JP2012503664A5 - - Google Patents
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- 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
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- carboxylic acid
- methylsulfanyl
- pyridine
- oxazol
- mmol
- Prior art date
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- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester 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
- 239000000203 mixture Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000002194 synthesizing Effects 0.000 description 5
- 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 4
- -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 na2so4 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
- 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
- 239000012267 brine Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N Phosphoryl chloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- 239000000463 material Substances 0.000 description 2
- PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K Ruthenium(III) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M Sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- AVFUHBJCUUTGCD-UHFFFAOYSA-M [Br-].[Mg+]C Chemical compound [Br-].[Mg+]C AVFUHBJCUUTGCD-UHFFFAOYSA-M 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 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
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical group [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
Description
例3:1−(4−フルオロフェニル)−1H−ピラゾロ[3,4−c]ピリジン−4−カルボン酸4−(4−メチル−ピペラジン−1−スルホニル)−ベンジルアミド(3)の合成
例9:酢酸2−{[5−({[1−(4−フルオロフェニル)−1H−ピラゾロ[3,4−c]ピリジン−4−カルボニル]−アミノ}−メチル)−ピリジン−2−スルホニル]−メチル−アミノ}−エチルエステル(9)の合成
例22:4−((S)−1−{[1−(4−フルオロフェニル)−1H−ピラゾロ[3,4−c]ピリジン−4−カルボニル]−アミノ}−エチル)−ピリジン−2−スルホン酸(22)の合成
[(S)−1−(2−メタンスルホニル−1−オキシ−ピリジン−4−イル)−プロピル]−カルバミン酸tert−ブチルエステル(1.7g、5.2mmol)のオキシ塩化リン(10mL)中の溶液を、還流で10分間加温した。次いで、混合物を複数回に分けて氷水(100mL)に添加し、30分間激しく撹拌した。次いで、溶液を飽和炭酸ナトリウムで塩基性とし、次いで酢酸エチル(4×30mL)で抽出した。合わせた有機層をブライン(2×50mL)で洗浄し、硫酸ナトリウム上で乾燥させ、真空下で濃縮すると、表題化合物が得られた。
例45:(S)−1−(2−メチルスルファニル−オキサゾール−5−イル)−プロピルアミン塩酸塩(45)の合成
例45:(S)−1−(2−メチルスルファニル−オキサゾール−5−イル)−プロピルアミン塩酸塩(45)の合成
2−クロロ−オキサゾール−5−カルボン酸エチルエステル(4g、22mmol)のDMF(75mL)中の溶液に、ナトリウムチオメトキシド(1.8g、25.7mmol)を添加した。混合物を50℃に加熱すると、黄色溶液が得られた。18時間後、混合物を飽和塩化アンモニウム水溶液(50mL)で希釈し、酢酸エチル(3×50mL)で抽出した。合わせた有機層をブライン(50mL)で洗浄し、硫酸ナトリウム上で乾燥させ、真空下で濃縮すると、2−エチルスルファニル−オキサゾール−5−カルボン酸エチルエステルが得られた。
2−エチルスルファニル−オキサゾール−5−カルボン酸エチルエステル(4.6g、24.57mmol)のエタノール(100mL)の溶液に、水酸化ナトリウムの2N水溶液(37mL、74mmol)を添加した。混合物を80℃で4時間加熱し、次いで真空下で濃縮してエタノールを除去した。次いで、残りの水溶液を1N HClで酸性化し、酢酸エチル(4×30mL)で抽出した。合わせた有機層をブライン(2×100mL)で洗浄し、硫酸ナトリウム上で乾燥させ、濃縮すると、2−メチルスルファニル−オキサゾール−5−カルボン酸が得られた。
例43に記載の方法と同じ方法を使用して、ワインレブアミドを介して2−メチルスルファニル−オキサゾール−5−カルボン酸を(S)−1−(2−メチルスルファニル−オキサゾール−5−イル)−プロピルアミン塩酸塩(45)に変換した。
2−エチルスルファニル−オキサゾール−5−カルボン酸エチルエステル(4.6g、24.57mmol)のエタノール(100mL)の溶液に、水酸化ナトリウムの2N水溶液(37mL、74mmol)を添加した。混合物を80℃で4時間加熱し、次いで真空下で濃縮してエタノールを除去した。次いで、残りの水溶液を1N HClで酸性化し、酢酸エチル(4×30mL)で抽出した。合わせた有機層をブライン(2×100mL)で洗浄し、硫酸ナトリウム上で乾燥させ、濃縮すると、2−メチルスルファニル−オキサゾール−5−カルボン酸が得られた。
例43に記載の方法と同じ方法を使用して、ワインレブアミドを介して2−メチルスルファニル−オキサゾール−5−カルボン酸を(S)−1−(2−メチルスルファニル−オキサゾール−5−イル)−プロピルアミン塩酸塩(45)に変換した。
メチルマグネシウムブロミドをエチルマグネシウムクロリドと置換した以外は、例43に記載の方法と同じ方法を使用して、ワインレブアミドを介して2−メチルスルファニル−オキサゾール−5−カルボン酸を(S)−1−(2−メチルスルファニル−オキサゾール−5−イル)−エチルアミン塩酸塩に変換した。
例43に記載の方法と同じ方法を使用して、ワインレブアミドを介して2−メチルスルファニル−オキサゾール−4−カルボン酸を(S)−1−(2−メチルスルファニル−オキサゾール−4−イル)−プロピルアミン塩酸塩に変換した。
例43に記載の方法と同じ方法を使用して、ワインレブアミドを介して2−メチルスルファニル−オキサゾール−4−カルボン酸を(S)−1−(2−メチルスルファニル−オキサゾール−4−イル)−プロピルアミン塩酸塩に変換した。
1−(4−フルオロフェニル)−1H−ピラゾロ[3,4−c]ピリジン−4−カルボン酸[(S)−1−(2−メチルスルファニル−オキサゾール−5−イル)−プロピル]−アミド(0.1g、0.2mmol)のアセトニトリル(25mL)および水(5mL)の混合物中の溶液に、過ヨウ素酸ナトリウム(0.155g、0.725mmol)、続いて三塩化ルテニウム(5mg、0.02mmol)を添加した。6時間後、混合物を濾過し、濾液を水(50mL)で希釈し、酢酸エチル(3×50mL)で抽出した。合わせた有機層を硫酸ナトリウム上で乾燥させ、濾過して濃縮した。粗材料を酢酸エチルに溶解し、シリカのパッドに通過させた。パッドからの材料を酢酸エチル−ヘキサンから結晶化させると、表題化合物が得られた。
例46に記載の方法と同じ方法を使用して、1−(4−フルオロフェニル)−1H−ピラゾロ[3,4−c]ピリジン−4−カルボン酸[(S)−1−(2−メチルスルファニル−オキサゾール−5−イル)−エチル]−アミドを、1−(4−フルオロフェニル)−1H−ピラゾロ[3,4−c]ピリジン−4−カルボン酸[(S)−1−(2−メタンスルホニル−オキサゾール−5−イル)−エチル]−アミドに変換した。
例46に記載の方法と同じ方法を使用して、1−(4−フルオロフェニル)−1H−ピラゾロ[3,4−c]ピリジン−4−カルボン酸[(S)−1−(2−メチルスルファニル−オキサゾール−5−イル)−エチル]−アミドを、1−(4−フルオロフェニル)−1H−ピラゾロ[3,4−c]ピリジン−4−カルボン酸[(S)−1−(2−メタンスルホニル−オキサゾール−5−イル)−エチル]−アミドに変換した。
例63:{2−(1−{[1−(4−フルオロフェニル)−1H−ピラゾロ[3,4−c]ピリジン−4−カルボニル]−アミノ}−プロピル)−5−メチル−オキサゾール−4−カルボニル]−アミノ}−酢酸メチルエステル(63)の合成
Claims (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 |
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JP2012503664A JP2012503664A (ja) | 2012-02-09 |
JP2012503664A5 true JP2012503664A5 (ja) | 2012-05-24 |
JP5507567B2 JP5507567B2 (ja) | 2014-05-28 |
Family
ID=41349302
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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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 (ja) |
EP (1) | EP2346868B1 (ja) |
JP (1) | JP5507567B2 (ja) |
KR (1) | KR20110060904A (ja) |
CN (1) | CN102227425A (ja) |
AP (1) | AP2739A (ja) |
AR (1) | AR073689A1 (ja) |
AU (1) | AU2009296839A1 (ja) |
BR (1) | BRPI0919844A2 (ja) |
CA (1) | CA2737472A1 (ja) |
CL (1) | CL2011000668A1 (ja) |
CO (1) | CO6351735A2 (ja) |
EA (1) | EA201100524A1 (ja) |
EC (1) | ECSP11010932A (ja) |
IL (1) | IL210857A0 (ja) |
MA (1) | MA32655B1 (ja) |
MX (1) | MX2011002951A (ja) |
NZ (1) | NZ591115A (ja) |
PE (1) | PE20110854A1 (ja) |
TW (1) | TW201018683A (ja) |
UA (1) | UA103634C2 (ja) |
UY (1) | UY32140A (ja) |
WO (1) | WO2010036632A1 (ja) |
ZA (1) | ZA201100625B (ja) |
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WO2009134666A1 (en) | 2008-04-29 | 2009-11-05 | Boehringer Ingelheim International Gmbh | Indazole compounds as ccr1 receptor antagonists |
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AU2009296839A1 (en) | 2008-09-26 | 2010-04-01 | Boehringer Ingelheim International Gmbh | Azaindazole compounds as CCR1 receptor antagonists |
CA2754605C (en) * | 2009-03-19 | 2018-04-17 | Medical Research Council Technology | Pyrazolopyridine compounds and their use as lrrk2 inhibitors |
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EP2493875B1 (en) | 2009-10-27 | 2014-08-06 | Boehringer Ingelheim International GmbH | Heterocyclic compounds as ccr1 receptor antagonists |
CN102596908A (zh) | 2009-12-08 | 2012-07-18 | 贝林格尔.英格海姆国际有限公司 | 用于制备取代的吲唑和氮杂吲唑化合物的中间体的合成方法 |
EP2563787B1 (en) | 2010-04-30 | 2014-11-26 | 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 |
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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 |
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