ZA200307966B - Substituted benzofuran-2-carboxamides derivatives. - Google Patents
Substituted benzofuran-2-carboxamides derivatives. Download PDFInfo
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- ZA200307966B ZA200307966B ZA200307966A ZA200307966A ZA200307966B ZA 200307966 B ZA200307966 B ZA 200307966B ZA 200307966 A ZA200307966 A ZA 200307966A ZA 200307966 A ZA200307966 A ZA 200307966A ZA 200307966 B ZA200307966 B ZA 200307966B
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- South Africa
- Prior art keywords
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- group
- compounds
- cyano
- butyl
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- QHKJIJXBJCOABP-UHFFFAOYSA-N 1-benzofuran-2-carboxamide Chemical class C1=CC=C2OC(C(=O)N)=CC2=C1 QHKJIJXBJCOABP-UHFFFAOYSA-N 0.000 title claims description 3
- -1 amino, hydroxyl Chemical group 0.000 claims description 123
- 150000001875 compounds Chemical class 0.000 claims description 78
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 239000012453 solvate Substances 0.000 claims description 24
- 208000002193 Pain Diseases 0.000 claims description 22
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
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- 238000002360 preparation method Methods 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 102000005962 receptors Human genes 0.000 claims description 8
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- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- MYAKFFVIELATHX-UHFFFAOYSA-N 5-[4-[4-(5-cyano-1h-indol-3-yl)butyl]piperazin-1-yl]-n-(2-methoxyethyl)-1-benzofuran-2-carboxamide Chemical compound C1=C(C#N)C=C2C(CCCCN3CCN(CC3)C=3C=C4C=C(OC4=CC=3)C(=O)NCCOC)=CNC2=C1 MYAKFFVIELATHX-UHFFFAOYSA-N 0.000 claims description 2
- HUWZYZLPJDXZNB-UHFFFAOYSA-N 5-[4-[4-(5-cyano-1h-indol-3-yl)butyl]piperazin-1-yl]-n-(pyridin-2-ylmethyl)-1-benzofuran-2-carboxamide Chemical compound C=1C2=CC(N3CCN(CCCCC=4C5=CC(=CC=C5NC=4)C#N)CC3)=CC=C2OC=1C(=O)NCC1=CC=CC=N1 HUWZYZLPJDXZNB-UHFFFAOYSA-N 0.000 claims description 2
- LJEHRCRLSYHWNX-UHFFFAOYSA-N 5-[4-[4-(5-cyano-1h-indol-3-yl)butyl]piperazin-1-yl]-n-(pyridin-4-ylmethyl)-1-benzofuran-2-carboxamide Chemical compound C=1C2=CC(N3CCN(CCCCC=4C5=CC(=CC=C5NC=4)C#N)CC3)=CC=C2OC=1C(=O)NCC1=CC=NC=C1 LJEHRCRLSYHWNX-UHFFFAOYSA-N 0.000 claims description 2
- UXOBIZYQXZQIAM-UHFFFAOYSA-N 5-[4-[4-(5-cyano-1h-indol-3-yl)butyl]piperazin-1-yl]-n-[2-(methylamino)ethyl]-1-benzofuran-2-carboxamide Chemical compound C1=C(C#N)C=C2C(CCCCN3CCN(CC3)C=3C=C4C=C(OC4=CC=3)C(=O)NCCNC)=CNC2=C1 UXOBIZYQXZQIAM-UHFFFAOYSA-N 0.000 claims description 2
- YAZLYSGMWBANFD-UHFFFAOYSA-N 5-[4-[4-(5-cyano-1h-indol-3-yl)butyl]piperazin-1-yl]-n-[3-(methylamino)propyl]-1-benzofuran-2-carboxamide Chemical compound C1=C(C#N)C=C2C(CCCCN3CCN(CC3)C=3C=C4C=C(OC4=CC=3)C(=O)NCCCNC)=CNC2=C1 YAZLYSGMWBANFD-UHFFFAOYSA-N 0.000 claims description 2
- TUDWAQMURNLLNT-UHFFFAOYSA-N n-(2-amino-2-oxoethyl)-5-[4-[4-(5-cyano-1h-indol-3-yl)butyl]piperazin-1-yl]-1-benzofuran-2-carboxamide Chemical compound C1=C(C#N)C=C2C(CCCCN3CCN(CC3)C=3C=C4C=C(OC4=CC=3)C(=O)NCC(=O)N)=CNC2=C1 TUDWAQMURNLLNT-UHFFFAOYSA-N 0.000 claims description 2
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- 230000003042 antagnostic effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
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- 150000001412 amines Chemical class 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
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- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
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Classifications
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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Landscapes
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- Gynecology & Obstetrics (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10112151A DE10112151A1 (de) | 2001-03-14 | 2001-03-14 | Substituierte Benzofuran-2-carbonsäureamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200307966B true ZA200307966B (en) | 2005-01-13 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200307966A ZA200307966B (en) | 2001-03-14 | 2003-10-13 | Substituted benzofuran-2-carboxamides derivatives. |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US7244846B2 (es) |
| EP (1) | EP1368346A1 (es) |
| JP (1) | JP4485743B2 (es) |
| KR (1) | KR20030080083A (es) |
| CN (1) | CN1244578C (es) |
| AR (1) | AR035782A1 (es) |
| BR (1) | BR0208040A (es) |
| CA (1) | CA2440726C (es) |
| CZ (1) | CZ20032712A3 (es) |
| DE (1) | DE10112151A1 (es) |
| EC (1) | ECSP034798A (es) |
| EE (1) | EE200300447A (es) |
| HU (1) | HUP0303449A3 (es) |
| IL (1) | IL157889A0 (es) |
| MX (1) | MXPA03008140A (es) |
| PL (1) | PL362844A1 (es) |
| RU (1) | RU2003129057A (es) |
| SK (1) | SK12492003A3 (es) |
| WO (1) | WO2002083666A1 (es) |
| ZA (1) | ZA200307966B (es) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10259244A1 (de) * | 2002-12-17 | 2004-07-01 | Merck Patent Gmbh | N-(Indolethyl-)cycloamin-Verbindungen |
| DE10305739A1 (de) * | 2003-02-11 | 2004-08-19 | Merck Patent Gmbh | Benzofuranderivate |
| DE10306941A1 (de) * | 2003-02-18 | 2004-08-26 | Merck Patent Gmbh | Benzofuranoxyethylamine |
| DE10326939A1 (de) * | 2003-06-16 | 2005-01-05 | Merck Patent Gmbh | Indol-Derivate |
| DE10326940A1 (de) * | 2003-06-16 | 2005-01-05 | Merck Patent Gmbh | Indol-Derivate |
| PE20060373A1 (es) | 2004-06-24 | 2006-04-29 | Smithkline Beecham Corp | Derivados 3-piperidinil-7-carboxamida-indazol como inhibidores de la actividad cinasa de ikk2 |
| PE20060748A1 (es) | 2004-09-21 | 2006-10-01 | Smithkline Beecham Corp | Derivados de indolcarboxamida como inhibidores de quinasa ikk2 |
| US8063071B2 (en) | 2007-10-31 | 2011-11-22 | GlaxoSmithKline, LLC | Chemical compounds |
| DE102006060597A1 (de) * | 2006-12-21 | 2008-06-26 | Merck Patent Gmbh | Verfahren zur Herstellung von Benzofuran-2-carboxamiden |
| PE20081889A1 (es) | 2007-03-23 | 2009-03-05 | Smithkline Beecham Corp | Indol carboxamidas como inhibidores de ikk2 |
| CA2718138A1 (en) * | 2008-03-14 | 2009-09-17 | Timo Heinrich | Azaindole compounds for treatment of central nervous system disorders |
| EP2110374A1 (en) * | 2008-04-18 | 2009-10-21 | Merck Sante | Benzofurane, benzothiophene, benzothiazol derivatives as FXR modulators |
| JP2012520257A (ja) | 2009-03-10 | 2012-09-06 | グラクソ グループ リミテッド | Ｉｋｋ２阻害剤としてのインドール誘導体 |
| EP2338873A1 (en) | 2009-12-22 | 2011-06-29 | Gmeiner, Peter | New aminotetraline derivatives |
| KR101361145B1 (ko) * | 2011-03-10 | 2014-02-12 | 한국화학연구원 | 신규한 벤조퓨란-2-카르복사미드 유도체 및 그의 ｍｃｈ 수용체-1 관련 질환에 대한 치료학적 용도 |
| CN103570698B (zh) * | 2012-08-01 | 2016-08-03 | 江苏恩华药业股份有限公司 | 用于制备维拉佐酮的化合物及其中间体和应用 |
| EP3027607B1 (en) | 2013-07-29 | 2020-08-26 | Sunshine Lake Pharma Co., Ltd. | Substituted heteroaryl compounds and methods of use thereof |
| US10316025B2 (en) | 2015-06-03 | 2019-06-11 | Sunshine Lake Pharma Co., Ltd. | Substituted piperazine compounds and methods of use and use thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4333254A1 (de) * | 1993-09-30 | 1995-04-06 | Merck Patent Gmbh | Piperidine und Piperazine |
| DE19730989A1 (de) * | 1997-07-18 | 1999-01-21 | Merck Patent Gmbh | Piperazin-Derivate |
| TW518218B (en) | 1999-05-27 | 2003-01-21 | Merck Patent Gmbh | Pharmaceutical compositions comprising 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoylbenzofuran-5-yl)piperazine or its physiologically acceptable salts for use in the treatment of sub-type anxiety disorders |
-
2001
- 2001-03-14 DE DE10112151A patent/DE10112151A1/de not_active Withdrawn
-
2002
- 2002-02-27 CZ CZ20032712A patent/CZ20032712A3/cs unknown
- 2002-02-27 CN CNB028058135A patent/CN1244578C/zh not_active Expired - Fee Related
- 2002-02-27 CA CA2440726A patent/CA2440726C/en not_active Expired - Fee Related
- 2002-02-27 SK SK1249-2003A patent/SK12492003A3/sk not_active Application Discontinuation
- 2002-02-27 IL IL15788902A patent/IL157889A0/xx unknown
- 2002-02-27 KR KR10-2003-7011886A patent/KR20030080083A/ko not_active Application Discontinuation
- 2002-02-27 EE EEP200300447A patent/EE200300447A/xx unknown
- 2002-02-27 WO PCT/EP2002/002093 patent/WO2002083666A1/en active IP Right Grant
- 2002-02-27 RU RU2003129057/04A patent/RU2003129057A/ru not_active Application Discontinuation
- 2002-02-27 PL PL02362844A patent/PL362844A1/xx unknown
- 2002-02-27 US US10/471,584 patent/US7244846B2/en not_active Expired - Fee Related
- 2002-02-27 EP EP02729940A patent/EP1368346A1/en not_active Withdrawn
- 2002-02-27 MX MXPA03008140A patent/MXPA03008140A/es unknown
- 2002-02-27 BR BR0208040-0A patent/BR0208040A/pt not_active IP Right Cessation
- 2002-02-27 JP JP2002581421A patent/JP4485743B2/ja not_active Expired - Fee Related
- 2002-02-27 HU HU0303449A patent/HUP0303449A3/hu unknown
- 2002-03-13 AR ARP020100898A patent/AR035782A1/es not_active Application Discontinuation
-
2003
- 2003-10-09 EC EC2003004798A patent/ECSP034798A/es unknown
- 2003-10-13 ZA ZA200307966A patent/ZA200307966B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CZ20032712A3 (cs) | 2004-01-14 |
| JP2004527536A (ja) | 2004-09-09 |
| RU2003129057A (ru) | 2005-04-10 |
| HUP0303449A2 (hu) | 2004-01-28 |
| CN1244578C (zh) | 2006-03-08 |
| PL362844A1 (en) | 2004-11-02 |
| EE200300447A (et) | 2003-12-15 |
| JP4485743B2 (ja) | 2010-06-23 |
| BR0208040A (pt) | 2004-02-25 |
| US20050075269A1 (en) | 2005-04-07 |
| US7244846B2 (en) | 2007-07-17 |
| CA2440726C (en) | 2011-05-17 |
| MXPA03008140A (es) | 2003-12-12 |
| SK12492003A3 (sk) | 2004-03-02 |
| ECSP034798A (es) | 2003-12-01 |
| EP1368346A1 (en) | 2003-12-10 |
| HUP0303449A3 (en) | 2005-02-28 |
| DE10112151A1 (de) | 2002-09-19 |
| WO2002083666A1 (en) | 2002-10-24 |
| AR035782A1 (es) | 2004-07-14 |
| KR20030080083A (ko) | 2003-10-10 |
| CN1494543A (zh) | 2004-05-05 |
| CA2440726A1 (en) | 2002-10-24 |
| IL157889A0 (en) | 2004-03-28 |
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