JP2006522797A5 - - Google Patents
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- Publication number
- JP2006522797A5 JP2006522797A5 JP2006506512A JP2006506512A JP2006522797A5 JP 2006522797 A5 JP2006522797 A5 JP 2006522797A5 JP 2006506512 A JP2006506512 A JP 2006506512A JP 2006506512 A JP2006506512 A JP 2006506512A JP 2006522797 A5 JP2006522797 A5 JP 2006522797A5
- Authority
- JP
- Japan
- Prior art keywords
- aza
- bicyclo
- phenyl
- ylmethyl
- methoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 21
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 6
- -1 1, 2, 3, 4-tetrahydronaphth-2-yl Chemical group 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims 1
- KEFAFGCJUBWJQM-UHFFFAOYSA-N 2-methoxy-n-[3-(2-octyl-2-azabicyclo[3.3.1]nonan-5-yl)phenyl]ethanesulfonamide Chemical compound C1CCC(C2)N(CCCCCCCC)CCC21C1=CC=CC(NS(=O)(=O)CCOC)=C1 KEFAFGCJUBWJQM-UHFFFAOYSA-N 0.000 claims 1
- QIEIPAYLELIUPS-UHFFFAOYSA-N 2-methoxy-n-[3-[2-(1,2,3,4-tetrahydronaphthalen-2-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC2CC4=CC=CC=C4CC2)CC3)=C1 QIEIPAYLELIUPS-UHFFFAOYSA-N 0.000 claims 1
- RAHJKXJBOHVWON-UHFFFAOYSA-N 2-methoxy-n-[3-[2-(1,3-thiazol-2-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC=2SC=CN=2)CC3)=C1 RAHJKXJBOHVWON-UHFFFAOYSA-N 0.000 claims 1
- INCJRISTJIRWIA-UHFFFAOYSA-N 2-methoxy-n-[3-[2-(1h-pyrrol-2-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC=2NC=CC=2)CC3)=C1 INCJRISTJIRWIA-UHFFFAOYSA-N 0.000 claims 1
- BSXVWUGGGVSRPU-UHFFFAOYSA-N 2-methoxy-n-[3-[2-(2-methylpropyl)-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC(C)C)CC3)=C1 BSXVWUGGGVSRPU-UHFFFAOYSA-N 0.000 claims 1
- KYDPDURBBFOTGL-UHFFFAOYSA-N 2-methoxy-n-[3-[2-(3-methylbutyl)-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CCC(C)C)CC3)=C1 KYDPDURBBFOTGL-UHFFFAOYSA-N 0.000 claims 1
- RAGZCCWCXWQVQA-UHFFFAOYSA-N 2-methoxy-n-[3-[2-(3-phenylprop-2-ynyl)-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC#CC=2C=CC=CC=2)CC3)=C1 RAGZCCWCXWQVQA-UHFFFAOYSA-N 0.000 claims 1
- CRNFTHNQOFPKAE-UHFFFAOYSA-N 2-methoxy-n-[3-[2-(3-phenylpropyl)-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CCCC=2C=CC=CC=2)CC3)=C1 CRNFTHNQOFPKAE-UHFFFAOYSA-N 0.000 claims 1
- PEHWNAOBXAQSGD-UHFFFAOYSA-N 2-methoxy-n-[3-[2-(naphthalen-1-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC=2C4=CC=CC=C4C=CC=2)CC3)=C1 PEHWNAOBXAQSGD-UHFFFAOYSA-N 0.000 claims 1
- ZPDSUULKMSIGFF-UHFFFAOYSA-N 2-methoxy-n-[3-[2-(naphthalen-2-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC=2C=C4C=CC=CC4=CC=2)CC3)=C1 ZPDSUULKMSIGFF-UHFFFAOYSA-N 0.000 claims 1
- FIZJKAQUTMKZLX-UHFFFAOYSA-N 2-methoxy-n-[3-[2-(quinolin-3-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC=2C=C4C=CC=CC4=NC=2)CC3)=C1 FIZJKAQUTMKZLX-UHFFFAOYSA-N 0.000 claims 1
- WAMMKGNBMZTUER-UHFFFAOYSA-N 2-methoxy-n-[3-[2-(quinolin-4-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC=2C4=CC=CC=C4N=CC=2)CC3)=C1 WAMMKGNBMZTUER-UHFFFAOYSA-N 0.000 claims 1
- FRWSCDHYSIEEDU-UHFFFAOYSA-N 2-methoxy-n-[3-[2-(thiophen-3-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC2=CSC=C2)CC3)=C1 FRWSCDHYSIEEDU-UHFFFAOYSA-N 0.000 claims 1
- ZJGIAPBKSHGFBY-UHFFFAOYSA-N 2-methoxy-n-[3-[2-[(3-methyl-1-benzothiophen-2-yl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC2=C(C4=CC=CC=C4S2)C)CC3)=C1 ZJGIAPBKSHGFBY-UHFFFAOYSA-N 0.000 claims 1
- FVERCTPSPDKRGT-UHFFFAOYSA-N 2-methoxy-n-[3-[2-[(3-phenoxyphenyl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC=2C=C(OC=4C=CC=CC=4)C=CC=2)CC3)=C1 FVERCTPSPDKRGT-UHFFFAOYSA-N 0.000 claims 1
- XDOUPWOTGANRGP-UHFFFAOYSA-N 2-methoxy-n-[3-[2-[(3-phenylcyclobutyl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC2CC(C2)C=2C=CC=CC=2)CC3)=C1 XDOUPWOTGANRGP-UHFFFAOYSA-N 0.000 claims 1
- ZQVNKBCHVAFILS-UHFFFAOYSA-N 2-methoxy-n-[3-[2-[(4-methoxyphenyl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC=2C=CC(OC)=CC=2)CC3)=C1 ZQVNKBCHVAFILS-UHFFFAOYSA-N 0.000 claims 1
- ZDUCGFHPYUYCHY-UHFFFAOYSA-N 2-methoxy-n-[3-[2-[(4-phenylphenyl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC=2C=CC(=CC=2)C=2C=CC=CC=2)CC3)=C1 ZDUCGFHPYUYCHY-UHFFFAOYSA-N 0.000 claims 1
- GFMVUCDZLXKXME-UHFFFAOYSA-N 2-methoxy-n-[3-[2-[(4-pyrrolidin-1-ylphenyl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC=2C=CC(=CC=2)N2CCCC2)CC3)=C1 GFMVUCDZLXKXME-UHFFFAOYSA-N 0.000 claims 1
- IEQAJUDRSHWPNL-UHFFFAOYSA-N 2-methoxy-n-[3-[2-[2-(2-phenylethoxy)ethyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CCOCCC=2C=CC=CC=2)CC3)=C1 IEQAJUDRSHWPNL-UHFFFAOYSA-N 0.000 claims 1
- NZBQWJKJPHADLR-UHFFFAOYSA-N 2-methoxy-n-[3-[2-[[3-(trifluoromethoxy)phenyl]methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]ethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC=2C=C(OC(F)(F)F)C=CC=2)CC3)=C1 NZBQWJKJPHADLR-UHFFFAOYSA-N 0.000 claims 1
- FPKXGCIJMWWBNN-UHFFFAOYSA-N 3-(2-ethyl-2-azabicyclo[3.3.1]nonan-5-yl)benzamide Chemical compound C1CCC(C2)N(CC)CCC21C1=CC=CC(C(N)=O)=C1 FPKXGCIJMWWBNN-UHFFFAOYSA-N 0.000 claims 1
- FAXPVZGLOQZLOH-UHFFFAOYSA-N 3-(2-heptyl-2-azabicyclo[3.3.1]nonan-5-yl)benzamide Chemical compound C1CCC(C2)N(CCCCCCC)CCC21C1=CC=CC(C(N)=O)=C1 FAXPVZGLOQZLOH-UHFFFAOYSA-N 0.000 claims 1
- XPGCJFGOPKCGOQ-UHFFFAOYSA-N 3-(2-hexyl-2-azabicyclo[3.3.1]nonan-5-yl)benzamide Chemical compound C1CCC(C2)N(CCCCCC)CCC21C1=CC=CC(C(N)=O)=C1 XPGCJFGOPKCGOQ-UHFFFAOYSA-N 0.000 claims 1
- JGGREPVKZAEUHL-UHFFFAOYSA-N 3-(2-octyl-2-azabicyclo[3.3.1]nonan-5-yl)benzamide Chemical compound C1CCC(C2)N(CCCCCCCC)CCC21C1=CC=CC(C(N)=O)=C1 JGGREPVKZAEUHL-UHFFFAOYSA-N 0.000 claims 1
- ZMMUWJKQJQCWAR-UHFFFAOYSA-N 3-(2-pentyl-2-azabicyclo[3.3.1]nonan-5-yl)benzamide Chemical compound C1CCC(C2)N(CCCCC)CCC21C1=CC=CC(C(N)=O)=C1 ZMMUWJKQJQCWAR-UHFFFAOYSA-N 0.000 claims 1
- GTBCLXHEOGYOGI-UHFFFAOYSA-N 3-[1-(2-phenylethyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound C1(=CC=CC=C1)CCC12NCCC(CCC1)(C2)C=1C=C(C(=O)N)C=CC=1 GTBCLXHEOGYOGI-UHFFFAOYSA-N 0.000 claims 1
- RZMXZLQPEFQXCN-UHFFFAOYSA-N 3-[2-(1,2,3,4-tetrahydronaphthalen-2-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC2CC4=CC=CC=C4CC2)CC3)=C1 RZMXZLQPEFQXCN-UHFFFAOYSA-N 0.000 claims 1
- FUGKCDKDPZOJPQ-UHFFFAOYSA-N 3-[2-(1,3-thiazol-2-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC=2SC=CN=2)CC3)=C1 FUGKCDKDPZOJPQ-UHFFFAOYSA-N 0.000 claims 1
- KDRPPPDGLGSSNN-UHFFFAOYSA-N 3-[2-(1-benzofuran-2-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC=2OC4=CC=CC=C4C=2)CC3)=C1 KDRPPPDGLGSSNN-UHFFFAOYSA-N 0.000 claims 1
- WBEMIDHTHGUGLN-UHFFFAOYSA-N 3-[2-(1h-imidazol-2-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC=2NC=CN=2)CC3)=C1 WBEMIDHTHGUGLN-UHFFFAOYSA-N 0.000 claims 1
- PUOOQBLMNRELHE-UHFFFAOYSA-N 3-[2-(1h-indol-3-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC=2C4=CC=CC=C4NC=2)CC3)=C1 PUOOQBLMNRELHE-UHFFFAOYSA-N 0.000 claims 1
- VIONGUQMNGHWMU-UHFFFAOYSA-N 3-[2-(1h-pyrrol-2-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC=2NC=CC=2)CC3)=C1 VIONGUQMNGHWMU-UHFFFAOYSA-N 0.000 claims 1
- VZJULWOZMWZEMO-UHFFFAOYSA-N 3-[2-(2,3-dihydro-1h-inden-2-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC2CC4=CC=CC=C4C2)CC3)=C1 VZJULWOZMWZEMO-UHFFFAOYSA-N 0.000 claims 1
- JPFOLYPWCBPQSJ-UHFFFAOYSA-N 3-[2-(2-ethylbutyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound C1CCC(C2)N(CC(CC)CC)CCC21C1=CC=CC(C(N)=O)=C1 JPFOLYPWCBPQSJ-UHFFFAOYSA-N 0.000 claims 1
- DMCNBZBVMCDBKN-UHFFFAOYSA-N 3-[2-(2-ethylhexyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound C1CCC(C2)N(CC(CC)CCCC)CCC21C1=CC=CC(C(N)=O)=C1 DMCNBZBVMCDBKN-UHFFFAOYSA-N 0.000 claims 1
- WSHDVGRJIFWABO-UHFFFAOYSA-N 3-[2-(2-methylpropyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound C1CCC(C2)N(CC(C)C)CCC21C1=CC=CC(C(N)=O)=C1 WSHDVGRJIFWABO-UHFFFAOYSA-N 0.000 claims 1
- HEMDHIHNLTWTPL-UHFFFAOYSA-N 3-[2-(3-cyclohexylpropyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CCCC2CCCCC2)CC3)=C1 HEMDHIHNLTWTPL-UHFFFAOYSA-N 0.000 claims 1
- BYQWNNOWNIQGLL-UHFFFAOYSA-N 3-[2-(3-cyclopentylpropyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CCCC2CCCC2)CC3)=C1 BYQWNNOWNIQGLL-UHFFFAOYSA-N 0.000 claims 1
- VXVNSRQJWGEWTA-UHFFFAOYSA-N 3-[2-(3-methylbutyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound C1CCC(C2)N(CCC(C)C)CCC21C1=CC=CC(C(N)=O)=C1 VXVNSRQJWGEWTA-UHFFFAOYSA-N 0.000 claims 1
- YJDSJINCBKULSF-UHFFFAOYSA-N 3-[2-(3-phenylprop-2-ynyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC#CC=2C=CC=CC=2)CC3)=C1 YJDSJINCBKULSF-UHFFFAOYSA-N 0.000 claims 1
- SQVBTOBQXXNQLI-UHFFFAOYSA-N 3-[2-(3-phenylpropyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CCCC=2C=CC=CC=2)CC3)=C1 SQVBTOBQXXNQLI-UHFFFAOYSA-N 0.000 claims 1
- BVEZPMSUZPKAQO-UHFFFAOYSA-N 3-[2-(9h-fluoren-2-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC=2C=C4C(C5=CC=CC=C5C4)=CC=2)CC3)=C1 BVEZPMSUZPKAQO-UHFFFAOYSA-N 0.000 claims 1
- YYKPKDVDDDHICQ-UHFFFAOYSA-N 3-[2-(cyclopropylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC2CC2)CC3)=C1 YYKPKDVDDDHICQ-UHFFFAOYSA-N 0.000 claims 1
- LTARZFLOOWJRJZ-UHFFFAOYSA-N 3-[2-(naphthalen-1-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC=2C4=CC=CC=C4C=CC=2)CC3)=C1 LTARZFLOOWJRJZ-UHFFFAOYSA-N 0.000 claims 1
- FZRBKBAUVAOJCS-UHFFFAOYSA-N 3-[2-(naphthalen-2-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC=2C=C4C=CC=CC4=CC=2)CC3)=C1 FZRBKBAUVAOJCS-UHFFFAOYSA-N 0.000 claims 1
- CQOHTADEAPLGJU-UHFFFAOYSA-N 3-[2-(quinolin-3-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC=2C=C4C=CC=CC4=NC=2)CC3)=C1 CQOHTADEAPLGJU-UHFFFAOYSA-N 0.000 claims 1
- QANJPOFITDFVAF-UHFFFAOYSA-N 3-[2-(quinolin-4-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC=2C4=CC=CC=C4N=CC=2)CC3)=C1 QANJPOFITDFVAF-UHFFFAOYSA-N 0.000 claims 1
- KFONPCSQQXFPGZ-UHFFFAOYSA-N 3-[2-(thiophen-3-ylmethyl)-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC2=CSC=C2)CC3)=C1 KFONPCSQQXFPGZ-UHFFFAOYSA-N 0.000 claims 1
- ZDNOWEMLEUNNNV-UHFFFAOYSA-N 3-[2-[(1-hydroxycyclobutyl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC2(O)CCC2)CC3)=C1 ZDNOWEMLEUNNNV-UHFFFAOYSA-N 0.000 claims 1
- UCXJNVUJMZSKQP-UHFFFAOYSA-N 3-[2-[(1-methylindol-3-yl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound C12=CC=CC=C2N(C)C=C1CN(C(CCC1)C2)CCC21C1=CC=CC(C(N)=O)=C1 UCXJNVUJMZSKQP-UHFFFAOYSA-N 0.000 claims 1
- VDFMRKLOHOHSJJ-UHFFFAOYSA-N 3-[2-[(1-methylpyrrol-2-yl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound CN1C=CC=C1CN1C(C2)CCCC2(C=2C=C(C=CC=2)C(N)=O)CC1 VDFMRKLOHOHSJJ-UHFFFAOYSA-N 0.000 claims 1
- XWJBBHRGYQANKK-UHFFFAOYSA-N 3-[2-[(2-hydroxy-1,3-dihydroinden-2-yl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC2(O)CC4=CC=CC=C4C2)CC3)=C1 XWJBBHRGYQANKK-UHFFFAOYSA-N 0.000 claims 1
- ZCDWSEYWBPLIPE-UHFFFAOYSA-N 3-[2-[(2-hydroxy-3,4-dihydro-1h-naphthalen-2-yl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC2(O)CC4=CC=CC=C4CC2)CC3)=C1 ZCDWSEYWBPLIPE-UHFFFAOYSA-N 0.000 claims 1
- KVYKNPRAOIPRSJ-UHFFFAOYSA-N 3-[2-[(3-methyl-1-benzothiophen-2-yl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound S1C2=CC=CC=C2C(C)=C1CN(C(CCC1)C2)CCC21C1=CC=CC(C(N)=O)=C1 KVYKNPRAOIPRSJ-UHFFFAOYSA-N 0.000 claims 1
- WCBUDMVAXZWGCZ-UHFFFAOYSA-N 3-[2-[(3-phenoxyphenyl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC=2C=C(OC=4C=CC=CC=4)C=CC=2)CC3)=C1 WCBUDMVAXZWGCZ-UHFFFAOYSA-N 0.000 claims 1
- WJVNXORPLRJLJP-UHFFFAOYSA-N 3-[2-[(3-phenylcyclobutyl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC2CC(C2)C=2C=CC=CC=2)CC3)=C1 WJVNXORPLRJLJP-UHFFFAOYSA-N 0.000 claims 1
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- LEZGKODONVRVKZ-UHFFFAOYSA-N n-[3-[2-[(1-methylindol-3-yl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound C12=CC=CC=C2N(C)C=C1CN(C(CCC1)C2)CCC21C1=CC=CC(NS(C)(=O)=O)=C1 LEZGKODONVRVKZ-UHFFFAOYSA-N 0.000 claims 1
- QYWBWTSIZMTXTF-UHFFFAOYSA-N n-[3-[2-[(1-methylpyrrol-2-yl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound CN1C=CC=C1CN1C(C2)CCCC2(C=2C=C(NS(C)(=O)=O)C=CC=2)CC1 QYWBWTSIZMTXTF-UHFFFAOYSA-N 0.000 claims 1
- PARWEPAVIFDMQQ-UHFFFAOYSA-N n-[3-[2-[(2-hydroxy-1,3-dihydroinden-2-yl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC2(O)CC4=CC=CC=C4C2)CC3)=C1 PARWEPAVIFDMQQ-UHFFFAOYSA-N 0.000 claims 1
- MWQBBRUNZRMVLU-UHFFFAOYSA-N n-[3-[2-[(2-hydroxy-1,3-dihydroinden-2-yl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC2(O)CC4=CC=CC=C4C2)CC3)=C1 MWQBBRUNZRMVLU-UHFFFAOYSA-N 0.000 claims 1
- NDUJCTOZBVKQHL-UHFFFAOYSA-N n-[3-[2-[(2-hydroxy-3,4-dihydro-1h-naphthalen-2-yl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC2(O)CC4=CC=CC=C4CC2)CC3)=C1 NDUJCTOZBVKQHL-UHFFFAOYSA-N 0.000 claims 1
- HFTKEKZOAHFQKB-UHFFFAOYSA-N n-[3-[2-[(2-hydroxy-3,4-dihydro-1h-naphthalen-2-yl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC2(O)CC4=CC=CC=C4CC2)CC3)=C1 HFTKEKZOAHFQKB-UHFFFAOYSA-N 0.000 claims 1
- NBXYTIRHNYDCIN-UHFFFAOYSA-N n-[3-[2-[(3-methyl-1-benzothiophen-2-yl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound S1C2=CC=CC=C2C(C)=C1CN(C(CCC1)C2)CCC21C1=CC=CC(NS(C)(=O)=O)=C1 NBXYTIRHNYDCIN-UHFFFAOYSA-N 0.000 claims 1
- CHQCASXJYGBJKN-UHFFFAOYSA-N n-[3-[2-[(3-phenoxyphenyl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC=2C=C(OC=4C=CC=CC=4)C=CC=2)CC3)=C1 CHQCASXJYGBJKN-UHFFFAOYSA-N 0.000 claims 1
- ILHFRMPZRSYXDA-UHFFFAOYSA-N n-[3-[2-[(3-phenylcyclobutyl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC2CC(C2)C=2C=CC=CC=2)CC3)=C1 ILHFRMPZRSYXDA-UHFFFAOYSA-N 0.000 claims 1
- QGSXBLDJYXQWEM-UHFFFAOYSA-N n-[3-[2-[(4-chloro-2-fluorophenyl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC=2C(=CC(Cl)=CC=2)F)CC3)=C1 QGSXBLDJYXQWEM-UHFFFAOYSA-N 0.000 claims 1
- UPNGKAGEJJRFKV-UHFFFAOYSA-N n-[3-[2-[(4-chloro-2-fluorophenyl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC=2C(=CC(Cl)=CC=2)F)CC3)=C1 UPNGKAGEJJRFKV-UHFFFAOYSA-N 0.000 claims 1
- GNIBEINQBOXHFN-UHFFFAOYSA-N n-[3-[2-[(4-hydroxynaphthalen-1-yl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC=2C4=CC=CC=C4C(O)=CC=2)CC3)=C1 GNIBEINQBOXHFN-UHFFFAOYSA-N 0.000 claims 1
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- IUXNCMKSYHWKOG-UHFFFAOYSA-N n-[3-[2-[(4-methoxyphenyl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CN1C(C2)CCCC2(C=2C=C(NS(C)(=O)=O)C=CC=2)CC1 IUXNCMKSYHWKOG-UHFFFAOYSA-N 0.000 claims 1
- XWJLBXMSQFQDED-UHFFFAOYSA-N n-[3-[2-[(4-phenylphenyl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC=2C=CC(=CC=2)C=2C=CC=CC=2)CC3)=C1 XWJLBXMSQFQDED-UHFFFAOYSA-N 0.000 claims 1
- LILFXKAEQHALNR-UHFFFAOYSA-N n-[3-[2-[(4-pyrrolidin-1-ylphenyl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC=2C=CC(=CC=2)N2CCCC2)CC3)=C1 LILFXKAEQHALNR-UHFFFAOYSA-N 0.000 claims 1
- DTJQBXRDMKJYFW-UHFFFAOYSA-N n-[3-[2-[2-(2-phenylethoxy)ethyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CCOCCC=2C=CC=CC=2)CC3)=C1 DTJQBXRDMKJYFW-UHFFFAOYSA-N 0.000 claims 1
- NEDRLBQKHXHFPN-UHFFFAOYSA-N n-[3-[2-[2-(4-chlorophenyl)-2-cyanoethyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC(C#N)C=2C=CC(Cl)=CC=2)CC3)=C1 NEDRLBQKHXHFPN-UHFFFAOYSA-N 0.000 claims 1
- VWHWAPBGKJVPNM-UHFFFAOYSA-N n-[3-[2-[3-(1-hydroxycyclohexyl)propyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CCCC2(O)CCCCC2)CC3)=C1 VWHWAPBGKJVPNM-UHFFFAOYSA-N 0.000 claims 1
- VWCPRVNVISOSDS-UHFFFAOYSA-N n-[3-[2-[3-(1-hydroxycyclohexyl)propyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CCCC2(O)CCCCC2)CC3)=C1 VWCPRVNVISOSDS-UHFFFAOYSA-N 0.000 claims 1
- UFXBKMVXOOCJEG-UHFFFAOYSA-N n-[3-[2-[3-(1-hydroxycyclopentyl)propyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CCCC2(O)CCCC2)CC3)=C1 UFXBKMVXOOCJEG-UHFFFAOYSA-N 0.000 claims 1
- YXVVDEJOWZIGTB-UHFFFAOYSA-N n-[3-[2-[3-(1-hydroxycyclopentyl)propyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CCCC2(O)CCCC2)CC3)=C1 YXVVDEJOWZIGTB-UHFFFAOYSA-N 0.000 claims 1
- CFIVNCPHSPADCI-UHFFFAOYSA-N n-[3-[2-[3-(2,3-dihydro-1h-inden-2-yl)propyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CCCC2CC4=CC=CC=C4C2)CC3)=C1 CFIVNCPHSPADCI-UHFFFAOYSA-N 0.000 claims 1
- BUVAVQCPEPXXJG-UHFFFAOYSA-N n-[3-[2-[3-(2,3-dihydro-1h-inden-2-yl)propyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CCCC2CC4=CC=CC=C4C2)CC3)=C1 BUVAVQCPEPXXJG-UHFFFAOYSA-N 0.000 claims 1
- TVYKVVVVCCOFPB-UHFFFAOYSA-N n-[3-[2-[3-(2-hydroxy-1,3-dihydroinden-2-yl)propyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CCCC2(O)CC4=CC=CC=C4C2)CC3)=C1 TVYKVVVVCCOFPB-UHFFFAOYSA-N 0.000 claims 1
- LJANRXDKLHZEDW-UHFFFAOYSA-N n-[3-[2-[3-[1-(hydroxymethyl)cyclopentyl]propyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CCCC2(CO)CCCC2)CC3)=C1 LJANRXDKLHZEDW-UHFFFAOYSA-N 0.000 claims 1
- VAUGDBVWSJSZJP-UHFFFAOYSA-N n-[3-[2-[3-[1-(hydroxymethyl)cyclopentyl]propyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CCCC2(CO)CCCC2)CC3)=C1 VAUGDBVWSJSZJP-UHFFFAOYSA-N 0.000 claims 1
- ONCBQJQXMFOQGI-UHFFFAOYSA-N n-[3-[2-[[1-(hydroxymethyl)cyclobutyl]methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC2(CO)CCC2)CC3)=C1 ONCBQJQXMFOQGI-UHFFFAOYSA-N 0.000 claims 1
- PPLHJFWCDNELJC-UHFFFAOYSA-N n-[3-[2-[[1-(hydroxymethyl)cyclobutyl]methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC2(CO)CCC2)CC3)=C1 PPLHJFWCDNELJC-UHFFFAOYSA-N 0.000 claims 1
- LQXDSRGESJBBTG-UHFFFAOYSA-N n-[3-[2-[[3-(trifluoromethoxy)phenyl]methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC=2C=C(OC(F)(F)F)C=CC=2)CC3)=C1 LQXDSRGESJBBTG-UHFFFAOYSA-N 0.000 claims 1
- LZSLVTOPAUEYNT-UHFFFAOYSA-N n-[3-[2-[[4-(dimethylamino)naphthalen-1-yl]methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC=2C4=CC=CC=C4C(N(C)C)=CC=2)CC3)=C1 LZSLVTOPAUEYNT-UHFFFAOYSA-N 0.000 claims 1
- VRVIAYNDDNFGCK-UHFFFAOYSA-N n-[3-[2-[[4-(dimethylamino)naphthalen-1-yl]methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound C12=CC=CC=C2C(N(C)C)=CC=C1CN(C(CCC1)C2)CCC21C1=CC=CC(NS(C)(=O)=O)=C1 VRVIAYNDDNFGCK-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
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| US46260503P | 2003-04-14 | 2003-04-14 | |
| PCT/IB2004/001237 WO2004089909A1 (en) | 2003-04-14 | 2004-04-02 | 2-azabicyclo[3.3.1]nonane derivatives as opioid receptor antagonists |
Publications (3)
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| JP2006522797A JP2006522797A (ja) | 2006-10-05 |
| JP2006522797A5 true JP2006522797A5 (enExample) | 2007-03-22 |
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| JP (1) | JP4493648B2 (enExample) |
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| ES (1) | ES2334570T3 (enExample) |
| MX (1) | MXPA05011060A (enExample) |
| WO (1) | WO2004089909A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2463264C (en) * | 2001-10-22 | 2009-05-26 | Pfizer Products Inc. | 3-azabicyclo (3.1.0) hexane derivatives as opioid receptor antagonists |
| JP3984281B2 (ja) * | 2003-04-14 | 2007-10-03 | ファイザー・プロダクツ・インク | ３−アザビシクロ〔３，２，１〕オクタン誘導体 |
| US20050043345A1 (en) * | 2003-08-22 | 2005-02-24 | Pfizer Inc | Pharmaceutical composition for the prevention and treatment of addiction in a mammal |
| MY145633A (en) | 2006-03-01 | 2012-03-15 | Theravance Inc | 8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists |
| TWI409067B (zh) * | 2007-02-28 | 2013-09-21 | Theravance Inc | ８-氮雜雙環〔３．２．１〕辛烷化合物之結晶型 |
| TWI425945B (zh) * | 2007-05-28 | 2014-02-11 | Seldar Pharma Inc | 四氫異喹啉－１－酮衍生物或其鹽 |
| ES2390195T3 (es) * | 2007-08-27 | 2012-11-07 | Theravance, Inc. | Compuestos de amidoalquil-8-azabiciclo(3,2,1)octano, como antagonistas del receptor opioide mu |
| EP2195314B1 (en) * | 2007-08-27 | 2011-03-23 | Theravance, Inc. | Disubstituted alkyl-8-azabicyclo [3.2.1.]octane compounds as mu opioid receptor antagonists |
| WO2009029253A1 (en) * | 2007-08-27 | 2009-03-05 | Theravance, Inc. | Heteroarylalkyl-8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists |
| TWI423801B (zh) | 2007-08-27 | 2014-01-21 | Theravance Inc | 作為μ類鴉片受體拮抗劑之８－氮雜雙環〔３．２．１〕辛基－２－羥基苯甲醯胺化合物 |
| GB0721178D0 (en) * | 2007-10-29 | 2007-12-05 | Glaxo Group Ltd | Chemical compounds |
| EP2919788A4 (en) | 2012-11-14 | 2016-05-25 | Univ Johns Hopkins | METHOD AND COMPOSITIONS FOR TREATING SCHIZOPHRENIA |
| MX2016006482A (es) * | 2013-11-20 | 2016-12-09 | Sanwa Kagaku Kenkyusho Co | Derivado novedoso de 3-azabiciclo[3.1.0]hexano y uso del mismo para proposito medico. |
| CA2985327A1 (en) * | 2015-05-20 | 2016-11-24 | Sanwa Kagaku Kenkyusho Co., Ltd. | Crystal of salt of 3-azabicyclo[3.1.0]hexane derivative and pharmaceutical use thereof |
| WO2017210105A1 (en) * | 2016-06-02 | 2017-12-07 | Virginia Commonwealth University | Dual modulators of both mu and kappa opioid receptors |
| WO2019152946A1 (en) | 2018-02-05 | 2019-08-08 | Alkermes, Inc. | Compounds for the treatment of pain |
| US11352365B2 (en) | 2018-03-19 | 2022-06-07 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Biased potent opioid-like agonists as improved medications to treat chronic and acute pain and methods of using the same |
| KR102266854B1 (ko) * | 2019-11-06 | 2021-06-18 | 계명대학교 산학협력단 | 마약 중독 예방 또는 치료용 약학조성물 |
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| US2143145A (en) | 1934-11-06 | 1939-01-10 | Farnsworth Television Inc | Projection means |
| US6559159B2 (en) * | 2001-02-01 | 2003-05-06 | Research Triangle Institute | Kappa opioid receptor ligands |
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2004
- 2004-01-22 US US10/762,730 patent/US7056930B2/en not_active Ceased
- 2004-04-02 DK DK04725453.7T patent/DK1615893T3/da active
- 2004-04-02 WO PCT/IB2004/001237 patent/WO2004089909A1/en not_active Ceased
- 2004-04-02 BR BRPI0409369-0A patent/BRPI0409369A/pt not_active IP Right Cessation
- 2004-04-02 ES ES04725453T patent/ES2334570T3/es not_active Expired - Lifetime
- 2004-04-02 JP JP2006506512A patent/JP4493648B2/ja not_active Expired - Fee Related
- 2004-04-02 AT AT04725453T patent/ATE449074T1/de not_active IP Right Cessation
- 2004-04-02 MX MXPA05011060A patent/MXPA05011060A/es not_active Application Discontinuation
- 2004-04-02 EP EP04725453A patent/EP1615893B1/en not_active Expired - Lifetime
- 2004-04-02 DE DE602004024188T patent/DE602004024188D1/de not_active Expired - Lifetime
- 2004-04-02 CA CA002522180A patent/CA2522180C/en not_active Expired - Fee Related
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2007
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