FR2471970A1 - Pentapeptides homologues d'enkephalines, leur preparation et leur utilisation therapeutique - Google Patents
Pentapeptides homologues d'enkephalines, leur preparation et leur utilisation therapeutique Download PDFInfo
- Publication number
- FR2471970A1 FR2471970A1 FR8026691A FR8026691A FR2471970A1 FR 2471970 A1 FR2471970 A1 FR 2471970A1 FR 8026691 A FR8026691 A FR 8026691A FR 8026691 A FR8026691 A FR 8026691A FR 2471970 A1 FR2471970 A1 FR 2471970A1
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- Prior art keywords
- gly
- tyr
- phe
- radical
- ala
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- 210000003141 lower extremity Anatomy 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 229940078547 methylserine Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001749 primary amide group Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/665—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans derived from pro-opiomelanocortin, pro-enkephalin or pro-dynorphin
- C07K14/70—Enkephalins
- C07K14/702—Enkephalins with at least 1 amino acid in D-form
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Gastroenterology & Hepatology (AREA)
- Zoology (AREA)
- Toxicology (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/104,348 US4283329A (en) | 1979-12-17 | 1979-12-17 | Pharmacologically active peptides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2471970A1 true FR2471970A1 (fr) | 1981-06-26 |
| FR2471970B1 FR2471970B1 (enExample) | 1984-11-16 |
Family
ID=22300018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8026691A Granted FR2471970A1 (fr) | 1979-12-17 | 1980-12-16 | Pentapeptides homologues d'enkephalines, leur preparation et leur utilisation therapeutique |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4283329A (enExample) |
| EP (1) | EP0030848B1 (enExample) |
| JP (1) | JPS5697257A (enExample) |
| KR (1) | KR850000476B1 (enExample) |
| BE (1) | BE886677A (enExample) |
| CH (1) | CH646686A5 (enExample) |
| DE (1) | DE3070184D1 (enExample) |
| FR (1) | FR2471970A1 (enExample) |
| GB (1) | GB2065132B (enExample) |
| HU (1) | HU186375B (enExample) |
| IE (1) | IE50883B1 (enExample) |
| IL (1) | IL61703A (enExample) |
| IT (1) | IT1141135B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI770219A7 (enExample) | 1976-02-02 | 1977-08-03 | Sandoz Ag | |
| EP0044451B1 (en) * | 1980-07-17 | 1984-04-18 | Sandoz Ag | Novel pentapeptides, processes for their production, pharmaceutical compositions comprising said pentapeptides and their use |
| FR2488253A1 (fr) * | 1980-08-08 | 1982-02-12 | Roques Bernard | Nouveaux peptides et leur application en therapeutique |
| US4322339A (en) * | 1980-10-20 | 1982-03-30 | Eli Lilly And Company | Pharmacologically active peptides |
| DK134784A (da) * | 1983-03-07 | 1984-09-08 | Lilly Co Eli | Farmakologisk virksomme tripeptid-derivater og fremgangsmaade til fremstilling deraf |
| US5952465A (en) * | 1993-04-23 | 1999-09-14 | Virginia Commonwealth University | Polypeptides that include conformation-constraining groups which flank a protein-protein interaction site |
| AU6770794A (en) * | 1993-04-23 | 1994-11-21 | Herbert J. Evans | Polypeptides that include conformation-constraining groups which flank a protein-protein interaction site |
| US5965698A (en) * | 1993-04-23 | 1999-10-12 | Virginia Commonwealth University | Polypeptides that include conformation-constraining groups which flank a protein--protein interaction site |
| US6258550B1 (en) | 1993-04-23 | 2001-07-10 | Virginia Commonwealth University | Polypeptides that include conformation-constraining groups which flank a protein-protein interaction site |
| US5928896A (en) * | 1993-04-23 | 1999-07-27 | Virginia Commonwealth University | Polypeptides that include conformation-constraining groups which flank a protein--protein interaction site |
| US6084066A (en) * | 1993-10-29 | 2000-07-04 | Virginia Commonwealth University | Polypetides that include conformation-constraining groups which flank a protein-protein interaction site |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005658A1 (fr) * | 1978-04-27 | 1979-11-28 | Laboratoire le Brun S.A. Société dite: | Nouveaux dérivés de peptides analogues des enképhalines, leur procédé de préparation et leur application thérapeutique |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1577115A (en) * | 1976-07-27 | 1980-10-22 | Reckitt & Colmann Prod Ltd | Container closure units |
| CH619686A5 (en) * | 1976-02-02 | 1980-10-15 | Sandoz Ag | Process for the preparation of novel peptides or peptide derivatives |
| US4259234A (en) * | 1976-09-27 | 1981-03-31 | Eli Lilly And Company | Analgesic compounds |
-
1979
- 1979-12-17 US US06/104,348 patent/US4283329A/en not_active Expired - Lifetime
-
1980
- 1980-12-11 DE DE8080304476T patent/DE3070184D1/de not_active Expired
- 1980-12-11 EP EP80304476A patent/EP0030848B1/en not_active Expired
- 1980-12-11 GB GB8039660A patent/GB2065132B/en not_active Expired
- 1980-12-12 IL IL61703A patent/IL61703A/xx unknown
- 1980-12-16 IE IE2642/80A patent/IE50883B1/en unknown
- 1980-12-16 BE BE1/10078A patent/BE886677A/fr not_active IP Right Cessation
- 1980-12-16 FR FR8026691A patent/FR2471970A1/fr active Granted
- 1980-12-16 JP JP17963980A patent/JPS5697257A/ja active Pending
- 1980-12-16 CH CH927480A patent/CH646686A5/fr not_active IP Right Cessation
- 1980-12-16 IT IT26672/80A patent/IT1141135B/it active
- 1980-12-16 KR KR1019800004794A patent/KR850000476B1/ko not_active Expired
- 1980-12-16 HU HU803011A patent/HU186375B/hu unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005658A1 (fr) * | 1978-04-27 | 1979-11-28 | Laboratoire le Brun S.A. Société dite: | Nouveaux dérivés de peptides analogues des enképhalines, leur procédé de préparation et leur application thérapeutique |
Also Published As
| Publication number | Publication date |
|---|---|
| KR830004218A (ko) | 1983-07-06 |
| KR850000476B1 (ko) | 1985-04-08 |
| EP0030848B1 (en) | 1985-02-13 |
| US4283329A (en) | 1981-08-11 |
| IE802642L (en) | 1981-06-17 |
| IL61703A0 (en) | 1981-01-30 |
| JPS5697257A (en) | 1981-08-05 |
| IT8026672A0 (it) | 1980-12-16 |
| GB2065132A (en) | 1981-06-24 |
| HU186375B (en) | 1985-07-29 |
| IT1141135B (it) | 1986-10-01 |
| IL61703A (en) | 1984-05-31 |
| FR2471970B1 (enExample) | 1984-11-16 |
| BE886677A (fr) | 1981-06-16 |
| GB2065132B (en) | 1983-06-02 |
| DE3070184D1 (en) | 1985-03-28 |
| IE50883B1 (en) | 1986-08-06 |
| EP0030848A3 (en) | 1981-12-16 |
| CH646686A5 (fr) | 1984-12-14 |
| EP0030848A2 (en) | 1981-06-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |