FR2322860A1 - Dimethylbiguanide hydrochloride prepn. - by reaction of hydrogen chloride gas with a conc. soln. of dimethylamine and dicyandiamide in xylene - Google Patents

Dimethylbiguanide hydrochloride prepn. - by reaction of hydrogen chloride gas with a conc. soln. of dimethylamine and dicyandiamide in xylene

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Publication number
FR2322860A1
FR2322860A1 FR7527350A FR7527350A FR2322860A1 FR 2322860 A1 FR2322860 A1 FR 2322860A1 FR 7527350 A FR7527350 A FR 7527350A FR 7527350 A FR7527350 A FR 7527350A FR 2322860 A1 FR2322860 A1 FR 2322860A1
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FR
France
Prior art keywords
reaction
dicyandiamide
dimethylamine
xylene
conc
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
Application number
FR7527350A
Other languages
French (fr)
Other versions
FR2322860B1 (en
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.)
Aron Sarl
Original Assignee
Aron Sarl
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 Aron Sarl filed Critical Aron Sarl
Priority to FR7527350A priority Critical patent/FR2322860A1/en
Publication of FR2322860A1 publication Critical patent/FR2322860A1/en
Application granted granted Critical
Publication of FR2322860B1 publication Critical patent/FR2322860B1/fr
Granted legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
    • C07C279/24—Y being a hetero atom
    • C07C279/26—X and Y being nitrogen atoms, i.e. biguanides

Landscapes

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

Abstract

Dimethylbiguanide hydrochloride is prepd. by adding progressively initially at room temp., hydrogen chloride gas to a conc. solution of equimolar proportions of dimethylamine and dicyandiamide in an organic solvent, esp. xylene. The reaction is more readily controlled and yields are less likely to be reduced by degradation than in processes in which dimthylamine hydrochloride reacts with dicyandiamine with the application of external heat to initiate the reaction. The prod. is an oral hypoglycaemic agent. Typically, a 96% yield of hydrochloride is obtd. by reaction of HCl gas (365 kg.) with a solution of dimethylamine (450 kg.) and dicyandiamide (840 kg.) in xylene ( 1000 litres).
FR7527350A 1975-09-05 1975-09-05 Dimethylbiguanide hydrochloride prepn. - by reaction of hydrogen chloride gas with a conc. soln. of dimethylamine and dicyandiamide in xylene Granted FR2322860A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7527350A FR2322860A1 (en) 1975-09-05 1975-09-05 Dimethylbiguanide hydrochloride prepn. - by reaction of hydrogen chloride gas with a conc. soln. of dimethylamine and dicyandiamide in xylene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7527350A FR2322860A1 (en) 1975-09-05 1975-09-05 Dimethylbiguanide hydrochloride prepn. - by reaction of hydrogen chloride gas with a conc. soln. of dimethylamine and dicyandiamide in xylene

Publications (2)

Publication Number Publication Date
FR2322860A1 true FR2322860A1 (en) 1977-04-01
FR2322860B1 FR2322860B1 (en) 1979-04-27

Family

ID=9159684

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7527350A Granted FR2322860A1 (en) 1975-09-05 1975-09-05 Dimethylbiguanide hydrochloride prepn. - by reaction of hydrogen chloride gas with a conc. soln. of dimethylamine and dicyandiamide in xylene

Country Status (1)

Country Link
FR (1) FR2322860A1 (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010146604A3 (en) * 2009-06-18 2011-02-10 Exemed Pharmaceuticals Processes for preparing metformin hydrochloride
WO2011147528A1 (en) 2010-05-26 2011-12-01 Merck Patent Gmbh Biguanide compounds and its use for treating cancer
CN102516130A (en) * 2011-11-26 2012-06-27 赤峰万泽制药有限责任公司 Preparation method of metformin hydrochloride
WO2013002880A1 (en) 2011-06-29 2013-01-03 The General Hospital Corporation Compositions and methods for enhancing bioenergetic status in female germ cells
WO2013159190A1 (en) 2012-04-25 2013-10-31 Inovobiologic, Inc. Dietary fiber compositions for the treatment of metabolic disease
WO2016059507A1 (en) 2014-10-13 2016-04-21 Kamavarapu Sarath Kumar Improved process for the preparation of high pure metformine
WO2019154769A1 (en) 2018-02-07 2019-08-15 Merck Patent Gmbh Process for the preparation of metformin
CN112717866A (en) * 2020-12-10 2021-04-30 安徽广信农化股份有限公司 Synthesis process of dimethylamine hydrochloride
WO2021160608A1 (en) 2020-02-13 2021-08-19 Zakłady Farmaceutyczne POLPHARMA S.A. Pharmaceutical composition comprising linagliptin and metformin
CN115108945A (en) * 2022-07-14 2022-09-27 山东省分析测试中心 Preparation method of metformin hydrochloride crystal and monodisperse rod-like crystal with uniform particle size obtained by adopting preparation method

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5898619B2 (en) 2010-08-06 2016-04-06 大日本住友製薬株式会社 Water-soluble drug release controlled formulation
CN113248409B (en) * 2021-05-21 2023-01-03 海南海力制药有限公司 Synthetic method and application of metformin hydrochloride

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR926379A (en) * 1944-11-03 1947-09-30 Ici Ltd Manufacture of biguanyl compounds
CH266889A (en) * 1945-09-11 1950-02-28 American Cyanamid Co A process for preparing 1-isopropyl-5-p-chlorophenyl-biguanidine hydrochloride.

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR926379A (en) * 1944-11-03 1947-09-30 Ici Ltd Manufacture of biguanyl compounds
CH266889A (en) * 1945-09-11 1950-02-28 American Cyanamid Co A process for preparing 1-isopropyl-5-p-chlorophenyl-biguanidine hydrochloride.

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010146604A3 (en) * 2009-06-18 2011-02-10 Exemed Pharmaceuticals Processes for preparing metformin hydrochloride
WO2011147528A1 (en) 2010-05-26 2011-12-01 Merck Patent Gmbh Biguanide compounds and its use for treating cancer
WO2013002880A1 (en) 2011-06-29 2013-01-03 The General Hospital Corporation Compositions and methods for enhancing bioenergetic status in female germ cells
CN102516130A (en) * 2011-11-26 2012-06-27 赤峰万泽制药有限责任公司 Preparation method of metformin hydrochloride
WO2013159190A1 (en) 2012-04-25 2013-10-31 Inovobiologic, Inc. Dietary fiber compositions for the treatment of metabolic disease
WO2016059507A1 (en) 2014-10-13 2016-04-21 Kamavarapu Sarath Kumar Improved process for the preparation of high pure metformine
WO2019154769A1 (en) 2018-02-07 2019-08-15 Merck Patent Gmbh Process for the preparation of metformin
WO2021160608A1 (en) 2020-02-13 2021-08-19 Zakłady Farmaceutyczne POLPHARMA S.A. Pharmaceutical composition comprising linagliptin and metformin
CN112717866A (en) * 2020-12-10 2021-04-30 安徽广信农化股份有限公司 Synthesis process of dimethylamine hydrochloride
CN115108945A (en) * 2022-07-14 2022-09-27 山东省分析测试中心 Preparation method of metformin hydrochloride crystal and monodisperse rod-like crystal with uniform particle size obtained by adopting preparation method
CN115108945B (en) * 2022-07-14 2024-05-17 山东省分析测试中心 Preparation method of metformin hydrochloride crystal and monodisperse rod-shaped crystal with uniform granularity obtained by adopting method

Also Published As

Publication number Publication date
FR2322860B1 (en) 1979-04-27

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