Patent US4540683A successfully refreshed from Google Patents.
US4540683A
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US
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In vitro and in vivo treatment of cancer cells and treatment of viruses with a tripeptide compound
Assignee: Proter SpA
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Filing: 1984-06-18
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Granted: 1985-09-10
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Expires: 2004-06-18
Abstract
Abstract The cancericidal activity of all the permutations of a tripeptide compound formed from dichlorodiethylaminophenylalanine, parafluorophenylalanine and methionine bonded together with peptide links was demonstrated using seven in vitro tumor cell lines. The viabilities of each of the tumor cell lines were significantly reduced by treatment for 1 to 24 hours with 1 to 50 ug of the tripeptide per ml of carrier solvent. A pulse exposure to the tripeptide demonstrated that the reductions in tumor cell was comparable to continuous exposure. Other in vitro tests were all conducted on AKR mice. Methods of treating virus by exposing the virus to one of the noted tripeptide compounds is also contemplated. Methods of treating tumor cells with the tripeptides dissolved in a solvent consisting of dimethylacetamide, propylene glycol and absolute ethanol are also contemplated by the present invention.
Inventors
- 👤 Augusto DeBarbieri
- 👤 Julius G. Bekesi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 15:54
CPC Classifications
C; C07; C07H; C07H13/00; C07H13/02; C07H13/04; C07H15/00; C07H15/02; C07H15/04
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
39 words
A method of interfering with virus replication comprising: exposing a soft tissue oncogenic virus to a therapeutically effective dose of a tripeptide compound selected from the group: (1) 3-(p-fluorophenyl)-L-alanyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-L-methionine (2) 3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-3-(p-fluorophenyl)-L-alanyl-L-methionine (3) 3-(p-fluorophenyl)-L-alanyl-L-methionyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanine (4) 3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-L-methionyl-3-(p-fluorophenyl)-L-alanine (5) L-methionyl-3-(p-fluorophenyl)-L-alanyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanine (6) L-methionyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-3-(p-fluorophenyl)-L-alanine.
Claim 2
Independent Claim
39 words
A method of interfering with virus replication comprising: exposing a soft tissue oncogenic virus to a therapeutically effective dose of a tripeptide compound selected from the group: (1) 3-(p-fluorophenyl)-L-alanyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-L-methionine (2) 3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-3-(p-fluorophenyl)-L-alanyl-L-methionine (3) 3-(p-fluorophenyl)-L-alanyl-L-methionyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanine (4) 3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-L-methionyl-3-(p-fluorophenyl)-L-alanine (5) L-methionyl-3-(p-fluorophenyl)-L-alanyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanine (6) L-methionyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-3-(p-fluorophenyl)-L-alanine.
Claim 3
Dependent Claim
14 words
The method of claim 1, wherein the tripeptide compound is 3-(p-fluorophenyl)-L-alanyl-3-[m-bis(2-chlorethyl)aminophenyl]-L-alanyl-L-methionine ethyl ester hydrochloride.
Claim 4
Dependent Claim
13 words
The method of claim 2, wherein the virus is a herpes virus ateles.
Claim 5
Dependent Claim
12 words
The method of claim 2, wherein the virus is Epstein Barr virus.
Claim 6
Dependent Claim
14 words
The method of claim 2, wherein the virus is a mouse mammary tumor virus.
Claim 7
Dependent Claim
12 words
The method of claim 2, wherein the virus is murine leukemia virus.
Claim 8
Dependent Claim
13 words
The method of claim 2, wherein the virus is a gross leukemia virus.
Claim 9
Dependent Claim
12 words
The method of claim 2, wherein the virus is a B-Type retrovirus.
Claim 10
Dependent Claim
22 words
The method of claim 1 wherein the interfering with virus replication is accomplished by administering to host cells 3-(p-fluorophenyl)-L-alanyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-L-methionine ethyl ester hydrochloride.
Claim 11
Dependent Claim
14 words
The method of claim 9 wherein the host cells are MJY-alpha murine mammary cells.
Claim 12
Dependent Claim
39 words
The method of claim 10 wherein there is from 5 to 50 ug of 3-(p-fluorophenyl)-L-alanyl-3-[m-bis(2-chloroethyl)amino-phenyl]-L-alanyl-L-methionine ethyl ester hdyrochloride per milliliter of a medium surrounding the host cells and in contact with the host cells for 30 to 60 minutes.
Claim 13
Dependent Claim
20 words
The method of claim 10 wherein the host cell after administration of 3-(p-fluorophenyl)-L-alanyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-L-methionine ethyl ester hydrochloride are injeected into animals.
Claim 14
Dependent Claim
12 words
The method of claim 10 wherein the host cells are in vitro.
Claim 15
Dependent Claim
18 words
The method of claim 9 wherein the host cells are administered multiple doses of 3-(p-fluorophenyl)-L-alanyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-L-methionine ethyl ester hydrochloride.
Claim 16
Independent Claim
66 words
A method of interfering with virus replication comprising: exposing a virus to a therapeutically effective dose of a tripeptide compound selected from the group: (1) 3-(p-fluorophenyl)-L-alanyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-L-methionine (2) 3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-3-(p-fluorophenyl)-L-alanyl-L-methionine (3) 3-(p-fluorophenyl)-L-alanyl-L-methionyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanine (4) 3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-L-methionyl-3-(p-fluorophenyl)-L-alanine (5) L-methionyl-3-(p-fluorophenyl)-L-alanyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanine (6) L-methionyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-3-(p-fluorophenyl)-L-alanine, and wherein said virus is a member selected from the group consisting of a herpes virus ateles, an Epstein Barr virus, a murine leukemia virus and a gross leukemia virus.
Claim 17
Independent Claim
66 words
A method of interfering with virus replication comprising: exposing a virus to a therapeutically effective dose of a tripeptide compound selected from the group: (1) 3-(p-fluorophenyl)-L-alanyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-L-methionine (2) 3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-3-(p-fluorophenyl)-L-alanyl-L-methionine (3) 3-(p-fluorophenyl)-L-alanyl-L-methionyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanine (4) 3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-L-methionyl-3-(p-fluorophenyl)-L-alanine (5) L-methionyl-3-(p-fluorophenyl)-L-alanyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanine (6) L-methionyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-3-(p-fluorophenyl)-L-alanine, and wherein said virus is a member selected from the group consisting of a herpes virus ateles, an Epstein Barr virus, a murine leukemia virus and a gross leukemia virus.
Claim 18
Dependent Claim
14 words
The method of claim 15, wherein the tripeptide compound is 3-(p-fluorophenyl)-L-alanyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-L-methionine ethyl ester hydrochloride.
Claim 19
Dependent Claim
22 words
The method of claim 15 wherein the interfering with virus replication is accomplished by administering to host cells 3-(p-fluorophenyl)-L-alanyl-3[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-L-methionine ethyl ester hydrochloride.
Claim 20
Dependent Claim
14 words
The method of claim 17 wherein the host cells are MJY-alpha murine mammary cells.
Claim 21
Dependent Claim
39 words
The method of claim 18 wherein there is from 5 to 50 ug of 3-(p-fluorophenyl)-L-alanyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-L-methionine ethyl ester hydrochloride per milliliter of a medium surrounding the host cells and in contact with the host cells for 30 to 60 minutes.
Claim 22
Dependent Claim
20 words
The method of claim 17 wherein the host cell after administration of 3-(p-fluorophenyl)-L-alanyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-L-methionine ethyl ester hydrochloride are injected into animals.
Claim 23
Dependent Claim
12 words
The method of claim 18 wherein the host cells are in vitro.
Claim 24
Dependent Claim
19 words
The method of claim 17 wherein the host cells are administered with multple doses of 3-(p-fluorophenyl)-L-alanyl-3-[m-bis(2-chloroethyl)aminophenyl]-L-alanyl-L-methionine ethyl ester hydrochloride.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-09-09 | 1989-03-11 | 1989-09-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-09-09 | 1993-03-11 | 1993-09-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-09-09 | 1997-03-11 | 1997-09-10 | $7700.00 | Window Closed / Lapsed |