RU2005134006A - Производные 4-(4-{гетероциклилалкокси}фенил0-1-(гетероциклилкарбонил)пиперидина и родственные соединения как антагонисты гистамина н3 для лечения неврологических заболеваний, таких как болезнь альцгеймера - Google Patents
Производные 4-(4-{гетероциклилалкокси}фенил0-1-(гетероциклилкарбонил)пиперидина и родственные соединения как антагонисты гистамина н3 для лечения неврологических заболеваний, таких как болезнь альцгеймера Download PDFInfo
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- RU2005134006A RU2005134006A RU2005134006/04A RU2005134006A RU2005134006A RU 2005134006 A RU2005134006 A RU 2005134006A RU 2005134006/04 A RU2005134006/04 A RU 2005134006/04A RU 2005134006 A RU2005134006 A RU 2005134006A RU 2005134006 A RU2005134006 A RU 2005134006A
- Authority
- RU
- Russia
- Prior art keywords
- piperidinyl
- phenyl
- oxy
- carbonyl
- alkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims 33
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title claims 6
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 title 2
- 239000005557 antagonist Substances 0.000 title 1
- 229960001340 histamine Drugs 0.000 title 1
- 230000000926 neurological effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 22
- -1 —C 3-8 cycloalkyl Chemical group 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 239000012453 solvate Substances 0.000 claims 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 208000012902 Nervous system disease Diseases 0.000 claims 4
- 208000025966 Neurological disease Diseases 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- FNKJMZFGNDROBX-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]methanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2CCN(CC2)C(=O)N2CCS(=O)(=O)CC2)C=C1 FNKJMZFGNDROBX-UHFFFAOYSA-N 0.000 claims 1
- AUDFWNJSBWERPS-UHFFFAOYSA-N (4-fluorophenyl)-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]-3,6-dihydro-2h-pyridin-1-yl]methanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C=2CCN(CC=2)C(=O)C=2C=CC(F)=CC=2)C=C1 AUDFWNJSBWERPS-UHFFFAOYSA-N 0.000 claims 1
- UIAASDABLBWOOP-UHFFFAOYSA-N (4-fluorophenyl)-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]methanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2CCN(CC2)C(=O)C=2C=CC(F)=CC=2)C=C1 UIAASDABLBWOOP-UHFFFAOYSA-N 0.000 claims 1
- VUTGSSBHUVXFGE-UHFFFAOYSA-N (4-methylsulfonylphenyl)-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]-3,6-dihydro-2h-pyridin-1-yl]methanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C=2CCN(CC=2)C(=O)C=2C=CC(=CC=2)S(C)(=O)=O)C=C1 VUTGSSBHUVXFGE-UHFFFAOYSA-N 0.000 claims 1
- IXLCMZDYRNWZJJ-UHFFFAOYSA-N (4-methylsulfonylphenyl)-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]methanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2CCN(CC2)C(=O)C=2C=CC(=CC=2)S(C)(=O)=O)C=C1 IXLCMZDYRNWZJJ-UHFFFAOYSA-N 0.000 claims 1
- DAWFUXXLTUKFNM-UHFFFAOYSA-N (4-methylsulfonylphenyl)-[4-[4-(3-piperidin-1-ylpropoxy)phenyl]-3,6-dihydro-2h-pyridin-1-yl]methanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)N1CC=C(C=2C=CC(OCCCN3CCCCC3)=CC=2)CC1 DAWFUXXLTUKFNM-UHFFFAOYSA-N 0.000 claims 1
- MIRFXYJHBCWHRK-UHFFFAOYSA-N (4-methylsulfonylphenyl)-[4-[4-(3-piperidin-1-ylpropoxy)phenyl]piperidin-1-yl]methanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)N1CCC(C=2C=CC(OCCCN3CCCCC3)=CC=2)CC1 MIRFXYJHBCWHRK-UHFFFAOYSA-N 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 claims 1
- KDWFTVZDUYFGNH-UHFFFAOYSA-N 3-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidine-1-carbonyl]benzonitrile Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2CCN(CC2)C(=O)C=2C=C(C=CC=2)C#N)C=C1 KDWFTVZDUYFGNH-UHFFFAOYSA-N 0.000 claims 1
- GXAUNNBJCYVYAQ-UHFFFAOYSA-N 3-methoxy-1-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]propan-1-one Chemical compound C1CN(C(=O)CCOC)CCC1C(C=C1)=CC=C1OC1CCN(C(C)C)CC1 GXAUNNBJCYVYAQ-UHFFFAOYSA-N 0.000 claims 1
- ZGENLYHCWNSHSX-UHFFFAOYSA-N 4-[4-[4-(1-cyclobutylpiperidin-4-yl)oxyphenyl]piperidine-1-carbonyl]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C(=O)N(CC1)CCC1C(C=C1)=CC=C1OC(CC1)CCN1C1CCC1 ZGENLYHCWNSHSX-UHFFFAOYSA-N 0.000 claims 1
- QQIPUEDLOOHTIF-UHFFFAOYSA-N 4-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]-3,6-dihydro-2h-pyridine-1-carbonyl]benzonitrile Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C=2CCN(CC=2)C(=O)C=2C=CC(=CC=2)C#N)C=C1 QQIPUEDLOOHTIF-UHFFFAOYSA-N 0.000 claims 1
- IIRGREQPBZQHNX-UHFFFAOYSA-N 4-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidine-1-carbonyl]benzonitrile Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2CCN(CC2)C(=O)C=2C=CC(=CC=2)C#N)C=C1 IIRGREQPBZQHNX-UHFFFAOYSA-N 0.000 claims 1
- PZPZCDJFSSUXJD-UHFFFAOYSA-N 4-[4-[4-(3-piperidin-1-ylpropoxy)phenyl]-3,6-dihydro-2h-pyridine-1-carbonyl]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C(=O)N(CC=1)CCC=1C(C=C1)=CC=C1OCCCN1CCCCC1 PZPZCDJFSSUXJD-UHFFFAOYSA-N 0.000 claims 1
- QBVJCITWQOLHNP-UHFFFAOYSA-N 4-[4-[4-(3-piperidin-1-ylpropoxy)phenyl]piperidine-1-carbonyl]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C(=O)N(CC1)CCC1C(C=C1)=CC=C1OCCCN1CCCCC1 QBVJCITWQOLHNP-UHFFFAOYSA-N 0.000 claims 1
- CGUJRUJRICXRMN-OAQYLSRUSA-N 4-[4-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]piperidine-1-carbonyl]benzonitrile Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C2CCN(CC2)C(=O)C=2C=CC(=CC=2)C#N)C=C1 CGUJRUJRICXRMN-OAQYLSRUSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- VYJQBIJLOSXVDC-UHFFFAOYSA-N 5-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidine-1-carbonyl]pyridine-2-carbonitrile Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2CCN(CC2)C(=O)C=2C=NC(=CC=2)C#N)C=C1 VYJQBIJLOSXVDC-UHFFFAOYSA-N 0.000 claims 1
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 1
- BYVIWVGGYBENQU-UHFFFAOYSA-N [4-[4-(1-cyclobutylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CCC(C=2C=CC(OC3CCN(CC3)C3CCC3)=CC=2)CC1 BYVIWVGGYBENQU-UHFFFAOYSA-N 0.000 claims 1
- PHUIPDGHPHAULA-UHFFFAOYSA-N [4-[4-(1-cyclobutylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]-morpholin-4-ylmethanone Chemical compound C1CC(C=2C=CC(OC3CCN(CC3)C3CCC3)=CC=2)CCN1C(=O)N1CCOCC1 PHUIPDGHPHAULA-UHFFFAOYSA-N 0.000 claims 1
- HNTYNRAHLDSJER-UHFFFAOYSA-N [4-[4-(1-cyclobutylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]-pyridin-3-ylmethanone Chemical compound C=1C=CN=CC=1C(=O)N(CC1)CCC1C(C=C1)=CC=C1OC(CC1)CCN1C1CCC1 HNTYNRAHLDSJER-UHFFFAOYSA-N 0.000 claims 1
- NZSSDBFPZIYGMW-UHFFFAOYSA-N [4-[4-(1-cyclobutylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]-pyridin-4-ylmethanone Chemical compound C=1C=NC=CC=1C(=O)N(CC1)CCC1C(C=C1)=CC=C1OC(CC1)CCN1C1CCC1 NZSSDBFPZIYGMW-UHFFFAOYSA-N 0.000 claims 1
- PJGRPGGUINPPES-UHFFFAOYSA-N [4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]-3,6-dihydro-2h-pyridin-1-yl]-pyridin-4-ylmethanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C=2CCN(CC=2)C(=O)C=2C=CN=CC=2)C=C1 PJGRPGGUINPPES-UHFFFAOYSA-N 0.000 claims 1
- CJIUPNFSGPIVAB-UHFFFAOYSA-N [4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]-3,6-dihydro-2h-pyridin-1-yl]-pyrrolidin-1-ylmethanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C=2CCN(CC=2)C(=O)N2CCCC2)C=C1 CJIUPNFSGPIVAB-UHFFFAOYSA-N 0.000 claims 1
- VRSKXLFHDYYTGZ-UHFFFAOYSA-N [4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]-[6-(trifluoromethyl)pyridin-3-yl]methanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2CCN(CC2)C(=O)C=2C=NC(=CC=2)C(F)(F)F)C=C1 VRSKXLFHDYYTGZ-UHFFFAOYSA-N 0.000 claims 1
- OHOTYEITSGRAEG-UHFFFAOYSA-N [4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]-pyrazin-2-ylmethanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2CCN(CC2)C(=O)C=2N=CC=NC=2)C=C1 OHOTYEITSGRAEG-UHFFFAOYSA-N 0.000 claims 1
- JQNYMSZAHQLOBG-UHFFFAOYSA-N [4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]-pyridin-3-ylmethanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2CCN(CC2)C(=O)C=2C=NC=CC=2)C=C1 JQNYMSZAHQLOBG-UHFFFAOYSA-N 0.000 claims 1
- QWZSJRPQFYVKAA-UHFFFAOYSA-N [4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]-pyridin-4-ylmethanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2CCN(CC2)C(=O)C=2C=CN=CC=2)C=C1 QWZSJRPQFYVKAA-UHFFFAOYSA-N 0.000 claims 1
- XCGSTTVMKWSASI-UHFFFAOYSA-N [4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]-pyrrolidin-1-ylmethanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2CCN(CC2)C(=O)N2CCCC2)C=C1 XCGSTTVMKWSASI-UHFFFAOYSA-N 0.000 claims 1
- OGVGKSBUSDPULA-UHFFFAOYSA-N [4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]-quinoxalin-6-ylmethanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2CCN(CC2)C(=O)C=2C=C3N=CC=NC3=CC=2)C=C1 OGVGKSBUSDPULA-UHFFFAOYSA-N 0.000 claims 1
- AROXYYQQWMFMSW-UHFFFAOYSA-N [4-[4-(3-piperidin-1-ylpropoxy)phenyl]-3,6-dihydro-2h-pyridin-1-yl]-pyrrolidin-1-ylmethanone Chemical compound C1CC(C=2C=CC(OCCCN3CCCCC3)=CC=2)=CCN1C(=O)N1CCCC1 AROXYYQQWMFMSW-UHFFFAOYSA-N 0.000 claims 1
- QSDQCHSCBVCNBP-UHFFFAOYSA-N [4-[4-(3-piperidin-1-ylpropoxy)phenyl]piperidin-1-yl]-pyridin-3-ylmethanone Chemical compound C=1C=CN=CC=1C(=O)N(CC1)CCC1C(C=C1)=CC=C1OCCCN1CCCCC1 QSDQCHSCBVCNBP-UHFFFAOYSA-N 0.000 claims 1
- JMDIVDFGKGTHGQ-UHFFFAOYSA-N [4-[4-(3-piperidin-1-ylpropoxy)phenyl]piperidin-1-yl]-pyridin-4-ylmethanone Chemical compound C=1C=NC=CC=1C(=O)N(CC1)CCC1C(C=C1)=CC=C1OCCCN1CCCCC1 JMDIVDFGKGTHGQ-UHFFFAOYSA-N 0.000 claims 1
- SSKSEDDHYACMNJ-UHFFFAOYSA-N [4-[4-(3-piperidin-1-ylpropoxy)phenyl]piperidin-1-yl]-pyrrolidin-1-ylmethanone Chemical compound C1CC(C=2C=CC(OCCCN3CCCCC3)=CC=2)CCN1C(=O)N1CCCC1 SSKSEDDHYACMNJ-UHFFFAOYSA-N 0.000 claims 1
- QCMYZPJXNPRGNJ-HXUWFJFHSA-N [4-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]piperidin-1-yl]-(oxan-4-yl)methanone Chemical compound C[C@@H]1CCCN1CCCOC1=CC=C(C2CCN(CC2)C(=O)C2CCOCC2)C=C1 QCMYZPJXNPRGNJ-HXUWFJFHSA-N 0.000 claims 1
- QXABCVDPUUYRBS-NHCUHLMSSA-N [4-[4-[3-[(2r,5r)-2,5-dimethylpyrrolidin-1-yl]propoxy]phenyl]piperidin-1-yl]-(oxan-4-yl)methanone Chemical compound C[C@@H]1CC[C@@H](C)N1CCCOC1=CC=C(C2CCN(CC2)C(=O)C2CCOCC2)C=C1 QXABCVDPUUYRBS-NHCUHLMSSA-N 0.000 claims 1
- VAMVQHXXQYWMMN-UHFFFAOYSA-N [4-[4-[4-(3-piperidin-1-ylpropoxy)phenyl]-3,6-dihydro-2h-pyridine-1-carbonyl]phenyl]-pyrrolidin-1-ylmethanone Chemical compound C=1C=C(C(=O)N2CC=C(CC2)C=2C=CC(OCCCN3CCCCC3)=CC=2)C=CC=1C(=O)N1CCCC1 VAMVQHXXQYWMMN-UHFFFAOYSA-N 0.000 claims 1
- JUMVTKVGFUCAMF-UHFFFAOYSA-N [4-[4-[4-(3-piperidin-1-ylpropoxy)phenyl]piperidine-1-carbonyl]phenyl]-pyrrolidin-1-ylmethanone Chemical compound C=1C=C(C(=O)N2CCC(CC2)C=2C=CC(OCCCN3CCCCC3)=CC=2)C=CC=1C(=O)N1CCCC1 JUMVTKVGFUCAMF-UHFFFAOYSA-N 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
- 125000003435 aroyl group Chemical group 0.000 claims 1
- 125000005421 aryl sulfonamido group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- ZYKSCJHCDIQJFQ-UHFFFAOYSA-N azetidin-1-yl-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]methanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2CCN(CC2)C(=O)N2CCC2)C=C1 ZYKSCJHCDIQJFQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- XJCYJEZNAFTFMY-UHFFFAOYSA-N morpholin-4-yl-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]-3,6-dihydro-2h-pyridin-1-yl]methanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C=2CCN(CC=2)C(=O)N2CCOCC2)C=C1 XJCYJEZNAFTFMY-UHFFFAOYSA-N 0.000 claims 1
- KQDWNYQIEPUHQE-UHFFFAOYSA-N morpholin-4-yl-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]methanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2CCN(CC2)C(=O)N2CCOCC2)C=C1 KQDWNYQIEPUHQE-UHFFFAOYSA-N 0.000 claims 1
- MZIWFGPWTARXQO-UHFFFAOYSA-N morpholin-4-yl-[4-[4-(3-piperidin-1-ylpropoxy)phenyl]piperidin-1-yl]methanone Chemical compound C1CC(C=2C=CC(OCCCN3CCCCC3)=CC=2)CCN1C(=O)N1CCOCC1 MZIWFGPWTARXQO-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- ONOGPSWWZWHIIC-UHFFFAOYSA-N oxan-4-yl-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]-3,6-dihydro-2h-pyridin-1-yl]methanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C=2CCN(CC=2)C(=O)C2CCOCC2)C=C1 ONOGPSWWZWHIIC-UHFFFAOYSA-N 0.000 claims 1
- ZQLGOBAADXFBEF-UHFFFAOYSA-N oxan-4-yl-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]methanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2CCN(CC2)C(=O)C2CCOCC2)C=C1 ZQLGOBAADXFBEF-UHFFFAOYSA-N 0.000 claims 1
- SCYSKTGSUJXSFY-UHFFFAOYSA-N oxan-4-yl-[4-[4-(3-piperidin-1-ylpropoxy)phenyl]-3,6-dihydro-2h-pyridin-1-yl]methanone Chemical compound C1CC(C=2C=CC(OCCCN3CCCCC3)=CC=2)=CCN1C(=O)C1CCOCC1 SCYSKTGSUJXSFY-UHFFFAOYSA-N 0.000 claims 1
- XFSIGVKIEJJUNI-UHFFFAOYSA-N oxan-4-yl-[4-[4-(3-piperidin-1-ylpropoxy)phenyl]piperidin-1-yl]methanone Chemical compound C1CC(C=2C=CC(OCCCN3CCCCC3)=CC=2)CCN1C(=O)C1CCOCC1 XFSIGVKIEJJUNI-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- HMMHLXIWAVNSET-UHFFFAOYSA-N piperidin-1-yl-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]-3,6-dihydro-2h-pyridin-1-yl]methanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C=2CCN(CC=2)C(=O)N2CCCCC2)C=C1 HMMHLXIWAVNSET-UHFFFAOYSA-N 0.000 claims 1
- HWZAWCTWTVRSTN-UHFFFAOYSA-N piperidin-1-yl-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]methanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2CCN(CC2)C(=O)N2CCCCC2)C=C1 HWZAWCTWTVRSTN-UHFFFAOYSA-N 0.000 claims 1
- OFDYKFZVAHONPB-UHFFFAOYSA-N piperidin-1-yl-[4-[4-(3-piperidin-1-ylpropoxy)phenyl]piperidin-1-yl]methanone Chemical compound C1CC(C=2C=CC(OCCCN3CCCCC3)=CC=2)CCN1C(=O)N1CCCCC1 OFDYKFZVAHONPB-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A61P25/10—Antiepileptics; Anticonvulsants for petit-mal
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Hospice & Palliative Care (AREA)
- Obesity (AREA)
- Psychology (AREA)
- Hematology (AREA)
- Child & Adolescent Psychology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0308333.4 | 2003-04-10 | ||
| GBGB0308333.4A GB0308333D0 (en) | 2003-04-10 | 2003-04-10 | Novel compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2005134006A true RU2005134006A (ru) | 2006-04-10 |
Family
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Family Applications (1)
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| RU2005134006/04A RU2005134006A (ru) | 2003-04-10 | 2004-04-08 | Производные 4-(4-{гетероциклилалкокси}фенил0-1-(гетероциклилкарбонил)пиперидина и родственные соединения как антагонисты гистамина н3 для лечения неврологических заболеваний, таких как болезнь альцгеймера |
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| EP (1) | EP1610786B9 (enExample) |
| JP (1) | JP2006522771A (enExample) |
| KR (1) | KR20050111638A (enExample) |
| CN (1) | CN1805747A (enExample) |
| AR (1) | AR044006A1 (enExample) |
| AT (1) | ATE365039T1 (enExample) |
| AU (1) | AU2004228949B2 (enExample) |
| BR (1) | BRPI0409110A (enExample) |
| CA (1) | CA2521899A1 (enExample) |
| CO (1) | CO5640135A2 (enExample) |
| DE (1) | DE602004007119T2 (enExample) |
| ES (1) | ES2288681T3 (enExample) |
| GB (1) | GB0308333D0 (enExample) |
| IS (1) | IS8118A (enExample) |
| MA (1) | MA27726A1 (enExample) |
| MX (1) | MXPA05010816A (enExample) |
| NO (1) | NO20055256L (enExample) |
| RU (1) | RU2005134006A (enExample) |
| TW (1) | TW200503710A (enExample) |
| WO (1) | WO2004089373A1 (enExample) |
| ZA (1) | ZA200507795B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2430099C2 (ru) * | 2007-01-22 | 2011-09-27 | Пфайзер Продактс Инк. | Тозилатная соль терапевтического соединения и ее фармацевтические композиции |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US20050256118A1 (en) * | 2004-05-12 | 2005-11-17 | Altenbach Robert J | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
| EP1717235A3 (en) * | 2005-04-29 | 2007-02-28 | Bioprojet | Phenoxypropylpiperidines and -pyrrolidines and their use as histamine H3-receptor ligands |
| EP1892241B1 (en) | 2005-05-30 | 2016-03-30 | Msd K.K. | Novel piperidine derivative |
| ATE530519T1 (de) * | 2005-06-03 | 2011-11-15 | Abbott Lab | Cyclobutylaminderivate |
| EP1902046B1 (en) | 2005-06-20 | 2009-12-02 | Schering Corporation | Piperidine derivatives useful as histamine h3 antagonists |
| US7408066B2 (en) | 2005-06-20 | 2008-08-05 | Schering Corproation | Carbon-linked substituted piperidines and derivatives thereof useful as histamine H3 antagonists |
| GB0514812D0 (en) * | 2005-07-19 | 2005-08-24 | Glaxo Group Ltd | Compounds |
| CA2623025A1 (en) | 2005-09-20 | 2007-03-29 | Schering Corporation | 1- [ [1- [ (2-amin0-6-methyl-4-pyridinyl) methyl] -4-flu0r0-4-piperidinyl,] carbonyl] -4- [2- (2-pyridinyl) -3h-imidaz0 [4 , 5-b] pyridin-3-yl] piperidine useful as histamine h3 antagonist |
| WO2007048595A1 (en) * | 2005-10-27 | 2007-05-03 | Ucb Pharma, S.A. | Compounds comprising a lactam or a lactam derivative moiety, processes for making them, and their uses |
| TW200730498A (en) * | 2005-12-20 | 2007-08-16 | Glaxo Group Ltd | Compounds |
| JP2009521448A (ja) | 2005-12-21 | 2009-06-04 | シェーリング コーポレイション | ヒスタミンｈ３アンタゴニストとして有用なフェノキシピペリジンおよびそのアナログ |
| WO2007075688A2 (en) | 2005-12-21 | 2007-07-05 | Schering Corporation | Substituted aniline derivatives useful as histamine h3 antagonists |
| NZ574873A (en) | 2006-07-25 | 2012-03-30 | Cephalon Inc | Pyridazinone derivatives as h3 inhibitors |
| TW200823204A (en) * | 2006-10-17 | 2008-06-01 | Arena Pharm Inc | Biphenyl sulfonyl and phenyl-heteroaryl sulfonyl modulators of the histamine H3-receptor useful for the treatment of disorders related thereto |
| US7638541B2 (en) | 2006-12-28 | 2009-12-29 | Metabolex Inc. | 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine |
| CA2693169C (en) | 2007-07-19 | 2016-01-12 | Metabolex, Inc. | N-linked heterocyclic receptor agonists for the treatment of diabetes and metabolic disorders |
| BRPI0914891A2 (pt) * | 2008-06-20 | 2015-11-24 | Metabolex Inc | agonistas de aril gpr119 e usos dos mesmos |
| EP2483281B1 (en) | 2009-10-01 | 2014-06-04 | Cymabay Therapeutics, Inc. | Substituted tetrazol-1-yl-phenoxymethyl-thiazol-2-yl-piperidinyl-pyrimidine salts |
| CA2802541A1 (en) | 2010-06-23 | 2011-12-29 | Metabolex, Inc. | Compositions of 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine |
| TWI555741B (zh) | 2011-12-08 | 2016-11-01 | 大正製藥股份有限公司 | Phenylpyrrole derivatives |
| WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
| HUP1300139A2 (en) * | 2013-03-06 | 2014-09-29 | Richter Gedeon Nyrt | Phenoxypiperidine h3 antagonists |
| PE20161035A1 (es) | 2013-03-15 | 2016-11-13 | Global Blood Therapeutics Inc | Compuestos y usos de estos para la modulacion de la hemoglobina |
| EA201992707A1 (ru) | 2013-11-18 | 2020-06-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
| AU2016250976B2 (en) | 2015-04-21 | 2020-02-27 | Jiangsu Hengrui Medicine Co., Ltd. | Imidazo isoindole derivative, preparation method therefor and medical use thereof |
| WO2018026890A1 (en) | 2016-08-03 | 2018-02-08 | Cymabay Therapeutics | Oxymethylene aryl compounds for treating inflammatory gastrointestinal diseases or gastrointestinal conditions |
| MX2021009685A (es) * | 2019-03-05 | 2021-09-10 | Eisai R&D Man Co Ltd | Compuesto heterociclo pentaciclico. |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4166853A (en) * | 1978-05-05 | 1979-09-04 | The Upjohn Company | Antihypertensive 7-trifluoromethyl-4-aminoquinolones |
| ATE365209T1 (de) * | 1992-05-14 | 2007-07-15 | Baylor College Medicine | Mutierte steroidhormonrezeptoren, methoden für ihre benutzung und molekularer schalter für gentherapie |
| US5364791A (en) * | 1992-05-14 | 1994-11-15 | Elisabetta Vegeto | Progesterone receptor having C. terminal hormone binding domain truncations |
| DE4407139A1 (de) * | 1994-03-04 | 1995-09-07 | Thomae Gmbh Dr K | Aryl-1-azacycloalkane und deren Salze, diese Verbindungen enthaltende Arzneimittel und deren Verwendung sowie Verfahren zu ihrer Herstellung |
| CA2214288C (en) * | 1996-09-18 | 2006-07-18 | Lonza Ag | Process for the preparation of 1-acyl-4-arylpiperidines |
| EP0837065A1 (de) * | 1996-10-16 | 1998-04-22 | Ciba SC Holding AG | Phenylglycidylether-HALS |
| US6515013B2 (en) * | 2000-07-13 | 2003-02-04 | Abbott Laboratories | 1,3-disubstituted and 1,3,3-trisubstituted pyrrolidines as histamine-3 receptor ligands and their therapeutic applications |
| WO2002006223A1 (en) * | 2000-07-13 | 2002-01-24 | Abbott Laboratories | 1,3-disubstituted and 1,3,3-trisubstituted pyrrolidines as histamine-3 receptor ligands and their therapeutic applications |
| HK1053110A1 (zh) * | 2000-08-08 | 2003-10-10 | Ortho-Mcneil Pharmaceutical, Inc. | 作為h3受體配體的非咪唑芳氧基烷基胺 |
| JP4104983B2 (ja) * | 2001-02-28 | 2008-06-18 | メルク エンド カムパニー インコーポレーテッド | メラノコルチン−４受容体作動薬としてのアシル化ピペリジン誘導体 |
| AU2002306848A1 (en) * | 2001-03-23 | 2002-10-08 | Elan Pharmaceuticals, Inc. | Methods of treating alzheimer's disease with piperidin derivates |
| US7459461B2 (en) * | 2001-10-19 | 2008-12-02 | Ortho-Mcneil Pharmaceutical, Inc. | Phosphonic acid compounds as inhibitors of serine proteases |
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2004
- 2004-04-07 AR ARP040101188A patent/AR044006A1/es not_active Application Discontinuation
- 2004-04-08 MX MXPA05010816A patent/MXPA05010816A/es not_active Application Discontinuation
- 2004-04-08 US US10/551,985 patent/US20060205774A1/en not_active Abandoned
- 2004-04-08 TW TW093109666A patent/TW200503710A/zh unknown
- 2004-04-08 RU RU2005134006/04A patent/RU2005134006A/ru not_active Application Discontinuation
- 2004-04-08 EP EP04726514A patent/EP1610786B9/en not_active Expired - Lifetime
- 2004-04-08 DE DE602004007119T patent/DE602004007119T2/de not_active Expired - Fee Related
- 2004-04-08 ES ES04726514T patent/ES2288681T3/es not_active Expired - Lifetime
- 2004-04-08 JP JP2006505136A patent/JP2006522771A/ja active Pending
- 2004-04-08 WO PCT/EP2004/003985 patent/WO2004089373A1/en not_active Ceased
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- 2004-04-08 KR KR1020057019137A patent/KR20050111638A/ko not_active Withdrawn
- 2004-04-08 BR BRPI0409110-8A patent/BRPI0409110A/pt not_active Application Discontinuation
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- 2004-04-08 AT AT04726514T patent/ATE365039T1/de not_active IP Right Cessation
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- 2005-11-08 IS IS8118A patent/IS8118A/is unknown
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2430099C2 (ru) * | 2007-01-22 | 2011-09-27 | Пфайзер Продактс Инк. | Тозилатная соль терапевтического соединения и ее фармацевтические композиции |
Also Published As
| Publication number | Publication date |
|---|---|
| DE602004007119D1 (de) | 2007-08-02 |
| EP1610786B1 (en) | 2007-06-20 |
| JP2006522771A (ja) | 2006-10-05 |
| EP1610786A1 (en) | 2006-01-04 |
| AU2004228949B2 (en) | 2006-11-02 |
| ES2288681T3 (es) | 2008-01-16 |
| GB0308333D0 (en) | 2003-05-14 |
| BRPI0409110A (pt) | 2006-03-28 |
| MA27726A1 (fr) | 2006-01-02 |
| US20060205774A1 (en) | 2006-09-14 |
| ATE365039T1 (de) | 2007-07-15 |
| NO20055256L (no) | 2006-01-10 |
| AU2004228949A1 (en) | 2004-10-21 |
| CA2521899A1 (en) | 2004-10-21 |
| WO2004089373A1 (en) | 2004-10-21 |
| NO20055256D0 (no) | 2005-11-09 |
| ZA200507795B (en) | 2006-07-26 |
| CO5640135A2 (es) | 2006-05-31 |
| IS8118A (is) | 2005-11-08 |
| MXPA05010816A (es) | 2005-12-05 |
| KR20050111638A (ko) | 2005-11-25 |
| AR044006A1 (es) | 2005-08-24 |
| DE602004007119T2 (de) | 2008-02-21 |
| EP1610786B9 (en) | 2008-02-27 |
| TW200503710A (en) | 2005-02-01 |
| CN1805747A (zh) | 2006-07-19 |
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