US4221794A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Method of imparting immunomodulating and antiviral activity
Assignee: Newport Pharmaceuticals International Inc
•
Filing: 1979-06-21
•
Granted: 1980-09-09
•
Expires: 1999-06-21
Abstract
Abstract Compounds of the formula <IMAGE> where X is OH, NH2, SH, OR or SR (where R is alkyl of 1 to 4 carbon atoms or benzyl), R1 is H or alkyl of 1 to 8 carbon atoms, R2 is H or methyl, Y is the salt of an amine of the formula <IMAGE> where R3 and R4 are lower alkyl, e.g., 1 to 4 carbon atoms and n is an integer of 2 to 4 with p-acetamidobenzoic acid and where z is a number from 0 to 10 are useful as immunomodulators, as antiviral agents and in specific cases have anti-leukemic activity. The compounds and compositions where z is 1 to 10 are novel per se. When R2 is H the presence of Y enhances the immunoregulatory activity and the antiviral activity. If X is the NH2 there is immunoinhibitory activity but no immunostimulatory (immunopotentiatory) activity.
Inventors
- 👤 Lionel N. Simon
- 👤 John W. Hadden
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 19:33
CPC Classifications
C; C07; C07D; C07D473/00; C07D473/26; C07D473/28; C07D473/30; C07D473/32; C07D473/34; C07D473/36; C07D473/38
Claims Analysis
Total Claims: 94
Claim 1
Independent Claim
115 words
A method of imparting immunomodulating activity, antiviral activity or anti-leukemic activity comprising administering to a mammal an effective amount for such purpose of a compound of the formula ##STR36## where X is OH, NH 2 , SH, OR or SR (where R is alkyl of 1 to 4 carbon atoms or benzyl), R 1 is H or alkyl of 1 to 8 carbon atoms, R 2 is H or methyl, Y is the salt of an amine of the formula ##STR37## where R 3 and R 4 are lower alkyl, n is an integer from 2 to 4 and where z is 0 or a number from 1 to 10 with a pharmaceutically acceptable acid.
Claim 2
Independent Claim
115 words
A method of imparting immunomodulating activity, antiviral activity or anti-leukemic activity comprising administering to a mammal an effective amount for such purpose of a compound of the formula ##STR36## where X is OH, NH 2 , SH, OR or SR (where R is alkyl of 1 to 4 carbon atoms or benzyl), R 1 is H or alkyl of 1 to 8 carbon atoms, R 2 is H or methyl, Y is the salt of an amine of the formula ##STR37## where R 3 and R 4 are lower alkyl, n is an integer from 2 to 4 and where z is 0 or a number from 1 to 10 with a pharmaceutically acceptable acid.
Claim 3
Dependent Claim
18 words
A method according to claim 1 wherein when z is 1 to 10 the acid is p-acetamidobenzoic acid.
Claim 4
Dependent Claim
12 words
A method according to claim 2 wherein z is 1 to 10.
Claim 5
Dependent Claim
33 words
A method according to claim 3 where R 1 is H or n-alkyl of 1 to 8 carbon atoms and R 3 and R 4 are alkyl of 1 to 4 carbon atoms.
Claim 6
Dependent Claim
19 words
A method according to claim 4 where R 1 is H or n-alkyl of 1 to 7 carbon atoms.
Claim 7
Dependent Claim
19 words
A method according to claim 5 where R 1 is H or n-alkyl of 1 to 6 carbon atoms.
Claim 8
Dependent Claim
11 words
A method according to claim 6 where R 1 is n-hexyl.
Claim 9
Dependent Claim
14 words
A method according to claim 3 where X is OH, NH 2 or SH.
Claim 10
Dependent Claim
10 words
A method according to claim 8 where X is OH.
Claim 11
Dependent Claim
12 words
A method according to claim 8 where X is NH 2 .
Claim 12
Dependent Claim
10 words
A method according to claim 8 where X is SH.
Claim 13
Dependent Claim
11 words
A method according to claim 3 where R 2 is H.
Claim 14
Dependent Claim
10 words
A method according to claim 12 where X is OH.
Claim 15
Dependent Claim
12 words
A method according to claim 12 were X is NH 2 .
Claim 16
Dependent Claim
10 words
A method according to claim 12 where X is SH.
Claim 17
Dependent Claim
11 words
A method according to claim 3 where R 2 is methyl.
Claim 18
Dependent Claim
10 words
A method according to claim 16 where X is OH.
Claim 19
Dependent Claim
12 words
A method according to claim 16 where X is NH 2 .
Claim 20
Dependent Claim
10 words
A method according to claim 16 where X is SH.
Claim 21
Dependent Claim
24 words
A method according to claim 4 where X is OH, NH 2 or SH and Y is the salt of dimethylaminoisopropanol and p-acetamidobenzoic acid.
Claim 22
Dependent Claim
10 words
A method according to claim 20 where X is OH.
Claim 23
Dependent Claim
11 words
A method according to claim 20 where R 2 is hydrogen.
Claim 24
Dependent Claim
11 words
A method according to claim 20 where R 1 is n-hexyl.
Claim 25
Dependent Claim
11 words
A method according to claim 20 where R 1 is methyl.
Claim 26
Dependent Claim
11 words
A method according to claim 20 where R 2 is methyl.
Claim 27
Dependent Claim
11 words
A method according to claim 25 where R 1 is n-hexyl.
Claim 28
Dependent Claim
11 words
A method according to claim 26 where R 1 is methyl.
Claim 29
Dependent Claim
19 words
A method according to claim 3 where X is OH, NH 2 or SH and R 1 is hydrogen.
Claim 30
Dependent Claim
19 words
A method according to claim 3 wherein X is OH, R 1 is n-hexyl and R 2 is methyl.
Claim 31
Dependent Claim
10 words
A method according to claim 29 wherein z is 3.
Claim 32
Dependent Claim
16 words
A method according to claim 30 where Y is the salt of dimethylaminoisopropanol with p-acetamidobenzoic acid.
Claim 33
Dependent Claim
16 words
A method according to claim 29 where Y is the salt of dimethylaminoisopropanol with p-acetamidobenzoic acid.
Claim 34
Dependent Claim
11 words
A method according to claim 3 where R 2 is H.
Claim 35
Dependent Claim
23 words
A method according to claim 3 where X is NH 2 and the compound is used in an amount to impart immunoinhibiting activity.
Claim 36
Dependent Claim
11 words
A method according to claim 3 where R 2 is methyl.
Claim 37
Dependent Claim
18 words
A method according to claim 3 wherein the compound is used in an amount to impart immuno-modulating activity.
Claim 38
Dependent Claim
18 words
A method according to claim 36 wherein the compound is used in an amount to impart immuno-stimulating activity.
Claim 39
Dependent Claim
10 words
A method according to claim 37 where X is OH.
Claim 40
Dependent Claim
18 words
A method according to claim 3 wherein the compound is used in an amount to impart antiviral activity.
Claim 41
Dependent Claim
10 words
A method according to claim 39 where X is OH.
Claim 42
Dependent Claim
36 words
A method according to claim 3 wherein the compound is used in an amount to impart antileukemic activity, X is OH, R 1 is alkyl of 1 to 8 carbon atoms and R 2 is methyl.
Claim 43
Dependent Claim
11 words
A method according to claim 41 where R 1 is n-hexyl.
Claim 44
Dependent Claim
16 words
A method according to claim 42 where Y is the salt of dimethylaminoisopropanol with p-acetamidobenzoic acid.
Claim 45
Dependent Claim
16 words
A method according to claim 43 wherein the compound is administered to a mammal having leukemia.
Claim 46
Dependent Claim
18 words
A method according to claim 36 wherein the compound is used in an amount to impart immunoinhibiting activity.
Claim 47
Dependent Claim
10 words
A method according to claim 45 wherein X is OH.
Claim 48
Dependent Claim
11 words
A method according to claim 46 where R 1 is n-hexyl.
Claim 49
Dependent Claim
11 words
A method according to claim 47 where R 2 is methyl.
Claim 50
Dependent Claim
10 words
A method according to claim 1 where z is 0.
Claim 51
Dependent Claim
33 words
A method according to claim 49 where R 1 is H or n-alkyl of 1 to 8 carbon atoms and R 3 and R 4 are alkyl of 1 to 4 carbon atoms.
Claim 52
Dependent Claim
19 words
A method according to claim 50 where R 1 is H or n-alkyl of 1 to 7 carbon atoms.
Claim 53
Dependent Claim
19 words
A method according to claim 51 where R 1 is H or n-alkyl of 1 to 6 carbon atoms.
Claim 54
Dependent Claim
11 words
A method according to claim 52 where R 1 is n-hexyl.
Claim 55
Dependent Claim
14 words
A method according to claim 49 where X is OH, NH 2 or SH.
Claim 56
Dependent Claim
10 words
A method according to claim 54 where X is OH.
Claim 57
Dependent Claim
12 words
A method according to claim 54 where X is NH 2 .
Claim 58
Dependent Claim
10 words
A method according to claim 54 where X is SH.
Claim 59
Dependent Claim
11 words
A method according to claim 54 where R 2 is H.
Claim 60
Dependent Claim
10 words
A method according to claim 58 where X is OH.
Claim 61
Dependent Claim
12 words
A method according to claim 58 where X is NH 2 .
Claim 62
Dependent Claim
10 words
A method according to claim 58 where X is SH.
Claim 63
Dependent Claim
11 words
A method according to claim 54 where R 2 is methyl.
Claim 64
Dependent Claim
10 words
A method according to claim 62 where X is OH.
Claim 65
Dependent Claim
12 words
A method according to claim 62 where X is NH 2 .
Claim 66
Dependent Claim
10 words
A method according to claim 62 where X is SH.
Claim 67
Dependent Claim
19 words
A method according to claim 49 where X is OH, NH 2 or SH and R 1 is hydrogen.
Claim 68
Dependent Claim
10 words
A method according to claim 66 where X is OH.
Claim 69
Dependent Claim
19 words
A method according to claim 49 where X is OH, R 1 is n-hexyl and R 2 is methyl.
Claim 70
Dependent Claim
18 words
A method according to claim 49 wherein the compound is used in an amount to impart immunomodulating activity.
Claim 71
Dependent Claim
23 words
A method according to claim 69 wherein X is NH 2 and the compound is used in an amount to impart immunoinhibitory activity.
Claim 72
Dependent Claim
18 words
A method according to claim 69 wherein the compound is used in an amount to impart immunostimulating activity.
Claim 73
Dependent Claim
10 words
A method according to claim 71 where X is OH.
Claim 74
Dependent Claim
11 words
A method according to claim 72 where R 2 is methyl.
Claim 75
Dependent Claim
16 words
A method according to claim 73 where R 1 is 1 to 6 carbon atoms n-alkyl.
Claim 76
Dependent Claim
11 words
A method according to claim 74 where R 1 is n-hexyl.
Claim 77
Dependent Claim
18 words
A method according to claim 69 wherein the compound is used in an amount to impart immunoinhibiting activity.
Claim 78
Dependent Claim
10 words
A method according to claim 76 where X is OH.
Claim 79
Dependent Claim
11 words
A method according to claim 77 where R 1 is n-hexyl.
Claim 80
Dependent Claim
11 words
a method according to claim 76 where R 2 is methyl.
Claim 81
Dependent Claim
18 words
A method according to claim 49 wherein the compound is used in an amount to impart antiviral activity.
Claim 82
Dependent Claim
10 words
A method according to claim 80 where X is OH.
Claim 83
Dependent Claim
11 words
A method according to claim 81 where R 2 is methyl.
Claim 84
Dependent Claim
11 words
A method according to claim 82 where R 1 is n-hexyl.
Claim 85
Dependent Claim
36 words
A method according to claim 49 wherein the compound is used in an amount to impart anti-leukemic activity, X is OH, R 1 is alkyl of 1 to 8 carbon atoms and R 2 is methyl.
Claim 86
Dependent Claim
11 words
A method according to claim 84 where R 1 is n-hexyl.
Claim 87
Dependent Claim
16 words
A method according to claim 85 wherein the compound is administered to a mammal having leukemia.
Claim 88
Dependent Claim
20 words
A method according to claim 1 wherein when the activity is antiviral the virus is influenza virus or herpes virus.
Claim 89
Dependent Claim
15 words
A method according to claim 39 wherein the virus is influenza virus or herpes virus.
Claim 90
Dependent Claim
10 words
A method according to claim 88 where X is OH.
Claim 91
Dependent Claim
15 words
A method according to claim 80 wherein the virus is influenza virus or herpes virus.
Claim 92
Dependent Claim
10 words
A method according to claim 90 wherein X is OH.
Claim 93
Dependent Claim
11 words
A method according to claim 91 wherein R 2 is methyl.
Claim 94
Dependent Claim
11 words
A method according to claim 92 wherein R 1 is n-hexyl.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-09-09 | 1984-03-10 | 1984-09-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-09-09 | 1988-03-10 | 1988-09-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-09-09 | 1992-03-10 | 1992-09-09 | $7700.00 | Window Closed / Lapsed |