JP2007519717A5 - - Google Patents
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- Publication number
- JP2007519717A5 JP2007519717A5 JP2006551005A JP2006551005A JP2007519717A5 JP 2007519717 A5 JP2007519717 A5 JP 2007519717A5 JP 2006551005 A JP2006551005 A JP 2006551005A JP 2006551005 A JP2006551005 A JP 2006551005A JP 2007519717 A5 JP2007519717 A5 JP 2007519717A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxypropyl
- piperidin
- oxo
- carboxamide
- dichlorophenoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 2-oxo-thiazol-5-yl Chemical group 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000001424 substituent group Chemical group 0.000 claims 11
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims 4
- CAVTXAUZYYVGML-UHFFFAOYSA-N 1,2-dihydropyridine-5-carboxamide Chemical compound NC(=O)C1=CNCC=C1 CAVTXAUZYYVGML-UHFFFAOYSA-N 0.000 claims 4
- 230000002378 acidificating effect Effects 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- IIVZUXDJHNPHGX-UHFFFAOYSA-N 2,3-dihydro-1,3-thiazole-5-carboxamide Chemical compound NC(=O)C1=CNCS1 IIVZUXDJHNPHGX-UHFFFAOYSA-N 0.000 claims 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 150000003857 carboxamides Chemical class 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- LFAUJCUNVDPEGM-MRXNPFEDSA-N 2-[2-chloro-5-[[(2r)-3-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]-2-hydroxypropyl]carbamoyl]phenoxy]acetic acid Chemical compound CC1=C(Cl)C(Cl)=CC=C1OC1CCN(C[C@H](O)CNC(=O)C=2C=C(OCC(O)=O)C(Cl)=CC=2)CC1 LFAUJCUNVDPEGM-MRXNPFEDSA-N 0.000 claims 1
- LIAOZQMRLRRNTQ-QGZVFWFLSA-N 2-[3-[[(2r)-3-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]-2-hydroxypropyl]carbamoyl]phenoxy]acetic acid Chemical compound CC1=C(Cl)C(Cl)=CC=C1OC1CCN(C[C@H](O)CNC(=O)C=2C=C(OCC(O)=O)C=CC=2)CC1 LIAOZQMRLRRNTQ-QGZVFWFLSA-N 0.000 claims 1
- SIBBBIYMTFGUKJ-CYBMUJFWSA-N 2-[5-[[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]carbamoyl]-2-oxo-4-(trifluoromethyl)pyridin-1-yl]acetic acid Chemical compound C([C@@H](O)CN1CCC(CC1)OC=1C=C(Cl)C(Cl)=CC=1)NC(=O)C1=CN(CC(O)=O)C(=O)C=C1C(F)(F)F SIBBBIYMTFGUKJ-CYBMUJFWSA-N 0.000 claims 1
- PLYDEGUVOVLIIB-OAHLLOKOSA-N 2-chloro-5-[[(2r)-3-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]-2-hydroxypropyl]carbamoyl]benzoic acid Chemical compound CC1=C(Cl)C(Cl)=CC=C1OC1CCN(C[C@H](O)CNC(=O)C=2C=C(C(Cl)=CC=2)C(O)=O)CC1 PLYDEGUVOVLIIB-OAHLLOKOSA-N 0.000 claims 1
- SMYNYMYZAFKUCT-QGZVFWFLSA-N 3-[2-[[(2r)-3-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]-2-hydroxypropyl]amino]-2-oxoethoxy]benzoic acid Chemical compound CC1=C(Cl)C(Cl)=CC=C1OC1CCN(C[C@H](O)CNC(=O)COC=2C=C(C=CC=2)C(O)=O)CC1 SMYNYMYZAFKUCT-QGZVFWFLSA-N 0.000 claims 1
- WZMVUXCCPGCXTJ-MRXNPFEDSA-N 4-chloro-3-[2-[[(2r)-3-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]-2-hydroxypropyl]amino]-2-oxoethoxy]benzoic acid Chemical compound CC1=C(Cl)C(Cl)=CC=C1OC1CCN(C[C@H](O)CNC(=O)COC=2C(=CC=C(C=2)C(O)=O)Cl)CC1 WZMVUXCCPGCXTJ-MRXNPFEDSA-N 0.000 claims 1
- HUZXNYMWLWWBPF-OAHLLOKOSA-N 4-chloro-3-[[(2r)-3-[4-(3,4-dichloro-2-methylphenoxy)piperidin-1-yl]-2-hydroxypropyl]carbamoyl]benzoic acid Chemical compound CC1=C(Cl)C(Cl)=CC=C1OC1CCN(C[C@H](O)CNC(=O)C=2C(=CC=C(C=2)C(O)=O)Cl)CC1 HUZXNYMWLWWBPF-OAHLLOKOSA-N 0.000 claims 1
- GNCDRIYQZSBCRD-QGZVFWFLSA-N 5-cyano-2-cyclopropyl-n-[(2r)-3-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]-2-hydroxypropyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound CC1=C(Cl)C=CC(OC2CCN(C[C@H](O)CNC(=O)C3=C(NC(=O)C(C#N)=C3)C3CC3)CC2)=C1Cl GNCDRIYQZSBCRD-QGZVFWFLSA-N 0.000 claims 1
- JGOVHUYOAUHAHP-MRXNPFEDSA-N 5-cyano-2-cyclopropyl-n-[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound C([C@@H](O)CN1CCC(CC1)OC=1C=C(Cl)C(Cl)=CC=1)NC(=O)C=1C=C(C#N)C(=O)NC=1C1CC1 JGOVHUYOAUHAHP-MRXNPFEDSA-N 0.000 claims 1
- KYKUZLYNQFQIOE-CQSZACIVSA-N 5-cyano-n-[(2r)-3-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]-2-hydroxypropyl]-6-oxo-2-(trifluoromethyl)-1h-pyridine-3-carboxamide Chemical compound CC1=C(Cl)C=CC(OC2CCN(C[C@H](O)CNC(=O)C3=C(NC(=O)C(C#N)=C3)C(F)(F)F)CC2)=C1Cl KYKUZLYNQFQIOE-CQSZACIVSA-N 0.000 claims 1
- XFOGJOPEXUFLMR-LJQANCHMSA-N 5-cyano-n-[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-6-oxo-2-phenyl-1h-pyridine-3-carboxamide Chemical compound C([C@@H](O)CN1CCC(CC1)OC=1C=C(Cl)C(Cl)=CC=1)NC(=O)C=1C=C(C#N)C(=O)NC=1C1=CC=CC=C1 XFOGJOPEXUFLMR-LJQANCHMSA-N 0.000 claims 1
- 102000019034 Chemokines Human genes 0.000 claims 1
- 108010012236 Chemokines Proteins 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000007822 coupling agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- OJYWNWHKLHPIBG-CYBMUJFWSA-N n-[(2r)-3-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]-2-hydroxypropyl]-5-methyl-2h-triazole-4-carboxamide Chemical compound N1N=NC(C(=O)NC[C@@H](O)CN2CCC(CC2)OC=2C(=C(C)C(Cl)=CC=2)Cl)=C1C OJYWNWHKLHPIBG-CYBMUJFWSA-N 0.000 claims 1
- WFADFYKUSBNUOU-GFCCVEGCSA-N n-[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-2,6-dioxo-3-(2,2,2-trifluoroethyl)pyrimidine-4-carboxamide Chemical compound C([C@@H](O)CN1CCC(CC1)OC=1C=C(Cl)C(Cl)=CC=1)NC(=O)C1=CC(=O)NC(=O)N1CC(F)(F)F WFADFYKUSBNUOU-GFCCVEGCSA-N 0.000 claims 1
- TVYZNSWSXBUAEM-LLVKDONJSA-N n-[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-2-(methanesulfonamido)-4-(trifluoromethyl)-1,3-thiazole-5-carboxamide Chemical compound S1C(NS(=O)(=O)C)=NC(C(F)(F)F)=C1C(=O)NC[C@@H](O)CN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 TVYZNSWSXBUAEM-LLVKDONJSA-N 0.000 claims 1
- KZGSUHLKQJQXGW-SNVBAGLBSA-N n-[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-2-oxo-4-(1,1,2,2,2-pentafluoroethyl)-3h-1,3-thiazole-5-carboxamide Chemical compound C([C@@H](O)CN1CCC(CC1)OC=1C=C(Cl)C(Cl)=CC=1)NC(=O)C=1SC(=O)NC=1C(F)(F)C(F)(F)F KZGSUHLKQJQXGW-SNVBAGLBSA-N 0.000 claims 1
- RQCKUHXTTDXQAM-LLVKDONJSA-N n-[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-2-oxo-4-(2,2,2-trifluoroethyl)-3h-1,3-thiazole-5-carboxamide Chemical compound C([C@@H](O)CN1CCC(CC1)OC=1C=C(Cl)C(Cl)=CC=1)NC(=O)C=1SC(=O)NC=1CC(F)(F)F RQCKUHXTTDXQAM-LLVKDONJSA-N 0.000 claims 1
- UQLANKZJFFQJEG-SNVBAGLBSA-N n-[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-2-oxo-4-(trifluoromethyl)-3h-1,3-oxazole-5-carboxamide Chemical compound C([C@@H](O)CN1CCC(CC1)OC=1C=C(Cl)C(Cl)=CC=1)NC(=O)C=1OC(=O)NC=1C(F)(F)F UQLANKZJFFQJEG-SNVBAGLBSA-N 0.000 claims 1
- UHIOLFSGUPBJGD-SNVBAGLBSA-N n-[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-2-oxo-4-(trifluoromethyl)-3h-1,3-thiazole-5-carboxamide Chemical compound C([C@@H](O)CN1CCC(CC1)OC=1C=C(Cl)C(Cl)=CC=1)NC(=O)C=1SC(=O)NC=1C(F)(F)F UHIOLFSGUPBJGD-SNVBAGLBSA-N 0.000 claims 1
- NNZWVLZVFZRYAW-CQSZACIVSA-N n-[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-2-oxo-4-pyridin-2-yl-3h-1,3-thiazole-5-carboxamide Chemical compound C([C@@H](O)CN1CCC(CC1)OC=1C=C(Cl)C(Cl)=CC=1)NC(=O)C=1SC(=O)NC=1C1=CC=CC=N1 NNZWVLZVFZRYAW-CQSZACIVSA-N 0.000 claims 1
- YDGLTOMMMDYFCF-GFCCVEGCSA-N n-[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-3-methyl-2,6-dioxopyrimidine-4-carboxamide Chemical compound O=C1NC(=O)N(C)C(C(=O)NC[C@@H](O)CN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1 YDGLTOMMMDYFCF-GFCCVEGCSA-N 0.000 claims 1
- ZYKYTTXSPDZGCD-MRXNPFEDSA-N n-[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-4-(4-fluorophenyl)-2-oxo-3h-1,3-thiazole-5-carboxamide Chemical compound C([C@@H](O)CN1CCC(CC1)OC=1C=C(Cl)C(Cl)=CC=1)NC(=O)C=1SC(=O)NC=1C1=CC=C(F)C=C1 ZYKYTTXSPDZGCD-MRXNPFEDSA-N 0.000 claims 1
- NYQNNVWMTKXMKQ-LLVKDONJSA-N n-[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-5-(2,2,2-trifluoroethylsulfanyl)-2h-triazole-4-carboxamide Chemical compound C([C@@H](O)CN1CCC(CC1)OC=1C=C(Cl)C(Cl)=CC=1)NC(=O)C=1N=NNC=1SCC(F)(F)F NYQNNVWMTKXMKQ-LLVKDONJSA-N 0.000 claims 1
- FLGNGCOGAKLZBC-MRXNPFEDSA-N n-[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-5-(4-fluorophenyl)-2h-triazole-4-carboxamide Chemical compound C([C@@H](O)CN1CCC(CC1)OC=1C=C(Cl)C(Cl)=CC=1)NC(=O)C=1N=NNC=1C1=CC=C(F)C=C1 FLGNGCOGAKLZBC-MRXNPFEDSA-N 0.000 claims 1
- TYUNFNISYAKKIX-SNVBAGLBSA-N n-[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-5-(trifluoromethyl)-2h-triazole-4-carboxamide Chemical compound C([C@@H](O)CN1CCC(CC1)OC=1C=C(Cl)C(Cl)=CC=1)NC(=O)C=1N=NNC=1C(F)(F)F TYUNFNISYAKKIX-SNVBAGLBSA-N 0.000 claims 1
- PHAFYOKYSKPJTL-GFCCVEGCSA-N n-[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-5-[methyl(methylsulfonyl)amino]-2h-triazole-4-carboxamide Chemical compound N1N=NC(C(=O)NC[C@@H](O)CN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1N(C)S(C)(=O)=O PHAFYOKYSKPJTL-GFCCVEGCSA-N 0.000 claims 1
- NAVNNIOWFLLHDB-GFCCVEGCSA-N n-[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-5-methyl-2h-triazole-4-carboxamide Chemical compound N1N=NC(C(=O)NC[C@@H](O)CN2CCC(CC2)OC=2C=C(Cl)C(Cl)=CC=2)=C1C NAVNNIOWFLLHDB-GFCCVEGCSA-N 0.000 claims 1
- RNANWUAPUGGJOO-CYBMUJFWSA-N n-[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-6-(methanesulfonamido)-4-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1=NC(NS(=O)(=O)C)=CC(C(F)(F)F)=C1C(=O)NC[C@@H](O)CN1CCC(OC=2C=C(Cl)C(Cl)=CC=2)CC1 RNANWUAPUGGJOO-CYBMUJFWSA-N 0.000 claims 1
- SXSLEQOEDQRECX-GFCCVEGCSA-N n-[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-6-oxo-2-(1,1,2,2,2-pentafluoroethyl)-1h-pyridine-3-carboxamide Chemical compound C([C@@H](O)CN1CCC(CC1)OC=1C=C(Cl)C(Cl)=CC=1)NC(=O)C=1C=CC(=O)NC=1C(F)(F)C(F)(F)F SXSLEQOEDQRECX-GFCCVEGCSA-N 0.000 claims 1
- BWRVXHFDCPMWHN-GFCCVEGCSA-N n-[(2r)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-6-oxo-2-(trifluoromethyl)-1h-pyridine-3-carboxamide Chemical compound C([C@@H](O)CN1CCC(CC1)OC=1C=C(Cl)C(Cl)=CC=1)NC(=O)C=1C=CC(=O)NC=1C(F)(F)F BWRVXHFDCPMWHN-GFCCVEGCSA-N 0.000 claims 1
- GXTPOLBOFOWUPI-CYBMUJFWSA-N n-[(2r)-3-[4-(3-chloro-4-cyano-2-methylphenoxy)piperidin-1-yl]-2-hydroxypropyl]-2-oxo-4-(trifluoromethyl)-3h-1,3-thiazole-5-carboxamide Chemical compound C1=CC(C#N)=C(Cl)C(C)=C1OC1CCN(C[C@H](O)CNC(=O)C2=C(NC(=O)S2)C(F)(F)F)CC1 GXTPOLBOFOWUPI-CYBMUJFWSA-N 0.000 claims 1
- XEJKYPVHFJYWHN-GFCCVEGCSA-N n-[(2r)-3-[4-(3-chloro-4-cyanophenoxy)piperidin-1-yl]-2-hydroxypropyl]-2-oxo-4-(trifluoromethyl)-3h-1,3-thiazole-5-carboxamide Chemical compound C([C@@H](O)CN1CCC(CC1)OC=1C=C(Cl)C(C#N)=CC=1)NC(=O)C=1SC(=O)NC=1C(F)(F)F XEJKYPVHFJYWHN-GFCCVEGCSA-N 0.000 claims 1
- JQHHMHKVBIWTTB-CYBMUJFWSA-N n-[(2r)-3-[4-(4-chloro-2-methylphenoxy)piperidin-1-yl]-2-hydroxypropyl]-2-oxo-4-(trifluoromethyl)-3h-1,3-thiazole-5-carboxamide Chemical compound CC1=CC(Cl)=CC=C1OC1CCN(C[C@H](O)CNC(=O)C2=C(NC(=O)S2)C(F)(F)F)CC1 JQHHMHKVBIWTTB-CYBMUJFWSA-N 0.000 claims 1
- WZSPGELGEZNQCG-GFCCVEGCSA-N n-[(2s)-3-[4-(2,4-dichloro-3-methylphenoxy)piperidin-1-yl]-2-hydroxypropyl]-n-methyl-2-oxo-4-(trifluoromethyl)-3h-1,3-thiazole-5-carboxamide Chemical compound C([C@H](O)CN(C)C(=O)C1=C(NC(=O)S1)C(F)(F)F)N(CC1)CCC1OC1=CC=C(Cl)C(C)=C1Cl WZSPGELGEZNQCG-GFCCVEGCSA-N 0.000 claims 1
- UHIOLFSGUPBJGD-JTQLQIEISA-N n-[(2s)-3-[4-(3,4-dichlorophenoxy)piperidin-1-yl]-2-hydroxypropyl]-2-oxo-4-(trifluoromethyl)-3h-1,3-thiazole-5-carboxamide Chemical compound C([C@H](O)CN1CCC(CC1)OC=1C=C(Cl)C(Cl)=CC=1)NC(=O)C=1SC(=O)NC=1C(F)(F)F UHIOLFSGUPBJGD-JTQLQIEISA-N 0.000 claims 1
- XYJQQMADOHSQSP-CYBMUJFWSA-N n-[(2s)-3-[4-(3-chloro-4-cyanophenoxy)piperidin-1-yl]-2-hydroxypropyl]-n-methyl-2-oxo-4-(trifluoromethyl)-3h-1,3-thiazole-5-carboxamide Chemical compound C([C@H](O)CN(C)C(=O)C1=C(NC(=O)S1)C(F)(F)F)N(CC1)CCC1OC1=CC=C(C#N)C(Cl)=C1 XYJQQMADOHSQSP-CYBMUJFWSA-N 0.000 claims 1
- CDASZXHADOJOOL-MRXNPFEDSA-N n-[(2s)-3-[4-(3-chloro-4-cyanophenoxy)piperidin-1-yl]-2-hydroxypropyl]-n-methyl-5-propan-2-yl-2h-triazole-4-carboxamide Chemical compound N1N=NC(C(=O)N(C)C[C@@H](O)CN2CCC(CC2)OC=2C=C(Cl)C(C#N)=CC=2)=C1C(C)C CDASZXHADOJOOL-MRXNPFEDSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0400208-5 | 2004-02-02 | ||
| SE0400208A SE0400208D0 (sv) | 2004-02-02 | 2004-02-02 | Chemical compounds |
| PCT/SE2005/000110 WO2005073192A1 (en) | 2004-02-02 | 2005-01-31 | Novel piperidines as chemokine modulators (ccr) |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008226791A Division JP2009019055A (ja) | 2004-02-02 | 2008-09-04 | ケモカイン・モジュレーター（ｃｃｒ）としての新規ピペリジン類 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007519717A JP2007519717A (ja) | 2007-07-19 |
| JP2007519717A5 true JP2007519717A5 (https=) | 2007-10-25 |
| JP4814109B2 JP4814109B2 (ja) | 2011-11-16 |
Family
ID=31713276
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006551005A Expired - Fee Related JP4814109B2 (ja) | 2004-02-02 | 2005-01-31 | ケモカイン・モジュレーター（ｃｃｒ）としての新規ピペリジン類 |
| JP2008226791A Pending JP2009019055A (ja) | 2004-02-02 | 2008-09-04 | ケモカイン・モジュレーター（ｃｃｒ）としての新規ピペリジン類 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008226791A Pending JP2009019055A (ja) | 2004-02-02 | 2008-09-04 | ケモカイン・モジュレーター（ｃｃｒ）としての新規ピペリジン類 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7956070B2 (https=) |
| EP (1) | EP1713772A1 (https=) |
| JP (2) | JP4814109B2 (https=) |
| KR (1) | KR20060128992A (https=) |
| CN (1) | CN1938274A (https=) |
| AR (1) | AR049770A1 (https=) |
| AU (2) | AU2005207817B2 (https=) |
| BR (1) | BRPI0507366A (https=) |
| CA (1) | CA2553089A1 (https=) |
| CO (1) | CO5700747A2 (https=) |
| IL (1) | IL176992A0 (https=) |
| NO (1) | NO20063921L (https=) |
| NZ (1) | NZ548781A (https=) |
| RU (2) | RU2348616C2 (https=) |
| SE (1) | SE0400208D0 (https=) |
| TW (1) | TW200529843A (https=) |
| UY (1) | UY28731A1 (https=) |
| WO (1) | WO2005073192A1 (https=) |
| ZA (1) | ZA200606199B (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
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| TW200303304A (en) * | 2002-02-18 | 2003-09-01 | Astrazeneca Ab | Chemical compounds |
| SE0400208D0 (sv) * | 2004-02-02 | 2004-02-02 | Astrazeneca Ab | Chemical compounds |
| TW200812582A (en) * | 2006-04-06 | 2008-03-16 | Astrazeneca Ab | Medicaments |
| US7897621B2 (en) | 2008-03-31 | 2011-03-01 | Hoffmann-La Roche Inc. | 2-trifluoromethylnicotinamide derivatives as HDL-cholesterol raising agents |
| TWI433838B (zh) * | 2008-06-25 | 2014-04-11 | 必治妥美雅史谷比公司 | 作為趨化因子受體活性調節劑之六氫吡啶衍生物 |
| US8410107B2 (en) | 2010-10-15 | 2013-04-02 | Hoffmann-La Roche Inc. | N-pyridin-3-yl or N-pyrazin-2-yl carboxamides |
| US8669254B2 (en) | 2010-12-15 | 2014-03-11 | Hoffman-La Roche Inc. | Pyridine, pyridazine, pyrimidine or pyrazine carboxamides as HDL-cholesterol raising agents |
| TW201418242A (zh) | 2012-10-26 | 2014-05-16 | Du Pont | 作為除草劑之經取代的三唑 |
| US20160002204A1 (en) * | 2014-07-03 | 2016-01-07 | Board Of Regents, The University Of Texas System | Gls1 inhibitors for treating disease |
| AU2015283850B2 (en) | 2014-07-03 | 2020-06-04 | Board Of Regents, University Of Texas System | GLS1 inhibitors for treating disease |
| ES2794868T3 (es) | 2015-06-30 | 2020-11-19 | Univ Texas | Inhibidores de GLS1 para el tratamiento de enfermedades |
| JP6976248B2 (ja) | 2015-12-22 | 2021-12-08 | ボード オブ リージェンツ、ザ ユニバーシテイ オブ テキサス システム | （ｒ）−１−（４−（６−（２−（４−（３，３−ジフルオロシクロブトキシ）−６−メチルピリジン−２−イル）アセトアミド）ピリダジン−３−イル）−２−フルオロブチル）−ｎ−メチル−１ｈ−１，２，３−トリアゾール−４−カルボキサミドの塩形態および多形体 |
| RU2020112558A (ru) | 2017-10-18 | 2021-11-18 | Боард Оф Регентс, Зе Юниверсити Оф Тексас Систем | Терапия на основе ингибитора глутаминазы |
| WO2020025574A1 (en) | 2018-08-03 | 2020-02-06 | Bayer Aktiengesellschaft | Process for the preparation of 6-(haloalkyl)-2-halo-5-acylpyridines and intermediates for this process |
| CN113121417A (zh) * | 2019-12-30 | 2021-07-16 | 苏州盛迪亚生物医药有限公司 | 一种新型哌啶衍生物及其药物用途 |
| WO2025118148A1 (en) * | 2023-12-05 | 2025-06-12 | Biofront Ltd | Antioxidant drug-conjugate modulators of fpr1, compositions comprising the modulator, and methods of using the same |
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| FR2676054B1 (fr) * | 1991-05-03 | 1993-09-03 | Sanofi Elf | Nouveaux composes n-alkylenepiperidino et leurs enantiomeres, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| IL118768A (en) * | 1995-07-12 | 2000-10-31 | Akzo Nobel Nv | Diphenylmethane piperidine derivatives pharmaceutical compositions containing them and a method for their preparation |
| JPH0977742A (ja) | 1995-09-12 | 1997-03-25 | Kyorin Pharmaceut Co Ltd | 新規なベンズアミド誘導体 |
| ZA9610738B (en) | 1995-12-22 | 1997-06-24 | Warner Lambert Co | Subtype selective nmda receptor ligands and the use thereof |
| JP2001507673A (ja) | 1996-10-28 | 2001-06-12 | シェーリング コーポレイション | ニューロキニンアンタゴニストとしての置換アリールアルキルアミン |
| US6124319A (en) * | 1997-01-21 | 2000-09-26 | Merck & Co., Inc. | 3,3-disubstituted piperidines as modulators of chemokine receptor activity |
| CA2296314A1 (en) | 1997-07-25 | 1999-02-04 | Merck & Co., Inc. | Cyclic amine modulators of chemokine receptor activity |
| IL125658A0 (en) | 1997-08-18 | 1999-04-11 | Hoffmann La Roche | Ccr-3 receptor antagonists |
| US6166037A (en) * | 1997-08-28 | 2000-12-26 | Merck & Co., Inc. | Pyrrolidine and piperidine modulators of chemokine receptor activity |
| US6140349A (en) * | 1998-02-02 | 2000-10-31 | Merck & Co., Inc. | Cyclic amine modulators of chemokine receptor activity |
| GB9919776D0 (en) | 1998-08-31 | 1999-10-27 | Zeneca Ltd | Compoujnds |
| ES2230899T3 (es) | 1998-11-17 | 2005-05-01 | F. Hoffmann-La Roche Ag | Antagonistas iii receptores de 4-aroil-piperidin-ccr-3. |
| JP3421323B2 (ja) * | 1998-11-20 | 2003-06-30 | エフ．ホフマン−ラ ロシュ アーゲー | ピペリジンｃｃｒ−３受容体拮抗薬 |
| US6486180B1 (en) | 1998-12-18 | 2002-11-26 | Bristol-Myers Squibb Pharma Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| US6331541B1 (en) * | 1998-12-18 | 2001-12-18 | Soo S. Ko | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| DE69926806D1 (de) | 1998-12-18 | 2005-09-22 | Bristol Myers Squibb Pharma Co | N-ureidoalkylpiperidine als modulatoren der aktivität der chemokinrezeptoren |
| WO2000035449A1 (en) | 1998-12-18 | 2000-06-22 | Du Pont Pharmaceuticals Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| CA2350730A1 (en) | 1998-12-18 | 2000-06-22 | George V. Delucca | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| US6605623B1 (en) * | 1998-12-18 | 2003-08-12 | Bristol-Myers Squibb Pharma Co. | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| US6492400B1 (en) | 1998-12-18 | 2002-12-10 | Bristol-Myers Squibb Pharma Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| AU3386400A (en) * | 1999-03-02 | 2000-09-21 | Merck & Co., Inc. | 3-alkyl substituted pyrrolidine modulators of chemokine receptor activity |
| BR0009338A (pt) | 1999-03-26 | 2001-12-26 | Astrazeneca Ab | Composto, processo para a preparação do mesmo,composição farmacêutica, processo para apreparação da mesma, uso de um composto, e,método de tratamento de uma doençainflamatória em um paciente sofrendo ou em riscode dita doença |
| US6358979B1 (en) * | 1999-06-11 | 2002-03-19 | Merck & Co., Inc. | N-cyclopentyl modulators of chemokine receptor activity |
| SE9902551D0 (sv) | 1999-07-02 | 1999-07-02 | Astra Pharma Prod | Novel compounds |
| SE9902765D0 (sv) | 1999-07-21 | 1999-07-21 | Astra Pharma Prod | Novel compounds |
| CO5300399A1 (es) | 2000-02-25 | 2003-07-31 | Astrazeneca Ab | Heterocicliocs que contienen nitrogeno, proceso para su preparacion y composiciones farmaceuticas que los contienen |
| AR033517A1 (es) | 2000-04-08 | 2003-12-26 | Astrazeneca Ab | Derivados de piperidina, proceso para su preparacion y uso de estos derivados en la fabricacion de medicamentos |
| CA2413274A1 (en) | 2000-06-21 | 2001-12-27 | George V. Delucca | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
| JP2004516238A (ja) | 2000-06-21 | 2004-06-03 | ブリストル−マイヤーズ・スクイブ・ファーマ・カンパニー | ケモカイン受容体活性調節剤としてのｎ−ウレイドアルキル−ピペリジン |
| JP2004517805A (ja) * | 2000-06-30 | 2004-06-17 | ブリストル−マイヤーズ・スクイブ・ファーマ・カンパニー | ケモカイン受容体活性調節剤としてのｎ−ウレイドヘテロシクロアルキル−ピペリジン |
| GB0021670D0 (en) | 2000-09-04 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
| US6855553B1 (en) | 2000-10-02 | 2005-02-15 | 3M Innovative Properties Company | Sample processing apparatus, methods and systems |
| WO2002030899A1 (en) * | 2000-10-09 | 2002-04-18 | Novartis Ag | N-(4-aryloxypiperidin-1-ylalkyl) cinnamic amides as ccr3 receptor antagonists |
| MXPA03004652A (es) | 2000-12-21 | 2003-09-05 | Warner Lambert Co | Derivados de piperidina como antagonistas selectivos de subtipo de n-metil-d-aspartato. |
| GB0117899D0 (en) | 2001-07-23 | 2001-09-12 | Astrazeneca Ab | Chemical compounds |
| TW200303304A (en) * | 2002-02-18 | 2003-09-01 | Astrazeneca Ab | Chemical compounds |
| AU2003215024B2 (en) | 2002-03-26 | 2008-02-21 | Merck Sharp & Dohme Corp. | Spirocyclic amides as cannabinoid receptor modulators |
| SE0400208D0 (sv) | 2004-02-02 | 2004-02-02 | Astrazeneca Ab | Chemical compounds |
| TW200812582A (en) | 2006-04-06 | 2008-03-16 | Astrazeneca Ab | Medicaments |
-
2004
- 2004-02-02 SE SE0400208A patent/SE0400208D0/xx unknown
-
2005
- 2005-01-31 CN CNA2005800103948A patent/CN1938274A/zh active Pending
- 2005-01-31 WO PCT/SE2005/000110 patent/WO2005073192A1/en not_active Ceased
- 2005-01-31 AU AU2005207817A patent/AU2005207817B2/en not_active Ceased
- 2005-01-31 US US10/587,633 patent/US7956070B2/en not_active Expired - Fee Related
- 2005-01-31 KR KR1020067015578A patent/KR20060128992A/ko not_active Withdrawn
- 2005-01-31 UY UY28731A patent/UY28731A1/es unknown
- 2005-01-31 NZ NZ548781A patent/NZ548781A/en unknown
- 2005-01-31 JP JP2006551005A patent/JP4814109B2/ja not_active Expired - Fee Related
- 2005-01-31 CA CA002553089A patent/CA2553089A1/en not_active Abandoned
- 2005-01-31 BR BRPI0507366-9A patent/BRPI0507366A/pt not_active IP Right Cessation
- 2005-01-31 EP EP05704776A patent/EP1713772A1/en not_active Withdrawn
- 2005-01-31 RU RU2006130686/04A patent/RU2348616C2/ru not_active IP Right Cessation
- 2005-02-01 TW TW094103106A patent/TW200529843A/zh unknown
- 2005-02-02 AR ARP050100391A patent/AR049770A1/es unknown
-
2006
- 2006-07-20 IL IL176992A patent/IL176992A0/en unknown
- 2006-07-26 ZA ZA200606199A patent/ZA200606199B/xx unknown
- 2006-07-27 CO CO06073840A patent/CO5700747A2/es not_active Application Discontinuation
- 2006-09-01 NO NO20063921A patent/NO20063921L/no not_active Application Discontinuation
-
2008
- 2008-09-04 JP JP2008226791A patent/JP2009019055A/ja active Pending
- 2008-10-09 AU AU2008229856A patent/AU2008229856A1/en not_active Abandoned
- 2008-10-16 RU RU2008140910/04A patent/RU2008140910A/ru not_active Application Discontinuation
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