William A Michne

US Patent:

39324222, Jan 13, 1976

Filed:

May 20, 1974

Appl. No.:

5/471571

Inventors:

William F. Michne - Colonie NY

Assignee:

Sterling Drug Inc. - New York NY

International Classification:

C07D22122

US Classification:

26029354

Abstract:

6(EQ)-R. sub. 4 -1,2,3,4,5,6-Hexahydro-3-R. sub. 1 -11(ax)-R. sub. 3 -11(eq)-CH. sub. 2 Z-2,6-methano-3-benzazocines, useful as analgesic agents and narcotic antagonists, and 1-R. sub. 1 -2-Q-4a. alpha. -R. sub. 3 -5. alpha. -R. sub. 4 -1,2,3,4,4a,5,10,10a-octahydro-3,5-etheno- (and 3,5-ethano) benzo[g]quinolines, useful as analgesic agents, prepared by heating, with formic acid in an organic solvent or with certain ammonium formates in the absence of a solvent, certain 1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinolines, the latter prepared by acid catalyzed cyclization of a 3-benzyl-2-azabicyclo[2. 2. 2]oct-5-ene.

US Patent:

41806670, Dec 25, 1979

Filed:

Feb 13, 1978

Appl. No.:

5/877166

Inventors:

William F. Michne - Poestenkill NY

Assignee:

Sterling Drug Inc. - New York NY

International Classification:

C07D22122

US Classification:

546112

Abstract:

6(eq)-R. sub. 4 -1,2,3,4,5,6-Hexahydro-3-R. sub. 1 -11(ax)-R. sub. 3 -11(eq)-CH. sub. 2 Z-2,6-methano-3-benzazocines, useful as analgesic agents and narcotic antagonists, and 1-R. sub. 1 -2-Q-4a. alpha. -R. sub. 3 -5. alpha. -R. sub. 4 -1,2,3,4,4a,5,10,10a-octahydro-3,5-etheno- (and 3,5-ethano) benzo[g]quinolines, useful as analgesic agents, prepared by heating, with formic acid in an organic solvent or with certain ammonium formates in the absence of a solvent, certain 1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinolines, the latter prepared by acid catalyzed cyclization of a 3-benzyl-2-azabicyclo[2. 2. 2]-oct-5-ene.

US Patent:

42085233, Jun 17, 1980

Filed:

Nov 30, 1978

Appl. No.:

5/964915

Inventors:

William F. Michne - Poestenkill NY
Thomas R. Lewis - Bethlehem NY

Assignee:

Sterling Drug Inc. - New York NY

International Classification:

C07D22126

US Classification:

546 97

Abstract:

3-R. sub. 1 -7-R. sub. 2 "-8-R. sub. 2 -9-R. sub. 2 '-10-R. sub. 2 "'-11(ax)-R. sub. 3 -6(eq)-R. sub. 4 -11(eq)-(CH. sub. 2 CH. sub. 2 CH. sub. 2 R. sub. 5)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines, generally useful as morphine-like analgesics and as narcotic antagonists, are prepared by reducing, under Wolff-Kishner reaction conditions, a corresponding 3-R. sub. 1 -7-R. sub. 2 "-8-R. sub. 2 -9-R. sub. 2 '-10-R. sub. 2 "'-11(ax)-R. sub. 3 -6(eq)-R. sub. 4 -11(eq)-(CH. sub. 2 CH. sub. 2 COR. sub. 5)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocine and, if desired, cleaving a lower-alkoxy, methoxymethoxy or benzyloxy group to an hydroxy group.

US Patent:

42140854, Jul 22, 1980

Filed:

May 4, 1979

Appl. No.:

6/036060

Inventors:

Thomas R. Lewis - Bethlehem NY
William F. Michne - Poestenkill NY

Assignee:

Sterling Drug Inc. - New York NY

International Classification:

C07D40506

US Classification:

546 97

Abstract:

3-R. sub. 1 -6(eq)-R. sub. 4 -7-R. sub. 2 "-8-R. sub. 2 -9-R. sub. 2 '-10-R. sub. 2 '''-11(ax)-R. sub. 3 -11(eq)-[CH. sub. 2 CH. sub. 2 CO(CH. sub. 2). sub. n -(2- and 3-furyl)]-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines, useful as analgesics and narcotic antagonists, are prepared either by heating, with formic acid in an organic solvent or with certain ammonium formates, certain lower-alkyl 1-R. sub. 1 -4a. alpha. -R. sub. 3 -5. alpha. -R. sub. 4 -6-R. sub. 2 "-7-R. sub. 2 -8-R. sub. 2 '-9-R. sub. 2 '''-3-[CO(CH. sub. 2). sub. n -(2- and 3-furyl]-1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinoline-3-carb oxylates or by reaction of a lower-alkyl. beta. -[3-R. sub. 1 -6(eq)-R. sub. 4 -7-R. sub. 2 "-8-R. sub. 2 -9-R. sub. 2 '-10-R. sub. 2 '''-11(ax)-R. sub. 3 -1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-11(eq)-yl]propionate with 2- or 3-furylacetic acid in the presence of a strong base.

US Patent:

39766535, Aug 24, 1976

Filed:

Dec 16, 1974

Appl. No.:

5/532872

Inventors:

Noel F. Albertson - Schodack NY
William F. Michne - Colonie NY

Assignee:

Sterling Drug Inc. - New York NY

International Classification:

C07D21120

US Classification:

26029383

Abstract:

1,2,3,4,4a,5,10,10a-octahydro-5-(Y. sup. 3)-5-(Y. sup. 4)-benzo[g]quinolines and 1,2,3,4,4a,9b-hexahydro-5-(Y. sup. 3)-5-(Y. sup. 4)-5H-indeno[1,2,b]pyridi nes wherein Y. sup. 3 and Y. sup. 4 are hydrogen, alkyl or phenyl, which are useful as antagonists of strong analgesics, are obtained by cyclizing derivatives of 2-(phenyl or benzyl)-. alpha. -(Y. sup. 3)-. alpha. -(Y. sup. 4)-3-piperidinemethanols. The latter are obtained from corresponding 3-piperidinecarboxylic acids.

US Patent:

40227928, May 10, 1977

Filed:

May 27, 1976

Appl. No.:

5/690413

Inventors:

Noel F. Albertson - Schodack NY
William F. Michne - Clifton Park NY

Assignee:

Sterling Drug Inc. - New York NY

International Classification:

C07D21170

US Classification:

26029383

Abstract:

1,2,3,4,4a,5,10,10a-Octahydro-5-(Y. sup. 3)-5-(Y. sup. 4)-benzo[g]quinolines and 1,2,3,4,4a,9b-hexahydro-5-(Y. sup. 3)-5-(Y. sup. 4)-5H-indeno[1,2,b]pyridi nes wherein Y. sup. 3 and Y. sup. 4 are hydrogen, alkyl or phenyl, which are useful as antagonists of strong analgesics, are obtained by cyclizing derivatives of 2-(phenyl or benzyl)-. alpha. -(Y. sup. 3)-. alpha. -(Y. sup. 4)-3-piperidinemethanols. The latter are obtained from corresponding 3-piperidinecarboxylic acids.

US Patent:

52391108, Aug 24, 1993

Filed:

Dec 30, 1992

Appl. No.:

7/998233

Inventors:

John P. Mallamo - Kinderhook NY
William F. Michne - Poestenkill NY
Aram Mooradian - Schodack NY

Assignee:

Sterling Winthrop, Inc. - Rensselaer NY

International Classification:

C07C 9100
C07C 8700

US Classification:

560250

Abstract:

Compounds of the formula ##STR1## wherein R. sub. 1 is lower-alkanoyl or hydrogen; R. sub. 2 and R. sub. 3 are the same or different lower-alkyl; or pharmaceutically acceptable acid-addition salts thereof are useful in the treatment of disorders of the central nervous system.

US Patent:

42398908, Dec 16, 1980

Filed:

Feb 5, 1979

Appl. No.:

6/009483

Inventors:

William F. Michne - Poestenkill NY

Assignee:

Sterling Drug Inc. - New York NY

International Classification:

C07D21514

US Classification:

546 74

Abstract:

1-R. sub. 1 -2-Q-4a. alpha. -R. sub. 3 -5. alpha. -R. sub. 4 -1,2,3,4,4a,5,10,10a-Octahydro-3,5-etheno- (and 3,5-ethano) benzo[g]quinolines, useful as analgesic agents, prepared by heating, with formic acid in an organic solvent or with certain ammonium formates in the absence of a solvent, certain 1,2,3,4,4a,5,10,10a-octahydro-2,5-methanobenzo[g]quinolines, the latter prepared by acid catalyzed cyclization of a 3-benzyl-2-azabicyclo[2. 2. 2]oct-5-ene.