US4596798A
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US
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2-acetylpyridine thiosemicarbazones as antiviral agents
Assignee: University of Michigan (System)
•
Filing: 1982-03-30
•
Granted: 1986-06-24
•
Expires: 2002-03-30
Abstract
Abstract This invention relates to the use of various 2-acetylpyridine thiosemicarbazones which are substituted on the 4-nitrogen atom in the treatment of viral infections. Also disclosed are several synthetic procedures used to prepare the thiosemicarbazones.
Inventors
- 👤 Charles Shipman, Jr.
- 👤 Daniel L. Klayman
- 👤 Sandra H. Smith
- 👤 John C. Drach
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 00:29
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/44; C07D213/53; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/435; A61K31/44
Claims Analysis
Total Claims: 66
Claim 1
Independent Claim
393 words
A method of topically treating the tissue of an animal which has been infected with a herpes virus comprising applying to the tissue of said animal a therapeutically-effective amount of: (a) a 2-acetylpyridine thiosemicarbazone selected from the compounds represented by the formula ##STR11## or, (b) a pharmaceutically-acceptable acid addition salt thereof wherein R 1 is hydrogen; alkyl having 1 to 12 carbon atoms; cycloalkyl having 3 to 10 carbon atoms; alkyl having 1 to 12 carbon atoms which is substituted by amino, alkylamino having 1 to 7 carbon atoms, dialkylamino having 1 7 carbon atoms in each alkyl group, cycloalkyl having 3 to 10 carbon atoms, hydroxy, C(O)Oalkyl having 1 to 7 carbon atoms in the alkyl group, phenyl, or pyridyl; alkenyl having 2 to 6 carbon atoms; alkynyl having 3 to 6 carbon atoms; benzyl which is substituted by methyl or phenyl on the alpha carbon atom, or substituted by methyl, dimethyl, halo, dihalo, or ethoxy on the phenyl ring; adamantyl; phenyl; naphthyl; phenyl or naphthyl which are mono-, di-, or trisubstituted by alkyl having 1 to 7 carbon atoms, halo, alkoxy having 1 to 7 carbon atoms, hydroxy, phenoxy, trifluoromethyl, dimethylamino, diethylaminomethyl, or C(O)Oalkyl having 1 to 7 carbon atoms in the alkyl group; pyridyl; thienyl; indolyl; furyl; acridyl; quinolyl; or pyridazinyl; and R 2 is hydrogen or is selected from the group of radicals listed above for R 1 , in which case R 1 and R 2 may be the same or different; or R 1 and R 2 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring selected from the group consisting of : (1) alkylenimino which is either bridged by an ethylene group, or is fused to a phenyl ring, or is attached by a spiro linkage to an ethylene ketal group; (2) homopiperazinyl; homopiperazinyl substituted with alkyl having 1 to 7 carbon atoms; piperazinyl; or piperazinyl substituted with alkyl having 1 to 7 carbon atoms, dialkyl having 1 to 7 carbon atoms in each alkyl group, phenyl, C(O)Oalkyl having 1 to 7 carbon atoms in the alkyl group, trifluoromethylphenyl, halophenyl, benzyl, or pyridyl; (3) alkylenimino which may contain one double bond and may be mono- or disubstituted with alkyl, hydroxy, phenyl, or benzyl; and (4) morpholino; or dialkylmorpholino having 1 to 7 carbon atoms in each alkyl group.
Claim 2
Independent Claim
393 words
A method of topically treating the tissue of an animal which has been infected with a herpes virus comprising applying to the tissue of said animal a therapeutically-effective amount of: (a) a 2-acetylpyridine thiosemicarbazone selected from the compounds represented by the formula ##STR11## or, (b) a pharmaceutically-acceptable acid addition salt thereof wherein R 1 is hydrogen; alkyl having 1 to 12 carbon atoms; cycloalkyl having 3 to 10 carbon atoms; alkyl having 1 to 12 carbon atoms which is substituted by amino, alkylamino having 1 to 7 carbon atoms, dialkylamino having 1 7 carbon atoms in each alkyl group, cycloalkyl having 3 to 10 carbon atoms, hydroxy, C(O)Oalkyl having 1 to 7 carbon atoms in the alkyl group, phenyl, or pyridyl; alkenyl having 2 to 6 carbon atoms; alkynyl having 3 to 6 carbon atoms; benzyl which is substituted by methyl or phenyl on the alpha carbon atom, or substituted by methyl, dimethyl, halo, dihalo, or ethoxy on the phenyl ring; adamantyl; phenyl; naphthyl; phenyl or naphthyl which are mono-, di-, or trisubstituted by alkyl having 1 to 7 carbon atoms, halo, alkoxy having 1 to 7 carbon atoms, hydroxy, phenoxy, trifluoromethyl, dimethylamino, diethylaminomethyl, or C(O)Oalkyl having 1 to 7 carbon atoms in the alkyl group; pyridyl; thienyl; indolyl; furyl; acridyl; quinolyl; or pyridazinyl; and R 2 is hydrogen or is selected from the group of radicals listed above for R 1 , in which case R 1 and R 2 may be the same or different; or R 1 and R 2 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring selected from the group consisting of : (1) alkylenimino which is either bridged by an ethylene group, or is fused to a phenyl ring, or is attached by a spiro linkage to an ethylene ketal group; (2) homopiperazinyl; homopiperazinyl substituted with alkyl having 1 to 7 carbon atoms; piperazinyl; or piperazinyl substituted with alkyl having 1 to 7 carbon atoms, dialkyl having 1 to 7 carbon atoms in each alkyl group, phenyl, C(O)Oalkyl having 1 to 7 carbon atoms in the alkyl group, trifluoromethylphenyl, halophenyl, benzyl, or pyridyl; (3) alkylenimino which may contain one double bond and may be mono- or disubstituted with alkyl, hydroxy, phenyl, or benzyl; and (4) morpholino; or dialkylmorpholino having 1 to 7 carbon atoms in each alkyl group.
Claim 3
Dependent Claim
25 words
The method of claim 1 wherein the virus is selected from the group consisting essentially of herpes simplex virus-1; herpes simplex virus-2; and varicella-zoster virus.
Claim 4
Dependent Claim
11 words
The method of claim 2 wherein the virus is varicella-zoster virus.
Claim 5
Dependent Claim
22 words
The method of claim 2 wherein the virus is selected from the group consisting of herpes simplex virus-1 and herpes simplex virus-2.
Claim 6
Dependent Claim
12 words
The method of claim 4 wherein the virus is herpes simplex virus-1.
Claim 7
Dependent Claim
12 words
The method of claim 4 wherein the virus is herpes simplex virus-2.
Claim 8
Dependent Claim
271 words
The method of claim 1 wherein R 1 is hydrogen, alkyl of 1 to 12 carbon atoms; cycloalkyl of 3 to 10 carbon atoms; alkyl of 1 to 12 carbon atoms which is substituted by amino, alkylamino of 1 to 4 carbon atoms, dialkylamino having 1 to 4 carbon atoms in each alkyl group; cycloalkyl of 3 to 10 carbon atoms, hydroxy, C(O)Oalkyl having 1 to 4 carbon atoms in each alkyl group, phenyl, or pyridyl; alkenyl having 2 to 6 carbon atoms; alkynyl having 3 to 6 carbon atoms; benzyl which is substituted by a methyl or phenyl on the alpha carbon atom, or substituted by methyl, dimethyl, halo, dihalo, or ethoxy on the phenyl ring; adamantyl; phenyl; naphthyl; phenyl or naphthyl which are mono-, di-, or trisubstituted by alkyl having 1 to 4 carbon atoms, halo, alkoxy having 1 to 4 carbon atoms, hydroxy, phenoxy, trifluoromethyl, dimethylamino, diethylaminomethyl, or C(O)Oalkyl having 1 to 4 carbon atoms in the alkyl group; pyridyl; thienyl; indolyl; furyl; acridyl; quinolyl; or pyridazinyl; and R 2 is hydrogen or is selected from the group of radicals listed above for R 1 , in which case R 1 and R 2 may be the same or different; or R 1 and R 2 are taken together with the nitrogen atom to which they are attached to form a heterocyclic ring selected from the group consisting of: azetidino; pyrrolidino; 2,5-dimethylpyrrolidino; piperidino; ##STR12## (wherein X is 2-methyl, 3-methyl, 4-methyl, 2-ethyl, 4-hydroxy, 4-phenyl, or 4-benzyl); hexamethylenimino; octamethylenimino; dodecamethylenimino; 2,6-dimethyl piperidino; 3,5-dimethylpiperidino; morpholino; 3,5-dimethylmorpholino; ##STR13## and azacyclotridecyl, wherein Z is methyl, phenyl, 3-trifluoromethylphenyl, benzyl, C(O)OEt, 3-pyridyl, 2-pyridyl, or 4-fluorophenyl.
Claim 9
Dependent Claim
117 words
The method of claim 7 wherein the 2-acetylpyridine thiosemicarbazone is selected from the compounds selected from the group consisting of 1-H-hexahydroazepin-1-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide, 1-Azacycloheptane-1-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide; 2-Acetylpyridine 4-(3-fluorophenyl)-3-thiosemicarbazone; 3-Azabicyclo[3.2.2]nonane-3-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide; 1-Methylamino-1-deoxy-D-glucitol-N-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide; 2-Acetylpyridine 4,4-dimethylthiosemicarbazone; 2-Acetylpyridine 4-(1-adamantyl)thiosemicarbazone; 2-Acetylpyridine 4-cyclohexyl-4-methylthiosemicarbazone; 2-Acetylpyridine 4-methylthiosemicarbazone; 2-Acetylpyridine thiosemicarbazone; Azetidine-1-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide; 1-Azacyclopentane-1-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide; Piperidine-1-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide; 2-Methylpiperidine-1-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide; 2-Ethylpiperidine-1-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide; 1-Azacyclotridecane-1-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide; 2-Acetylpyridine 4-allyl-3-thiosemicarbazone; 2-Acetylpyridine 4-(2-picolyl)-3-thiosemicarbazone; 2-Acetylpyridine 4-cyclohexyl-3-thiosemicarbazone; 2-Acetylpyridine 4-phenyl-3-thiosemicarbazone; 2-Acetylpyridine 4-(1,1,3,3-tetramethylbutyl)-3-thiosemicarbazone; 1,4-Diaza-4-carboethoxycyclohexane-1-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide; 1,4-Diaza-4-phenylcyclohexane-1-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide; 2-Acetylpyridine 4-(2-methylbenzyl)-3-thiosemicarbazone; 2-Acetylpyridine 4-(4-trifluoromethyl-phenyl)-3-thiosemicarbazone; 1,4-Diaza-4-(2-pyridyl)cyclohexane-1-thiocarboxylic acid 2[1-(2-pyridyl)ethylidene]hydrazide; 1,4-Diaza-4-(2-pyridyl)cyclohexane-1-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide dihydrochloride; 2-Acetylpyridine 4-benzyl-3-thiosemicarbazone; 1,4-Diaza-4-methylcycloheptane-1-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide; 2-Acetylpyridine 4-(2-propynyl)-3-thiosemicarbazone; 2-Acetylpyridine 4,4-dibutylthiosemicarbazone; 2-Acetylpyridine 4-ethylthiosemicarbazone; 2-Acetylpyridine 4-butylthiosemicarbazone; 2-Acetylpyridine 4-octylthiosemicarbazone; 2-Acetylpyridine 4-decylthiosemicarbazone; 2-Acetylpyridine 4-(2-phenethyl)thiosemicarbazone; (4-Hydroxy-4-phenylpiperidine)-1-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide; 2-Acetylpyridine 4-(3-pinylmethyl)thiosemicarbazone; and 1-Azacyclononane-1-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide.
Claim 10
Dependent Claim
38 words
The method of claim 8 wherein the 2-acetylpyridine thiosemicarbazone is selected from the group consisting of: 1H-Hexahydroazepin-1-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide; 2-Acetylpyridine 4-(3-fluorophenyl)thiosemicarbazone; 3-Azabicyclo[3.2.2]nonane-3-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide; 1-Methylamino-1-deoxy-D-glucitol-N-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide; 2-Acetylpyridine 4,4-dimethylthiosemicarbazone; 2-Acetylpyridine 4-(1-adamantyl)thiosemicarbazone; 2-Acetylpyridine 4-cyclohexyl-4-methylthiosemicarbazone; 2-Acetylpyridine 4-methylthiosemicarbazone; and 2-Acetylpyridine thiosemicarbazone.
Claim 11
Dependent Claim
12 words
The method of claim 8, wherein the thiosemicarbazone is 1H-hexadhydroazepin-1-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide.
Claim 12
Dependent Claim
12 words
The method of claim 8 wherein the 2-acetylpyridine thiosemicarbazone is 2-acetylpyridine 4-(3-fluorophenyl)thiosemicarbazone.
Claim 13
Dependent Claim
12 words
The method of claim 8 wherein the thiosemicarbazone is 3-azabicyclo[3.2.2]nonane-3-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide.
Claim 14
Dependent Claim
12 words
The method of claim 8 wherein the thiosemicarbazone is 1-methylamino-1-deoxy-D-glucitol-N-thiocarboxylic acid 2-[1-(2-pyridyl)ethylidene]hydrazide.
Claim 15
Dependent Claim
12 words
The method of claim 8 wherein the 2-acetylpyridine thiosemicarbazone is 2-acetylpyridine 4,4-dimethylthiosemicarbazone.
Claim 16
Dependent Claim
12 words
The method of claim 8 wherein the 2-acetylpyridine thiosemicarbazone is 2-acetylpyridine 4-(1-adamantyl)thiosemicarbazone.
Claim 17
Dependent Claim
12 words
The method of claim 8 wherein the 2-acetylpyridine thiosemicarbazone is 2-acetylpyridine 4-cyclohexyl-4-methylthiosemicarbazone.
Claim 18
Dependent Claim
12 words
The method of claim 8 wherein the 2-acetylpyridine thiosemicarbazone is 2-acetylpyridine 4-methylthiosemicarbazone.
Claim 19
Dependent Claim
12 words
The method of claim 8 wherein the 2-acetylpyridine thiosemicarbazone is 2-acetylpyridine thiosemicarbazone.
Claim 20
Dependent Claim
19 words
The method of claim 1 wherein R 1 is hydrogen and R 2 is --CH 2 CH═CH 2 .
Claim 21
Dependent Claim
15 words
The method of claim 1 wherein R 1 is hydrogen and R 2 is ##STR14##
Claim 22
Dependent Claim
15 words
The method of claim 1 wherein R 1 is hydrogen and R 2 is cyclohexyl.
Claim 23
Dependent Claim
15 words
The method of claim 1 wherein R 1 is hydrogen and R 2 is isooctyl.
Claim 24
Dependent Claim
15 words
The method of claim 1 wherein R 1 is hydrogen and R 2 is 3-fluorophenyl.
Claim 25
Dependent Claim
15 words
The method of claim 1 wherein R 1 is hydrogen and R 2 is ##STR15##
Claim 26
Dependent Claim
15 words
The method of claim 1 wherein R 1 is hydrogen and R 2 is 4-trifluoromethylphenyl.
Claim 27
Dependent Claim
15 words
The method of claim 1 wherein R 1 is hydrogen and R 2 is benzyl.
Claim 28
Dependent Claim
17 words
The method of claim 1 wherein R 1 is hydrogen and R 2 is --CH 2 C.tbd.CH.
Claim 29
Dependent Claim
15 words
The method of claim 1 wherein R 1 is ethyl and R 2 is ethyl.
Claim 30
Dependent Claim
15 words
The method of claim 1 wherein R 1 is hydrogen and R 2 is ethyl.
Claim 31
Dependent Claim
15 words
The method of claim 1 wherein R 1 is hydrogen and R 2 is butyl.
Claim 32
Dependent Claim
15 words
The method of claim 1 wherein R 1 is hydrogen and R 2 is hexyl.
Claim 33
Dependent Claim
15 words
The method of claim 1 wherein R 1 is hydrogen and R 2 is n-octyl.
Claim 34
Dependent Claim
15 words
The method of claim 1 wherein R 1 is hydrogen and R 2 is decyl.
Claim 35
Dependent Claim
15 words
The method of claim 1 wherein R 1 is hydrogen and R 2 is ##STR16##
Claim 36
Dependent Claim
15 words
The method of claim 1 wherein R 1 is hydrogen and R 2 is phenyl.
Claim 37
Dependent Claim
12 words
The method of claim 1 wherein NR 1 R 2 is ##STR17##
Claim 38
Dependent Claim
12 words
The method of claim 1 wherein NR 1 R 2 is ##STR18##
Claim 39
Dependent Claim
12 words
The method of claim 1 wherein NR 1 R 2 is ##STR19##
Claim 40
Dependent Claim
12 words
The method of claim 1 wherein NR 1 R 2 is ##STR20##
Claim 41
Dependent Claim
12 words
The method of claim 1 wherein NR 1 R 2 is ##STR21##
Claim 42
Dependent Claim
12 words
The method of claim 1 wherein NR 1 R 2 is ##STR22##
Claim 43
Dependent Claim
12 words
The method of claim 1 wherein NR 1 R 2 is ##STR23##
Claim 44
Dependent Claim
12 words
The method of claim 1 wherein NR 1 R 2 is ##STR24##
Claim 45
Dependent Claim
12 words
The method of claim 1 wherein NR 1 R 2 is ##STR25##
Claim 46
Dependent Claim
12 words
The method of claim 1 wherein NR 1 R 2 is ##STR26##
Claim 47
Dependent Claim
12 words
The method of claim 1 wherein NR 1 R 2 is ##STR27##
Claim 48
Dependent Claim
12 words
The method of claim 1 wherein NR 1 R 2 is ##STR28##
Claim 49
Dependent Claim
12 words
The method of claim 1 wherein NR 1 R 2 is ##STR29##
Claim 50
Dependent Claim
12 words
The method of claim 1 wherein NR 1 R 2 is ##STR30##
Claim 51
Independent Claim
272 words
A method of topically treating the skin of an animal which has been infected with a herpes virus selected from the group consisting of herpes simplex virus-1 and herpes simplex virus-2 comprising applying to the skin of said animal a therapeutically-effective amount of: (a) a 2-acetylpyridine thiosemicarbazone selected from the compounds represented by the formula ##STR31## (b) a pharmaceutically-acceptable acid addition salt thereof wherein R 1 is hydrogen; alkyl having 1 to 12 carbon atoms; cycloalkyl having 3 to 10 carbon atoms; alkyl having 1 to 12 carbon atoms which is substituted by amino, alkylamino having 1 to 7 carbon atoms, dialkylamino having 1 to 7 carbon atoms in each alkyl group, cycloalkyl having 3 to 10 carbon atoms, hydroxy, C(O)Oalkyl having 1 to 7 carbon atoms in the alkyl group, phenyl, or pyridyl; alkenyl having 2 to 6 carbon atoms; benzyl which is substituted by methyl or phenyl on the alpha carbon atom, or substituted by alkyl having 1 to 7 carbon atoms, dialkyl having 1 to 7 carbon atoms in each alkyl group, halo, dihalo, or alkoxy on the phenyl ring; adamantyl; phenyl; naphthyl; phenyl or naphthyl which are mono-, di, or trisubstituted by alkyl having 1 to 7 carbon atoms, halo, alkoxy having 1 to 7 carbon atoms, hydroxy, phenoxy, trifluoromethyl, dialkylamino having 1 to 7 carbon atoms in each alkyl group, or C(O)Oalkyl having 1 to 7 carbon atoms in the alkyl group; and pyridyl; and R 2 is hydrogen or is selected from the group of radicals listed above for R 1 , in which case R 1 and R 2 may be the same or different.
Claim 52
Independent Claim
272 words
A method of topically treating the skin of an animal which has been infected with a herpes virus selected from the group consisting of herpes simplex virus-1 and herpes simplex virus-2 comprising applying to the skin of said animal a therapeutically-effective amount of: (a) a 2-acetylpyridine thiosemicarbazone selected from the compounds represented by the formula ##STR31## (b) a pharmaceutically-acceptable acid addition salt thereof wherein R 1 is hydrogen; alkyl having 1 to 12 carbon atoms; cycloalkyl having 3 to 10 carbon atoms; alkyl having 1 to 12 carbon atoms which is substituted by amino, alkylamino having 1 to 7 carbon atoms, dialkylamino having 1 to 7 carbon atoms in each alkyl group, cycloalkyl having 3 to 10 carbon atoms, hydroxy, C(O)Oalkyl having 1 to 7 carbon atoms in the alkyl group, phenyl, or pyridyl; alkenyl having 2 to 6 carbon atoms; benzyl which is substituted by methyl or phenyl on the alpha carbon atom, or substituted by alkyl having 1 to 7 carbon atoms, dialkyl having 1 to 7 carbon atoms in each alkyl group, halo, dihalo, or alkoxy on the phenyl ring; adamantyl; phenyl; naphthyl; phenyl or naphthyl which are mono-, di, or trisubstituted by alkyl having 1 to 7 carbon atoms, halo, alkoxy having 1 to 7 carbon atoms, hydroxy, phenoxy, trifluoromethyl, dialkylamino having 1 to 7 carbon atoms in each alkyl group, or C(O)Oalkyl having 1 to 7 carbon atoms in the alkyl group; and pyridyl; and R 2 is hydrogen or is selected from the group of radicals listed above for R 1 , in which case R 1 and R 2 may be the same or different.
Claim 53
Dependent Claim
12 words
The method of claim 50 wherein the virus is herpes simplex virus-1.
Claim 54
Dependent Claim
12 words
The method of claim 50 wherein the virus is herpes simplex virus-2.
Claim 55
Dependent Claim
29 words
The method of claim 50 wherein NR 1 R 2 is selected from the group consisting of --NH 2 , --NHCH 3 , --NH--CH 2 CH═CH 2 , ##STR32##
Claim 56
Dependent Claim
18 words
The method of claim 53 wherein NR 1 R 2 is selected from the group consisting of ##STR33##
Claim 57
Dependent Claim
19 words
The method of claim 54 wherein the virus is herpes simplex virus-2 and NR 1 R 2 is ##STR34##
Claim 58
Dependent Claim
19 words
The method of claim 54 wherein the virus is herpes simplex virus-1 and NR 1 R 2 is ##STR35##
Claim 59
Dependent Claim
21 words
The method of claim 54 wherein the virus is herpes simplex virus-1 and NR 1 R 2 is --NH 2 .
Claim 60
Dependent Claim
21 words
The method of claim 54 wherein the virus is herpes simplex virus-2 and NR 1 R 2 is --NH 2 .
Claim 61
Dependent Claim
21 words
The method of claim 54 wherein the virus is herpes simplex virus-1 and NR 1 R 2 is --NHCH 3 .
Claim 62
Dependent Claim
21 words
The method of claim 54 wherein the virus is herpes simplex virus-2 and NR 1 R 2 is --NHCH 3 .
Claim 63
Dependent Claim
23 words
The method of claim 54 wherein the virus is herpes simplex virus-1 and --NR 1 R 2 is --NHCH 2 --CH═CH 2 .
Claim 64
Dependent Claim
23 words
The method of claim 54 wherein the virus is herpes simplex virus-2 and --NR 1 R 2 is --NHCH 2 --CH═CH 2 .
Claim 65
Dependent Claim
19 words
The method of claim 54 wherein the virus is herpes simplex virus-1 and --NR 1 R 2 is ##STR36##
Claim 66
Dependent Claim
19 words
The method of claim 54 wherein the virus is herpes simplex virus-2 and --NR 1 R 2 is ##STR37##
References Cited (Backward Citations)
US4317776A
Cited
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