DE602004008291T2 - Substituierte piperidine als histamin-h3-rezeptorliganden - Google Patents
Substituierte piperidine als histamin-h3-rezeptorliganden Download PDFInfo
- Publication number
- DE602004008291T2 DE602004008291T2 DE602004008291T DE602004008291T DE602004008291T2 DE 602004008291 T2 DE602004008291 T2 DE 602004008291T2 DE 602004008291 T DE602004008291 T DE 602004008291T DE 602004008291 T DE602004008291 T DE 602004008291T DE 602004008291 T2 DE602004008291 T2 DE 602004008291T2
- Authority
- DE
- Germany
- Prior art keywords
- piperidinyl
- oxy
- cyclobutyl
- methylethyl
- phenyl
- 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 - Fee Related
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- 102000004384 Histamine H3 receptors Human genes 0.000 title description 8
- 108090000981 Histamine H3 receptors Proteins 0.000 title description 8
- 150000003053 piperidines Chemical class 0.000 title description 3
- 239000003446 ligand Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 216
- -1 heterocyclyl radicals Chemical class 0.000 claims description 88
- 238000000034 method Methods 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 21
- 238000011282 treatment Methods 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 150000003254 radicals Chemical class 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 230000009467 reduction Effects 0.000 claims description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 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
- 229910005965 SO 2 Inorganic materials 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- UUYLVLYSXAEWAC-UHFFFAOYSA-N 3-tert-butyl-5-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]pyridine-2-carboxylic acid Chemical compound N1=C(C(O)=O)C(C(C)(C)C)=CC(N2CCC(CC2)OC2CCN(CC2)C2CCC2)=C1 UUYLVLYSXAEWAC-UHFFFAOYSA-N 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- AAZFNAXFFSBIIO-UHFFFAOYSA-N tert-butyl 5-[4-(1-propan-2-ylpiperidin-4-yl)oxypiperidin-1-yl]pyridine-2-carboxylate Chemical compound C1CN(C(C)C)CCC1OC1CCN(C=2C=NC(=CC=2)C(=O)OC(C)(C)C)CC1 AAZFNAXFFSBIIO-UHFFFAOYSA-N 0.000 claims description 8
- 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 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 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 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
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 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 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- 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
- 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 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
- 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 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
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 4
- 208000012902 Nervous system disease Diseases 0.000 claims description 4
- 208000025966 Neurological disease Diseases 0.000 claims description 4
- 125000003435 aroyl group Chemical group 0.000 claims description 4
- 125000005533 aryl carboxamido group Chemical group 0.000 claims description 4
- 125000005421 aryl sulfonamido group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 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 3
- 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
- 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 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
- 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 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-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
- 229910052757 nitrogen Inorganic materials 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
- 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
- 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
- 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
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- BUSOVOXDHSICQV-UHFFFAOYSA-N n-[4-[4-(1-cyclobutylpiperidin-4-yl)oxypiperidin-1-yl]-2-fluorophenyl]acetamide Chemical compound C1=C(F)C(NC(=O)C)=CC=C1N1CCC(OC2CCN(CC2)C2CCC2)CC1 BUSOVOXDHSICQV-UHFFFAOYSA-N 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
- 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
- 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
- IPUJOUZRKYPXEE-UHFFFAOYSA-N 5-[3-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(=CC(=CC=2)C=2ON=C(C)N=2)F)CC1 IPUJOUZRKYPXEE-UHFFFAOYSA-N 0.000 claims 1
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- KDHKSEPUCLOQCE-UHFFFAOYSA-N tert-butyl 4-(1-propan-2-ylpiperidin-4-yl)oxypiperidine-1-carboxylate Chemical compound C1CN(C(C)C)CCC1OC1CCN(C(=O)OC(C)(C)C)CC1 KDHKSEPUCLOQCE-UHFFFAOYSA-N 0.000 description 1
- HUTUONVUCLJWST-UHFFFAOYSA-M tert-butyl 4-(1-propan-2-ylpyridin-1-ium-4-yl)oxypiperidine-1-carboxylate;iodide Chemical compound [I-].C1=C[N+](C(C)C)=CC=C1OC1CCN(C(=O)OC(C)(C)C)CC1 HUTUONVUCLJWST-UHFFFAOYSA-M 0.000 description 1
- ADBROXSIUINEIC-UHFFFAOYSA-N tert-butyl 4-[1-(4-cyanophenyl)piperidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1CCN(C=2C=CC(=CC=2)C#N)CC1 ADBROXSIUINEIC-UHFFFAOYSA-N 0.000 description 1
- SGAWTMFFPGUVRV-UHFFFAOYSA-N tert-butyl 4-[1-(5-cyanopyridin-2-yl)piperidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1CCN(C=2N=CC(=CC=2)C#N)CC1 SGAWTMFFPGUVRV-UHFFFAOYSA-N 0.000 description 1
- OEQVTSSLMQEZSE-HNNXBMFYSA-N tert-butyl 4-[1-[(2s)-butan-2-yl]piperidin-4-yl]oxypiperidine-1-carboxylate Chemical compound C1CN([C@@H](C)CC)CCC1OC1CCN(C(=O)OC(C)(C)C)CC1 OEQVTSSLMQEZSE-HNNXBMFYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 239000003558 transferase inhibitor Substances 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 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
- C07D401/14—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
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
-
- 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
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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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- 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
- C07D211/36—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 Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Ophthalmology & Optometry (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0316893A GB0316893D0 (en) | 2003-07-18 | 2003-07-18 | Novel compounds |
| GB0316893 | 2003-07-18 | ||
| GB0411167 | 2004-05-19 | ||
| GB0411167A GB0411167D0 (en) | 2004-05-19 | 2004-05-19 | Novel compounds |
| PCT/EP2004/008061 WO2005014571A1 (en) | 2003-07-18 | 2004-07-16 | Substituted piperidines as histamine h3 receptor ligands |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE602004008291D1 DE602004008291D1 (de) | 2007-09-27 |
| DE602004008291T2 true DE602004008291T2 (de) | 2008-05-08 |
Family
ID=34137741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE602004008291T Expired - Fee Related DE602004008291T2 (de) | 2003-07-18 | 2004-07-16 | Substituierte piperidine als histamin-h3-rezeptorliganden |
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 |
| WO2007016496A2 (en) | 2005-08-02 | 2007-02-08 | Neurogen Corporation | Dipiperazinyl ketones and related analogues |
| WO2008145681A2 (en) | 2007-05-31 | 2008-12-04 | Boehringer Ingelheim International Gmbh | Ccr2 receptor antagonists and uses thereof |
| MX2010003398A (es) * | 2007-09-28 | 2010-04-09 | Schering Corp | Derivados de oxipiperidina como antagonistas del receptor de histamina. |
| CN102256963B (zh) | 2008-12-19 | 2014-06-11 | 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 |
| 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 |
| WO2011141477A1 (en) | 2010-05-12 | 2011-11-17 | Boehringer Ingelheim International Gmbh | New ccr2 receptor antagonists, method for producing the same, and use thereof as medicaments |
| JP5647339B2 (ja) | 2010-05-17 | 2014-12-24 | 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 | Ccr2アンタゴニスト及びこれらの使用 |
| 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 |
| WO2011147772A1 (en) | 2010-05-25 | 2011-12-01 | Boehringer Ingelheim International Gmbh | Ccr2 receptor antagonists |
| JP5721242B2 (ja) | 2010-06-01 | 2015-05-20 | 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アンタゴニスト |
| KR101764952B1 (ko) * | 2010-07-29 | 2017-08-03 | 리겔 파마슈티칼스, 인크. | Ampk-활성화 헤테로시클릭 화합물 및 그의 사용 방법 |
| EP2731941B1 (en) | 2011-07-15 | 2019-05-08 | Boehringer Ingelheim International GmbH | Novel and selective ccr2 antagonists |
| 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 |
| JP2015503598A (ja) * | 2012-01-16 | 2015-02-02 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドGlaxosmithkline Intellectual Property Development Limited | 治療的使用 |
| WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
| EP2647377A1 (en) | 2012-04-06 | 2013-10-09 | Sanofi | Use of an h3 receptor antagonist for the treatment of alzheimer's disease |
| EP3317270B1 (en) | 2015-07-02 | 2020-05-13 | Centrexion Therapeutics Corporation | (4-((3r,4r)-3-methoxytetrahydro-pyran-4-ylamino)piperidin-1-yl)(5-methyl-6-(((2r,6s)-6-(p-tolyl)tetrahydro-2h-pyran-2-yl)methylamino)pyrimidin-4yl)methanone citrate |
| US10752587B2 (en) | 2015-12-01 | 2020-08-25 | 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 |
| US6906081B2 (en) * | 2001-02-08 | 2005-06-14 | Schering Corporation | Use of dual H3/M2 antagonists in the treatment of cognition deficit disorders |
| EP2243776A1 (en) * | 2001-10-12 | 2010-10-27 | High Point Pharmaceuticals, LLC | Substituted piperidines and their use for the treatment of diseases related to the histamine H3 receptor |
| US7524852B2 (en) * | 2002-06-07 | 2009-04-28 | Kyowa Hakko Kogyo Co., Ltd. | Bicyclic pyrimidine derivatives |
-
2004
- 2004-07-16 US US10/564,931 patent/US20060247227A1/en not_active Abandoned
- 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 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 DE DE602004008291T patent/DE602004008291T2/de not_active Expired - Fee Related
- 2004-07-16 TW TW093121228A patent/TW200514781A/zh unknown
- 2004-07-16 AR ARP040102526A patent/AR045999A1/es unknown
- 2004-07-16 ES ES04763339T patent/ES2291913T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| TW200514781A (en) | 2005-05-01 |
| US20060247227A1 (en) | 2006-11-02 |
| EP1646620A1 (en) | 2006-04-19 |
| ES2291913T3 (es) | 2008-03-01 |
| WO2005014571A1 (en) | 2005-02-17 |
| JP2006528147A (ja) | 2006-12-14 |
| EP1646620B1 (en) | 2007-08-15 |
| DE602004008291D1 (de) | 2007-09-27 |
| ATE370135T1 (de) | 2007-09-15 |
| AR045999A1 (es) | 2005-11-23 |
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| 8381 | Inventor (new situation) |
Inventor name: HUXLEY, ANTHONY, HARLOW ESSEX CM19 5AW, GB Inventor name: BRUTON, GORDON, HARLOW ESSEX CM19 5AW, GB Inventor name: ORLEK, B. S., HARLOW ESSEX CM19 5AW, GB Inventor name: MILNER, PETER HENRY, HARLOW ESSEX CM19 5AW, GB Inventor name: BAILEY, J. M., HARLOW ESSEX CM19 5AW, GB |
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| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |