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US4297346A
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Pseudopeptides used as medicaments
Assignee: Institut National de la Santé et de la Recherche Médicale
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Filing: 1979-12-07
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Granted: 1981-10-27
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Expires: 1999-12-07
Abstract
Abstract The invention relates to therapeutic agents referred to as 'pseudopeptides' being formed from at least one peptide radical connected by a peptide bond to a therapeutically active molecule or derivative of a therapeutically active molecule. The therapeutic agents of the invention may be in the form of derivatives such as salts, esters and amides. The basis of action of the agents of the invention is the ability of the agents of the invention to cross bodily biological barriers because of the basically peptide structure of the agents. The invention also includes the preparation of the agents of the invention.
Inventors
- 👤 Richard Rips
- 👤 Elisabeth Morier
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 10:21
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; C07D233/64; C07D207/00; C07D207/02; C07D207/04; C07D207/10; C07D207/16; C07D207/18; C07D207/22; C07D207/24; C07D207/26; C07D207/273; C07D207/277; C07D207/28; C07K; C07K5/00; C07K5/04; C07K5/06; C07K5/06139; C07K5/06165; C07K5/06173; C07K5/08; C07K5/0802; C07K5/0812; C07K5/0821; A; A61; A61K; A61K38/00
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
120 words
Pseudopeptide formed by at least one peptide radical originated from a neuropeptide by removal of one of more of the terminal sequences, connected by a peptide bond to a molecule or to a derivative of a therapeutically active molecule acting on the central nervous system, said neuropeptide being selected from the group consisting of endorphine and neuropeptides having from 2 to 11 amino acid sequences and said therapeutically active molecular being selected from the group consisting of amphetamine (Amph), 4-nitro-amphetamine (Amph-NO 2 ), 4-amino-amphetamine (Amph-NH 2 ), 4-chloroamphetamine (Amph-Cl), N-phthaloyl-4-amino-amphetamine, 3,4-dibenzoxyphenyl ethylamine, phenyl ethylamine (PEA), dopamine, 5-(3-aminopropyliden dibenzo-(a,d)-cycloheptadi-1,4-ene (PDD), 1,3-dihydroxy-7-amino 5-phenyl-1H-benzodiazepine-(1,4)-one-(2) (BD), 20-(3-aminopropyl) 3-phenothiazine (PP), 1,5-dimethyl-2-phenyl-4-amino-3-pyrazolone (AP), 4-ethoxyaniline (PT), 4-phenyl-4-ethoxycarbonyl piperidine (NP), tryptamine (Try-NH 2 ) and 4-amino-barbituric acid (AB).
Claim 2
Dependent Claim
120 words
Pseudopeptide formed by at least one peptide radical originated from a neuropeptide by removal of one of more of the terminal sequences, connected by a peptide bond to a molecule or to a derivative of a therapeutically active molecule acting on the central nervous system, said neuropeptide being selected from the group consisting of endorphine and neuropeptides having from 2 to 11 amino acid sequences and said therapeutically active molecular being selected from the group consisting of amphetamine (Amph), 4-nitro-amphetamine (Amph-NO 2 ), 4-amino-amphetamine (Amph-NH 2 ), 4-chloroamphetamine (Amph-Cl), N-phthaloyl-4-amino-amphetamine, 3,4-dibenzoxyphenyl ethylamine, phenyl ethylamine (PEA), dopamine, 5-(3-aminopropyliden dibenzo-(a,d)-cycloheptadi-1,4-ene (PDD), 1,3-dihydroxy-7-amino 5-phenyl-1H-benzodiazepine-(1,4)-one-(2) (BD), 20-(3-aminopropyl) 3-phenothiazine (PP), 1,5-dimethyl-2-phenyl-4-amino-3-pyrazolone (AP), 4-ethoxyaniline (PT), 4-phenyl-4-ethoxycarbonyl piperidine (NP), tryptamine (Try-NH 2 ) and 4-amino-barbituric acid (AB).
Claim 3
Dependent Claim
97 words
A pseudopeptide formed by at least one peptidic radical selected from the group consisting of pGlu-His originated from TRH, Pro-Leu originated from MIF, and Try-Gly-Gly originated from encephaline, said peptidic radical being connected by a ##STR12## bond to a therapeutically active molecule acting on the central nervous system selected from the group consisting of amphetamine (Amph), 4-nitro-amphetamine (Amph-NO 2 ), 4-amino-amphetamine (Amph-NH 2 ), 4-chloroamphetamine (Amph-Cl), N-phthaloyl-4-amino-amphetamine, 3,4-dibenzoxyphenyl ethylamine, phenyl ethylamine (PEA), dopamine, 5-(3-aminopropyliden dibenzo-(a,d)-cycloheptadi-1,4-ene (PPD), 1,3-dihydroxy-7-amino 5-phenyl-1H-benzodiazepine-(1,4)-one-(2) (BD), 20-(3-aminopropyl) 3-phenothiazine (PP), 1,5-dimethyl-2-phenyl-4-amino-3-pyrazolone (AP), 4-ethoxyaniline (PT), 4-phenyl-4-ethoxycarbonyl piperidine (NP), tryptamine (Try-NH 2 ) and 4-aminobarbituric acid (AB).
Claim 4
Dependent Claim
97 words
A pseudopeptide formed by at least one peptidic radical selected from the group consisting of pGlu-His originated from TRH, Pro-Leu originated from MIF, and Try-Gly-Gly originated from encephaline, said peptidic radical being connected by a ##STR12## bond to a therapeutically active molecule acting on the central nervous system selected from the group consisting of amphetamine (Amph), 4-nitro-amphetamine (Amph-NO 2 ), 4-amino-amphetamine (Amph-NH 2 ), 4-chloroamphetamine (Amph-Cl), N-phthaloyl-4-amino-amphetamine, 3,4-dibenzoxyphenyl ethylamine, phenyl ethylamine (PEA), dopamine, 5-(3-aminopropyliden dibenzo-(a,d)-cycloheptadi-1,4-ene (PPD), 1,3-dihydroxy-7-amino 5-phenyl-1H-benzodiazepine-(1,4)-one-(2) (BD), 20-(3-aminopropyl) 3-phenothiazine (PP), 1,5-dimethyl-2-phenyl-4-amino-3-pyrazolone (AP), 4-ethoxyaniline (PT), 4-phenyl-4-ethoxycarbonyl piperidine (NP), tryptamine (Try-NH 2 ) and 4-aminobarbituric acid (AB).
Claim 5
Dependent Claim
39 words
A pseudopeptide formed by a peptidic radical connected by a peptide bond to a central nervous system acting molecule, said pseudopeptide having central nervous system activity and being selected from the group consisting of pGlu-His-Amph, pGlu His-PEA and pGlu-His-DA.
Claim 6
Dependent Claim
39 words
A pseudopeptide formed by a peptidic radical connected by a peptide bond to a central nervous system acting molecule, said pseudopeptide having central nervous system activity and being selected from the group consisting of pGlu-His-Amph, pGlu His-PEA and pGlu-His-DA.
Claim 7
Dependent Claim
41 words
A pseudopeptide formed by a peptidic radical connected by a peptide bond to a central nervous system acting molecule, said pseudopeptide having central nervous system activity and being selected from the group consisting of pGlu-His-Tyr-NH 2 , pGlu-His-PP, pGlu-His-BD and pGlu-His-PDD.
Claim 8
Dependent Claim
41 words
A pseudopeptide formed by a peptidic radical connected by a peptide bond to a central nervous system acting molecule, said pseudopeptide having central nervous system activity and being selected from the group consisting of pGlu-His-Tyr-NH 2 , pGlu-His-PP, pGlu-His-BD and pGlu-His-PDD.
Claim 9
Dependent Claim
40 words
A pseudopeptide formed by a peptidic radical connected by a peptide bond to a central nervous system acting molecule, said pseudopeptide having central nervous system activity and being selected from the group consisting of Pro-Leu-Amph, Pro-Leu-PEA, Pro-Leu-BD, Pro-Leu-PDD and Pro-Leu-PP.
Claim 10
Dependent Claim
40 words
A pseudopeptide formed by a peptidic radical connected by a peptide bond to a central nervous system acting molecule, said pseudopeptide having central nervous system activity and being selected from the group consisting of Pro-Leu-Amph, Pro-Leu-PEA, Pro-Leu-BD, Pro-Leu-PDD and Pro-Leu-PP.
Claim 11
Dependent Claim
63 words
Pseudopeptide of a formula of the group consisting of: pGlu-His-Amph pGlu-His-PEA pGlu-His-Amph-Cl pGlu-His-PEA-di-BzO pGlu-His-DA pGlu-His-Amph-NO 2 pGlu-His-Amph-NH 2 pGlu-His-pNH-Amph-N-Pht pGlu-His-pNH-Amph Cbz-Pro-Leu-Amph Cbz-Pro-Leu-Amph-Cl Cbz-Pro-Leu-PEA Cbz-Pro-Leu-Amph-NO 2 Cbz-Pro-Leu-PEA-di-BzO Pro-Leu-Amph Pro-Leu-Amph-Cl Pro-Leu-PEA Pro-Leu-Amph-NO 2 Pro-Leu-Amph-NH 2 Pro-Leu-DA pGlu-His-PDD.HCl pGlu-His-BD.HCl pGlu-His-PP.Hcl Cbz-Pro-Leu-PDD Cbz-Pro-Leu-BD Cbz-Pro-Leu-PP Pro-Leu-BD Pro-Leu-PDD pGlu-His-PT pGlu-His-AP Cbz-Pro-Leu-AP Cbz-Pro-Leu-PT Cbz-Pro-Leu-NP Pro-Leu-AP Pro-Leu-PT Pro-Leu-NP N-Cbz-(Bzo)-Tyr-Gly-Gly-PT N-Cbz-(Bzo)-Tyr-Gly-Gly-AP Tyr-Gly-Gly-PT Tyr-Gly-Gly-AP pGlu-His-Try-NH 2 pGlu-His-AB Cbz-Pro-Leu-Try-NH 2 Cbz-Pro-Leu-AB Pro-Leu-Try-NH 2 Pro-Leu-AB.
Claim 12
Dependent Claim
63 words
Pseudopeptide of a formula of the group consisting of: pGlu-His-Amph pGlu-His-PEA pGlu-His-Amph-Cl pGlu-His-PEA-di-BzO pGlu-His-DA pGlu-His-Amph-NO 2 pGlu-His-Amph-NH 2 pGlu-His-pNH-Amph-N-Pht pGlu-His-pNH-Amph Cbz-Pro-Leu-Amph Cbz-Pro-Leu-Amph-Cl Cbz-Pro-Leu-PEA Cbz-Pro-Leu-Amph-NO 2 Cbz-Pro-Leu-PEA-di-BzO Pro-Leu-Amph Pro-Leu-Amph-Cl Pro-Leu-PEA Pro-Leu-Amph-NO 2 Pro-Leu-Amph-NH 2 Pro-Leu-DA pGlu-His-PDD.HCl pGlu-His-BD.HCl pGlu-His-PP.Hcl Cbz-Pro-Leu-PDD Cbz-Pro-Leu-BD Cbz-Pro-Leu-PP Pro-Leu-BD Pro-Leu-PDD pGlu-His-PT pGlu-His-AP Cbz-Pro-Leu-AP Cbz-Pro-Leu-PT Cbz-Pro-Leu-NP Pro-Leu-AP Pro-Leu-PT Pro-Leu-NP N-Cbz-(Bzo)-Tyr-Gly-Gly-PT N-Cbz-(Bzo)-Tyr-Gly-Gly-AP Tyr-Gly-Gly-PT Tyr-Gly-Gly-AP pGlu-His-Try-NH 2 pGlu-His-AB Cbz-Pro-Leu-Try-NH 2 Cbz-Pro-Leu-AB Pro-Leu-Try-NH 2 Pro-Leu-AB.
Claim 13
Dependent Claim
27 words
As a novel medicament for asthenia, an effective amount of a pseudopeptide of the class consisting of pGlu-His-Amph and Pro-Leu-Amph together with a pharmaceutically acceptable carrier therefor.
Claim 14
Dependent Claim
27 words
As a novel medicament for asthenia, an effective amount of a pseudopeptide of the class consisting of pGlu-His-Amph and Pro-Leu-Amph together with a pharmaceutically acceptable carrier therefor.
Claim 15
Dependent Claim
28 words
As a novel medicament for sympathomimetric action, an effective amount of a pseudopeptide of the class consisting of pGlu-His-PEA and Pro-Leu-PEA together with a pharmaceutically acceptable carrier therefor.
Claim 16
Dependent Claim
28 words
As a novel medicament for sympathomimetric action, an effective amount of a pseudopeptide of the class consisting of pGlu-His-PEA and Pro-Leu-PEA together with a pharmaceutically acceptable carrier therefor.
Claim 17
Dependent Claim
31 words
As a novel medicament for the treatment of Parkinson's disease, an effective amount of a pseudopeptide of the class consisting of pGlu-His-DA and Pro-Leu-DA together with a pharmaceutically acceptable carrier therefor.
Claim 18
Dependent Claim
31 words
As a novel medicament for the treatment of Parkinson's disease, an effective amount of a pseudopeptide of the class consisting of pGlu-His-DA and Pro-Leu-DA together with a pharmaceutically acceptable carrier therefor.
Claim 19
Dependent Claim
35 words
As a novel medicament for depletion of serotonin, an effective amount of a pseudopeptide of the class consisting of pGlu-His-Amph-NO 2 , pGlu-His-Amph-Cl, Pro-Leu-Amph NO 2 and Pro-Leu-Amph-Cl together with a pharmaceutically acceptable carrier therefor.
Claim 20
Dependent Claim
35 words
As a novel medicament for depletion of serotonin, an effective amount of a pseudopeptide of the class consisting of pGlu-His-Amph-NO 2 , pGlu-His-Amph-Cl, Pro-Leu-Amph NO 2 and Pro-Leu-Amph-Cl together with a pharmaceutically acceptable carrier therefor.
Claim 21
Dependent Claim
31 words
As a novel medicament for increase of serotonin, an effective amount of a pseudopeptide of the class consisting of pGlu-His-Amph-NH 2 and Pro-Leu-Amph-NH 2 together with a pharmaceutically acceptable carrier therefor.
Claim 22
Dependent Claim
31 words
As a novel medicament for increase of serotonin, an effective amount of a pseudopeptide of the class consisting of pGlu-His-Amph-NH 2 and Pro-Leu-Amph-NH 2 together with a pharmaceutically acceptable carrier therefor.
Claim 23
Dependent Claim
28 words
As a novel medicament for antidepressive action, an effective amount of a pseudopeptide of the class consisting of pGlu-His-PPD.HCl, and Pro-Leu-PDD, together with a pharmaceutically acceptable carrier therefor.
Claim 24
Dependent Claim
28 words
As a novel medicament for antidepressive action, an effective amount of a pseudopeptide of the class consisting of pGlu-His-PPD.HCl, and Pro-Leu-PDD, together with a pharmaceutically acceptable carrier therefor.
Claim 25
Dependent Claim
30 words
As a novel medicament for tranquilizing effect, an effective amount of a pseudopeptide of the class consisting of pGlu-His-BD.HCl, pGlu-His-PP.HCl, Pro-Leu-BD and Pro-Leu-PP together with a pharmaceutically acceptable carrier therefor.
Claim 26
Dependent Claim
30 words
As a novel medicament for tranquilizing effect, an effective amount of a pseudopeptide of the class consisting of pGlu-His-BD.HCl, pGlu-His-PP.HCl, Pro-Leu-BD and Pro-Leu-PP together with a pharmaceutically acceptable carrier therefor.
Claim 27
Dependent Claim
28 words
As a novel medicament for anti-epilepsy activity, an effective amount of a pseudopeptide of the class consisting of pGlu-His-AB and Pro-Leu-AB together with a pharmaceutically acceptable carrier therefor.
Claim 28
Dependent Claim
28 words
As a novel medicament for anti-epilepsy activity, an effective amount of a pseudopeptide of the class consisting of pGlu-His-AB and Pro-Leu-AB together with a pharmaceutically acceptable carrier therefor.
Claim 29
Dependent Claim
29 words
As a novel medicament for analgesic activity, an effective amount of a pseudopeptide of the class consisting of pGlu-His-PT, Pro-Leu-PT and Pro-Leu-NP together with a pharmaceutically acceptable carrier therefor.
Claim 30
Dependent Claim
29 words
As a novel medicament for analgesic activity, an effective amount of a pseudopeptide of the class consisting of pGlu-His-PT, Pro-Leu-PT and Pro-Leu-NP together with a pharmaceutically acceptable carrier therefor.
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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) | 1984-10-26 | 1985-04-27 | 1985-10-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-10-26 | 1989-04-27 | 1989-10-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-10-26 | 1993-04-27 | 1993-10-27 | $7700.00 | Window Closed / Lapsed |