Abstract: Disclosed are 3- and 6-substituted 7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acids having the structure: ##STR1## wherein R.sup.6, R.sup.7 and R.sup.8 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl. Such compounds as well as their pharmaceutically acceptable salt, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.

Abstract: Disclosed are 3-substituted-6-(1'-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-ca rboxylic acids having the structure: ##STR1## wherein R.sup.8 is, inter alia, selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl. Such compounds as well as their pharmaceutically acceptable O- and carboxyl derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.

Abstract: A process is provided which yields derivatives of cephalosporins and penicillins. The process starts with 7-aminodecephalosporanic acid or 6-APA and reacts with a carbonyl containing compound to form a Schiff's base (imino) adduct. This latter compound is then treated with a defined reactant yielding a novel Schiff's base adduct having a side chain on the carbon adjacent to the imino-nitrogen. The amino moiety can be regenerated and further reacted to form end compounds which are active against both gram-positive and gram-negative bacteria.

Abstract: Disclosed are 3-(2-aminoethylthio)-6-amido-7-oxo-1-azabicyclo [3.2.0]hept-2-ene-2-carboxylic acids having the structure: ##STR1## wherein R.sup.1 is hydrogen or acyl. Such compounds as well as their pharmaceutically acceptable salt, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.

Abstract: Disclosed are S-oxides of 3-substituted thio-6-amido-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acids having the structure: ##STR1## wherein: n is 1 or 2; R.sup.1 is hydrogen or acyl; and R.sup.8 is, inter alia, independently selected from the group consisting of alkyl, alkenyl, aryl and aralkyl. Such compounds as well as their pharmaceutically acceptable salt, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.

Abstract: Disclosed are 2-, 5- and 6-substituted-1-carbadethiapen-2-em-3-carboxylic acids having the structure: ##STR1## wherein R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are, inter alia, independently selected from the group consisting of hydrogen, (R.sup.9 is not hydrogen), alkyl, alkenyl, aryl and aralkyl. Such compounds, as well as their pharmaceutically acceptable salt, ester and amide derivatives, are useful as antibiotics. Also disclosed are processes for the preparation of such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.

Abstract: Antibiotic 5-substituted-3-(2-aminoethylthio)-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo[3 .2.0]hept-2-ene-2-carboxylic acids (I) are disclosed: ##STR1## wherein R is alkyl, cycloalkyl, cycloalkylalkyl, aryl, aralkyl or heteroaryl.

Abstract: Novel cephalosporin compounds having a substituted or unsubstituted vinyl group at the 3-position are prepared by the reaction of a phosphoranylidene compound with a compound containing a carbonyl group. The novel cephalosporin compounds are active against a range of gram-negative and gram-positive microorganisms and are of value in human and veterinary medicine.

Abstract: Isomeric forms of 3-(2-aminoethylthio)-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-en e-2-carboxylic acid (I) ##STR1## are disclosed; also disclosed is a process for their total synthesis; such isomers individually, and as mixtures, are useful as antibiotics.

Abstract: Disclosed are 3-(2-aminoethylthio)-6-amido-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxy lic acids having the structure: ##STR1## wherein R.sup.1 is hydrogen or acyl. Such compounds as well as their pharmaceutically acceptable salt, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.

Abstract: A method of preparing a compound of the formula: ##STR1## where Formula (I) may also have the structure of partial Formula (III); wherein, ##STR2## R' is hydrogen or methyl; R" is hydrogen or .beta.-methyl;R'" is .beta.-methyl or hydroxy;Z is (1) oxo;(2) .beta.-hydrogen and .alpha.-hydroxy; or .alpha.-hydrogen or .alpha.-hydroxyl and(3) (Y).sub.n Q where n=0 or 1, Y is a straight or branched hydrocarbon chain of 1 to 12 carbon atoms andQ is ##STR3## where R.sup.8 is, ##STR4## where the dashed bond replaces the 17.alpha. hydrogen; (6) cyano; or(7) tetrazolyl;and pharmaceutically acceptable salts of the above compounds;CHARACTERIZED IN THAT(I.) a compound of the formula: ##STR5## , where A has the meanings above except --CH.dbd.CH--, is (1) treated with an oxidizing agent at reduced temperatures to form the corresponding 5-oxo-3,5-seco-androstan-3-oic acid compound;(2) treating the product of step (1) with an amine of formula: R.sup.1 NH.sub.

Abstract: Disclosed are 3-substituted thio-6-amido-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acids having the structure: ##STR1## wherein: R.sup.1 is hydrogen or acyl and R.sup.8 is, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl. Such compounds as well as their pharmaceutically acceptable salt, ester and amide derivatives are useful as antibiotics. Also disclosed are processes for the preparation of such compounds, pharmaceutical compositions comprising such compounds and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated.

Abstract: Amides of 17.beta.-carboxy-4-androsten-3-one having the formula: ##STR1## where R.sup.1 and R.sup.2 are hydrogen (only one may be hydrogen), C.sub.1-4 alkyl, cyclo C.sub.5-6 alkyl, phenyl, or together with the nitrogen are a 5 or 6 membered heterocycle with up to one other heteroatom selected from oxygen and nitrogen; R.sup.3, R.sup.4, R.sup.5, and R.sup.6 are hydrogen or C.sub.1-3 alkyl; R.sup.7 is hydrogen or cyano; Z is oxygen, N-R.sup.8 where R.sup.8 is C.sub.1-3 alkyl, or CH--R.sup.9 where R.sup.9 is hydrogen, .alpha.-fluoro, or .alpha.-C.sub.1-3 alkyl,active as testosterone 5.alpha.-reductase inhibitors, and thus useful topically for treatment of acne, seborrhea, female hirsutism and male pattern baldness.

Abstract: A process for preparing 17.beta.-carboxy-4-androsten-3-ones comprising the steps of (1) reacting a 17.beta.-(1-ketoethyl)-5-androsten-3-ol, for example, pregnenolene, with pyridine and iodine to form a pyridinium iodide compound; (2) reacting the pyridinium iodide compound with alkali metal methoxide in methanol to form a methyl-5-androsten-3-ol-17.beta. carboxylate; (3) oxidizing the product of Step (2) preferably with aluminum isopropoxide to form methyl-4-androsten-3-one-17.beta.-carboxylate; and (4) hydrolyzing the product of Step (3) to the corresponding 17.beta.-carboxylic acid, salt, or ester. The 17.beta.-carboxy-4-androsten-3-ones are useful as intermediates for preparation of N-substituted-17.beta.-carbamoylandrost-4-en-3-one and 4-aza-17.beta.-substituted-5.alpha.-androstan-3-one 5.alpha. reductase inhibitors.

Abstract: Amides and thioates of (-)(cis-1,2-epoxypropyl)-phosphonic acid and phosphonothioic acid are prepared by converting (-)(cis-1,2-epoxypropyl)phosphonic acid or phosphonothioic acid or a salt thereof to an acid halide and reacting the acid halide with an amine, and by reacting the phosphonic acid or a salt thereof with an amine in the presence of a carbodiimide. The novel (-)(cis-1,2-epoxypropyl)phosphonic and phosphonothioic amides are active antibacterial agents.