JP2008526936A - 置換インドールの新規製造方法 - Google Patents
置換インドールの新規製造方法 Download PDFInfo
- Publication number
- JP2008526936A JP2008526936A JP2007550831A JP2007550831A JP2008526936A JP 2008526936 A JP2008526936 A JP 2008526936A JP 2007550831 A JP2007550831 A JP 2007550831A JP 2007550831 A JP2007550831 A JP 2007550831A JP 2008526936 A JP2008526936 A JP 2008526936A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- methyl
- acetic acid
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000002475 indoles Chemical class 0.000 title abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 109
- 150000001875 compounds Chemical class 0.000 claims description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 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
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- -1 alkali metal hydroxide salt Chemical class 0.000 claims description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 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
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000010306 acid treatment Methods 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 238000010640 amide synthesis reaction Methods 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 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000725 suspension Substances 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
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 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
- 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 5
- 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 5
- 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 5
- TVNBAQZHXUWABF-UHFFFAOYSA-N ethyl 2-(2-methyl-4-nitroindol-1-yl)acetate Chemical compound C1=CC=C2N(CC(=O)OCC)C(C)=CC2=C1[N+]([O-])=O TVNBAQZHXUWABF-UHFFFAOYSA-N 0.000 description 5
- 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 5
- NJAHLZZJVRKNSE-UHFFFAOYSA-N ethyl 2-[4-acetamido-3-(4-chlorophenyl)sulfanyl-2-methylindol-1-yl]acetate Chemical compound C12=C(NC(C)=O)C=CC=C2N(CC(=O)OCC)C(C)=C1SC1=CC=C(Cl)C=C1 NJAHLZZJVRKNSE-UHFFFAOYSA-N 0.000 description 5
- 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
- 239000002585 base Substances 0.000 description 4
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 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
- 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 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 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
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 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 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VYDINPVJZJGDHQ-UHFFFAOYSA-N CCOC(C[n]1c2cccc(NC(C)=O)c2cc1C)=O Chemical compound CCOC(C[n]1c2cccc(NC(C)=O)c2cc1C)=O VYDINPVJZJGDHQ-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
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- LDZKOYVHUNPHTM-UHFFFAOYSA-N ethyl 2-(4-amino-2-methylindol-1-yl)acetate Chemical compound C1=CC=C2N(CC(=O)OCC)C(C)=CC2=C1N LDZKOYVHUNPHTM-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- FPWNLURCHDRMHC-UHFFFAOYSA-N 4-chlorobiphenyl Chemical group C1=CC(Cl)=CC=C1C1=CC=CC=C1 FPWNLURCHDRMHC-UHFFFAOYSA-N 0.000 description 1
- 0 CC(Nc1c(cc(C)[n]2CC(O*)=O)c2ccc1)=O Chemical compound CC(Nc1c(cc(C)[n]2CC(O*)=O)c2ccc1)=O 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 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
- 239000012345 acetylating agent Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 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
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 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
- 239000000543 intermediate Substances 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
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000005406 washing Methods 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)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0500604.4A GB0500604D0 (en) | 2005-01-13 | 2005-01-13 | Novel process |
| PCT/GB2006/000060 WO2006075139A2 (en) | 2005-01-13 | 2006-01-09 | Novel process for the preparation of substituted indoles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008526936A true JP2008526936A (ja) | 2008-07-24 |
| JP2008526936A5 JP2008526936A5 (https=) | 2009-02-12 |
Family
ID=34203986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007550831A Pending JP2008526936A (ja) | 2005-01-13 | 2006-01-09 | 置換インドールの新規製造方法 |
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=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012532186A (ja) * | 2009-07-06 | 2012-12-13 | アストラゼネカ・アクチエボラーグ | ４−（アセチルアミノ））−３−［（４−クロロ−フェニル）チオ］−２−メチル−１ｈ−インドール−１−酢酸の製造のための中間体および方法 |
Families Citing this family (9)
| 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 |
| CN101454284A (zh) * | 2006-05-26 | 2009-06-10 | 阿斯利康(瑞典)有限公司 | 联芳基或芳基-杂芳基取代的吲哚类化合物 |
| EP2790696A1 (en) | 2011-12-16 | 2014-10-22 | Atopix Therapeutics Limited | 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 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003013510A1 (en) * | 2001-08-07 | 2003-02-20 | Smithkline Beecham P.L.C. | 3-arylsulfonyl-7-piperazinyl- indoles, -benzofurans and -benzothiophenes with 5-ht6 receptor affinity for treating cns disorders |
| 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 |
| WO2004106302A1 (en) * | 2003-05-27 | 2004-12-09 | Astrazeneca Ab | Novel substituted 3-sulfur indoles |
Family Cites Families (34)
| 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. |
| HUT74614A (en) | 1993-02-24 | 1997-01-28 | Merck & Co Inc | Nindol derivates suitable for treatment of infection by hiv and pharmaceutical compositions containing them |
| 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 |
| AR017256A1 (es) | 1997-08-21 | 2001-09-05 | American Home Prod | Compuestos de indol sustituidos, metodo para la sintesis en fase solida de los mismos, conjuntos de combinacion para ser empleados en dicho metodo, uso delos compuestos para preparar un medicamento y composiciones farmaceuticas que los comprenden |
| DE69814012T2 (de) | 1997-12-19 | 2004-04-01 | Eli Lilly And Co., Indianapolis | Hypoglykàmische imidazoline derivate |
| 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 |
| AU7962200A (en) | 1999-10-29 | 2001-05-14 | Wakunaga Pharmaceutical Co., Ltd | Novel indole derivatives and drugs containing the same as the active ingredient |
| OA12514A (en) | 1999-12-24 | 2006-05-29 | Aventis Pharma Ltd | Azaindoles. |
| NZ522074A (en) | 2000-05-31 | 2004-06-25 | 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 |
| TWI317634B (en) * | 2001-12-13 | 2009-12-01 | Nat Health Research Institutes | Aroyl indoles compounds |
| CA2473803A1 (en) | 2002-02-01 | 2003-08-07 | Robert Greenhouse | Substituted indoles as alpha-1 agonists |
| SE0200411D0 (sv) | 2002-02-05 | 2002-02-05 | Astrazeneca Ab | Novel use |
| SE0200356D0 (sv) | 2002-02-05 | 2002-02-05 | Astrazeneca Ab | Novel use |
| EP2423190A1 (en) | 2002-05-16 | 2012-02-29 | Shionogi&Co., Ltd. | Compounds 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 |
| SE0302232D0 (sv) | 2003-08-18 | 2003-08-18 | Astrazeneca Ab | Novel Compounds |
| AU2004283139A1 (en) | 2003-10-14 | 2005-05-06 | 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 |
| CN101454284A (zh) * | 2006-05-26 | 2009-06-10 | 阿斯利康(瑞典)有限公司 | 联芳基或芳基-杂芳基取代的吲哚类化合物 |
| CA2654026A1 (en) | 2006-06-08 | 2007-12-13 | Neurokey A/S | Use of cannabinoid receptor agonists as hypothermia inducing drugs for the treatment of ischemia |
| KR20090023645A (ko) | 2006-06-28 | 2009-03-05 | 사노피-아벤티스 | 신규한 ｃｘｃｒ2 억제제 |
-
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 WO PCT/GB2006/000060 patent/WO2006075139A2/en not_active Ceased
- 2006-01-09 AU AU2006205697A patent/AU2006205697B2/en not_active Ceased
- 2006-01-09 JP JP2007550831A patent/JP2008526936A/ja active Pending
- 2006-01-09 NZ NZ556147A patent/NZ556147A/en not_active IP Right Cessation
- 2006-01-09 CA CA002594391A patent/CA2594391A1/en not_active Abandoned
- 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 US US11/813,816 patent/US7781598B2/en not_active Expired - Fee Related
- 2006-01-09 MX MX2007008348A patent/MX2007008348A/es active IP Right Grant
-
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
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003013510A1 (en) * | 2001-08-07 | 2003-02-20 | Smithkline Beecham P.L.C. | 3-arylsulfonyl-7-piperazinyl- indoles, -benzofurans and -benzothiophenes with 5-ht6 receptor affinity for treating cns disorders |
| 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 |
| WO2004106302A1 (en) * | 2003-05-27 | 2004-12-09 | Astrazeneca Ab | Novel substituted 3-sulfur indoles |
Non-Patent Citations (2)
| Title |
|---|
| JPN6012011130; 日本化学会 編: 新実験化学講座１４ 有機化合物の合成と反応ＩＩ , 1977, ｐ．９３５, 丸善株式会社 * |
| JPN6012011131; 大河原信 他編: 合成試薬 , 1980, ｐ．２４８, 株式会社 講談社 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012532186A (ja) * | 2009-07-06 | 2012-12-13 | アストラゼネカ・アクチエボラーグ | ４−（アセチルアミノ））−３−［（４−クロロ−フェニル）チオ］−２−メチル−１ｈ−インドール−１−酢酸の製造のための中間体および方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20080051586A1 (en) | 2008-02-28 |
| US7781598B2 (en) | 2010-08-24 |
| WO2006075139A3 (en) | 2006-10-19 |
| IL183965A0 (en) | 2007-10-31 |
| CA2594391A1 (en) | 2006-07-20 |
| ZA200705216B (en) | 2008-09-25 |
| NO20074047L (no) | 2007-08-06 |
| NZ556147A (en) | 2010-01-29 |
| CN101102999A (zh) | 2008-01-09 |
| WO2006075139A2 (en) | 2006-07-20 |
| AU2006205697B2 (en) | 2009-01-22 |
| MX2007008348A (es) | 2007-08-03 |
| KR20070104350A (ko) | 2007-10-25 |
| EP1844012A2 (en) | 2007-10-17 |
| BRPI0606639A2 (pt) | 2009-07-07 |
| AU2006205697A1 (en) | 2006-07-20 |
| GB0500604D0 (en) | 2005-02-16 |
| CN101102999B (zh) | 2010-12-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2008526936A (ja) | 置換インドールの新規製造方法 | |
| JP2004518737A (ja) | ２−（４−クロロベンゾイルアミノ）−３−［２（１ｈ）−キノールリノン−４−イル］プロピオン酸の製造方法 | |
| US6706890B2 (en) | Method for producing oxindoles | |
| JP2682705B2 (ja) | ２，６−ジクロロフェニルアミノベンゼン酢酸誘導体及びジフェニルアミン誘導体の製造方法。 | |
| AU735516B2 (en) | Process for preparing 4-substituted-1H-indole-3-glyoxamides | |
| DE69608862T2 (de) | Verfahren zur Herstellung einer optisch aktiven 2-Hydroxy-4-Arylbuttersäure oder deren Ester und Zwischenprodukt dafür | |
| WO2012165607A1 (ja) | プロリン化合物の製造方法 | |
| EP2349998B1 (en) | A novel process for the preparation of eletriptan | |
| JPH0978277A (ja) | ３−アミノ−２−ヒドロキシ−１，１，１−トリフルオロメチル化合物の製造法 | |
| KR20120101553A (ko) | 갑상선 호르몬 및 그것의 염의 제조 방법 | |
| RU2429235C2 (ru) | Способ получения замещенных бензофуран-5,6-дикарбонитрилов | |
| CH648828A5 (fr) | 7-acylindoles et leur utilisation pour la preparation de 7-acylindoline-2-ones. | |
| HU199414B (en) | Process for producing substituted indolinone derivatives | |
| US4550165A (en) | Process for producing 1,2,5,6-tetrahydro-4H-pyrrolo-[3,2,1-ij]-quinolin-4-one | |
| SK13592001A3 (sk) | Syntéza 3-amino-3-arylpropanoátov | |
| US4595755A (en) | 5-halo-1,2,3-(1,2-dihydropyrrolo)-4-quinolones | |
| JP3832980B2 (ja) | 殺虫活性を有するテトラヒドロフラニル誘導体の新規製造中間体 | |
| JPH10195064A (ja) | ５−アミノ−１，２，４−チアジアゾール酢酸誘導体（シン異性体）の製造方法 | |
| JP4937442B2 (ja) | ５−フルオロオキシインドールの製造法 | |
| FR2790472A1 (fr) | Derives de cyclobutene-3, 4-dione, leur preparation et leur application en therapeutique | |
| KR100522392B1 (ko) | 그라니세트론 염산염의 제조 방법 | |
| KR101059275B1 (ko) | 개선된 4-[2-(디-엔-프로필아미노)에틸]-1,3-디하이드로-2에이치-인돌-2-온의 제조 방법 | |
| JP3037399B2 (ja) | イミダゾール誘導体の製法 | |
| JPH0432064B2 (https=) | ||
| JPS6210062A (ja) | 置換されたインドリン類の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20081219 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20081219 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120306 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120605 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130122 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20130709 |