Carroll G Temple

US Patent:

44501609, May 22, 1984

Filed:

Mar 3, 1982

Appl. No.:

6/354164

Inventors:

Carroll G. Temple - Birmingham AL
John A. Montgomery - Birmingham AL
Robert D. Elliott - Birmingham AL
Glynn P. Wheeler - Birmingham AL

Assignee:

Southern Research Institute - Birmingham AL

International Classification:

C07D47104
C07D21375

US Classification:

424250

Abstract:

1,2-Dihydropyrido[3,4-b]pyrazines are provided which possess antifungal and anticancer activity. The compounds have the structure: ##STR1## wherein x has a value of 1, 2 or 3; R. sub. 1 is a lower alkyl group, R. sub. 2 is a member selected from the group consisting of hydrogen, alkyl radicals having from about one to about 12 carbon atoms, alkenyl radicals having from about two to about 15 carbon atoms, cycloalkyl radicals having from about three to about 20 carbon atoms, aralkyl and alkaryl radicals having from about six to about 20 carbon atoms, a halogen radical, provided that when x has a value of 1 and R. sub. 2 is in the para position and R. sub. 3 and R. sub. 4 are both hydrogen, R. sub. 2 is not chlorine; a hydroxyl group; an amino group; an alkoxy or aryloxy group; a carboxyl group or an alkylcarboxyl group having from about one to about 10 carbon atoms, an alkylthio group or an arylthio group having from about one to about 20 carbon atoms, a sulfonic acid group or alkyl- or arylsulfonyl group having from about one to about 20 carbon atoms, an alkyl- or arylsulfinyl group having from about one to about 20 carbon atoms, an alkyl- or aryl mono- or diamino group having from about one to about 20 carbon atoms, a hydrocarbyl group, such as defined above, carrying halogen, hydroxyl, amino, alkoxy or aryloxy; and, when taken together with the aromatic ring to which it is attached, a fused ring structure such as naphthyl; and R. sub. 3 and R. sub. 4 are either both hydrogen or one is hydrogen and the other is a lower alkyl group.

US Patent:

46007164, Jul 15, 1986

Filed:

Mar 28, 1985

Appl. No.:

6/716945

Inventors:

Carroll G. Temple - Birmingham AL
John A. Montgomery - Birmingham AL
Robert D. Elliott - Birmingham AL
Glynn P. Wheeler - Birmingham AL

Assignee:

Southern Research Institute - Birmingham AL

International Classification:

A61K 31495
C07D47104
C07D21361

US Classification:

514249

Abstract:

1,2-Dihydropyrido[3,4-b]pyrazines are provided which possess anticancer activity. The compounds have the structure: ##STR1## wherein Y is CH. sub. 2 or N(CH. sub. 3); R. sub. 1 is a lower alkyl group; e. g. , an alkyl group containing up to six carbon atoms such as methyl, ethyl, propyl, butyl, etc. ; R. sub. 2 is a member selected from the group consisting of hydrogen, CH. sub. 3 O or Cl; and R. sub. 3 and R. sub. 4 are either both hydrogen or one is hydrogen and the other is a lower alkyl group.

US Patent:

44318057, Feb 14, 1984

Filed:

Jan 11, 1982

Appl. No.:

6/338542

Inventors:

Carroll G. Temple - Birmingham AL
John A. Montgomery - Birmingham AL
Robert D. Elliott - Birmingham AL

Assignee:

Southern Research Institute - Birmingham AL

International Classification:

C07D47104
A61K 31505
C07D48704

US Classification:

544279

Abstract:

There is disclosed a novel intermediate useful in the preparation of pyrido[2,3-d]pyrimidines, which includes N-[4- [(2-amino-4(3H)-oxopyrido[2,3-d]pyrimidin-6-yl)methylamino]benzoyl]-L-glut amic acid (5-deazafolic acid), N-[4-[[(2-amino-4(3H)-oxopyrido[2,3-d]-pyrimidin-6-yl)methyl]methylamino]b enzoyl]-L-glutamic acid (5-deaza-N. sup. 10 -methylfolic acid), N-[4-[(2,4-diaminopyrido[2,3-d]pyrimidin-6-yl)methylamino]benzoyl]-L-gluta mic acid (5-deazaaminopterin), and N-[4-[[(2,4-diaminopyrido[2,3-d]pyrimidin-6-yl)methyl]methylamino]benzoyl] -L-glutamic acid (5-deazamethotrexate). This intermediate is the compound 2,4-diaminopyrido[2,3-d]pyrimidine-6-carboxaldehyde.

US Patent:

45117217, Apr 16, 1985

Filed:

Jan 17, 1984

Appl. No.:

6/571500

Inventors:

Carroll G. Temple - Birmingham AL
John A. Montgomery - Birmingham AL
Robert D. Elliott - Birmingham AL
Glynn P. Wheeler - Birmingham AL

Assignee:

Southern Research Institute - Montgomery AL

International Classification:

C07D21376
C07D21375

US Classification:

546308

Abstract:

Compounds of the formulas ##STR1## where the substituents are as defined within are disclosed as intermediates to make antifungal 1,2-Dihydropyrido[3,4-b]pyrazines.

US Patent:

44516509, May 29, 1984

Filed:

Oct 26, 1982

Appl. No.:

6/436667

Inventors:

Carroll G. Temple - Birmingham AL
John A. Montgomery - Birmingham AL
Robert D. Elliott - Birmingham AL
Glynn P. Wheeler - Birmingham AL

Assignee:

Southern Research Institute - Birmingham AL

International Classification:

C07D49804
C07D51304

US Classification:

544105

Abstract:

There are disclosed certain 2H-pyrido[4,3-b][1,4]oxazines and 2H-pyrido[4,3-b][1,4]thiazines which possess biological activity. The compounds have the structure: ##STR1## wherein n has a value of 1,2 or 3; X is oxygen or sulfur; R. sub. 1 is a lower alkyl group, e. g. , an alkyl group containing up to six carbon atoms such as methyl, ethyl, propyl, butyl, etc. ; R. sub. 2 is a member selected from the group consisting of hydrogen, alkyl radicals having from about one to about 12 carbon atoms, preferably from about one to about six carbon atoms; alkenyl radicals having from about two to about 15 carbon atoms; preferably from about two to about 10 carbon atoms; cycloalkyl radicals having from about three to about 20 carbon atoms, preferably from about three to about 15 carbon atoms; aryl, aralkyl and alkaryl radicals having from about six to about 20 carbon atoms, preferably from about six to about 15 carbon atoms; a halogen radical, e. g. , chlorine, fluorine, bromine and iodine; a hydroxyl group; an amino group; an alkoxy or aryloxy group; a carboxyl group or an alkylcarboxyl group having from about one to about 10 carbon atoms, preferably from about one to about five carbon atoms; an alkythio group or an arylthio group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; a sulfonic acid group or alkyl- or arylsulfonyl group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; an alkyl- or arylsulfinyl group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; an alkyl- or aryl mono- or diamino group having from about one to about 20 carbon atoms, preferably from about one to about 15 carbon atoms; a hydrocarbyl group, such as defined above, carrying halogen, hydroxyl, amino, alkoxy or aryloxy; when taken together with the aromatic ring to which it is attached, a fused ring structure such as naphthyl; and, when taken together with R. sub. 3, an alkylene radical containing from about one to about 12 carbon atoms, preferably from about one to about six carbon atoms; R. sub.

US Patent:

49507613, Aug 21, 1990

Filed:

Jun 2, 1989

Appl. No.:

7/360520

Inventors:

Carroll G. Temple - Birmingham AL

Assignee:

Southern Research Institute - Birmingham AL

International Classification:

C07D21376

US Classification:

546308

Abstract:

The (2S)-(-)-isomer of (5-amino-1,2-dihydro-2-methyl-3-phenylpyrido[3,4-b]pyrazin-7-yl)carbamic acid, ethyl ester is significantly more potent than either the (2R)-(+)-isomer or the (R,S)-(. +-. )-racemic mixture in inhibiting mitotic cell division of L1210 leukemia cells. The compound, pharmaceutical compositions containing the compound, and a method of ameliorating cancer diseases in mammals are disclosed.

US Patent:

42063078, Jun 3, 1980

Filed:

Nov 7, 1978

Appl. No.:

5/958529

Inventors:

Carroll G. Temple - Birmingham AL
Robert D. Elliott - Birmingham AL
Jerry D. Rose - Birmingham AL
John A. Montgomery - Birmingham AL

Assignee:

United States of America - Washington DC

International Classification:

C07D47504

US Classification:

544258

Abstract:

Improved methods for the preparation and purification of citrovorum factor are disclosed. The method includes improved procedures for hydrogenation of 10-formylfolic acid as well as for the reduction of folic acid. Also disclosed are improved procedures for opening of the imidazoline ring, and a non-chromatographic method for the purification of crude samples of citrovorum factor.

US Patent:

45269645, Jul 2, 1985

Filed:

Aug 31, 1982

Appl. No.:

6/413501

Inventors:

Carroll G. Temple - Birmingham AL
John A. Montgomery - Birmingham AL
Robert D. Elliott - Birmingham AL

Assignee:

Southern Research Institute - Birmingham AL

International Classification:

C07D47104
A61K 31505

US Classification:

544279

Abstract:

There is disclosed a novel intermediate useful in the preparation of pyrido [2,3-d] pyrimidines, which includes N-[4-[(2-amino-4(3H)-oxopyrido[2,3-d]pyrimidin-6-yl)methylamino]benzoyl]-L -glutamic acid (5-deazafolic acid), N-[4-[[2-amino-4(3H)-oxopyrido[2,3-d]-pyrimidin-6-yl)methyl]methylamino]be nzoyl]-L-glutamic acid (5-deaza-N. sup. 10 -methylfolic acid), N-(4-[(2,4-diaminopyrido[2,3-d]pyrimidin-6-yl)methylamino]benzoyl]-L-gluta mic acid (5-deazaaminopterin), and N-[4-[[2,4-diaminopyrido[2,3-d]pyrimidin-6-yl)methyl]methylamino]benzoyl]- L-glutamic acid (5-deazamethotrexate). This intermediate is the compound 2,4-diamino-6-(hydroxymethyl)pyrido-[2,3-d]pyrimidine.