Synthesis of antiulcer compounds

Details Synthesis of antiulcer compounds Synthesis of antiulcer compounds

1990-05-22

1991-07-09

Raymond, Richard L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

544390, 546197, 546226, 548342, 548538, 549441, 549494, 549495, 564 47, 564 58, 564252, C07D40712

Patent

active

050307380

ABSTRACT:
To synthesize molecules with antiulcer action, specifically ranitidine, niperotidine and cimetidine, having the formula: ##STR1## wherein R.sub.1 is hydrogen or together with R.sub.2 represents the rest of a cycloaliphatic or heterocyclic optionally substituted ring with 5 or 6 carbon atoms, R.sub.2 represents H, alkyl, alkyl substituted with a simple or substituted aromatic ring or with a single or substituted heterocyclic ring, Ar represents a simple or substituted phenyl group, a simple or substituted heterocyclic aromatic group, N=1, 2, 3, 4, 5 or 6 and X represents CH--NO.sub.2, S, N--C.tbd.N, the compound (II) is prepared through the following process sequence: ##STR2## wherein Z=H, NO.sub.2, halogen and R.sub.3 =--(CH.sub.2).sub.n Ar, --(CH.sub.2).sub.n --SH, --(CH.sub.2).sub.n --S--S--(CH.sub.2).sub.n, --(CH.sub.2).sub.n --S--CH.sub.2 Ar Y being halogen.
The urea of formula ##STR3## is converted in a first stage into the corresponding carbodiimide ##STR4## by reaction with triphenylphosphine and bromine in the presence of a strong base and in a second stage is obtained the desired compound by reaction with nitromethane or with a saline derivative of cynamide.

REFERENCES:
patent: 3957774 (1976-05-01), Kolopissis et al.
patent: 4279819 (1981-07-01), Price et al.
patent: 4399294 (1983-08-01), Bays et al.
Moimas et al., Synthesis, No. 5 (1985), pp. 509-510.
Palomo et al., Chemical Abstracts, vol. 94 (1981), 46808m.
Kraemer et al., Chemical Abstracts, vol. 105 (1986), 114,968p.

Affiliated with

Also associated with

Rating

Synthesis of antiulcer compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Synthesis of antiulcer compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthesis of antiulcer compounds will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-619238