JP2006522795A5 - - Google Patents
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- JP2006522795A5 JP2006522795A5 JP2006506489A JP2006506489A JP2006522795A5 JP 2006522795 A5 JP2006522795 A5 JP 2006522795A5 JP 2006506489 A JP2006506489 A JP 2006506489A JP 2006506489 A JP2006506489 A JP 2006506489A JP 2006522795 A5 JP2006522795 A5 JP 2006522795A5
- Authority
- JP
- Japan
- Prior art keywords
- aza
- bicyclo
- oct
- methoxy
- phenyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- -1 2-phenethyloxy-ethyl Chemical group 0.000 claims 11
- KBPHGUKTJKPERJ-UHFFFAOYSA-N 2-methoxyethanesulfonic acid Chemical compound COCCS(O)(=O)=O KBPHGUKTJKPERJ-UHFFFAOYSA-N 0.000 claims 8
- 150000001408 amides Chemical class 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 125000002837 carbocyclic group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- LJKHNWYRBYKOMU-UHFFFAOYSA-N 2-[[8-(3-hydroxyphenyl)-3-azabicyclo[3.2.1]octan-3-yl]methyl]-1,3-dihydroinden-2-ol Chemical compound OC1=CC=CC(C2C3CCC2CN(CC2(O)CC4=CC=CC=C4C2)C3)=C1 LJKHNWYRBYKOMU-UHFFFAOYSA-N 0.000 claims 1
- GBVRAVLYQXAKRQ-UHFFFAOYSA-N 2-[[8-(3-hydroxyphenyl)-8-methoxy-3-azabicyclo[3.2.1]octan-3-yl]methyl]-1,3-dihydroinden-2-ol Chemical compound C1N(CC2(O)CC3=CC=CC=C3C2)CC2CCC1C2(OC)C1=CC=CC(O)=C1 GBVRAVLYQXAKRQ-UHFFFAOYSA-N 0.000 claims 1
- CHRSVNPINZHFDD-UHFFFAOYSA-N 3-(3-cyclohexylpropyl)-8-(3-hydroxyphenyl)-3-azabicyclo[3.2.1]octan-8-ol Chemical compound OC1=CC=CC(C2(O)C3CCC2CN(CCCC2CCCCC2)C3)=C1 CHRSVNPINZHFDD-UHFFFAOYSA-N 0.000 claims 1
- IGAPFAKNLLGKIC-UHFFFAOYSA-N 3-(3-ethyl-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl)benzamide Chemical compound C1N(CC)CC2CCC1C2(OC)C1=CC=CC(C(N)=O)=C1 IGAPFAKNLLGKIC-UHFFFAOYSA-N 0.000 claims 1
- OGDMUMNMVWWHMB-UHFFFAOYSA-N 3-(3-hexyl-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl)benzamide Chemical compound C1N(CCCCCC)CC2CCC1C2(OC)C1=CC=CC(C(N)=O)=C1 OGDMUMNMVWWHMB-UHFFFAOYSA-N 0.000 claims 1
- WEYLTQVDHFOPML-UHFFFAOYSA-N 3-(8-methoxy-3-octyl-3-azabicyclo[3.2.1]octan-8-yl)benzamide Chemical compound C1N(CCCCCCCC)CC2CCC1C2(OC)C1=CC=CC(C(N)=O)=C1 WEYLTQVDHFOPML-UHFFFAOYSA-N 0.000 claims 1
- UIVQSBBVLBOXML-UHFFFAOYSA-N 3-(8-methoxy-3-pentyl-3-azabicyclo[3.2.1]octan-8-yl)benzamide Chemical compound C1N(CCCCC)CC2CCC1C2(OC)C1=CC=CC(C(N)=O)=C1 UIVQSBBVLBOXML-UHFFFAOYSA-N 0.000 claims 1
- HRTPJWHXXKNJOO-UHFFFAOYSA-N 3-(cyclopropylmethyl)-8-(3-hydroxyphenyl)-3-azabicyclo[3.2.1]octan-8-ol Chemical compound OC1=CC=CC(C2(O)C3CCC2CN(CC2CC2)C3)=C1 HRTPJWHXXKNJOO-UHFFFAOYSA-N 0.000 claims 1
- AACWZBRUTYOVMT-UHFFFAOYSA-N 3-[(2-hydroxy-1,3-dihydroinden-2-yl)methyl]-8-(3-hydroxyphenyl)-3-azabicyclo[3.2.1]octan-6-ol Chemical compound C1C2CN(CC(C1O)C2C3=CC(=CC=C3)O)CC4(CC5=CC=CC=C5C4)O AACWZBRUTYOVMT-UHFFFAOYSA-N 0.000 claims 1
- DYDYMFIWPGPJTP-UHFFFAOYSA-N 3-[3-(1-benzofuran-2-ylmethyl)-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C1N(CC=2OC3=CC=CC=C3C=2)CC2CCC1C2(OC)C1=CC=CC(C(N)=O)=C1 DYDYMFIWPGPJTP-UHFFFAOYSA-N 0.000 claims 1
- UTPBAHMWJFMDKU-UHFFFAOYSA-N 3-[3-(1-hydroxycyclohexyl)propyl]-8-(3-hydroxyphenyl)-3-azabicyclo[3.2.1]octan-8-ol Chemical compound OC1=CC=CC(C2(O)C3CCC2CN(CCCC2(O)CCCCC2)C3)=C1 UTPBAHMWJFMDKU-UHFFFAOYSA-N 0.000 claims 1
- ISLXTQPUFZDQTE-UHFFFAOYSA-N 3-[3-(1h-indol-3-ylmethyl)-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C1N(CC=2C3=CC=CC=C3NC=2)CC2CCC1C2(OC)C1=CC=CC(C(N)=O)=C1 ISLXTQPUFZDQTE-UHFFFAOYSA-N 0.000 claims 1
- XNTBRHQEBYRQOT-UHFFFAOYSA-N 3-[3-(2-ethylbutyl)-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C1N(CC(CC)CC)CC2CCC1C2(OC)C1=CC=CC(C(N)=O)=C1 XNTBRHQEBYRQOT-UHFFFAOYSA-N 0.000 claims 1
- GPBQYIUZFYDTRH-UHFFFAOYSA-N 3-[3-(3-cyclohexylpropyl)-3-azabicyclo[3.2.1]octan-8-yl]phenol Chemical compound OC1=CC=CC(C2C3CCC2CN(CCCC2CCCCC2)C3)=C1 GPBQYIUZFYDTRH-UHFFFAOYSA-N 0.000 claims 1
- YCTZDWPWLMGXPV-UHFFFAOYSA-N 3-[3-(9h-fluoren-2-ylmethyl)-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C1N(CC=2C=C3C(C4=CC=CC=C4C3)=CC=2)CC2CCC1C2(OC)C1=CC=CC(C(N)=O)=C1 YCTZDWPWLMGXPV-UHFFFAOYSA-N 0.000 claims 1
- QOFYIVXNRRSTIF-UHFFFAOYSA-N 3-[3-(cyclopropylmethyl)-3-azabicyclo[3.2.1]octan-8-yl]phenol Chemical compound OC1=CC=CC(C2C3CCC2CN(CC2CC2)C3)=C1 QOFYIVXNRRSTIF-UHFFFAOYSA-N 0.000 claims 1
- QFZKVOIQIGKEPM-UHFFFAOYSA-N 3-[3-(cyclopropylmethyl)-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C=1C=CC(C(N)=O)=CC=1C1(OC)C(C2)CCC1CN2CC1CC1 QFZKVOIQIGKEPM-UHFFFAOYSA-N 0.000 claims 1
- CQMGDWUBLFGSDQ-UHFFFAOYSA-N 3-[3-[(1-hydroxy-3-phenylcyclobutyl)methyl]-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C=1C=CC(C(N)=O)=CC=1C1(OC)C(C2)CCC1CN2CC(C1)(O)CC1C1=CC=CC=C1 CQMGDWUBLFGSDQ-UHFFFAOYSA-N 0.000 claims 1
- PNUIAAYEYHRGJI-UHFFFAOYSA-N 3-[3-[(2-hydroxy-1,3-dihydroinden-2-yl)methyl]-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C1N(CC2(O)CC3=CC=CC=C3C2)CC2CCC1C2(OC)C1=CC=CC(C(N)=O)=C1 PNUIAAYEYHRGJI-UHFFFAOYSA-N 0.000 claims 1
- WSPUTPGIXVRVDQ-UHFFFAOYSA-N 3-[3-[(2-hydroxy-3,4-dihydro-1h-naphthalen-2-yl)methyl]-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C2C3CCC2CN(CC2(O)CC4=CC=CC=C4CC2)C3)=C1 WSPUTPGIXVRVDQ-UHFFFAOYSA-N 0.000 claims 1
- CWHLZLLPFTWBLR-UHFFFAOYSA-N 3-[3-[(2-hydroxy-3,4-dihydro-1h-naphthalen-2-yl)methyl]-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C1N(CC2(O)CC3=CC=CC=C3CC2)CC2CCC1C2(OC)C1=CC=CC(C(N)=O)=C1 CWHLZLLPFTWBLR-UHFFFAOYSA-N 0.000 claims 1
- WWCODHARKXIVKR-UHFFFAOYSA-N 3-[3-[(4-chloro-2-fluorophenyl)methyl]-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C=1C=CC(C(N)=O)=CC=1C1(OC)C(C2)CCC1CN2CC1=CC=C(Cl)C=C1F WWCODHARKXIVKR-UHFFFAOYSA-N 0.000 claims 1
- FTQHFYJUCNMHNV-UHFFFAOYSA-N 3-[3-[(4-hydroxynaphthalen-1-yl)methyl]-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C1N(CC=2C3=CC=CC=C3C(O)=CC=2)CC2CCC1C2(OC)C1=CC=CC(C(N)=O)=C1 FTQHFYJUCNMHNV-UHFFFAOYSA-N 0.000 claims 1
- GNVHZVXOZKIKTP-UHFFFAOYSA-N 3-[3-[3-(1-hydroxycyclohexyl)propyl]-3-azabicyclo[3.2.1]octan-8-yl]phenol Chemical compound OC1=CC=CC(C2C3CCC2CN(CCCC2(O)CCCCC2)C3)=C1 GNVHZVXOZKIKTP-UHFFFAOYSA-N 0.000 claims 1
- PCUUSYJXGVLVTO-UHFFFAOYSA-N 3-[3-[3-(1-hydroxycyclohexyl)propyl]-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C=1C=CC(C(N)=O)=CC=1C1(OC)C(C2)CCC1CN2CCCC1(O)CCCCC1 PCUUSYJXGVLVTO-UHFFFAOYSA-N 0.000 claims 1
- ISINKTTZISDVRB-UHFFFAOYSA-N 3-[3-[3-(1-hydroxycyclohexyl)propyl]-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]phenol Chemical compound C=1C=CC(O)=CC=1C1(OC)C(C2)CCC1CN2CCCC1(O)CCCCC1 ISINKTTZISDVRB-UHFFFAOYSA-N 0.000 claims 1
- FCQVELOKRBLHKY-UHFFFAOYSA-N 3-[3-[[4-(dimethylamino)naphthalen-1-yl]methyl]-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C1N(CC=2C3=CC=CC=C3C(N(C)C)=CC=2)CC2CCC1C2(OC)C1=CC=CC(C(N)=O)=C1 FCQVELOKRBLHKY-UHFFFAOYSA-N 0.000 claims 1
- OHJKHDSQVWMDNQ-UHFFFAOYSA-N 3-[8-hydroxy-3-[(2-hydroxy-3,4-dihydro-1h-naphthalen-2-yl)methyl]-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C2(O)C3CCC2CN(CC2(O)CC4=CC=CC=C4CC2)C3)=C1 OHJKHDSQVWMDNQ-UHFFFAOYSA-N 0.000 claims 1
- YRMXBOFWMGEADC-UHFFFAOYSA-N 3-[8-methoxy-3-(1,3-thiazol-2-ylmethyl)-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C=1C=CC(C(N)=O)=CC=1C1(OC)C(C2)CCC1CN2CC1=NC=CS1 YRMXBOFWMGEADC-UHFFFAOYSA-N 0.000 claims 1
- PRWBIFYYIPVQNJ-UHFFFAOYSA-N 3-[8-methoxy-3-(1h-pyrrol-2-ylmethyl)-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C=1C=CC(C(N)=O)=CC=1C1(OC)C(C2)CCC1CN2CC1=CC=CN1 PRWBIFYYIPVQNJ-UHFFFAOYSA-N 0.000 claims 1
- ADRGZGNTZJIBRH-UHFFFAOYSA-N 3-[8-methoxy-3-(2-phenylethyl)-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C=1C=CC(C(N)=O)=CC=1C1(OC)C(C2)CCC1CN2CCC1=CC=CC=C1 ADRGZGNTZJIBRH-UHFFFAOYSA-N 0.000 claims 1
- ATQBWMYHVOGENS-UHFFFAOYSA-N 3-[8-methoxy-3-(3-methylbutyl)-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C1N(CCC(C)C)CC2CCC1C2(OC)C1=CC=CC(C(N)=O)=C1 ATQBWMYHVOGENS-UHFFFAOYSA-N 0.000 claims 1
- FZORMFSGPZLSBZ-UHFFFAOYSA-N 3-[8-methoxy-3-(3-phenylprop-2-ynyl)-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C=1C=CC(C(N)=O)=CC=1C1(OC)C(C2)CCC1CN2CC#CC1=CC=CC=C1 FZORMFSGPZLSBZ-UHFFFAOYSA-N 0.000 claims 1
- UTPMUXUGONAUBR-UHFFFAOYSA-N 3-[8-methoxy-3-(3-phenylpropyl)-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C=1C=CC(C(N)=O)=CC=1C1(OC)C(C2)CCC1CN2CCCC1=CC=CC=C1 UTPMUXUGONAUBR-UHFFFAOYSA-N 0.000 claims 1
- IGQKNXWTTINOBW-UHFFFAOYSA-N 3-[8-methoxy-3-(naphthalen-2-ylmethyl)-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C1N(CC=2C=C3C=CC=CC3=CC=2)CC2CCC1C2(OC)C1=CC=CC(C(N)=O)=C1 IGQKNXWTTINOBW-UHFFFAOYSA-N 0.000 claims 1
- MSUKYTUVQWSBTI-UHFFFAOYSA-N 3-[8-methoxy-3-(quinolin-3-ylmethyl)-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C1N(CC=2C=C3C=CC=CC3=NC=2)CC2CCC1C2(OC)C1=CC=CC(C(N)=O)=C1 MSUKYTUVQWSBTI-UHFFFAOYSA-N 0.000 claims 1
- CFEQHLIMFCLFOA-UHFFFAOYSA-N 3-[8-methoxy-3-(thiophen-3-ylmethyl)-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C=1C=CC(C(N)=O)=CC=1C1(OC)C(C2)CCC1CN2CC=1C=CSC=1 CFEQHLIMFCLFOA-UHFFFAOYSA-N 0.000 claims 1
- ZAKIKMYAPWPNIK-UHFFFAOYSA-N 3-[8-methoxy-3-[(1-methylindol-3-yl)methyl]-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C1N(CC=2C3=CC=CC=C3N(C)C=2)CC2CCC1C2(OC)C1=CC=CC(C(N)=O)=C1 ZAKIKMYAPWPNIK-UHFFFAOYSA-N 0.000 claims 1
- RPPHPLCZSMWUJM-UHFFFAOYSA-N 3-[8-methoxy-3-[(1-methylpyrrol-2-yl)methyl]-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C=1C=CC(C(N)=O)=CC=1C1(OC)C(C2)CCC1CN2CC1=CC=CN1C RPPHPLCZSMWUJM-UHFFFAOYSA-N 0.000 claims 1
- BHDUACUDDIZLPI-UHFFFAOYSA-N 3-[8-methoxy-3-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C1N(CC2=C(C3=CC=CC=C3S2)C)CC2CCC1C2(OC)C1=CC=CC(C(N)=O)=C1 BHDUACUDDIZLPI-UHFFFAOYSA-N 0.000 claims 1
- AUZGOFUNPRBCAD-UHFFFAOYSA-N 3-[8-methoxy-3-[(3-phenoxyphenyl)methyl]-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C=1C=CC(C(N)=O)=CC=1C1(OC)C(C2)CCC1CN2CC(C=1)=CC=CC=1OC1=CC=CC=C1 AUZGOFUNPRBCAD-UHFFFAOYSA-N 0.000 claims 1
- PMHKVISSLNHQAY-UHFFFAOYSA-N 3-[8-methoxy-3-[(4-phenylphenyl)methyl]-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C=1C=CC(C(N)=O)=CC=1C1(OC)C(C2)CCC1CN2CC(C=C1)=CC=C1C1=CC=CC=C1 PMHKVISSLNHQAY-UHFFFAOYSA-N 0.000 claims 1
- SBLKFDMVAQVNLA-UHFFFAOYSA-N 3-[8-methoxy-3-[(4-pyrrolidin-1-ylphenyl)methyl]-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C=1C=CC(C(N)=O)=CC=1C1(OC)C(C2)CCC1CN2CC(C=C1)=CC=C1N1CCCC1 SBLKFDMVAQVNLA-UHFFFAOYSA-N 0.000 claims 1
- YZESNXVGSZPFEI-UHFFFAOYSA-N 3-[8-methoxy-3-[[3-(trifluoromethoxy)phenyl]methyl]-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C=1C=CC(C(N)=O)=CC=1C1(OC)C(C2)CCC1CN2CC1=CC=CC(OC(F)(F)F)=C1 YZESNXVGSZPFEI-UHFFFAOYSA-N 0.000 claims 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- AMBUTABHSXABCY-UHFFFAOYSA-N COCCS(=O)(=O)NC1=CC=CC(C2C3CCC2CN(CC2(O)CC4=CC=CC=C4CC2)C3)=C1 Chemical compound COCCS(=O)(=O)NC1=CC=CC(C2C3CCC2CN(CC2(O)CC4=CC=CC=C4CC2)C3)=C1 AMBUTABHSXABCY-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 1
- 125000004130 indan-2-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])(*)C2([H])[H] 0.000 claims 1
- KWGUSNSGIPXAQH-UHFFFAOYSA-N n-[3-(3-heptyl-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl)phenyl]methanesulfonamide Chemical compound C1N(CCCCCCC)CC2CCC1C2(OC)C1=CC=CC(NS(C)(=O)=O)=C1 KWGUSNSGIPXAQH-UHFFFAOYSA-N 0.000 claims 1
- HKKYNLSMFBRFOB-UHFFFAOYSA-N n-[3-(3-hexyl-8-hydroxy-3-azabicyclo[3.2.1]octan-8-yl)phenyl]-2-methoxyethanesulfonamide Chemical compound C1N(CCCCCC)CC2CCC1C2(O)C1=CC=CC(NS(=O)(=O)CCOC)=C1 HKKYNLSMFBRFOB-UHFFFAOYSA-N 0.000 claims 1
- VXQVNZYMRRTORV-UHFFFAOYSA-N n-[3-(3-hexyl-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl)phenyl]methanesulfonamide Chemical compound C1N(CCCCCC)CC2CCC1C2(OC)C1=CC=CC(NS(C)(=O)=O)=C1 VXQVNZYMRRTORV-UHFFFAOYSA-N 0.000 claims 1
- MSMJPLBTXKRCEO-UHFFFAOYSA-N n-[3-(8-hydroxy-3-octyl-3-azabicyclo[3.2.1]octan-8-yl)phenyl]-2-methoxyethanesulfonamide Chemical compound C1N(CCCCCCCC)CC2CCC1C2(O)C1=CC=CC(NS(=O)(=O)CCOC)=C1 MSMJPLBTXKRCEO-UHFFFAOYSA-N 0.000 claims 1
- KTFBCRIPLMBXNT-UHFFFAOYSA-N n-[3-(8-hydroxy-3-pentyl-3-azabicyclo[3.2.1]octan-8-yl)phenyl]-2-methoxyethanesulfonamide Chemical compound C1N(CCCCC)CC2CCC1C2(O)C1=CC=CC(NS(=O)(=O)CCOC)=C1 KTFBCRIPLMBXNT-UHFFFAOYSA-N 0.000 claims 1
- QQXNZYFMHUUHJV-UHFFFAOYSA-N n-[3-(8-methoxy-3-octyl-3-azabicyclo[3.2.1]octan-8-yl)phenyl]methanesulfonamide Chemical compound C1N(CCCCCCCC)CC2CCC1C2(OC)C1=CC=CC(NS(C)(=O)=O)=C1 QQXNZYFMHUUHJV-UHFFFAOYSA-N 0.000 claims 1
- VGBYDMDBKOSGQN-UHFFFAOYSA-N n-[3-(8-methoxy-3-pentyl-3-azabicyclo[3.2.1]octan-8-yl)phenyl]methanesulfonamide Chemical compound C1N(CCCCC)CC2CCC1C2(OC)C1=CC=CC(NS(C)(=O)=O)=C1 VGBYDMDBKOSGQN-UHFFFAOYSA-N 0.000 claims 1
- HQTBQABSFHETFZ-UHFFFAOYSA-N n-[3-[3-(1-benzofuran-2-ylmethyl)-8-hydroxy-3-azabicyclo[3.2.1]octan-8-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C2(O)C3CCC2CN(CC=2OC4=CC=CC=C4C=2)C3)=C1 HQTBQABSFHETFZ-UHFFFAOYSA-N 0.000 claims 1
- NBHGQMKYORYLEA-UHFFFAOYSA-N n-[3-[3-(1-benzofuran-2-ylmethyl)-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C1N(CC=2OC3=CC=CC=C3C=2)CC2CCC1C2(OC)C1=CC=CC(NS(C)(=O)=O)=C1 NBHGQMKYORYLEA-UHFFFAOYSA-N 0.000 claims 1
- GKRNZTOMLFNLDF-UHFFFAOYSA-N n-[3-[3-(1h-indol-3-ylmethyl)-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C1N(CC=2C3=CC=CC=C3NC=2)CC2CCC1C2(OC)C1=CC=CC(NS(C)(=O)=O)=C1 GKRNZTOMLFNLDF-UHFFFAOYSA-N 0.000 claims 1
- SYJLKMUPIMOIDR-UHFFFAOYSA-N n-[3-[3-(2-ethylbutyl)-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C1N(CC(CC)CC)CC2CCC1C2(OC)C1=CC=CC(NS(C)(=O)=O)=C1 SYJLKMUPIMOIDR-UHFFFAOYSA-N 0.000 claims 1
- CFILBLSAVXOYJU-UHFFFAOYSA-N n-[3-[3-(2-ethylhexyl)-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C1N(CC(CC)CCCC)CC2CCC1C2(OC)C1=CC=CC(NS(C)(=O)=O)=C1 CFILBLSAVXOYJU-UHFFFAOYSA-N 0.000 claims 1
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- NSLNJHNLBGLZDD-UHFFFAOYSA-N n-[3-[8-hydroxy-3-(thiophen-3-ylmethyl)-3-azabicyclo[3.2.1]octan-8-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C2(O)C3CCC2CN(CC2=CSC=C2)C3)=C1 NSLNJHNLBGLZDD-UHFFFAOYSA-N 0.000 claims 1
- QPIHORZVLPNOAY-UHFFFAOYSA-N n-[3-[8-hydroxy-3-[(1-methylindol-3-yl)methyl]-3-azabicyclo[3.2.1]octan-8-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C2(O)C3CCC2CN(CC=2C4=CC=CC=C4N(C)C=2)C3)=C1 QPIHORZVLPNOAY-UHFFFAOYSA-N 0.000 claims 1
- KQRVYIMNGHAEML-UHFFFAOYSA-N n-[3-[8-hydroxy-3-[(2-hydroxy-3,4-dihydro-1h-naphthalen-2-yl)methyl]-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C2(O)C3CCC2CN(CC2(O)CC4=CC=CC=C4CC2)C3)=C1 KQRVYIMNGHAEML-UHFFFAOYSA-N 0.000 claims 1
- KDSNLTFYEIJQJB-UHFFFAOYSA-N n-[3-[8-hydroxy-3-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-azabicyclo[3.2.1]octan-8-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C2(O)C3CCC2CN(CC2=C(C4=CC=CC=C4S2)C)C3)=C1 KDSNLTFYEIJQJB-UHFFFAOYSA-N 0.000 claims 1
- OYBXJQACINXRFB-UHFFFAOYSA-N n-[3-[8-hydroxy-3-[(3-phenoxyphenyl)methyl]-3-azabicyclo[3.2.1]octan-8-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C2(O)C3CCC2CN(CC=2C=C(OC=4C=CC=CC=4)C=CC=2)C3)=C1 OYBXJQACINXRFB-UHFFFAOYSA-N 0.000 claims 1
- HGJLOOTWWFDZAI-UHFFFAOYSA-N n-[3-[8-hydroxy-3-[(4-phenylphenyl)methyl]-3-azabicyclo[3.2.1]octan-8-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C2(O)C3CCC2CN(CC=2C=CC(=CC=2)C=2C=CC=CC=2)C3)=C1 HGJLOOTWWFDZAI-UHFFFAOYSA-N 0.000 claims 1
- VOYNJQCZABYDME-UHFFFAOYSA-N n-[3-[8-hydroxy-3-[2-(2-phenylethoxy)ethyl]-3-azabicyclo[3.2.1]octan-8-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C2(O)C3CCC2CN(CCOCCC=2C=CC=CC=2)C3)=C1 VOYNJQCZABYDME-UHFFFAOYSA-N 0.000 claims 1
- PFSXUTHJQJBTRV-UHFFFAOYSA-N n-[3-[8-hydroxy-3-[3-(1-hydroxycyclohexyl)propyl]-3-azabicyclo[3.2.1]octan-8-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C2(O)C3CCC2CN(CCCC2(O)CCCCC2)C3)=C1 PFSXUTHJQJBTRV-UHFFFAOYSA-N 0.000 claims 1
- PQESBFCKZNUYIC-UHFFFAOYSA-N n-[3-[8-methoxy-3-(1,3-thiazol-2-ylmethyl)-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C=1C=CC(NS(C)(=O)=O)=CC=1C1(OC)C(C2)CCC1CN2CC1=NC=CS1 PQESBFCKZNUYIC-UHFFFAOYSA-N 0.000 claims 1
- IYVKAWKAXVZLLW-UHFFFAOYSA-N n-[3-[8-methoxy-3-(2-methylpropyl)-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C1N(CC(C)C)CC2CCC1C2(OC)C1=CC=CC(NS(C)(=O)=O)=C1 IYVKAWKAXVZLLW-UHFFFAOYSA-N 0.000 claims 1
- HJTVVLATNWVAPK-UHFFFAOYSA-N n-[3-[8-methoxy-3-(2-phenylethyl)-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C=1C=CC(NS(C)(=O)=O)=CC=1C1(OC)C(C2)CCC1CN2CCC1=CC=CC=C1 HJTVVLATNWVAPK-UHFFFAOYSA-N 0.000 claims 1
- PIJBDVFTXDATEV-UHFFFAOYSA-N n-[3-[8-methoxy-3-(3-methylbutyl)-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C1N(CCC(C)C)CC2CCC1C2(OC)C1=CC=CC(NS(C)(=O)=O)=C1 PIJBDVFTXDATEV-UHFFFAOYSA-N 0.000 claims 1
- OIEDNQVNHGONKR-UHFFFAOYSA-N n-[3-[8-methoxy-3-(naphthalen-1-ylmethyl)-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C1N(CC=2C3=CC=CC=C3C=CC=2)CC2CCC1C2(OC)C1=CC=CC(NS(C)(=O)=O)=C1 OIEDNQVNHGONKR-UHFFFAOYSA-N 0.000 claims 1
- YJSDSLFVDLAPMX-UHFFFAOYSA-N n-[3-[8-methoxy-3-(naphthalen-2-ylmethyl)-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C1N(CC=2C=C3C=CC=CC3=CC=2)CC2CCC1C2(OC)C1=CC=CC(NS(C)(=O)=O)=C1 YJSDSLFVDLAPMX-UHFFFAOYSA-N 0.000 claims 1
- DWAGSWHKIIYILN-UHFFFAOYSA-N n-[3-[8-methoxy-3-(pyridin-3-ylmethyl)-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C=1C=CC(NS(C)(=O)=O)=CC=1C1(OC)C(C2)CCC1CN2CC1=CC=CN=C1 DWAGSWHKIIYILN-UHFFFAOYSA-N 0.000 claims 1
- MDTPYFNFGJDZMO-UHFFFAOYSA-N n-[3-[8-methoxy-3-(quinolin-3-ylmethyl)-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C1N(CC=2C=C3C=CC=CC3=NC=2)CC2CCC1C2(OC)C1=CC=CC(NS(C)(=O)=O)=C1 MDTPYFNFGJDZMO-UHFFFAOYSA-N 0.000 claims 1
- VJRLWOQKLRUIEA-UHFFFAOYSA-N n-[3-[8-methoxy-3-(quinolin-4-ylmethyl)-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C1N(CC=2C3=CC=CC=C3N=CC=2)CC2CCC1C2(OC)C1=CC=CC(NS(C)(=O)=O)=C1 VJRLWOQKLRUIEA-UHFFFAOYSA-N 0.000 claims 1
- OJJJEPVNORLVDF-UHFFFAOYSA-N n-[3-[8-methoxy-3-[(3-methyl-1-benzothiophen-2-yl)methyl]-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C1N(CC2=C(C3=CC=CC=C3S2)C)CC2CCC1C2(OC)C1=CC=CC(NS(C)(=O)=O)=C1 OJJJEPVNORLVDF-UHFFFAOYSA-N 0.000 claims 1
- VSXOPQIFUKRSPJ-UHFFFAOYSA-N n-[3-[8-methoxy-3-[(3-phenoxyphenyl)methyl]-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C=1C=CC(NS(C)(=O)=O)=CC=1C1(OC)C(C2)CCC1CN2CC(C=1)=CC=CC=1OC1=CC=CC=C1 VSXOPQIFUKRSPJ-UHFFFAOYSA-N 0.000 claims 1
- XDHULNQGMOCASU-UHFFFAOYSA-N n-[3-[8-methoxy-3-[(4-methoxyphenyl)methyl]-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C1=CC(OC)=CC=C1CN1CC(C2(OC)C=3C=C(NS(C)(=O)=O)C=CC=3)CCC2C1 XDHULNQGMOCASU-UHFFFAOYSA-N 0.000 claims 1
- FVHGQEDMLSDSBI-UHFFFAOYSA-N n-[3-[8-methoxy-3-[(4-phenylphenyl)methyl]-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C=1C=CC(NS(C)(=O)=O)=CC=1C1(OC)C(C2)CCC1CN2CC(C=C1)=CC=C1C1=CC=CC=C1 FVHGQEDMLSDSBI-UHFFFAOYSA-N 0.000 claims 1
- SRPVSZBCSZBLLF-UHFFFAOYSA-N n-[3-[8-methoxy-3-[(4-pyrrolidin-1-ylphenyl)methyl]-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C=1C=CC(NS(C)(=O)=O)=CC=1C1(OC)C(C2)CCC1CN2CC(C=C1)=CC=C1N1CCCC1 SRPVSZBCSZBLLF-UHFFFAOYSA-N 0.000 claims 1
- VGPYIXCKJSMSNC-UHFFFAOYSA-N n-[3-[8-methoxy-3-[[3-(trifluoromethoxy)phenyl]methyl]-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C=1C=CC(NS(C)(=O)=O)=CC=1C1(OC)C(C2)CCC1CN2CC1=CC=CC(OC(F)(F)F)=C1 VGPYIXCKJSMSNC-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
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| PCT/IB2004/001189 WO2004089908A2 (en) | 2003-04-14 | 2004-04-02 | 3-azabicyclo[3.2.1]octane derivatives |
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| CA2522323C (en) | 2003-04-14 | 2009-09-15 | Pfizer Products Inc. | 3-azabicyclo[3.2.1]octane derivatives as opioid receptor ligands |
| 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 |
| TWI415850B (zh) | 2007-07-20 | 2013-11-21 | Theravance Inc | 製備ｍｕ類鴉片受體拮抗劑之中間物的方法 |
| 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 |
| ATE502939T1 (de) * | 2007-08-27 | 2011-04-15 | Theravance Inc | Disubstituierte alkyl-8-azabicycloä3.2.1üoktan- verbindungen als mu-opioid-rezeptorantagonisten |
| WO2009029253A1 (en) * | 2007-08-27 | 2009-03-05 | Theravance, Inc. | Heteroarylalkyl-8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists |
| WO2009029252A1 (en) | 2007-08-27 | 2009-03-05 | Theravance, Inc. | Amidoalkyl-8-azabicyclo[3.2.1]octane compounds as mu opioid receptor antagonists |
| EP2039679B1 (en) * | 2007-09-20 | 2015-08-12 | Przedsiebiorstwo Produkcyjno-Consultingowe ADOB sp. z o.o. sp. k. | A process for the preparation of N,N'-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid and its derivatives |
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2004
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- 2004-04-02 MX MXPA05011070A patent/MXPA05011070A/es unknown
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- 2004-04-02 EP EP04725450A patent/EP1615894A2/en not_active Withdrawn
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- 2004-04-13 UY UY28265A patent/UY28265A1/es not_active Application Discontinuation
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