JP2007514005A - 置換テトラヒドロカルバゾールおよびシクロペンタノインドール誘導体 - Google Patents
置換テトラヒドロカルバゾールおよびシクロペンタノインドール誘導体 Download PDFInfo
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- JP2007514005A JP2007514005A JP2006548049A JP2006548049A JP2007514005A JP 2007514005 A JP2007514005 A JP 2007514005A JP 2006548049 A JP2006548049 A JP 2006548049A JP 2006548049 A JP2006548049 A JP 2006548049A JP 2007514005 A JP2007514005 A JP 2007514005A
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- compound
- methylsulfonyl
- fluoro
- tetrahydro
- ethyl
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- XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical class N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 title abstract 2
- -1 rhinitis Chemical compound 0.000 claims abstract description 29
- 238000011282 treatment Methods 0.000 claims abstract description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 23
- 201000010099 disease Diseases 0.000 claims abstract description 20
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 claims abstract description 19
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 claims abstract description 19
- 208000006673 asthma Diseases 0.000 claims abstract description 13
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- 206010039083 rhinitis Diseases 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 136
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 34
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- 150000003839 salts Chemical class 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 10
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- 125000000217 alkyl group Chemical group 0.000 claims description 4
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- KSSMIJUMUAANAX-DZGCQCFKSA-N 2-[(1r)-6-fluoro-8-methylsulfonyl-9-[(1s)-1-[4-(trifluoromethyl)phenyl]ethyl]-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1([C@H](C)N2C3=C(C=C(F)C=C3C=3CCC[C@H](CC(O)=O)C=32)S(C)(=O)=O)=CC=C(C(F)(F)F)C=C1 KSSMIJUMUAANAX-DZGCQCFKSA-N 0.000 claims description 3
- KGFDNQQQBPWRCG-DZGCQCFKSA-N 2-[(1r)-6-fluoro-9-[(1s)-1-(4-fluorophenyl)ethyl]-8-methylsulfonyl-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1([C@H](C)N2C3=C(C=C(F)C=C3C=3CCC[C@H](CC(O)=O)C=32)S(C)(=O)=O)=CC=C(F)C=C1 KGFDNQQQBPWRCG-DZGCQCFKSA-N 0.000 claims description 3
- AVMJTTDTMIDNFP-DZGCQCFKSA-N 2-[(1r)-9-[(1s)-1-(3-chlorophenyl)ethyl]-6-fluoro-8-methylsulfonyl-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1([C@H](C)N2C3=C(C=C(F)C=C3C=3CCC[C@H](CC(O)=O)C=32)S(C)(=O)=O)=CC=CC(Cl)=C1 AVMJTTDTMIDNFP-DZGCQCFKSA-N 0.000 claims description 3
- XBOZNJBPJVTREM-QWHCGFSZSA-N 2-[(1r)-9-[(1s)-1-(4-chloro-2-fluorophenyl)ethyl]-6-fluoro-8-methylsulfonyl-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1([C@H](C)N2C3=C(C=C(F)C=C3C=3CCC[C@H](CC(O)=O)C=32)S(C)(=O)=O)=CC=C(Cl)C=C1F XBOZNJBPJVTREM-QWHCGFSZSA-N 0.000 claims description 3
- PZOJAPPZAXUOPF-GXTWGEPZSA-N 2-[(1r)-9-[(1s)-1-(4-chloro-3-fluorophenyl)ethyl]-6-fluoro-8-methylsulfonyl-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1([C@H](C)N2C3=C(C=C(F)C=C3C=3CCC[C@H](CC(O)=O)C=32)S(C)(=O)=O)=CC=C(Cl)C(F)=C1 PZOJAPPZAXUOPF-GXTWGEPZSA-N 0.000 claims description 3
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- IBCFVGVAMLZBIX-DZGCQCFKSA-N 2-[(1r)-9-[(1s)-1-(4-bromophenyl)ethyl]-6-fluoro-8-methylsulfonyl-1,2,3,4-tetrahydrocarbazol-1-yl]acetic acid Chemical compound C1([C@H](C)N2C3=C(C=C(F)C=C3C=3CCC[C@H](CC(O)=O)C=32)S(C)(=O)=O)=CC=C(Br)C=C1 IBCFVGVAMLZBIX-DZGCQCFKSA-N 0.000 claims description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pulmonology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Otolaryngology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53029803P | 2003-12-15 | 2003-12-15 | |
| PCT/CA2004/002123 WO2005056527A1 (en) | 2003-12-15 | 2004-12-13 | Substituted tetrahydrocarbazole and cyclopentanoindole derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007514005A true JP2007514005A (ja) | 2007-05-31 |
| JP2007514005A5 JP2007514005A5 (enExample) | 2008-01-24 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006548049A Withdrawn JP2007514005A (ja) | 2003-12-15 | 2004-12-13 | 置換テトラヒドロカルバゾールおよびシクロペンタノインドール誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7019022B2 (enExample) |
| EP (1) | EP1697322A4 (enExample) |
| JP (1) | JP2007514005A (enExample) |
| CN (1) | CN1894213A (enExample) |
| AU (1) | AU2004296910A1 (enExample) |
| CA (1) | CA2548602A1 (enExample) |
| WO (1) | WO2005056527A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008530250A (ja) * | 2005-02-17 | 2008-08-07 | メルク エンド カムパニー インコーポレーテッド | アテローム性動脈硬化症、脂質代謝異常及び関連症状の治療方法 |
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| HUE028972T2 (en) | 2011-04-14 | 2017-01-30 | Actelion Pharmaceuticals Ltd | 7- (Heteroarylamino) -6,7,8,9-tetrahydropyrido [1,2-a] indole acetic acid derivatives and their use as prostaglandin D2 receptor modulators |
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| MX2016011900A (es) | 2014-03-18 | 2016-12-05 | Actelion Pharmaceuticals Ltd | Derivados de acido azaindol-acetico y su uso como moduladores del receptor de prostaglandina d2. |
| PL3350179T3 (pl) | 2015-09-15 | 2021-08-02 | Idorsia Pharmaceuticals Ltd | Krystaliczne postacie |
| CN112362781A (zh) * | 2020-11-09 | 2021-02-12 | 河北诚信集团有限公司 | 一种甲基亚磺酸钠的含量测定方法 |
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| US4808608A (en) * | 1986-01-23 | 1989-02-28 | Merck & Co., Inc. | Tetrahydrocarbazole 1-alkanoic acids, pharmaceutical compositions and use |
| DE3768097D1 (de) * | 1986-01-23 | 1991-04-04 | Merck Frosst Canada Inc | Tetrahydrocarbazol-1-alkansaeuren. |
| CA1299577C (en) * | 1987-01-09 | 1992-04-28 | John W. Gillard | Tetrahydrocarbazole 1-alkanoic acids |
| US20010047027A1 (en) * | 2000-04-12 | 2001-11-29 | Marc Labelle | Prostaglandin D2 receptor antagonists |
| US6410583B1 (en) | 2000-07-25 | 2002-06-25 | Merck Frosst Canada & Co. | Cyclopentanoindoles, compositions containing such compounds and methods of treatment |
| AR038136A1 (es) * | 2002-01-24 | 2004-12-29 | Merck Frosst Canada Inc | Cicloalcanindoles con sustitucion con fluor composiciones que contienen estos compuestos y metodos de tratamiento |
| AR041089A1 (es) * | 2003-05-15 | 2005-05-04 | Merck & Co Inc | Procedimiento y composiciones farmaceutiicas para tratar aterosclerosis, dislipidemias y afecciones relacionadas |
| WO2004103970A1 (en) | 2003-05-20 | 2004-12-02 | Merck Frosst Canada Ltd. | Fluoro-methanesulfonyl-substituted cycloalkanoindoles and their use as prostaglandin d2 antagonists |
| ATE464048T1 (de) | 2003-08-07 | 2010-04-15 | Merck Sharp & Dohme | Behandlung von alzheimer-krankheit und verwandten zuständen |
-
2004
- 2004-12-08 US US11/007,009 patent/US7019022B2/en not_active Expired - Fee Related
- 2004-12-13 CN CNA2004800372808A patent/CN1894213A/zh active Pending
- 2004-12-13 JP JP2006548049A patent/JP2007514005A/ja not_active Withdrawn
- 2004-12-13 WO PCT/CA2004/002123 patent/WO2005056527A1/en not_active Ceased
- 2004-12-13 EP EP04802298A patent/EP1697322A4/en not_active Withdrawn
- 2004-12-13 CA CA002548602A patent/CA2548602A1/en not_active Abandoned
- 2004-12-13 AU AU2004296910A patent/AU2004296910A1/en not_active Abandoned
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008530250A (ja) * | 2005-02-17 | 2008-08-07 | メルク エンド カムパニー インコーポレーテッド | アテローム性動脈硬化症、脂質代謝異常及び関連症状の治療方法 |
| JP2013522355A (ja) * | 2010-03-22 | 2013-06-13 | アクテリオン ファーマシューティカルズ リミテッド | ３−（ヘテロアリール−アミノ）−１，２，３，４−テトラヒドロ−９ｈ−カルバゾール誘導体及びプロスタグランジンｄ２受容体調節剤としてのそれらの使用 |
| JP2018508560A (ja) * | 2015-03-19 | 2018-03-29 | 中国科学院上海薬物研究所Ｓｈａｎｇｈａｉ Ｉｎｓｔｉｔｕｔｅ Ｏｆ Ｍａｔｅｒｉａ Ｍｅｄｉｃａ， Ｃｈｉｎｅｓｅ Ａｃａｄｅｍｙ Ｏｆ Ｓｃｉｅｎｃｅｓ | 三環類似体、その製造方法及び使用 |
Also Published As
| Publication number | Publication date |
|---|---|
| US7019022B2 (en) | 2006-03-28 |
| EP1697322A1 (en) | 2006-09-06 |
| CA2548602A1 (en) | 2005-06-23 |
| CN1894213A (zh) | 2007-01-10 |
| AU2004296910A1 (en) | 2005-06-23 |
| WO2005056527A1 (en) | 2005-06-23 |
| EP1697322A4 (en) | 2007-12-26 |
| US20050154044A1 (en) | 2005-07-14 |
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