JP2017519798A5 - - Google Patents
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- JP2017519798A5 JP2017519798A5 JP2017500331A JP2017500331A JP2017519798A5 JP 2017519798 A5 JP2017519798 A5 JP 2017519798A5 JP 2017500331 A JP2017500331 A JP 2017500331A JP 2017500331 A JP2017500331 A JP 2017500331A JP 2017519798 A5 JP2017519798 A5 JP 2017519798A5
- Authority
- JP
- Japan
- Prior art keywords
- membered heterocyclyl
- alkyl
- membered
- compound
- independently
- 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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- 125000000623 heterocyclic group Chemical group 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- -1 R 2 is D Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 208000012902 Nervous system disease Diseases 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 8
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 8
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 8
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 8
- 208000015114 central nervous system disease Diseases 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 8
- 102000005962 receptors Human genes 0.000 claims description 8
- 108020003175 receptors Proteins 0.000 claims description 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000002207 metabolite Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000000651 prodrug Substances 0.000 claims description 6
- 229940002612 prodrug Drugs 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 208000020925 Bipolar disease Diseases 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 208000023105 Huntington disease Diseases 0.000 claims description 4
- 208000026139 Memory disease Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 150000001555 benzenes Chemical group 0.000 claims description 4
- 208000028683 bipolar I disease Diseases 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical group O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 claims description 4
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 claims description 4
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- GBBSUAFBMRNDJC-MRXNPFEDSA-N (5R)-zopiclone Chemical compound C1CN(C)CCN1C(=O)O[C@@H]1C2=NC=CN=C2C(=O)N1C1=CC=C(Cl)C=N1 GBBSUAFBMRNDJC-MRXNPFEDSA-N 0.000 claims description 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- MAYQIFVKVAUMPD-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-methyl-4-piperazin-1-ylbenzimidazole Chemical compound CC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 MAYQIFVKVAUMPD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- WJBLNOPPDWQMCH-MBPVOVBZSA-N Nalmefene Chemical compound N1([C@@H]2CC3=CC=C(C=4O[C@@H]5[C@](C3=4)([C@]2(CCC5=C)O)CC1)O)CC1CC1 WJBLNOPPDWQMCH-MBPVOVBZSA-N 0.000 claims description 2
- PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 claims description 2
- BYPFEZZEUUWMEJ-UHFFFAOYSA-N Pentoxifylline Chemical compound O=C1N(CCCCC(=O)C)C(=O)N(C)C2=C1N(C)C=N2 BYPFEZZEUUWMEJ-UHFFFAOYSA-N 0.000 claims description 2
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims description 2
- XNBRWUQWSKXMPW-UHFFFAOYSA-N Tozadenant Chemical compound C1=2SC(NC(=O)N3CCC(C)(O)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 XNBRWUQWSKXMPW-UHFFFAOYSA-N 0.000 claims description 2
- 229930003427 Vitamin E Natural products 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- PMKMNTBZJOXTJW-UHFFFAOYSA-N brilaroxazine Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)COC4=CC=3)CC2)=C1Cl PMKMNTBZJOXTJW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 229960003530 donepezil Drugs 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 229960003980 galantamine Drugs 0.000 claims description 2
- ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 claims description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 claims description 2
- 229960004640 memantine Drugs 0.000 claims description 2
- 229960001785 mirtazapine Drugs 0.000 claims description 2
- RONZAEMNMFQXRA-UHFFFAOYSA-N mirtazapine Chemical compound C1C2=CC=CN=C2N2CCN(C)CC2C2=CC=CC=C21 RONZAEMNMFQXRA-UHFFFAOYSA-N 0.000 claims description 2
- 229960005297 nalmefene Drugs 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229960001158 nortriptyline Drugs 0.000 claims description 2
- 125000003566 oxetanyl group Chemical group 0.000 claims description 2
- 229960001476 pentoxifylline Drugs 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims description 2
- 229960001534 risperidone Drugs 0.000 claims description 2
- 229960004136 rivastigmine Drugs 0.000 claims description 2
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 claims description 2
- 229960003946 selegiline Drugs 0.000 claims description 2
- 229960001685 tacrine Drugs 0.000 claims description 2
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000002053 thietanyl group Chemical group 0.000 claims description 2
- 229950000564 tozadenant Drugs 0.000 claims description 2
- 239000003981 vehicle Substances 0.000 claims description 2
- 229960004688 venlafaxine Drugs 0.000 claims description 2
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 claims description 2
- 229940046009 vitamin E Drugs 0.000 claims description 2
- 235000019165 vitamin E Nutrition 0.000 claims description 2
- 239000011709 vitamin E Substances 0.000 claims description 2
- 229960001475 zolpidem Drugs 0.000 claims description 2
- ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 claims description 2
- 229960000820 zopiclone Drugs 0.000 claims description 2
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 230000002496 gastric effect Effects 0.000 claims 1
- 0 CICC*1CCNCC1 Chemical compound CICC*1CCNCC1 0.000 description 7
- 238000000034 method Methods 0.000 description 4
- 208000018522 Gastrointestinal disease Diseases 0.000 description 3
- 206010028289 Muscle atrophy Diseases 0.000 description 3
- 208000010643 digestive system disease Diseases 0.000 description 3
- 208000018685 gastrointestinal system disease Diseases 0.000 description 3
- 201000010901 lateral sclerosis Diseases 0.000 description 3
- 208000005264 motor neuron disease Diseases 0.000 description 3
- 230000020763 muscle atrophy Effects 0.000 description 3
- 201000000585 muscular atrophy Diseases 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 2
- IBUHDDLETPJVGP-UHFFFAOYSA-N 2,8-dimethyl-5-(2-phenylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CC=CC=C1 IBUHDDLETPJVGP-UHFFFAOYSA-N 0.000 description 1
- KSAUCBGUWGWPDL-UHFFFAOYSA-N 3-(benzenesulfonyl)-5,7-dimethyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(C)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 KSAUCBGUWGWPDL-UHFFFAOYSA-N 0.000 description 1
- HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 1
- YSEXMKHXIOCEJA-FVFQAYNVSA-N Nicergoline Chemical compound C([C@@H]1C[C@]2([C@H](N(C)C1)CC=1C3=C2C=CC=C3N(C)C=1)OC)OC(=O)C1=CN=CC(Br)=C1 YSEXMKHXIOCEJA-FVFQAYNVSA-N 0.000 description 1
- MDCHPQGOHLNQKV-UHFFFAOYSA-N O=S(c1cc(Br)ccc1)=O Chemical compound O=S(c1cc(Br)ccc1)=O MDCHPQGOHLNQKV-UHFFFAOYSA-N 0.000 description 1
- OSYRGIKTRBURDS-UHFFFAOYSA-N O=S(c1ccccc1C(F)(F)F)=O Chemical compound O=S(c1ccccc1C(F)(F)F)=O OSYRGIKTRBURDS-UHFFFAOYSA-N 0.000 description 1
- GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 description 1
- 229960003914 desipramine Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 229960003642 nicergoline Drugs 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 229960004526 piracetam Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410324179.6 | 2014-07-08 | ||
| CN201410324179 | 2014-07-08 | ||
| PCT/CN2015/083605 WO2016004882A1 (en) | 2014-07-08 | 2015-07-08 | Aromatic heterocyclic derivatives and pharmaceutical applications thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017519798A JP2017519798A (ja) | 2017-07-20 |
| JP2017519798A5 true JP2017519798A5 (https=) | 2018-08-02 |
| JP6515175B2 JP6515175B2 (ja) | 2019-05-15 |
Family
ID=55063598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017500331A Active JP6515175B2 (ja) | 2014-07-08 | 2015-07-08 | 芳香族ヘテロ環誘導体及びその医薬的適用 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9974785B2 (https=) |
| EP (1) | EP3166924B1 (https=) |
| JP (1) | JP6515175B2 (https=) |
| CN (1) | CN105541693B (https=) |
| AU (1) | AU2015286049B2 (https=) |
| CA (1) | CA2953004C (https=) |
| SG (1) | SG11201610407QA (https=) |
| WO (1) | WO2016004882A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109232362B (zh) * | 2017-07-10 | 2022-12-27 | 广东东阳光药业有限公司 | 芳杂环类衍生物及其在药物上的应用 |
| WO2020117075A1 (en) * | 2018-12-06 | 2020-06-11 | Jagiellonian University | Arylsulfonamides of 2-arylpyrrole-3-carboxamides for the treatment of cns disorders |
| CN111233736B (zh) * | 2020-03-16 | 2021-07-16 | 东莞市东阳光新药研发有限公司 | 芳杂环类衍生物的盐及其用途 |
| CN111362858B (zh) * | 2020-03-16 | 2021-05-11 | 东莞市东阳光新药研发有限公司 | 芳杂环类衍生物的盐及其用途 |
| CN111362859B (zh) * | 2020-03-16 | 2021-05-11 | 东莞市东阳光新药研发有限公司 | 芳杂环类衍生物的盐及其用途 |
| CN111233737B (zh) * | 2020-03-16 | 2021-05-11 | 东莞市东阳光新药研发有限公司 | 芳杂环类衍生物的盐及其用途 |
| CN117024326A (zh) * | 2023-07-26 | 2023-11-10 | 平顶山学院 | 5位氨基取代吲哚化合物及其制备方法和在抗乙酰胆碱酯酶药物中的应用 |
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| US6100291A (en) * | 1998-03-16 | 2000-08-08 | Allelix Biopharmaceuticals Inc. | Pyrrolidine-indole compounds having 5-HT6 affinity |
| ATE375990T1 (de) | 1999-04-21 | 2007-11-15 | Nps Allelix Corp | Piperidin-indol derivate mit 5-ht6 affinität |
| WO2001012629A1 (en) | 1999-08-12 | 2001-02-22 | Nps Allelix Corp. | Azaindoles having serotonin receptor affinity |
| US6897215B1 (en) | 1999-11-05 | 2005-05-24 | Nps Allelix Corp. | Compounds having 5-HT6 receptor antagonist activity |
| AU2001296193B2 (en) | 2000-10-20 | 2006-04-27 | Biovitrum Ab | 2-, 3-, 4-, or 5-substituted-N1-(benzensulfonyl)indoles and their use in therapy |
| US7034029B2 (en) | 2000-11-02 | 2006-04-25 | Wyeth | 1-aryl- or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6 ligands |
| EP2298738B1 (en) * | 2000-11-02 | 2012-09-19 | Wyeth LLC | 1-aryl- or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6 ligands |
| AU2002220715A1 (en) | 2000-11-24 | 2002-06-03 | Smithkline Beecham Plc | Indolsulfonyl compounds useful in the treatment of cns disorders |
| EA200300716A1 (ru) | 2000-12-22 | 2003-12-25 | Уайт | Гетероциклилалкилиндольные или -азаиндольные соединения в качестве лиганд 5-гидрокситриптамина-6 |
| MXPA03005432A (es) | 2000-12-22 | 2003-09-10 | Wyeth Corp | Compuestos de heterociclilindazol y -azaindazol como ligandos de 5-hidroxitriptamina-6. |
| US7271180B2 (en) | 2001-01-23 | 2007-09-18 | Wyeth | 1-Aryl-or 1-alkylsulfonylbenzazole derivatives as 5-hydroxytryptamine-6 ligands |
| TW593278B (en) | 2001-01-23 | 2004-06-21 | Wyeth Corp | 1-aryl-or 1-alkylsulfonylbenzazole derivatives as 5-hydroxytryptamine-6 ligands |
| ATE340795T1 (de) | 2001-01-30 | 2006-10-15 | Lilly Co Eli | Benzolsulfonsäureester-indol-5-yl als 5-ht6 rezeptor-antagonisten |
| CA2444095A1 (en) | 2001-04-20 | 2002-10-31 | Wyeth | Heterocyclyloxy-, -thioxy- and -aminobenzazole derivatives as 5-hydroxytryptamine-6 ligands |
| WO2002085853A2 (en) | 2001-04-20 | 2002-10-31 | Wyeth | Heterocyclylalkoxy-, -alkylthio- and -alkylaminobenzazole derivatives as 5-hydroxytryptamine-6 ligands |
| EP1401813B1 (en) | 2001-06-07 | 2007-02-07 | F. Hoffman-la Roche AG | New indole derivatives with 5-ht6 receptor affinity |
| CN1321110C (zh) * | 2001-06-15 | 2007-06-13 | 弗·哈夫曼-拉罗切有限公司 | 具有5-ht6受体亲和力的4-哌嗪基吲哚衍生物 |
| DE60212841T2 (de) | 2001-06-15 | 2007-06-21 | F. Hoffmann-La Roche Ag | 4 piperazinylindolderivate mit affinität zum 5-ht6-rezeptor |
| WO2003013510A1 (en) | 2001-08-07 | 2003-02-20 | Smithkline Beecham P.L.C. | 3-arylsulfonyl-7-piperazinyl- indoles, -benzofurans and -benzothiophenes with 5-ht6 receptor affinity for treating cns disorders |
| TW200301251A (en) | 2001-12-20 | 2003-07-01 | Wyeth Corp | Azaindolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands |
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| DE60322186D1 (de) | 2002-02-12 | 2008-08-28 | Organon Nv | 1-arylsulfonyl-3-substituierte indol und indolinederivate verwendbar zur behandlung von erkrankungen des zentralnervensystem |
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-
2015
- 2015-07-08 EP EP15819721.0A patent/EP3166924B1/en active Active
- 2015-07-08 WO PCT/CN2015/083605 patent/WO2016004882A1/en not_active Ceased
- 2015-07-08 JP JP2017500331A patent/JP6515175B2/ja active Active
- 2015-07-08 AU AU2015286049A patent/AU2015286049B2/en active Active
- 2015-07-08 CA CA2953004A patent/CA2953004C/en active Active
- 2015-07-08 US US15/314,932 patent/US9974785B2/en active Active
- 2015-07-08 SG SG11201610407QA patent/SG11201610407QA/en unknown
- 2015-07-08 CN CN201510401669.6A patent/CN105541693B/zh active Active
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