Pharmaceutically active benzoquinazoline compounds

Details Pharmaceutically active benzoquinazoline compounds Pharmaceutically active benzoquinazoline compounds

1993-01-13

2000-07-18

Bernhardt, Emily

Organic compounds -- part of the class 532-570 series

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

544246, 544249, C07D23970

Patent

active

060909412

ABSTRACT:
Compounds of the formula (I) or salts thereof, ##STR1## wherein the dotted line represents a single or double bond, R.sup.1 is alkyl or amino optionally substituted by alkyl, alkanoyl or benzyl group: R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are the same or different and each is selected from hydrogen, phenyl, halo, nitro, a group S(O).sub.n R.sup.8 wherein n is the integer 0, 1 or 2 and R.sup.8 is halo or alkyl or a group NR.sup.9 R.sup.10 are both hydrogen, a group NR.sup.11 R.sup.12 wherein R.sup.11 and R.sup.12 are the same or different and each is hydrogen or alkyl, a group OR.sup.13 wherein R.sup.13 is hydrogen or C.sub.1-4 alkyl substituted by halo; a C.sub.1-4 aliphatic group optionally substituted by a group OR.sup.14 or NR.sup.14 R.sup.15 wherein R.sup.14 and R.sup.15 are the same or different and each is hydrogen or alkyl; ot two of R.sup.2 to R.sup.5 are linked together to form a benzp group, one of R.sup.2 to R.sup.3 is a group X--Y--R.sup.16 wherein X is CH.sub.2, NR.sup.17, CO, or S(O).sub.m and Y is CH.sub.2, NR.sup.17, O or S(O).sub.m, or X--Y is CH.sub.2,NR.sup.17, --CH.dbd.CH-- or --N.dbd.N--, are disclosed as pharmacological agents useful in the treatment of tumors. Pharmaceutical compositions and methods for the preparation of compounds of formula (I) are also disclosed.

REFERENCES:
patent: 4564616 (1986-01-01), Jones et al.
patent: 4814335 (1989-03-01), Kim
Hughes et al., "Replacement of the para-Aminobenzoyl Portion of a Series of C2-Desamino C2-Methyl-Dideazafolic Acid Derivatives: Effect on Thymidylate Synthase (TS) Inhibition and Cytotoxicity", Poster at the 1989 AACR Meeting.
Marsham et al., "Quinazoline Antifolate Thymidylate Sunthase Inhibitors: Nitrogen, Oxygen, Sulfur, and Chlorine Substituents in the C2 Position", J. Med. Chem. 32, 569-575 (1989).
"Thymidylate Synthase (TS) Inhibitory and Cytoxic Activity of a Series of C2 Substituted 5,8-deazafolates", Poster at the 1988 AACR Meeting, Marsham et al.
Jones et al., "Quinazoline Antifolates Inhibiting Thymidylate Synthase: Variation of the Amino Acid", J. Med. Chem., 29 1114-1118 (1986).
Jones et al., "Quinazoline Antifolates Inhibiting Thymidylate Synthase: Variation of the N.sup.10 Substituent", J. Med. Chem., 28, 1468-1476 (1985).
Jones, et al., Quinazoline Antifolates Inhibiting Thymidylate Synthase: Benzoyl Ring Modifications, J. Med. Chem., 1986, 29, pp. 468-472.
Marsham, P.R., et al., Quinazoline Antifolate Thymidylate Synthase Inhibitors: Bridge Modifications and Conformationally Restricted Analogues in the C2-Methyl Series, J. Med. Chem., 1991, 34, pp. 2209-2218.
The Pyrinidines by D.J. Brown, pp. 31-32, 44-50 (1962).

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