl-5-(3-methylphenyl)-1,3-thiazole-4-carbonyl]-2-azabicyclo[3.1.0]hexan-3-yl]methyl]benzamide Chemical compound C([C@@H]1C[C@@H]2C[C@@H]2N1C(=O)C=1N=C(SC=1C=1C=C(C)C=CC=1)C)NC(=O)C1=CC=CC(Cl)=C1C AZAHJSDNHZYCDQ-DXIQSLLYSA-N 0.000 claims 1
- YARITCNZSWTFLI-NJAFHUGGSA-N 4-amino-2-[[(1s,3s,5s)-2-[2-methyl-5-(3-methylphenyl)-1,3-thiazole-4-carbonyl]-2-azabicyclo[3.1.0]hexan-3-yl]methylamino]pyrimidine-5-carbonitrile Chemical compound C([C@@H]1C[C@@H]2C[C@@H]2N1C(=O)C=1N=C(SC=1C=1C=C(C)C=CC=1)C)NC1=NC=C(C#N)C(N)=N1 YARITCNZSWTFLI-NJAFHUGGSA-N 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- JKEUXKJMBNQDRK-LMNJBCLMSA-N 4-chloro-2-methoxy-n-[[(1s,3s,5s)-2-[2-methyl-5-(3-methylphenyl)-1,3-thiazole-4-carbonyl]-2-azabicyclo[3.1.0]hexan-3-yl]methyl]benzamide Chemical compound COC1=CC(Cl)=CC=C1C(=O)NC[C@H]1N(C(=O)C2=C(SC(C)=N2)C=2C=C(C)C=CC=2)[C@H]2C[C@H]2C1 JKEUXKJMBNQDRK-LMNJBCLMSA-N 0.000 claims 1
- DFLOUBRTXQQGOE-DYXWJJEUSA-N 4-methoxy-n-[[(1s,3s,5s)-2-[2-methyl-5-(3-methylphenyl)-1,3-thiazole-4-carbonyl]-2-azabicyclo[3.1.0]hexan-3-yl]methyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1C(=O)NC[C@H]1N(C(=O)C2=C(SC(C)=N2)C=2C=C(C)C=CC=2)[C@H]2C[C@H]2C1 DFLOUBRTXQQGOE-DYXWJJEUSA-N 0.000 claims 1
- ZOPXUHDPGGHISS-UHFFFAOYSA-N 5-fluoro-1-methylindole-2-carboxylic acid Chemical compound FC1=CC=C2N(C)C(C(O)=O)=CC2=C1 ZOPXUHDPGGHISS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- TXVCJVXGOCKWEN-NJAFHUGGSA-N C(C1=CC=CC=C1)(=O)NC[C@H]1N([C@H]2C[C@H]2C1)C(=O)C=1N=C(SC1C1=CC(=CC=C1)F)N Chemical compound C(C1=CC=CC=C1)(=O)NC[C@H]1N([C@H]2C[C@H]2C1)C(=O)C=1N=C(SC1C1=CC(=CC=C1)F)N TXVCJVXGOCKWEN-NJAFHUGGSA-N 0.000 claims 1
- ARFYZTJVUUOMON-MNRZFKEHSA-N CC(C)(C)C1=NN(C)C(C(O)=O)=C1.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O Chemical compound CC(C)(C)C1=NN(C)C(C(O)=O)=C1.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O ARFYZTJVUUOMON-MNRZFKEHSA-N 0.000 claims 1
- LQALEHSGOMKQSR-OQNHHKPVSA-N CC(C)(C1)OC2=C1C=CC=C2C(O)=O.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1 Chemical compound CC(C)(C1)OC2=C1C=CC=C2C(O)=O.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1 LQALEHSGOMKQSR-OQNHHKPVSA-N 0.000 claims 1
- OYDPLKAWVNTYQT-DSMRVHDJSA-N CC(C)(C1)OC2=C1C=CC=C2C(O)=O.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1 Chemical compound CC(C)(C1)OC2=C1C=CC=C2C(O)=O.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1 OYDPLKAWVNTYQT-DSMRVHDJSA-N 0.000 claims 1
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- OCPFLHDEAUPJKB-SQNIBIBYSA-N [(1s,3s,5s)-3-[[(4,6-dimethoxypyrimidin-2-yl)amino]methyl]-2-azabicyclo[3.1.0]hexan-2-yl]-[2-methyl-5-(3-methylphenyl)-1,3-thiazol-4-yl]methanone Chemical compound COC1=CC(OC)=NC(NC[C@H]2N([C@H]3C[C@H]3C2)C(=O)C2=C(SC(C)=N2)C=2C=C(C)C=CC=2)=N1 OCPFLHDEAUPJKB-SQNIBIBYSA-N 0.000 claims 1
- MVPBEYORUDQRHJ-NJAFHUGGSA-N [(1s,3s,5s)-3-[[(5-bromopyrimidin-2-yl)amino]methyl]-2-azabicyclo[3.1.0]hexan-2-yl]-(2-cyclopropyl-5-phenyl-1,3-thiazol-4-yl)methanone Chemical compound N1=CC(Br)=CN=C1NC[C@H]1N(C(=O)C2=C(SC(=N2)C2CC2)C=2C=CC=CC=2)[C@H]2C[C@H]2C1 MVPBEYORUDQRHJ-NJAFHUGGSA-N 0.000 claims 1
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- JJYPMUVMTCCHFA-NJAFHUGGSA-N [(1s,3s,5s)-3-[[(5-bromopyrimidin-2-yl)amino]methyl]-2-azabicyclo[3.1.0]hexan-2-yl]-[2-methyl-5-(3-methylphenyl)-1,3-thiazol-4-yl]methanone Chemical compound C([C@@H]1C[C@@H]2C[C@@H]2N1C(=O)C=1N=C(SC=1C=1C=C(C)C=CC=1)C)NC1=NC=C(Br)C=N1 JJYPMUVMTCCHFA-NJAFHUGGSA-N 0.000 claims 1
- WSLKOLMTAAYPMR-COXVUDFISA-N [(1s,3s,5s)-3-[[(5-bromopyrimidin-2-yl)amino]methyl]-2-azabicyclo[3.1.0]hexan-2-yl]-[2-methyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methanone Chemical compound C([C@@H]1C[C@@H]2C[C@@H]2N1C(=O)C=1N=C(SC=1C=1C=C(C=CC=1)C(F)(F)F)C)NC1=NC=C(Br)C=N1 WSLKOLMTAAYPMR-COXVUDFISA-N 0.000 claims 1
- UTIODKKMBCLUHW-IFIJOSMWSA-N [(1s,3s,5s)-3-[[(5-bromopyrimidin-2-yl)amino]methyl]-2-azabicyclo[3.1.0]hexan-2-yl]-[5-(3,4-dichlorophenyl)-2-methyl-1,3-thiazol-4-yl]methanone Chemical compound C([C@@H]1C[C@@H]2C[C@@H]2N1C(=O)C=1N=C(SC=1C=1C=C(Cl)C(Cl)=CC=1)C)NC1=NC=C(Br)C=N1 UTIODKKMBCLUHW-IFIJOSMWSA-N 0.000 claims 1
- BEXLHINYFZDODT-IFIJOSMWSA-N [(1s,3s,5s)-3-[[(5-bromopyrimidin-2-yl)amino]methyl]-2-azabicyclo[3.1.0]hexan-2-yl]-[5-(3,4-difluorophenyl)-2-methyl-1,3-thiazol-4-yl]methanone Chemical compound C([C@@H]1C[C@@H]2C[C@@H]2N1C(=O)C=1N=C(SC=1C=1C=C(F)C(F)=CC=1)C)NC1=NC=C(Br)C=N1 BEXLHINYFZDODT-IFIJOSMWSA-N 0.000 claims 1
- ZWCXIYNPZUPTJW-NEWSRXKRSA-N [(1s,3s,5s)-3-[[(5-bromopyrimidin-2-yl)amino]methyl]-2-azabicyclo[3.1.0]hexan-2-yl]-[5-(3,4-dimethylphenyl)-2-methyl-1,3-thiazol-4-yl]methanone Chemical compound C([C@@H]1C[C@@H]2C[C@@H]2N1C(=O)C=1N=C(SC=1C=1C=C(C)C(C)=CC=1)C)NC1=NC=C(Br)C=N1 ZWCXIYNPZUPTJW-NEWSRXKRSA-N 0.000 claims 1
- BVRLEKPFIWDGBN-KCXAZCMYSA-N [(1s,3s,5s)-3-[[(5-bromopyrimidin-2-yl)amino]methyl]-2-azabicyclo[3.1.0]hexan-2-yl]-[5-(3-chlorophenyl)-1,3-thiazol-4-yl]methanone Chemical compound ClC1=CC=CC(C2=C(N=CS2)C(=O)N2[C@@H](C[C@@H]3C[C@@H]32)CNC=2N=CC(Br)=CN=2)=C1 BVRLEKPFIWDGBN-KCXAZCMYSA-N 0.000 claims 1
- NODAGFGTEXFBBV-COXVUDFISA-N [(1s,3s,5s)-3-[[(5-bromopyrimidin-2-yl)amino]methyl]-2-azabicyclo[3.1.0]hexan-2-yl]-[5-(3-chlorophenyl)-2-methyl-1,3-thiazol-4-yl]methanone Chemical compound C([C@@H]1C[C@@H]2C[C@@H]2N1C(=O)C=1N=C(SC=1C=1C=C(Cl)C=CC=1)C)NC1=NC=C(Br)C=N1 NODAGFGTEXFBBV-COXVUDFISA-N 0.000 claims 1
- ULTVXVJJYMVKKB-HFTRVMKXSA-N [(1s,3s,5s)-3-[[(5-bromopyrimidin-2-yl)amino]methyl]-2-azabicyclo[3.1.0]hexan-2-yl]-[5-(3-fluoro-4-methylphenyl)-2-methyl-1,3-thiazol-4-yl]methanone Chemical compound C([C@@H]1C[C@@H]2C[C@@H]2N1C(=O)C=1N=C(SC=1C=1C=C(F)C(C)=CC=1)C)NC1=NC=C(Br)C=N1 ULTVXVJJYMVKKB-HFTRVMKXSA-N 0.000 claims 1
- IHCDQMGOFLPHAI-KMFMINBZSA-N [(1s,3s,5s)-3-[[(5-bromopyrimidin-2-yl)amino]methyl]-2-azabicyclo[3.1.0]hexan-2-yl]-[5-(3-methoxyphenyl)-1,3-thiazol-4-yl]methanone Chemical compound COC1=CC=CC(C2=C(N=CS2)C(=O)N2[C@@H](C[C@@H]3C[C@@H]32)CNC=2N=CC(Br)=CN=2)=C1 IHCDQMGOFLPHAI-KMFMINBZSA-N 0.000 claims 1
- VIRNIFNUAHJGFC-AABGKKOBSA-N [(1s,3s,5s)-3-[[(5-ethylpyrimidin-2-yl)amino]methyl]-2-azabicyclo[3.1.0]hexan-2-yl]-[2-methyl-5-(3-methylphenyl)-1,3-thiazol-4-yl]methanone Chemical compound N1=CC(CC)=CN=C1NC[C@H]1N(C(=O)C2=C(SC(C)=N2)C=2C=C(C)C=CC=2)[C@H]2C[C@H]2C1 VIRNIFNUAHJGFC-AABGKKOBSA-N 0.000 claims 1
- JECNMUNOLVPOMN-MNRZFKEHSA-N [2-amino-5-(3-fluorophenyl)-1,3-thiazol-4-yl]-[(1S,3S,5S)-3-(aminomethyl)-2-azabicyclo[3.1.0]hexan-2-yl]methanone 2,2-difluoro-1,3-benzodioxole-4-carboxylic acid Chemical compound NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O.OC(C1=CC=CC(O2)=C1OC2(F)F)=O JECNMUNOLVPOMN-MNRZFKEHSA-N 0.000 claims 1
- PBADSUYBIDNVGM-MNRZFKEHSA-N [2-amino-5-(3-fluorophenyl)-1,3-thiazol-4-yl]-[(1S,3S,5S)-3-(aminomethyl)-2-azabicyclo[3.1.0]hexan-2-yl]methanone 3-methyl-5-(trifluoromethyl)-1,2-oxazole-4-carboxylic acid Chemical compound CC1=NOC(C(F)(F)F)=C1C(O)=O.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O PBADSUYBIDNVGM-MNRZFKEHSA-N 0.000 claims 1
- BYJKDVRXONVAPA-IKGGRYGDSA-N [2-methyl-5-(3-methylphenyl)-1,3-thiazol-4-yl]-[(1s,3s,5s)-3-[[[4-(trifluoromethyl)pyrimidin-2-yl]amino]methyl]-2-azabicyclo[3.1.0]hexan-2-yl]methanone Chemical compound C([C@@H]1C[C@@H]2C[C@@H]2N1C(=O)C=1N=C(SC=1C=1C=C(C)C=CC=1)C)NC1=NC=CC(C(F)(F)F)=N1 BYJKDVRXONVAPA-IKGGRYGDSA-N 0.000 claims 1
- 230000003042 antagnostic effect Effects 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000005946 imidazo[1,2-a]pyridyl group Chemical group 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- URYSQMOHKJMWQI-NEWSRXKRSA-N n-[[(1s,3s,5s)-2-[2-amino-5-(3-methylphenyl)-1,3-thiazole-4-carbonyl]-2-azabicyclo[3.1.0]hexan-3-yl]methyl]-3-bromobenzamide Chemical compound CC1=CC=CC(C2=C(N=C(N)S2)C(=O)N2[C@@H](C[C@@H]3C[C@@H]32)CNC(=O)C=2C=C(Br)C=CC=2)=C1 URYSQMOHKJMWQI-NEWSRXKRSA-N 0.000 claims 1
- SMSKKKDQSPQPBB-HKBOAZHASA-N n-[[(1s,3s,5s)-2-[2-amino-5-(3-methylphenyl)-1,3-thiazole-4-carbonyl]-2-azabicyclo[3.1.0]hexan-3-yl]methyl]-3-ethynylbenzamide Chemical compound CC1=CC=CC(C2=C(N=C(N)S2)C(=O)N2[C@@H](C[C@@H]3C[C@@H]32)CNC(=O)C=2C=C(C=CC=2)C#C)=C1 SMSKKKDQSPQPBB-HKBOAZHASA-N 0.000 claims 1
- SFSKTVHOJFMXIW-HBFSDRIKSA-N n-[[(1s,3s,5s)-2-[2-amino-5-(3-methylphenyl)-1,3-thiazole-4-carbonyl]-2-azabicyclo[3.1.0]hexan-3-yl]methyl]-3-methylsulfanylbenzamide Chemical compound CSC1=CC=CC(C(=O)NC[C@H]2N([C@H]3C[C@H]3C2)C(=O)C2=C(SC(N)=N2)C=2C=C(C)C=CC=2)=C1 SFSKTVHOJFMXIW-HBFSDRIKSA-N 0.000 claims 1
- SINYBNKIDPMQMD-GIVPXCGWSA-N n-[[(1s,3s,5s)-2-[2-methyl-5-(3-methylphenyl)-1,3-thiazole-4-carbonyl]-2-azabicyclo[3.1.0]hexan-3-yl]methyl]-3-(trifluoromethyl)benzamide Chemical compound C([C@@H]1C[C@@H]2C[C@@H]2N1C(=O)C=1N=C(SC=1C=1C=C(C)C=CC=1)C)NC(=O)C1=CC=CC(C(F)(F)F)=C1 SINYBNKIDPMQMD-GIVPXCGWSA-N 0.000 claims 1
- WWIBMKSHGULDKS-UXPWSPDFSA-N n-[[(1s,3s,5s)-2-[5-(3-chlorophenyl)-2-methyl-1,3-thiazole-4-carbonyl]-2-azabicyclo[3.1.0]hexan-3-yl]methyl]-3-(trifluoromethyl)benzamide Chemical compound C([C@@H]1C[C@@H]2C[C@@H]2N1C(=O)C=1N=C(SC=1C=1C=C(Cl)C=CC=1)C)NC(=O)C1=CC=CC(C(F)(F)F)=C1 WWIBMKSHGULDKS-UXPWSPDFSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- QRDZFPUVLYEQTA-UHFFFAOYSA-N quinoline-8-carboxylic acid Chemical compound C1=CN=C2C(C(=O)O)=CC=CC2=C1 QRDZFPUVLYEQTA-UHFFFAOYSA-N 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 238000011282 treatment Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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| EP2079690B1 (en) * | 2006-09-29 | 2010-09-15 | Actelion Pharmaceuticals Ltd. | 3-aza-bicyclo[3.1.0]hexane derivatives |
| WO2008065626A2 (en) | 2006-12-01 | 2008-06-05 | Actelion Pharmaceuticals Ltd | 3-heteroaryl (amino or amido)-1- (biphenyl or phenylthiazolyl) carbonylpiperidine derivativesas orexin receptor inhibitors |
| CL2008000836A1 (es) * | 2007-03-26 | 2008-11-07 | Actelion Pharmaceuticals Ltd | Compuestos derivados de tiazolidina, antagonistas del receptor de orexina; composicion farmaceutica que los comprende; y su uso en el tratamiento de neurosis emocional, depresion grave, trastornos psicoticos, alzheimer, parkinson, dolor, entre otras. |
| US8030495B2 (en) | 2007-05-23 | 2011-10-04 | Coleman Paul J | Cyclopropyl pyrrolidine orexin receptor antagonists |
| EP2207778A2 (en) * | 2007-09-24 | 2010-07-21 | Actelion Pharmaceuticals Ltd. | Pyrrolidines and piperidines as orexin receptor antagonists |
| NZ588080A (en) * | 2008-02-21 | 2012-04-27 | Actelion Pharmaceuticals Ltd | 2-Aza-bicyclo[2.2.1]heptane derivatives |
| CA2722347A1 (en) * | 2008-04-30 | 2009-11-05 | Actelion Pharmaceuticals Ltd | Piperidine and pyrrolidine compounds |
| AU2009305005A1 (en) * | 2008-10-14 | 2010-04-22 | Actelion Pharmaceuticals Ltd | Phenethylamide derivatives and their heterocyclic analogues |
| EP2275421A1 (en) * | 2009-07-15 | 2011-01-19 | Rottapharm S.p.A. | Spiro amino compounds suitable for the treatment of inter alia sleep disorders and drug addiction |
| MX2012006909A (es) * | 2009-12-29 | 2012-07-10 | Suven Life Sciences Ltd | LIGANDOS DEL RECEPTOR NICOTINICO NEURONAL A4ß2 DE ACETILCOLINA. |
| MY160969A (en) * | 2010-09-22 | 2017-03-31 | Eisai R&D Man Co Ltd | Cyclopropane compounds |
| US9012489B2 (en) * | 2011-08-03 | 2015-04-21 | Boehringer Ingelheim International Gmbh | Phenyl-3-aza-bicyclo[3.1.0]hex-3-yl-methanones and the use thereof as medicament |
| WO2013050938A1 (en) | 2011-10-04 | 2013-04-11 | Actelion Pharmaceuticals Ltd | 3,7-diazabicyclo[3.3.1]nonane and 9-oxa-3,7-diazabicyclo[3.3.1]nonane derivatives |
| ITMI20112329A1 (it) * | 2011-12-21 | 2013-06-22 | Rottapharm Spa | Nuovi derivati spiro amminici |
| EP2811997B1 (en) | 2012-02-07 | 2018-04-11 | Eolas Therapeutics Inc. | Substituted prolines/piperidines as orexin receptor antagonists |
| US9440982B2 (en) | 2012-02-07 | 2016-09-13 | Eolas Therapeutics, Inc. | Substituted prolines/piperidines as orexin receptor antagonists |
| ITMI20120424A1 (it) | 2012-03-19 | 2013-09-20 | Rottapharm Spa | Composti chimici |
| LT2855453T (lt) | 2012-06-04 | 2017-02-27 | Actelion Pharmaceuticals Ltd. | Benzimidazolo prolino dariniai |
| CA2879460C (en) * | 2012-07-18 | 2021-10-19 | Garrett MORASKI | 5,5-heteroaromatic anti-infective compounds |
| US9493446B2 (en) | 2012-10-10 | 2016-11-15 | Actelion Pharmaceuticals Ltd. | Orexin receptor antagonists which are [ortho bi-(hetero-)aryl]-[2-(meta bi-(hetero-)aryl)-pyrrolidin-1-yl]-methanone derivatives |
| EP2970241A1 (en) | 2013-03-12 | 2016-01-20 | Actelion Pharmaceuticals Ltd. | Azetidine amide derivatives as orexin receptor antagonists |
| TWI621618B (zh) | 2013-03-13 | 2018-04-21 | 比利時商健生藥品公司 | 經取代２－氮雜雙環類及其作為食慾素受體調控劑之用途 |
| TW201444821A (zh) | 2013-03-13 | 2014-12-01 | Janssen Pharmaceutica Nv | 經取代之哌啶化合物及其作為食慾素受體調節劑之用途 |
| TW201444849A (zh) | 2013-03-13 | 2014-12-01 | Janssen Pharmaceutica Nv | 經取代的7-氮雜雙環類及其作為食慾激素受體調節劑之用途 |
| PT3077389T (pt) | 2013-12-03 | 2017-12-15 | Idorsia Pharmaceuticals Ltd | Forma cristalina de (s)-(2-(6-cloro-7-metil-1hbenzo[d]imidazol-2-il)-2-metilpirrolidin-1-il)(5-metoxi-2-(2h-1,2,3-triazol-2-il)fenil)metanona e a sua utilização como como antagonistas do receptor de orexina |
| UA119151C2 (uk) | 2013-12-03 | 2019-05-10 | Ідорсія Фармасьютікалз Лтд | КРИСТАЛІЧНА СОЛЬОВА ФОРМА (S)-(2-(6-ХЛОР-7-МЕТИЛ-1H-БЕНЗО[d]ІМІДАЗОЛ-2-ІЛ)-2-МЕТИЛПІРОЛІДИН-1-ІЛ)(5-МЕТОКСИ-2-(2H-1,2,3-ТРИАЗОЛ-2-ІЛ)ФЕНІЛ)МЕТАНОНУ ЯК АНТАГОНІСТ ОРЕКСИНОВОГО РЕЦЕПТОРА |
| SI3077391T1 (sl) | 2013-12-04 | 2018-11-30 | Idorsia Pharmaceuticals Ltd | Uporaba benzimidazol-prolinskih derivatov |
| TW201613864A (en) | 2014-02-20 | 2016-04-16 | Takeda Pharmaceutical | Novel compounds |
| WO2016025669A1 (en) | 2014-08-13 | 2016-02-18 | Eolas Therapeutics, Inc. | Difluoropyrrolidines as orexin receptor modulators |
| WO2016040789A1 (en) | 2014-09-11 | 2016-03-17 | Janssen Pharmaceutica Nv | Substituted 2-azabicycles and their use as orexin receptor modulators |
| RU2703297C2 (ru) | 2014-10-23 | 2019-10-16 | Эйсай Ар Энд Ди Менеджмент Ко., Лтд. | Композиции и способы для лечения бессонницы |
| CN106588900A (zh) * | 2015-10-20 | 2017-04-26 | 北京康辰医药科技有限公司 | 一种苯并双环化合物或其药学上可接受的盐、药物组合物及其应用 |
| PL3414241T3 (pl) | 2016-02-12 | 2022-10-03 | Astrazeneca Ab | Piperydyny podstawione halo jako modulatory receptora oreksyny |
| BR112018016983A2 (pt) * | 2016-02-26 | 2018-12-26 | Jiangsu Hengrui Medicine Co., Ltd. | nova toxina e método de preparação de intermediário da mesma |
| EP3454857A1 (en) | 2016-05-10 | 2019-03-20 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of autoimmune inflammatory diseases |
| EP3619199B1 (en) | 2017-05-03 | 2021-07-07 | Idorsia Pharmaceuticals Ltd | Preparation of 2-([1,2,3]triazol-2-yl)-benzoic acid derivatives |
| WO2019057946A1 (en) | 2017-09-25 | 2019-03-28 | F. Hoffmann-La Roche Ag | MULTI-CYCLIC AROMATIC COMPOUNDS AS D-FACTOR INHIBITORS |
| WO2020007964A1 (en) | 2018-07-05 | 2020-01-09 | Idorsia Pharmaceuticals Ltd | 2-(2-azabicyclo[3.1.0]hexan-1-yl)-1h-benzimidazole derivatives |
| WO2020007977A1 (en) | 2018-07-06 | 2020-01-09 | Idorsia Pharmaceuticals Ltd | 7-trifluoromethyl-[1,4]diazepan derivatives |
| WO2020099511A1 (en) | 2018-11-14 | 2020-05-22 | Idorsia Pharmaceuticals Ltd | Benzimidazole-2-methyl-morpholine derivatives |
| EP4196118A1 (en) | 2020-08-13 | 2023-06-21 | Boehringer Ingelheim International GmbH | Treatment of cognitive impairement associated with schizophrenia |
| CA3195702A1 (en) | 2020-10-13 | 2022-04-21 | Boehringer Ingelheim International Gmbh | Process of reworking |
| JP7681113B2 (ja) * | 2021-02-02 | 2025-05-21 | メッドシャイン ディスカバリー インコーポレイテッド | テトラヒドロピロロ環化合物及びその使用 |
| TW202400149A (zh) | 2022-05-13 | 2024-01-01 | 瑞士商愛杜西亞製藥有限公司 | 經噻唑并芳基-甲基取代之環狀肼-n-甲醯胺衍生物 |
| WO2025224168A1 (en) | 2024-04-24 | 2025-10-30 | Idorsia Pharmaceuticals Ltd | Aryl sulfone and sulfanone derivatives as orexin receptor modulators |
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- 2007-12-27 CL CL200703827A patent/CL2007003827A1/es unknown
- 2007-12-27 AR ARP070105930A patent/AR064561A1/es not_active Application Discontinuation
- 2007-12-27 TW TW096150631A patent/TW200833328A/zh unknown
- 2007-12-28 BR BRPI0720876-6A patent/BRPI0720876A2/pt not_active IP Right Cessation
- 2007-12-28 RU RU2009128739/04A patent/RU2460732C2/ru not_active IP Right Cessation
- 2007-12-28 JP JP2009543566A patent/JP2010514751A/ja active Pending
- 2007-12-28 ES ES07859531T patent/ES2364297T3/es active Active
- 2007-12-28 DE DE602007013937T patent/DE602007013937D1/de active Active
- 2007-12-28 HR HR20110509T patent/HRP20110509T1/hr unknown
- 2007-12-28 DK DK07859531.1T patent/DK2094690T3/da active
- 2007-12-28 MX MX2009006860A patent/MX2009006860A/es active IP Right Grant
- 2007-12-28 AU AU2007340944A patent/AU2007340944B2/en not_active Expired - Fee Related
- 2007-12-28 AT AT07859531T patent/ATE505467T1/de active
- 2007-12-28 CN CN2007800483236A patent/CN101568536B/zh not_active Expired - Fee Related
- 2007-12-28 EP EP07859531A patent/EP2094690B1/en active Active
- 2007-12-28 NZ NZ578642A patent/NZ578642A/en not_active IP Right Cessation
- 2007-12-28 CA CA002669821A patent/CA2669821A1/en not_active Abandoned
- 2007-12-28 PT PT07859531T patent/PT2094690E/pt unknown
- 2007-12-28 PL PL07859531T patent/PL2094690T3/pl unknown
- 2007-12-28 WO PCT/IB2007/055326 patent/WO2008081399A2/en not_active Ceased
- 2007-12-28 US US12/521,453 patent/US8288435B2/en not_active Expired - Fee Related
- 2007-12-28 SI SI200730639T patent/SI2094690T1/sl unknown
- 2007-12-28 MY MYPI20092751A patent/MY157344A/en unknown
- 2007-12-28 KR KR1020097015732A patent/KR20090094168A/ko not_active Ceased
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2009
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