US4965250A
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Peptide compounds having a nitrogenous polycyclic structure
Assignee: Institut Servier de Medecine Translationnelle SARL
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Filing: 1988-01-25
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Granted: 1990-10-23
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Expires: 2008-01-25
Abstract
Abstract Tetrapeptide compounds of general formula: <IMAGE> I in which R denotes: a hydrogen atom, a straight- or branched-chain alkyl radical containing from 1 to 4 carbon atoms, an aryl radical such as phenyl or a heterocyclic aromatic radical such as thienyl, optionally substituted with a hydroxy, amino, mercapto, methylthio or lower alkyl group, a lower aralkyl radical such as benzyl, R' denotes a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms, X denotes an oxygen atom or an NH group, Y denotes an oxygen or sulfur atom when X denotes an NH group, or Y denotes an NH group when X denotes an oxygen atom, t denotes 0 or 1, <IMAGE> denotes a nitrogen-containing polycyclic structure, their enantiomers, epimers and diastereoisomers, as well as their addition salts with a pharmaceutically acceptable acid or base. Medicinal products.
Inventors
- 👤 Michel Vincent
- 👤 Georges Remond
- 👤 Claude Cudennec
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 22:38
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/10; C07K5/1024; A; A61; A61P; A61P37/00; A61P37/02; A61P37/04; C07K5/08; C07K5/0815
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
211 words
A compound selected from those of the formula: ##STR15## in which R denotes: a hydrogen atom, a straight- or branched-chain alkyl radical containing from 1 to 4 carbon atoms, phenyl or thienyl, optionally substituted with a hydroxy, amino, mercapto, methylthio or lower alkyl group, benzyl, R' denotes a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms, X denotes an oxygen atom or an NH group, Y denotes an oxygen or sulfur atom when X denotes an NH group, or Y denotes an NH group when X denotes an oxygen atom, t denotes 0 or 1, Lys and Arg denote, respectively, lysyl and arginyl residues engaged in peptide bonds, ##STR16## denotes a bicyclic structure of the formula: ##STR17## where m equals 1 or zero, n and p denote zero, 1 or 2, R a and R b denote a hydrogen atom or can form together a direct bond when p=0, B denotes an alkylene chain (CH 2 ) q where q equals 2, 3 or 4 or an unsaturated structure (--CH=CH--) 2 when p=0 and R a and R b together form a bond, with the proviso that the sum of m, n, p and q is an integer between 3 and 6, or
Claim 2
Dependent Claim
211 words
A compound selected from those of the formula: ##STR15## in which R denotes: a hydrogen atom, a straight- or branched-chain alkyl radical containing from 1 to 4 carbon atoms, phenyl or thienyl, optionally substituted with a hydroxy, amino, mercapto, methylthio or lower alkyl group, benzyl, R' denotes a hydrogen atom or a straight- or branched-chain alkyl group containing from 1 to 4 carbon atoms, X denotes an oxygen atom or an NH group, Y denotes an oxygen or sulfur atom when X denotes an NH group, or Y denotes an NH group when X denotes an oxygen atom, t denotes 0 or 1, Lys and Arg denote, respectively, lysyl and arginyl residues engaged in peptide bonds, ##STR16## denotes a bicyclic structure of the formula: ##STR17## where m equals 1 or zero, n and p denote zero, 1 or 2, R a and R b denote a hydrogen atom or can form together a direct bond when p=0, B denotes an alkylene chain (CH 2 ) q where q equals 2, 3 or 4 or an unsaturated structure (--CH=CH--) 2 when p=0 and R a and R b together form a bond, with the proviso that the sum of m, n, p and q is an integer between 3 and 6, or
Claim 3
Dependent Claim
23 words
2,3,4-tetrahydro-beta-carboline, or an enantiomer, epimer, or diastereoisomer thereof, or an addition salt of any of the foregoing with a pharmaceutically-acceptable acid or base.
Claim 4
Dependent Claim
23 words
2,3,4-tetrahydro-beta-carboline, or an enantiomer, epimer, or diastereoisomer thereof, or an addition salt of any of the foregoing with a pharmaceutically-acceptable acid or base.
Claim 5
Dependent Claim
27 words
A compound as claimed in claim 1, in which the cyclic structure ##STR18## denotes indoline, isoindoline, tetrahydroquinoline, tetrahydroisoquinoline, perhydroindol, perhydroisoindol, perhydroquinoline, perhydroisoquinoline, perhydrocyclopenta[b]-pyrrol, 2-azabicyclo[2.2.2]octane, 2-azabicyclo[2.2.1]-heptane or 1,2,3,4-tetrahydro-beta-carboline.
Claim 6
Dependent Claim
17 words
A compound as claimed in claim 1, in which the cyclic structure ##STR19## denotes perhydroindol or 2-azabicyclo[2.2.2]octane.
Claim 7
Dependent Claim
17 words
Compound of claim 1 being Cyclo(S)Thr-(S)-Lys-(S)ABO-(S)Arg-OH or an addition salt thereof with a pharmaceutically-acceptable acid or base.
Claim 8
Dependent Claim
17 words
Compound of claim 1 being Cyclo(S)Thr-(S)Lys-(S)PHI-(S)Arg-OH or an addition salt thereof with a pharmaceutically-acceptable acid or base.
Claim 9
Dependent Claim
17 words
Compound of claim 1 being Cyclo(S)Thr-(S)Lys-(S)THIQ-(S)Arg-OH or an addition salt thereof with a pharmaceutically-acceptable acid or base.
Claim 10
Dependent Claim
27 words
Compound of claim 1 being Cyclo(S)Thr-(S)Lys-PHII-(S)Arg-OH, or an enantiomer or diastereoisomer thereof, or an addition salt of any of the foregoing with a pharmaceutically-acceptable acid or base.
Claim 11
Dependent Claim
18 words
Compound of claim 1 being Cyclo(2S, 3R)AHPA-(S)Lys-(S)ABO-(S)Arg-OH or an addition salt thereof with a pharmaceutically-acceptable acid or base.
Claim 12
Dependent Claim
25 words
Compound of claim 1 being [(4R)-4-Methyl(-2-oxo-1,3-oxazolidinyl-5-carbonyl]-(S)Lys-(S)ABO-(S)Arg-OH, or an enantiomer thereof, or an addition salt of any of the foregoing with a pharmaceutically-acceptable acid or base.
Claim 13
Dependent Claim
25 words
Compound of claim 1 being CycloGABOB-(S)Lys-(S)ABO-(S)Arg-OH, or an enantiomer thereof, or an addition salt of any of the foregoing with a pharmaceutically-acceptable acid or base.
Claim 14
Dependent Claim
38 words
A pharmaceutical composition useful for stimulation of the natural immune system containing as active principle an effective amount of at least one compound as claimed in claim 1, in combination with one or more pharmaceutically-acceptable excipients or vehicles.
Claim 15
Dependent Claim
45 words
A composition as claimed in claim 11, in which the cyclic structure of the compound of Formula I NA'-CH denotes perhydroindol or 2-azabicyclo[2.2.2]octane, or an enantiomer, epimer or diastereoisomer thereof, or an addition salt or any of the foregoing with a pharmaceutically-acceptable acid or base.
Claim 16
Dependent Claim
40 words
A method for treating a living animal in need of stimulation of the natural immune system comprising the step of administering to the said living animal an amount of a compound of claim 1 which is effective for such stimulation.
Claim 17
Dependent Claim
45 words
A method as claimed in claim 13, in which the cyclic structure of the compound of Formula I ##STR20## denotes perhydroindol or 2-azabicyclo[2.2.2]octane, or an enantiomer, epimer, or diastereoisomer thereof, or an addition salt of any of the foregoing with a pharmaceutically-acceptable acid or base.
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) | 1993-10-22 | 1994-04-23 | 1994-10-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-10-22 | 1998-04-23 | 1998-10-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-10-22 | 2002-04-23 | 2002-10-23 | $7700.00 | Window Closed / Lapsed |