WO2005009986A1 - Preparation en pot unique de s-(guanidino-4-yl-methyl)-isothiouree dichlorhydrate - Google Patents

Preparation en pot unique de s-(guanidino-4-yl-methyl)-isothiouree dichlorhydrate Download PDF

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Publication number
WO2005009986A1
WO2005009986A1 PCT/IN2003/000252 IN0300252W WO2005009986A1 WO 2005009986 A1 WO2005009986 A1 WO 2005009986A1 IN 0300252 W IN0300252 W IN 0300252W WO 2005009986 A1 WO2005009986 A1 WO 2005009986A1
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WO
WIPO (PCT)
Prior art keywords
formula
reaction
guanidino
methyl
thiourea
Prior art date
Application number
PCT/IN2003/000252
Other languages
English (en)
Inventor
Veera Venkata Satyanarayana Murthy Talluri
Ramesh Babu Potluri
Subramanian Hariharakrishnan Venkata
Koteswara Rao Moparthi
Original Assignee
Talluri Veera Venkata Satyanar
Ramesh Babu Potluri
Venkata Subramanian Hariharakr
Koteswara Rao Moparthi
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 Talluri Veera Venkata Satyanar, Ramesh Babu Potluri, Venkata Subramanian Hariharakr, Koteswara Rao Moparthi filed Critical Talluri Veera Venkata Satyanar
Priority to AU2003259546A priority Critical patent/AU2003259546A1/en
Priority to PCT/IN2003/000252 priority patent/WO2005009986A1/fr
Publication of WO2005009986A1 publication Critical patent/WO2005009986A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/36—Nitrogen atoms

Definitions

  • the present invention relates to a novel one-pot preparation of S-(Guanidino-4-yl- methyl)-isothiourea dihydrochloride.
  • Famotidine is one of the important compounds for the inhibition of gastric and intestinal ulceration.
  • EP 0128736 describes the preparation of Famotidine via thiazoline derivatives of formula V
  • the compound of formula V is converted into compound of formula IV, which is a crucial intermediate for the preparation of Famotidine.
  • Japan Patent application No 53147069 describes the synthesis of famotidine through the intermediate, 2-guanidino-4-chloromethyl thiazole, which is a difficult compound to handle due to its irritable odor. It also causes dermititis.
  • the invention relates to a new process for one pot preparation of S-(Guanidino-4-yl methyl)-isothiourea dihydrochloride of formula IV,
  • the intermediate of formula III was isolated and then converted into the compound of formula IV.
  • the yield for the intermediate of formula III was about 90-93%.
  • the conversion of the intermediate of formula III to intermediate of formula IV was tried in different alkanols viz., methanol, ethanol, n- proponal, isoproponal etc. It was most preferable to use isoproponal, since this solvent gave the best results.
  • the compound of formula IV was isolated in about 83% yield.
  • ethanoic acid concentration in the range of 15-20%.
  • a temperature range of 30-50°C was preferred for the reaction.
  • a temperature range of 35° - 45° C was more preferred.
  • the overall yield of the compound IV was around 92-93%.
  • reaction mass After charging thiourea, the reaction mass was heated to reflux temperature and maintained for 4-5hours. Then the reaction mass was cooled to 10° C and the precipitated product was centrifuged. The cake was washed with isopropyl alcohol (2 x 90lts). The product was dried at 75° - 80° C to yield 330 kg of the dihydrochloride with melting point of 205-210°C

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

La présente invention se rapporte à une nouvelle préparation en pot unique de N-[[4-(amino imino-éthyl)thio]méthyl]-2-thiozolyl]-guanidine dichlorhydrate représentée par la formule (IV), que l'on obtient en faisant réagir de la 1,3-idiochloro-acétone représentée par la formule (I) avec de la guanidinothiourée représentée par la formule (II), et en faisant réagir le composé formé in situ (représenté par la formule III) avec de la thiourée.
PCT/IN2003/000252 2003-07-28 2003-07-28 Preparation en pot unique de s-(guanidino-4-yl-methyl)-isothiouree dichlorhydrate WO2005009986A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2003259546A AU2003259546A1 (en) 2003-07-28 2003-07-28 One-pot preparation of s-(guanidino-4-yl-methyl)-isothiourea dihydrochoride
PCT/IN2003/000252 WO2005009986A1 (fr) 2003-07-28 2003-07-28 Preparation en pot unique de s-(guanidino-4-yl-methyl)-isothiouree dichlorhydrate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IN2003/000252 WO2005009986A1 (fr) 2003-07-28 2003-07-28 Preparation en pot unique de s-(guanidino-4-yl-methyl)-isothiouree dichlorhydrate

Publications (1)

Publication Number Publication Date
WO2005009986A1 true WO2005009986A1 (fr) 2005-02-03

Family

ID=34090465

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2003/000252 WO2005009986A1 (fr) 2003-07-28 2003-07-28 Preparation en pot unique de s-(guanidino-4-yl-methyl)-isothiouree dichlorhydrate

Country Status (2)

Country Link
AU (1) AU2003259546A1 (fr)
WO (1) WO2005009986A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009058997A2 (fr) * 2007-11-01 2009-05-07 Biocept Inc. Isolement non invasif d'acide nucléique fœtal
WO2015002150A1 (fr) 2013-07-03 2015-01-08 株式会社新日本科学 Nouveau composé, agent de détection du transporteur de cations organiques 3 et inhibiteur de l'activité du transporteur de cations organiques 3

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0128736A1 (fr) * 1983-06-07 1984-12-19 Yamanouchi Pharmaceutical Co., Ltd. Composés 2-guanidinothiazolines, leur préparation et leur utilisation comme intermédiaires

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0128736A1 (fr) * 1983-06-07 1984-12-19 Yamanouchi Pharmaceutical Co., Ltd. Composés 2-guanidinothiazolines, leur préparation et leur utilisation comme intermédiaires

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009058997A2 (fr) * 2007-11-01 2009-05-07 Biocept Inc. Isolement non invasif d'acide nucléique fœtal
WO2009058997A3 (fr) * 2007-11-01 2009-07-09 Biocept Inc Isolement non invasif d'acide nucléique fœtal
WO2015002150A1 (fr) 2013-07-03 2015-01-08 株式会社新日本科学 Nouveau composé, agent de détection du transporteur de cations organiques 3 et inhibiteur de l'activité du transporteur de cations organiques 3

Also Published As

Publication number Publication date
AU2003259546A1 (en) 2005-02-14

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