JP2008513405A5 - - Google Patents
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- JP2008513405A5 JP2008513405A5 JP2007531711A JP2007531711A JP2008513405A5 JP 2008513405 A5 JP2008513405 A5 JP 2008513405A5 JP 2007531711 A JP2007531711 A JP 2007531711A JP 2007531711 A JP2007531711 A JP 2007531711A JP 2008513405 A5 JP2008513405 A5 JP 2008513405A5
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- JP
- Japan
- Prior art keywords
- piperidinyl
- methyl
- alkyl
- methylethyl
- cyclobutyl
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 7
- -1 5- {4-[(1-cyclobutyl-4-piperidinyl) methyl] -1-piperidinyl} -2-pyridinecarboxylic acid hydrochloride Chemical compound 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- GSGFPGAEHOFDPV-UHFFFAOYSA-N 1-[4-[4-[(1-cyclobutylpiperidin-4-yl)methyl]piperidin-1-yl]phenyl]-2,2,2-trifluoroethanone Chemical compound C1=CC(C(=O)C(F)(F)F)=CC=C1N1CCC(CC2CCN(CC2)C2CCC2)CC1 GSGFPGAEHOFDPV-UHFFFAOYSA-N 0.000 claims 1
- JXDITEKFBWFLLS-UHFFFAOYSA-N 1-[4-[4-[(1-cyclobutylpiperidin-4-yl)methyl]piperidin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1CCC(CC2CCN(CC2)C2CCC2)CC1 JXDITEKFBWFLLS-UHFFFAOYSA-N 0.000 claims 1
- UCPDJKHTNBJISS-UHFFFAOYSA-N 1-[4-[4-[(1-ethylpiperidin-4-yl)methyl]piperidin-1-yl]phenyl]ethanone Chemical compound C1CN(CC)CCC1CC1CCN(C=2C=CC(=CC=2)C(C)=O)CC1 UCPDJKHTNBJISS-UHFFFAOYSA-N 0.000 claims 1
- AFMJVPLQQBTRFN-UHFFFAOYSA-N 1-[4-[4-[(1-methylpiperidin-4-yl)methyl]piperidin-1-yl]phenyl]ethanone Chemical compound C1CN(C)CCC1CC1CCN(C=2C=CC(=CC=2)C(C)=O)CC1 AFMJVPLQQBTRFN-UHFFFAOYSA-N 0.000 claims 1
- CZJWVSHDNBSENK-UHFFFAOYSA-N 1-[4-[4-[(1-propan-2-ylpiperidin-4-yl)methyl]piperidin-1-yl]phenyl]ethanone Chemical compound C1CN(C(C)C)CCC1CC1CCN(C=2C=CC(=CC=2)C(C)=O)CC1 CZJWVSHDNBSENK-UHFFFAOYSA-N 0.000 claims 1
- ULBXCFSIFQJEQV-UHFFFAOYSA-N 1-[4-[4-[[1-(cyclopropylmethyl)piperidin-4-yl]methyl]piperidin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1CCC(CC2CCN(CC3CC3)CC2)CC1 ULBXCFSIFQJEQV-UHFFFAOYSA-N 0.000 claims 1
- YNUMGPGJIZSXSX-UHFFFAOYSA-N 1-[5-[4-[(1-cyclobutylpiperidin-4-yl)methyl]piperidin-1-yl]pyridin-2-yl]ethanone Chemical compound C1=NC(C(=O)C)=CC=C1N1CCC(CC2CCN(CC2)C2CCC2)CC1 YNUMGPGJIZSXSX-UHFFFAOYSA-N 0.000 claims 1
- XESYQFVZWPXMEF-UHFFFAOYSA-N 1-[5-[4-[(1-propan-2-ylpiperidin-4-yl)methyl]piperidin-1-yl]pyridin-2-yl]ethanone Chemical compound C1CN(C(C)C)CCC1CC1CCN(C=2C=NC(=CC=2)C(C)=O)CC1 XESYQFVZWPXMEF-UHFFFAOYSA-N 0.000 claims 1
- SHKCFQVJQJJJJW-UHFFFAOYSA-N 1-[6-[4-[(1-cyclobutylpiperidin-4-yl)methyl]piperidin-1-yl]pyridin-3-yl]ethanone Chemical compound N1=CC(C(=O)C)=CC=C1N1CCC(CC2CCN(CC2)C2CCC2)CC1 SHKCFQVJQJJJJW-UHFFFAOYSA-N 0.000 claims 1
- YRTZPTVSZHFDEY-UHFFFAOYSA-N 1-[6-[4-[(1-propan-2-ylpiperidin-4-yl)methyl]piperidin-1-yl]pyridin-3-yl]ethanone Chemical compound C1CN(C(C)C)CCC1CC1CCN(C=2N=CC(=CC=2)C(C)=O)CC1 YRTZPTVSZHFDEY-UHFFFAOYSA-N 0.000 claims 1
- UAIVAUOJPSJQDH-UHFFFAOYSA-N 3-[4-[(1-cyclobutylpiperidin-4-yl)methyl]piperidin-1-yl]-6-(trifluoromethyl)pyridazine Chemical compound N1=NC(C(F)(F)F)=CC=C1N1CCC(CC2CCN(CC2)C2CCC2)CC1 UAIVAUOJPSJQDH-UHFFFAOYSA-N 0.000 claims 1
- UNVRCIYSLCUMOB-UHFFFAOYSA-N 3-methyl-5-[4-[4-[(1-propan-2-ylpiperidin-4-yl)methyl]piperidin-1-yl]phenyl]-1,2,4-oxadiazole Chemical compound C1CN(C(C)C)CCC1CC1CCN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 UNVRCIYSLCUMOB-UHFFFAOYSA-N 0.000 claims 1
- PFMNQJRTADLGGT-UHFFFAOYSA-N 3-methyl-5-[5-[4-[(1-propan-2-ylpiperidin-4-yl)methyl]piperidin-1-yl]pyridin-2-yl]-1,2,4-oxadiazole Chemical compound C1CN(C(C)C)CCC1CC1CCN(C=2C=NC(=CC=2)C=2ON=C(C)N=2)CC1 PFMNQJRTADLGGT-UHFFFAOYSA-N 0.000 claims 1
- PQQIDKJXTQPNSK-UHFFFAOYSA-N 5-[2-fluoro-4-[4-[(1-propan-2-ylpiperidin-4-yl)methyl]piperidin-1-yl]phenyl]-3-methyl-1,2,4-oxadiazole Chemical compound C1CN(C(C)C)CCC1CC1CCN(C=2C=C(F)C(C=3ON=C(C)N=3)=CC=2)CC1 PQQIDKJXTQPNSK-UHFFFAOYSA-N 0.000 claims 1
- KWOGQINTOGSLFN-UHFFFAOYSA-N 5-[3-fluoro-4-[4-[(1-propan-2-ylpiperidin-4-yl)methyl]piperidin-1-yl]phenyl]-3-methyl-1,2,4-oxadiazole Chemical compound C1CN(C(C)C)CCC1CC1CCN(C=2C(=CC(=CC=2)C=2ON=C(C)N=2)F)CC1 KWOGQINTOGSLFN-UHFFFAOYSA-N 0.000 claims 1
- KPRASRCQBQNYCU-UHFFFAOYSA-N 5-[4-[(1-cyclobutylpiperidin-4-yl)methyl]piperidin-1-yl]-2-(trifluoromethyl)pyrimidine Chemical compound C1=NC(C(F)(F)F)=NC=C1N1CCC(CC2CCN(CC2)C2CCC2)CC1 KPRASRCQBQNYCU-UHFFFAOYSA-N 0.000 claims 1
- CMAQNUSSBJKQOA-UHFFFAOYSA-N 5-[4-[(1-cyclobutylpiperidin-4-yl)methyl]piperidin-1-yl]-n-ethylpyrazine-2-carboxamide Chemical compound C1=NC(C(=O)NCC)=CN=C1N1CCC(CC2CCN(CC2)C2CCC2)CC1 CMAQNUSSBJKQOA-UHFFFAOYSA-N 0.000 claims 1
- YVORDKMQWSIKJB-UHFFFAOYSA-N 5-[4-[(1-cyclobutylpiperidin-4-yl)methyl]piperidin-1-yl]-n-methylpyrazine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CN=C1N1CCC(CC2CCN(CC2)C2CCC2)CC1 YVORDKMQWSIKJB-UHFFFAOYSA-N 0.000 claims 1
- JMFMUYSGFMKHHG-UHFFFAOYSA-N 5-[4-[(1-cyclobutylpiperidin-4-yl)methyl]piperidin-1-yl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1N1CCC(CC2CCN(CC2)C2CCC2)CC1 JMFMUYSGFMKHHG-UHFFFAOYSA-N 0.000 claims 1
- CFAFAIASRGBKNN-UHFFFAOYSA-N 5-[4-[(1-cyclobutylpiperidin-4-yl)methyl]piperidin-1-yl]-n-propan-2-ylpyrazine-2-carboxamide Chemical compound C1=NC(C(=O)NC(C)C)=CN=C1N1CCC(CC2CCN(CC2)C2CCC2)CC1 CFAFAIASRGBKNN-UHFFFAOYSA-N 0.000 claims 1
- SEAMETQZVVSBAG-UHFFFAOYSA-N 5-[4-[(1-cyclobutylpiperidin-4-yl)methyl]piperidin-1-yl]pyrazine-2-carboxylic acid;hydrochloride Chemical compound Cl.C1=NC(C(=O)O)=CN=C1N1CCC(CC2CCN(CC2)C2CCC2)CC1 SEAMETQZVVSBAG-UHFFFAOYSA-N 0.000 claims 1
- FRWCBKJOSQVOOJ-UHFFFAOYSA-N 5-[4-[(1-cyclobutylpiperidin-4-yl)methyl]piperidin-1-yl]pyridine-2-carbonitrile Chemical compound C1=NC(C#N)=CC=C1N1CCC(CC2CCN(CC2)C2CCC2)CC1 FRWCBKJOSQVOOJ-UHFFFAOYSA-N 0.000 claims 1
- GIDQEHZBYYQURN-UHFFFAOYSA-N 5-[4-[(1-propan-2-ylpiperidin-4-yl)methyl]piperidin-1-yl]pyridine-2-carbonitrile Chemical compound C1CN(C(C)C)CCC1CC1CCN(C=2C=NC(=CC=2)C#N)CC1 GIDQEHZBYYQURN-UHFFFAOYSA-N 0.000 claims 1
- WYJAFEMOKMNDPM-UHFFFAOYSA-N 5-[4-[4-[[1-(cyclopropylmethyl)piperidin-4-yl]methyl]piperidin-1-yl]phenyl]-3-methyl-1,2,4-oxadiazole Chemical compound CC1=NOC(C=2C=CC(=CC=2)N2CCC(CC3CCN(CC4CC4)CC3)CC2)=N1 WYJAFEMOKMNDPM-UHFFFAOYSA-N 0.000 claims 1
- FCQBKRBJRHKGOV-UHFFFAOYSA-N 5-[5-[4-[(1-cyclobutylpiperidin-4-yl)methyl]piperidin-1-yl]pyridin-2-yl]-3-methyl-1,2,4-oxadiazole Chemical compound CC1=NOC(C=2N=CC(=CC=2)N2CCC(CC3CCN(CC3)C3CCC3)CC2)=N1 FCQBKRBJRHKGOV-UHFFFAOYSA-N 0.000 claims 1
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 1
- OBOLYNQLHKRMQA-UHFFFAOYSA-N C1=CC=C(C=C1)ON(C(=O)C2=CC=CC=C2OS(=O)(=O)C3=CC=CC=C3)NS(=O)(=O)C4=CC=CC=C4 Chemical compound C1=CC=C(C=C1)ON(C(=O)C2=CC=CC=C2OS(=O)(=O)C3=CC=CC=C3)NS(=O)(=O)C4=CC=CC=C4 OBOLYNQLHKRMQA-UHFFFAOYSA-N 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- ZAZJSJFQRJUTAM-UHFFFAOYSA-N methyl 5-[4-[(1-cyclobutylpiperidin-4-yl)methyl]piperidin-1-yl]pyrazine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CN=C1N1CCC(CC2CCN(CC2)C2CCC2)CC1 ZAZJSJFQRJUTAM-UHFFFAOYSA-N 0.000 claims 1
- JVKYGIDHSJKVLD-UHFFFAOYSA-N methyl 5-[4-[(1-propan-2-ylpiperidin-4-yl)methyl]piperidin-1-yl]pyrazine-2-carboxylate Chemical compound C1=NC(C(=O)OC)=CN=C1N1CCC(CC2CCN(CC2)C(C)C)CC1 JVKYGIDHSJKVLD-UHFFFAOYSA-N 0.000 claims 1
- HQWBBOSFFWMGDV-UHFFFAOYSA-N n-propan-2-yl-5-[4-[(1-propan-2-ylpiperidin-4-yl)methyl]piperidin-1-yl]pyrazine-2-carboxamide Chemical compound C1=NC(C(=O)NC(C)C)=CN=C1N1CCC(CC2CCN(CC2)C(C)C)CC1 HQWBBOSFFWMGDV-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- SLLOIKKWMOLTEF-UHFFFAOYSA-N tert-butyl 5-[4-[(1-cyclobutylpiperidin-4-yl)methyl]piperidin-1-yl]pyridine-2-carboxylate Chemical compound C1=NC(C(=O)OC(C)(C)C)=CC=C1N1CCC(CC2CCN(CC2)C2CCC2)CC1 SLLOIKKWMOLTEF-UHFFFAOYSA-N 0.000 claims 1
- WVNSMDASXXXKQL-UHFFFAOYSA-N tert-butyl 5-[4-[(1-propan-2-ylpiperidin-4-yl)methyl]piperidin-1-yl]pyridine-2-carboxylate Chemical compound C1CN(C(C)C)CCC1CC1CCN(C=2C=NC(=CC=2)C(=O)OC(C)(C)C)CC1 WVNSMDASXXXKQL-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Claims (8)
- 式(I):
[式中:
R1は、アリール、ヘテロアリール、−アリール−X−アリール、−アリール−X−ヘテロアリール、−アリール−X−ヘテロシクリル、−ヘテロアリール−X−ヘテロアリール、−ヘテロアリール−X−アリールまたは−ヘテロアリール−X−ヘテロシクリルであり;
ここで、R1のアリール、ヘテロアリールおよびヘテロシクリル基は、1個または複数の(例えば、1、2または3個の)置換基により置換されていてもよく、該置換基は、同じであってもまたは異なっていてもよく、ならびにハロゲン、ヒドロキシ、シアノ、ニトロ、オキソ、ハロC1−6アルキル、ポリハロC1−6アルキル、ハロC1−6アルコキシ、ポリハロC1−6アルコキシ、C1−6アルキル、C1−6アルコキシ、C1−6アルキルチオ、C1−6アルコキシC1−6アルキル、C3−7シクロアルキルC1−6アルコキシ、C1−6アルキルスルホニル、C1−6アルキルスルフィニル、C1−6アルキルスルホニルオキシ、C1−6アルキルスルホニルC1−6アルキル、C1−6アルキルスルホンアミドC1−6アルキル、C1−6アルキルアミドC1−6アルキル、フェニル、フェニルスルホニル、フェニルスルホニルオキシ、フェニルオキシ、フェニルスルホンアミド、フェニルカルボキサミド、フェノイルまたは−COR15、−COOR15、NR15R16、−CONR15R16、−NR15COR16、−NR15SO2R16または−SO2NR15R16基からなる群より選択され、ここで、R15およびR16は独立して、水素、C1−6アルキル、ハロC1−6アルキル、ポリハロC1−6アルキルまたはC3−6シクロアルキルであるか、または一緒になって複素環を形成し;
Xは、一の結合、O、CO、SO2、OCH2またはCH2Oであり;
R2は、C1−8アルキル、C3−6アルケニル、C3−6アルキニル、C3−6シクロアルキル、C5−6シクロアルケニルまたは−C1−4アルキル−C3−6シクロアルキルであり;
ここで、R2のC3−6シクロアルキル基は、1個または複数の(例えば、1、2または3個の)置換基により置換されていてもよく、該置換基は、同じであってもまたは異なっていてもよく、ならびにハロゲン、C1−4アルキルまたはポリハロC1−6アルキル基からなる群より選択され;
各R3およびR4基は独立してC1−4アルキルであり;
mおよびnは独立して0、1または2である]
の化合物またはその医薬上許容される塩またはその溶媒和物。 - R1が、−アリール、−ヘテロアリール、−アリール−X−ヘテロアリールまたはヘテロアリール−X−ヘテロアリールである、請求項1記載の化合物。
- Xが一の結合である、請求項1または請求項2記載の化合物。
- R2が、C1−8アルキル、C3−6シクロアルキルまたはC1−4アルキル−C3−6シクロアルキルである、前記請求項いずれかに記載の化合物。
- mおよびnが共に0である、前記請求項いずれかに記載の化合物。
- 5−{4−[(1−シクロブチル−4−ピペリジニル)メチル]−1−ピペリジニル}−2−ピラジンカルボン酸メチル;
5−(4−{[1−(1−メチルエチル)−4−ピペリジニル]メチル}−1−ピペリジニル)−2−ピラジンカルボン酸メチル;
5−{4−[(1−シクロブチル−4−ピペリジニル)メチル]−1−ピペリジニル}−2−ピリジンカルボン酸1,1−ジメチルエチル;
5−(4−{[1−(1−メチルエチル)−4−ピペリジニル]メチル}−1−ピペリジニル)−2−ピリジンカルボン酸1,1−ジメチルエチル;
5−{4−[(1−シクロブチル−4−ピペリジニル)メチル]−1−ピペリジニル}−2−ピラジンカルボン酸塩酸塩;
5−{4−[(1−シクロブチル−4−ピペリジニル)メチル]−1−ピペリジニル}−N−(1−メチルエチル)−2−ピラジンカルボキサミド;
N−(1−メチルエチル)−5−(4−{[1−(1−メチルエチル)−4−ピペリジニル]メチル}−1−ピペリジニル)−2−ピラジンカルボキサミド;
5−{4−[(1−シクロブチル−4−ピペリジニル)メチル]−1−ピペリジニル}−N−メチル−2−ピラジンカルボキサミド;
5−{4−[(1−シクロブチル−4−ピペリジニル)メチル]−1−ピペリジニル}−N−エチル−2−ピラジンカルボキサミド;
5−{4−[(1−シクロブチル−4−ピペリジニル)メチル]−1−ピペリジニル}−2−ピリジンカルボン酸塩酸塩;
5−{4−[(1−シクロブチル−4−ピペリジニル)メチル]−1−ピペリジニル}−N−メチル−2−ピリジンカルボキサミド;
N−メチル−5−(4−{[1−(1−メチルエチル)−4−ピペリジニル]メチル}−1−ピペリジニル)−2−ピペリジンカルボキサミド;
1−(1−メチルエチル)−4−({1−[4−(3−メチル−1,2,4−オキサジアゾール−5−イル)フェニル]−4−ピペリジニル}メチル)ピペリジン;
1−[2−フルオロ−4−(3−メチル−1,2,4−オキサジアゾール−5−イル)フェニル]−4−{[1−(1−メチルエチル)−4−ピペリジニル]メチル}ピペリジン;
5−(4−{[1−(1−メチルエチル)−4−ピペリジニル]メチル}−1−ピペリジニル)−2−(3−メチル−1,2,4−オキサジアゾール−5−イル)ピリジン;
1−[3−フルオロ−4−(3−メチル−1,2,4−オキサジアゾール−5−イル)フェニル]−4−{[1−(1−メチルエチル)−4−ピペリジニル]メチル}ピペリジン;
5−{4−[(1−シクロブチル−4−ピペリジニル)メチル]−1−ピペリジニル}−2−(3−メチル−1,2,4−オキサジアゾール−5−イル)ピリジン;
1−エチル−4−({1−[4−(3−メチル−1,2,4−オキサジアゾール−5−イル)−4−ピペリジニル}メチル)ピペリジン;
1−(シクロプロピルメチル)−4−({1−[4−(3−メチル−1,2,4−オキサジアゾール−5−イル)フェニル]−4−ピペリジニル}メチル)ピペリジン;
1−メチル−4−({1−[4−(3メチル−1,2,4−オキサジアゾオール−5−イル)フェニル]−4−ピペリジニル}メチル)ピペリジン;
5−(4−{[1−(1−メチルエチル)−4−ピペリジニル]メチル}−1−ピペリジニル)−2−ピリジンカルボニトリル;
5−{4−[(1−シクロブチル−4−ピペリジニル)メチル]−1−ピペリジニル}−2−ピリジンカルボニトリル;
1−[5−(4−{[1−(1−メチルエチル)−4−ピペリジニル]メチル}−1−ピペリジニル)−2−ピリジニル]エタノン;
1−(5−{4−[(1−シクロブチル−4−ピペリジニル)メチル]−1−ピペリジニル}−2−ピリジニル)エタノン;
1−(4−{4−[(1−シクロブチル−4−ピペリジニル)メチル]−1−ピペリジニル}フェニル)エタノン;
1−[4−(4−{[1−(1−メチルエチル)−4−ピペリジニル]メチル}−1−ピペリジニル)フェニル]エタノン;
1−(4−{4−[(1−エチル−4−ピペリジニル)メチル]−1−ピペリジニル}フェニル)エタノン;
1−[4−(4−{[1−(1−シクロプロピルメチル)−4−ピペリジニル]メチル}−1−ピペリジニル)フェニル]エタノン;
1−(6−{4−[(1−シクロブチル−4−ピペリジニル)メチル]−1−ピペリジニル}−3−ピリジニル)エタノン;
1−[6−(4{[1−(1−メチルエチル)−4−ピペリジニル]メチル}−1−ピペリジニル)−3−ピリジニル]エタノン;
1−(4−{4−[(1−シクロブチル−4−ピペリジニル)メチル]−1−ピペリジニル}フェニル)−2,2,2−トリフルオロエタノン;
1−(4−{4−[(1−メチル−4−ピペリジニル)メチル]−1−ピペリジニル}フェニル)エタノン;
3−(4−{[1−(1−メチルエチル)−4−ピペリジニル]メチル}−1−ピペリジニル)−6−(トリフルオロメチル)ピリダシン;
3−{4−[(1−シクロブチル−4−ピペリジニル)メチル]−1−ピペリジニル}−6−(トリフルオロメチル)ピリダジン;
5−{4−[(1−シクロブチル−4−ピペリジニル)メチル]−1−ピペリジニル}−2−(トリフルオロメチル)ピリミジン;
5−(4−{[1−(1−メチルエチル)−4−ピペリジニル]メチル}−1−ピペリジニル)−2−(トリフルオロメチル)ピリミジン;の化合物またはその医薬上許容される塩または溶媒和物である、請求項1記載の化合物。 - 請求項1〜6いずれか1項に記載の式(I)の化合物またはその医薬上許容される塩または溶媒和物および医薬上許容される担体または賦形剤を含有する医薬組成物。
- 請求項1〜6いずれか1項に記載の式(I)の化合物またはその医薬上許容される塩または溶媒和物および医薬上許容される担体を含有する、神経系疾患の処置用の医薬組成物。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0420831A GB0420831D0 (en) | 2004-09-17 | 2004-09-17 | Novel compounds |
PCT/EP2005/010169 WO2006029906A1 (en) | 2004-09-17 | 2005-09-16 | Methylene dipiperidine derivatives |
Publications (2)
Publication Number | Publication Date |
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JP2008513405A JP2008513405A (ja) | 2008-05-01 |
JP2008513405A5 true JP2008513405A5 (ja) | 2008-10-16 |
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Application Number | Title | Priority Date | Filing Date |
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JP2007531711A Withdrawn JP2008513405A (ja) | 2004-09-17 | 2005-09-16 | メチレンジピペリジン誘導体 |
Country Status (8)
Country | Link |
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US (1) | US7638631B2 (ja) |
EP (1) | EP1789410B1 (ja) |
JP (1) | JP2008513405A (ja) |
AT (1) | ATE433966T1 (ja) |
DE (1) | DE602005015002D1 (ja) |
ES (1) | ES2326182T3 (ja) |
GB (1) | GB0420831D0 (ja) |
WO (1) | WO2006029906A1 (ja) |
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US9108948B2 (en) | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
NZ611323A (en) | 2006-06-23 | 2014-10-31 | Abbvie Bahamas Ltd | Cyclopropyl amine derivatives as histamin h3 receptor modulators |
EP2155689B1 (en) * | 2007-05-31 | 2015-07-08 | Boehringer Ingelheim International GmbH | Ccr2 receptor antagonists and uses thereof |
US20120053164A1 (en) | 2008-12-19 | 2012-03-01 | Boehringer Ingelheim International Gmbh | Cyclic pyrimidin-4-carboxamides as ccr2 receptor antagonists for treatment of inflammation, asthma and copd |
US9186353B2 (en) | 2009-04-27 | 2015-11-17 | Abbvie Inc. | Treatment of osteoarthritis pain |
US20120028931A1 (en) * | 2009-09-14 | 2012-02-02 | Recordati Ireland Limited | Heterocyclic m-glu5 antagonists |
WO2011073154A1 (en) | 2009-12-17 | 2011-06-23 | Boehringer Ingelheim International Gmbh | New ccr2 receptor antagonists and uses thereof |
PE20130616A1 (es) * | 2010-02-04 | 2013-06-06 | Smidth As F L | Metodo para tratar relaves |
WO2011141477A1 (en) | 2010-05-12 | 2011-11-17 | Boehringer Ingelheim International Gmbh | New ccr2 receptor antagonists, method for producing the same, and use thereof as medicaments |
EP2569298B1 (en) | 2010-05-12 | 2015-11-25 | Boehringer Ingelheim International GmbH | Novel ccr2 receptor antagonists, method for producing the same, and use thereof as medicaments |
WO2011144501A1 (en) | 2010-05-17 | 2011-11-24 | Boehringer Ingelheim International Gmbh | Ccr2 antagonists and uses thereof |
JP5636094B2 (ja) | 2010-05-25 | 2014-12-03 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ccr2受容体アンタゴニスト |
US8962656B2 (en) | 2010-06-01 | 2015-02-24 | Boehringer Ingelheim International Gmbh | CCR2 antagonists |
WO2012037258A1 (en) | 2010-09-16 | 2012-03-22 | Abbott Laboratories | Processes for preparing 1,2-substituted cyclopropyl derivatives |
EP2731941B1 (en) | 2011-07-15 | 2019-05-08 | Boehringer Ingelheim International GmbH | Novel and selective ccr2 antagonists |
WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
EP2647377A1 (en) | 2012-04-06 | 2013-10-09 | Sanofi | Use of an h3 receptor antagonist for the treatment of alzheimer's disease |
EP3317270B1 (en) | 2015-07-02 | 2020-05-13 | Centrexion Therapeutics Corporation | (4-((3r,4r)-3-methoxytetrahydro-pyran-4-ylamino)piperidin-1-yl)(5-methyl-6-(((2r,6s)-6-(p-tolyl)tetrahydro-2h-pyran-2-yl)methylamino)pyrimidin-4yl)methanone citrate |
EP3383853B1 (en) | 2015-12-01 | 2020-11-04 | Merck Sharp & Dohme Corp. | Homobispiperidinyl derivatives as liver x receptor (lxr) beta agonists for treating e.g. alzheimer's disease |
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JPH0418071A (ja) | 1990-05-11 | 1992-01-22 | Sumitomo Pharmaceut Co Ltd | ビスピペリジン誘導体 |
EP1051176B1 (en) | 1998-01-27 | 2006-11-22 | Aventis Pharmaceuticals Inc. | SUBSTITUTED OXOAZAHETEROCYCLYL FACTOR Xa INHIBITORS |
WO2000059510A1 (en) | 1999-04-01 | 2000-10-12 | Pfizer Products Inc. | Aminopyrimidines as sorbitol dehydrogenase inhibitors |
AU773227B2 (en) | 1999-07-28 | 2004-05-20 | Aventis Pharmaceuticals Inc. | Substituted oxoazaheterocyclyl compounds |
PE20020507A1 (es) * | 2000-10-17 | 2002-06-25 | Schering Corp | Compuestos no-imidazoles como antagonistas del receptor histamina h3 |
SK6192003A3 (en) | 2000-11-30 | 2004-07-07 | Pfizer Prod Inc | Combination of GABA agonists and sorbitol dehydrogenase inhibitors |
JP2004529117A (ja) * | 2001-02-08 | 2004-09-24 | シェーリング コーポレイション | 認知欠陥障害の処置における二重のh3/m2アンタゴニストの使用 |
US6660858B2 (en) | 2001-03-28 | 2003-12-09 | Lion Bioscience Ag | 2-aminobenzoxazole derivatives and combinatorial libraries thereof |
US6956040B2 (en) * | 2001-07-16 | 2005-10-18 | Ranbaxy Laboratories Limited | Oxazolidinone piperazinyl derivatives as potential antimicrobials |
WO2003031432A1 (en) | 2001-10-12 | 2003-04-17 | Novo Nordisk A/S | Substituted piperidines and their use for the treatment of diseases related to the histamine h3 receptor |
-
2004
- 2004-09-17 GB GB0420831A patent/GB0420831D0/en not_active Ceased
-
2005
- 2005-09-16 AT AT05789636T patent/ATE433966T1/de not_active IP Right Cessation
- 2005-09-16 JP JP2007531711A patent/JP2008513405A/ja not_active Withdrawn
- 2005-09-16 ES ES05789636T patent/ES2326182T3/es active Active
- 2005-09-16 EP EP05789636A patent/EP1789410B1/en active Active
- 2005-09-16 DE DE602005015002T patent/DE602005015002D1/de active Active
- 2005-09-16 US US11/575,311 patent/US7638631B2/en not_active Expired - Fee Related
- 2005-09-16 WO PCT/EP2005/010169 patent/WO2006029906A1/en active Application Filing
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