WO2003055857A8 - A process for synthesis of heterocyclic aminoalkyl benzamides - Google Patents

A process for synthesis of heterocyclic aminoalkyl benzamides

Info

Publication number
WO2003055857A8
WO2003055857A8 PCT/YU2002/000029 YU0200029W WO03055857A8 WO 2003055857 A8 WO2003055857 A8 WO 2003055857A8 YU 0200029 W YU0200029 W YU 0200029W WO 03055857 A8 WO03055857 A8 WO 03055857A8
Authority
WO
WIPO (PCT)
Prior art keywords
dollar
group
aminosulphonyl
benzamides
denotes
Prior art date
Application number
PCT/YU2002/000029
Other languages
French (fr)
Other versions
WO2003055857A1 (en
Inventor
Slobodan Stankovic
Slobodan Mitov
Caslav Stanojevic
Ljiljana Pesic
Original Assignee
Farmaceutsko Hemijska Ind Zdra
Slobodan Stankovic
Slobodan Mitov
Caslav Stanojevic
Ljiljana Pesic
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 Farmaceutsko Hemijska Ind Zdra, Slobodan Stankovic, Slobodan Mitov, Caslav Stanojevic, Ljiljana Pesic filed Critical Farmaceutsko Hemijska Ind Zdra
Priority to AU2002364553A priority Critical patent/AU2002364553A1/en
Publication of WO2003055857A1 publication Critical patent/WO2003055857A1/en
Publication of WO2003055857A8 publication Critical patent/WO2003055857A8/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical

Landscapes

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

Abstract

The simple, new, original and convenient for use, procedure for obtaining of compounds, belonging to the group of $i(heterocyclic aminoalkyl benzamides) of general formula 1, is developed, and/or salts and/or hydrates and/or optical isomers thereof, wherein R1 and R2 denote C1-C4 $i(alkyl) group, R3 denotes an $i(aminosulphonyl) group, denotes a $i(hydrogen) atom or an $i(amino) group, R5 denotes a $i(hydrogen) or a $i(halogen) atom, and and the coefficients $i(m )and $i(n) have value of 1 and/or 2. Of a particular interest in clinical practice are: $i(sulpiride )(RS, R+ or S-)-(5-$i(aminosulphonyl))-N-/(1-$i(ethyl)-2-$i(pyrrolidinyl))$i(methyl)/-2-$i(methoxybenzamide)) and sulmepride (RS, R+ or S-)-(5-($i(aminosulphonyl))-2-$i(methoxy)-N-/-(1-$i(methyl-)2-$i(pyrrolidinyl)methyl/benzamide)). The compounds belonging to this group are used in therapy as: antipsychotics, anti depressives and anti emetics, fungicides, for contraceptive mixtures, in treatment of sterility, as radiopharmaceutical compositions in nuclear medicine, in treatment of migraine of various origins, as well as in treatment of parkinsonism. The advantage of the present invention is in its completely new and simple way to carry out the synthesis of $i(heterocyclic aminoalkyl benzamides )and/or salts and/or hydrates thereof, through reaction of $i(2-alcoxy-5-suiphamoyl-alkyl benzoate )with the corresponding (RS R+ or S-) heterocyclic amine. )Lower temperature of rection and work at atmospheric pressure without catalysts, performing the reaction in cheaper and safer organic solvents, i obtaining the final product which does not require any additional purification, achieving of I good yield and high quality of the final product, cheaper procedure for industrial use and obtaining of the product of high pharmacopeic purity.
PCT/YU2002/000029 2001-12-28 2002-12-27 A process for synthesis of heterocyclic aminoalkyl benzamides WO2003055857A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002364553A AU2002364553A1 (en) 2001-12-28 2002-12-27 A process for synthesis of heterocyclic aminoalkyl benzamides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
YUP093301 2001-12-28
YUP-933/01 2001-12-28

Publications (2)

Publication Number Publication Date
WO2003055857A1 WO2003055857A1 (en) 2003-07-10
WO2003055857A8 true WO2003055857A8 (en) 2003-10-30

Family

ID=25552054

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/YU2002/000029 WO2003055857A1 (en) 2001-12-28 2002-12-27 A process for synthesis of heterocyclic aminoalkyl benzamides

Country Status (2)

Country Link
AU (1) AU2002364553A1 (en)
WO (1) WO2003055857A1 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103772256B (en) * 2012-10-24 2017-10-10 江苏天士力帝益药业有限公司 A kind of preparation method of high-purity Sulpiride or its optical isomer
CN103804265B (en) * 2012-11-08 2018-08-07 江苏天士力帝益药业有限公司 The synthesis of a kind of Sulpiride or its optical isomer and post-processing approach
CN103420887B (en) * 2013-08-30 2014-12-10 孙威 Levosulpiride compound and preparation method thereof
CN105601544A (en) * 2015-12-30 2016-05-25 苏州诚和医药化学有限公司 Synthesis method of 2-methoxyl-5-amino sulfanoylmethyl benzoate
CN112441960B (en) * 2020-12-14 2022-03-01 常州康普药业有限公司 Synthetic method of sulpiride

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3342826A (en) * 1964-01-13 1967-09-19 Ile De France Heterocyclic aminoalkyl benzamides
DE2212340C2 (en) * 1972-03-15 1983-09-22 Quimitecnica S.A., Madrid Process for the preparation of N - [(1-ethyl-2-pyrrolidinyl) methyl] -5-sulfamoyl-o-anisamide
DE2305632A1 (en) * 1972-04-10 1973-10-18 Microsules Argentina Sociedad N-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-5-sulphamoyl - -benzamides - prepd from salicylic acid cpds
FR2245628B1 (en) * 1973-09-28 1977-03-11 Ile De France
IT1070992B (en) * 1973-12-21 1985-04-02 Italfarmaco Spa PROCESS FOR THE PREPARATION OF I ETHYL 2 2 METHOXY 5 SULFAMOIL BENZAMIDOMETHY PYROLIDINE
IT1095415B (en) * 1978-02-16 1985-08-10 Ravizza Spa PROCESS FOR THE PRODUCTION OF AN OPTICALLY ACTIVE BENZAMIDE, OPTICALLY ACTIVE BENZAMIDE SO OBTAINED AND COMPOSITIONS

Also Published As

Publication number Publication date
WO2003055857A1 (en) 2003-07-10
AU2002364553A1 (en) 2003-07-15

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