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
Links
- 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
- KUWHRUFBXNLTJG-MNRZFKEHSA-N CC(C)(C1)OC2=C1C=CC=C2C(O)=O.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)(C1)OC2=C1C=CC=C2C(O)=O.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O KUWHRUFBXNLTJG-MNRZFKEHSA-N 0.000 claims 1
- RULLMWLCLABQLZ-MNRZFKEHSA-N CC(S1)=CN2C1=NC=C2C(O)=O.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(S1)=CN2C1=NC=C2C(O)=O.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O RULLMWLCLABQLZ-MNRZFKEHSA-N 0.000 claims 1
- FLZUVPOMHUIABI-OQNHHKPVSA-N CC1=C(C(O)=O)C2=CC=CC=C2N1C.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1 Chemical compound CC1=C(C(O)=O)C2=CC=CC=C2N1C.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1 FLZUVPOMHUIABI-OQNHHKPVSA-N 0.000 claims 1
- WIGPLNNUZQPNKX-OQNHHKPVSA-N CC1=C(C(O)=O)C2=CC=CC=C2N1C.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1 Chemical compound CC1=C(C(O)=O)C2=CC=CC=C2N1C.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1 WIGPLNNUZQPNKX-OQNHHKPVSA-N 0.000 claims 1
- DXPRMQDJSLWVNK-DSMRVHDJSA-N CC1=C(C(O)=O)C2=CC=CC=C2N1C.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1 Chemical compound CC1=C(C(O)=O)C2=CC=CC=C2N1C.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1 DXPRMQDJSLWVNK-DSMRVHDJSA-N 0.000 claims 1
- LKSJIOGYEBPAKJ-MNRZFKEHSA-N CC1=C(C(O)=O)C2=CC=CC=C2N1C.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O Chemical compound CC1=C(C(O)=O)C2=CC=CC=C2N1C.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O LKSJIOGYEBPAKJ-MNRZFKEHSA-N 0.000 claims 1
- ZLPHCPJNCLOBOE-UQGASIHSSA-N CC1=C(C(O)=O)N(C=CS2)C2=N1.CC1=CC(C2=C(C(N3[C@H](CN)C[C@H]4[C@@H]3C4)=O)N=C(N)S2)=CC=C1 Chemical compound CC1=C(C(O)=O)N(C=CS2)C2=N1.CC1=CC(C2=C(C(N3[C@H](CN)C[C@H]4[C@@H]3C4)=O)N=C(N)S2)=CC=C1 ZLPHCPJNCLOBOE-UQGASIHSSA-N 0.000 claims 1
- JHZMODRRITUVLD-OQNHHKPVSA-N CC1=C(C(O)=O)N(C=CS2)C2=N1.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=C2)=CC=C2F)S1 Chemical compound CC1=C(C(O)=O)N(C=CS2)C2=N1.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=C2)=CC=C2F)S1 JHZMODRRITUVLD-OQNHHKPVSA-N 0.000 claims 1
- YAPCNVLYIKNKMN-OQNHHKPVSA-N CC1=C(C(O)=O)N(C=CS2)C2=N1.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1 Chemical compound CC1=C(C(O)=O)N(C=CS2)C2=N1.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1 YAPCNVLYIKNKMN-OQNHHKPVSA-N 0.000 claims 1
- KVSPDFAEMOMBMH-DSMRVHDJSA-N CC1=C(C(O)=O)N(C=CS2)C2=N1.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1 Chemical compound CC1=C(C(O)=O)N(C=CS2)C2=N1.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1 KVSPDFAEMOMBMH-DSMRVHDJSA-N 0.000 claims 1
- GSPKPMAPORVTIK-FNIUFUSKSA-N CC1=C(C(O)=O)N(C=CS2)C2=N1.CC1=NC=C(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)C(C2=CC=CC=C2)=N1 Chemical compound CC1=C(C(O)=O)N(C=CS2)C2=N1.CC1=NC=C(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)C(C2=CC=CC=C2)=N1 GSPKPMAPORVTIK-FNIUFUSKSA-N 0.000 claims 1
- SPJCUODOKMAWRO-UDYGKFQRSA-N CC1=C(C(O)=O)N(C=CS2)C2=N1.CN(C)C1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC=C2)S1 Chemical compound CC1=C(C(O)=O)N(C=CS2)C2=N1.CN(C)C1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC=C2)S1 SPJCUODOKMAWRO-UDYGKFQRSA-N 0.000 claims 1
- KOQFOCVLTANZOV-LJZXGAKHSA-N CC1=C(C(O)=O)N(C=CS2)C2=N1.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C(C=CC=C1)=C1N1N=CC=C1)=O Chemical compound CC1=C(C(O)=O)N(C=CS2)C2=N1.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C(C=CC=C1)=C1N1N=CC=C1)=O KOQFOCVLTANZOV-LJZXGAKHSA-N 0.000 claims 1
- RQYYRAFBNZXJNA-MNRZFKEHSA-N CC1=C(C(O)=O)N(C=CS2)C2=N1.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O Chemical compound CC1=C(C(O)=O)N(C=CS2)C2=N1.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O RQYYRAFBNZXJNA-MNRZFKEHSA-N 0.000 claims 1
- NHVFBTOGFOGIER-MNRZFKEHSA-N CC1=C(C(O)=O)N=C(C)O1.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O Chemical compound CC1=C(C(O)=O)N=C(C)O1.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O NHVFBTOGFOGIER-MNRZFKEHSA-N 0.000 claims 1
- YNVJHHXMAMKTNV-OQNHHKPVSA-N CC1=C(C(O)=O)SC2=NC=CN12.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1 Chemical compound CC1=C(C(O)=O)SC2=NC=CN12.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1 YNVJHHXMAMKTNV-OQNHHKPVSA-N 0.000 claims 1
- TYQATEDOQVJVRL-DSMRVHDJSA-N CC1=C(C(O)=O)SC2=NC=CN12.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1 Chemical compound CC1=C(C(O)=O)SC2=NC=CN12.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1 TYQATEDOQVJVRL-DSMRVHDJSA-N 0.000 claims 1
- NYZIFPGPODIQKI-MNRZFKEHSA-N CC1=C(C(O)=O)SC2=NC=CN12.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O Chemical compound CC1=C(C(O)=O)SC2=NC=CN12.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O NYZIFPGPODIQKI-MNRZFKEHSA-N 0.000 claims 1
- WESCESGPFXVNQU-MNRZFKEHSA-N CC1=C(C(O)=O)SC=N1.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O Chemical compound CC1=C(C(O)=O)SC=N1.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O WESCESGPFXVNQU-MNRZFKEHSA-N 0.000 claims 1
- RAYQNCQRRYYAPF-IZIIKQMZSA-N CC1=CC(=C(O1)C1=CC=CC=C1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC1=NC2=C(C=CC=C2C=C1)C(=O)N Chemical compound CC1=CC(=C(O1)C1=CC=CC=C1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC1=NC2=C(C=CC=C2C=C1)C(=O)N RAYQNCQRRYYAPF-IZIIKQMZSA-N 0.000 claims 1
- UQMRJUPGKBVNNR-UQGASIHSSA-N CC1=CC(C2=C(C(N3[C@H](CN)C[C@H]4[C@@H]3C4)=O)N=C(N)S2)=CC=C1.CN1N=C(C(O)=O)C2=CC=CC=C12 Chemical compound CC1=CC(C2=C(C(N3[C@H](CN)C[C@H]4[C@@H]3C4)=O)N=C(N)S2)=CC=C1.CN1N=C(C(O)=O)C2=CC=CC=C12 UQMRJUPGKBVNNR-UQGASIHSSA-N 0.000 claims 1
- JJGRTEIPTQBSAD-UQGASIHSSA-N CC1=CC(C2=C(C(N3[C@H](CN)C[C@H]4[C@@H]3C4)=O)N=C(N)S2)=CC=C1.OC(C1=C(CCO2)C2=CC=C1)=O Chemical compound CC1=CC(C2=C(C(N3[C@H](CN)C[C@H]4[C@@H]3C4)=O)N=C(N)S2)=CC=C1.OC(C1=C(CCO2)C2=CC=C1)=O JJGRTEIPTQBSAD-UQGASIHSSA-N 0.000 claims 1
- LZYYOHZAZIRSGR-UQGASIHSSA-N CC1=CC(C2=C(C(N3[C@H](CN)C[C@H]4[C@@H]3C4)=O)N=C(N)S2)=CC=C1.OC(C1=C2OCCOC2=CS1)=O Chemical compound CC1=CC(C2=C(C(N3[C@H](CN)C[C@H]4[C@@H]3C4)=O)N=C(N)S2)=CC=C1.OC(C1=C2OCCOC2=CS1)=O LZYYOHZAZIRSGR-UQGASIHSSA-N 0.000 claims 1
- WNQQFSFFHPINGS-UQGASIHSSA-N CC1=CC(C2=C(C(N3[C@H](CN)C[C@H]4[C@@H]3C4)=O)N=C(N)S2)=CC=C1.OC(C1=CC=CC2=C1OCC2)=O Chemical compound CC1=CC(C2=C(C(N3[C@H](CN)C[C@H]4[C@@H]3C4)=O)N=C(N)S2)=CC=C1.OC(C1=CC=CC2=C1OCC2)=O WNQQFSFFHPINGS-UQGASIHSSA-N 0.000 claims 1
- PEJHRTAIJQLAIF-UQGASIHSSA-N CC1=CC(C2=C(C(N3[C@H](CN)C[C@H]4[C@@H]3C4)=O)N=C(N)S2)=CC=C1.OC(C1=CC=CC2=C1OCCO2)=O Chemical compound CC1=CC(C2=C(C(N3[C@H](CN)C[C@H]4[C@@H]3C4)=O)N=C(N)S2)=CC=C1.OC(C1=CC=CC2=C1OCCO2)=O PEJHRTAIJQLAIF-UQGASIHSSA-N 0.000 claims 1
- FRCHDRXUIOTMNQ-UQGASIHSSA-N CC1=CC(C2=C(C(N3[C@H](CN)C[C@H]4[C@@H]3C4)=O)N=C(N)S2)=CC=C1.OC(C1=NOC2=C1C=CC=C2)=O Chemical compound CC1=CC(C2=C(C(N3[C@H](CN)C[C@H]4[C@@H]3C4)=O)N=C(N)S2)=CC=C1.OC(C1=NOC2=C1C=CC=C2)=O FRCHDRXUIOTMNQ-UQGASIHSSA-N 0.000 claims 1
- JNPBQDKASYMXND-DSMRVHDJSA-N CC1=CN(C=CS2)C2=C1C(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 CC1=CN(C=CS2)C2=C1C(O)=O.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1 JNPBQDKASYMXND-DSMRVHDJSA-N 0.000 claims 1
- NWZSUJVQCMRKAK-MNRZFKEHSA-N CC1=CSC2=NC=C(C(O)=O)N12.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O Chemical compound CC1=CSC2=NC=C(C(O)=O)N12.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O NWZSUJVQCMRKAK-MNRZFKEHSA-N 0.000 claims 1
- GOFIHZDMYOPBMP-DYTHMOEWSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=C2)=CC(Br)=C2F)S1.OC(C1=C(CCO2)C2=CC=C1)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=C2)=CC(Br)=C2F)S1.OC(C1=C(CCO2)C2=CC=C1)=O GOFIHZDMYOPBMP-DYTHMOEWSA-N 0.000 claims 1
- XRKGVFNKPPIVOO-DYTHMOEWSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=C2)=CC(Br)=C2F)S1.OC(C1=C2N=CC=CC2=CC=C1)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=C2)=CC(Br)=C2F)S1.OC(C1=C2N=CC=CC2=CC=C1)=O XRKGVFNKPPIVOO-DYTHMOEWSA-N 0.000 claims 1
- CWTGIVPYGHVPMU-DYTHMOEWSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=C2)=CC(Br)=C2F)S1.OC(C1=CN=C2N1C=CC=C2)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=C2)=CC(Br)=C2F)S1.OC(C1=CN=C2N1C=CC=C2)=O CWTGIVPYGHVPMU-DYTHMOEWSA-N 0.000 claims 1
- QGAQKPZILJRFGO-DYTHMOEWSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=C2)=CC(Cl)=C2Cl)S1.OC(C1=CN=C2N1C=CC=C2)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=C2)=CC(Cl)=C2Cl)S1.OC(C1=CN=C2N1C=CC=C2)=O QGAQKPZILJRFGO-DYTHMOEWSA-N 0.000 claims 1
- SCEOESMICHHLTD-DYTHMOEWSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=C2)=CC(F)=C2F)S1.OC(C1=C(CCO2)C2=CC=C1)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=C2)=CC(F)=C2F)S1.OC(C1=C(CCO2)C2=CC=C1)=O SCEOESMICHHLTD-DYTHMOEWSA-N 0.000 claims 1
- SISNQWWOXMRLPM-OQNHHKPVSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=C2)=CC=C2Br)S1.OC(C1=C(CCO2)C2=CC=C1)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=C2)=CC=C2Br)S1.OC(C1=C(CCO2)C2=CC=C1)=O SISNQWWOXMRLPM-OQNHHKPVSA-N 0.000 claims 1
- OZXZRTOLSWBDHS-OQNHHKPVSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=C2)=CC=C2F)S1.OC(C1=C(CCO2)C2=CC=C1)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=C2)=CC=C2F)S1.OC(C1=C(CCO2)C2=CC=C1)=O OZXZRTOLSWBDHS-OQNHHKPVSA-N 0.000 claims 1
- LLLNNKLXXMRVDT-OQNHHKPVSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=C2)=CC=C2F)S1.OC(C1=CC=CC2=C1OCCO2)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=C2)=CC=C2F)S1.OC(C1=CC=CC2=C1OCCO2)=O LLLNNKLXXMRVDT-OQNHHKPVSA-N 0.000 claims 1
- SRSCVAOQRVDDKM-TXRPFBSWSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=CC=C2Cl)=C2Cl)S1.OC(C1=C(CCO2)C2=CC=C1)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C(C=CC=C2Cl)=C2Cl)S1.OC(C1=C(CCO2)C2=CC=C1)=O SRSCVAOQRVDDKM-TXRPFBSWSA-N 0.000 claims 1
- QZARELYKXDMEOE-DYTHMOEWSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=C(C(F)(F)F)C=CC=C2)S1.OC(C1=CC=CC2=C1OCCO2)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=C(C(F)(F)F)C=CC=C2)S1.OC(C1=CC=CC2=C1OCCO2)=O QZARELYKXDMEOE-DYTHMOEWSA-N 0.000 claims 1
- POEKCXHTEIQOES-LJZXGAKHSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=C(C)C(F)=CC=C2)S1.OC(C1=C(CCO2)C2=CC=C1)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=C(C)C(F)=CC=C2)S1.OC(C1=C(CCO2)C2=CC=C1)=O POEKCXHTEIQOES-LJZXGAKHSA-N 0.000 claims 1
- FSDBEHUKXVWVRQ-LJZXGAKHSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=C(C)C(F)=CC=C2)S1.OC(C1=C2N=CC=CC2=CC=C1)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=C(C)C(F)=CC=C2)S1.OC(C1=C2N=CC=CC2=CC=C1)=O FSDBEHUKXVWVRQ-LJZXGAKHSA-N 0.000 claims 1
- VGGPRHQUIVRJQW-BZSDZJHCSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(C)=C(C)C=C2)S1.OC(C1=C(CCO2)C2=CC=C1)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(C)=C(C)C=C2)S1.OC(C1=C(CCO2)C2=CC=C1)=O VGGPRHQUIVRJQW-BZSDZJHCSA-N 0.000 claims 1
- ITJHFWCJRVSPKU-BZSDZJHCSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(C)=C(C)C=C2)S1.OC(C1=CN=C2N1C=CC=C2)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(C)=C(C)C=C2)S1.OC(C1=CN=C2N1C=CC=C2)=O ITJHFWCJRVSPKU-BZSDZJHCSA-N 0.000 claims 1
- GXNZIZSEDQBWQV-KHUAAREISA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(C)=CC(C)=C2)S1.OC(C1=C(CCO2)C2=CC=C1)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(C)=CC(C)=C2)S1.OC(C1=C(CCO2)C2=CC=C1)=O GXNZIZSEDQBWQV-KHUAAREISA-N 0.000 claims 1
- LGAMFDNYFBEDQH-OQNHHKPVSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1.OC(C1=C(CCO2)C2=CC=C1)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1.OC(C1=C(CCO2)C2=CC=C1)=O LGAMFDNYFBEDQH-OQNHHKPVSA-N 0.000 claims 1
- QGYFFLBUJQYCRH-OQNHHKPVSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1.OC(C1=C2OCCOC2=CS1)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1.OC(C1=C2OCCOC2=CS1)=O QGYFFLBUJQYCRH-OQNHHKPVSA-N 0.000 claims 1
- VCDUQJZQTVOYRS-OQNHHKPVSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1.OC(C1=CC(F)=CC2=C1OCOC2)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1.OC(C1=CC(F)=CC2=C1OCOC2)=O VCDUQJZQTVOYRS-OQNHHKPVSA-N 0.000 claims 1
- QQDTVITZXHVPDH-OQNHHKPVSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1.OC(C1=CC=CC2=C1OCCO2)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1.OC(C1=CC=CC2=C1OCCO2)=O QQDTVITZXHVPDH-OQNHHKPVSA-N 0.000 claims 1
- JBXFCEWXGJPCJO-OQNHHKPVSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1.OC(C1=CN=C2N1C=CC=C2)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1.OC(C1=CN=C2N1C=CC=C2)=O JBXFCEWXGJPCJO-OQNHHKPVSA-N 0.000 claims 1
- VBNMSSHKPBTYLW-OQNHHKPVSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1.OC(C1=NOC2=C1C=CC=C2)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1.OC(C1=NOC2=C1C=CC=C2)=O VBNMSSHKPBTYLW-OQNHHKPVSA-N 0.000 claims 1
- QLMDJPMWMBLEJY-OQSTVXQLSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=C(C)C=C2)S1.OC(C1=C2N=CC=CC2=CC=C1)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=C(C)C=C2)S1.OC(C1=C2N=CC=CC2=CC=C1)=O QLMDJPMWMBLEJY-OQSTVXQLSA-N 0.000 claims 1
- ZYARUCBLHCAXAL-OQNHHKPVSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1.CN1C2=CC=CC=C2C(C(O)=O)=C1 Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1.CN1C2=CC=CC=C2C(C(O)=O)=C1 ZYARUCBLHCAXAL-OQNHHKPVSA-N 0.000 claims 1
- KEIWSXOLADPUQU-OQNHHKPVSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1.CN1N=CC(C(O)=O)=C1C(F)(F)F Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1.CN1N=CC(C(O)=O)=C1C(F)(F)F KEIWSXOLADPUQU-OQNHHKPVSA-N 0.000 claims 1
- WCNSSVFMKVNAAX-OQNHHKPVSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1.COC1=CC(C(O)=O)=NC2=CC=CC=C12 Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1.COC1=CC(C(O)=O)=NC2=CC=CC=C12 WCNSSVFMKVNAAX-OQNHHKPVSA-N 0.000 claims 1
- TUEGZKYWCLLFIZ-OQNHHKPVSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1.OC(C1=C(CCO2)C2=CC=C1)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1.OC(C1=C(CCO2)C2=CC=C1)=O TUEGZKYWCLLFIZ-OQNHHKPVSA-N 0.000 claims 1
- PSINRWZBOCFCTA-OQNHHKPVSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1.OC(C1=CC(F)=CC2=C1OCOC2)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1.OC(C1=CC(F)=CC2=C1OCOC2)=O PSINRWZBOCFCTA-OQNHHKPVSA-N 0.000 claims 1
- SSYBEWDXZGRLSO-OQNHHKPVSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1.OC(C1=CC2=CC(F)=CC=C2N1)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1.OC(C1=CC2=CC(F)=CC=C2N1)=O SSYBEWDXZGRLSO-OQNHHKPVSA-N 0.000 claims 1
- VGTKOCQSAVJIDV-OQNHHKPVSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1.OC(C1=CC2=CC=CC(F)=C2N1)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1.OC(C1=CC2=CC=CC(F)=C2N1)=O VGTKOCQSAVJIDV-OQNHHKPVSA-N 0.000 claims 1
- MQKDUBFNRBIDFO-OQNHHKPVSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1.OC(C1=CN=C2SC=CN12)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1.OC(C1=CN=C2SC=CN12)=O MQKDUBFNRBIDFO-OQNHHKPVSA-N 0.000 claims 1
- JQUZQJDUWLXAIT-OQNHHKPVSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1.OC(C1=NC2=CC=CC=C2C=C1)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1.OC(C1=NC2=CC=CC=C2C=C1)=O JQUZQJDUWLXAIT-OQNHHKPVSA-N 0.000 claims 1
- VNCHHHLGIZPLJC-DSMRVHDJSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.CN(C(C(O)=O)=CC1=C2)C1=CC=C2F Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.CN(C(C(O)=O)=CC1=C2)C1=CC=C2F VNCHHHLGIZPLJC-DSMRVHDJSA-N 0.000 claims 1
- FIEUMDUYWCWKSZ-DSMRVHDJSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.CN1C(C=CC=C2C(O)=O)=C2OCC1 Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.CN1C(C=CC=C2C(O)=O)=C2OCC1 FIEUMDUYWCWKSZ-DSMRVHDJSA-N 0.000 claims 1
- PULBYRSYPNKDST-DSMRVHDJSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.COC(CC1=C(C=C2)C(O)=O)OC1=C2Cl Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.COC(CC1=C(C=C2)C(O)=O)OC1=C2Cl PULBYRSYPNKDST-DSMRVHDJSA-N 0.000 claims 1
- PRBGZDFINBXSPX-DSMRVHDJSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C(C=C1)=C(C=CO2)C2=C1Cl)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C(C=C1)=C(C=CO2)C2=C1Cl)=O PRBGZDFINBXSPX-DSMRVHDJSA-N 0.000 claims 1
- UWKLSYQHFJVPCS-DSMRVHDJSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C(C=C1)=C(C=CO2)C2=C1F)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C(C=C1)=C(C=CO2)C2=C1F)=O UWKLSYQHFJVPCS-DSMRVHDJSA-N 0.000 claims 1
- PWYLDCJPDSLPPM-DSMRVHDJSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C(C=CC=C1S2)=C1N=C2Cl)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C(C=CC=C1S2)=C1N=C2Cl)=O PWYLDCJPDSLPPM-DSMRVHDJSA-N 0.000 claims 1
- SPZFSMYSAKPGOG-DSMRVHDJSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C(N(C=CS1)C1=N1)=C1Cl)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C(N(C=CS1)C1=N1)=C1Cl)=O SPZFSMYSAKPGOG-DSMRVHDJSA-N 0.000 claims 1
- QGARLNZDALEIRY-DSMRVHDJSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C1=C(C(F)(F)F)N=C2SC=CN12)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C1=C(C(F)(F)F)N=C2SC=CN12)=O QGARLNZDALEIRY-DSMRVHDJSA-N 0.000 claims 1
- SRVIZSZWNOJYCW-DSMRVHDJSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C1=C2OCCOC2=CS1)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C1=C2OCCOC2=CS1)=O SRVIZSZWNOJYCW-DSMRVHDJSA-N 0.000 claims 1
- FRMNQJOSNYAKAU-DSMRVHDJSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C1=C2SC=CN2C=C1)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C1=C2SC=CN2C=C1)=O FRMNQJOSNYAKAU-DSMRVHDJSA-N 0.000 claims 1
- KRTDTZWRWOYDRV-DSMRVHDJSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C1=CC=CC2=C1OCCO2)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C1=CC=CC2=C1OCCO2)=O KRTDTZWRWOYDRV-DSMRVHDJSA-N 0.000 claims 1
- ZXRPBUZSSSWPRW-DSMRVHDJSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C1=CN=C2N1C=CC=C2)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C1=CN=C2N1C=CC=C2)=O ZXRPBUZSSSWPRW-DSMRVHDJSA-N 0.000 claims 1
- XZIPSKXSMPVJPI-DSMRVHDJSA-N CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C1=CN=C2SC=CN12)=O Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1.OC(C1=CN=C2SC=CN12)=O XZIPSKXSMPVJPI-DSMRVHDJSA-N 0.000 claims 1
- ZBQMNMAEYXPBKO-DSMRVHDJSA-N CC1=NC(C=CC=C2C(O)=O)=C2O1.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1 Chemical compound CC1=NC(C=CC=C2C(O)=O)=C2O1.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1 ZBQMNMAEYXPBKO-DSMRVHDJSA-N 0.000 claims 1
- UXIIOFUTBBGFDX-STSQHVNTSA-N CC1=NC=C(C(=N1)C1=CC=CC=C1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC=1OC=2C(C1)=C(C=CC2)C(=O)N Chemical compound CC1=NC=C(C(=N1)C1=CC=CC=C1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC=1OC=2C(C1)=C(C=CC2)C(=O)N UXIIOFUTBBGFDX-STSQHVNTSA-N 0.000 claims 1
- CFFZQLRGIGCFQU-FNIUFUSKSA-N CC1=NC=C(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)C(C2=CC=CC=C2)=N1.OC(C1=CC=CC2=C1OCCO2)=O Chemical compound CC1=NC=C(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)C(C2=CC=CC=C2)=N1.OC(C1=CC=CC2=C1OCCO2)=O CFFZQLRGIGCFQU-FNIUFUSKSA-N 0.000 claims 1
- IKVTXDALCQHSEB-OQNHHKPVSA-N CC1=NN(C)C(C(O)=O)=C1.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1 Chemical compound CC1=NN(C)C(C(O)=O)=C1.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1 IKVTXDALCQHSEB-OQNHHKPVSA-N 0.000 claims 1
- MXVVEHZAHSHHIP-OQNHHKPVSA-N CC1=NN(C)C(C(O)=O)=C1.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1 Chemical compound CC1=NN(C)C(C(O)=O)=C1.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1 MXVVEHZAHSHHIP-OQNHHKPVSA-N 0.000 claims 1
- UQJGKKJDJPOWON-DSMRVHDJSA-N CC1=NN(C)C(C(O)=O)=C1.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1 Chemical compound CC1=NN(C)C(C(O)=O)=C1.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1 UQJGKKJDJPOWON-DSMRVHDJSA-N 0.000 claims 1
- BPJHJMYGDWPKCM-MNRZFKEHSA-N CC1=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 CC1=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 BPJHJMYGDWPKCM-MNRZFKEHSA-N 0.000 claims 1
- YJMWOCVFQQWIKM-MNRZFKEHSA-N CC1=NN(C)C=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 Chemical compound CC1=NN(C)C=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 YJMWOCVFQQWIKM-MNRZFKEHSA-N 0.000 claims 1
- RZKRXJFBPFODCL-UQGASIHSSA-N CC1=NOC(C)=C1C(O)=O.CC1=CC(C2=C(C(N3[C@H](CN)C[C@H]4[C@@H]3C4)=O)N=C(N)S2)=CC=C1 Chemical compound CC1=NOC(C)=C1C(O)=O.CC1=CC(C2=C(C(N3[C@H](CN)C[C@H]4[C@@H]3C4)=O)N=C(N)S2)=CC=C1 RZKRXJFBPFODCL-UQGASIHSSA-N 0.000 claims 1
- PIVBZLUHPAFAHR-DSMRVHDJSA-N CC1=NOC(C)=C1C(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 CC1=NOC(C)=C1C(O)=O.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC=CC(C)=C2)S1 PIVBZLUHPAFAHR-DSMRVHDJSA-N 0.000 claims 1
- MJPZEQHMMUEOAR-MNRZFKEHSA-N CC1=NOC(C)=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 Chemical compound CC1=NOC(C)=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 MJPZEQHMMUEOAR-MNRZFKEHSA-N 0.000 claims 1
- NHZPEZRGSCBLII-CBQOVEMMSA-N CC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC1=NC2=C(C=CC=C2C=C1)C(=O)N)C1=CC=CC=C1 Chemical compound CC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC1=NC2=C(C=CC=C2C=C1)C(=O)N)C1=CC=CC=C1 NHZPEZRGSCBLII-CBQOVEMMSA-N 0.000 claims 1
- LEEGZFPBEGBWNJ-QAVZRRRASA-N CC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC1OC2=C(C=CC=C2CC1)C(=O)N)C=1C=C(C=CC1)C Chemical compound CC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC1OC2=C(C=CC=C2CC1)C(=O)N)C=1C=C(C=CC1)C LEEGZFPBEGBWNJ-QAVZRRRASA-N 0.000 claims 1
- DCSZNPDJYAUKIL-NTLLOMIDSA-N CC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC1OC=2C(C1)=C(C=CC2)C(=O)N)C2=CC=CC=C2 Chemical compound CC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC1OC=2C(C1)=C(C=CC2)C(=O)N)C2=CC=CC=C2 DCSZNPDJYAUKIL-NTLLOMIDSA-N 0.000 claims 1
- XBTXNSXLCJSOLU-NWSQWKLXSA-N CC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC=1C(=NC2=CC=CC=C2C1)C(=O)N)C=1C=C(C=CC1)C Chemical compound CC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC=1C(=NC2=CC=CC=C2C1)C(=O)N)C=1C=C(C=CC1)C XBTXNSXLCJSOLU-NWSQWKLXSA-N 0.000 claims 1
- FJASTOXDMXDBOG-UWVAXJGDSA-N CC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC=1OC2=C(N1)C=CC=C2C(=O)N)C=2C=C(C=CC2)C Chemical compound CC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC=1OC2=C(N1)C=CC=C2C(=O)N)C=2C=C(C=CC2)C FJASTOXDMXDBOG-UWVAXJGDSA-N 0.000 claims 1
- QKOYWHWHCNYGNM-FGSXEWAUSA-N CC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC=1OC=2C(C1)=C(C=CC2)C(=O)N)C=2C=C(C=CC2)C Chemical compound CC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC=1OC=2C(C1)=C(C=CC2)C(=O)N)C=2C=C(C=CC2)C QKOYWHWHCNYGNM-FGSXEWAUSA-N 0.000 claims 1
- MTGZUSSVNHWEAN-UWVAXJGDSA-N CC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC=1SC2=C(N1)C=CC=C2C(=O)N)C=2C=C(C=CC2)C Chemical compound CC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC=1SC2=C(N1)C=CC=C2C(=O)N)C=2C=C(C=CC2)C MTGZUSSVNHWEAN-UWVAXJGDSA-N 0.000 claims 1
- APXPIJGNQHNDFH-OQNHHKPVSA-N CCN1N=C(C)C(C(O)=O)=C1.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1 Chemical compound CCN1N=C(C)C(C(O)=O)=C1.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1 APXPIJGNQHNDFH-OQNHHKPVSA-N 0.000 claims 1
- MYCNRAGQXYYGME-OQNHHKPVSA-N CCN1N=C(C)C(C(O)=O)=C1.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1 Chemical compound CCN1N=C(C)C(C(O)=O)=C1.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1 MYCNRAGQXYYGME-OQNHHKPVSA-N 0.000 claims 1
- BDIFBNHUPBUDDU-MNRZFKEHSA-N CCN1N=C(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 CCN1N=C(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 BDIFBNHUPBUDDU-MNRZFKEHSA-N 0.000 claims 1
- TYTFOJUQCYGDDN-OQNHHKPVSA-N CCN1N=C(C)C=C1C(O)=O.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1 Chemical compound CCN1N=C(C)C=C1C(O)=O.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1 TYTFOJUQCYGDDN-OQNHHKPVSA-N 0.000 claims 1
- ZOYUCRSUYIVDNJ-OQNHHKPVSA-N CCN1N=C(C)C=C1C(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 CCN1N=C(C)C=C1C(O)=O.CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(F)=CC=C2)S1 ZOYUCRSUYIVDNJ-OQNHHKPVSA-N 0.000 claims 1
- PSVZWODQSJMPSW-MNRZFKEHSA-N CCN1N=C(C)C=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 Chemical compound CCN1N=C(C)C=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 PSVZWODQSJMPSW-MNRZFKEHSA-N 0.000 claims 1
- ZSFIQQNEIJOUMN-OQNHHKPVSA-N CCOC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1.OC(C1=CN=C2N1C=CC=C2)=O Chemical compound CCOC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(Cl)=CC=C2)S1.OC(C1=CN=C2N1C=CC=C2)=O ZSFIQQNEIJOUMN-OQNHHKPVSA-N 0.000 claims 1
- ONYSOYUGYRTYFV-MNRZFKEHSA-N CN(C(C(O)=O)=CC1=C2)C1=CC=C2F.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O Chemical compound CN(C(C(O)=O)=CC1=C2)C1=CC=C2F.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O ONYSOYUGYRTYFV-MNRZFKEHSA-N 0.000 claims 1
- FCKRSHPNLZPPSL-MNRZFKEHSA-N CN1C2=CC=CC=C2C(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 CN1C2=CC=CC=C2C(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 FCKRSHPNLZPPSL-MNRZFKEHSA-N 0.000 claims 1
- MQPKAWDFWUTSGR-MNRZFKEHSA-N CN1N=C(C=CC=C2)C2=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 Chemical compound CN1N=C(C=CC=C2)C2=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 MQPKAWDFWUTSGR-MNRZFKEHSA-N 0.000 claims 1
- VXFTWAQBDVCGBH-MNRZFKEHSA-N CN1N=CC(C(O)=O)=C1C(F)(F)F.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O Chemical compound CN1N=CC(C(O)=O)=C1C(F)(F)F.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O VXFTWAQBDVCGBH-MNRZFKEHSA-N 0.000 claims 1
- XBCPRANUULGXBF-MNRZFKEHSA-N COC1=CC(C(O)=O)=NC2=CC=CC=C12.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O Chemical compound COC1=CC(C(O)=O)=NC2=CC=CC=C12.NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O XBCPRANUULGXBF-MNRZFKEHSA-N 0.000 claims 1
- UAIXHPMPWGOQIR-LZNRXBQRSA-N COC=1C=C(C=CC1)C1=C(N=CS1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC1=NC2=C(C=CC=C2C=C1)C(=O)N Chemical compound COC=1C=C(C=CC1)C1=C(N=CS1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC1=NC2=C(C=CC=C2C=C1)C(=O)N UAIXHPMPWGOQIR-LZNRXBQRSA-N 0.000 claims 1
- INDCSOVMYIUZDY-PBEJRMEISA-N ClC=1C=C(C=CC1)C1=C(N=CS1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC1=NC2=C(C=CC=C2C=C1)C(=O)N Chemical compound ClC=1C=C(C=CC1)C1=C(N=CS1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC1=NC2=C(C=CC=C2C=C1)C(=O)N INDCSOVMYIUZDY-PBEJRMEISA-N 0.000 claims 1
- ZYQJTKUXUQWPIG-MIAKESKMSA-N ClC=1C=C(C=CC1)C=1C(=CC=CC1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC=1OC=2C(C1)=C(C=CC2)C(=O)N Chemical compound ClC=1C=C(C=CC1)C=1C(=CC=CC1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC=1OC=2C(C1)=C(C=CC2)C(=O)N ZYQJTKUXUQWPIG-MIAKESKMSA-N 0.000 claims 1
- VOHSYHSJWJHTID-YPBQGGFRSA-N FC1=C(C=CC=C1)C=1C(=CC=CC1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC=1OC=2C(C1)=C(C=CC2)C(=O)N Chemical compound FC1=C(C=CC=C1)C=1C(=CC=CC1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC=1OC=2C(C1)=C(C=CC2)C(=O)N VOHSYHSJWJHTID-YPBQGGFRSA-N 0.000 claims 1
- XUKPATCOXLUDDR-STSQHVNTSA-N N1=C(C=CC2=CC=CC=C12)C(=O)NC[C@H]1N([C@H]2C[C@H]2C1)C(=O)C=1N=C(SC1C1=CC(=C(C=C1)Cl)Cl)C Chemical compound N1=C(C=CC2=CC=CC=C12)C(=O)NC[C@H]1N([C@H]2C[C@H]2C1)C(=O)C=1N=C(SC1C1=CC(=C(C=C1)Cl)Cl)C XUKPATCOXLUDDR-STSQHVNTSA-N 0.000 claims 1
- IUJAKAZYMMOLKU-STSQHVNTSA-N N1=C(C=CC2=CC=CC=C12)C(=O)NC[C@H]1N([C@H]2C[C@H]2C1)C(=O)C=1N=C(SC1C1=CC(=C(C=C1)F)F)C Chemical compound N1=C(C=CC2=CC=CC=C12)C(=O)NC[C@H]1N([C@H]2C[C@H]2C1)C(=O)C=1N=C(SC1C1=CC(=C(C=C1)F)F)C IUJAKAZYMMOLKU-STSQHVNTSA-N 0.000 claims 1
- LSOATWXDIUUFNP-LMNJBCLMSA-N NC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC1=NC2=C(C=CC=C2C=C1)C(=O)N)C=1C=C(C=CC1)C Chemical compound NC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC1=NC2=C(C=CC=C2C=C1)C(=O)N)C=1C=C(C=CC1)C LSOATWXDIUUFNP-LMNJBCLMSA-N 0.000 claims 1
- XOABDUMFRODFCX-GUXCAODWSA-N NC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC=1OC=2C(C1)=C(C=CC2)C(=O)N)C=2C=C(C=CC2)C Chemical compound NC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC=1OC=2C(C1)=C(C=CC2)C(=O)N)C=2C=C(C=CC2)C XOABDUMFRODFCX-GUXCAODWSA-N 0.000 claims 1
- QWIQMOZOUMTIOO-VYDXJSESSA-N NC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC=1OC=2C(N1)=C(C=CC2)C(=O)N)C=2C=C(C=CC2)C Chemical compound NC=1SC(=C(N1)C(=O)N1[C@H]2C[C@H]2C[C@H]1CC=1OC=2C(N1)=C(C=CC2)C(=O)N)C=2C=C(C=CC2)C QWIQMOZOUMTIOO-VYDXJSESSA-N 0.000 claims 1
- CPBFWROPTCKQRA-WEMUQIOZSA-N NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C(C=C2)=CC=C2F)SC(C2CC2)=N1)=O.OC(C1=C(CCO2)C2=CC=C1)=O Chemical compound NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C(C=C2)=CC=C2F)SC(C2CC2)=N1)=O.OC(C1=C(CCO2)C2=CC=C1)=O CPBFWROPTCKQRA-WEMUQIOZSA-N 0.000 claims 1
- GFYMUFIPBDOXGD-LJZXGAKHSA-N NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C(C=CC=C2)=C2F)SC(C2CC2)=N1)=O.OC(C1=C(CCO2)C2=CC=C1)=O Chemical compound NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C(C=CC=C2)=C2F)SC(C2CC2)=N1)=O.OC(C1=C(CCO2)C2=CC=C1)=O GFYMUFIPBDOXGD-LJZXGAKHSA-N 0.000 claims 1
- HDFINNXNBXUKBZ-WEMUQIOZSA-N NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(C(F)(F)F)=CC=C2)SC(C2CC2)=N1)=O.OC(C1=C(CCO2)C2=CC=C1)=O Chemical compound NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(C(F)(F)F)=CC=C2)SC(C2CC2)=N1)=O.OC(C1=C(CCO2)C2=CC=C1)=O HDFINNXNBXUKBZ-WEMUQIOZSA-N 0.000 claims 1
- LRFUREGFYRVYMC-MNRZFKEHSA-N NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O.OC(C1=C(CCO2)C2=CC=C1)=O 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=C(CCO2)C2=CC=C1)=O LRFUREGFYRVYMC-MNRZFKEHSA-N 0.000 claims 1
- GDRABLLGOHPBRB-MNRZFKEHSA-N 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=CC2=C1OCCO2)=O 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=CC2=C1OCCO2)=O GDRABLLGOHPBRB-MNRZFKEHSA-N 0.000 claims 1
- SODKEAAGYYIAQW-MNRZFKEHSA-N NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC(F)=CC=C2)SC(N)=N1)=O.OC(C1=CN=C2SC=CN12)=O 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=CN=C2SC=CN12)=O SODKEAAGYYIAQW-MNRZFKEHSA-N 0.000 claims 1
- QZLLTZQJHKRVBI-DSMRVHDJSA-N NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC=CC=C2)SC(C2CC2)=N1)=O.OC(C1=C(CCO2)C2=CC=C1)=O Chemical compound NC[C@H](C[C@H]1[C@@H]2C1)N2C(C1=C(C2=CC=CC=C2)SC(C2CC2)=N1)=O.OC(C1=C(CCO2)C2=CC=C1)=O QZLLTZQJHKRVBI-DSMRVHDJSA-N 0.000 claims 1
- CBWJEIKESPGRSS-GWCBTUNRSA-N O1C=COC(=C1)C(=O)O.C(C=1CCC=CC1)(=O)NC[C@H]1N([C@H]2C[C@H]2C1)C(=O)C=1N=COC1C1=CC=C(C=C1)OC Chemical compound O1C=COC(=C1)C(=O)O.C(C=1CCC=CC1)(=O)NC[C@H]1N([C@H]2C[C@H]2C1)C(=O)C=1N=COC1C1=CC=C(C=C1)OC CBWJEIKESPGRSS-GWCBTUNRSA-N 0.000 claims 1
- KUQPSYIQZDFGJC-BRJIMVSLSA-N O1COC(=C1)C(=O)O.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 O1COC(=C1)C(=O)O.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 KUQPSYIQZDFGJC-BRJIMVSLSA-N 0.000 claims 1
- NLTXWTRKOFFNNJ-URVXVIKDSA-N O1COC(=C1)C(=O)O.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 O1COC(=C1)C(=O)O.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 NLTXWTRKOFFNNJ-URVXVIKDSA-N 0.000 claims 1
- 108050000742 Orexin Receptor Proteins 0.000 claims 1
- 102000008834 Orexin receptor Human genes 0.000 claims 1
- FSBZNXRGFMRRHR-BRJIMVSLSA-N S1N=NC=C1C(=O)O.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 S1N=NC=C1C(=O)O.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 FSBZNXRGFMRRHR-BRJIMVSLSA-N 0.000 claims 1
- MXVFXNQDFIEKQL-URVXVIKDSA-N S1N=NC=C1C(=O)O.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 S1N=NC=C1C(=O)O.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 MXVFXNQDFIEKQL-URVXVIKDSA-N 0.000 claims 1
- XNWXVWSTVLIVTO-PMPSAXMXSA-N [(1S,3S,5S)-3-(aminomethyl)-2-azabicyclo[3.1.0]hexan-2-yl]-[2-cyclopropyl-5-(4-methylphenyl)-1,3-thiazol-4-yl]methanone Chemical compound C1=CC(C)=CC=C1C1=C(C(=O)N2[C@@H](C[C@@H]3C[C@@H]32)CN)N=C(C2CC2)S1 XNWXVWSTVLIVTO-PMPSAXMXSA-N 0.000 claims 1
- XXDBOFFZWLTRHU-OQNHHKPVSA-N [(1S,3S,5S)-3-(aminomethyl)-2-azabicyclo[3.1.0]hexan-2-yl]-[2-methyl-5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl]methanone 2,3-dihydro-1-benzofuran-4-carboxylic acid Chemical compound CC1=NC(C(N2[C@H](CN)C[C@H]3[C@@H]2C3)=O)=C(C2=CC(C(F)(F)F)=CC=C2)S1.OC(C1=C(CCO2)C2=CC=C1)=O XXDBOFFZWLTRHU-OQNHHKPVSA-N 0.000 claims 1
- WKLZZBMQZBLTMD-DYEKYZERSA-N [(1S,3S,5S)-3-(aminomethyl)-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)CN)=C1 WKLZZBMQZBLTMD-DYEKYZERSA-N 0.000 claims 1
- WKNVZILAWZTZGS-AGIUHOORSA-N [(1s,3s,5s)-3-(aminomethyl)-2-azabicyclo[3.1.0]hexan-2-yl]-[2-amino-5-(3-methylphenyl)-1,3-thiazol-4-yl]methanone Chemical compound CC1=CC=CC(C2=C(N=C(N)S2)C(=O)N2[C@@H](C[C@@H]3C[C@@H]32)CN)=C1 WKNVZILAWZTZGS-AGIUHOORSA-N 0.000 claims 1
- 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
- VXSMUGJLHVKIPB-PVAVHDDUSA-N [(1s,3s,5s)-3-[[(5-bromopyrimidin-2-yl)amino]methyl]-2-azabicyclo[3.1.0]hexan-2-yl]-(2-methyl-5-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=CC=CC=1)C)NC1=NC=C(Br)C=N1 VXSMUGJLHVKIPB-PVAVHDDUSA-N 0.000 claims 1
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- 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
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- 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
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
-
- 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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Psychiatry (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Pulmonology (AREA)
- Obesity (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Addiction (AREA)
- Emergency Medicine (AREA)
- Psychology (AREA)
- Anesthesiology (AREA)
- Reproductive Health (AREA)
- Otolaryngology (AREA)
- Dermatology (AREA)
- Immunology (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IB2006055042 | 2006-12-28 | ||
| IBPCT/IB2006/055042 | 2006-12-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2009128739A RU2009128739A (ru) | 2011-02-10 |
| RU2460732C2 true RU2460732C2 (ru) | 2012-09-10 |
Family
ID=39343649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2009128739/04A RU2460732C2 (ru) | 2006-12-28 | 2007-12-28 | Производные 2-аза-бицикло[3.1.0.]гексана в качестве антагонистов рецептора орексина |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US8288435B2 (en:Method) |
| EP (1) | EP2094690B1 (en:Method) |
| JP (1) | JP2010514751A (en:Method) |
| KR (1) | KR20090094168A (en:Method) |
| CN (1) | CN101568536B (en:Method) |
| AR (1) | AR064561A1 (en:Method) |
| AT (1) | ATE505467T1 (en:Method) |
| AU (1) | AU2007340944B2 (en:Method) |
| BR (1) | BRPI0720876A2 (en:Method) |
| CA (1) | CA2669821A1 (en:Method) |
| CL (1) | CL2007003827A1 (en:Method) |
| CY (1) | CY1111705T1 (en:Method) |
| DE (1) | DE602007013937D1 (en:Method) |
| DK (1) | DK2094690T3 (en:Method) |
| ES (1) | ES2364297T3 (en:Method) |
| HR (1) | HRP20110509T1 (en:Method) |
| MA (1) | MA31000B1 (en:Method) |
| MX (1) | MX2009006860A (en:Method) |
| MY (1) | MY157344A (en:Method) |
| NO (1) | NO20092762L (en:Method) |
| NZ (1) | NZ578642A (en:Method) |
| PL (1) | PL2094690T3 (en:Method) |
| PT (1) | PT2094690E (en:Method) |
| RU (1) | RU2460732C2 (en:Method) |
| SI (1) | SI2094690T1 (en:Method) |
| TW (1) | TW200833328A (en:Method) |
| WO (1) | WO2008081399A2 (en:Method) |
| ZA (1) | ZA200905229B (en:Method) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008038251A2 (en) * | 2006-09-29 | 2008-04-03 | Actelion Pharmaceuticals Ltd | 3-aza-bicyclo[3.1.0]hexane derivatives |
| US8133901B2 (en) | 2006-12-01 | 2012-03-13 | Actelion Pharmaceuticals Ltd. | 3-heteroaryl (amino or amido)-1-(biphenyl or phenylthiazolyl) carbonylpiperidine derivatives as 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. |
| WO2008150364A1 (en) | 2007-05-23 | 2008-12-11 | Merck & Co., Inc. | Cyclopropyl pyrrolidine orexin receptor antagonists |
| JP2010540429A (ja) * | 2007-09-24 | 2010-12-24 | アクテリオン ファーマシューティカルズ リミテッド | オレキシン受容体拮抗薬としてのピロリジン類及びピペリジン類 |
| WO2009104155A1 (en) * | 2008-02-21 | 2009-08-27 | Actelion Pharmaceuticals Ltd | 2-aza-bicyclo[2.2.1]heptane derivatives |
| WO2009133522A1 (en) * | 2008-04-30 | 2009-11-05 | Actelion Pharmaceuticals Ltd | Piperidine and pyrrolidine compounds |
| WO2010044054A1 (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 |
| DK2519514T3 (en) * | 2009-12-29 | 2015-11-16 | Suven Life Sciences Ltd | Neuronal nicotinic alpha4beta2-acetylcholine receptor ligands |
| US8268848B2 (en) * | 2010-09-22 | 2012-09-18 | Eisai R&D Management Co., Ltd. | Cyclopropane compound |
| 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 |
| US9440982B2 (en) | 2012-02-07 | 2016-09-13 | Eolas Therapeutics, Inc. | Substituted prolines/piperidines as orexin receptor antagonists |
| BR112014019426A8 (pt) | 2012-02-07 | 2017-07-11 | Eolas Therapeutics Inc | Prolinas/ piperidinas substituídas como antagonistas do receptor de orexina |
| ITMI20120424A1 (it) * | 2012-03-19 | 2013-09-20 | Rottapharm Spa | Composti chimici |
| TWI510481B (zh) * | 2012-06-04 | 2015-12-01 | Actelion Pharmaceuticals Ltd | 苯并咪唑脯胺酸衍生物 |
| AU2013292529A1 (en) | 2012-07-18 | 2015-02-12 | Marvin J. Miller | 5,5-heteroaromatic anti-infective compounds |
| MX2015004638A (es) | 2012-10-10 | 2015-07-14 | Actelion Pharmaceuticals Ltd | Antagonistas de receptores de orexina los cuales son derivados de [orto bi-(hetero-) aril]-[2-meta bi-(hetero-) aril)-pirrolidin-1-il]-metanona. |
| JP2016510810A (ja) | 2013-03-12 | 2016-04-11 | アクテリオン ファーマシューティカルズ リミテッドＡｃｔｅｌｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | オレキシン受容体アンタゴニストとしてのアゼチジンアミド誘導体 |
| 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 |
| 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 |
| 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 |
| HUE035731T2 (hu) | 2013-12-03 | 2018-05-28 | Idorsia Pharmaceuticals Ltd | (S)-(2-(6-klór-7-metil-1H-benzo[d]imidazol-2-il)-2-metilpirrolidin-1-il)(5-metoxi-2- (2H-l,2,3-triazol-2-il)fenil)metanon kristályos formája és alkalmazása orexin receptor antagonistaként |
| 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 |
| LT3077391T (lt) | 2013-12-04 | 2018-10-25 | Idorsia Pharmaceuticals Ltd | Benzimidazolo prolino darinių panaudojimas |
| TW201613864A (en) | 2014-02-20 | 2016-04-16 | Takeda Pharmaceutical | Novel compounds |
| AR101558A1 (es) | 2014-08-13 | 2016-12-28 | Eolas Therapeutics Inc | Difluoropirrolidinas como moduladores del receptor de orexina |
| KR102455043B1 (ko) | 2014-09-11 | 2022-10-13 | 얀센 파마슈티카 엔.브이. | 치환된 2-아자바이사이클 및 오렉신 수용체 조절제로서의 이의 용도 |
| CN107810006B (zh) | 2014-10-23 | 2021-03-30 | 卫材R&D管理有限公司 | 用于治疗失眠的组合物 |
| 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 |
| AU2017217931B2 (en) | 2016-02-12 | 2020-10-22 | Astrazeneca Ab | Halo-substituted piperidines as orexin receptor modulators |
| KR20180115743A (ko) * | 2016-02-26 | 2018-10-23 | 지앙수 헨그루이 메디슨 컴퍼니 리미티드 | 신규 독소, 및 이의 중간체를 제조하는 방법 |
| 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 |
| CN110612291B (zh) | 2017-05-03 | 2024-02-13 | 爱杜西亚药品有限公司 | 2-([1,2,3]三唑-2-基)-苯甲酸衍生物的制备 |
| 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 |
| MX2023001818A (es) | 2020-08-13 | 2023-03-13 | Boehringer Ingelheim Int | Compuestos para usarse en tratamiento de deterioro cognitivo asociado con la esquizofrenia. |
| AU2021360172A1 (en) | 2020-10-13 | 2023-03-30 | 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 |
| WO2023218023A1 (en) | 2022-05-13 | 2023-11-16 | Idorsia Pharmaceuticals Ltd | Thiazoloaryl-methyl substituted cyclic hydrazine-n-carboxamide derivatives |
| WO2025224168A1 (en) | 2024-04-24 | 2025-10-30 | Idorsia Pharmaceuticals Ltd | Aryl sulfone and sulfanone derivatives as orexin receptor modulators |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001096302A1 (en) * | 2000-06-16 | 2001-12-20 | Smithkline Beecham P.L.C. | Piperidines for use as orexin receptor antagonists |
| WO2002089800A2 (en) * | 2001-05-05 | 2002-11-14 | Smithkline Beecham P.L.C. | N-aroyl cyclic amine derivatives as orexin receptor antagonists |
| WO2003002561A1 (en) * | 2001-06-28 | 2003-01-09 | Smithkline Beecham P.L.C. | N-aroyl cyclic amine derivatives as orexin receptor antagonists |
| WO2003041711A1 (en) * | 2001-11-10 | 2003-05-22 | Smithkline Beecham P.L.C. | Piperazine bis-amide derivatives and their use as antagonists of the orexin receptor |
| WO2003051368A1 (en) * | 2001-12-19 | 2003-06-26 | Smithkline Beecham Plc | N-aroyl cyclic amine derivatives as orexin receptor antagonists |
| WO2003051873A1 (en) * | 2001-12-19 | 2003-06-26 | Smithkline Beecham Plc | Piperazine compounds and their phamaceutical use |
| WO2004026866A1 (en) * | 2002-09-18 | 2004-04-01 | Glaxo Group Limited | N-aroyl cyclic amines as orexin receptor antagonists |
| WO2004041816A1 (en) * | 2002-11-06 | 2004-05-21 | Glaxo Group Limited | Azacyclic compounds as orexin receptor antagonist |
| WO2004041791A1 (en) * | 2002-11-06 | 2004-05-21 | Glaxo Group Limited | N-aryl acetyl cyclic amine derivatives as orexin antagonists |
| RU2004121166A (ru) * | 2001-12-10 | 2005-05-10 | Ф.Хоффманн-Ля Рош Аг (Ch) | 2-аминобензотиазолилмочевины в качестве модуляторов аденозина |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH621126A5 (en:Method) | 1974-02-07 | 1981-01-15 | Plantex Ltd | |
| AU2381995A (en) | 1994-04-29 | 1995-11-29 | Pharmacia & Upjohn Company | Methanol derivatives for treatment of retroviral infections especially hiv infections |
| JP2004533989A (ja) | 2000-11-20 | 2004-11-11 | サイオス インコーポレイテッド | ｐ３８キナーゼのピペリジン／ピペラジン型阻害剤 |
| DE60108420T2 (de) | 2000-11-28 | 2005-12-22 | Smithkline Beecham P.L.C., Brentford | Morpholinderivate als antagonisten an orexinrezeptoren |
| ATE383359T1 (de) * | 2001-05-05 | 2008-01-15 | Smithkline Beecham Plc | N-aroyl zyklische amine |
| GB0111341D0 (en) | 2001-05-10 | 2001-07-04 | Bp Chem Int Ltd | Novel polymerisation catalysts |
| GB0115862D0 (en) * | 2001-06-28 | 2001-08-22 | Smithkline Beecham Plc | Compounds |
| GB0124463D0 (en) | 2001-10-11 | 2001-12-05 | Smithkline Beecham Plc | Compounds |
| US6995144B2 (en) | 2002-03-14 | 2006-02-07 | Eisai Co., Ltd. | Nitrogen containing heterocyclic compounds and medicines containing the same |
| GB0225938D0 (en) | 2002-11-06 | 2002-12-11 | Glaxo Group Ltd | Novel compounds |
| ES2327737T3 (es) * | 2003-03-26 | 2009-11-03 | Actelion Pharmaceuticals Ltd. | Derivados de tetrahidroisoquinolil acetamida para uso como antagonistas de receptores de orexina. |
| WO2004096780A1 (en) * | 2003-04-28 | 2004-11-11 | Actelion Pharmaceuticals Ltd | Quinoxalinone-3- one derivatives as orexin receptor antagonists |
| HRP20150371T1 (hr) * | 2004-03-01 | 2015-05-08 | Actelion Pharmaceuticals Ltd. | Supstituirani derivati 1,2,3,4-tetrahidroizokinolina |
| US20060014733A1 (en) * | 2004-07-19 | 2006-01-19 | Pfizer Inc | Histamine-3 agonists and antagonists |
| US7994336B2 (en) * | 2006-08-15 | 2011-08-09 | Actelion Pharmaceuticals Ltd. | Azetidine compounds as orexin receptor antagonists |
| WO2008038251A2 (en) * | 2006-09-29 | 2008-04-03 | Actelion Pharmaceuticals Ltd | 3-aza-bicyclo[3.1.0]hexane derivatives |
| US8133901B2 (en) * | 2006-12-01 | 2012-03-13 | Actelion Pharmaceuticals Ltd. | 3-heteroaryl (amino or amido)-1-(biphenyl or phenylthiazolyl) carbonylpiperidine derivatives as 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. |
| US20100222328A1 (en) * | 2007-05-14 | 2010-09-02 | Hamed Aissaoui | 2-cyclopropyl-thiazole derivatives |
| WO2008150364A1 (en) | 2007-05-23 | 2008-12-11 | Merck & Co., Inc. | Cyclopropyl pyrrolidine orexin receptor antagonists |
| CN101679366B (zh) | 2007-05-23 | 2013-08-07 | 默沙东公司 | 吡啶基哌啶食欲素受体拮抗剂 |
| AU2008272449A1 (en) | 2007-07-03 | 2009-01-08 | Actelion Pharmaceuticals Ltd | 3-aza-bicyclo[3.3.0]octane compounds |
| AR067665A1 (es) | 2007-07-27 | 2009-10-21 | Actelion Pharmaceuticals Ltd | Derivados de trans-3- aza-biciclo ( 3.1.0) hexano |
| NZ583487A (en) * | 2007-07-27 | 2011-09-30 | Actelion Pharmaceuticals Ltd | 2-aza-bicyclo[3.3.0]octane derivatives |
| JP2010540429A (ja) * | 2007-09-24 | 2010-12-24 | アクテリオン ファーマシューティカルズ リミテッド | オレキシン受容体拮抗薬としてのピロリジン類及びピペリジン類 |
| WO2009104155A1 (en) * | 2008-02-21 | 2009-08-27 | Actelion Pharmaceuticals Ltd | 2-aza-bicyclo[2.2.1]heptane derivatives |
| WO2009133522A1 (en) * | 2008-04-30 | 2009-11-05 | Actelion Pharmaceuticals Ltd | Piperidine and pyrrolidine compounds |
| TW200940822A (en) * | 2009-05-07 | 2009-10-01 | Wan Chi Steel Ind Co Ltd | Water wheel mechanism with sun-and-planet type blade |
-
2007
- 2007-12-27 AR ARP070105930A patent/AR064561A1/es not_active Application Discontinuation
- 2007-12-27 TW TW096150631A patent/TW200833328A/zh unknown
- 2007-12-27 CL CL200703827A patent/CL2007003827A1/es unknown
- 2007-12-28 US US12/521,453 patent/US8288435B2/en not_active Expired - Fee Related
- 2007-12-28 BR BRPI0720876-6A patent/BRPI0720876A2/pt not_active IP Right Cessation
- 2007-12-28 WO PCT/IB2007/055326 patent/WO2008081399A2/en not_active Ceased
- 2007-12-28 ES ES07859531T patent/ES2364297T3/es active Active
- 2007-12-28 CA CA002669821A patent/CA2669821A1/en not_active Abandoned
- 2007-12-28 AU AU2007340944A patent/AU2007340944B2/en not_active Expired - Fee Related
- 2007-12-28 MY MYPI20092751A patent/MY157344A/en unknown
- 2007-12-28 PT PT07859531T patent/PT2094690E/pt unknown
- 2007-12-28 MX MX2009006860A patent/MX2009006860A/es active IP Right Grant
- 2007-12-28 AT AT07859531T patent/ATE505467T1/de active
- 2007-12-28 DE DE602007013937T patent/DE602007013937D1/de active Active
- 2007-12-28 JP JP2009543566A patent/JP2010514751A/ja active Pending
- 2007-12-28 PL PL07859531T patent/PL2094690T3/pl unknown
- 2007-12-28 DK DK07859531.1T patent/DK2094690T3/da active
- 2007-12-28 EP EP07859531A patent/EP2094690B1/en not_active Not-in-force
- 2007-12-28 RU RU2009128739/04A patent/RU2460732C2/ru not_active IP Right Cessation
- 2007-12-28 KR KR1020097015732A patent/KR20090094168A/ko not_active Ceased
- 2007-12-28 SI SI200730639T patent/SI2094690T1/sl unknown
- 2007-12-28 CN CN2007800483236A patent/CN101568536B/zh not_active Expired - Fee Related
- 2007-12-28 HR HR20110509T patent/HRP20110509T1/hr unknown
- 2007-12-28 NZ NZ578642A patent/NZ578642A/en not_active IP Right Cessation
-
2009
- 2009-06-17 MA MA32004A patent/MA31000B1/fr unknown
- 2009-07-27 ZA ZA200905229A patent/ZA200905229B/xx unknown
- 2009-07-27 NO NO20092762A patent/NO20092762L/no not_active Application Discontinuation
-
2011
- 2011-07-13 CY CY20111100681T patent/CY1111705T1/el unknown
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001096302A1 (en) * | 2000-06-16 | 2001-12-20 | Smithkline Beecham P.L.C. | Piperidines for use as orexin receptor antagonists |
| WO2002089800A2 (en) * | 2001-05-05 | 2002-11-14 | Smithkline Beecham P.L.C. | N-aroyl cyclic amine derivatives as orexin receptor antagonists |
| WO2003002561A1 (en) * | 2001-06-28 | 2003-01-09 | Smithkline Beecham P.L.C. | N-aroyl cyclic amine derivatives as orexin receptor antagonists |
| WO2003041711A1 (en) * | 2001-11-10 | 2003-05-22 | Smithkline Beecham P.L.C. | Piperazine bis-amide derivatives and their use as antagonists of the orexin receptor |
| RU2004121166A (ru) * | 2001-12-10 | 2005-05-10 | Ф.Хоффманн-Ля Рош Аг (Ch) | 2-аминобензотиазолилмочевины в качестве модуляторов аденозина |
| WO2003051368A1 (en) * | 2001-12-19 | 2003-06-26 | Smithkline Beecham Plc | N-aroyl cyclic amine derivatives as orexin receptor antagonists |
| WO2003051873A1 (en) * | 2001-12-19 | 2003-06-26 | Smithkline Beecham Plc | Piperazine compounds and their phamaceutical use |
| WO2004026866A1 (en) * | 2002-09-18 | 2004-04-01 | Glaxo Group Limited | N-aroyl cyclic amines as orexin receptor antagonists |
| WO2004041816A1 (en) * | 2002-11-06 | 2004-05-21 | Glaxo Group Limited | Azacyclic compounds as orexin receptor antagonist |
| WO2004041791A1 (en) * | 2002-11-06 | 2004-05-21 | Glaxo Group Limited | N-aryl acetyl cyclic amine derivatives as orexin antagonists |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2460732C2 (ru) | Производные 2-аза-бицикло[3.1.0.]гексана в качестве антагонистов рецептора орексина | |
| RU2010138640A (ru) | Производные 2-аза-бицикло [2.2.1] гептана | |
| RU2447070C2 (ru) | Соединения азетидина в качестве антагонистов рецептора орексина | |
| ES2350460T3 (es) | Derivados de 3-aza-biciclo[3.1.0]hexano. | |
| RU2435757C2 (ru) | Производные 3-циклил-2-(4-сульфамоилфенил)-n-циклилпропионамида, применимые для лечения нарушенной переносимости глюкозы и диабета | |
| EP2185512B1 (en) | Trans-3-aza-bicyclo[3.1.0]hexane derivatives | |
| JP5412429B2 (ja) | 抗細菌性アミド及びスルホンアミド置換複素環式尿素化合物 | |
| RU2010106854A (ru) | Производные 2-аза-бицикло[3.3.0]октана | |
| US8063099B2 (en) | Trans-3-aza-bicyclo[3.1.0]hexane derivatives | |
| EP2841437A1 (en) | Imidazothiadiazole and imidazopyrazine derivatives as protease activated receptor 4 (par4) inhibitors for treating platelet aggregation | |
| JP2003523389A (ja) | チロシンキナーゼ阻害薬 | |
| US20110105491A1 (en) | Thiazolidine compounds as orexin receptor antagonists | |
| AU2008272449A1 (en) | 3-aza-bicyclo[3.3.0]octane compounds | |
| JP2003523390A (ja) | チロシンキナーゼ阻害薬 | |
| AU2015212495A1 (en) | Antibacterial combinations comprising polymyxin | |
| RU2471796C2 (ru) | Соединения 3-аза-бицикло[3.3.0]октана | |
| HK1136554B (en) | 2-aza-bicyclo[3.1.0]hexane derivatives as orexin receptor antagonists |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20131229 |