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7-(Substituted methyl)-3-(substituted thio)-cephalosporins, derivatives and pharmaceutical compositions containing them
| Details |
Inventors: Beattie, Thomas R.; Cama, Lovji D.; Christensen, Burton G.; Dininno, Frank P.;
Assignee: Merck & Co., Inc. (NJ)
Primary Examiner: Daus; Donald G.
Assistant Examiner: Rivers; Diana G.
Attorney, Agent or Firm: Mahon; Frank M., Levitt; Julian S., Arno; James A.
Disclosed are antibiotic 3-(substituted thio)-7-(substituted methyl) cephalosporins, derivatives and analogues thereof; wherein the methyl substituent is, inter alia, hydroxyl, ketonic oxygen, imino nitrogen, amino or mercapto. Also disclosed are processes for the preparation of such compounds and their pharmaceutically acceptable salt, ester and amide derivatives; pharmaceutical compositions comprising such compounds; and methods of treatment comprising administering such compounds and compositions when an antibiotic effect is indicated. |
|
DETAILED DESCRIPTION OF THE INVENTION The following U.
S.
Patents and co-pending, commonly assigned U.
S.
Patent Applications are incorporated herein by reference for the subject matter which they disclose as it relates to the preparation of necessary starting materials needed for a description of the present invention.
It will be noted that these patents and applications disclose the basic nucleii (IIa, IIb, IIc) (and derivatives thereof) upon which the present invention relies:
______________________________________
##STR2##
Y Y'
______________________________________
IIa R NR'R"
IIb SR.
sup.
5 NR'R"
IIc R
##STR3##
______________________________________
wherein all substituents, except R, R' and R" are as previously defined; and R is selected from the group consisting of hydrogen, acyloxymethyl such as acetoxymethyl and carbamoyloxymethyl, and halomethyl for example; and R' and R" are independently selected from the group consisting hydrogen and the acyl radicals known in the bicyclic .
beta.
-lactam antibiotic art.
The incorporated-by-reference materials are: co-pending, commonly assigned, concurrently filed U.
S.
patent applications Ser.
Nos.
634,082 (Beattie, et al.
) and 634,081 (Cama, et al.
) which relate, respectively, to 7-(substituted methyl)cephalosporins and 3-(substituted thio)cephalosporins, and both now abandoned.
With reference to structure I, above-given, the preferred embodiments of the present invention are those wherein: A is selected from S, CH.
sub.
2, O; R.
sup.
1 and R.
sup.
2 are independently selected from hydrogen, alkyl, aryl, such as phenyl, substituted phenyl, and aralkyl such as benzyl, .
beta.
-phenethyl and heteroaralkyl such as 2-thienylmethyl; X is selected from the group consisting of OH, .
dbd.
O, .
dbd.
NH, NH.
sub.
2, SH and NHR.
sup.
7 ; R.
sup.
3 is selected from hydrogen, alkoxy such as methoxy, and lower alkylthio such as methylthio, and halogen such as fluoro and bromo; R
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