US4548923A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Muramyl peptides and processes for their manufacture
Assignee: Novartis Corp
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Filing: 1984-05-09
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Granted: 1985-10-22
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Expires: 2004-05-09
Abstract
Abstract The compounds of the formula I ##STR1## in which each of R 1 , R 4 and R 6 , independently of the others, represents hydrogen or lower alkanoyl, R 2 represents C 1-4 -alkyl, hydroxymethyl or phenyl, R 3 represents hydrogen or methyl, R 5 represents hydrogen or C 1-3 -alkyl, R 7 represents C 1-3 -alkyl that is unsubstituted or substituted by hydroxy, mercapto or methylthio, R 8 represents hydrogen or lower alkyl, X represents oxygen or the group NH, Y represents C 1-4 -alkylidene, and each of R 9 and R 10 , independently of the other, represents C 11-17 -alkyl or C 11-17 -alkenyl, and their salts, have an immunostimulating activeity.
Inventors
- 👤 Albert Hartmann
- 👤 Oskar Wacker
- 👤 Gerhard Baschang
- 👤 Lajos Tarcsay
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 21:20
CPC Classifications
C; C07; C07K; C07K1/00; C07K1/06; C07K9/00; C07K9/001; C07K9/005; A; A61; A61P; A61P31/00; A61P31/12; A61P35/00; C07K1/12; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
69 words
The compounds of the formula I ##STR20## wherein R 1 , R 4 and R 6 are hydrogen, R 2 is methyl or ethyl, R 3 is hydrogen or methyl, R 5 is hydrogen, R 7 is methyl, R 8 is hydrogen or C 1 -C 4 -alkyl, X is the group NH, Y is ethylidene, and R 9 and R 10 are N-pentadecyl, and their pharmaceutically acceptable salts.
Claim 2
Dependent Claim
69 words
The compounds of the formula I ##STR20## wherein R 1 , R 4 and R 6 are hydrogen, R 2 is methyl or ethyl, R 3 is hydrogen or methyl, R 5 is hydrogen, R 7 is methyl, R 8 is hydrogen or C 1 -C 4 -alkyl, X is the group NH, Y is ethylidene, and R 9 and R 10 are N-pentadecyl, and their pharmaceutically acceptable salts.
Claim 3
Dependent Claim
11 words
N-acetylmuramyl-L-alanyl-D-glutamyl-(C.sub.α)-n-butyl ester-(C.sub.γ)-L-alanine-2-(1,2-dipalmitoyl-sn-glycero-3-hydroxyphosphoryloxy)-ethylamide and its pharmaceutically acceptable salts according to claim 1.
Claim 4
Dependent Claim
11 words
N-Propionyl-demethylmuramyl-L-alanyl-D-glutamyl-(C.sub.α)-n-butyl ester-(C.sub.γ)-L-alanine-2-(1,2-dipalmitoyl-sn-glycero-3-hydroxyphosphoryloxy)-ethylamide and its pharmaceutically acceptable salts according to claim 1.
Claim 5
Dependent Claim
11 words
N-Acetylmuramyl-L-alanyl-D-glutamyl-(C.sub.α)-methyl ester-(C.sub.γ)-L-alanine-2-(1,2-dipalmitoyl-sn-glycero-3-hydroxyphosphoryloxy)-ethylamide and its pharmaceutically acceptable salts according to claim 1.
Claim 6
Dependent Claim
11 words
N-Propionyl-demethylmuramyl-L-alanyl-D-glutamyl-(C.sub.α)-methyl ester-(C.sub.γ)-L-alanine-2-(1,2-dipalmitoyl-sn-glycero-3-hydroxyphosphoryloxy)-ethylamide and its pharmaceutically acceptable salts according to claim 1.
Claim 7
Dependent Claim
7 words
Pharmaceutically acceptable salts according to claim 1.
Claim 8
Dependent Claim
7 words
Pharmaceutically acceptable salts according to claim 6.
Claim 9
Dependent Claim
14 words
Compounds according to claim 1, wherein R 8 is C 1 -C 4 -alkyl.
Claim 10
Dependent Claim
15 words
A compound according to claim 1 which is N-acetylmuramyl-L-alanyl-D-glutamyl-(C.sub.α)-tert.-butyl ester-(C.sub.γ)-L-alanine-2-(1,2-dipalmitoyl-sn-glycero-3-hydroxyphosphoryloxy)-ethylamide and its pharmaceutically acceptable salts.
Claim 11
Dependent Claim
15 words
A compound according to claim 1 which is N-propionyl-demethylmuramyl-L-alanyl-D-glutamyl-(C.sub.α)-tert.-butyl ester-(C.sub.γ)-L-alanine-2-(1,2-dipalmitoyl-sn-glycero-3-hydroxyphosphoryloxy)-ethyl-amide and its pharmaceutically acceptable salts.
Claim 12
Dependent Claim
16 words
A compound according to claim 1 which is N-propionyl-demethylmuramyl-L-alanyl-D-glutamic acid (C.sub.γ)-L-alanine-2-(1,2-dipalmitoyl-sn-glycero-3-hydroxyphosphoryloxy)-ethylamide and its pharmaceutically acceptable salts.
Claim 13
Dependent Claim
16 words
A compound according to claim 1 which is N-acetylmuramyl-L-alanyl-D-glutamic acid (C.sub.γ)-L-alanine-2-(1,2-dipalmitoyl-sn-glycero-3-hydroxyphosphoryloxy)-ethylamide and its pharmaceutically acceptable salts.
Claim 14
Dependent Claim
6 words
Sodium salts according to claim 8.
Claim 15
Dependent Claim
34 words
Pharmaceutical preparations for stimulating the immune system of warm-blooded animals including humans that contain an immunostimulatory effective amount of a compound according to claim 1 together with a significant amount of a pharmaceutical carrier.
Claim 16
Dependent Claim
34 words
Pharmaceutical preparations for stimulating the immune system of warm-blooded animals including humans that contain an immunostimulatory effective amount of a compound according to claim 8 together with a significant amount of a pharmaceutical carrier.
Claim 17
Dependent Claim
31 words
Method of stimulating the immune system of warm-blooded animals including humans by administering to said animals in need of such treatment an effective amount of a compound according to claim 1.
Claim 18
Dependent Claim
36 words
Method of prophylaxis and treatment of warm-blooded animals including humans in the case of virus infections by administering to said animals in need of such treatment an effective amount of a compound according to claim 1.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-10-21 | 1989-04-22 | 1989-10-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-10-21 | 1993-04-22 | 1993-10-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-10-21 | 1997-04-22 | 1997-10-22 | $7700.00 | Window Closed / Lapsed |