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 PDF

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Publication number: JP2007514005A
Authority: JP; Japan
Prior art keywords: compound; methylsulfonyl; fluoro; tetrahydro; ethyl
Prior art date: 2003-12-15
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

JP2006548049A

Other languages

English (en)

Japanese (ja)

Other versions

JP2007514005A5 (2

Inventor

ボリュー，クリスタン

グアイ，ダニエル

ワン，ザオイン

ザンボニ，ロバート

Original Assignee

メルクフロストカナダアンドカンパニー

Priority date (The priority date 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 date listed.)

2003-12-15

Filing date

2004-12-13

Publication date

2007-05-31

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=34676897&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=JP2007514005(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2004-12-13 Application filed by メルクフロストカナダアンドカンパニー filed Critical メルクフロストカナダアンドカンパニー

2007-05-31 Publication of JP2007514005A publication Critical patent/JP2007514005A/ja

2008-01-24 Publication of JP2007514005A5 publication Critical patent/JP2007514005A5/ja

Status Withdrawn legal-status Critical Current

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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
206010028735 Nasal congestion Diseases 0.000 claims abstract description 11
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
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
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
230000002265 prevention Effects 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
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
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 2
AIULETPMIOZKLN-GOEBONIOSA-N 2-[(1r)-6-fluoro-8-methylsulfonyl-9-[(1s)-1-phenylethyl]-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=C1 AIULETPMIOZKLN-GOEBONIOSA-N 0.000 claims description 2
RISLJJMLXCMMAD-GXTWGEPZSA-N 2-[(1r)-9-[(1s)-1-(3,4-dichlorophenyl)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(Cl)=C1 RISLJJMLXCMMAD-GXTWGEPZSA-N 0.000 claims description 2
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
UZGOIKLVDRHFFW-WMLDXEAASA-N 2-[(1r)-9-[(1s)-1-(4-cyanophenyl)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(C#N)C=C1 UZGOIKLVDRHFFW-WMLDXEAASA-N 0.000 claims description 2
125000004093 cyano group Chemical group *C#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

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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)

JP2006548049A 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 Withdrawn JP2007514005A (ja)

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US53029803P	2003-12-15	2003-12-15
PCT/CA2004/002123 WO2005056527A1 (en)	2003-12-15	2004-12-13	Substituted tetrahydrocarbazole and cyclopentanoindole derivatives

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US (1)	US7019022B2 (2)
EP (1)	EP1697322A4 (2)
JP (1)	JP2007514005A (2)
CN (1)	CN1894213A (2)
AU (1)	AU2004296910A1 (2)
CA (1)	CA2548602A1 (2)
WO (1)	WO2005056527A1 (2)

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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ＳｈａｎｇｈａｉＩｎｓｔｉｔｕｔｅＯｆＭａｔｅｒｉａＭｅｄｉｃａ，ＣｈｉｎｅｓｅＡｃａｄｅｍｙＯｆＳｃｉｅｎｃｅｓ	三環類似体、その製造方法及び使用

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AR041089A1 (es) *	2003-05-15	2005-05-04	Merck & Co Inc	Procedimiento y composiciones farmaceutiicas para tratar aterosclerosis, dislipidemias y afecciones relacionadas
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JP5064219B2 (ja)	2005-07-22	2012-10-31	塩野義製薬株式会社	Ｐｇｄ２受容体アンタゴニスト活性を有するアザインドール酸誘導体
EP2397476A3 (en)	2005-07-22	2011-12-28	Shionogi & Co., Ltd.	Indole derivative having PGD2 receptor antagonist activity
US8143285B2 (en)	2005-09-06	2012-03-27	Shionogi & Co., Ltd.	Indolecarboxylic acid derivative having PGD2 receptor antagonistic activity
US20090069275A1 (en) *	2006-02-17	2009-03-12	Rocca Jose G	Low flush niacin formulation
BRPI0715179A2 (pt)	2006-08-07	2013-06-11	Actelion Pharmaceuticals Ltd	composto, composiÇço farmacÊutica e uso de um composto
WO2008039882A1 (en) *	2006-09-30	2008-04-03	Sanofi-Aventis U.S. Llc	A combination of niacin and a prostaglandin d2 receptor antagonist
UA98777C2 (en)	2006-11-20	2012-06-25	Эли Лилли Энд Компани	Tetrahydrocyclopenta[b]indole compounds as androgen receptor modulators
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2004
- 2004-12-08 US US11/007,009 patent/US7019022B2/en not_active Expired - Fee Related
- 2004-12-13 WO PCT/CA2004/002123 patent/WO2005056527A1/en not_active Ceased
- 2004-12-13 AU AU2004296910A patent/AU2004296910A1/en not_active Abandoned
- 2004-12-13 EP EP04802298A patent/EP1697322A4/en not_active Withdrawn
- 2004-12-13 CN CNA2004800372808A patent/CN1894213A/zh active Pending
- 2004-12-13 JP JP2006548049A patent/JP2007514005A/ja not_active Withdrawn
- 2004-12-13 CA CA002548602A patent/CA2548602A1/en not_active Abandoned

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JP2018508560A (ja) *	2015-03-19	2018-03-29	中国科学院上海薬物研究所ＳｈａｎｇｈａｉＩｎｓｔｉｔｕｔｅＯｆＭａｔｅｒｉａＭｅｄｉｃａ，ＣｈｉｎｅｓｅＡｃａｄｅｍｙＯｆＳｃｉｅｎｃｅｓ	三環類似体、その製造方法及び使用

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US7019022B2 (en)	2006-03-28
CA2548602A1 (en)	2005-06-23
WO2005056527A1 (en)	2005-06-23
EP1697322A1 (en)	2006-09-06
CN1894213A (zh)	2007-01-10
EP1697322A4 (en)	2007-12-26
US20050154044A1 (en)	2005-07-14
AU2004296910A1 (en)	2005-06-23

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Publication	Publication Date	Title
JP2007514005A (ja)	2007-05-31	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
JP4008885B2 (ja)	2007-11-14	フルオロ置換シクロアルカノインドール及びそのプロスタグランジンｄ２受容体拮抗薬としての使用
AU2003202343A1 (en)	2003-09-18	Fluoro substituted cycloalkanoindoles and their use as prostaglandin D2 receptor antagonists
JP2006528938A (ja)	2006-12-28	フルオロ−メタンスルホニル置換シクロアルカノインドール、およびプロスタグランジンｄ２アンタゴニストとしてのこれらの使用
JP2006527205A (ja)	2006-11-30	Ｄｐ受容体拮抗物質としてのシクロアルカンピロロピリジン
AU2007203428B2 (en)	2010-04-29	Fluoro substituted cycloalkanoindoles and their use as prostaglandin D2 receptor antagonists
HK1148278A (en)	2011-09-02	Fluoro substituted cycloalkanoindoles, compositions containing such compounds and methods of treatment

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

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