ES2291913T3 - Piperidinas sustituidas como ligandos del receptor h3 de la histamina. - Google Patents
Piperidinas sustituidas como ligandos del receptor h3 de la histamina. Download PDFInfo
- Publication number
- ES2291913T3 ES2291913T3 ES04763339T ES04763339T ES2291913T3 ES 2291913 T3 ES2291913 T3 ES 2291913T3 ES 04763339 T ES04763339 T ES 04763339T ES 04763339 T ES04763339 T ES 04763339T ES 2291913 T3 ES2291913 T3 ES 2291913T3
- Authority
- ES
- Spain
- Prior art keywords
- piperidinyl
- oxy
- cyclobutyl
- phenyl
- methylethyl
- 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.)
- Expired - Lifetime
Links
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 title description 22
- 229960001340 histamine Drugs 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 219
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 64
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 150000002367 halogens Chemical class 0.000 claims abstract description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 10
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 5
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 5
- 125000005533 aryl carboxamido group Chemical group 0.000 claims abstract description 5
- 125000005421 aryl sulfonamido group Chemical group 0.000 claims abstract description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 5
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims abstract description 5
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 5
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims abstract description 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract description 3
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims abstract description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 3
- 235000019256 formaldehyde Nutrition 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
- -1 3-methyl-1,2,4-oxadiazol-5-yl Chemical group 0.000 claims description 64
- 238000000034 method Methods 0.000 claims description 50
- 238000011282 treatment Methods 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 7
- ROFRIKRDIUUGLL-UHFFFAOYSA-N 3-methyl-5-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxypiperidin-1-yl]phenyl]-1,2,4-oxadiazole Chemical compound C1CN(C(C)C)CCC1OC1CCN(C=2C=CC(=CC=2)C=2ON=C(C)N=2)CC1 ROFRIKRDIUUGLL-UHFFFAOYSA-N 0.000 claims description 6
- HCSPMMJLAZYFCT-UHFFFAOYSA-N 5-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-2-(trifluoromethyl)pyrimidine Chemical compound C1=NC(C(F)(F)F)=NC=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 HCSPMMJLAZYFCT-UHFFFAOYSA-N 0.000 claims description 6
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 6
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- NRYGWLNOBIXJSR-UHFFFAOYSA-N 1-[4-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 NRYGWLNOBIXJSR-UHFFFAOYSA-N 0.000 claims description 4
- OZVHWEBXGRMQJH-UHFFFAOYSA-N 1-[4-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]phenyl]propan-1-one Chemical compound C1=CC(C(=O)CC)=CC=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 OZVHWEBXGRMQJH-UHFFFAOYSA-N 0.000 claims description 4
- CKAFQVKVZGKTDU-UHFFFAOYSA-N 1-[6-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]pyridin-3-yl]ethanone Chemical compound N1=CC(C(=O)C)=CC=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 CKAFQVKVZGKTDU-UHFFFAOYSA-N 0.000 claims description 4
- FHFVWWQXKNQESI-UHFFFAOYSA-N 3-[4-(1-propan-2-ylpiperidin-4-yl)oxypiperidin-1-yl]-6-(trifluoromethyl)pyridazine Chemical compound C1CN(C(C)C)CCC1OC1CCN(C=2N=NC(=CC=2)C(F)(F)F)CC1 FHFVWWQXKNQESI-UHFFFAOYSA-N 0.000 claims description 4
- OBYBVWBWVBQDEC-UHFFFAOYSA-N 5-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 OBYBVWBWVBQDEC-UHFFFAOYSA-N 0.000 claims description 4
- QELYONVDPGLLTR-UHFFFAOYSA-N 5-[4-(1-propan-2-ylpiperidin-4-yl)oxypiperidin-1-yl]-2-(trifluoromethyl)pyrimidine Chemical compound C1CN(C(C)C)CCC1OC1CCN(C=2C=NC(=NC=2)C(F)(F)F)CC1 QELYONVDPGLLTR-UHFFFAOYSA-N 0.000 claims description 4
- 208000012902 Nervous system disease Diseases 0.000 claims description 4
- 208000025966 Neurological disease Diseases 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
- QLZASUPJZXESTL-UHFFFAOYSA-N 3-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-6-(trifluoromethyl)pyridazine Chemical compound N1=NC(C(F)(F)F)=CC=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 QLZASUPJZXESTL-UHFFFAOYSA-N 0.000 claims description 3
- NGOKAJIBXGBPOT-UHFFFAOYSA-N 4-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-2,5-difluorobenzonitrile Chemical compound C1=C(C#N)C(F)=CC(N2CCC(CC2)OC2CCN(CC2)C2CCC2)=C1F NGOKAJIBXGBPOT-UHFFFAOYSA-N 0.000 claims description 3
- NGGWOMNGFFBIFB-UHFFFAOYSA-N 4-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-2-fluorobenzonitrile Chemical compound C1=C(C#N)C(F)=CC(N2CCC(CC2)OC2CCN(CC2)C2CCC2)=C1 NGGWOMNGFFBIFB-UHFFFAOYSA-N 0.000 claims description 3
- PTGRQFAOWCPNOU-UHFFFAOYSA-N 5-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-n-methylpyrazine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CN=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 PTGRQFAOWCPNOU-UHFFFAOYSA-N 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- DDHAOEHMWHNXMW-UHFFFAOYSA-N 1-[4-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-2,5-difluorophenyl]ethanone Chemical compound C1=C(F)C(C(=O)C)=CC(F)=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 DDHAOEHMWHNXMW-UHFFFAOYSA-N 0.000 claims description 2
- KVNZOLNEBSJBLH-UHFFFAOYSA-N 1-[4-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-2-fluorophenyl]ethanone Chemical compound C1=C(F)C(C(=O)C)=CC=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 KVNZOLNEBSJBLH-UHFFFAOYSA-N 0.000 claims description 2
- NMQKODJYPGFWOV-UHFFFAOYSA-N 1-[4-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-3-fluorophenyl]ethanone Chemical compound FC1=CC(C(=O)C)=CC=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 NMQKODJYPGFWOV-UHFFFAOYSA-N 0.000 claims description 2
- KTEDTUDAJHHPMC-UHFFFAOYSA-N 1-[4-[4-[1-(cyclopropylmethyl)piperidin-4-yl]oxypiperidin-1-yl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1N1CCC(OC2CCN(CC3CC3)CC2)CC1 KTEDTUDAJHHPMC-UHFFFAOYSA-N 0.000 claims description 2
- OFSOWRWVXOGACO-QGZVFWFLSA-N 1-[4-[4-[1-[(2r)-butan-2-yl]piperidin-4-yl]oxypiperidin-1-yl]phenyl]ethanone Chemical compound C1CN([C@H](C)CC)CCC1OC1CCN(C=2C=CC(=CC=2)C(C)=O)CC1 OFSOWRWVXOGACO-QGZVFWFLSA-N 0.000 claims description 2
- OFSOWRWVXOGACO-KRWDZBQOSA-N 1-[4-[4-[1-[(2s)-butan-2-yl]piperidin-4-yl]oxypiperidin-1-yl]phenyl]ethanone Chemical compound C1CN([C@@H](C)CC)CCC1OC1CCN(C=2C=CC(=CC=2)C(C)=O)CC1 OFSOWRWVXOGACO-KRWDZBQOSA-N 0.000 claims description 2
- TYCOBGWRHMHZRO-UHFFFAOYSA-N 1-[5-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]pyridin-2-yl]ethanone Chemical compound C1=NC(C(=O)C)=CC=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 TYCOBGWRHMHZRO-UHFFFAOYSA-N 0.000 claims description 2
- VPMYIUDGEAIUTP-UHFFFAOYSA-N 4-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-3-fluorobenzonitrile Chemical compound FC1=CC(C#N)=CC=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 VPMYIUDGEAIUTP-UHFFFAOYSA-N 0.000 claims description 2
- HPUNGTVILPJQDG-UHFFFAOYSA-N 5-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-n-ethylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NCC)=CC=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 HPUNGTVILPJQDG-UHFFFAOYSA-N 0.000 claims description 2
- JYAQKCCNFKDLJR-UHFFFAOYSA-N 5-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-n-propan-2-ylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC(C)C)=CC=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 JYAQKCCNFKDLJR-UHFFFAOYSA-N 0.000 claims description 2
- NCWCDKYOVWQMFL-UHFFFAOYSA-N 5-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-n-propylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NCCC)=CC=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 NCWCDKYOVWQMFL-UHFFFAOYSA-N 0.000 claims description 2
- VCTFYNBGWHVGSZ-UHFFFAOYSA-N 5-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]pyridine-2-carbonitrile Chemical compound C1=NC(C#N)=CC=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 VCTFYNBGWHVGSZ-UHFFFAOYSA-N 0.000 claims description 2
- KNYMTEQKMUCWSG-UHFFFAOYSA-N 5-[4-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-2-fluorophenyl]-3-methyl-1,2,4-oxadiazole Chemical compound CC1=NOC(C=2C(=CC(=CC=2)N2CCC(CC2)OC2CCN(CC2)C2CCC2)F)=N1 KNYMTEQKMUCWSG-UHFFFAOYSA-N 0.000 claims description 2
- KVAUYGITJXIYNL-INIZCTEOSA-N 5-[4-[4-[1-[(2s)-butan-2-yl]piperidin-4-yl]oxypiperidin-1-yl]-2-fluorophenyl]-3-methyl-1,2,4-oxadiazole Chemical compound C1CN([C@@H](C)CC)CCC1OC1CCN(C=2C=C(F)C(C=3ON=C(C)N=3)=CC=2)CC1 KVAUYGITJXIYNL-INIZCTEOSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OCLNWKWOQXMNRF-UHFFFAOYSA-N n-cyclobutyl-5-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]pyridine-2-carboxamide Chemical compound C=1C=C(N2CCC(CC2)OC2CCN(CC2)C2CCC2)C=NC=1C(=O)NC1CCC1 OCLNWKWOQXMNRF-UHFFFAOYSA-N 0.000 claims description 2
- UXYSVECFZJVXGI-UHFFFAOYSA-N n-cyclobutyl-5-[4-(1-propan-2-ylpiperidin-4-yl)oxypiperidin-1-yl]pyridine-2-carboxamide Chemical compound C1CN(C(C)C)CCC1OC1CCN(C=2C=NC(=CC=2)C(=O)NC2CCC2)CC1 UXYSVECFZJVXGI-UHFFFAOYSA-N 0.000 claims description 2
- SZTIHZLYNVEXDI-UHFFFAOYSA-N n-methyl-5-[4-(1-propan-2-ylpiperidin-4-yl)oxypiperidin-1-yl]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1N1CCC(OC2CCN(CC2)C(C)C)CC1 SZTIHZLYNVEXDI-UHFFFAOYSA-N 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- GZSMPZFTPWGZAV-UHFFFAOYSA-N 1-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxypiperidin-1-yl]phenyl]ethanone Chemical compound C1CN(C(C)C)CCC1OC1CCN(C=2C=CC(=CC=2)C(C)=O)CC1 GZSMPZFTPWGZAV-UHFFFAOYSA-N 0.000 claims 1
- URIFVQONQHSSBL-UHFFFAOYSA-N 2-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-4-(trifluoromethyl)pyrimidine Chemical compound FC(F)(F)C1=CC=NC(N2CCC(CC2)OC2CCN(CC2)C2CCC2)=N1 URIFVQONQHSSBL-UHFFFAOYSA-N 0.000 claims 1
- ABHPBERICQJSJR-UHFFFAOYSA-N 2-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-5-(trifluoromethyl)pyrazine Chemical compound C1=NC(C(F)(F)F)=CN=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 ABHPBERICQJSJR-UHFFFAOYSA-N 0.000 claims 1
- NWZOOQCNQDPLMG-UHFFFAOYSA-N 2-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-5-(trifluoromethyl)pyridine Chemical compound N1=CC(C(F)(F)F)=CC=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 NWZOOQCNQDPLMG-UHFFFAOYSA-N 0.000 claims 1
- WFXQYBYRKJNSDD-UHFFFAOYSA-N 2-[4-(1-propan-2-ylpiperidin-4-yl)oxypiperidin-1-yl]-4-(trifluoromethyl)pyrimidine Chemical compound C1CN(C(C)C)CCC1OC1CCN(C=2N=C(C=CN=2)C(F)(F)F)CC1 WFXQYBYRKJNSDD-UHFFFAOYSA-N 0.000 claims 1
- NWAPROAXKWOBIW-UHFFFAOYSA-N 2-[4-(1-propan-2-ylpiperidin-4-yl)oxypiperidin-1-yl]-5-(trifluoromethyl)pyrazine Chemical compound C1CN(C(C)C)CCC1OC1CCN(C=2N=CC(=NC=2)C(F)(F)F)CC1 NWAPROAXKWOBIW-UHFFFAOYSA-N 0.000 claims 1
- MSJAQVJXNRYRAK-UHFFFAOYSA-N 2-[4-(1-propan-2-ylpiperidin-4-yl)oxypiperidin-1-yl]-5-(trifluoromethyl)pyridine Chemical compound C1CN(C(C)C)CCC1OC1CCN(C=2N=CC(=CC=2)C(F)(F)F)CC1 MSJAQVJXNRYRAK-UHFFFAOYSA-N 0.000 claims 1
- XGAVRTOMAILQTP-UHFFFAOYSA-N 2-[4-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]phenyl]-1,3-oxazole Chemical compound C1CCC1N1CCC(OC2CCN(CC2)C=2C=CC(=CC=2)C=2OC=CN=2)CC1 XGAVRTOMAILQTP-UHFFFAOYSA-N 0.000 claims 1
- RPNWZOMJXSNVPC-UHFFFAOYSA-N 2-[4-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]phenyl]-5-phenyl-1,3,4-oxadiazole Chemical compound C1CCC1N1CCC(OC2CCN(CC2)C=2C=CC(=CC=2)C=2OC(=NN=2)C=2C=CC=CC=2)CC1 RPNWZOMJXSNVPC-UHFFFAOYSA-N 0.000 claims 1
- GOSOVICNNIVEIE-UHFFFAOYSA-N 2-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxypiperidin-1-yl]phenyl]-1,3-oxazole Chemical compound C1CN(C(C)C)CCC1OC1CCN(C=2C=CC(=CC=2)C=2OC=CN=2)CC1 GOSOVICNNIVEIE-UHFFFAOYSA-N 0.000 claims 1
- DAOBUCDSENCWMD-UHFFFAOYSA-N 2-methyl-4-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxypiperidin-1-yl]phenyl]-1,3-oxazole Chemical compound C1CN(C(C)C)CCC1OC1CCN(C=2C=CC(=CC=2)C=2N=C(C)OC=2)CC1 DAOBUCDSENCWMD-UHFFFAOYSA-N 0.000 claims 1
- UIZQIELRPQDSJC-UHFFFAOYSA-N 2-methyl-5-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxypiperidin-1-yl]phenyl]-1,3-oxazole Chemical compound C1CN(C(C)C)CCC1OC1CCN(C=2C=CC(=CC=2)C=2OC(C)=NC=2)CC1 UIZQIELRPQDSJC-UHFFFAOYSA-N 0.000 claims 1
- HJJIQURPKIAODK-UHFFFAOYSA-N 2-phenyl-5-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxypiperidin-1-yl]phenyl]-1,3,4-oxadiazole Chemical compound C1CN(C(C)C)CCC1OC1CCN(C=2C=CC(=CC=2)C=2OC(=NN=2)C=2C=CC=CC=2)CC1 HJJIQURPKIAODK-UHFFFAOYSA-N 0.000 claims 1
- DHQDHXWCKMNJNC-UHFFFAOYSA-N 3-[4-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]phenyl]-5-methyl-1,2,4-oxadiazole Chemical compound O1C(C)=NC(C=2C=CC(=CC=2)N2CCC(CC2)OC2CCN(CC2)C2CCC2)=N1 DHQDHXWCKMNJNC-UHFFFAOYSA-N 0.000 claims 1
- UGDZIRZIWHRWAJ-UHFFFAOYSA-N 3-methyl-5-[4-[4-(1-propan-2-ylpiperidin-4-yl)oxypiperidin-1-yl]phenyl]-1,2-oxazole Chemical compound C1CN(C(C)C)CCC1OC1CCN(C=2C=CC(=CC=2)C=2ON=C(C)C=2)CC1 UGDZIRZIWHRWAJ-UHFFFAOYSA-N 0.000 claims 1
- DFFWIGMYIGIENQ-UHFFFAOYSA-N 4-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 DFFWIGMYIGIENQ-UHFFFAOYSA-N 0.000 claims 1
- CQOHFZPAHVRWNK-UHFFFAOYSA-N 4-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 CQOHFZPAHVRWNK-UHFFFAOYSA-N 0.000 claims 1
- PRDOOZACFSRFIG-UHFFFAOYSA-N 4-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-n-propan-2-ylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC(C)C)=CC(N2CCC(CC2)OC2CCN(CC2)C2CCC2)=C1 PRDOOZACFSRFIG-UHFFFAOYSA-N 0.000 claims 1
- UOQYAQNAXCHNMB-UHFFFAOYSA-N 4-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 UOQYAQNAXCHNMB-UHFFFAOYSA-N 0.000 claims 1
- RIRWRSQXDDJXDS-UHFFFAOYSA-N 4-[4-(1-propan-2-ylpiperidin-4-yl)oxypiperidin-1-yl]benzonitrile Chemical compound C1CN(C(C)C)CCC1OC1CCN(C=2C=CC(=CC=2)C#N)CC1 RIRWRSQXDDJXDS-UHFFFAOYSA-N 0.000 claims 1
- MYSLAYIJSIMHPI-UHFFFAOYSA-N 4-[4-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]phenyl]-2-methyl-1,3-oxazole Chemical compound O1C(C)=NC(C=2C=CC(=CC=2)N2CCC(CC2)OC2CCN(CC2)C2CCC2)=C1 MYSLAYIJSIMHPI-UHFFFAOYSA-N 0.000 claims 1
- WRVCCZJOIMVDLO-UHFFFAOYSA-N 5-[2-fluoro-4-[4-(1-propan-2-ylpiperidin-4-yl)oxypiperidin-1-yl]phenyl]-3-methyl-1,2,4-oxadiazole Chemical compound C1CN(C(C)C)CCC1OC1CCN(C=2C=C(F)C(C=3ON=C(C)N=3)=CC=2)CC1 WRVCCZJOIMVDLO-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
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- 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
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- 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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- 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Psychiatry (AREA)
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- Child & Adolescent Psychology (AREA)
- Anesthesiology (AREA)
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- Ophthalmology & Optometry (AREA)
- Obesity (AREA)
- Addiction (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0316893 | 2003-07-18 | ||
| GB0316893A GB0316893D0 (en) | 2003-07-18 | 2003-07-18 | Novel compounds |
| GB0411167A GB0411167D0 (en) | 2004-05-19 | 2004-05-19 | Novel compounds |
| GB0411167 | 2004-05-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2291913T3 true ES2291913T3 (es) | 2008-03-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04763339T Expired - Lifetime ES2291913T3 (es) | 2003-07-18 | 2004-07-16 | Piperidinas sustituidas como ligandos del receptor h3 de la histamina. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20060247227A1 (enExample) |
| EP (1) | EP1646620B1 (enExample) |
| JP (1) | JP2006528147A (enExample) |
| AR (1) | AR045999A1 (enExample) |
| AT (1) | ATE370135T1 (enExample) |
| DE (1) | DE602004008291T2 (enExample) |
| ES (1) | ES2291913T3 (enExample) |
| TW (1) | TW200514781A (enExample) |
| WO (1) | WO2005014571A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007010350A1 (en) * | 2005-07-19 | 2007-01-25 | Pfizer Products Inc. | Synthesis of therapeutic diphenyl ethers |
| JP2009506987A (ja) | 2005-08-02 | 2009-02-19 | ニューロゲン コーポレイション | ジピペラジニルケトンおよび関連する類似体 |
| CA2687931C (en) | 2007-05-31 | 2016-05-24 | Boehringer Ingelheim International Gmbh | Ccr2 receptor antagonists and uses thereof |
| EP2205588A2 (en) * | 2007-09-28 | 2010-07-14 | Schering Corporation | Oxypiperidine derivatives as histamine receptor antagonists |
| CN103724328B (zh) | 2008-12-19 | 2015-10-14 | 贝林格尔.英格海姆国际有限公司 | 作为ccr2受体拮抗剂用于治疗炎症、哮喘和copd的环状嘧啶-4-甲酰胺 |
| PL2513093T3 (pl) | 2009-12-17 | 2015-03-31 | Centrexion Therapeutics Corp | Nowi antagoniści receptora CCR2 i ich zastosowanie |
| EP2569295B1 (en) | 2010-05-12 | 2014-11-19 | Boehringer Ingelheim International GmbH | New ccr2 receptor antagonists, method for producing the same, and use thereof as medicaments |
| JP2013526507A (ja) | 2010-05-12 | 2013-06-24 | 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 | 新規ｃｃｒ２受容体アンタゴニスト、その製造方法及び薬物としてのその使用 |
| US8841313B2 (en) | 2010-05-17 | 2014-09-23 | Boehringer Ingelheim International Gmbh | CCR2 antagonists and uses thereof |
| CN102260277B (zh) | 2010-05-24 | 2013-07-24 | 中国科学院上海药物研究所 | 新型苯并噁嗪噁唑烷酮类化合物及其制备方法和用途 |
| 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 |
| EP2576538B1 (en) | 2010-06-01 | 2015-10-28 | Boehringer Ingelheim International GmbH | New CCR2 antagonists |
| CA2806341C (en) * | 2010-07-29 | 2020-03-24 | Rigel Pharmaceuticals, Inc. | Ampk-activating heterocyclic compounds and methods for using the same |
| WO2013010839A1 (en) | 2011-07-15 | 2013-01-24 | Boehringer Ingelheim International Gmbh | Novel and selective ccr2 antagonists |
| CA2863022A1 (en) * | 2012-01-16 | 2013-07-25 | Glaxosmithkline Intellectual Property Development Limited | Therapeutic uses |
| CN104114538B (zh) * | 2012-01-16 | 2016-04-13 | 葛兰素史克知识产权发展有限公司 | 治疗用途 |
| 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 |
| AU2016287584B2 (en) | 2015-07-02 | 2020-03-26 | 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 |
| WO2017095758A1 (en) * | 2015-12-01 | 2017-06-08 | Merck Sharp & Dohme Corp. | Homobispiperidinyl derivatives as liver x receptor beta agonists, compositions, and their use |
| AU2023247609A1 (en) * | 2022-03-31 | 2024-10-17 | Bebetter Med Inc. | 1,4-diheterocyclic substituted aromatic ring or aromatic heterocyclic compound and use thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20020507A1 (es) * | 2000-10-17 | 2002-06-25 | Schering Corp | Compuestos no-imidazoles como antagonistas del receptor histamina h3 |
| CA2436083A1 (en) * | 2001-02-08 | 2002-09-19 | Schering Corporation | Use of dual h3/m2 antagonists in the treatment of cognition deficit disorders |
| EP1444219A1 (en) * | 2001-10-12 | 2004-08-11 | Novo Nordisk A/S | Substituted piperidines and their use for the treatment of diseases related to the histamine h3 receptor |
| AU2003242252A1 (en) * | 2002-06-07 | 2003-12-22 | Kyowa Hakko Kogyo Co., Ltd. | Bicyclic pyrimidine derivatives |
-
2004
- 2004-07-16 AR ARP040102526A patent/AR045999A1/es unknown
- 2004-07-16 US US10/564,931 patent/US20060247227A1/en not_active Abandoned
- 2004-07-16 DE DE602004008291T patent/DE602004008291T2/de not_active Expired - Fee Related
- 2004-07-16 WO PCT/EP2004/008061 patent/WO2005014571A1/en not_active Ceased
- 2004-07-16 JP JP2006520762A patent/JP2006528147A/ja active Pending
- 2004-07-16 TW TW093121228A patent/TW200514781A/zh unknown
- 2004-07-16 EP EP04763339A patent/EP1646620B1/en not_active Expired - Lifetime
- 2004-07-16 AT AT04763339T patent/ATE370135T1/de not_active IP Right Cessation
- 2004-07-16 ES ES04763339T patent/ES2291913T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1646620B1 (en) | 2007-08-15 |
| DE602004008291T2 (de) | 2008-05-08 |
| AR045999A1 (es) | 2005-11-23 |
| DE602004008291D1 (de) | 2007-09-27 |
| EP1646620A1 (en) | 2006-04-19 |
| US20060247227A1 (en) | 2006-11-02 |
| TW200514781A (en) | 2005-05-01 |
| ATE370135T1 (de) | 2007-09-15 |
| JP2006528147A (ja) | 2006-12-14 |
| WO2005014571A1 (en) | 2005-02-17 |
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