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 |
|---|---|---|---|---|
| JP5216912B2 (ja) | 2008-04-29 | 2013-06-19 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｃｒ１受容体拮抗薬としてのインダゾール化合物 |
| JP5411927B2 (ja) * | 2008-05-06 | 2014-02-12 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｃｒ１アンタゴニストとしてのピラゾール化合物 |
| PE20110854A1 (es) | 2008-09-26 | 2011-12-23 | Boehringer Ingelheim Int | DERIVADOS DE 1-FENIL-1H-PIRAZOLO[3,4-c]PIRIDINA-4-CARBONILAMINA COMO ANTAGONISTAS DE LOS RECEPTORES CCR1 |
| EP2408772B1 (en) * | 2009-03-19 | 2015-07-01 | Medical Research Council Technology | Compounds |
| AP2012006204A0 (en) | 2009-10-21 | 2012-04-30 | Boehringer Ingelheim Int | Indazole and pyrazolopyridine compounds as CCR1 receptor antagonists. |
| JP5542214B2 (ja) * | 2009-10-27 | 2014-07-09 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｃｒ１受容体アンタゴニストとしての複素環化合物 |
| IN2012DN05081A (enExample) * | 2009-12-08 | 2015-10-09 | Boehringer Ingelheim Int | |
| 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 |
| AR082885A1 (es) | 2010-09-03 | 2013-01-16 | Genentech Inc | Compuestos y composiciones para la inhibicion de nampt |
| US8546442B2 (en) | 2010-12-23 | 2013-10-01 | Boehringer Ingelheim International Gmbh | Pyrazolopiperidine compounds as CCR1 receptor antagonists |
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| WO2017068089A2 (en) | 2015-10-23 | 2017-04-27 | Vifor (International) Ag | Novel ferroportin inhibitors |
| WO2017081310A1 (en) | 2015-11-13 | 2017-05-18 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
| EP3373733A1 (en) | 2015-11-13 | 2018-09-19 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
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| 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 |
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| JP5411927B2 (ja) | 2008-05-06 | 2014-02-12 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｃｒ１アンタゴニストとしてのピラゾール化合物 |
| PE20110854A1 (es) | 2008-09-26 | 2011-12-23 | Boehringer Ingelheim Int | DERIVADOS DE 1-FENIL-1H-PIRAZOLO[3,4-c]PIRIDINA-4-CARBONILAMINA COMO ANTAGONISTAS DE LOS RECEPTORES CCR1 |
| AP2012006204A0 (en) | 2009-10-21 | 2012-04-30 | Boehringer Ingelheim Int | Indazole and pyrazolopyridine compounds as CCR1 receptor antagonists. |
| JP5542214B2 (ja) | 2009-10-27 | 2014-07-09 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｃｒ１受容体アンタゴニストとしての複素環化合物 |
| IN2012DN05081A (enExample) | 2009-12-08 | 2015-10-09 | Boehringer Ingelheim Int | |
| US8871786B2 (en) | 2010-04-30 | 2014-10-28 | Boehringer Ingelheim International Gmbh | Azaindazole amide compounds as CCR1 receptor antagonists |
| US8546442B2 (en) | 2010-12-23 | 2013-10-01 | Boehringer Ingelheim International Gmbh | Pyrazolopiperidine compounds as CCR1 receptor antagonists |
-
2009
- 2009-09-22 PE PE2011000789A patent/PE20110854A1/es not_active Application Discontinuation
- 2009-09-22 EA EA201100524A patent/EA201100524A1/ru unknown
- 2009-09-22 CN CN2009801472064A patent/CN102227425A/zh active Pending
- 2009-09-22 UA UAA201105061A patent/UA103634C2/ru unknown
- 2009-09-22 MX MX2011002951A patent/MX2011002951A/es active IP Right Grant
- 2009-09-22 WO PCT/US2009/057778 patent/WO2010036632A1/en not_active Ceased
- 2009-09-22 AP AP2011005685A patent/AP2739A/xx active
- 2009-09-22 KR KR1020117006720A patent/KR20110060904A/ko not_active Withdrawn
- 2009-09-22 JP JP2011529154A patent/JP5507567B2/ja active Active
- 2009-09-22 EP EP09792818.8A patent/EP2346868B1/en active Active
- 2009-09-22 CA CA2737472A patent/CA2737472A1/en not_active Abandoned
- 2009-09-22 AU AU2009296839A patent/AU2009296839A1/en not_active Abandoned
- 2009-09-22 BR BRPI0919844A patent/BRPI0919844A2/pt not_active IP Right Cessation
- 2009-09-22 US US12/564,129 patent/US7879873B2/en active Active
- 2009-09-22 NZ NZ591115A patent/NZ591115A/xx not_active IP Right Cessation
- 2009-09-24 UY UY0001032140A patent/UY32140A/es not_active Application Discontinuation
- 2009-09-25 TW TW098132530A patent/TW201018683A/zh unknown
- 2009-09-25 AR ARP090103709A patent/AR073689A1/es unknown
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2010
- 2010-12-16 US US12/969,753 patent/US8063065B2/en active Active
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2011
- 2011-01-25 IL IL210857A patent/IL210857A0/en unknown
- 2011-01-25 ZA ZA2011/00625A patent/ZA201100625B/en unknown
- 2011-03-17 CO CO11033549A patent/CO6351735A2/es active IP Right Grant
- 2011-03-24 MA MA33724A patent/MA32655B1/fr unknown
- 2011-03-25 CL CL2011000668A patent/CL2011000668A1/es unknown
- 2011-03-29 EC EC2011010932A patent/ECSP11010932A/es unknown
- 2011-10-14 US US13/273,509 patent/US8163918B2/en active Active
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2012
- 2012-02-08 US US13/368,397 patent/US8338610B2/en active Active
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