JP4553487B2 - ヒスタミンh3−受容体リガンドとしての非イミダゾールアルキルアミンと、その治療への応用。 - Google Patents
ヒスタミンh3−受容体リガンドとしての非イミダゾールアルキルアミンと、その治療への応用。 Download PDFInfo
- Publication number
- JP4553487B2 JP4553487B2 JP2000562103A JP2000562103A JP4553487B2 JP 4553487 B2 JP4553487 B2 JP 4553487B2 JP 2000562103 A JP2000562103 A JP 2000562103A JP 2000562103 A JP2000562103 A JP 2000562103A JP 4553487 B2 JP4553487 B2 JP 4553487B2
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- JP
- Japan
- Prior art keywords
- propyl
- group
- alkyl
- piperidine
- pyrrolidine
- 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
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- 239000003446 ligand Substances 0.000 title claims abstract description 14
- 102000004384 Histamine H3 receptors Human genes 0.000 title claims description 25
- 108090000981 Histamine H3 receptors Proteins 0.000 title claims description 25
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title abstract description 22
- 230000001225 therapeutic effect Effects 0.000 title description 4
- -1 imidazole alkylamine Chemical class 0.000 claims abstract description 213
- 239000003814 drug Substances 0.000 claims abstract description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 450
- 150000001875 compounds Chemical class 0.000 claims description 310
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 220
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 180
- 125000000217 alkyl group Chemical group 0.000 claims description 163
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 102
- 125000004432 carbon atom Chemical group C* 0.000 claims description 98
- 125000003118 aryl group Chemical group 0.000 claims description 75
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 51
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 43
- 125000001424 substituent group Chemical group 0.000 claims description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 229910052717 sulfur Chemical group 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 239000000556 agonist Substances 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000004434 sulfur atom Chemical group 0.000 claims description 17
- 125000002837 carbocyclic group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 239000005557 antagonist Substances 0.000 claims description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000002619 bicyclic group Chemical group 0.000 claims description 12
- 125000000468 ketone group Chemical group 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 150000004677 hydrates Chemical class 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000001336 alkenes Chemical class 0.000 claims description 10
- 150000001299 aldehydes Chemical class 0.000 claims description 9
- 125000003435 aroyl group Chemical group 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 150000002576 ketones Chemical class 0.000 claims description 9
- 230000003287 optical effect Effects 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 239000004031 partial agonist Substances 0.000 claims description 7
- 125000005936 piperidyl group Chemical group 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 150000001345 alkine derivatives Chemical class 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000001589 carboacyl group Chemical group 0.000 claims description 5
- 125000003544 oxime group Chemical group 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- BTOMYKSORLKZMU-UHFFFAOYSA-N C(C)C1=CC=C(OCCCN2CCCCC2)C=C1.C(CC)C1=CC=C(OCCCN2CCCCC2)C=C1.C(C)(CC)C1=CC=C(OCCCN2CCCCC2)C=C1.C(C)(C)C1=CC=C(OCCCN2CCCCC2)C=C1.N1CCCCC1 Chemical compound C(C)C1=CC=C(OCCCN2CCCCC2)C=C1.C(CC)C1=CC=C(OCCCN2CCCCC2)C=C1.C(C)(CC)C1=CC=C(OCCCN2CCCCC2)C=C1.C(C)(C)C1=CC=C(OCCCN2CCCCC2)C=C1.N1CCCCC1 BTOMYKSORLKZMU-UHFFFAOYSA-N 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
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- NNACHAUCXXVJSP-UHFFFAOYSA-N pitolisant Chemical compound C1=CC(Cl)=CC=C1CCCOCCCN1CCCCC1 NNACHAUCXXVJSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 4
- 150000003457 sulfones Chemical class 0.000 claims description 4
- ZTYVJNYCCVFJGR-UHFFFAOYSA-N 1-[3-(3,3-dimethylbutoxy)propyl]piperidine Chemical compound CC(C)(C)CCOCCCN1CCCCC1 ZTYVJNYCCVFJGR-UHFFFAOYSA-N 0.000 claims description 3
- ZBYDMLXPLCXXGZ-UHFFFAOYSA-N 1-[3-(3-phenylpropoxy)propyl]pyrrolidine Chemical compound C1CCCN1CCCOCCCC1=CC=CC=C1 ZBYDMLXPLCXXGZ-UHFFFAOYSA-N 0.000 claims description 3
- SHDCMHVGBWJCOB-UHFFFAOYSA-N 1-[5-(4-phenylphenoxy)pentyl]pyrrolidine Chemical compound C1CCCN1CCCCCOC(C=C1)=CC=C1C1=CC=CC=C1 SHDCMHVGBWJCOB-UHFFFAOYSA-N 0.000 claims description 3
- ARXUNWQEEIWRFV-UHFFFAOYSA-N 1-[6-phenyl-1-(6-phenyl-3-piperidin-1-ylhexoxy)hexan-3-yl]piperidine Chemical compound C=1C=CC=CC=1CCCC(N1CCCCC1)CCOCCC(N1CCCCC1)CCCC1=CC=CC=C1 ARXUNWQEEIWRFV-UHFFFAOYSA-N 0.000 claims description 3
- VZGBGKHEMQIUPH-UHFFFAOYSA-N 2-(3-piperidin-1-ylpropoxy)-1,3-benzothiazole Chemical compound N=1C2=CC=CC=C2SC=1OCCCN1CCCCC1 VZGBGKHEMQIUPH-UHFFFAOYSA-N 0.000 claims description 3
- BJHRYRUSBLZQIB-UMNHINIKSA-N C(#N)C1=CC=C(OCCCN2[C@H](CC[C@@H](C2)CC)C)C=C1.C(#N)C1=CC=C(OCCCN2[C@H](CC[C@H](C2)CC)C)C=C1.C1(CCCC1)C(=O)C1=CC=C(OCCCN2CCCCC2)C=C1 Chemical compound C(#N)C1=CC=C(OCCCN2[C@H](CC[C@@H](C2)CC)C)C=C1.C(#N)C1=CC=C(OCCCN2[C@H](CC[C@H](C2)CC)C)C=C1.C1(CCCC1)C(=O)C1=CC=C(OCCCN2CCCCC2)C=C1 BJHRYRUSBLZQIB-UMNHINIKSA-N 0.000 claims description 3
- KCHIGZSQXJTXKL-RLGPXSRBSA-N C1(CC1)C(=O)C1=CC=C(OCCCN2C[C@H](C[C@@H](C2)C)C)C=C1.C(#N)C1=CC=C(OCCCN2C[C@H](C[C@@H](C2)C)C)C=C1 Chemical compound C1(CC1)C(=O)C1=CC=C(OCCCN2C[C@H](C[C@@H](C2)C)C)C=C1.C(#N)C1=CC=C(OCCCN2C[C@H](C[C@@H](C2)C)C)C=C1 KCHIGZSQXJTXKL-RLGPXSRBSA-N 0.000 claims description 3
- XECQIHAUZSJKSI-UHFFFAOYSA-N CN(CCCCCOC1=CC=CC=C1)CC.O(C1=CC=CC=C1)CCCCCN1CCCC1.O(C1=CC=CC=C1)CCCCCN1CCCCC1 Chemical compound CN(CCCCCOC1=CC=CC=C1)CC.O(C1=CC=CC=C1)CCCCCN1CCCC1.O(C1=CC=CC=C1)CCCCCN1CCCCC1 XECQIHAUZSJKSI-UHFFFAOYSA-N 0.000 claims description 3
- PKYDOJAWVJSQEI-UHFFFAOYSA-N OC(CC)C1=CC=C(OCCCN2CCC(CC2)C)C=C1.OC(CC)C1=CC=C(OCCCN2CC(CCC2)C)C=C1.C(CC)(=O)C1=CC=C(OCCCN2C(CCCC2)C)C=C1 Chemical compound OC(CC)C1=CC=C(OCCCN2CCC(CC2)C)C=C1.OC(CC)C1=CC=C(OCCCN2CC(CCC2)C)C=C1.C(CC)(=O)C1=CC=C(OCCCN2C(CCCC2)C)C=C1 PKYDOJAWVJSQEI-UHFFFAOYSA-N 0.000 claims description 3
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 3
- 239000012965 benzophenone Substances 0.000 claims description 3
- 150000008366 benzophenones Chemical class 0.000 claims description 3
- 230000007278 cognition impairment Effects 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
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- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 206010022437 insomnia Diseases 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 3
- ZXIQZCPJDICLNA-UHFFFAOYSA-N 1-(5-phenoxypentyl)-2,5-dihydropyrrole;1-[5-(3-phenylphenoxy)pentyl]pyrrolidine Chemical compound C1C=CCN1CCCCCOC1=CC=CC=C1.C1CCCN1CCCCCOC(C=1)=CC=CC=1C1=CC=CC=C1 ZXIQZCPJDICLNA-UHFFFAOYSA-N 0.000 claims description 2
- QSHSUPUUQNVVTB-UHFFFAOYSA-N 1-[4-(5-pyrrolidin-1-ylpentoxy)phenyl]ethanol Chemical compound C1=CC(C(O)C)=CC=C1OCCCCCN1CCCC1 QSHSUPUUQNVVTB-UHFFFAOYSA-N 0.000 claims description 2
- AFLNEOSXJRFKJB-UHFFFAOYSA-N 1-[4-[3-(4-methylpiperidin-1-yl)propoxy]phenyl]propan-1-one Chemical compound C1=CC(C(=O)CC)=CC=C1OCCCN1CCC(C)CC1 AFLNEOSXJRFKJB-UHFFFAOYSA-N 0.000 claims description 2
- GCINBWWQZPLPMO-UHFFFAOYSA-N 2-(cyclohexylmethyl)-1-(3-piperidin-1-ylpropyl)guanidine;1-[3-(diethylamino)propyl]-3-phenylurea Chemical compound CCN(CC)CCCNC(=O)NC1=CC=CC=C1.C1CCCCC1CN=C(N)NCCCN1CCCCC1 GCINBWWQZPLPMO-UHFFFAOYSA-N 0.000 claims description 2
- DKPZVUAFSFRTQZ-UHFFFAOYSA-N 4-[3-(3-methylpiperidin-1-yl)propoxy]benzonitrile Chemical compound C1C(C)CCCN1CCCOC1=CC=C(C#N)C=C1 DKPZVUAFSFRTQZ-UHFFFAOYSA-N 0.000 claims description 2
- PFHGPNGSWIHVIR-XAEMHTEYSA-N 4-[3-[(3r,5s)-3,5-dimethylpiperidin-1-yl]propoxy]benzonitrile;1-[4-[3-(2-methylpiperidin-1-yl)propoxy]phenyl]propan-1-one;1-[4-[3-(4-methylpiperidin-1-yl)propoxy]phenyl]propan-1-one Chemical compound C1[C@@H](C)C[C@@H](C)CN1CCCOC1=CC=C(C#N)C=C1.C1=CC(C(=O)CC)=CC=C1OCCCN1CCC(C)CC1.C1=CC(C(=O)CC)=CC=C1OCCCN1C(C)CCCC1 PFHGPNGSWIHVIR-XAEMHTEYSA-N 0.000 claims description 2
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- SIYQBUGIHQHGBU-UHFFFAOYSA-N O(C1=CC=CC=C1)CCCN1CCCC1.C1(=CC=CC=C1)SCCCCN1CCCC1.C1(=CC=CC=C1)SCCCCCN1CCCC1.O(C1=CC=CC=C1)CCCCCCN1CCCC1.O(C1=CC=CC=C1)CCCCN1CCCC1 Chemical compound O(C1=CC=CC=C1)CCCN1CCCC1.C1(=CC=CC=C1)SCCCCN1CCCC1.C1(=CC=CC=C1)SCCCCCN1CCCC1.O(C1=CC=CC=C1)CCCCCCN1CCCC1.O(C1=CC=CC=C1)CCCCN1CCCC1 SIYQBUGIHQHGBU-UHFFFAOYSA-N 0.000 claims description 2
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 6
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- UZDCKZLKZIERDJ-UHFFFAOYSA-N 1-[5-(4-chlorophenoxy)pentyl]pyrrolidine;1-[5-(4-methoxyphenoxy)pentyl]pyrrolidine Chemical compound C1=CC(Cl)=CC=C1OCCCCCN1CCCC1.C1=CC(OC)=CC=C1OCCCCCN1CCCC1 UZDCKZLKZIERDJ-UHFFFAOYSA-N 0.000 claims 1
- ITOJPDNONZGUKB-UHFFFAOYSA-N 1-[5-(4-nitrophenoxy)pentyl]pyrrolidine Chemical compound C1=CC([N+](=O)[O-])=CC=C1OCCCCCN1CCCC1 ITOJPDNONZGUKB-UHFFFAOYSA-N 0.000 claims 1
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- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
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- 239000001433 sodium tartrate Substances 0.000 description 1
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- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
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- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
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- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
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- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98401944.8 | 1998-07-29 | ||
| EP98401944A EP0978512A1 (en) | 1998-07-29 | 1998-07-29 | Non-imidazole aryloxy (or arylthio) alkylamines as histamine H3-receptor antagonists and their therapeutic applications |
| EP98403351.4 | 1998-12-31 | ||
| EP98403351A EP0982300A3 (en) | 1998-07-29 | 1998-12-31 | Non-imidazole alkylamines as histamine H3 - receptor ligands and their therapeutic applications |
| PCT/EP1999/005744 WO2000006254A2 (en) | 1998-07-29 | 1999-07-29 | Non-imidazole alkylamines as histamine h3-receptor ligands and their therapeutic applications |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2010127067A Division JP5301501B2 (ja) | 1998-07-29 | 2010-06-02 | ヒスタミンh3−受容体リガンドとしての非イミダゾールアルキルアミンと、その治療への応用 |
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| JP2002521463A JP2002521463A (ja) | 2002-07-16 |
| JP2002521463A5 JP2002521463A5 (https=) | 2006-12-07 |
| JP4553487B2 true JP4553487B2 (ja) | 2010-09-29 |
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| JP2010127067A Expired - Lifetime JP5301501B2 (ja) | 1998-07-29 | 2010-06-02 | ヒスタミンh3−受容体リガンドとしての非イミダゾールアルキルアミンと、その治療への応用 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2010127067A Expired - Lifetime JP5301501B2 (ja) | 1998-07-29 | 2010-06-02 | ヒスタミンh3−受容体リガンドとしての非イミダゾールアルキルアミンと、その治療への応用 |
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| EP (4) | EP0982300A3 (https=) |
| JP (2) | JP4553487B2 (https=) |
| AT (2) | ATE276751T1 (https=) |
| AU (1) | AU5511999A (https=) |
| BE (1) | BE2016C048I2 (https=) |
| CA (1) | CA2321881C (https=) |
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| ES (2) | ES2226423T3 (https=) |
| FR (1) | FR16C0038I2 (https=) |
| LU (1) | LU93229I2 (https=) |
| PT (2) | PT1428820E (https=) |
| WO (1) | WO2000006254A2 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010189441A (ja) * | 1998-07-29 | 2010-09-02 | Soc Civile Bioprojet | ヒスタミンh3−受容体リガンドとしての非イミダゾールアルキルアミンと、その治療への応用 |
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| US3312696A (en) * | 1964-02-20 | 1967-04-04 | Turbanti Luigi | 2-tertiary amino alkoxy-betaphenyl-propiophenones |
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| DE2408530A1 (de) * | 1974-02-22 | 1975-09-04 | Basf Ag | Verfahren zur herstellung von betahalogenalkylaminosulfonylhalogeniden |
| GB1513092A (en) * | 1975-06-05 | 1978-06-07 | Bottu | O-aminophenol derivatives |
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| EP0090972B1 (en) * | 1982-03-17 | 1990-05-30 | Asahi Kasei Kogyo Kabushiki Kaisha | Indazole derivatives |
| DK368687A (da) * | 1986-11-21 | 1988-05-22 | Cheminova As | Aminoalkylerede hydroxyforbindelser og deres anvendelse som fungicider |
| US5348964A (en) * | 1990-07-25 | 1994-09-20 | Merrell Dow Pharmaceuticals Inc. | Piperidyl ethers and thioethers as inhibitors of cholesterol biosynthesis |
| EP0982300A3 (en) * | 1998-07-29 | 2000-03-08 | Societe Civile Bioprojet | Non-imidazole alkylamines as histamine H3 - receptor ligands and their therapeutic applications |
| FR2788775B1 (fr) * | 1999-01-22 | 2001-04-13 | Pf Medicament | Nouvelles n-alcoyl-n-[1-(omega-(arylalcoyloxy)alcoyl] piperidin-4-yl]-4h-3,1-benzo(thia/oxa)zines-2-amines substituees, leur preparation et leur application en therapeutique |
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1998
- 1998-12-31 EP EP98403351A patent/EP0982300A3/en not_active Withdrawn
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1999
- 1999-07-29 CA CA2321881A patent/CA2321881C/en not_active Expired - Lifetime
- 1999-07-29 EP EP99941543A patent/EP1100503B1/en not_active Expired - Lifetime
- 1999-07-29 EP EP06002726A patent/EP2000462A3/en not_active Withdrawn
- 1999-07-29 PT PT04003944T patent/PT1428820E/pt unknown
- 1999-07-29 AU AU55119/99A patent/AU5511999A/en not_active Abandoned
- 1999-07-29 PT PT99941543T patent/PT1100503E/pt unknown
- 1999-07-29 ES ES99941543T patent/ES2226423T3/es not_active Expired - Lifetime
- 1999-07-29 DE DE69931409T patent/DE69931409T2/de not_active Expired - Lifetime
- 1999-07-29 DE DE69920472T patent/DE69920472T2/de not_active Expired - Lifetime
- 1999-07-29 JP JP2000562103A patent/JP4553487B2/ja not_active Expired - Lifetime
- 1999-07-29 ES ES04003944T patent/ES2260703T3/es not_active Expired - Lifetime
- 1999-07-29 US US09/622,199 patent/US7138413B1/en not_active Expired - Lifetime
- 1999-07-29 AT AT99941543T patent/ATE276751T1/de active
- 1999-07-29 AT AT04003944T patent/ATE326446T1/de active
- 1999-07-29 EP EP04003944A patent/EP1428820B1/en not_active Expired - Lifetime
- 1999-07-29 DK DK04003944T patent/DK1428820T3/da active
- 1999-07-29 WO PCT/EP1999/005744 patent/WO2000006254A2/en not_active Ceased
- 1999-07-29 DK DK99941543T patent/DK1100503T3/da active
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2004
- 2004-06-01 US US10/856,838 patent/US7169928B2/en not_active Expired - Lifetime
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2006
- 2006-07-03 US US11/478,682 patent/US7910605B2/en not_active Expired - Fee Related
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2010
- 2010-06-02 JP JP2010127067A patent/JP5301501B2/ja not_active Expired - Lifetime
- 2010-12-15 US US12/968,807 patent/US20110281844A1/en not_active Abandoned
-
2016
- 2016-09-21 LU LU93229C patent/LU93229I2/fr unknown
- 2016-09-23 BE BE2016C048C patent/BE2016C048I2/fr unknown
- 2016-09-26 FR FR16C0038C patent/FR16C0038I2/fr active Active
- 2016-09-28 CY CY2016032C patent/CY2016032I2/el unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010189441A (ja) * | 1998-07-29 | 2010-09-02 | Soc Civile Bioprojet | ヒスタミンh3−受容体リガンドとしての非イミダゾールアルキルアミンと、その治療への応用 |
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