Arthur D Sill

US Patent:

39579883, May 18, 1976

Filed:

Feb 20, 1973

Appl. No.:

5/334075

Inventors:

Robert W. Fleming - Ann Arbor MI
Arthur D. Sill - Greenhills OH

Assignee:

Richardson-Merrell Inc. - Wilton CT

International Classification:

A01N 900

US Classification:

424248

Abstract:

The novel bis-basic ketones of thioxanthene have antiviral activity when administered orally and parenterally. These compounds are represented by the following formula: ##SPC1## Wherein A is a straight or branched alkylene chain having from 1 to about 6 carbon atoms; and each Y is A. the group ##EQU1## wherein R. sup. 1 and R. sup. 2 are individually hydrogen or lower alkyl having from 1 to about 4 carbon atoms; or B. the group ##EQU2## WHEREIN N IS A WHOLE INTEGER OF 4 OR 5, AND R. sup. 3 is hydrogen or lower alkyl having from 1 to about 4 carbon atoms and can be linked to any one of the carbon atoms of the heterocyclic group; or C. the group ##EQU3## wherein X is oxygen or NR. sup. 4, and R. sup. 4 is hydrogen or lower alkyl of from 1 to about 4 carbon atoms; or pharmaceutically acceptable acid addition salts of said base. These new compounds can be prepared by several different methods which are described.

US Patent:

40482308, Sep 13, 1977

Filed:

Dec 21, 1972

Appl. No.:

5/317248

Inventors:

Arthur D. Sill - Cincinnati OH
Francis W. Sweet - Cincinnati OH

Assignee:

Richardson-Merrell Inc. - Wilton CT

International Classification:

C07C 9710

US Classification:

2605705C

Abstract:

Novel 3,6-bis basic ketone derivatives of acenaphthene, their preparation and use for the prevention and inhibition of viral infections are disclosed.

US Patent:

39579891, May 18, 1976

Filed:

Feb 20, 1973

Appl. No.:

5/333768

Inventors:

Robert W. Fleming - Ann Arbor MI
Arthur D. Sill - Greenhills OH
Francis W. Sweet - Cincinnati OH

Assignee:

Richardson-Merrell Inc. - Wilton CT

International Classification:

A01N 900

US Classification:

424248

Abstract:

Novel bis-basic ketones of xanthene and xanthen-9-one have antiviral activity when administered orally and parenterally. The compounds are represented by the following formula: ##SPC1## Wherein Z is oxygen or H. sub. 2 ; each A is a straight or branched alkylene chain having from 1 to about 6 carbon atoms; and each Y is A. the group ##EQU1## wherein R. sup. 1 and R. sup. 2 are individually hydrogen, lower alkyl having from 1 to about 6 carbon atoms, cycloalkyl having from 3 to 6 carbon atoms, alkenyl of from 3 to 6 carbon atoms and having the vinyl unsaturation in other than the 1-position of the alkenyl group; or B. the group ##EQU2## WHEREIN N IS A WHOLE INTEGER FROM 4 TO 6, AND R. sup. 3 is hydrogen, lower alkyl of from 1 to about 4 carbon atoms and can be linked to any one of the carbon atoms of the heterocyclic group; or C. the group ##EQU3## wherein X is oxygen or NR. sup. 4, and R. sup.

US Patent:

39579867, May 18, 1976

Filed:

Jul 2, 1973

Appl. No.:

5/375754

Inventors:

Albert A. Carr - Cincinnati OH
Robert W. Fleming - Cincinnati OH
Arthur D. Sill - Cincinnati OH

Assignee:

Richardson-Merrell Inc. - Wilton CT

International Classification:

A01N 900

US Classification:

424248

Abstract:

Novel bis-basic esters and amides of xanthene and xanthone of the formula ##SPC1## Wherein: Z is oxygen or H. sub. 2 ; each of R. sup. 1 and R. sup. 2 is hydrogen, (lower)-alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 ring carbon atoms, alkenyl of 3 to 6 carbon atoms having the vinyl unsaturation in other than the 1-position of the alkenyl group, or each set of R. sup. 1 and R. sup. 2 taken together with the nitrogen atom to which they are attached is pyrrolidino, piperidino, N-(lower)alkylpiperazino, or morpholino; Each A is alkylene of 2 to about 8 carbon atoms and separates its adjacent Y and amino nitrogen by an alkylene chain of at least 2 carbon atoms; and each Y is oxygen, or >N--R wherein R is hydrogen or (lower)-alkyl of 1 to 4 carbon atoms; Or a pharmaceutically acceptable acid addition salt thereof. These compounds can be used as pharmaceuticals for preventing or inhibiting a viral infection.

US Patent:

39832481, Sep 28, 1976

Filed:

Aug 6, 1971

Appl. No.:

5/169861

Inventors:

Johann M. Grisar - Cincinnati OH
Arthur D. Sill - Cincinnati OH
Robert W. Fleming - Cincinnati OH

Assignee:

Richardson-Merrell Inc. - Wilton CT

International Classification:

H61K 3118

US Classification:

424321

Abstract:

Compounds useful as antiviral agents are those of the formula ##SPC1## Wherein each R. sup. 1 is hydrogen or methyl; each n is an integer of 2 to 4; each of R. sup. 2 and R. sup. 3 is alkyl of 3 to 5 carbon atoms or alkenyl of 3 to 5 carbon atoms; or a pharmaceutically acceptable acid addition salt of said base. Pharmaceutical compositions are formed from these compounds with pharmaceutically acceptable carriers.

US Patent:

40739040, Feb 14, 1978

Filed:

Jan 26, 1976

Appl. No.:

5/652345

Inventors:

Robert W. Fleming - Cincinnati OH
Arthur D. Sill - Cincinnati OH
Francis W. Sweet - Cincinnati OH

Assignee:

Richardson-Merrell, Inc. - Wilton CT

International Classification:

C07D40110
C07D40310
C07D41310
A61K 31445

US Classification:

42424858

Abstract:

Disclosed are novel compounds and pharmaceutical formulations having antiviral activity. The disclosed compounds have the formula ##STR1## wherein one R. sup. 2 is a hydrogen atom and the other R. sup. 2 is the radical ##STR2## A is a straight chain alkylene group having 2 or 3 carbon atoms and each R. sup. 3 and R. sup. 4 is a hydrogen atom, and alkyl radical having 1 to 3 carbon atoms or each set of R. sup. 3 and R. sup. 4 taken together with the nitrogen atom to which they are attached is a saturated monocyclic heterocyclic group. Also included are the acid addition salts of these bases. These compounds may be prepared by various methods which are described.

US Patent:

39534553, Apr 27, 1976

Filed:

Sep 13, 1974

Appl. No.:

5/505662

Inventors:

Donald R. Meyer - Cincinnati OH
Arthur D. Sill - Cincinnati OH

Assignee:

Richardson-Merrell Inc. - Wilton CT

International Classification:

C07D21532

US Classification:

260286A

Abstract:

Novel bis basic esters of 9-substituted phenanthrene and related 9-oxa and 9-aza derivatives thereof, their preparation and use for the prevention and inhibition of viral infections are disclosed.

US Patent:

40082407, Feb 15, 1977

Filed:

Dec 21, 1972

Appl. No.:

5/317148

Inventors:

Arthur D. Sill - Cincinnati OH
Francis W. Sweet - Cincinnati OH

Assignee:

Richardson-Merrell Inc. - Wilton CT

International Classification:

C07D40914

US Classification:

26029358

Abstract:

Novel 2,7-bis basic alkanol derivatives of xanthene and thioxanthene, their preparation and use for the prevention and inhibition of viral infections are disclosed.