EP4698521A1 - Procédé de préparation de 4-hydroxy-4,5-dihydrothiazole-2-carbonitrile et de ses dérivés - Google Patents

Procédé de préparation de 4-hydroxy-4,5-dihydrothiazole-2-carbonitrile et de ses dérivés

Info

Publication number
EP4698521A1
EP4698521A1 EP24719164.6A EP24719164A EP4698521A1 EP 4698521 A1 EP4698521 A1 EP 4698521A1 EP 24719164 A EP24719164 A EP 24719164A EP 4698521 A1 EP4698521 A1 EP 4698521A1
Authority
EP
European Patent Office
Prior art keywords
formula
carbonitrile
dihydrothiazole
hydroxy
alkyl
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
Application number
EP24719164.6A
Other languages
German (de)
English (en)
Inventor
Stefan Hildbrand
Christian Oliver KAPPE
Michael PRIESCHL
Kurt Andreas PUENTENER
Jason Douglas WILLIAMS
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of EP4698521A1 publication Critical patent/EP4698521A1/fr
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D277/14—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne un nouveau procédé de préparation de 4-hydroxy-4,5-dihydrothiazole-2-carbonitrile de formule (I), (I). Le 4-hydroxy-4,5-dihydrothiazole-2-carbonitrile est un intermédiaire polyvalent qui peut être utilisé pour préparer des composés précurseurs polyvalents de composés pharmaceutiquement actifs, tels que des médicaments et d'autres composés chimiques utilisés en médecine. L'invention concerne en outre la transformation du 4-hydroxy-4,5-dihydrothiazole-2-carbonitrile de formule I en thiazole-2-carbonitrile de formule (III), (III), le thiazole-2-carboximidamide de formule (V), ou un sel de celui-ci, la formule (V), (V) et les dérivés de 4-hydroxy-4,5-dihydrothiazole-2-carbonitrile de formule (IV), (IV), -26- où R1 est un alkyle en C1-6 ou phényle et le cycle phényle étant éventuellement substitué par, halogène, alkyle en C1-6 ou alcoxy en C1-6.
EP24719164.6A 2023-04-17 2024-04-15 Procédé de préparation de 4-hydroxy-4,5-dihydrothiazole-2-carbonitrile et de ses dérivés Pending EP4698521A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP23168155 2023-04-17
PCT/EP2024/060118 WO2024218026A1 (fr) 2023-04-17 2024-04-15 Procédé de préparation de 4-hydroxy-4,5-dihydrothiazole-2-carbonitrile et de ses dérivés

Publications (1)

Publication Number Publication Date
EP4698521A1 true EP4698521A1 (fr) 2026-02-25

Family

ID=86051965

Family Applications (1)

Application Number Title Priority Date Filing Date
EP24719164.6A Pending EP4698521A1 (fr) 2023-04-17 2024-04-15 Procédé de préparation de 4-hydroxy-4,5-dihydrothiazole-2-carbonitrile et de ses dérivés

Country Status (4)

Country Link
EP (1) EP4698521A1 (fr)
CN (1) CN120858090A (fr)
TW (1) TW202506652A (fr)
WO (1) WO2024218026A1 (fr)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7262316B2 (en) * 2002-10-21 2007-08-28 Ihara Chemical Industry Co., Ltd. Process for producing aromatic nitrile compound
EP2771338A2 (fr) * 2011-10-25 2014-09-03 Université de Droit et de la Santé de Lille 2 Derives de 1,2,4-oxadiazoles comme inhibiteurs d'ethr pour l'utilisation dans le traitement de la tuberculose
JP6306750B2 (ja) 2014-03-07 2018-04-04 エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ Ｂ型肝炎ウイルス感染症の治療および予防のための新規な６−縮合ヘテロアリールジヒドロピリミジン

Also Published As

Publication number Publication date
WO2024218026A1 (fr) 2024-10-24
CN120858090A (zh) 2025-10-28
TW202506652A (zh) 2025-02-16

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