4 (2 Aminoethyl)Benzenesulfonamide

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Chemical

Glibenclamide

5-chloro-N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxybenzamide

Product :

name :

Development code :

Owner :

RN :

Boehringer Mannheim

Mp Bp :

Gen. Form. : C23H28ClN3O5S

10238-21-8

MW :

Producer :

Reactions :Phosgene

References :

Uses : Antidiabetic

Launching date :Priority date :

Other names :

Update :

Brand :

1966

Azuglucon (Azupharma: Germany)

Bastiverit (Bastian-Werk: Germany)

Calabren (Berk: UK)

Daonil (Hoechst: Australia, Belgium, Eire, Italy, Netherlands, Norway, South Africa, Spain, Sweden,

Switzerland, UK); (Hoechst Houde: France)

Dia-BASF (BASF Generics: Germany)

Diabeta (HMR: USA)

Dia-Eptal (Montavit: Austria)

Duraglucon-N (Durachemie: Germany)

Euglucan (Boehringer Mannheim: France)

Euglucon (Boehringer Mannheim: Australia, Austria, Belgium, Canada, Germany, Italy, Netherlands,

Norway, South Africa, Spain, Sweden, Switzerland); (Roussel: Eire, UK)

Gen-Glybe (Genpharm: Canada)

Gewaglucon (Nycomed: Austria)

Gilemal (Enzypharm: Austria)

Glucolon (Sabater: Spain)

Gli-Basan (Schonenberger: Switzerland)

Gliben (Gentili: Italy); (ct-Arzneimittel: Germany)

Glibenbeta (Betapharm: Germany)

Glibenclamid (R.A.N.-Pharm: Germany); (3M Medica: Germany); (Heumann: Germany); (Aliud Pharma:

Germany); (Basics Pharma: Germany); (Ratiopharm: Germany)

Glibenhexal (Hexal: Germany)

Gliben-Puren N (Isis Puren: Germany)

13/08/2015(C) Becker Associates 1999

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Glibesifar (Siphar: Switzerland)

Glibetic (Teva: Israel)

Gliboral (Guidotti: Italy)

Glidanil (Montpellier: Argentina)

Glimidstada (Stada: Germany)

Glucobene (Merckle: Austria)

Glucolon (Sabater: Spain)

Gluconorm (Wolff: Germany)

Glucoremed (Lichtenstein: Germany)

Gluco-Tablinen (Sanorania: Germany)

Glucoven (Chinoin: Mexico)

Glukoreduct (Sanofi Winthrop: Germany)

Glukovital (Wolff: Germany)

Glyben (Rolab: South Africa)

Glycolande N (Synthelabo: Germany)

Glynase (Upjohn: USA)

Hemi-Daonil (Hoechst Houde: France); (Hoechst: Netherlands)

Humedia (APS: Germany)

Lisaglucon (Farmasa: Brazil)

Maninil (Berlin-Chemie: Germany)

Melix (Pharmador: South Africa); (Lagap: Switzerland)

Micronase (Upjohn: USA)

Miglucan (Boehringer Mannheim: France)

Neogluconin (Waldheim Pharmazeutika: Austria)

Normoglucon (Klinge: Austria)

Praeciglucon (Boehringer Mannheim: Germany)

Semi-Daonil (Hoechst: Austria, Eire, South Africa, Switzerland, UK)

Semi-Englucon (Boehringer Mannheim: Austria, Netherlands, Switzerland); (Hoechst: Austria)

Semi-Gliben-Puren (Isis Puren: Germany)

Market : launched

Comments :

Intermediates:I phenylacetonitrile

II 4-(chlorosulfonyl)benzeneacetonitrile

III 4-(cyanomethyl)benzenesulfonamide

IV 4-(2-aminoethyl)benzenesulfonamide

V 5-chloro-2-methoxybenzoic acid

VI 5-chloro-N-[2-[4-(aminosulfonyl)phenyl]ethyl]-2-methoxybenzamide

VII cyclohexyl isocyanate

VIII 5-chlorosalicylic acid

Reaction Sequences :


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Chemical

Glipizide

N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-5-methylpyrazinecarboxamide

Product :

name :

Development code :

Owner :

RN :

Carlo Erba

Mp Bp :

Gen. Form. : C21H27N5O4S

29094-61-9

MW :

Producer :

Reactions :Phosgene

References :Ger Offen DE 2,012,138 (1970), IT Appl. 26 Mar 1969 (Carlo Erba)

Uses : Antidiabetic


Other names :

Update :

Brand :

1970

Glibenese (Pfizer: Austria, France, Germany, Netherlands, Spain, Switzerland, UK)

Glutotrol (Pfizer: USA)

Melizid (Medica: Finland)

Minibetic (Ikapharm: Israel)

Minidiab (Farmitalia Carlo Erba: Norway); (Pharmacia: Sweden); (Pharmacia & Upjohn: France)

Minodiab (Pharmacia & Upjohn: UK)

Ozidia (Pfizer: France)

Market : launched

Comments :

Intermediates:I chloroacetone

II ammonia

III 2,5-dimethylpyrazine

IV 5-methyl-2-pyrazinecarboxylic acid

V 5-methyl-2-pyrazinecarbonyl chloride

VI 4-(2-aminoethyl)benzenesulfonamide

VII N-[2-[4-(aminosulfonyl)phenyl]ethyl]-5-methylpyrazinecarboxamide

VIII cyclohexyl isocyanate

IX phenylacetonitrile

X 4-(chlorosulfonyl)benzeneacetonitrile

XI 4-(cyanomethyl)benzenesulfonamide



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Chemical

Gliquidone

N-[(cyclohexylamino)carbonyl]-4-[2-(3,4-dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isoquinolinyl)ethyl]benzenesulfonamide

Product :

name :

Development code :

Owner :

RN :

Boehringer Ingelheim

Mp Bp :


33342-05-1

MW :

Producer :

Reactions :Phosgene

References :U.S. US 4,523,023 (1985), DE Appl. 3,306,200, 23 Feb. 1983 (Haarmann & Reimer)

U.S. US 3,708,486 (1973), DE Appl. 19,19,570, 17 Apr. 1969 (Boehringer Ingelheim)

Uses : Antidiabetic


Other names :

Update :

Brand :

1969

Glurenor (Guidotti: Italy)

Glurenor (Europharma: Spain)

Glurenorm (Bender: Austria); (Menarini: Belgium); (Yamanouchi: Germany); (Sanofi Winthrop: UK)

Market : launched

Comments :

Intermediates:I 1,2,3,4-tetrahydro-2,4,4-trimethylisoquinoline-1,3-dione

II 1,2,3,4-tetrahydro-2,4,4-trimethyl-7-nitroisoquinoline-1,3-dione

III 7-amino-1,2,3,4-tetrahydro-2,4,4-trimethylisoquinoline-1,3-dione

IV (3,4-dihydro-2,4,4-trimethyl-1,3-dioxo-1H-isoquinolin-7-yl)diazonium chloride

V 7-hydroxy-1,2,3,4-tetrahydro-2,4,4-trimethylisoquinoline-1,3-dione

VI 1,2,3,4-tetrahydro-7-methoxy-2,4,4-trimethylisoquinoline-1,3-dione

VII 7-methoxy-4,4-dimethyl-1H-benzo[c]pyran-1,3(4H)-dione

VIII 4-(2-aminoethyl)benzenesulfonamide

IX 4-[2-(3,4-dihydro-7-methoxy-4,4-dimethyl-1,3-dioxo-2(1H)-isoquinolinyl)ethyl]benzenesulfonamide

X cyclohexyl isocyanate

XI benzeneacetonitrile

XII 4-(cyanomethyl)benzenesulfonyl chloride

XIII 4-(cyanomethyl)benzenesulfonamide



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Chemical

Glisentide

N-[2-[4-[[[(cyclopentylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxybenzamide

Product :

name :

Development code :

Owner :

RN :

Uriach

Mp Bp :


32797-92-5

MW :

Producer :

Reactions :Phosgene

References :

Uses : Antidiabetic


Other names :

Update :

Brand :

1970

Staticum (Uriach: Spain)

Market : launched

Comments :

Intermediates:I phenylacetonitrile

II 4-(chlorosulfonyl)benzeneacetonitrile

III 4-(cyanomethyl)benzenesulfonamide

IV 4-(2-aminoethyl)benzenesulfonamide

V 2-methoxybenzoyl chloride

VI N-[2-[4-(aminosulfonyl)phenyl]ethyl]-2-methoxybenzamide

VII cyclopentyl isocyanate

VIII 2-methoxybenzoic acid



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Chemical

Glisolamide

N-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-5-methyl-3-isoxazolecarboxamide

Product :

name :

Development code :

Owner :

RN :

IFI

Mp Bp :


24477-37-0

MW :

Producer :

Reactions :Phosgene

References :

Uses : Antidiabetic


Other names :

Update :

Brand :

1967

Diabenor (IFI: Italy)

Market : launched

Comments :

Intermediates:I acetone

II oxalic acid diethyl ester

III 2,4-dioxopentanoic acid ethyl ester

IV hydroxylamine

V 5-methyl-3-isoxazolecarboxylic acid ethyl ester

VI 5-methyl-3-isoxazolecarboxylic acid

VII 5-methyl-3-isoxazolecarbonyl chloride


IX N-[2-[4-(aminosulfonyl)phenyl]ethyl]-5-methyl-3-isoxazolecarboxamide

X cyclohexyl isocyanate

XI phenylacetonitrile

XII 4-(chlorosulfonyl)benzeneacetonitrile

XIII 4-(cyanomethyl)benzenesulfonamide



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Chemical

Glisoxepide

N-[2-[4-[[[[(hexahydro-1H-azepin-1-yl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-5-methyl -3-isoxazolecarboxamide

Product :

name :

Development code :

Owner :

RN :

Bayer

Mp Bp :


25046-79-1

MW :

Producer :

Reactions :

References :

Uses : Antidiabetic


Other names :

Patent InformationUpdate :

Brand :

1969

Pro-Diaban (Bayer: Austria, Germany)

Market : launched

Comments :

Intermediates:I acetone

II oxalic acid diethyl ester

III 2,4-dioxopentanoic acid ethyl ester

IV hydroxylamine

V 5-methyl-3-isoxazolecarboxylic acid ethyl ester

VI 5-methyl-3-isoxazolecarboxylic acid

VII 5-methyl-3-isoxazolecarbonyl chloride


IX N-[2-[4-(aminosulfonyl)phenyl]ethyl]-5-methyl-3-isoxazolecarboxamide

X chloroformic acid methyl ester

XI N-[2-[4-[[(methoxycarbonyl)amino]sulfonyl]phenyl]ethyl]-5-methyl-3-isoxazolecarboxamide

XII 1-aminohexahydroazepine

XIII phenylacetonitrile

XIV 4-(chlorosulfonyl)benzeneacetonitrile

XV 4-(cyanomethyl)benzenesulfonamide

XVI epsilon-caprolactam

XVII hexahydro-1H-azepine

XVIII hexahydro-1-nitroso-1H-azepine



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4 (2 Aminoethyl)Benzenesulfonamide

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