CA2594391A1 - Process for the preparation of substituted indoles - Google Patents
Process for the preparation of substituted indoles Download PDFInfo
- Publication number
- CA2594391A1 CA2594391A1 CA002594391A CA2594391A CA2594391A1 CA 2594391 A1 CA2594391 A1 CA 2594391A1 CA 002594391 A CA002594391 A CA 002594391A CA 2594391 A CA2594391 A CA 2594391A CA 2594391 A1 CA2594391 A1 CA 2594391A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- process according
- methyl
- chloro
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 150000002475 indoles Chemical class 0.000 title abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 110
- 150000001875 compounds Chemical class 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 150000002148 esters Chemical group 0.000 claims description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 238000010640 amide synthesis reaction Methods 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims description 2
- 238000010306 acid treatment Methods 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 2
- 229940124597 therapeutic agent Drugs 0.000 abstract description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000007787 solid Substances 0.000 description 20
- 238000003756 stirring Methods 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 10
- 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 description 8
- UBHRJZOTFQBWLT-UHFFFAOYSA-N 2-(2-methyl-4-nitroindol-1-yl)acetic acid Chemical compound C1=CC=C2N(CC(O)=O)C(C)=CC2=C1[N+]([O-])=O UBHRJZOTFQBWLT-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- 229950009390 symclosene Drugs 0.000 description 7
- SFVJZPNQBKUOCO-UHFFFAOYSA-N 2-(4-acetamido-2-methylindol-1-yl)acetic acid Chemical compound CC(=O)NC1=CC=CC2=C1C=C(C)N2CC(O)=O SFVJZPNQBKUOCO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000012265 solid product Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- ZIXXRXGPBFMPFD-UHFFFAOYSA-N 1-chloro-4-[(4-chlorophenyl)disulfanyl]benzene Chemical compound C1=CC(Cl)=CC=C1SSC1=CC=C(Cl)C=C1 ZIXXRXGPBFMPFD-UHFFFAOYSA-N 0.000 description 4
- JWYIGNODXSRKGP-UHFFFAOYSA-N 2-[4-acetamido-3-(4-chlorophenyl)sulfanyl-2-methylindol-1-yl]acetic acid Chemical compound C1=2C(NC(=O)C)=CC=CC=2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 JWYIGNODXSRKGP-UHFFFAOYSA-N 0.000 description 4
- SHTVHNWTKBEJOB-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfanyl-2-methyl-4-nitro-1h-indole Chemical compound CC=1NC2=CC=CC([N+]([O-])=O)=C2C=1SC1=CC=C(Cl)C=C1 SHTVHNWTKBEJOB-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
- 239000012346 acetyl chloride Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- NKYAYPFWGYJSBF-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)sulfanyl-2-methyl-4-nitroindol-1-yl]acetic acid Chemical compound C12=C([N+]([O-])=O)C=CC=C2N(CC(O)=O)C(C)=C1SC1=CC=C(Cl)C=C1 NKYAYPFWGYJSBF-UHFFFAOYSA-N 0.000 description 3
- HCISKOUSZIJNET-UHFFFAOYSA-N 2-methyl-4-nitro-1h-indole Chemical compound C1=CC=C2NC(C)=CC2=C1[N+]([O-])=O HCISKOUSZIJNET-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- MASGOWOGAAXZMY-UHFFFAOYSA-N 2-(4-amino-2-methylindol-1-yl)acetic acid Chemical compound C1=CC=C2N(CC(O)=O)C(C)=CC2=C1N MASGOWOGAAXZMY-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 241000694440 Colpidium aqueous Species 0.000 description 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FSNCEEGOMTYXKY-JTQLQIEISA-N Lycoperodine 1 Natural products N1C2=CC=CC=C2C2=C1CN[C@H](C(=O)O)C2 FSNCEEGOMTYXKY-JTQLQIEISA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000012345 acetylating agent Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- XVHFFLZJOYIKFT-UHFFFAOYSA-N ethyl 2-[3-(4-chlorophenyl)sulfanyl-2-methyl-4-nitroindol-1-yl]acetate Chemical compound C12=C([N+]([O-])=O)C=CC=C2N(CC(=O)OCC)C(C)=C1SC1=CC=C(Cl)C=C1 XVHFFLZJOYIKFT-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- WQJFIWXYPKYBTO-UHFFFAOYSA-N indole-1-acetic acid Chemical compound C1=CC=C2N(CC(=O)O)C=CC2=C1 WQJFIWXYPKYBTO-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0500604.4A GB0500604D0 (en) | 2005-01-13 | 2005-01-13 | Novel process |
| GB0500604.4 | 2005-01-13 | ||
| PCT/GB2006/000060 WO2006075139A2 (en) | 2005-01-13 | 2006-01-09 | Novel process for the preparation of substituted indoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2594391A1 true CA2594391A1 (en) | 2006-07-20 |
Family
ID=34203986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002594391A Abandoned CA2594391A1 (en) | 2005-01-13 | 2006-01-09 | Process for the preparation of substituted indoles |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7781598B2 (https=) |
| EP (1) | EP1844012A2 (https=) |
| JP (1) | JP2008526936A (https=) |
| KR (1) | KR20070104350A (https=) |
| CN (1) | CN101102999B (https=) |
| AU (1) | AU2006205697B2 (https=) |
| BR (1) | BRPI0606639A2 (https=) |
| CA (1) | CA2594391A1 (https=) |
| GB (1) | GB0500604D0 (https=) |
| IL (1) | IL183965A0 (https=) |
| MX (1) | MX2007008348A (https=) |
| NO (1) | NO20074047L (https=) |
| NZ (1) | NZ556147A (https=) |
| WO (1) | WO2006075139A2 (https=) |
| ZA (1) | ZA200705216B (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200307542A (en) * | 2002-05-30 | 2003-12-16 | Astrazeneca Ab | Novel compounds |
| SE0202241D0 (sv) * | 2002-07-17 | 2002-07-17 | Astrazeneca Ab | Novel Compounds |
| SE0301569D0 (sv) * | 2003-05-27 | 2003-05-27 | Astrazeneca Ab | Novel compounds |
| SE0302232D0 (sv) * | 2003-08-18 | 2003-08-18 | Astrazeneca Ab | Novel Compounds |
| SE0303180D0 (sv) * | 2003-11-26 | 2003-11-26 | Astrazeneca Ab | Novel compounds |
| GB0500604D0 (en) | 2005-01-13 | 2005-02-16 | Astrazeneca Ab | Novel process |
| JP2009538289A (ja) * | 2006-05-26 | 2009-11-05 | アストラゼネカ・アクチエボラーグ | ビアリールまたはヘテロアリール置換インドール |
| BR112012000353B1 (pt) * | 2009-07-06 | 2020-06-02 | Astrazeneca Ab | Composto de fórmula markush, uso do composto, processos de reação com agente de acetilação e processo para preparação de um composto |
| SG11201402796SA (en) | 2011-12-16 | 2014-06-27 | Atopix Therapeutics Ltd | Combination of crth2 antagonist and a proton pump inhibitor for the treatment of eosinophilic esophagitis |
| CN103288707B (zh) * | 2013-05-28 | 2015-12-23 | 浙江大学 | 一种3-苯巯基吲哚衍生物的制备方法 |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE790679A (fr) | 1971-11-03 | 1973-04-27 | Ici Ltd | Derives de l'indole |
| JPH0615542B2 (ja) | 1986-07-22 | 1994-03-02 | 吉富製薬株式会社 | ピラゾロピリジン化合物 |
| US5095031A (en) * | 1990-08-20 | 1992-03-10 | Abbott Laboratories | Indole derivatives which inhibit leukotriene biosynthesis |
| WO1993005020A1 (en) | 1991-09-06 | 1993-03-18 | Merck & Co., Inc. | Indoles as inhibitors of hiv reverse transcriptase |
| FR2692574B1 (fr) | 1992-06-23 | 1995-06-23 | Sanofi Elf | Derives hydroxy-4 benzenethio, leur preparation ainsi que leur utilisation pour la preparation de derives aminoalkoxybenzenesulfonyles. |
| CN1119856A (zh) | 1993-02-24 | 1996-04-03 | 麦克公司 | Hiv逆转录酶抑制剂 |
| US5486525A (en) | 1993-12-16 | 1996-01-23 | Abbott Laboratories | Platelet activating factor antagonists: imidazopyridine indoles |
| US5567711A (en) * | 1995-04-19 | 1996-10-22 | Abbott Laboratories | Indole-3-carbonyl and indole-3-sulfonyl derivatives as platelet activating factor antagonists |
| TW472045B (en) | 1996-09-25 | 2002-01-11 | Astra Ab | Protein kinase C inhibitor compounds, method for their preparation, pharmaceutical composition thereof and intermediate used for their preparation |
| ZA987554B (en) | 1997-08-21 | 2000-02-21 | American Home Prod | Methods for the solid phase synthesis of substituted indole compounds. |
| EP0924209B1 (en) | 1997-12-19 | 2003-05-02 | Eli Lilly And Company | Hypoglycemic imidazoline compounds |
| US6916841B2 (en) * | 1998-02-25 | 2005-07-12 | Genetics Institute, Llc | Inhibitors of phospholipase enzymes |
| AU5886500A (en) | 1999-06-23 | 2001-01-09 | Sepracor, Inc. | Indolyl-benzimidazole antibacterials, and methods of use thereof |
| WO2001032621A1 (en) | 1999-10-29 | 2001-05-10 | Wakunaga Pharmaceutical Co., Ltd. | Novel indole derivatives and drugs containing the same as the active ingredient |
| WO2001047922A2 (en) | 1999-12-24 | 2001-07-05 | Aventis Pharma Limited | Azaindoles |
| AU2001258628A1 (en) | 2000-05-31 | 2001-12-11 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
| US6878522B2 (en) | 2000-07-07 | 2005-04-12 | Baiyong Li | Methods for the identification of compounds useful for the treatment of disease states mediated by prostaglandin D2 |
| EP1414442A1 (en) * | 2001-08-07 | 2004-05-06 | Smithkline Beecham Plc | 3-arylsulfonyl-7-piperazinyl- indoles, -benzofurans and -benzothiophenes with 5-ht6 receptor affinity for treating cns disorders |
| TWI317634B (en) * | 2001-12-13 | 2009-12-01 | Nat Health Research Institutes | Aroyl indoles compounds |
| RU2337909C2 (ru) | 2002-02-01 | 2008-11-10 | Ф.Хоффманн-Ля Рош Аг | Замещенные индолы и фармацевтическая композиция, обладающая агонистической активностью в отношении альфа-1a/l адренорецептора |
| SE0200411D0 (sv) | 2002-02-05 | 2002-02-05 | Astrazeneca Ab | Novel use |
| SE0200356D0 (sv) | 2002-02-05 | 2002-02-05 | Astrazeneca Ab | Novel use |
| AU2003231509A1 (en) | 2002-05-16 | 2003-12-02 | Shionogi And Co., Ltd. | Compound exhibiting pgd 2 receptor antagonism |
| SE0201635D0 (sv) | 2002-05-30 | 2002-05-30 | Astrazeneca Ab | Novel compounds |
| TW200307542A (en) * | 2002-05-30 | 2003-12-16 | Astrazeneca Ab | Novel compounds |
| SE0202241D0 (sv) | 2002-07-17 | 2002-07-17 | Astrazeneca Ab | Novel Compounds |
| SE0202463D0 (sv) | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | Novel compounds |
| WO2004039807A1 (en) * | 2002-10-30 | 2004-05-13 | Merck Frosst Canada & Co. | Pyridopyrrolizine and pyridoindolizine derivatives |
| WO2004050085A1 (en) * | 2002-12-03 | 2004-06-17 | F. Hoffmann-La Roche Ag | Aminoalkoxyindoles as 5-ht6-receptor ligands for the treatment of cns-disorders |
| SE0301569D0 (sv) * | 2003-05-27 | 2003-05-27 | Astrazeneca Ab | Novel compounds |
| SE0302232D0 (sv) | 2003-08-18 | 2003-08-18 | Astrazeneca Ab | Novel Compounds |
| US20070232681A1 (en) | 2003-10-14 | 2007-10-04 | Oxagen Limited | Compounds Having Crth2 Antagonist Activity |
| SE0303180D0 (sv) | 2003-11-26 | 2003-11-26 | Astrazeneca Ab | Novel compounds |
| GB0500604D0 (en) | 2005-01-13 | 2005-02-16 | Astrazeneca Ab | Novel process |
| GB2422831A (en) | 2005-02-04 | 2006-08-09 | Oxagen Ltd | Pyrrolopyridines and their use in the treatment of diseases mediated by PGD2 at the CRTH2 receptor |
| JP2009538289A (ja) | 2006-05-26 | 2009-11-05 | アストラゼネカ・アクチエボラーグ | ビアリールまたはヘテロアリール置換インドール |
| KR20090027689A (ko) | 2006-06-08 | 2009-03-17 | 뉴로키 에이/에스 | 허혈의 치료를 위한 저체온 유도제로서 카나비노이드 수용체 아고니스트의 용도 |
| CA2656150A1 (en) | 2006-06-28 | 2008-01-03 | Sanofi-Aventis | New cxcr2 inhibitors |
-
2005
- 2005-01-13 GB GBGB0500604.4A patent/GB0500604D0/en not_active Ceased
-
2006
- 2006-01-09 KR KR1020077015946A patent/KR20070104350A/ko not_active Ceased
- 2006-01-09 CN CN2006800023115A patent/CN101102999B/zh not_active Expired - Fee Related
- 2006-01-09 MX MX2007008348A patent/MX2007008348A/es active IP Right Grant
- 2006-01-09 JP JP2007550831A patent/JP2008526936A/ja active Pending
- 2006-01-09 AU AU2006205697A patent/AU2006205697B2/en not_active Ceased
- 2006-01-09 US US11/813,816 patent/US7781598B2/en not_active Expired - Fee Related
- 2006-01-09 CA CA002594391A patent/CA2594391A1/en not_active Abandoned
- 2006-01-09 WO PCT/GB2006/000060 patent/WO2006075139A2/en not_active Ceased
- 2006-01-09 BR BRPI0606639-9A patent/BRPI0606639A2/pt not_active IP Right Cessation
- 2006-01-09 EP EP06700281A patent/EP1844012A2/en not_active Withdrawn
- 2006-01-09 NZ NZ556147A patent/NZ556147A/en not_active IP Right Cessation
-
2007
- 2007-06-14 IL IL183965A patent/IL183965A0/en unknown
- 2007-06-29 ZA ZA200705216A patent/ZA200705216B/xx unknown
- 2007-08-06 NO NO20074047A patent/NO20074047L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US7781598B2 (en) | 2010-08-24 |
| GB0500604D0 (en) | 2005-02-16 |
| WO2006075139A3 (en) | 2006-10-19 |
| IL183965A0 (en) | 2007-10-31 |
| AU2006205697A1 (en) | 2006-07-20 |
| EP1844012A2 (en) | 2007-10-17 |
| KR20070104350A (ko) | 2007-10-25 |
| BRPI0606639A2 (pt) | 2009-07-07 |
| CN101102999B (zh) | 2010-12-29 |
| MX2007008348A (es) | 2007-08-03 |
| CN101102999A (zh) | 2008-01-09 |
| NO20074047L (no) | 2007-08-06 |
| JP2008526936A (ja) | 2008-07-24 |
| AU2006205697B2 (en) | 2009-01-22 |
| NZ556147A (en) | 2010-01-29 |
| WO2006075139A2 (en) | 2006-07-20 |
| US20080051586A1 (en) | 2008-02-28 |
| ZA200705216B (en) | 2008-09-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20140812 |