JP2006505559A5 - - Google Patents
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- Publication number
- JP2006505559A5 JP2006505559A5 JP2004544204A JP2004544204A JP2006505559A5 JP 2006505559 A5 JP2006505559 A5 JP 2006505559A5 JP 2004544204 A JP2004544204 A JP 2004544204A JP 2004544204 A JP2004544204 A JP 2004544204A JP 2006505559 A5 JP2006505559 A5 JP 2006505559A5
- Authority
- JP
- Japan
- Prior art keywords
- indole
- benzenesulfonyl
- piperazin
- formula
- hydrogen
- 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.)
- Pending
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims 33
- 239000001257 hydrogen Substances 0.000 claims 33
- 150000001875 compounds Chemical class 0.000 claims 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 22
- 125000005843 halogen group Chemical group 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 150000002431 hydrogen Chemical class 0.000 claims 11
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 238000000034 method Methods 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- -1 nitro, amino Chemical group 0.000 claims 3
- ISGSSIOGLLTWCV-UHFFFAOYSA-N 5-bromo-3-[2-chloro-4-(4-methylpiperazin-1-yl)phenyl]sulfonyl-1h-indole Chemical compound C1CN(C)CCN1C1=CC=C(S(=O)(=O)C=2C3=CC(Br)=CC=C3NC=2)C(Cl)=C1 ISGSSIOGLLTWCV-UHFFFAOYSA-N 0.000 claims 2
- AFBFLUVKIUCKDX-UHFFFAOYSA-N 7-bromo-3-(4-piperazin-1-ylphenyl)sulfonyl-1h-indole Chemical compound C=1NC=2C(Br)=CC=CC=2C=1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 AFBFLUVKIUCKDX-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- OOMFLFHKRGRSPZ-UHFFFAOYSA-N 1-(4-piperazin-1-ylphenyl)sulfonylindole Chemical compound C1=CC2=CC=CC=C2N1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 OOMFLFHKRGRSPZ-UHFFFAOYSA-N 0.000 claims 1
- WLMHUVOJWSRCKQ-UHFFFAOYSA-N 1-methyl-3-(4-piperazin-1-ylphenyl)sulfonylindole Chemical compound C12=CC=CC=C2N(C)C=C1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 WLMHUVOJWSRCKQ-UHFFFAOYSA-N 0.000 claims 1
- YYTPFJPXIXRCIO-UHFFFAOYSA-N 2-(4-piperazin-1-ylphenyl)sulfonyl-1h-indole Chemical compound C=1C2=CC=CC=C2NC=1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 YYTPFJPXIXRCIO-UHFFFAOYSA-N 0.000 claims 1
- JACMPYPWLNSPQD-UHFFFAOYSA-N 3-(2-chloro-4-piperazin-1-ylphenyl)sulfonyl-1h-indole Chemical compound C=1C=C(S(=O)(=O)C=2C3=CC=CC=C3NC=2)C(Cl)=CC=1N1CCNCC1 JACMPYPWLNSPQD-UHFFFAOYSA-N 0.000 claims 1
- LKCVRAPSEZQHSZ-UHFFFAOYSA-N 3-(3-chloro-4-piperazin-1-ylphenyl)sulfonyl-1h-indole Chemical compound ClC1=CC(S(=O)(=O)C=2C3=CC=CC=C3NC=2)=CC=C1N1CCNCC1 LKCVRAPSEZQHSZ-UHFFFAOYSA-N 0.000 claims 1
- RYDIZDOFZGMJKT-UHFFFAOYSA-N 3-(4-piperazin-1-ylphenyl)sulfonyl-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 RYDIZDOFZGMJKT-UHFFFAOYSA-N 0.000 claims 1
- LGTAZVZDQDIXDZ-UHFFFAOYSA-N 3-[2-chloro-4-(4-methylpiperazin-1-yl)phenyl]sulfonyl-1h-indole Chemical compound C1CN(C)CCN1C1=CC=C(S(=O)(=O)C=2C3=CC=CC=C3NC=2)C(Cl)=C1 LGTAZVZDQDIXDZ-UHFFFAOYSA-N 0.000 claims 1
- FEMFCXPLXZIQJH-UHFFFAOYSA-N 3-[3-chloro-4-(4-methylpiperazin-1-yl)phenyl]sulfonyl-1h-indole Chemical compound C1CN(C)CCN1C1=CC=C(S(=O)(=O)C=2C3=CC=CC=C3NC=2)C=C1Cl FEMFCXPLXZIQJH-UHFFFAOYSA-N 0.000 claims 1
- WSWQWXORZNKMSF-UHFFFAOYSA-N 3-[4-(4-methylpiperazin-1-yl)phenyl]sulfonyl-1h-indole Chemical compound C1CN(C)CCN1C1=CC=C(S(=O)(=O)C=2C3=CC=CC=C3NC=2)C=C1 WSWQWXORZNKMSF-UHFFFAOYSA-N 0.000 claims 1
- GDEWOLSRDYNASG-UHFFFAOYSA-N 3-chloro-5-methoxy-2-methyl-1-(4-piperazin-1-ylphenyl)sulfonylindole Chemical compound CC1=C(Cl)C2=CC(OC)=CC=C2N1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 GDEWOLSRDYNASG-UHFFFAOYSA-N 0.000 claims 1
- PXRHNGDHDXJYIZ-UHFFFAOYSA-N 4-bromo-1-(4-piperazin-1-ylphenyl)sulfonylindole Chemical compound C1=CC=2C(Br)=CC=CC=2N1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 PXRHNGDHDXJYIZ-UHFFFAOYSA-N 0.000 claims 1
- MAUAPTQUIAAEBA-UHFFFAOYSA-N 4-bromo-3-(4-piperazin-1-ylphenyl)sulfonyl-1h-indole Chemical compound C1=2C(Br)=CC=CC=2NC=C1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 MAUAPTQUIAAEBA-UHFFFAOYSA-N 0.000 claims 1
- OTZYHGDDQOZUIU-UHFFFAOYSA-N 4-bromo-3-[4-(4-methylpiperazin-1-yl)phenyl]sulfonyl-1h-indole Chemical compound C1CN(C)CCN1C1=CC=C(S(=O)(=O)C=2C3=C(Br)C=CC=C3NC=2)C=C1 OTZYHGDDQOZUIU-UHFFFAOYSA-N 0.000 claims 1
- YRQISXJTIXMQQR-UHFFFAOYSA-N 4-chloro-3-(4-piperazin-1-ylphenyl)sulfonyl-1h-indole Chemical compound C1=2C(Cl)=CC=CC=2NC=C1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 YRQISXJTIXMQQR-UHFFFAOYSA-N 0.000 claims 1
- CTRHPFJATTYDGB-UHFFFAOYSA-N 5-bromo-1-methyl-3-(4-piperazin-1-ylphenyl)sulfonylindole Chemical compound C12=CC(Br)=CC=C2N(C)C=C1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 CTRHPFJATTYDGB-UHFFFAOYSA-N 0.000 claims 1
- MFVUYKVLRRWVPR-UHFFFAOYSA-N 5-bromo-3-(2-chloro-4-piperazin-1-ylphenyl)sulfonyl-1h-indole Chemical compound C=1C=C(S(=O)(=O)C=2C3=CC(Br)=CC=C3NC=2)C(Cl)=CC=1N1CCNCC1 MFVUYKVLRRWVPR-UHFFFAOYSA-N 0.000 claims 1
- TYFIZEFFLOJFTP-UHFFFAOYSA-N 5-bromo-3-(3-chloro-4-piperazin-1-ylphenyl)sulfonyl-1h-indole Chemical compound ClC1=CC(S(=O)(=O)C=2C3=CC(Br)=CC=C3NC=2)=CC=C1N1CCNCC1 TYFIZEFFLOJFTP-UHFFFAOYSA-N 0.000 claims 1
- JLXBHKYSTCWZTK-UHFFFAOYSA-N 5-bromo-3-(4-piperazin-1-ylphenyl)sulfonyl-1h-indole Chemical compound C12=CC(Br)=CC=C2NC=C1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 JLXBHKYSTCWZTK-UHFFFAOYSA-N 0.000 claims 1
- IWVDLGDVSVECHM-UHFFFAOYSA-N 5-bromo-3-[3-chloro-4-(4-methylpiperazin-1-yl)phenyl]sulfonyl-1h-indole Chemical compound C1CN(C)CCN1C1=CC=C(S(=O)(=O)C=2C3=CC(Br)=CC=C3NC=2)C=C1Cl IWVDLGDVSVECHM-UHFFFAOYSA-N 0.000 claims 1
- RMFJRKWIQAACGL-UHFFFAOYSA-N 5-chloro-3-(2-chloro-4-piperazin-1-ylphenyl)sulfonyl-1h-indole Chemical compound C12=CC(Cl)=CC=C2NC=C1S(=O)(=O)C(C(=C1)Cl)=CC=C1N1CCNCC1 RMFJRKWIQAACGL-UHFFFAOYSA-N 0.000 claims 1
- QNIAWKUXHBKLLH-UHFFFAOYSA-N 5-chloro-3-(3-chloro-4-piperazin-1-ylphenyl)sulfonyl-1h-indole Chemical compound C12=CC(Cl)=CC=C2NC=C1S(=O)(=O)C(C=C1Cl)=CC=C1N1CCNCC1 QNIAWKUXHBKLLH-UHFFFAOYSA-N 0.000 claims 1
- LNAQZIOZOUSWIY-UHFFFAOYSA-N 5-chloro-3-(4-piperazin-1-ylphenyl)sulfonyl-1h-indole Chemical compound C12=CC(Cl)=CC=C2NC=C1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 LNAQZIOZOUSWIY-UHFFFAOYSA-N 0.000 claims 1
- UKTJDUKCVYUJBO-UHFFFAOYSA-N 5-chloro-3-[2-chloro-4-(4-methylpiperazin-1-yl)phenyl]sulfonyl-1h-indole Chemical compound C1CN(C)CCN1C1=CC=C(S(=O)(=O)C=2C3=CC(Cl)=CC=C3NC=2)C(Cl)=C1 UKTJDUKCVYUJBO-UHFFFAOYSA-N 0.000 claims 1
- VPCXTEQXBRAHAT-UHFFFAOYSA-N 5-chloro-3-[3-chloro-4-(4-methylpiperazin-1-yl)phenyl]sulfonyl-1h-indole Chemical compound C1CN(C)CCN1C1=CC=C(S(=O)(=O)C=2C3=CC(Cl)=CC=C3NC=2)C=C1Cl VPCXTEQXBRAHAT-UHFFFAOYSA-N 0.000 claims 1
- IJDFGMWOCZUGIA-UHFFFAOYSA-N 5-fluoro-1-(4-piperazin-1-ylphenyl)sulfonylindole Chemical compound C1=CC2=CC(F)=CC=C2N1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 IJDFGMWOCZUGIA-UHFFFAOYSA-N 0.000 claims 1
- GNSVEUXJFZGGOY-UHFFFAOYSA-N 5-fluoro-1-[4-(4-methylpiperazin-1-yl)phenyl]sulfonylindole Chemical compound C1CN(C)CCN1C1=CC=C(S(=O)(=O)N2C3=CC=C(F)C=C3C=C2)C=C1 GNSVEUXJFZGGOY-UHFFFAOYSA-N 0.000 claims 1
- FTJHIQQEYSOQEA-UHFFFAOYSA-N 5-iodo-3-(4-piperazin-1-ylphenyl)sulfonyl-1h-indole Chemical compound C12=CC(I)=CC=C2NC=C1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 FTJHIQQEYSOQEA-UHFFFAOYSA-N 0.000 claims 1
- CHPMMVLTFIILRX-UHFFFAOYSA-N 5-iodo-3-[4-(4-methylpiperazin-1-yl)phenyl]sulfonyl-1h-indole Chemical compound C1CN(C)CCN1C1=CC=C(S(=O)(=O)C=2C3=CC(I)=CC=C3NC=2)C=C1 CHPMMVLTFIILRX-UHFFFAOYSA-N 0.000 claims 1
- XLOAFEHWSDWHED-UHFFFAOYSA-N 5-methoxy-1-(4-piperazin-1-ylphenyl)sulfonylindole Chemical compound C1=CC2=CC(OC)=CC=C2N1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 XLOAFEHWSDWHED-UHFFFAOYSA-N 0.000 claims 1
- NAZZZXXATCFXTN-UHFFFAOYSA-N 5-methoxy-3-(4-piperazin-1-ylphenyl)sulfonyl-1h-indole Chemical compound C12=CC(OC)=CC=C2NC=C1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 NAZZZXXATCFXTN-UHFFFAOYSA-N 0.000 claims 1
- FVOUVWDFVUPNII-UHFFFAOYSA-N 6-bromo-3-(4-piperazin-1-ylphenyl)sulfonyl-1h-indole Chemical compound C=1NC2=CC(Br)=CC=C2C=1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 FVOUVWDFVUPNII-UHFFFAOYSA-N 0.000 claims 1
- MYSXZZBJNMPUQB-UHFFFAOYSA-N 6-bromo-3-[4-(4-methylpiperazin-1-yl)phenyl]sulfonyl-1h-indole Chemical compound C1CN(C)CCN1C1=CC=C(S(=O)(=O)C=2C3=CC=C(Br)C=C3NC=2)C=C1 MYSXZZBJNMPUQB-UHFFFAOYSA-N 0.000 claims 1
- DKSYHWKIVGZOHE-UHFFFAOYSA-N 6-chloro-1-methyl-3-(4-piperazin-1-ylphenyl)sulfonylindole Chemical compound C12=CC=C(Cl)C=C2N(C)C=C1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 DKSYHWKIVGZOHE-UHFFFAOYSA-N 0.000 claims 1
- UCLAJUPNMNVACK-UHFFFAOYSA-N 6-chloro-3-(4-piperazin-1-ylphenyl)sulfonyl-1h-indole Chemical compound C=1NC2=CC(Cl)=CC=C2C=1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 UCLAJUPNMNVACK-UHFFFAOYSA-N 0.000 claims 1
- SPJHNOUCULEGKT-UHFFFAOYSA-N 7-bromo-3-[4-(4-methylpiperazin-1-yl)phenyl]sulfonyl-1h-indole Chemical compound C1CN(C)CCN1C1=CC=C(S(=O)(=O)C=2C3=CC=CC(Br)=C3NC=2)C=C1 SPJHNOUCULEGKT-UHFFFAOYSA-N 0.000 claims 1
- LTNVVSWBOXRSQN-UHFFFAOYSA-N 7-chloro-3-(4-piperazin-1-ylphenyl)sulfonyl-1h-indole Chemical compound C=1NC=2C(Cl)=CC=CC=2C=1S(=O)(=O)C(C=C1)=CC=C1N1CCNCC1 LTNVVSWBOXRSQN-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 125000005110 aryl thio group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 208000028683 bipolar I disease Diseases 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N CC1CCCC1 Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41936902P | 2002-10-18 | 2002-10-18 | |
| PCT/EP2003/011323 WO2004035047A1 (en) | 2002-10-18 | 2003-10-13 | 4-piperazinyl benzenesulfonyl indoles with 5-ht6 receptor affinity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006505559A JP2006505559A (ja) | 2006-02-16 |
| JP2006505559A5 true JP2006505559A5 (https=) | 2006-11-30 |
Family
ID=32108067
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004544204A Pending JP2006505559A (ja) | 2002-10-18 | 2003-10-13 | ５−ｈｔ６受容体親和性を持つ４−ピペラジニルベンゼンスルホニルインドール |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US7022708B2 (https=) |
| EP (1) | EP1556037B1 (https=) |
| JP (1) | JP2006505559A (https=) |
| KR (1) | KR20050073560A (https=) |
| CN (1) | CN1309384C (https=) |
| AR (1) | AR041635A1 (https=) |
| AT (1) | ATE344030T1 (https=) |
| AU (1) | AU2003283265B2 (https=) |
| BR (1) | BR0315317A (https=) |
| CA (1) | CA2501172A1 (https=) |
| DE (1) | DE60309498T2 (https=) |
| ES (1) | ES2274285T3 (https=) |
| GT (1) | GT200300226A (https=) |
| MX (1) | MXPA05004128A (https=) |
| PA (1) | PA8586401A1 (https=) |
| PE (1) | PE20040691A1 (https=) |
| PL (1) | PL376479A1 (https=) |
| RU (1) | RU2324693C2 (https=) |
| TW (1) | TW200418456A (https=) |
| UY (1) | UY28026A1 (https=) |
| WO (1) | WO2004035047A1 (https=) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1401813B1 (en) * | 2001-06-07 | 2007-02-07 | F. Hoffman-la Roche AG | New indole derivatives with 5-ht6 receptor affinity |
| BRPI0308696B8 (pt) | 2002-03-27 | 2021-05-25 | Axovant Sciences Gmbh | composto derivado de quinolina, seu processo de preparação, sua composição farmacêutica e seus usos |
| PT1558582E (pt) | 2003-07-22 | 2006-05-31 | Arena Pharm Inc | Derivados de diaril- e aril-heteroaril-ureia como moduladores do receptor de serotonina 5-ht2a uteis para a profilaxia e tratamento de desordens relacionadas com o mesmo |
| US8076352B2 (en) | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Administration of carboline derivatives useful in the treatment of cancer and other diseases |
| MXPA06010543A (es) | 2004-03-15 | 2007-03-26 | Ptc Therapeutics Inc | Derivados de carbolina utiles en la inhibicion de la angiogenesis. |
| US7767689B2 (en) | 2004-03-15 | 2010-08-03 | Ptc Therapeutics, Inc. | Carboline derivatives useful in the treatment of cancer |
| US8076353B2 (en) | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Inhibition of VEGF translation |
| EP1771169A1 (en) | 2004-07-14 | 2007-04-11 | PTC Therapeutics, Inc. | Methods for treating hepatitis c |
| US7868037B2 (en) | 2004-07-14 | 2011-01-11 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| US7772271B2 (en) | 2004-07-14 | 2010-08-10 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| AR052308A1 (es) * | 2004-07-16 | 2007-03-14 | Lundbeck & Co As H | Derivados de 2-(1h-indolilsulfanil)-arilamina y una composicion farmaceutica que contiene al compuesto |
| JP2008507518A (ja) | 2004-07-22 | 2008-03-13 | ピーティーシー セラピューティクス，インコーポレーテッド | Ｃ型肝炎を治療するためのチエノピリジン |
| CN102114244A (zh) | 2004-09-30 | 2011-07-06 | 弗·哈夫曼-拉罗切有限公司 | 治疗认知障碍的组合物和方法 |
| US7713954B2 (en) * | 2004-09-30 | 2010-05-11 | Roche Palo Alto Llc | Compositions and methods for treating cognitive disorders |
| EA013875B1 (ru) | 2005-08-12 | 2010-08-30 | Сувен Лайф Сайенсиз Лимитед | Аминоарильные сульфонамидные производные как функциональные 5-нтлиганды |
| BRPI0614343A2 (pt) * | 2005-08-15 | 2011-03-22 | Wyeth Corp | derivados de 3-sulfonilindazol substituìdo como ligantes de 5-hidroxitriptamina-6 |
| WO2007020654A1 (en) | 2005-08-16 | 2007-02-22 | Suven Life Sciences | An improved process for the preparation of losartan |
| WO2007084841A2 (en) * | 2006-01-13 | 2007-07-26 | Wyeth | Sulfonyl substituted 1h-indoles as ligands for the 5-hydroxytryptamine receptors |
| ES2358549T3 (es) | 2006-11-09 | 2011-05-11 | F. Hoffmann-La Roche Ag | Arilsulfonil, pirrolidinas como inhibidores de 5-ht6. |
| JP5208963B2 (ja) | 2007-01-10 | 2013-06-12 | エフ．ホフマン−ラ ロシュ アーゲー | キマーゼ阻害剤としてのスルホンアミド誘導体 |
| CN101835748B (zh) * | 2007-10-26 | 2012-11-14 | 苏文生命科学有限公司 | 氨基芳基磺胺化合物及其作为5-ht6配体的用途 |
| EP2508177A1 (en) | 2007-12-12 | 2012-10-10 | Glaxo Group Limited | Combinations comprising 3-phenylsulfonyl-8-piperazinyl-1yl-quinoline |
| WO2009123714A2 (en) | 2008-04-02 | 2009-10-08 | Arena Pharmaceuticals, Inc. | Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor |
| WO2010032257A1 (en) * | 2008-09-17 | 2010-03-25 | Suven Life Sciences Limited | Aryl indolyl sulfonamide compounds and their use as 5-ht6 ligands |
| WO2010062321A1 (en) | 2008-10-28 | 2010-06-03 | Arena Pharmaceuticals, Inc. | Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2h-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)-urea and crystalline forms related thereto |
| US8575186B2 (en) | 2009-10-05 | 2013-11-05 | Albany Molecular Research, Inc. | Epiminocycloalkyl[b] indole derivatives as serotonin sub-type 6 (5-HT6) modulators and uses thereof |
| AU2012207335A1 (en) | 2011-01-19 | 2013-07-25 | Albany Molecular Research, Inc. | Benzofuro[3,2-c] pyridines and related analogs as serotonin sub-type 6 (5-HT6) modulators for the treatment of obesity, metabolic syndrome, cognition and schizophrenia |
| DK2838533T3 (da) | 2012-04-16 | 2017-11-27 | Univ Case Western Reserve | Sammensætninger og fremgangsmåder til at modulere 15-pgdh-aktivitet |
| US9801863B2 (en) | 2012-04-16 | 2017-10-31 | Case Western Reserve University | Inhibitors of short-chain dehydrogenase activity for modulating hematopoietic stem cells and hematopoiesis |
| CN104276993B (zh) * | 2013-07-12 | 2019-03-15 | 广东东阳光药业有限公司 | 吲哚衍生物及其在药物上的应用 |
| AU2014342811B2 (en) | 2013-10-15 | 2019-01-03 | Board Of Regents Of The University Of Texas System | Compositions and methods of modulating short-chain dehydrogenase activity |
| CN104557726B (zh) * | 2013-10-19 | 2019-05-24 | 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 |
| WO2015090233A1 (en) | 2013-12-20 | 2015-06-25 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic compounds and their application in pharmaceuticals |
| EP3166924B1 (en) * | 2014-07-08 | 2019-02-20 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic derivatives and pharmaceutical applications thereof |
| WO2016201373A1 (en) | 2015-06-12 | 2016-12-15 | Axovant Sciences Ltd. | Diaryl and arylheteroaryl urea derivatives useful for the prophylaxis and treatment of rem sleep behavior disorder |
| WO2017011767A2 (en) | 2015-07-15 | 2017-01-19 | Axovant Sciences Ltd. | Diaryl and arylheteroaryl urea derivatives as modulators of the 5-ht2a serotonin receptor useful for the prophylaxis and treatment of hallucinations associated with a neurodegenerative disease |
| JP7595413B2 (ja) | 2016-11-30 | 2024-12-06 | ケース ウエスタン リザーブ ユニバーシティ | １５－ｐｇｄｈ阻害剤とコルチコステロイドおよび／またはｔｎｆ阻害剤との組み合わせならびにその使用 |
| WO2018145080A1 (en) | 2017-02-06 | 2018-08-09 | Case Western Reserve University | Compositions and methods of modulating short-chain dehydrogenase activity |
| 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 |
| CN120463721A (zh) | 2018-11-21 | 2025-08-12 | 卡斯西部储备大学 | 调节短链脱氢酶活性的组合物和方法 |
| FI4426434T3 (fi) | 2021-11-02 | 2025-11-24 | Flare Therapeutics Inc | Pparg:n käänteisagonisteja ja niiden käyttöjä |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB9116732D0 (en) | 1991-08-02 | 1991-09-18 | Fujisawa Pharmaceutical Co | Indole derivatives |
| FR2729144A1 (fr) | 1995-01-06 | 1996-07-12 | Smithkline Beecham Lab | Nouvelles diamines, leur procede de preparation et leur utilisation en tant que medicaments et notamment en tant qu' agents anti-arythmiques |
| DZ2376A1 (fr) | 1996-12-19 | 2002-12-28 | Smithkline Beecham Plc | Dérivés de sulfonamides nouveaux procédé pour leurpréparation et compositions pharmaceutiques les c ontenant. |
| AU736256B2 (en) | 1997-07-11 | 2001-07-26 | Smithkline Beecham Plc | Novel compounds |
| GB9801392D0 (en) * | 1998-01-22 | 1998-03-18 | Smithkline Beecham Plc | Novel compounds |
| WO2000058304A1 (en) | 1999-03-26 | 2000-10-05 | Shionogi & Co., Ltd. | Heterocyclic sulfonamide derivatives |
| AU2001250783A1 (en) | 2000-02-29 | 2001-09-12 | Cor Therapeutics, Inc. | Benzamides and related inhibitors of factor xa |
| AU2001296193B2 (en) * | 2000-10-20 | 2006-04-27 | Biovitrum Ab | 2-, 3-, 4-, or 5-substituted-N1-(benzensulfonyl)indoles and their use in therapy |
| AU2002220715A1 (en) * | 2000-11-24 | 2002-06-03 | Smithkline Beecham Plc | Indolsulfonyl compounds useful in the treatment of cns disorders |
| 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 |
| PL374401A1 (en) * | 2002-06-05 | 2005-10-17 | F.Hoffmann-La Roche Ag | 1-sulfonyl-4-aminoalkoxy indole derivatives as 5-ht6-receptor modulators for the treatment of cns-disorders |
| JP4754821B2 (ja) * | 2002-06-20 | 2011-08-24 | プロキシマゲン・リミテッド | 肥満症、ｉｉ型糖尿病およびｃｎｓ障害の治療に有用な新規化合物 |
| ES2311721T3 (es) * | 2002-09-17 | 2009-02-16 | F. Hoffmann-La Roche Ag | Indoles sustituidos en posicion 2,4 y su empleo como moduladores de 5-ht6. |
-
2003
- 2003-10-13 PL PL03376479A patent/PL376479A1/xx not_active Application Discontinuation
- 2003-10-13 CA CA002501172A patent/CA2501172A1/en not_active Abandoned
- 2003-10-13 EP EP03775181A patent/EP1556037B1/en not_active Expired - Lifetime
- 2003-10-13 DE DE60309498T patent/DE60309498T2/de not_active Expired - Lifetime
- 2003-10-13 RU RU2005115115/04A patent/RU2324693C2/ru not_active IP Right Cessation
- 2003-10-13 WO PCT/EP2003/011323 patent/WO2004035047A1/en not_active Ceased
- 2003-10-13 MX MXPA05004128A patent/MXPA05004128A/es active IP Right Grant
- 2003-10-13 KR KR1020057006683A patent/KR20050073560A/ko not_active Ceased
- 2003-10-13 JP JP2004544204A patent/JP2006505559A/ja active Pending
- 2003-10-13 CN CNB2003801014548A patent/CN1309384C/zh not_active Expired - Fee Related
- 2003-10-13 AT AT03775181T patent/ATE344030T1/de not_active IP Right Cessation
- 2003-10-13 ES ES03775181T patent/ES2274285T3/es not_active Expired - Lifetime
- 2003-10-13 AU AU2003283265A patent/AU2003283265B2/en not_active Ceased
- 2003-10-13 BR BR0315317-7A patent/BR0315317A/pt not_active IP Right Cessation
- 2003-10-14 TW TW092128412A patent/TW200418456A/zh unknown
- 2003-10-15 PA PA20038586401A patent/PA8586401A1/es unknown
- 2003-10-15 PE PE2003001052A patent/PE20040691A1/es not_active Application Discontinuation
- 2003-10-16 UY UY28026A patent/UY28026A1/es not_active Application Discontinuation
- 2003-10-16 US US10/687,091 patent/US7022708B2/en not_active Expired - Fee Related
- 2003-10-16 AR ARP030103764A patent/AR041635A1/es not_active Application Discontinuation
- 2003-10-17 GT GT200300226A patent/GT200300226A/es unknown
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