JP2012503664A5 - - Google Patents
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- Publication number
- JP2012503664A5 JP2012503664A5 JP2011529154A JP2011529154A JP2012503664A5 JP 2012503664 A5 JP2012503664 A5 JP 2012503664A5 JP 2011529154 A JP2011529154 A JP 2011529154A JP 2011529154 A JP2011529154 A JP 2011529154A JP 2012503664 A5 JP2012503664 A5 JP 2012503664A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- methylsulfanyl
- pyridine
- oxazol
- mmol
- 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.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- -1 2 - methylsulfanyl-oxazol-5-yl Chemical group 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- IYMYCOCMDBLWOY-JEDNCBNOSA-N (1s)-1-(2-methylsulfanyl-1,3-oxazol-5-yl)propan-1-amine;hydrochloride Chemical compound Cl.CC[C@H](N)C1=CN=C(SC)O1 IYMYCOCMDBLWOY-JEDNCBNOSA-N 0.000 description 3
- SVXOOOYHPUKMQG-UHFFFAOYSA-N 1-(4-fluorophenyl)-n-[[4-(4-methylpiperazin-1-yl)sulfonylphenyl]methyl]pyrazolo[3,4-c]pyridine-4-carboxamide Chemical compound C1CN(C)CCN1S(=O)(=O)C(C=C1)=CC=C1CNC(=O)C1=CN=CC2=C1C=NN2C1=CC=C(F)C=C1 SVXOOOYHPUKMQG-UHFFFAOYSA-N 0.000 description 3
- UEZKWPBPQQSIMH-UHFFFAOYSA-N 2-[[5-[[[1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carbonyl]amino]methyl]pyridin-2-yl]sulfonyl-methylamino]ethyl acetate Chemical compound C1=NC(S(=O)(=O)N(CCOC(C)=O)C)=CC=C1CNC(=O)C1=CN=CC2=C1C=NN2C1=CC=C(F)C=C1 UEZKWPBPQQSIMH-UHFFFAOYSA-N 0.000 description 3
- YKZYEUAXINVCEK-UHFFFAOYSA-N 2-methylsulfanyl-1,3-oxazole-5-carboxylic acid Chemical compound CSC1=NC=C(C(O)=O)O1 YKZYEUAXINVCEK-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- AQBJFVCKUVWMLP-UHFFFAOYSA-N ethyl 2-ethylsulfanyl-1,3-oxazole-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(SCC)O1 AQBJFVCKUVWMLP-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VVUSTAJOHMIPTA-NSHDSACASA-N 1-(4-fluorophenyl)-n-[(1s)-1-(2-methylsulfanyl-1,3-oxazol-5-yl)ethyl]pyrazolo[3,4-c]pyridine-4-carboxamide Chemical compound O1C(SC)=NC=C1[C@H](C)NC(=O)C1=CN=CC2=C1C=NN2C1=CC=C(F)C=C1 VVUSTAJOHMIPTA-NSHDSACASA-N 0.000 description 1
- QKDVCGNAAZDXBZ-INIZCTEOSA-N 1-(4-fluorophenyl)-n-[(1s)-1-(2-methylsulfanyl-1,3-oxazol-5-yl)propyl]pyrazolo[3,4-c]pyridine-4-carboxamide Chemical compound N([C@@H](CC)C=1OC(SC)=NC=1)C(=O)C(C=1C=N2)=CN=CC=1N2C1=CC=C(F)C=C1 QKDVCGNAAZDXBZ-INIZCTEOSA-N 0.000 description 1
- JTXOGWNTNOJMLN-UHFFFAOYSA-N 1-(4-fluorophenyl)pyrazolo[3,4-c]pyridine-4-carboxylic acid Chemical compound N1=CC=2C(C(=O)O)=CN=CC=2N1C1=CC=C(F)C=C1 JTXOGWNTNOJMLN-UHFFFAOYSA-N 0.000 description 1
- BTIDLVRPONKKEW-UHFFFAOYSA-N 2-methylsulfanyl-1,3-oxazole-4-carboxylic acid Chemical compound CSC1=NC(C(O)=O)=CO1 BTIDLVRPONKKEW-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- ZFLDTEIDAGWEEI-UHFFFAOYSA-N ethyl 2-chloro-1,3-oxazole-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(Cl)O1 ZFLDTEIDAGWEEI-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical group [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10040108P | 2008-09-26 | 2008-09-26 | |
| US61/100,401 | 2008-09-26 | ||
| PCT/US2009/057778 WO2010036632A1 (en) | 2008-09-26 | 2009-09-22 | Azaindazole compounds as ccr1 receptor antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012503664A JP2012503664A (ja) | 2012-02-09 |
| JP2012503664A5 true JP2012503664A5 (enExample) | 2012-05-24 |
| JP5507567B2 JP5507567B2 (ja) | 2014-05-28 |
Family
ID=41349302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011529154A Active JP5507567B2 (ja) | 2008-09-26 | 2009-09-22 | Ｃｃｒ１受容体拮抗薬としてのアザインダゾール化合物 |
Country Status (24)
| Country | Link |
|---|---|
| US (4) | US7879873B2 (enExample) |
| EP (1) | EP2346868B1 (enExample) |
| JP (1) | JP5507567B2 (enExample) |
| KR (1) | KR20110060904A (enExample) |
| CN (1) | CN102227425A (enExample) |
| AP (1) | AP2739A (enExample) |
| AR (1) | AR073689A1 (enExample) |
| AU (1) | AU2009296839A1 (enExample) |
| BR (1) | BRPI0919844A2 (enExample) |
| CA (1) | CA2737472A1 (enExample) |
| CL (1) | CL2011000668A1 (enExample) |
| CO (1) | CO6351735A2 (enExample) |
| EA (1) | EA201100524A1 (enExample) |
| EC (1) | ECSP11010932A (enExample) |
| IL (1) | IL210857A0 (enExample) |
| MA (1) | MA32655B1 (enExample) |
| MX (1) | MX2011002951A (enExample) |
| NZ (1) | NZ591115A (enExample) |
| PE (1) | PE20110854A1 (enExample) |
| TW (1) | TW201018683A (enExample) |
| UA (1) | UA103634C2 (enExample) |
| UY (1) | UY32140A (enExample) |
| WO (1) | WO2010036632A1 (enExample) |
| ZA (1) | ZA201100625B (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2722923C (en) | 2008-04-29 | 2016-08-02 | Boehringer Ingelheim International Gmbh | Indazole compounds as ccr1 receptor antagonists |
| CA2722811C (en) * | 2008-05-06 | 2016-07-05 | Boehringer Ingelheim International Gmbh | Pyrazole compounds as ccr1 antagonists |
| NZ591115A (en) * | 2008-09-26 | 2012-10-26 | Boehringer Ingelheim Int | Azaindazole compounds as ccr1 receptor antagonists |
| EP2408772B1 (en) * | 2009-03-19 | 2015-07-01 | Medical Research Council Technology | Compounds |
| PH12012500775A1 (en) | 2009-10-21 | 2012-11-26 | Boehringer Ingelheim Int | Indazole and pyrazolopyridine compounds as ccr1 receptor antagonists |
| US8927550B2 (en) | 2009-10-27 | 2015-01-06 | Boehringer Ingelheim International Gmbh | Heterocyclic compounds as CCR1 receptor antagonists |
| WO2011071730A1 (en) * | 2009-12-08 | 2011-06-16 | Boehringer Ingelheim International Gmbh | Process for synthesis of intermediates useful for making substituted indazole and azaindazole compounds |
| US8871786B2 (en) | 2010-04-30 | 2014-10-28 | Boehringer Ingelheim International Gmbh | Azaindazole amide compounds as CCR1 receptor antagonists |
| EP2388260A1 (de) * | 2010-05-21 | 2011-11-23 | Archimica GmbH | Herstellungsverfahren für einen Inhibitor eines Blutgerinnungsfaktors |
| EP2611804A1 (en) | 2010-09-03 | 2013-07-10 | Forma TM, LLC. | Novel compounds and compositions for the inhibition of nampt |
| WO2012087782A1 (en) | 2010-12-23 | 2012-06-28 | Boehringer Ingelheim International Gmbh | Pyrazolopiperidine compounds as ccr1 receptor antagonists |
| WO2012118812A2 (en) | 2011-02-28 | 2012-09-07 | Epizyme, Inc. | Substituted 6,5-fused bicyclic heteroaryl compounds |
| CN102775365A (zh) * | 2011-05-10 | 2012-11-14 | 无锡立诺康医药科技有限公司 | 5-氨基取代基-异噁唑类化合物或其酸式盐的合成工艺 |
| WO2012163848A1 (en) | 2011-05-27 | 2012-12-06 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for the treatment of crohn's disease |
| EP2771011A4 (en) * | 2011-10-24 | 2015-04-15 | Glaxosmithkline Ip No 2 Ltd | CHEMICAL COMPOUNDS |
| US20140329809A1 (en) | 2011-10-28 | 2014-11-06 | Galderma Research & Development | New leukocyte infiltrate markers for rosacea and uses thereof |
| JP2015508785A (ja) * | 2012-03-02 | 2015-03-23 | ジェネンテック， インコーポレイテッド | ピリジニル及びピリミジニルスルホキシド及びスルホン誘導体 |
| AR091858A1 (es) | 2012-07-25 | 2015-03-04 | Sova Pharmaceuticals Inc | INHIBIDORES DE CISTATIONIN-g-LIASA (CSE) |
| US9045477B2 (en) * | 2013-03-15 | 2015-06-02 | Epizyme, Inc. | Substituted 6,5-fused bicyclic heteroaryl compounds |
| US9776996B2 (en) * | 2013-03-15 | 2017-10-03 | Epizyme, Inc. | Substituted 6,5-fused bicyclic heteroaryl compounds |
| FR3016879A1 (fr) * | 2014-01-29 | 2015-07-31 | Guillaume Laconde | Procede de preparation de benzotriazole n-acyles |
| LT3119757T (lt) | 2014-03-17 | 2018-07-10 | Pfizer Inc. | Diacilglicerolio aciltransferazės 2 inhibitoriai, skirti panaudoti metabolinių ir susijusių ligų gydyme |
| NZ723530A (en) | 2014-04-14 | 2023-05-26 | Boehringer Ingelheim Int | Compounds as modulators of ror gamma |
| UA123219C2 (uk) | 2015-10-23 | 2021-03-03 | Віфор (Інтернаціональ) Аґ | Інгібітори феропортину |
| WO2017081310A1 (en) | 2015-11-13 | 2017-05-18 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
| US20180354921A1 (en) | 2015-11-13 | 2018-12-13 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
| ES2934785T3 (es) | 2016-03-07 | 2023-02-27 | Global Alliance For Tb Drug Development Inc | Compuestos antibacterianos y usos de los mismos |
| JOP20180036A1 (ar) | 2017-04-18 | 2019-01-30 | Vifor Int Ag | أملاح لمثبطات فروبورتين جديدة |
| TWI853814B (zh) | 2018-05-31 | 2024-09-01 | 南韓商Ｃ＆Ｃ新藥研究所 | 雜環衍生物及其用途 |
| CN111393376B (zh) * | 2020-05-11 | 2022-05-13 | 安徽赛迪生物科技有限公司 | 一种2-氯嘧啶-4-甲酸的合成方法 |
| WO2021262878A1 (en) * | 2020-06-24 | 2021-12-30 | Oregon Health & Science University | Novel molecule for modulation of innate immune responses controlled by sting protein |
Family Cites Families (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5242931A (en) | 1988-06-09 | 1993-09-07 | Kyowa Hakko Kogyo Co., Ltd. | Tricyclic compounds as TXA2 antagonists |
| US4999363A (en) | 1988-06-09 | 1991-03-12 | Kyowa Hakko Kogyo Co., Ltd. | Tricyclic compounds |
| HU225047B1 (en) | 1991-03-28 | 2006-05-29 | Eisai Co Ltd | Heterocyclic-piperidin-derivatives, pharmaceutical compositions containing them and process for their production |
| US5750542A (en) | 1993-09-28 | 1998-05-12 | Pfizer | Benzisoxazole and benzisothizole derivatives as cholinesterase inhibitors |
| US5612360A (en) | 1992-06-03 | 1997-03-18 | Eli Lilly And Company | Angiotensin II antagonists |
| BR9305569A (pt) | 1992-07-03 | 1995-12-26 | Kumiai Chemical Industry Co | Derivados heterocíclicos condensados e herbicidas |
| EP0657450B1 (en) | 1993-06-25 | 1998-09-09 | KumaiI Chemical Industry Co., Ltd. | Indazolesulfonylurea derivative, use thereof, and intermediate for production thereof |
| US6025374A (en) | 1994-12-06 | 2000-02-15 | Merck Sharp & Dohme, Ltd. | Azetidine, pyrrolidine and piperidine derivatives as 5HT1 receptor agonists |
| GB9519563D0 (en) | 1995-09-26 | 1995-11-29 | Merck Sharp & Dohme | Therapeutic agents |
| GB9523583D0 (en) | 1995-11-17 | 1996-01-17 | Merck Sharp & Dohme | Therapeutic agents |
| US5760028A (en) | 1995-12-22 | 1998-06-02 | The Dupont Merck Pharmaceutical Company | Integrin receptor antagonists |
| AU1345697A (en) | 1995-12-22 | 1997-07-17 | Du Pont Merck Pharmaceutical Company, The | Novel integrin receptor antagonists |
| JPH101478A (ja) | 1996-06-11 | 1998-01-06 | Kumiai Chem Ind Co Ltd | インダゾールスルホニル尿素誘導体及び除草剤 |
| GB9615449D0 (en) | 1996-07-23 | 1996-09-04 | Merck Sharp & Dohme | Therapeutic agents |
| WO2000077027A2 (en) | 1999-06-14 | 2000-12-21 | Tularik Limited | Serine protease inhibitors |
| IL135714A0 (en) | 1997-11-04 | 2001-05-20 | Pfizer Prod Inc | Therapeutically active compounds based on indazole bioisostere replacement of catechol in pde4 inhibitors |
| US6331640B1 (en) | 1998-10-13 | 2001-12-18 | Hoffmann-La Roche Inc. | Diaminopropionic acid derivatives |
| JP2003502314A (ja) | 1999-06-14 | 2003-01-21 | イーライ・リリー・アンド・カンパニー | 化合物 |
| WO2001000656A2 (en) | 1999-06-29 | 2001-01-04 | Ortho-Mcneil Pharmaceutical, Inc. | Novel indazole peptidomimetics as thrombin receptor antagonists |
| GB0030305D0 (en) | 2000-12-13 | 2001-01-24 | Lilly Co Eli | Compounds |
| GB0030303D0 (en) | 2000-12-13 | 2001-01-24 | Lilly Co Eli | Compounds |
| GB0030304D0 (en) | 2000-12-13 | 2001-01-24 | Lilly Co Eli | Compounds |
| GB0030306D0 (en) | 2000-12-13 | 2001-01-24 | Lilly Co Eli | Compounds |
| US6897231B2 (en) | 2000-07-31 | 2005-05-24 | Signal Pharmaceuticals, Inc. | Indazole derivatives as JNK inhibitors and compositions and methods related thereto |
| US20050009876A1 (en) | 2000-07-31 | 2005-01-13 | Bhagwat Shripad S. | Indazole compounds, compositions thereof and methods of treatment therewith |
| US7211594B2 (en) | 2000-07-31 | 2007-05-01 | Signal Pharmaceuticals, Llc | Indazole compounds and compositions thereof as JNK inhibitors and for the treatment of diseases associated therewith |
| US7058826B2 (en) * | 2000-09-27 | 2006-06-06 | Amphus, Inc. | System, architecture, and method for logical server and other network devices in a dynamically configurable multi-server network environment |
| US20020052373A1 (en) | 2000-10-26 | 2002-05-02 | Zorn Stevin H. | Combination treatment for dementia or cognitive deficits associated with alzheimer's disease and parkinson's disease |
| WO2003037274A2 (en) | 2001-11-01 | 2003-05-08 | Icagen, Inc. | Pyrazole-amides and-sulfonamides |
| WO2008011131A2 (en) | 2006-07-21 | 2008-01-24 | Takeda Pharmaceutical Company Limited | Amide compounds |
| WO2003053941A2 (en) * | 2001-12-20 | 2003-07-03 | Bristol-Myers Squibb Company | Barbituric acid derivatives as inhibitors of tnf-alpha converting enzyme (tace) and/or matrix metalloproteinases |
| ATE469142T1 (de) | 2002-04-11 | 2010-06-15 | Boehringer Ingelheim Pharma | Heterocyclische amid-derivate als cytokin- inhibitoren |
| US7429609B2 (en) | 2002-05-31 | 2008-09-30 | Eisai R & D Management Co., Ltd. | Pyrazole compound and medicinal composition containing the same |
| EP1531822B1 (en) * | 2002-06-12 | 2009-08-05 | ChemoCentryx Inc | 1-aryl-4-substituted piperazine derivatives for use as ccr1 antagonists for the treatment of inflammation and immune disorders |
| TW200500341A (en) * | 2002-11-12 | 2005-01-01 | Astrazeneca Ab | Novel compounds |
| SE0203825D0 (sv) | 2002-12-20 | 2002-12-20 | Astrazeneca Ab | Novel fused heterocycles and uses thereof |
| US7129264B2 (en) | 2003-04-16 | 2006-10-31 | Bristol-Myers Squibb Company | Biarylmethyl indolines and indoles as antithromboembolic agents |
| US20040220170A1 (en) | 2003-05-01 | 2004-11-04 | Atkinson Robert N. | Pyrazole-amides and sulfonamides as sodium channel modulators |
| ATE423122T1 (de) | 2003-08-15 | 2009-03-15 | Astrazeneca Ab | Kondensierte heterocyclen als inhibitoren von glutamatracemase (muri) |
| CA2598531A1 (en) | 2005-02-24 | 2006-08-31 | Merck & Co., Inc. | Benzazole potentiators of metabotropic glutamate receptors |
| GB0504828D0 (en) * | 2005-03-09 | 2005-04-13 | Merck Sharp & Dohme | Therapeutic agents |
| DK2444079T3 (en) | 2005-05-17 | 2017-01-30 | Sarcode Bioscience Inc | Compositions and Methods for the Treatment of Eye Diseases |
| PT1906965E (pt) * | 2005-06-22 | 2015-09-03 | Chemocentryx Inc | Compostos de azaindazol e métodos de utilização |
| AU2006287202B2 (en) | 2005-09-01 | 2013-01-24 | Eli Lilly And Company | 6-arylalkylamino- 2,3,4,5-tetrahydro-1H-benzo[d]azepines as 5-HT2c receptor agonists |
| WO2007102883A2 (en) | 2005-10-25 | 2007-09-13 | Smithkline Beecham Corporation | Chemical compounds |
| TW200829578A (en) * | 2006-11-23 | 2008-07-16 | Astrazeneca Ab | Chemical compounds 537 |
| US7968536B2 (en) * | 2007-06-29 | 2011-06-28 | Millennium Pharmaceuticals, Inc. | Heterocyclic compounds useful as RAF kinase inhibitors |
| KR20100045480A (ko) | 2007-08-10 | 2010-05-03 | 크리스탈지노믹스(주) | 피리딘 유도체 및 이들의 사용방법 |
| GB0716292D0 (en) | 2007-08-21 | 2007-09-26 | Biofocus Dpi Ltd | Imidazopyrazine compounds |
| WO2009085256A1 (en) * | 2007-12-27 | 2009-07-09 | Panacos Pharmaceuticals, Inc. | Anti-hiv compounds |
| CA2722923C (en) * | 2008-04-29 | 2016-08-02 | Boehringer Ingelheim International Gmbh | Indazole compounds as ccr1 receptor antagonists |
| CA2722811C (en) | 2008-05-06 | 2016-07-05 | Boehringer Ingelheim International Gmbh | Pyrazole compounds as ccr1 antagonists |
| NZ591115A (en) | 2008-09-26 | 2012-10-26 | Boehringer Ingelheim Int | Azaindazole compounds as ccr1 receptor antagonists |
| PH12012500775A1 (en) | 2009-10-21 | 2012-11-26 | Boehringer Ingelheim Int | Indazole and pyrazolopyridine compounds as ccr1 receptor antagonists |
| US8927550B2 (en) | 2009-10-27 | 2015-01-06 | Boehringer Ingelheim International Gmbh | Heterocyclic compounds as CCR1 receptor antagonists |
| WO2011071730A1 (en) * | 2009-12-08 | 2011-06-16 | Boehringer Ingelheim International Gmbh | Process for synthesis of intermediates useful for making substituted indazole and azaindazole compounds |
| US8871786B2 (en) | 2010-04-30 | 2014-10-28 | Boehringer Ingelheim International Gmbh | Azaindazole amide compounds as CCR1 receptor antagonists |
| WO2012087782A1 (en) | 2010-12-23 | 2012-06-28 | Boehringer Ingelheim International Gmbh | Pyrazolopiperidine compounds as ccr1 receptor antagonists |
-
2009
- 2009-09-22 NZ NZ591115A patent/NZ591115A/xx not_active IP Right Cessation
- 2009-09-22 MX MX2011002951A patent/MX2011002951A/es active IP Right Grant
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