JP2006522771A5 - - Google Patents
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- JP2006522771A5 JP2006522771A5 JP2006505136A JP2006505136A JP2006522771A5 JP 2006522771 A5 JP2006522771 A5 JP 2006522771A5 JP 2006505136 A JP2006505136 A JP 2006505136A JP 2006505136 A JP2006505136 A JP 2006505136A JP 2006522771 A5 JP2006522771 A5 JP 2006522771A5
- Authority
- JP
- Japan
- Prior art keywords
- piperidinyl
- phenyl
- oxy
- carbonyl
- alkyl
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims 32
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 13
- 239000011780 sodium chloride Substances 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- -1 -C 3-8 cycloalkyl Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 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
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 2
- 208000006673 Asthma Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 208000008665 Gastrointestinal Disease Diseases 0.000 claims 2
- 206010028735 Nasal congestion Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- ZRJJSZJMZNNDHR-UHFFFAOYSA-N [4-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidine-1-carbonyl]phenyl]-pyrrolidin-1-ylmethanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2CCN(CC2)C(=O)C=2C=CC(=CC=2)C(=O)N2CCCC2)C=C1 ZRJJSZJMZNNDHR-UHFFFAOYSA-N 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000000926 neurological Effects 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 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
- LIWOVSLTFBVUME-UHFFFAOYSA-N (4-fluorophenyl)-[4-[4-(3-piperidin-1-ylpropoxy)phenyl]-3,6-dihydro-2H-pyridin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CC=C(C=2C=CC(OCCCN3CCCCC3)=CC=2)CC1 LIWOVSLTFBVUME-UHFFFAOYSA-N 0.000 claims 1
- UXPLJVPYDYJYMI-UHFFFAOYSA-N (4-fluorophenyl)-[4-[4-(3-piperidin-1-ylpropoxy)phenyl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CCC(C=2C=CC(OCCCN3CCCCC3)=CC=2)CC1 UXPLJVPYDYJYMI-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
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- JXKYYSPYBDQVCT-UHFFFAOYSA-N 1-[4-[4-(1-cyclobutylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]-3-methoxypropan-1-one Chemical compound C1CN(C(=O)CCOC)CCC1C(C=C1)=CC=C1OC1CCN(C2CCC2)CC1 JXKYYSPYBDQVCT-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
- 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
- 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
- 229920000089 Cyclic olefin copolymer Polymers 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
- IFDNPYRTQHZLEX-UHFFFAOYSA-N [4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]piperidin-1-yl]-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C2CCN(CC2)C(=O)C=2C=CC(=CC=2)C(F)(F)F)C=C1 IFDNPYRTQHZLEX-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
- CWPSPEHLTFJAEY-UHFFFAOYSA-N [4-[4-[4-(1-cyclobutylpiperidin-4-yl)oxyphenyl]piperidine-1-carbonyl]phenyl]-pyrrolidin-1-ylmethanone Chemical compound C=1C=C(C(=O)N2CCC(CC2)C=2C=CC(OC3CCN(CC3)C3CCC3)=CC=2)C=CC=1C(=O)N1CCCC1 CWPSPEHLTFJAEY-UHFFFAOYSA-N 0.000 claims 1
- ZWILWPXSSDCFOQ-UHFFFAOYSA-N [4-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxyphenyl]-3,6-dihydro-2H-pyridine-1-carbonyl]phenyl]-pyrrolidin-1-ylmethanone Chemical compound C1CN(C(C)C)CCC1OC1=CC=C(C=2CCN(CC=2)C(=O)C=2C=CC(=CC=2)C(=O)N2CCCC2)C=C1 ZWILWPXSSDCFOQ-UHFFFAOYSA-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
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims 1
- 125000003435 aroyl group Chemical group 0.000 claims 1
- 125000005533 aryl carboxamido 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
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 238000000034 method 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
- NKWNOSFALBCJKE-UHFFFAOYSA-N morpholin-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)N1CCOCC1 NKWNOSFALBCJKE-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 pharmaceutic aid Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 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
- DSMGYFMOOLXJBK-UHFFFAOYSA-N piperidin-1-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)N1CCCCC1 DSMGYFMOOLXJBK-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
- 125000003386 piperidinyl group Chemical group 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
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| GBGB0308333.4A GB0308333D0 (en) | 2003-04-10 | 2003-04-10 | Novel compounds |
| PCT/EP2004/003985 WO2004089373A1 (en) | 2003-04-10 | 2004-04-08 | 4- (4-(heterocyclylalkoxy}phenyl)-1-(heterocyclyl-carbonyl)piperidine derivatives and related compounds as histamine h3 antagonists for the treatment of neurological diseases such as alzheimer’s |
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| JP2006522771A JP2006522771A (ja) | 2006-10-05 |
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| EP1892241B1 (en) | 2005-05-30 | 2016-03-30 | Msd K.K. | Novel piperidine derivative |
| EP1888523B1 (en) * | 2005-06-03 | 2011-10-26 | Abbott Laboratories | Cyclobutyl amine derivatives |
| JP2008543940A (ja) | 2005-06-20 | 2008-12-04 | 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、炭素結合した置換ピペリジンおよびその誘導体 |
| CN101243072A (zh) | 2005-06-20 | 2008-08-13 | 先灵公司 | 用作组胺h3拮抗剂的哌啶衍生物 |
| GB0514812D0 (en) * | 2005-07-19 | 2005-08-24 | Glaxo Group Ltd | Compounds |
| JP4860700B2 (ja) | 2005-09-20 | 2012-01-25 | 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、１−［［１−［（２−アミノ−６−メチル−４−ピリジニル）メチル］−４−フルオロ−４−ピペリジニル］カルボニル］−４−［２−（２−ピリジニル）−３Ｈ−イミダゾ［４，５−ｂ］ピリジン−３−イル］ピペリジン |
| JP2009513590A (ja) * | 2005-10-27 | 2009-04-02 | ユセベ ファルマ ソシエテ アノニム | ラクタム又はラクタム誘導体部分を含む化合物、これらの製造方法、及びこれらの使用 |
| AR058109A1 (es) * | 2005-12-20 | 2008-01-23 | Glaxo Group Ltd | Acido 3 - (4 - {[4 -(4 -{[3 - (3, 3 - dimetil - 1 - piperidinil)propil]oxi}fenil) - 1 - piperidinil]carbonil} - 1 - naftalenil)propanoico como antagonistas de los receptotres de histamina h1/h3, composiciones farmaceuticas que los contienen y su uso en la preparacion de medicamentos para el tratamie |
| US7879880B2 (en) | 2005-12-21 | 2011-02-01 | Schering Corporation | Substituted aniline derivatives useful as histamine H3 antagonists |
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| SI2069312T1 (sl) | 2006-07-25 | 2013-03-29 | Cephalon, Inc. | Derivati piridizinona |
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| JP5489997B2 (ja) | 2007-07-19 | 2014-05-14 | シマベイ セラピューティクス， インコーポレーテッド | 糖尿病および代謝疾患の治療のためのＲＵＰ３またはＧＰＲｌ１９受容体のアゴニストとしてのＮ−アザ環状置換ピロール、ピラゾール、イミダゾール、トリアゾールおよびテトラゾール誘導体 |
| EP2303859A4 (en) * | 2008-06-20 | 2012-08-22 | Metabolex Inc | ARYL GPR119 AGONISTS AND USES THEREOF |
| WO2011041154A1 (en) | 2009-10-01 | 2011-04-07 | Metabolex, 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 |
| SG11201402963TA (en) | 2011-12-08 | 2014-09-26 | Taisho Pharmaceutical Co Ltd | Phenylpyrrole derivative |
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| EA202092627A1 (ru) | 2013-11-18 | 2021-09-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
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| WO2018026890A1 (en) | 2016-08-03 | 2018-02-08 | Cymabay Therapeutics | Oxymethylene aryl compounds for treating inflammatory gastrointestinal diseases or gastrointestinal conditions |
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| US7459461B2 (en) * | 2001-10-19 | 2008-12-02 | Ortho-Mcneil Pharmaceutical, Inc. | Phosphonic acid compounds as inhibitors of serine proteases |
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2003
- 2003-04-10 GB GBGB0308333.4A patent/GB0308333D0/en not_active Ceased
-
2004
- 2004-04-07 AR ARP040101188A patent/AR044006A1/es not_active Application Discontinuation
- 2004-04-08 CA CA002521899A patent/CA2521899A1/en not_active Abandoned
- 2004-04-08 JP JP2006505136A patent/JP2006522771A/ja active Pending
- 2004-04-08 AT AT04726514T patent/ATE365039T1/de not_active IP Right Cessation
- 2004-04-08 TW TW093109666A patent/TW200503710A/zh unknown
- 2004-04-08 US US10/551,985 patent/US20060205774A1/en not_active Abandoned
- 2004-04-08 RU RU2005134006/04A patent/RU2005134006A/ru not_active Application Discontinuation
- 2004-04-08 KR KR1020057019137A patent/KR20050111638A/ko not_active Application Discontinuation
- 2004-04-08 DE DE602004007119T patent/DE602004007119T2/de not_active Expired - Fee Related
- 2004-04-08 BR BRPI0409110-8A patent/BRPI0409110A/pt not_active Application Discontinuation
- 2004-04-08 CN CNA2004800161953A patent/CN1805747A/zh active Pending
- 2004-04-08 ES ES04726514T patent/ES2288681T3/es not_active Expired - Lifetime
- 2004-04-08 WO PCT/EP2004/003985 patent/WO2004089373A1/en active IP Right Grant
- 2004-04-08 EP EP04726514A patent/EP1610786B9/en not_active Expired - Lifetime
- 2004-04-08 AU AU2004228949A patent/AU2004228949B2/en not_active Ceased
- 2004-04-08 MX MXPA05010816A patent/MXPA05010816A/es not_active Application Discontinuation
-
2005
- 2005-09-27 ZA ZA200507795A patent/ZA200507795B/en unknown
- 2005-10-06 CO CO05101708A patent/CO5640135A2/es not_active Application Discontinuation
- 2005-10-11 MA MA28548A patent/MA27726A1/fr unknown
- 2005-11-08 IS IS8118A patent/IS8118A/is unknown
- 2005-11-09 NO NO20055256A patent/NO20055256L/no not_active Application Discontinuation
