Warner-lambert Company

Parke-davis Company

Other

Warner Lambert LLC

Theodore H Haskell

Marland P Hutt, Jr

Thomas F Mich

Leonard Doub

Dietrich Schweiss

James S Kaltenbronn

Ernest D Nicolaides

David Clarkston Baker

Peter W Woo

Peter Wing Kee Woo

Joseph P Sanchez

Townley P Culbertson

Walter E Behnke

William R Marsh

Gin G Huang

Novel organic amide compounds which are N-[[(acylaminoacylamino or aminoacylamino)]-dihydro-oxo-3-quinolinylcarbonyl]cephalosporin compounds having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid of the appropriate cephalosporin or the acid addition salt or silylated derivative or complex thereof with a reactive derivative of the corresponding (acylaminoacylamino or aminoacylamino)dihydro-oxo-3-quinolinecarboxylic acid or (b) reacting the free amino acid 7-aminocephalosporanic acid or a related compound or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding D-N-[(acylaminoacylamino or aminoacylamino)dihydro-oxo-3-quinolinylcarbonyl]-2-substituted glycine. Pharmaceutical compositions containing said compounds and methods for treating infections using said compositions are also disclosed.

Cephalosporins

Novel organic amide compounds which are N-[[(acylaminoacylamino or aminoacylamino9]-dihydro-oxo-3-quinolinylcarbonyl]penicillin compounds having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid of the appropriate penicillin or the acid salt or silylated derivative or complex thereof with a reactive derivative of the corresponding (acylaminoacylamino or aminoacylamino)-dihydro-oxo-3-quinolinecarboxylic acid or (b) reacting the free amino acid 6-aminopenicillanic acid or a related compound or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding D-N-[(acylaminoacylamino or aminoacylamino) dihydro-oxo-3-quinolinycarbonyl]-2-substituted glycine. Pharmaceutical compositions containing said compounds and methods for treating infections using said compositions are also disclosed.

Antibacterial amide compounds, compositions thereof and methods of using

Novel organic amide compounds which are N-[ureidodihydro-oxo-3-quinolinylcarbonyl]penicillin compounds having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid of the appropriate penicillin or the acid salt or silylated derivative or complex thereof with a reactive derivative of the corresponding ureido-dihydro-oxo-3-quinolinecarboxylic acid or (b) reacting the free amino acid 6-aminopenicillanic acid or a related compound or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding D-N-[ureidodihydro-oxo-3-quinolinylcarbonyl]-2-substituted glycine. Pharmaceutical compositions containing said compounds and methods for treating infections using said compositions are also disclosed.

Antibacterial amide compounds, compositions, and methods of use

Novel organic amide compounds which are N-[6-(acylaminophenyl)-1,2-dihydro-2-oxonicotinoyl]penicillin compounds having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid of the appropriate penicillin or the acid salt or silylated derivative or complex thereof with a reactive derivative of the corresponding N-6-[acylaminophenyl]-1,2-dihydro-2-oxonicotinic acid or (b) reacting the free amino acid 6-aminopenicillanic acid or a related compound or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding D-N-[6-[acylaminophenyl]-1,2-dihydro-2-oxonicotinoyl]-2-substituted glycine. Pharmaceutical compositions containing said compounds and methods for treating infections using said compositions are also disclosed.

Antibacterial amide compounds

Novel organic amide compounds which are N-[2-(acylaminophenyl)-4-hydroxy-5-pyrimidinylcarbonyl]penicillin compounds having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid of the appropriate penicillin or the acid salt or silylated derivative or complex thereof with a reactive derivative of the corresponding N-2-(acylaminophenyl)-4-hydroxy-5-pyrimidine carboxylic acid or (b) reacting the free amino acid 6-aminopenicillanic acid or a related compound or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding D-N-[2-(acylaminophenyl)-4-hydroxy-5-pyrimidinylcarbonyl]-2-substituted glycine. Pharmaceutical compositions containing said compounds and methods for treating infections using said compositions are also disclosed.

Antibacterial amide compounds and pharmaceutical compositions containing

Novel organic amide compounds which are N-[6-[(acylaminoacylamino or aminoacylamino)phenyl]-1,2-dihydro-2-oxonicotinyl]cephalosporin compounds having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid of the appropriate cephalosporin or the acid salt or silylated derivative or complex thereof with a reactive derivative of the corresponding N-6-[(acylaminoacylamino or aminoacylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid or (b) reacting the free amino acid 7-aminocephalosporanic acid or a related compound or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding D-N-[6-(acylaminoacylamino or aminoacylamino)phenyl]-1,2-dihydro-2-oxonicotinyl]-2-substituted glycine. Pharmaceutical compositions containing said compounds and methods for treating infections using said compositions are also disclosed.

Aminoacid derivatives of cephalosporin compounds

Novel organic amide compounds which are N-[2-[(acylaminoacylamino or aminoacylamino)phenyl]-4-hydroxy-5-pyrimidinylcarbonyl]cephalosporin compounds having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid of the appropriate cephalosporin or the acid salt or silylated derivative or complex thereof with a reactive derivative of the corresponding N-2-[(acylaminoacylamino or aminoacylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid or (b) reacting the free amino acid 7-aminocephalosporanic acid or a related compound or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding D-N-[2-[(acylaminoacylamino or aminoacylamino)phenyl]-4-hydroxy-5-pyrimidinylcarbonyl]-2-substituted glycine. Pharmaceutical compositions containing said compounds and methods for treating infections using said compositions are also disclosed.

Novel organic amide compounds which are N-[6-[(acylaminoacylamino or aminoacylamino)phenyl]-1,2-dihydro-2-oxonicotinyl] penicillin compounds having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid of the appropriate penicillin or the acid salt or silylated derivative or complex thereof with a reactive derivative of the corresponding N-6-[(acylaminoacylamino or aminoacylamino)-phenyl]-1,2-dihydro-2-oxonicotinic acid or (b) reacting the free amino acid 6-aminopenicillanic acid or a related compound or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding D-N-[6-[(acylaminoacylamino or aminoacylamino) phenyl]-1,2-dihydro-2-oxonicotinyl]-2-substituted glycine. Pharmaceutical compositions containing said compounds and methods for treating infections using said compositions are also disclosed.

Antibacterial amide compounds and means for using the same

Novel organic amide compounds which are N-[2-[(acylaminoacylamino or aminoacylamino)phenyl]-4-hydroxy-5-pyrimidinylcarbonyl] penicillin compounds having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid of the appropriate penicillin or the acid salt or silylated derivative or complex thereof with a reactive derivative of the corresponding N-2-[(acylaminoacylamino or aminoacylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid or (b) reacting the free amino acid of 6-aminopenicillamic acid or a related compound or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding D-N-[2-[(acylaminoacylamino or aminoacylamino)phenyl]-4-hydroxy-5-pyrimidinylcarbonyl]-2-substituted glycine. Pharmaceutical compositions containing said compounds and methods for treating infections using said compositions are also disclosed.

Novel antibacterial amide compounds and process means for producing the

O-2,6-Diamino-2,3,6-trideoxy-.alpha.-D-ribo-hexopyranosyl-(1.fwdarw.4)-O-�. beta.-D-xylofuranosyl-(1.fwdarw.5)!-N.sup.1 -�(S)-4-amino-2-hydroxy-1-oxobutyl!-2-deoxystreptamine, also known as 3'-deoxybutirosin A and acid addition salts of said compound. These compounds exhibit a wide spectrum of antibacterial activity. The above compounds are produced by the reduction of a tetra-N-protected-3'-arylthio-3'-deoxybutirosin A compound having the formula: ##STR1##

Production of 3'-deoxybutirosina A

Novel organic amide compounds which are N-[6-[(aminosulfonyl)phenyl]-1,2-dihydro-2-oxonicotinyl]penicillin and cephalosporin type compounds having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid of the appropriate penicillin or cephalosporin or the acid salt or silylated derivative or complex thereof with a reactive derivative of the corresponding N-6-[(aminosulfonyl)phenyl]-1,2-dihydro-2-oxonicotinic acid or (b) reacting the free amino acid 6-aminopenicillanic acid, 7-aminocephalosporanic acid, 7-amino-3-methylceph-3-em-4-carboxylic acid or a related compound or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding D-N-[6-[(aminosulfonyl)phenyl]-1,2-dihydro-2-oxonicotinyl]-2-substituted glycine. Pharmaceutical compositions containing said compounds and methods for treating infections using said compositions are also disclosed.

[Amino sulfonyl-2-oxo-nicotinyl]derivatives of cephalosporin

Process for the production of an ester product, 9-(.beta.-D-arabinofuranosyl)adenine, 5'-phosphate, in which the mixture resulting from reaction of 9-(.beta.-D-arabinofuranosyl)adenine with phosphorylating agent in trialkyl phosphate solvent is subjected to aqueous hydrolysis, the pH of the hydrolysis mixture is adjusted upward sufficiently to cause separation into aqueous and non-aqueous liquid phases, the trialkyl phosphate solvent is removed, and the product is precipitated from the residual aqueous mixture and isolated.

Process for the production of 9-(.beta.-D-arabinofuranosyl)adenine,

Novel organic amide compounds which are N-[6-[(aminosulfonyl)phenyl]-1,2-dihydro-2-oxonicotinyl]penicillin and cephalosporin type compounds having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid of the appropriate penicillin or cephalosporin or the acid salt or silylated derivative or complex thereof with a reactive derivative of the corresponing N-6-[(aminosulfonyl)phenyl]-1,2-dihydro-2-oxonicotinic acid or (b) reacting the free amino acid 6-aminopenicillanic acid, 7-aminocephalosporanic acid, 7-amino-3-methylceph-3-em-4-carboxylic acid or a related compound or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding D-N-[6-[(aminosulfonyl)phenyl]-1,2-dihydro-2-oxonicotinyl]-2-substituted glycine. Pharmaceutical compositions containing said compounds and methods for treating infections using said compositions are also disclosed.

9-(5-O-Acyl-.beta.-D-arabinofuranosyl)adenine compounds and their production by reacting 9-(.beta.-D-arabinofuranosyl)adenine with a reactive derivative of an alkanoic acid. The compounds are useful as antiviral agents. The compounds are water-soluble and lipophilic, thereby being adaptable to a wide variety of pharmaceutical formulations.

9-(5-O-Acyl-.beta.-D-arabinofuranosyl)adenine compounds

9-(3-O-Acyl-.beta.-D-arabinofuranosyl)adenine compounds, 9-(2,3-di-O-acyl-.beta.-D-arabinofuranosyl)adenine compounds, and their production by reacting in each case the corresponding 5-silyl ether derivative with a tetraalkylammonium fluoride. The compounds are useful as antiviral agents. The compounds are water-soluble and lipophilic, thereby being adaptable to a wide variety of pharmaceutical formulations.

Growing community of inventors

Ann Arbor, MI, United States of America

Theodore H Haskell