SE407215B - Forfarande for framstellning av peptider med psykofarmakologiska egenskaper - Google Patents
Forfarande for framstellning av peptider med psykofarmakologiska egenskaperInfo
- Publication number
- SE407215B SE407215B SE7307227A SE7307227A SE407215B SE 407215 B SE407215 B SE 407215B SE 7307227 A SE7307227 A SE 7307227A SE 7307227 A SE7307227 A SE 7307227A SE 407215 B SE407215 B SE 407215B
- Authority
- SE
- Sweden
- Prior art keywords
- phe
- met
- lys
- glu
- boc
- Prior art date
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims description 97
- 238000000034 method Methods 0.000 title claims description 18
- 102000004196 processed proteins & peptides Human genes 0.000 title description 31
- 230000001003 psychopharmacologic effect Effects 0.000 title description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 89
- 229910052681 coesite Inorganic materials 0.000 claims description 67
- 229910052906 cristobalite Inorganic materials 0.000 claims description 67
- 229910052682 stishovite Inorganic materials 0.000 claims description 67
- 229910052905 tridymite Inorganic materials 0.000 claims description 67
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 63
- 239000000377 silicon dioxide Substances 0.000 claims description 22
- 235000012239 silicon dioxide Nutrition 0.000 claims description 22
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 21
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 229910052751 metal Chemical class 0.000 claims description 16
- 239000002184 metal Chemical class 0.000 claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 15
- 150000001408 amides Chemical class 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
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- 238000002360 preparation method Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 238000005984 hydrogenation reaction Methods 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
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- 230000003647 oxidation Effects 0.000 claims description 4
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- 125000000729 N-terminal amino-acid group Chemical group 0.000 claims description 2
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- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 claims 1
- 108010033276 Peptide Fragments Proteins 0.000 claims 1
- 102000007079 Peptide Fragments Human genes 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 239000003797 essential amino acid Substances 0.000 claims 1
- 235000020776 essential amino acid Nutrition 0.000 claims 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 claims 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 174
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 90
- 239000000243 solution Substances 0.000 description 71
- 239000000203 mixture Substances 0.000 description 70
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 64
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
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- 229910000041 hydrogen chloride Inorganic materials 0.000 description 27
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- -1 D-amino acid radical Chemical class 0.000 description 19
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- 229940024606 amino acid Drugs 0.000 description 16
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- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06086—Dipeptides with the first amino acid being basic
- C07K5/06095—Arg-amino acid
-
- 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
-
- 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
- C07K14/695—Corticotropin [ACTH]
- C07K14/6955—Corticotropin [ACTH] with at least 1 amino acid in D-form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/081—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing O or S as heteroatoms, e.g. Cys, Ser
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
- C07K5/1013—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing O or S as heteroatoms, e.g. Cys, Ser
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1016—Tetrapeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Toxicology (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NLAANVRAGE7206941,A NL175988C (nl) | 1972-05-24 | 1972-05-24 | Werkwijze ter bereiding van een farmaceutisch preparaat met psychofarmacologische werking, dat een peptide of peptide-derivaat dat afgeleid is van een de aminozuren 4-10 omvattend, fragment van adrenocorticotroop hormoon als actief bestanddeel bevat, alsmede een werkwijze ter bereiding van deze peptiden. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE407215B true SE407215B (sv) | 1979-03-19 |
Family
ID=19816103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7307227A SE407215B (sv) | 1972-05-24 | 1973-05-23 | Forfarande for framstellning av peptider med psykofarmakologiska egenskaper |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3850904A (OSRAM) |
| JP (1) | JPS5747667B2 (OSRAM) |
| AU (1) | AU470908B2 (OSRAM) |
| BE (1) | BE799939A (OSRAM) |
| CA (1) | CA1030954A (OSRAM) |
| CH (1) | CH587229A5 (OSRAM) |
| DE (1) | DE2326033C2 (OSRAM) |
| FR (1) | FR2185412B1 (OSRAM) |
| GB (1) | GB1435384A (OSRAM) |
| HU (1) | HU169159B (OSRAM) |
| NL (1) | NL175988C (OSRAM) |
| SE (1) | SE407215B (OSRAM) |
| ZA (1) | ZA733211B (OSRAM) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4438029A (en) | 1978-01-19 | 1984-03-20 | Research Corporation | Synthetic peptides |
| US4356119A (en) * | 1978-09-28 | 1982-10-26 | Nordisk Insulinlaboratorium | Therapeutically active polypeptides or acid addition salts and a process for producing such compounds |
| NL8101724A (nl) * | 1981-04-08 | 1982-11-01 | Akzo Nv | Peptiden met zenuw-regenererende eigenschappen. |
| US4500713A (en) * | 1982-09-23 | 1985-02-19 | Usv Pharmaceutical Corporation | Therapeutic dipeptides |
| WO1986003746A1 (en) * | 1984-12-14 | 1986-07-03 | La Trobe University | Amino acid and peptide inhibitors of human leucocytic elastase |
| WO2011133348A1 (en) | 2010-04-21 | 2011-10-27 | Pharmacofore, Inc. | Compositions comprising enzyme-cleavable amphetamine prodrugs and inhibitors thereof |
| MX2023010506A (es) | 2021-03-09 | 2023-09-20 | Ensysce Biosciences Inc | Composiciones que comprenden profarmacos de escision enzimatica y nafamostat de liberacion controlada y metodos de uso de estos. |
| CA3230025A1 (en) | 2021-09-29 | 2023-04-06 | Lynn Kirkpatrick | Enzyme-cleavable methadone prodrugs and methods of use thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1302396A (fr) * | 1961-03-10 | 1962-08-31 | Ciba Geigy | Procédés de préparation de nouveaux heptapeptides de formule l-alpha-[mercaptoalcoyl (inférieur)]-alpha-amino-acétyl-l-glutaminyl-l-histidyl-l-phényl alanyl-l-alpha-[amino-alcoyl (inférieur)]-alpha-amino-acétyl-l-tryptophyl glycine |
| NL6509727A (OSRAM) * | 1965-07-28 | 1967-01-30 | ||
| GB1301738A (OSRAM) * | 1969-07-09 | 1973-01-04 |
-
1972
- 1972-05-24 NL NLAANVRAGE7206941,A patent/NL175988C/xx not_active IP Right Cessation
-
1973
- 1973-05-11 ZA ZA733211A patent/ZA733211B/xx unknown
- 1973-05-14 US US00359923A patent/US3850904A/en not_active Expired - Lifetime
- 1973-05-15 GB GB2298473A patent/GB1435384A/en not_active Expired
- 1973-05-16 AU AU55750/73A patent/AU470908B2/en not_active Expired
- 1973-05-21 CH CH719673A patent/CH587229A5/xx not_active IP Right Cessation
- 1973-05-22 DE DE2326033A patent/DE2326033C2/de not_active Expired
- 1973-05-22 CA CA171,907A patent/CA1030954A/en not_active Expired
- 1973-05-23 HU HUAO365A patent/HU169159B/hu unknown
- 1973-05-23 JP JP48057638A patent/JPS5747667B2/ja not_active Expired
- 1973-05-23 SE SE7307227A patent/SE407215B/sv unknown
- 1973-05-23 BE BE131443A patent/BE799939A/xx not_active IP Right Cessation
- 1973-05-24 FR FR7318960A patent/FR2185412B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2326033A1 (de) | 1973-12-20 |
| FR2185412A1 (OSRAM) | 1974-01-04 |
| FR2185412B1 (OSRAM) | 1976-12-03 |
| AU5575073A (en) | 1974-11-21 |
| CA1030954A (en) | 1978-05-09 |
| JPS5747667B2 (OSRAM) | 1982-10-12 |
| BE799939A (fr) | 1973-11-23 |
| NL175988B (nl) | 1984-09-03 |
| NL175988C (nl) | 1985-02-01 |
| GB1435384A (en) | 1976-05-12 |
| DE2326033C2 (de) | 1983-10-27 |
| AU470908B2 (en) | 1976-04-01 |
| NL7206941A (OSRAM) | 1973-11-27 |
| CH587229A5 (OSRAM) | 1977-04-29 |
| US3850904A (en) | 1974-11-26 |
| JPS4948666A (OSRAM) | 1974-05-11 |
| HU169159B (OSRAM) | 1976-10-28 |
| ZA733211B (en) | 1974-04-24 |
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