Patent US4276288A successfully refreshed from Google Patents.
US4276288A
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Dehydrooligopeptides, their production and their medicinal use
Assignee: Troponwerke GmbH
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Filing: 1979-10-09
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Granted: 1981-06-30
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Expires: 1999-10-09
Abstract
Abstract New dehydrooligopepetides which bear, as one terminal substituent, an optionally substituted alkyl or alkenyl, optionally substituted aryl, optionally substituted heterocyclic radical, optionally substituted aralkyl or aralkenyl or a carbamoyl group and as the other terminal substituent a hydroxyl or amino, an optionally substituted alkylamino, optionally substituted arylamino, optionally substituted aralkylamino, an optionally substituted nitrogen-containing heterocyclic radical with five or six ring members optionally containing a further heteroatom, optionally substituted aralkoxy, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted alkylthio group or optionally substituted hydrazine demonstrate histolytic and tumor-resolving activity. The compounds are prepared by either hydrolyzing or aminolyzing the corresponding 2,4-disubstituted 5(4H)-oxazolones.
Inventors
- 👤 Eugen Etschenberg
- 👤 Wolfgang Opitz
- 👤 Siegfried Raddatz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 19:35
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/06; C07K5/06008; C07K5/06017; C07K5/06034; A; A61; A61P; A61P35/00; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/54; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/54; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/24; C07D333/26; C07D333/38; C07K5/06078; C07K5/06139; C07K5/08; C07K5/0802; C07K5/0812; C07K5/0821
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
273 words
A dehydrooligopeptide of the following formula or its salts ##STR13## in which R 1 is straight-chain or branched C 1 -C 6 -alkyl which is unsubstituted or substituted by 1 to 3 halogenatoms or C 1 -C 3 -alkoxy; phenyl, styryl or thienyl R 2 is hydrogen or C 1 -C 4 -alkyl R 3 is phenyl, naphthyl, C 4 -C 6 -cycloalkyl, C 1 -C 4 -alkyl, an unsaturated heterocyclic radical which is unsubstituted or substituted by nitro R 2 and R 3 together with the carbon atom to which they are attached represent cyclopentylidene, cyclohexylidene, cyclopentenylidene or cyclohexenylidene R 4 is hydrogen, methyl or ethyl R 5 is phenyl substituted by 1 to 3 halogen atoms or a heterocyclic group which is unsubstituted and contains 5 to 7 ring members and 1 to 2 nitrogen, oxygen or sulphur atoms R 6 is hydrogen R 7 is benzyl substituted by 1 or 2 halogen atoms or by hydroxyl or nitro; 2-methylmercaptoethyl or carboxymethyl; R 8 is hydrogen R 9 is hydroxyl or amino, C 1 -C 10 -alkylamino, C 1 -C 5 -alkoxy, C 1 -C 10 -alkylamino further substituted by 1 to 3 amino groups or by dialkylamino and m and n are the same or different and each represents the number 0 or the number 1, provided that m and n are not simultaneously the number 0; and provided that when R 1 is methyl, R 2 is hydrogen, R 3 is phenyl, m represents 0, R 6 is hydrogen, R 9 is hydroxyl, R 8 is hydrogen and n is 1, R 7 does not represent the 4-hydroxybenzyl radical.
Claim 2
Dependent Claim
273 words
A dehydrooligopeptide of the following formula or its salts ##STR13## in which R 1 is straight-chain or branched C 1 -C 6 -alkyl which is unsubstituted or substituted by 1 to 3 halogenatoms or C 1 -C 3 -alkoxy; phenyl, styryl or thienyl R 2 is hydrogen or C 1 -C 4 -alkyl R 3 is phenyl, naphthyl, C 4 -C 6 -cycloalkyl, C 1 -C 4 -alkyl, an unsaturated heterocyclic radical which is unsubstituted or substituted by nitro R 2 and R 3 together with the carbon atom to which they are attached represent cyclopentylidene, cyclohexylidene, cyclopentenylidene or cyclohexenylidene R 4 is hydrogen, methyl or ethyl R 5 is phenyl substituted by 1 to 3 halogen atoms or a heterocyclic group which is unsubstituted and contains 5 to 7 ring members and 1 to 2 nitrogen, oxygen or sulphur atoms R 6 is hydrogen R 7 is benzyl substituted by 1 or 2 halogen atoms or by hydroxyl or nitro; 2-methylmercaptoethyl or carboxymethyl; R 8 is hydrogen R 9 is hydroxyl or amino, C 1 -C 10 -alkylamino, C 1 -C 5 -alkoxy, C 1 -C 10 -alkylamino further substituted by 1 to 3 amino groups or by dialkylamino and m and n are the same or different and each represents the number 0 or the number 1, provided that m and n are not simultaneously the number 0; and provided that when R 1 is methyl, R 2 is hydrogen, R 3 is phenyl, m represents 0, R 6 is hydrogen, R 9 is hydroxyl, R 8 is hydrogen and n is 1, R 7 does not represent the 4-hydroxybenzyl radical.
Claim 3
Dependent Claim
86 words
A dehydrooligopeptide of claim 1, in which R 1 is methyl, phenyl, thienyl; R 2 is hydrogen or methyl; R 3 is phenyl, ##STR14## naphthyl, cyclohexyl or ethyl; R 2 and R 3 together with the carbon atom to which they are attached stand for cyclohexglidene or cyclohexenylidene; R 4 is hydrogen; R 5 is ##STR15## R 6 is hydrogen; R 7 is ##STR16## R 9 is OH, OCH 3 , ##STR17## --NH--(CH 2 ) 6 --NH 2 or --NH--(CH 2 ) 4 --NH 2 .
Claim 4
Dependent Claim
14 words
A compound of claim 1 or 2, wherein each halogen is fluorine or chlorine.
Claim 5
Dependent Claim
19 words
A compound of claim 1 or 2, wherein m represents the number 0 and n represents the number 1.
Claim 6
Dependent Claim
19 words
A compound of claim 1 or 2, wherein m represents the number 1 and n represents the number 0.
Claim 7
Dependent Claim
100 words
A compound according to claim 1 or 2, which is a dehydrooligopeptide of the formula or its salts ##STR18## in which R I is alkyl having from one to four carbon atoms or phenyl or styryl, R II is a hydrogen atom, R III is thienyl, furyl, or cycloalkyl having five or six carbon atoms, R VI is a hydrogen atom, R VIII is the 4-hydroxybenzyl radical, 4-nitro-benzyl radical or the 4-chlorobenzyl radical, the 2-methylmercaptoethyl radical or the carboxymethyl radical, R VIII is a hydrogen atom, and R IX is hydroxyl or alkoxy having from one to four carbon atoms.
Claim 8
Dependent Claim
15 words
A compound according to claim 1 or 2 in the form of a racemic mixture.
Claim 9
Dependent Claim
16 words
A compound according to claim 1 or 2 in the form of an optically pure isomer.
Claim 10
Dependent Claim
16 words
A compound according to claim 1 or 2 in the form of a pharmaceutically acceptable salt.
Claim 11
Dependent Claim
9 words
A compound according to claim 2 which is N-Benzoyl-2-cyclohexylidenglycyl-L-tyrosine.
Claim 12
Dependent Claim
9 words
A compound according to claim 2 which is N-Benzoyldehydro-3-(2-thienyl)alanyl-L-proline.
Claim 13
Dependent Claim
9 words
A compound according to claim 2 which is N-Acetyldehydro-3-(2-thienyl)alanul-L-tyrosine.
Claim 14
Dependent Claim
11 words
A compound according to claim 2 which is N-Phenacetyldehydro-3-(2-thienyl)alanyl-L-tyrosine tert.-butyl ester.
Claim 15
Dependent Claim
9 words
A compound according to claim 2 which is N-Benzoyl-3-methyl-3-(2-thienyl)dehydroalanyl-L-tyrosine.
Claim 16
Dependent Claim
10 words
A compound according to claim 2 which is N-Benzoyldehydro-3-(2-thienyl)alanyl-L-tyrosine amide.
Claim 17
Dependent Claim
58 words
A pharmaceutical composition containing as an active ingredient an effective amount of 1 to 100 mg of a compound according to claim 1 in admixture with a solid or liquefied gaseous diluent or in admixture with a liquid diluent other than a solvent of a molecular weight less than 200 except in the presence of a surface-active agent.
Claim 18
Dependent Claim
19 words
A pharmaceutical composition according to claim 16, wherein the effective amount of active ingredient is 2 to 40 mg.
Claim 19
Dependent Claim
28 words
A pharmaceutical composition containing as an active ingredient an effective amount of a compound according to claim 16 in the form of a sterile or isotonic aqueous solution.
Claim 20
Dependent Claim
18 words
A composition according to claim 16 containing from 1 to 90% by weight of the said active ingredient.
Claim 21
Dependent Claim
27 words
A medicament in dosage unit form comprising an effective amount of 1 to 100 mg of a compound of claim 1 together with an inert pharmaceutical carrier.
Claim 22
Dependent Claim
10 words
A medicament of claim 20 in the form of ampoules.
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) | 1984-06-29 | 1984-12-29 | 1985-06-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-06-29 | 1988-12-29 | 1989-06-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-06-29 | 1992-12-29 | 1993-06-30 | $7700.00 | Window Closed / Lapsed |