JP4612990B2 - ヒスタミン−3受容体リガンドとしての新規アミンおよびそれらの治療的適用 - Google Patents
ヒスタミン−3受容体リガンドとしての新規アミンおよびそれらの治療的適用 Download PDFInfo
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- JP4612990B2 JP4612990B2 JP2002573767A JP2002573767A JP4612990B2 JP 4612990 B2 JP4612990 B2 JP 4612990B2 JP 2002573767 A JP2002573767 A JP 2002573767A JP 2002573767 A JP2002573767 A JP 2002573767A JP 4612990 B2 JP4612990 B2 JP 4612990B2
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- Prior art keywords
- ethyl
- benzofuran
- methyl
- pyrrolidinyl
- pyrrolidin
- 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.)
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- 150000001412 amines Chemical class 0.000 title description 10
- 239000003446 ligand Substances 0.000 title description 7
- 230000001225 therapeutic effect Effects 0.000 title 1
- -1 (2R) -2-methyl-1-pyrrolidinyl Chemical group 0.000 claims description 1117
- 150000001875 compounds Chemical class 0.000 claims description 445
- 125000000217 alkyl group Chemical group 0.000 claims description 171
- 229910052739 hydrogen Inorganic materials 0.000 claims description 144
- 239000001257 hydrogen Substances 0.000 claims description 144
- 125000000623 heterocyclic group Chemical group 0.000 claims description 143
- 229910052757 nitrogen Inorganic materials 0.000 claims description 108
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 106
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 91
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 88
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 76
- 150000002431 hydrogen Chemical class 0.000 claims description 76
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 68
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 68
- 125000003545 alkoxy group Chemical group 0.000 claims description 61
- 229910052736 halogen Inorganic materials 0.000 claims description 58
- 150000002367 halogens Chemical class 0.000 claims description 58
- 125000001188 haloalkyl group Chemical group 0.000 claims description 57
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 56
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 55
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 55
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 53
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 50
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 50
- 125000004414 alkyl thio group Chemical group 0.000 claims description 46
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 43
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 43
- 125000004076 pyridyl group Chemical group 0.000 claims description 43
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 43
- 125000002757 morpholinyl group Chemical group 0.000 claims description 41
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 40
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 40
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 40
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 39
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 39
- 125000004193 piperazinyl group Chemical group 0.000 claims description 39
- 125000003386 piperidinyl group Chemical group 0.000 claims description 39
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 39
- 125000002393 azetidinyl group Chemical group 0.000 claims description 38
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 38
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 38
- 125000003725 azepanyl group Chemical group 0.000 claims description 35
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 31
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 28
- 125000002947 alkylene group Chemical group 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 14
- 229910052727 yttrium Inorganic materials 0.000 claims description 13
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 12
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
- 125000004450 alkenylene group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- KFHYZKCRXNRKRC-MRXNPFEDSA-N abt-239 Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 KFHYZKCRXNRKRC-MRXNPFEDSA-N 0.000 claims description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
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- AZWATKGVDUSMSO-MRXNPFEDSA-N 1-[3-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]phenyl]ethanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(C=CC=3)C(C)=O)=CC=C2O1 AZWATKGVDUSMSO-MRXNPFEDSA-N 0.000 claims description 5
- KPNUCNMZTCZSCQ-CYBMUJFWSA-N 3,5-dimethyl-4-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-1,2-oxazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C3=C(ON=C3C)C)=CC=C2O1 KPNUCNMZTCZSCQ-CYBMUJFWSA-N 0.000 claims description 5
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- MLKLMMHXAFOMLR-UJONTBEJSA-N 4-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2,3-dihydro-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1OC2=CC=C(C=3C=CC(=CC=3)C#N)C=C2C1 MLKLMMHXAFOMLR-UJONTBEJSA-N 0.000 claims description 5
- OYUBXZVOQPBECQ-QGZVFWFLSA-N (2r)-1-[2-(5-benzyl-1-benzofuran-2-yl)ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(CC=3C=CC=CC=3)=CC=C2O1 OYUBXZVOQPBECQ-QGZVFWFLSA-N 0.000 claims description 4
- LCWMVSMZFNKPMC-OAHLLOKOSA-N (2r)-1-[2-[5-(4-fluorophenyl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(F)=CC=3)=CC=C2O1 LCWMVSMZFNKPMC-OAHLLOKOSA-N 0.000 claims description 4
- QQVDGSPBKSWRPI-QGZVFWFLSA-N (2r)-2-methyl-1-[2-[5-(2-methylphenyl)-1-benzofuran-2-yl]ethyl]pyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C(=CC=CC=3)C)=CC=C2O1 QQVDGSPBKSWRPI-QGZVFWFLSA-N 0.000 claims description 4
- ARRAWZMFGXGZJA-OAHLLOKOSA-N (3-chlorophenyl)-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C(=O)C=3C=C(Cl)C=CC=3)=CC=C2O1 ARRAWZMFGXGZJA-OAHLLOKOSA-N 0.000 claims description 4
- OKOPCYYMBGBJLQ-OAHLLOKOSA-N (3-fluorophenyl)-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C(=O)C=3C=C(F)C=CC=3)=CC=C2O1 OKOPCYYMBGBJLQ-OAHLLOKOSA-N 0.000 claims description 4
- OAGQKGSJQMWGBI-LJQANCHMSA-N (3-fluorophenyl)-[3-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]phenyl]methanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(C=CC=3)C(=O)C=3C=C(F)C=CC=3)=CC=C2O1 OAGQKGSJQMWGBI-LJQANCHMSA-N 0.000 claims description 4
- VGSYEFOBFMUWGO-OAHLLOKOSA-N (4-fluorophenyl)-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C(=O)C=3C=CC(F)=CC=3)=CC=C2O1 VGSYEFOBFMUWGO-OAHLLOKOSA-N 0.000 claims description 4
- WPPQUNPJCSHTHG-OAHLLOKOSA-N 2-fluoro-4-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(F)C(C#N)=CC=3)=CC=C2O1 WPPQUNPJCSHTHG-OAHLLOKOSA-N 0.000 claims description 4
- PUYLRAJUSRKGNY-OAHLLOKOSA-N 3-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-5-(thiophen-2-ylmethyl)-1,2,4-oxadiazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3N=C(CC=4SC=CC=4)ON=3)=CC=C2O1 PUYLRAJUSRKGNY-OAHLLOKOSA-N 0.000 claims description 4
- WWEXCCZITRBBJR-MRXNPFEDSA-N 3-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(C=CC=3)C#N)=CC=C2O1 WWEXCCZITRBBJR-MRXNPFEDSA-N 0.000 claims description 4
- NSWXSLGPNBDJSG-MRXNPFEDSA-N 3-ethyl-1-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]pentan-1-one Chemical compound C=1C2=CC(C(=O)CC(CC)CC)=CC=C2OC=1CCN1CCC[C@H]1C NSWXSLGPNBDJSG-MRXNPFEDSA-N 0.000 claims description 4
- PJIVVAJXWKUQRT-QGZVFWFLSA-N 3-methyl-4-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C(=CC(=CC=3)C#N)C)=CC=C2O1 PJIVVAJXWKUQRT-QGZVFWFLSA-N 0.000 claims description 4
- LTKBEKWYXONRLE-MRXNPFEDSA-N 4-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-4-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=C(C=3C=CC(=CC=3)C#N)C=CC=C2O1 LTKBEKWYXONRLE-MRXNPFEDSA-N 0.000 claims description 4
- RYMGYDNLRZISML-FQEVSTJZSA-N 4-[2-[2-[(2s)-2-(fluoromethyl)pyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound FC[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 RYMGYDNLRZISML-FQEVSTJZSA-N 0.000 claims description 4
- SUXVYLBRHCOYGN-IRXDYDNUSA-N 4-[2-[2-[(2s,5s)-2,5-dimethylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@H]1CC[C@H](C)N1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 SUXVYLBRHCOYGN-IRXDYDNUSA-N 0.000 claims description 4
- FXGAPEOCLPYRLZ-QGZVFWFLSA-N 4-[6-methyl-2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=C(C)C=C2O1 FXGAPEOCLPYRLZ-QGZVFWFLSA-N 0.000 claims description 4
- BYXKUYQJFGQCAP-OAHLLOKOSA-N 4-[7-fluoro-2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC(F)=C2O1 BYXKUYQJFGQCAP-OAHLLOKOSA-N 0.000 claims description 4
- UCACSHIPFQVVQO-QGZVFWFLSA-N 4-[7-methyl-2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC(C)=C2O1 UCACSHIPFQVVQO-QGZVFWFLSA-N 0.000 claims description 4
- NBGOTRKECBBASK-UHFFFAOYSA-N [4-[2-[2-(2-methylpyrrolidin-1-yl)ethyl]-1-benzofuran-5-yl]phenyl]-morpholin-4-ylmethanone Chemical compound CC1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C(=O)N3CCOCC3)=CC=C2O1 NBGOTRKECBBASK-UHFFFAOYSA-N 0.000 claims description 4
- RRLCACGGDHPKNQ-UHFFFAOYSA-N morpholin-4-yl-[6-[2-(2-pyrrolidin-1-ylethyl)-1-benzofuran-5-yl]pyridin-3-yl]methanone Chemical compound C=1C=C(C=2C=C3C=C(CCN4CCCC4)OC3=CC=2)N=CC=1C(=O)N1CCOCC1 RRLCACGGDHPKNQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
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- BCDZCOWNIXKIFN-MRXNPFEDSA-N (2-methoxyphenyl)-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound COC1=CC=CC=C1C(=O)C1=CC=C(OC(CCN2[C@@H](CCC2)C)=C2)C2=C1 BCDZCOWNIXKIFN-MRXNPFEDSA-N 0.000 claims description 3
- JSFFTMNTWAMSKS-CQSZACIVSA-N (3,5-difluorophenyl)-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C(=O)C=3C=C(F)C=C(F)C=3)=CC=C2O1 JSFFTMNTWAMSKS-CQSZACIVSA-N 0.000 claims description 3
- ZCQGCYSLQDBETN-MRXNPFEDSA-N (3-methoxyphenyl)-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound COC1=CC=CC(C(=O)C=2C=C3C=C(CCN4[C@@H](CCC4)C)OC3=CC=2)=C1 ZCQGCYSLQDBETN-MRXNPFEDSA-N 0.000 claims description 3
- PWRBPHUOIIYBHI-MRXNPFEDSA-N (4-chloro-3-methylphenyl)-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C(=O)C=3C=C(C)C(Cl)=CC=3)=CC=C2O1 PWRBPHUOIIYBHI-MRXNPFEDSA-N 0.000 claims description 3
- LSJFPFPCUYVELQ-MRXNPFEDSA-N (4-fluoro-3-methylphenyl)-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C(=O)C=3C=C(C)C(F)=CC=3)=CC=C2O1 LSJFPFPCUYVELQ-MRXNPFEDSA-N 0.000 claims description 3
- YANFQSPNBDHUOP-QGZVFWFLSA-N (4-methylphenyl)-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C(=O)C=3C=CC(C)=CC=3)=CC=C2O1 YANFQSPNBDHUOP-QGZVFWFLSA-N 0.000 claims description 3
- GEGFJMYOFOIEEZ-CQSZACIVSA-N 1-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]imidazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(N3C=NC=C3)=CC=C2O1 GEGFJMYOFOIEEZ-CQSZACIVSA-N 0.000 claims description 3
- DMJYWUDBYVJYJG-TZHYSIJRSA-N 1-[3-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]phenyl]ethanol Chemical compound CC(O)C1=CC=CC(C=2C=C3C=C(CCN4[C@@H](CCC4)C)OC3=CC=2)=C1 DMJYWUDBYVJYJG-TZHYSIJRSA-N 0.000 claims description 3
- CIPPJHOVCBGSOP-QGZVFWFLSA-N 2-[3-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]phenyl]propan-2-ol Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(C=CC=3)C(C)(C)O)=CC=C2O1 CIPPJHOVCBGSOP-QGZVFWFLSA-N 0.000 claims description 3
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- HNCVRGCNKZVUSU-VIFPVBQESA-N tert-butyl (2s)-2-(methylsulfonyloxymethyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1COS(C)(=O)=O HNCVRGCNKZVUSU-VIFPVBQESA-N 0.000 description 1
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- 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
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Classifications
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| US10/081,207 US6969730B2 (en) | 2001-03-16 | 2002-02-25 | Amines as histamine-3 receptor ligands and their therapeutic applications |
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| US6822101B2 (en) | 2002-09-16 | 2004-11-23 | Abbott Laboratories | Process for preparing amine-substituted benzofurans |
| US7153889B2 (en) | 2002-11-12 | 2006-12-26 | Abbott Laboratories | Bicyclic-substituted amines as histamine-3 receptor ligands |
| WO2004043458A1 (en) * | 2002-11-12 | 2004-05-27 | Abbott Laboratories | Bicyclic-substituted amines as histamine-3 receptor ligands |
| US7244852B2 (en) | 2003-02-27 | 2007-07-17 | Abbott Laboratories | Process for preparing 2-methylpyrrolidine and specific enantiomers thereof |
| JP4736043B2 (ja) | 2003-03-14 | 2011-07-27 | 小野薬品工業株式会社 | 含窒素複素環誘導体およびそれらを有効成分とする薬剤 |
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| US7094790B2 (en) | 2003-05-07 | 2006-08-22 | Abbott Laboratories | Fused bicyclic-substituted amines as histamine-3 receptor ligands |
| EP1620434B1 (en) * | 2003-05-07 | 2011-03-09 | Abbott Laboratories | Fused bicyclic-substituted amines as histamine-3 receptor ligands |
| US20040224952A1 (en) * | 2003-05-07 | 2004-11-11 | Cowart Marlon D. | Fused bicyclic-substituted amines as histamine-3 receptor ligands |
| EP1723126A2 (en) * | 2003-10-22 | 2006-11-22 | Eli Lilly And Company | Novel mch receptor antagonists |
| US7435837B2 (en) | 2003-10-24 | 2008-10-14 | Wyeth | Dihydrobenzofuranyl alkanamine derivatives and methods for using same |
| SE0303480D0 (sv) * | 2003-12-19 | 2003-12-19 | Biovitrum Ab | Benzofuranes |
| WO2005085214A1 (ja) * | 2004-03-05 | 2005-09-15 | Banyu Pharmaceutical Co., Ltd | ジアリール置換複素5員環誘導体 |
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| US7098222B2 (en) | 2004-05-12 | 2006-08-29 | Abbott Laboratories | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
| US7205316B2 (en) | 2004-05-12 | 2007-04-17 | Abbott Laboratories | Tri- and bi-cyclic heteroaryl histamine-3 receptor ligands |
| US7145005B2 (en) | 2004-05-12 | 2006-12-05 | Abbott Laboratories | 2-(6-{2-[(2R)-2-Methyl-1-pyrrolidin-1-yl]-ethyl}-2-naphthalen-2-yl)-2H-pyridazin-3-one salts and their preparation |
| US20050256118A1 (en) * | 2004-05-12 | 2005-11-17 | Altenbach Robert J | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
| US20050256309A1 (en) * | 2004-05-12 | 2005-11-17 | Altenbach Robert J | Tri-and bi-cyclic heteroaryl histamine-3 receptor ligands |
| DE102004030099A1 (de) * | 2004-06-22 | 2006-01-12 | Grünenthal GmbH | Gesättigte und ungesättigte 3-Pyridyl-benzocycloalkylmethyl-amine als Serotonin- und/oder Noradrenalin-Reuptake-Hemmer und/oder µ-Opioidrezeptor-Modulatoren |
| AU2005283326B2 (en) | 2004-09-13 | 2011-07-21 | Ono Pharmaceutical Co., Ltd. | Nitrogenous heterocyclic derivative and medicine containing the same as an active ingredient |
| ATE530519T1 (de) * | 2005-06-03 | 2011-11-15 | Abbott Lab | Cyclobutylaminderivate |
| CA2644368A1 (en) | 2006-03-10 | 2007-09-20 | Ono Pharmaceutical Co., Ltd. | Nitrogenated heterocyclic derivative, and pharmaceutical agent comprising the derivative as active ingredient |
| WO2007149395A2 (en) * | 2006-06-20 | 2007-12-27 | Amphora Discovery Corporation | 2,5-substituted oxazole derivatives as protein kinase inhibitors for the treatment of cancer |
| US9108948B2 (en) | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
| KR20090024811A (ko) | 2006-06-23 | 2009-03-09 | 아보트 러보러터리즈 | 히스타민 h3 수용체 조절제로서의 사이클로프로필 아민 유도체 |
| CA2705502C (en) * | 2007-11-13 | 2016-01-26 | Taisho Pharmaceutical Co., Ltd. | Phenylpyrazole derivatives |
| US8383657B2 (en) | 2007-12-21 | 2013-02-26 | Abbott Laboratories | Thiazolylidine urea and amide derivatives and methods of use thereof |
| AU2009304596A1 (en) | 2008-10-17 | 2010-04-22 | Akaal Pharma Pty Ltd | S1P receptors modulators |
| CA2740484C (en) * | 2008-10-17 | 2021-09-21 | Akaal Pharma Pty Ltd | S1p receptors modulators and their use thereof |
| US9186353B2 (en) | 2009-04-27 | 2015-11-17 | Abbvie Inc. | Treatment of osteoarthritis pain |
| JP2012082186A (ja) * | 2010-09-15 | 2012-04-26 | Bayer Cropscience Ag | 殺虫性アリールピロリジン類 |
| GB201113538D0 (en) * | 2011-08-04 | 2011-09-21 | Karobio Ab | Novel estrogen receptor ligands |
| ES2647965T3 (es) * | 2013-01-09 | 2017-12-27 | Arena Pharmaceuticals, Inc. | Derivados de bifenil-etil-pirrolidina como moduladores del receptor de histamina H3 para el tratamiento de trastornos cognitivos |
| EP3236964A4 (en) * | 2014-12-22 | 2018-09-19 | Teva Pharmaceuticals International GmbH | L-tartrate salt of pridopidine |
| CN109456292B (zh) * | 2018-10-23 | 2022-06-10 | 中山大学 | 一种海洋真菌来源的香豆素类化合物及其制备方法与应用 |
| WO2022113008A1 (en) | 2020-11-27 | 2022-06-02 | Richter Gedeon Nyrt. | Histamine h3 receptor antagonists/inverse agonists for the treatment of autism spectrum disorder |
| CN114805261B (zh) * | 2021-01-18 | 2023-03-21 | 沈阳药科大学 | 苯并呋喃类lsd1抑制剂及其制备方法 |
| CN115385885A (zh) * | 2022-05-05 | 2022-11-25 | 深圳海创生物科技有限公司 | 一种蓝莓多酚、组合物及其在制备具有降血脂和/或减肥作用的药物或食品中的应用 |
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| US4237144A (en) * | 1979-06-21 | 1980-12-02 | Merck & Co., Inc. | 2,3-Dihydro-2,6,7-trisubstituted-5-acylbenzofurans |
| IL101785A0 (en) * | 1991-05-10 | 1992-12-30 | Fujisawa Pharmaceutical Co | Urea derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same |
| US5436246A (en) * | 1992-09-17 | 1995-07-25 | Merrell Dow Pharmaceuticals Inc. | Serotonin receptor agents |
| JP2759257B2 (ja) * | 1993-09-28 | 1998-05-28 | 大塚製薬株式会社 | 糖尿病治療剤 |
| JPH07173158A (ja) * | 1993-12-17 | 1995-07-11 | Taiho Yakuhin Kogyo Kk | チアゾリジンジオン誘導体又はその塩 |
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| US6130187A (en) * | 1996-02-09 | 2000-10-10 | Kumiai Chemical Industry Co., Ltd. | Benzofuran-7-yl uracil derivatives and herbicides |
| US6077812A (en) * | 1997-02-26 | 2000-06-20 | Fmc Corporation | Cycloimido-substituted benzofused heterocyclic herbicides |
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| EP0978512A1 (en) * | 1998-07-29 | 2000-02-09 | Societe Civile Bioprojet | Non-imidazole aryloxy (or arylthio) alkylamines as histamine H3-receptor antagonists and their therapeutic applications |
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| WO2002010156A1 (en) * | 2000-07-29 | 2002-02-07 | Arpida Ag | Benzofuran derivatives and their use as antibacterial agents |
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| AR035783A1 (es) | 2004-07-14 |
| BR0205829A (pt) | 2005-03-08 |
| MXPA03008319A (es) | 2003-12-11 |
| JP2005500986A (ja) | 2005-01-13 |
| EP2258694A1 (en) | 2010-12-08 |
| WO2002074758A2 (en) | 2002-09-26 |
| WO2002074758A3 (en) | 2003-03-20 |
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