MXPA05002621A

MXPA05002621A - Compuestos diazabiciclos utiles en el tratamiento de transtornos del sistema nervioso central y otros trastornos.

Compuestos diazabiciclos utiles en el tratamiento de transtornos del sistema nervioso central y otros trastornos.

Info

Publication number: MXPA05002621A
Authority: MX; Mexico
Prior art keywords: diaza; bicyclo; pyridin; decane; octane
Prior art date: 2002-09-10

Application number

MXPA05002621A

Other languages

English (en)

Spanish (es)

Inventor

Christopher John O'donell

Original Assignee

Pfizer Prod Inc

Priority date

2002-09-10

Filing date

2003-08-29

Publication date

2005-05-05

2003-08-29 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2005-05-05 Publication of MXPA05002621A publication Critical patent/MXPA05002621A/es

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 245
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239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
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-1 alky (Ci-C6) Chemical group 0.000 claims description 233
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 112
125000003118 aryl group Chemical group 0.000 claims description 28
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 24
125000001072 heteroaryl group Chemical group 0.000 claims description 21
229910052794 bromium Inorganic materials 0.000 claims description 20
229910052740 iodine Inorganic materials 0.000 claims description 20
BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 20
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 17
125000000753 cycloalkyl group Chemical group 0.000 claims description 16
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229910052801 chlorine Inorganic materials 0.000 claims description 15
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DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 14
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 14
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 14
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125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
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125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 9
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 9
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241000124008 Mammalia Species 0.000 claims description 8
229910052796 boron Inorganic materials 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 8
FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 claims description 7
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125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 7
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125000006554 (C4-C8) cycloalkenyl group Chemical group 0.000 claims description 6
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LJWBVWXRRPTZIS-UHFFFAOYSA-N 4-(5-methoxypyridin-3-yl)-1,4-diazabicyclo[3.3.2]decane Chemical compound COC1=CN=CC(N2C3CCCN(CC3)CC2)=C1 LJWBVWXRRPTZIS-UHFFFAOYSA-N 0.000 claims description 6
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QQBOBWKKYBWQDP-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)pyridin-2-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(N2C3CCCN(CC3)CC2)N=C1 QQBOBWKKYBWQDP-UHFFFAOYSA-N 0.000 claims description 6
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QFJTUXBLRBWTEJ-UHFFFAOYSA-N 4-(6-methylpyridin-3-yl)-1,4-diazabicyclo[3.3.2]decane Chemical compound C1=NC(C)=CC=C1N1C(CC2)CCCN2CC1 QFJTUXBLRBWTEJ-UHFFFAOYSA-N 0.000 claims description 5
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GIPKYCKNDKUZIJ-UHFFFAOYSA-N 4-[5-(2-methoxyphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound COC1=CC=CC=C1C1=CN=CC(N2C3CCN(C3)CC2)=C1 GIPKYCKNDKUZIJ-UHFFFAOYSA-N 0.000 claims description 5
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BDEPCXUCJDOPEX-UHFFFAOYSA-N 4-[5-(3-fluorophenyl)pyridin-2-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound FC1=CC=CC(C=2C=NC(=CC=2)N2C3CCCN(C3)CC2)=C1 BDEPCXUCJDOPEX-UHFFFAOYSA-N 0.000 claims description 5
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LTIDGJOYUJPYNL-UHFFFAOYSA-N ethyl 5-(1,4-diazabicyclo[3.3.1]nonan-4-yl)pyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=CC(N2C3CCCN(C3)CC2)=C1 LTIDGJOYUJPYNL-UHFFFAOYSA-N 0.000 claims description 5
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
PAKIRKMGOXJXPJ-UHFFFAOYSA-N 4-(3-bromophenyl)-1,4-diazabicyclo[3.2.1]octane Chemical compound BrC1=CC=CC(N2C3CCN(C3)CC2)=C1 PAKIRKMGOXJXPJ-UHFFFAOYSA-N 0.000 claims description 4
RZOFBCHTTCAGOJ-UHFFFAOYSA-N 4-(3-bromophenyl)-1,4-diazabicyclo[3.3.1]nonane Chemical compound BrC1=CC=CC(N2C3CCCN(C3)CC2)=C1 RZOFBCHTTCAGOJ-UHFFFAOYSA-N 0.000 claims description 4
DJSVJNXUPNCAES-UHFFFAOYSA-N 4-(5-bromopyridin-3-yl)-1,4-diazabicyclo[3.2.1]octane Chemical compound BrC1=CN=CC(N2C3CCN(C3)CC2)=C1 DJSVJNXUPNCAES-UHFFFAOYSA-N 0.000 claims description 4
GOZFRBCNVGUKQZ-UHFFFAOYSA-N 4-(5-chloropyridin-2-yl)-1,4-diazabicyclo[3.2.1]octane Chemical compound N1=CC(Cl)=CC=C1N1C(C2)CCN2CC1 GOZFRBCNVGUKQZ-UHFFFAOYSA-N 0.000 claims description 4
GULGZYQNYCLMGE-UHFFFAOYSA-N 4-(5-chloropyridin-2-yl)-1,4-diazabicyclo[3.3.2]decane Chemical compound N1=CC(Cl)=CC=C1N1C(CC2)CCCN2CC1 GULGZYQNYCLMGE-UHFFFAOYSA-N 0.000 claims description 4
WRAIIFJOHGJMOG-UHFFFAOYSA-N 4-(5-chloropyridin-3-yl)-1,4-diazabicyclo[3.2.1]octane Chemical compound ClC1=CN=CC(N2C3CCN(C3)CC2)=C1 WRAIIFJOHGJMOG-UHFFFAOYSA-N 0.000 claims description 4
OLMRKBMRQCMXCC-UHFFFAOYSA-N 4-(5-chloropyridin-3-yl)-1,4-diazabicyclo[3.3.1]nonane Chemical compound ClC1=CN=CC(N2C3CCCN(C3)CC2)=C1 OLMRKBMRQCMXCC-UHFFFAOYSA-N 0.000 claims description 4
VILSVHLWVFBVRH-UHFFFAOYSA-N 4-(5-methoxypyridin-3-yl)-1,4-diazabicyclo[3.2.1]octane Chemical compound COC1=CN=CC(N2C3CCN(C3)CC2)=C1 VILSVHLWVFBVRH-UHFFFAOYSA-N 0.000 claims description 4
GVDPDUFGZDFRIT-UHFFFAOYSA-N 4-(5-phenylpyridin-3-yl)-1,4-diazabicyclo[3.2.1]octane Chemical compound C1CN(CC2)CC1N2C(C=1)=CN=CC=1C1=CC=CC=C1 GVDPDUFGZDFRIT-UHFFFAOYSA-N 0.000 claims description 4
RTTNCLLPAICZHA-UHFFFAOYSA-N 4-[3-(trifluoromethyl)pyridin-2-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound FC(F)(F)C1=CC=CN=C1N1C(C2)CCCN2CC1 RTTNCLLPAICZHA-UHFFFAOYSA-N 0.000 claims description 4
GQKWBHVDNMGZDG-UHFFFAOYSA-N 4-[3-(trifluoromethyl)pyridin-2-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound FC(F)(F)C1=CC=CN=C1N1C(CC2)CCCN2CC1 GQKWBHVDNMGZDG-UHFFFAOYSA-N 0.000 claims description 4
DOWIGBPKOCELEM-UHFFFAOYSA-N 4-[5-(2-fluorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound FC1=CC=CC=C1C1=CN=CC(N2C3CCN(C3)CC2)=C1 DOWIGBPKOCELEM-UHFFFAOYSA-N 0.000 claims description 4
YRXCFAOQHQRJKQ-UHFFFAOYSA-N 4-[5-(2-fluorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound FC1=CC=CC=C1C1=CN=CC(N2C3CCCN(CC3)CC2)=C1 YRXCFAOQHQRJKQ-UHFFFAOYSA-N 0.000 claims description 4
CZYIWVGHQDJXMU-UHFFFAOYSA-N 4-[5-(2-methoxyphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound COC1=CC=CC=C1C1=CN=CC(N2C3CCCN(CC3)CC2)=C1 CZYIWVGHQDJXMU-UHFFFAOYSA-N 0.000 claims description 4
FIPBHJQOBJCWDX-UHFFFAOYSA-N 4-[5-(2-methylphenyl)pyridin-2-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound CC1=CC=CC=C1C1=CC=C(N2C3CCCN(C3)CC2)N=C1 FIPBHJQOBJCWDX-UHFFFAOYSA-N 0.000 claims description 4
PHCGMSZMSRENMQ-UHFFFAOYSA-N 4-[5-(3-chlorophenyl)pyridin-2-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound ClC1=CC=CC(C=2C=NC(=CC=2)N2C3CCN(C3)CC2)=C1 PHCGMSZMSRENMQ-UHFFFAOYSA-N 0.000 claims description 4
OWEDYSYZJDEVOH-UHFFFAOYSA-N 4-[5-(3-chlorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound ClC1=CC=CC(C=2C=C(C=NC=2)N2C3CCCN(CC3)CC2)=C1 OWEDYSYZJDEVOH-UHFFFAOYSA-N 0.000 claims description 4
VWGICUSWTVBFJS-UHFFFAOYSA-N 4-[5-(3-fluorophenyl)pyridin-2-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound FC1=CC=CC(C=2C=NC(=CC=2)N2C3CCN(C3)CC2)=C1 VWGICUSWTVBFJS-UHFFFAOYSA-N 0.000 claims description 4
NWQBKZPHCONCJD-UHFFFAOYSA-N 4-[5-(3-fluorophenyl)pyridin-2-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound FC1=CC=CC(C=2C=NC(=CC=2)N2C3CCCN(CC3)CC2)=C1 NWQBKZPHCONCJD-UHFFFAOYSA-N 0.000 claims description 4
SGYKUBRQFGDPGE-UHFFFAOYSA-N 4-[5-(3-methoxyphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound COC1=CC=CC(C=2C=C(C=NC=2)N2C3CCN(C3)CC2)=C1 SGYKUBRQFGDPGE-UHFFFAOYSA-N 0.000 claims description 4
PZEQKMGBTHWMCG-UHFFFAOYSA-N 4-[5-(3-methoxyphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound COC1=CC=CC(C=2C=C(C=NC=2)N2C3CCCN(C3)CC2)=C1 PZEQKMGBTHWMCG-UHFFFAOYSA-N 0.000 claims description 4
DEDHFECZOZINJE-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)pyridin-2-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(N2C3CCCN(C3)CC2)N=C1 DEDHFECZOZINJE-UHFFFAOYSA-N 0.000 claims description 4
ZUQLXECGKJQGGY-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound C1=CC(Cl)=CC=C1C1=CN=CC(N2C3CCN(C3)CC2)=C1 ZUQLXECGKJQGGY-UHFFFAOYSA-N 0.000 claims description 4
GNYSTCYGKBWDSS-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound C1=CC(Cl)=CC=C1C1=CN=CC(N2C3CCCN(C3)CC2)=C1 GNYSTCYGKBWDSS-UHFFFAOYSA-N 0.000 claims description 4
CSGLMXWLMUVABY-UHFFFAOYSA-N 4-[5-(4-chlorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound C1=CC(Cl)=CC=C1C1=CN=CC(N2C3CCCN(CC3)CC2)=C1 CSGLMXWLMUVABY-UHFFFAOYSA-N 0.000 claims description 4
PATOATUNXZUKGT-UHFFFAOYSA-N 4-[5-(4-methoxyphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound C1=CC(OC)=CC=C1C1=CN=CC(N2C3CCCN(CC3)CC2)=C1 PATOATUNXZUKGT-UHFFFAOYSA-N 0.000 claims description 4
YNTABVZBZZBFRO-UHFFFAOYSA-N 4-[5-(trifluoromethyl)pyridin-3-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound FC(F)(F)C1=CN=CC(N2C3CCN(C3)CC2)=C1 YNTABVZBZZBFRO-UHFFFAOYSA-N 0.000 claims description 4
MSWQAAKLFQYFIE-UHFFFAOYSA-N 4-[5-[3-(trifluoromethyl)phenyl]pyridin-2-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound FC(F)(F)C1=CC=CC(C=2C=NC(=CC=2)N2C3CCN(C3)CC2)=C1 MSWQAAKLFQYFIE-UHFFFAOYSA-N 0.000 claims description 4
AHEYFDCFKXVFLU-UHFFFAOYSA-N 4-[5-[3-(trifluoromethyl)phenyl]pyridin-2-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound FC(F)(F)C1=CC=CC(C=2C=NC(=CC=2)N2C3CCCN(C3)CC2)=C1 AHEYFDCFKXVFLU-UHFFFAOYSA-N 0.000 claims description 4
TVZNQVUXEBUBQC-UHFFFAOYSA-N 4-pyrazin-2-yl-1,4-diazabicyclo[3.2.1]octane Chemical compound C1CN(CC2)CC1N2C1=CN=CC=N1 TVZNQVUXEBUBQC-UHFFFAOYSA-N 0.000 claims description 4
GATSHDMHXNTLRV-UHFFFAOYSA-N 4-pyridin-2-yl-1,4-diazabicyclo[3.3.2]decane Chemical compound C1CCC2CCN1CCN2C1=CC=CC=N1 GATSHDMHXNTLRV-UHFFFAOYSA-N 0.000 claims description 4
XXXSOCVFCZJMLD-UHFFFAOYSA-N 4-pyridin-3-yl-1,4-diazabicyclo[3.3.2]decane Chemical compound C1CCC2CCN1CCN2C1=CC=CN=C1 XXXSOCVFCZJMLD-UHFFFAOYSA-N 0.000 claims description 4
CATCPXNWJFCILI-UHFFFAOYSA-N 4-pyrimidin-5-yl-1,4-diazabicyclo[3.3.1]nonane Chemical compound C1CCC2CN1CCN2C1=CN=CN=C1 CATCPXNWJFCILI-UHFFFAOYSA-N 0.000 claims description 4
YKUMCNKAZPIFJD-UHFFFAOYSA-N 5-(1,4-diazabicyclo[3.3.2]decan-4-yl)pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(N2C3CCCN(CC3)CC2)=C1 YKUMCNKAZPIFJD-UHFFFAOYSA-N 0.000 claims description 4
MNOULQLXILYKNV-UHFFFAOYSA-N 5-[4-(trifluoromethyl)phenyl]-1h-pyrazole Chemical group C1=CC(C(F)(F)F)=CC=C1C1=CC=NN1 MNOULQLXILYKNV-UHFFFAOYSA-N 0.000 claims description 4
208000005298 acute pain Diseases 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
230000006999 cognitive decline Effects 0.000 claims description 4
WFXILIYPEXBRSH-UHFFFAOYSA-N ethyl 5-(1,4-diazabicyclo[3.3.2]decan-4-yl)pyridine-3-carboxylate Chemical compound CCOC(=O)C1=CN=CC(N2C3CCCN(CC3)CC2)=C1 WFXILIYPEXBRSH-UHFFFAOYSA-N 0.000 claims description 4
125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
PZLXMKKMMUZJGW-UHFFFAOYSA-N 3-(1,4-diazabicyclo[3.3.1]nonan-4-yl)quinoline Chemical compound C1=CC=CC2=CC(N3CCN4CC3CCC4)=CN=C21 PZLXMKKMMUZJGW-UHFFFAOYSA-N 0.000 claims description 3
HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 claims description 3
NXJSCIXIOSMADJ-UHFFFAOYSA-N 4-(5-bromopyridin-2-yl)-1,4-diazabicyclo[3.2.1]octane Chemical compound N1=CC(Br)=CC=C1N1C(C2)CCN2CC1 NXJSCIXIOSMADJ-UHFFFAOYSA-N 0.000 claims description 3
HMRNFWXWPOKOJT-UHFFFAOYSA-N 4-(6-methoxypyridin-2-yl)-1,4-diazabicyclo[3.2.1]octane Chemical compound COC1=CC=CC(N2C3CCN(C3)CC2)=N1 HMRNFWXWPOKOJT-UHFFFAOYSA-N 0.000 claims description 3
QNESBMMNVFEIPH-UHFFFAOYSA-N 4-(6-methoxypyridin-2-yl)-1,4-diazabicyclo[3.3.1]nonane Chemical compound COC1=CC=CC(N2C3CCCN(C3)CC2)=N1 QNESBMMNVFEIPH-UHFFFAOYSA-N 0.000 claims description 3
CTBCKNFETQBXOR-UHFFFAOYSA-N 4-(6-methylpyridin-3-yl)-1,4-diazabicyclo[3.3.1]nonane Chemical compound C1=NC(C)=CC=C1N1C(C2)CCCN2CC1 CTBCKNFETQBXOR-UHFFFAOYSA-N 0.000 claims description 3
FMLGWRTUSSURJM-UHFFFAOYSA-N 4-(6-phenylpyridazin-3-yl)-1,4-diazabicyclo[3.3.1]nonane Chemical compound C1CCC2CN1CCN2C(N=N1)=CC=C1C1=CC=CC=C1 FMLGWRTUSSURJM-UHFFFAOYSA-N 0.000 claims description 3
QLCTVCKMVZULBL-UHFFFAOYSA-N 4-[2-methyl-5-(trifluoromethyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound CC1=NC=C(C(F)(F)F)C=C1N1C(CC2)CCCN2CC1 QLCTVCKMVZULBL-UHFFFAOYSA-N 0.000 claims description 3
CLAJZAITPOWRSR-UHFFFAOYSA-N 4-[5-(2-methoxyphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound COC1=CC=CC=C1C1=CN=CC(N2C3CCCN(C3)CC2)=C1 CLAJZAITPOWRSR-UHFFFAOYSA-N 0.000 claims description 3
LOZAXNVJUXOXKM-UHFFFAOYSA-N 4-[5-(3-chlorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound ClC1=CC=CC(C=2C=C(C=NC=2)N2C3CCN(C3)CC2)=C1 LOZAXNVJUXOXKM-UHFFFAOYSA-N 0.000 claims description 3
KOEMCGGITQTPGG-UHFFFAOYSA-N 4-[5-(3-methoxyphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound COC1=CC=CC(C=2C=C(C=NC=2)N2C3CCCN(CC3)CC2)=C1 KOEMCGGITQTPGG-UHFFFAOYSA-N 0.000 claims description 3
QFWWZJTZMALTNZ-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound C1=CC(F)=CC=C1C1=CN=CC(N2C3CCCN(C3)CC2)=C1 QFWWZJTZMALTNZ-UHFFFAOYSA-N 0.000 claims description 3
KMFLGPNBXRWLTJ-UHFFFAOYSA-N 4-[5-(4-methylphenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound C1=CC(C)=CC=C1C1=CN=CC(N2C3CCCN(C3)CC2)=C1 KMFLGPNBXRWLTJ-UHFFFAOYSA-N 0.000 claims description 3
PETKNFCTCMWSSD-UHFFFAOYSA-N 4-[5-(trifluoromethyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound FC(F)(F)C1=CN=CC(N2C3CCCN(CC3)CC2)=C1 PETKNFCTCMWSSD-UHFFFAOYSA-N 0.000 claims description 3
MCWCWFDBPBHUBW-UHFFFAOYSA-N 4-[5-[2-(trifluoromethyl)phenyl]pyridin-3-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound FC(F)(F)C1=CC=CC=C1C1=CN=CC(N2C3CCN(C3)CC2)=C1 MCWCWFDBPBHUBW-UHFFFAOYSA-N 0.000 claims description 3
FDAGKRXXAOODGQ-UHFFFAOYSA-N 4-[5-[2-(trifluoromethyl)phenyl]pyridin-3-yl]-1,4-diazabicyclo[3.3.1]nonane Chemical compound FC(F)(F)C1=CC=CC=C1C1=CN=CC(N2C3CCCN(C3)CC2)=C1 FDAGKRXXAOODGQ-UHFFFAOYSA-N 0.000 claims description 3
MVPJDIFWGXJIHG-UHFFFAOYSA-N 4-[5-[4-(trifluoromethyl)phenyl]pyridin-3-yl]-1,4-diazabicyclo[3.3.2]decane Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CN=CC(N2C3CCCN(CC3)CC2)=C1 MVPJDIFWGXJIHG-UHFFFAOYSA-N 0.000 claims description 3
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 claims description 3
SCYFOVZSDZGGNK-UHFFFAOYSA-N 4-pyridin-2-yl-1,4-diazabicyclo[3.2.1]octane Chemical compound C1CN(CC2)CC1N2C1=CC=CC=N1 SCYFOVZSDZGGNK-UHFFFAOYSA-N 0.000 claims description 3
BFLSVNMSHDCZEX-UHFFFAOYSA-N 4-pyridin-3-yl-1,4-diazabicyclo[3.2.1]octane Chemical compound C1CN(CC2)CC1N2C1=CC=CN=C1 BFLSVNMSHDCZEX-UHFFFAOYSA-N 0.000 claims description 3
XWDAADAHKJPVRC-UHFFFAOYSA-N 4-pyridin-3-yl-1,4-diazabicyclo[3.3.1]nonane Chemical compound C1CCC2CN1CCN2C1=CC=CN=C1 XWDAADAHKJPVRC-UHFFFAOYSA-N 0.000 claims description 3
UYYLURCEMVZEDK-UHFFFAOYSA-N 4-pyridin-4-yl-1,4-diazabicyclo[3.2.1]octane Chemical compound C1CN(CC2)CC1N2C1=CC=NC=C1 UYYLURCEMVZEDK-UHFFFAOYSA-N 0.000 claims description 3
JUFJEWIVSQVZIF-UHFFFAOYSA-N 4-quinolin-3-yl-1,4-diazabicyclo[3.3.2]decane Chemical compound C1CN(CC2)CCCC1N2C1=CN=C(C=CC=C2)C2=C1 JUFJEWIVSQVZIF-UHFFFAOYSA-N 0.000 claims description 3
LRMIIBSFVUAXQM-UHFFFAOYSA-N 5-(1,4-diazabicyclo[3.3.1]nonan-4-yl)pyridine-3-carbonitrile Chemical compound N#CC1=CN=CC(N2C3CCCN(C3)CC2)=C1 LRMIIBSFVUAXQM-UHFFFAOYSA-N 0.000 claims description 3
150000003254 radicals Chemical class 0.000 claims description 3
IAZOEQQOFGUKSQ-UHFFFAOYSA-N 4-(3-bromophenyl)-1,4-diazabicyclo[3.3.3]undecane Chemical compound BrC1=CC=CC(N2C3CCCN(CCC3)CC2)=C1 IAZOEQQOFGUKSQ-UHFFFAOYSA-N 0.000 claims description 2
QGIPWZDOYQJFRS-UHFFFAOYSA-N 4-(5-bromopyridin-2-yl)-1,4-diazabicyclo[3.3.3]undecane Chemical compound N1=CC(Br)=CC=C1N1C(CCC2)CCCN2CC1 QGIPWZDOYQJFRS-UHFFFAOYSA-N 0.000 claims description 2
ICLUZMFAJXBWPU-UHFFFAOYSA-N 4-(5-chloropyridin-2-yl)-1,4-diazabicyclo[3.3.3]undecane Chemical compound N1=CC(Cl)=CC=C1N1C(CCC2)CCCN2CC1 ICLUZMFAJXBWPU-UHFFFAOYSA-N 0.000 claims description 2
KXRVVSCDCYJFJA-UHFFFAOYSA-N 4-(5-chloropyridin-3-yl)-1,4-diazabicyclo[3.1.1]heptane Chemical compound ClC1=CN=CC(N2C3CN(C3)CC2)=C1 KXRVVSCDCYJFJA-UHFFFAOYSA-N 0.000 claims description 2
JHTFYWLOHCBAQL-UHFFFAOYSA-N 4-(5-methoxypyridin-3-yl)-1,4-diazabicyclo[3.1.1]heptane Chemical compound COC1=CN=CC(N2C3CN(C3)CC2)=C1 JHTFYWLOHCBAQL-UHFFFAOYSA-N 0.000 claims description 2
GEKYPDQKOYYENZ-UHFFFAOYSA-N 4-(5-methoxypyridin-3-yl)-1,4-diazabicyclo[3.3.1]nonane Chemical compound COC1=CN=CC(N2C3CCCN(C3)CC2)=C1 GEKYPDQKOYYENZ-UHFFFAOYSA-N 0.000 claims description 2
MHUAOHUWXYXYHK-UHFFFAOYSA-N 4-(5-methoxypyridin-3-yl)-1,4-diazabicyclo[3.3.3]undecane Chemical compound COC1=CN=CC(N2C3CCCN(CCC3)CC2)=C1 MHUAOHUWXYXYHK-UHFFFAOYSA-N 0.000 claims description 2
YSTAKVPJFKYLJH-UHFFFAOYSA-N 4-(5-phenylpyridazin-3-yl)-1,4-diazabicyclo[3.1.1]heptane Chemical compound C1C2CN1CCN2C(N=NC=1)=CC=1C1=CC=CC=C1 YSTAKVPJFKYLJH-UHFFFAOYSA-N 0.000 claims description 2
FNPXNIMZTLVYSN-UHFFFAOYSA-N 4-(5-phenylpyridazin-3-yl)-1,4-diazabicyclo[3.3.3]undecane Chemical compound C1CCC2CCCN1CCN2C(N=NC=1)=CC=1C1=CC=CC=C1 FNPXNIMZTLVYSN-UHFFFAOYSA-N 0.000 claims description 2
NMDGJVIKDURESY-UHFFFAOYSA-N 4-(6-methoxypyridin-2-yl)-1,4-diazabicyclo[3.3.3]undecane Chemical compound COC1=CC=CC(N2C3CCCN(CCC3)CC2)=N1 NMDGJVIKDURESY-UHFFFAOYSA-N 0.000 claims description 2
XQAWFXFXLGDFBI-UHFFFAOYSA-N 4-(6-methylpyridin-3-yl)-1,4-diazabicyclo[3.2.1]octane Chemical compound C1=NC(C)=CC=C1N1C(C2)CCN2CC1 XQAWFXFXLGDFBI-UHFFFAOYSA-N 0.000 claims description 2
FRSDCGTUTGCTPE-UHFFFAOYSA-N 4-(6-methylpyridin-3-yl)-1,4-diazabicyclo[3.3.3]undecane Chemical compound C1=NC(C)=CC=C1N1C(CCC2)CCCN2CC1 FRSDCGTUTGCTPE-UHFFFAOYSA-N 0.000 claims description 2
YEZBHORJGQSWBB-UHFFFAOYSA-N 4-(6-phenylpyridazin-3-yl)-1,4-diazabicyclo[3.3.3]undecane Chemical compound C1CCC2CCCN1CCN2C(N=N1)=CC=C1C1=CC=CC=C1 YEZBHORJGQSWBB-UHFFFAOYSA-N 0.000 claims description 2
HUUQVDMXFJWIFG-UHFFFAOYSA-N 4-[5-(2,4-dichlorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.2.1]octane Chemical compound ClC1=CC(Cl)=CC=C1C1=CN=CC(N2C3CCN(C3)CC2)=C1 HUUQVDMXFJWIFG-UHFFFAOYSA-N 0.000 claims description 2
IWFKITHVLUBRPA-UHFFFAOYSA-N 4-[5-(2,4-dichlorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.3]undecane Chemical compound ClC1=CC(Cl)=CC=C1C1=CN=CC(N2C3CCCN(CCC3)CC2)=C1 IWFKITHVLUBRPA-UHFFFAOYSA-N 0.000 claims description 2
YIWNDVZJICJRAP-UHFFFAOYSA-N 4-[5-(2-fluorophenyl)pyridin-3-yl]-1,4-diazabicyclo[3.3.3]undecane Chemical compound FC1=CC=CC=C1C1=CN=CC(N2C3CCCN(CCC3)CC2)=C1 YIWNDVZJICJRAP-UHFFFAOYSA-N 0.000 claims description 2
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