6-alkenyl and ethynyl derivatives of 2-amino-4-hydroxypyrido[2,3

Details 6-alkenyl and ethynyl derivatives of 2-amino-4-hydroxypyrido[2,3 6-alkenyl and ethynyl derivatives of 2-amino-4-hydroxypyrido[2,3

1988-08-08

1990-02-20

Shah, Mukund J.

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

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

546298, 546341, 560 37, 560 47, 560104, 560117, C07D47104

Patent

active

049027964

ABSTRACT:
2-Amino-4-hydroxy-6-[2-(4-carboxyphenyl)alk-1-en-1-yl]pyrido[2,3,-d]pyrimid ines and 2-amino-4-hydroxy-6-[2-(4-carboxyphenyl)alk-1-yn-1-yl]pyrido[2,3-d]pyrimid ines are prepared through the reaction of a halo-aromatic compound and an unsaturated compound in the prosence of a palladium catalyst. The products are chemical intermediates for the preparation of antineo-plastic agents.
A typical embodiment is the reaction of a protected 2-amino-4-hydroxy-6-ethynylpyrido[2,3-d]pyrimidine and an ester of 4-iodobenzoic acid.

REFERENCES:
patent: 3856959 (1974-12-01), Mead
patent: 4172200 (1979-10-01), Piper et al.
patent: 4369319 (1983-01-01), DeGraw et al.
patent: 4431805 (1985-02-01), Temple et al.
patent: 4432981 (1984-02-01), Lesher et al.
patent: 4460591 (1984-07-01), DeGraw et al.
patent: 4512992 (1985-04-01), Duch et al.
patent: 4526964 (1985-07-01), Temple et al.
patent: 4532241 (1985-07-01), DeGraw et al.
patent: 4536575 (1985-08-01), Temple et al.
patent: 4564616 (1986-01-01), Jones et al.
patent: 4684653 (1987-08-01), Taylor et al.
patent: 4818819 (1989-04-01), Taylor et al.
Moad et al., JACS 101:20, 6068-6076 (9/27/76).
Jahine et al., Ind. J. Chem., 16B, 889-891 (10/78).
Sirotnak et al., Cancer Treat. Rep., 66:2 (2/82).
Troschutz et al., Arch. Pharm. 311, 406-414 (1978).
Temple et al., J. Org. Chem. 47, 761-764.
Taylor et al., J. Org. Chem. 50, 1010-1014 (1985).
Taylor et al., Chem. & Biology of Pteridines (Ed. J. A. Blair), 1983 Walter de Gruyter & Co., N.Y., 115-119.
Taylor et al., J. Org. Chem. 48, 4852-4860 (1983).
Taylor et al., J. Org. Chem. 50, 1005-1010 (1985).
DeGraw et al., J. Heterocycl. Chem. 19, 1461-1463 (1982).
Grivsky et al., J. Med. Chem. 23:3, 327-329 (1980).
Piper et al., J. Med. Chem. 23, 320-321 (1980).
DeGraw et al., J. Med. Chem 17:5, 552-553 (1974).
Elliott et al., J. Med. Chem. 17:5, 553-555 (1974).
Nair, J. Org. Chem., 50, 1879-1884 (1985).
Drugs of the Future, IV, No. 9, 641-644 (1979).
Sirotnak et al., Cancer Treat. Rep. 62:7, 1047-1052 (1978).
Stone et al., Biochem. Pharmac. 33:2, 175-179 (1984).
Srinivasan et al., J. Org. Chem., 45, 3746-3748 (1980).
Hurlbert et al., J. Med. Chem., 11, 703-707 (1968).
Hurlbert et al., J. Med. Chem., 11, 708-710 (1968).
Hurlbert et al., J. Med. Chem., 11, 711-717 (1968).
Rosowsky et al., J. Med. Chem., 17:12, 1272-1276 (1974).
Struck et al., J. Med. Chem., 14:8, 693-695 (1971).
CA 96:104757a (1982) Sirotnak et al.
Taylor et al., J. Med. Chem. 28:7, 914-921 (1985).
DeGraw et al., J. Heterocycl. Chem. 8, 105-110 (1971).
Oakes et al., J. Chem. Soc. (London) 4433 (1956).
Elsager et al., Lectures in Heterocyclic Chemistry, vol. 2, S-97; Supplement to J. Heterocyclic Chem., 11 (1974).
Harrington , Synthetic Approaches to 5-Deaza and 5,10-Dideazafolic Acid Analogs, Ph. D. Dissertation, Princeton U., 1982.
DeGraw et al. (VII), J. Med. Chem., 17:470 (1974).
DeGraw et al., (VIII), J. Heterocyclic Chem., 13:439 (1976).
Smith et al., Biochem, 20: 1241 (1981).
Temple et al., (V), J. Med. Chem. 24: 1254 (1981).
DeGraw et al. (IX), Chem. & Biolog. of Pteridines (Ed. Kisliuk/Brown) 1979 Elsevier, North Holland (229-234).
Srinivasan et al., (II), J. Org. Chem. 46: 1777 (1981).
Srinivasan et al., (III), Tetrahedran Lett. 23:1431 (1982).
DeGraw et al., (X), PCT Application WO85/02844 (Published Jul. 4, 1985).
Wheeler et al., J. Amer. Chem. Soc. 74:4725 (1952).
Kisliuk, R. L., Nature, 188:584 (1960).
Kisliuk et al., (II), J. Biol. Chem. 239: 1900 (1964).
Horwitz et al., J. Med. Chem. 11:907 (1968).
Melpoler et al., J. Org. Chem. 41, No. 2, 1976, 265.
Chalk et al., J. Org. Chem. 41, No. 7, 1976, 1206.
Arai et al., J. Heterocyclic Chem., 15, 351 (1976).
Tamaru et al., (I), Tetrahedron Papers 10, 919 (1978).
Tamaru et al., (II), Tetrahedron, 35, 329 (1979).
Sakamoto et al., Synthesis, 1983, 312.

Affiliated with

Also associated with

Rating

6-alkenyl and ethynyl derivatives of 2-amino-4-hydroxypyrido[2,3 does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with 6-alkenyl and ethynyl derivatives of 2-amino-4-hydroxypyrido[2,3, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and 6-alkenyl and ethynyl derivatives of 2-amino-4-hydroxypyrido[2,3 will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1617067