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US4164571A
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Medicament which antagonizes the action of gastrin and related polypeptides
Assignee: Institut National de la Santé et de la Recherche Médicale
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Filing: 1977-09-21
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Granted: 1979-08-14
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Expires: 1997-09-21
Abstract
Abstract The present invention relates to a method of treating diseases and particularly gastroduodenal ulcers linked to an hypersecretion of gastrin, and to polypeptide amide derivatives which can be used in this method as therapeutic agents and more specifically as antagonists of the action of gastrin and related polypeptides relative to their specific biological receptors. This method comprises administering a therapeutically effective amount of a polypeptide amide derivative of general formula: ##STR1## in which R 1 represents a hydrogen atom or an acyl radical and R 2 represents a substituted or unsubstituted aryl radical e.g. nitrophenyl group or dinitrophenyl group such as 2-nitrophenyl or 2-4-dinitrophenyl.
Inventors
- 👤 Serge J. E. Bonfils
- 👤 Juliette M. Dubrasquet
- 👤 Pierre Fromageot
- 👤 Jean P. Girma
- 👤 Miguel Lewin
- 👤 Jean L. Morgat
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 05:56
CPC Classifications
C; C07; C07K; C07K14/00; C07K14/435; C07K14/575; C07K14/595; A; A61; A61P; A61P1/00; A61P1/04; A61K; A61K38/00
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
111 words
A medicament, which comprises as active substance a polypeptide amide derivative of general formula: ##STR8## in which R 1 represents a hydrogen atom, an amino acid radical, a N-t-butyloxycarbonyl-L-amino acid radical, a N-benzyloxycarbonyl amino acid radical or a N-benzoyl amino acid radical, wherein the term amino acid radical means an amino acid radical selected from the group consisting of β-alanyl, glycyl, pyroglutamyl, N-benzoyl glycyl, N-t-butyloxycarbonyl-L-glycyl, N-t-butyloxycarbonyl-L-alanyl, lysile and N benzyloxy-carbonyl-L-propyl or a peptide radical selected from the group consisting of: L-pyroglutamyl-L-glycyl-L-prolyl-L-tryptophanyl-L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-L-glycyl, L-pyroglutamyl-L-glycyl-L-propyl-L-typtophanyl L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-(oxysulphonic in the 4-position of the phenyl nucleus), L-pyroglutamyl-L-glutamyl-L-aspartyl-L-tyrosyl-L-threonyl-L-glucyl, N-t-butyloxycarbonyl-L-aspartyl-L-tyrosyl-L-methionyl-L-glycyl, L-pyroglutamyl-L-leucyl-L-glycyl-L-prolyl-L-glutaminyl-L-glycyl-L-histidyl-L-prolyl-L-seryl-L-leucyl-L-valyl-L-alanyl-L-aspartyl-L-prolyl-L-seryl-L-lysyl-L-lysyl-L-glutaminyl-L-glycyl-L-propyl-L-tryptophanyl-L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glu amyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-L-glycyl, L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-L-glycyl, and L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-(oxysulphonic in the 4-position of the phenyl nucleus)-L-glycyl, and R 2 represents 2-nitrophenyl or 2,4-dinitrophenyl.
Claim 2
Dependent Claim
111 words
A medicament, which comprises as active substance a polypeptide amide derivative of general formula: ##STR8## in which R 1 represents a hydrogen atom, an amino acid radical, a N-t-butyloxycarbonyl-L-amino acid radical, a N-benzyloxycarbonyl amino acid radical or a N-benzoyl amino acid radical, wherein the term amino acid radical means an amino acid radical selected from the group consisting of β-alanyl, glycyl, pyroglutamyl, N-benzoyl glycyl, N-t-butyloxycarbonyl-L-glycyl, N-t-butyloxycarbonyl-L-alanyl, lysile and N benzyloxy-carbonyl-L-propyl or a peptide radical selected from the group consisting of: L-pyroglutamyl-L-glycyl-L-prolyl-L-tryptophanyl-L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-L-glycyl, L-pyroglutamyl-L-glycyl-L-propyl-L-typtophanyl L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-(oxysulphonic in the 4-position of the phenyl nucleus), L-pyroglutamyl-L-glutamyl-L-aspartyl-L-tyrosyl-L-threonyl-L-glucyl, N-t-butyloxycarbonyl-L-aspartyl-L-tyrosyl-L-methionyl-L-glycyl, L-pyroglutamyl-L-leucyl-L-glycyl-L-prolyl-L-glutaminyl-L-glycyl-L-histidyl-L-prolyl-L-seryl-L-leucyl-L-valyl-L-alanyl-L-aspartyl-L-prolyl-L-seryl-L-lysyl-L-lysyl-L-glutaminyl-L-glycyl-L-propyl-L-tryptophanyl-L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glu amyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-L-glycyl, L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-L-glycyl, and L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-(oxysulphonic in the 4-position of the phenyl nucleus)-L-glycyl, and R 2 represents 2-nitrophenyl or 2,4-dinitrophenyl.
Claim 3
Dependent Claim
11 words
A medicament according to claim 1, wherein R 2 is 2-nitrophenyl.
Claim 4
Dependent Claim
11 words
A medicament according to claim 1 wherein R 2 is 2-4-dinitrophenyl.
Claim 5
Dependent Claim
23 words
A medicament according to claim 1, wherein R 1 is an acyl radical chosen from the group comprising N-t-butyloxycarbonylbeta-alanyl, N-t-butyloxycarbonyl-glycyl, beta-alanyl and glycyl.
Claim 6
Dependent Claim
16 words
A medicament according to claim 4 wherein R 1 is N-t-butyloxycarbonyl-β-alanyl and R 2 is 2-nitrophenyl.
Claim 7
Dependent Claim
17 words
The medicament of claim 1 wherein R 1 is a hydrogen atom and R 2 is 2-nitrophenyl.
Claim 8
Dependent Claim
15 words
The medicament of claim 4 wherein R 1 is N-t-butyoxycarbonyl-L-glycyl and R 2 is 2-nitrophenyl.
Claim 9
Dependent Claim
17 words
The medicament of claim 1 wherein R 1 is a hydrogen atom and R 2 is 2-nitrophenyl.
Claim 10
Dependent Claim
26 words
A medicament according to claim 1, wherein the polypeptide amide derivative is orthonitrophenyl sulphenylated gastrin in the 2-position of the indole nucleus of its tryptophanyl groups.
Claim 11
Dependent Claim
31 words
A medicament according to claim 1, wherein the polypeptide amide derivative is orthonitrophenyl sulphenylated gastrin in the 2-position of the indole nucleus of its tryptophanyl group connected to the methionyl group.
Claim 12
Dependent Claim
27 words
A medicament according to claim 1, wherein the said polypeptide amide derivative is orthonitrophenyl sulphenylated caerulein in the 2-position of the indole nucleus of its tryptophanyl group.
Claim 13
Dependent Claim
26 words
A medicament according to claim 1, wherein the polypeptide amide derivative is orthonitrophenyl sulphenylated cholecystoquinone in the 2-position of the indole nucleus of its tryptophanyl group.
Claim 14
Independent Claim
124 words
A method of treating gastroduodenal ulcers linked to an hypersecretion of gastrin which comprises administering a therapeutically effective amount of a polypeptide amide derivative of general formula: ##STR9## in which R 1 represents a hydrogen atom, an amino acid radical, a N-t-butyloxycarbonyl-L-amino acid radical, a N-benzyloxycarbonyl amino acid radical or a N-benzoyl amino acid radical, wherein the term amino acid radical means an amino acid radical selected from the group consisting of β-alanyl, glycyl, pyroglutamyl, N-benzoyl glycyl, N-t-butyl-oxycarbonyl-L-glycyl, N-t-butyloxycarbonyl-L-alanyl, lysile and N benzyloxy-carbonyl-L-prolyl or a peptide radical selected from the group consisting of: L-pyroglutamyl-L-glycyl-L-propyl-L-tryptophanyl-L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-L-glycyl, L-pyroglutamyl-L-glycyl-L-propyl-L-tryptophanyl L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-(oxysulphonic in the 4-position of the phenyl nucleus), L-pyroglutamyl-L-glutamyl-L-aspartyl-L-tyrosyl-L-threonyl-L-glycyl, N-t-butyloxycarbonyl-L-aspartyl-L-tyrosyl-L-methionyl-L-glycyl, L-pyroglutamyl-L-leucyl-L-glycyl-L-prolyl-L-glutaminyl-L-glycyl-L-histidyl-L-prolyl-L-seryl-L-leucyl-L-valyl-L-alanyl-L-aspartyl-L-prolyl-L-seryl-L-lysyl-L-lysyl-L-glutaminyl-L-glycyl-L-prolyl-L-tryptophanyl-L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glu amyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-L-glycyl, L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-L-glycyl, and L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-(oxysulphonic in the 4-position of the phenyl nucleus)-L-glycyl and R 2 represents 2-nitrophenyl or 2,4-dinitrophenyl.
Claim 15
Independent Claim
124 words
A method of treating gastroduodenal ulcers linked to an hypersecretion of gastrin which comprises administering a therapeutically effective amount of a polypeptide amide derivative of general formula: ##STR9## in which R 1 represents a hydrogen atom, an amino acid radical, a N-t-butyloxycarbonyl-L-amino acid radical, a N-benzyloxycarbonyl amino acid radical or a N-benzoyl amino acid radical, wherein the term amino acid radical means an amino acid radical selected from the group consisting of β-alanyl, glycyl, pyroglutamyl, N-benzoyl glycyl, N-t-butyl-oxycarbonyl-L-glycyl, N-t-butyloxycarbonyl-L-alanyl, lysile and N benzyloxy-carbonyl-L-prolyl or a peptide radical selected from the group consisting of: L-pyroglutamyl-L-glycyl-L-propyl-L-tryptophanyl-L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-L-glycyl, L-pyroglutamyl-L-glycyl-L-propyl-L-tryptophanyl L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-(oxysulphonic in the 4-position of the phenyl nucleus), L-pyroglutamyl-L-glutamyl-L-aspartyl-L-tyrosyl-L-threonyl-L-glycyl, N-t-butyloxycarbonyl-L-aspartyl-L-tyrosyl-L-methionyl-L-glycyl, L-pyroglutamyl-L-leucyl-L-glycyl-L-prolyl-L-glutaminyl-L-glycyl-L-histidyl-L-prolyl-L-seryl-L-leucyl-L-valyl-L-alanyl-L-aspartyl-L-prolyl-L-seryl-L-lysyl-L-lysyl-L-glutaminyl-L-glycyl-L-prolyl-L-tryptophanyl-L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glu amyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-L-glycyl, L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-L-glycyl, and L-leucyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-glutamyl-L-alanyl-L-tyrosyl-(oxysulphonic in the 4-position of the phenyl nucleus)-L-glycyl and R 2 represents 2-nitrophenyl or 2,4-dinitrophenyl.
Claim 16
Dependent Claim
28 words
A method according to claim 13, wherein the polypeptide amide derivative is a polypeptide amide derivative of general formula (I) in which R 2 is a 2-nitrophenyl group.
Claim 17
Dependent Claim
28 words
A method according to claim 13, wherein the polypeptide amide derivative is a polypeptide amide derivative of general formula (I) in which R 2 is a 2-4-dinitrophenyl group.
Claim 18
Dependent Claim
38 words
A method according to claim 13, wherein the polypeptide amide derivative is a polypeptide amide derivative of general formula (I) in which R 1 is an acyl radical chosen from the group comprising N-t-butyloxycarbonyl-beta-alanyl, N-t-butyloxycarbonylglycyl, beta-alanyl and glycyl.
Claim 19
Dependent Claim
26 words
A method according to claim 13, wherein the polypeptide amide derivative is orthonitrophenyl sulphenylated gastrin in the 2-position of the indole nucleus of its tryptophanyl groups.
Claim 20
Dependent Claim
31 words
A method according to claim 13, wherein the polypeptide amide derivative is orthonitrophenyl sulphenylated gastrin in the 2-position of the indole nucleus of its tryptophanyl group connected to the methionyl group.
Claim 21
Dependent Claim
26 words
A method according to claim 13, wherein the polypeptide amide derivative is orthonitrophenyl sulphenylated caerulein in the 2-position of the indole nucleus of its tryptophanyl group.
Claim 22
Dependent Claim
26 words
A method according to claim 13, wherein the polypeptide amide derivative is orthonitrophenyl sulphenylated cholecystoquinone in the 2-position of the indole nucleus of its tryptophanyl group.
Claim 23
Dependent Claim
16 words
A medicament according to claim 13 wherein R 1 is N-t-butyloxycarbonyl-β-alanyl and R 2 is 2-nitrophenyl.
Claim 24
Dependent Claim
15 words
The medicament of claim 13 wherein R 1 is N-t-butyoxycarbonyl-L-glycyl and R 2 is 2-nitrophenyl.
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) | 1982-08-13 | 1983-02-12 | 1983-08-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-08-13 | 1987-02-12 | 1987-08-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-08-13 | 1991-02-12 | 1991-08-14 | $7700.00 | Window Closed / Lapsed |