JPWO2014017516A1 - 4−[5−(ピリジン−4−イル)−1h−1,2,4−トリアゾール−3−イル]ピリジン−2−カルボニトリルの製造方法および中間体 - Google Patents
4−[5−(ピリジン−4−イル)−1h−1,2,4−トリアゾール−3−イル]ピリジン−2−カルボニトリルの製造方法および中間体 Download PDFInfo
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- JPWO2014017516A1 JPWO2014017516A1 JP2014526957A JP2014526957A JPWO2014017516A1 JP WO2014017516 A1 JPWO2014017516 A1 JP WO2014017516A1 JP 2014526957 A JP2014526957 A JP 2014526957A JP 2014526957 A JP2014526957 A JP 2014526957A JP WO2014017516 A1 JPWO2014017516 A1 JP WO2014017516A1
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- UBVZQGOVTLIHLH-UHFFFAOYSA-N N#Cc1cc(-c2n[nH]c(-c3ccncc3)n2)ccn1 Chemical compound N#Cc1cc(-c2n[nH]c(-c3ccncc3)n2)ccn1 UBVZQGOVTLIHLH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/86—Hydrazides; Thio or imino analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Abstract
Description
[1]下記式(4)
[2]下記式(2)
[3]下記式(2)
[4]下記式(4)
第一工程は、4−シアノピリジン−N−オキシド(2)と、イソニコチン酸ヒドラジドとを、アルカリ金属アルコキシドの存在下に反応させて化合物(3)を得る工程である。
用いられるアルカリ金属アルコキシドとしては、アルカリ金属C1−C6アルコキシドが好ましく、具体例としてナトリウムメチラート、ナトリウムエチラート等が挙げられる。この反応は、溶媒中で行うのが好ましく、溶媒としては、メタノール、エタノール等のアルコール系溶媒が好ましい。
第二工程は、化合物(3)をシアノ化剤によりシアノ化して化合物(4)を得る工程である。
第三工程は、化合物(4)を酸触媒下、閉環反応することにより化合物(1)を得る工程である。
1H−NMR:プロトン核磁気共鳴スペクトル、DMSO−d6:重水素ジメチルスルホキシド、Hz:ヘルツ、J:カップリング定数、s:シングレット、dd:ダブルダブレット、d:ダブレット、br:ブロード。尚、NMRは270MHz核磁気共鳴スペクトルを示し、内部標準物質としてTMS(テトラメチルシラン)を用いた。MSは質量分析を示し、イオン化法がESI(エレクトロスプレーイオン化法)である測定機器を用いた。
4−シアノピリジン−N−オキシド(2)5.00gをメタノール40mLに懸濁し、ナトリウムメチラート22.4mgを加え、窒素雰囲気下40℃で2時間攪拌した。同温にてイソニコチン酸ヒドラジド5.71gを加え40℃で4時間攪拌した。反応液を室温まで冷却した後、析出した結晶をろ取し、メタノール15mLで洗浄後、80℃で15時間乾燥し、N”−(4−ピリジンカルボニル)−4−ピリジンヒドラジドイミド−1−オキシド(3)9.60gを得た。
1H−NMR(DMSO−d6)δ(ppm):6.98(br,2H),7.81(d,2H,J=5.77Hz),7.85(d,2H,J=7.09Hz),8.29(d,2H,J=7.09Hz),8.73(d,2H,J=5.77Hz),10.37(br,1H)
MS m/z:256[M−H]-
N”−(4−ピリジンカルボニル)−4−ピリジンヒドラジドイミド−1−オキシド(3)10.0gをN,N−ジメチルホルムアミド48mLに懸濁し、窒素雰囲気下、40℃でジメチルカルバモイルクロリド9.20gを加え1時間撹拌した。同温にてシアン化ナトリウム2.48gを加え、さらに1時間撹拌した。反応液を5℃以下まで冷却した後、5%炭酸水素ナトリウム水溶液100mL、水100mLを順次滴下した。析出した結晶をろ取し、水100mLで洗浄した後、80℃で15時間減圧乾燥し、4−ピリジンカルボン酸N’−(2−シアノピリジン−4−カルボンイミドイル)ヒドラジド(4)9.28gを得た。
1H−NMR(DMSO−d6)δ(ppm):7.15(br,2H),7.82(d,2H,J=5.61Hz),8.14(d,1H,J=5.11Hz),8.37(s,1H),8.75(d,2H,J=5.61Hz),8.86(d,1H,J=5.11Hz),10.47(br,1H)
MS m/z:265[M−H]-
4−ピリジンカルボン酸N’−(2−シアノピリジン−4−カルボンイミドイル)ヒドラジド(4)9.25gに水82mL、2−ブタノール8.2mL、リン酸4.00gを加え、80℃で8時間撹拌した。反応液を室温まで冷却し、析出した結晶をろ取した後、水:2−ブタノール=10:1の混合溶液92.5mLで洗浄した。得られた結晶を80℃で13時間減圧乾燥し、4−[5−(ピリジン−4−イル)−1H−1,2,4−トリアゾール−3−イル]ピリジン−2−カルボニトリル(1)7.89gを得た。
1H−NMR(DMSO−d6)δ(ppm):8.02(dd,2H,J=4.59,1.62Hz),8.32(dd,1H,J=5.13,1.62Hz),8.55(dd,1H,J=1.62,1.08Hz),8.80(dd,2H,J=4.59,1.62Hz),8.93(dd,1H,5.13,1.08Hz)
MS m/z:247[M−H]-
Claims (4)
Priority Applications (1)
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JP2014526957A JP5827407B2 (ja) | 2012-07-25 | 2013-07-24 | 4−[5−(ピリジン−4−イル)−1h−1,2,4−トリアゾール−3−イル]ピリジン−2−カルボニトリルの製造方法および中間体 |
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JP2012177538 | 2012-07-25 | ||
JP2012177538 | 2012-07-25 | ||
JP2014526957A JP5827407B2 (ja) | 2012-07-25 | 2013-07-24 | 4−[5−(ピリジン−4−イル)−1h−1,2,4−トリアゾール−3−イル]ピリジン−2−カルボニトリルの製造方法および中間体 |
PCT/JP2013/070005 WO2014017516A1 (ja) | 2012-07-25 | 2013-07-24 | 4-[5-(ピリジン-4-イル)-1h-1,2,4-トリアゾール-3-イル]ピリジン-2-カルボニトリルの製造方法および中間体 |
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JP5827407B2 JP5827407B2 (ja) | 2015-12-02 |
JPWO2014017516A1 true JPWO2014017516A1 (ja) | 2016-07-11 |
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US (1) | US9428488B2 (ja) |
EP (1) | EP2878595A4 (ja) |
JP (1) | JP5827407B2 (ja) |
KR (1) | KR101719891B1 (ja) |
CN (1) | CN104411686B (ja) |
AU (1) | AU2013293974B2 (ja) |
BR (1) | BR112014032229B1 (ja) |
CA (1) | CA2876268C (ja) |
HK (1) | HK1204788A1 (ja) |
IL (1) | IL236081A (ja) |
IN (1) | IN2014DN10530A (ja) |
MX (1) | MX362102B (ja) |
MY (1) | MY185203A (ja) |
NZ (1) | NZ702797A (ja) |
PH (1) | PH12015500160B1 (ja) |
RU (1) | RU2644766C2 (ja) |
TW (1) | TWI580675B (ja) |
WO (1) | WO2014017516A1 (ja) |
ZA (1) | ZA201500462B (ja) |
Families Citing this family (9)
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CN105367490B (zh) * | 2014-08-18 | 2019-01-04 | 上海医药工业研究院 | 合成托吡司他的新中间体及其制备方法 |
JP6811717B2 (ja) | 2015-02-25 | 2021-01-13 | ファーマシェン エス.エー. | トピロキソスタット及びその中間体の調製のための方法 |
CN105693699B (zh) * | 2015-03-30 | 2019-06-18 | 苏州晶云药物科技股份有限公司 | 托吡司他的晶型及其制备方法 |
CN104758263B (zh) * | 2015-04-22 | 2017-08-22 | 青岛正大海尔制药有限公司 | 一种托匹司他片及其制备方法 |
CN105294656A (zh) * | 2015-10-10 | 2016-02-03 | 大道隆达(北京)医药科技发展有限公司 | 一种托匹司他的制备工艺和方法 |
CN106008465A (zh) * | 2016-03-16 | 2016-10-12 | 江苏悦兴药业有限公司 | 一种托匹司他杂质的合成方法 |
CN108101840A (zh) * | 2018-01-26 | 2018-06-01 | 南京华威医药科技集团有限公司 | 托吡司他及其中间体制备方法 |
CN113666909A (zh) * | 2020-05-14 | 2021-11-19 | 鲁南制药集团股份有限公司 | 一种托匹司他的制备方法 |
CN115093399A (zh) * | 2022-07-29 | 2022-09-23 | 武汉工程大学 | 一种抗痛风药物托匹司他的制备方法 |
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---|---|---|---|---|
US3947577A (en) * | 1973-05-21 | 1976-03-30 | Merck & Co., Inc. | Anti-hyperuricemia composition |
US4097599A (en) * | 1973-11-13 | 1978-06-27 | Commonwealth Scientific And Industrial Research Organization | Triazoles |
AR241530A1 (es) | 1984-12-21 | 1992-08-31 | Ciba Geigy A G Cesionaria De F | 1,2,4-triazoles, composicion para el control de pestes y procedimiento para la preparacion de 1,2,4-triazoles. |
ZA859576B (en) * | 1984-12-21 | 1986-08-27 | Hoffmann La Roche | Heterocyclic compounds |
JP3217846B2 (ja) * | 1992-03-04 | 2001-10-15 | クミアイ化学工業株式会社 | トリアゾール誘導体及び殺虫剤 |
PT1123287E (pt) * | 1998-10-23 | 2003-12-31 | Dow Agrosciences Llc | 1-(piridil substituido)-1,2,4-triazoles insecticidas |
JP2003064410A (ja) | 2001-08-22 | 2003-03-05 | Nippon Steel Corp | 転炉吹錬方法および上吹きランス |
US7074816B2 (en) | 2002-01-28 | 2006-07-11 | Fuji Yakuhin Co., Ltd. | 1 2 4-triazole compound |
JP2005009991A (ja) | 2003-06-18 | 2005-01-13 | Alpine Electronics Inc | 車載用ナビゲーション装置及び車載用ナビゲーション装置の表示方法 |
CN1826335A (zh) * | 2003-07-24 | 2006-08-30 | 株式会社富士药品 | 1,2,4-三唑化合物的制造方法以及其中间体 |
JP2005041802A (ja) | 2003-07-25 | 2005-02-17 | Fujiyakuhin Co Ltd | 1,2,4−トリアゾール化合物の製造方法 |
US20060189811A1 (en) | 2004-07-23 | 2006-08-24 | Fujiyakuhin Co., Ltd. | Process for producing 1,2,4-triazole compound and intermediate therefor |
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US20150166510A1 (en) | 2015-06-18 |
HK1204788A1 (en) | 2015-12-04 |
CN104411686B (zh) | 2016-08-31 |
KR20150035586A (ko) | 2015-04-06 |
AU2013293974B2 (en) | 2017-06-01 |
MX2015001114A (es) | 2015-04-08 |
IL236081A0 (en) | 2015-02-01 |
EP2878595A4 (en) | 2015-12-09 |
CA2876268A1 (en) | 2014-01-30 |
WO2014017516A1 (ja) | 2014-01-30 |
PH12015500160A1 (en) | 2015-03-16 |
MX362102B (es) | 2019-01-04 |
EP2878595A1 (en) | 2015-06-03 |
IL236081A (en) | 2017-11-30 |
RU2015106138A (ru) | 2016-09-10 |
KR101719891B1 (ko) | 2017-03-24 |
NZ702797A (en) | 2017-03-31 |
ZA201500462B (en) | 2016-10-26 |
RU2644766C2 (ru) | 2018-02-14 |
US9428488B2 (en) | 2016-08-30 |
PH12015500160B1 (en) | 2015-03-16 |
IN2014DN10530A (ja) | 2015-08-21 |
AU2013293974A1 (en) | 2015-01-22 |
BR112014032229A2 (pt) | 2017-06-27 |
TWI580675B (zh) | 2017-05-01 |
TW201408642A (zh) | 2014-03-01 |
BR112014032229B1 (pt) | 2021-02-09 |
JP5827407B2 (ja) | 2015-12-02 |
CA2876268C (en) | 2016-12-20 |
CN104411686A (zh) | 2015-03-11 |
MY185203A (en) | 2021-04-30 |
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