DE2308362A1 - Psychopharmakologisch aktive peptide und peptidderivate - Google Patents
Psychopharmakologisch aktive peptide und peptidderivateInfo
- Publication number
- DE2308362A1 DE2308362A1 DE19732308362 DE2308362A DE2308362A1 DE 2308362 A1 DE2308362 A1 DE 2308362A1 DE 19732308362 DE19732308362 DE 19732308362 DE 2308362 A DE2308362 A DE 2308362A DE 2308362 A1 DE2308362 A1 DE 2308362A1
- Authority
- DE
- Germany
- Prior art keywords
- met
- group
- phe
- glu
- peptide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims description 152
- 102000004196 processed proteins & peptides Human genes 0.000 title claims description 59
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 19
- 239000002184 metal Substances 0.000 claims description 19
- 150000003462 sulfoxides Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000320 amidine group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 3
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000001174 sulfone group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 59
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
- 239000000243 solution Substances 0.000 description 51
- 229910004298 SiO 2 Inorganic materials 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 239000000203 mixture Substances 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 31
- 125000006239 protecting group Chemical group 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 229960000583 acetic acid Drugs 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 150000001540 azides Chemical class 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 14
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 14
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- 238000003786 synthesis reaction Methods 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- 150000001408 amides Chemical class 0.000 description 13
- 150000001413 amino acids Chemical group 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- -1 heterocyclic carboxylic acid Chemical class 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 235000001014 amino acid Nutrition 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 8
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 7
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 7
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 7
- 125000000539 amino acid group Chemical group 0.000 description 7
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 230000001003 psychopharmacologic effect Effects 0.000 description 6
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 5
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- PVFCXMDXBIEMQG-JTQLQIEISA-N (2s)-2-(phenylmethoxycarbonylamino)pentanedioic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 PVFCXMDXBIEMQG-JTQLQIEISA-N 0.000 description 4
- FFEARJCKVFRZRR-SCSAIBSYSA-N D-methionine Chemical compound CSCC[C@@H](N)C(O)=O FFEARJCKVFRZRR-SCSAIBSYSA-N 0.000 description 4
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229940025084 amphetamine Drugs 0.000 description 4
- 230000008033 biological extinction Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 229960004452 methionine Drugs 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 4
- RKGFWMYLTBPZGL-YUMQZZPRSA-N (2s)-2-amino-1-[(2s)-2-amino-4-methylsulfanylbutanoyl]sulfinyl-4-methylsulfanylbutan-1-one Chemical compound CSCC[C@H](N)C(=O)S(=O)C(=O)[C@@H](N)CCSC RKGFWMYLTBPZGL-YUMQZZPRSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 108010016626 Dipeptides Proteins 0.000 description 3
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 3
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- 241001465754 Metazoa Species 0.000 description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
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- 108010005233 alanylglutamic acid Proteins 0.000 description 3
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- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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- SZXBQTSZISFIAO-ZETCQYMHSA-N (2s)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)OC(C)(C)C SZXBQTSZISFIAO-ZETCQYMHSA-N 0.000 description 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
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- RKGFWMYLTBPZGL-HTQZYQBOSA-N (2r)-2-amino-1-[(2r)-2-amino-4-methylsulfanylbutanoyl]sulfinyl-4-methylsulfanylbutan-1-one Chemical compound CSCC[C@@H](N)C(=O)S(=O)C(=O)[C@H](N)CCSC RKGFWMYLTBPZGL-HTQZYQBOSA-N 0.000 description 1
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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
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
-
- 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]
-
- 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
- C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
-
- 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
-
- 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
-
- 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)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Toxicology (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7202278A NL7202278A (enrdf_load_stackoverflow) | 1972-02-22 | 1972-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2308362A1 true DE2308362A1 (de) | 1973-09-06 |
Family
ID=19815436
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732308362 Pending DE2308362A1 (de) | 1972-02-22 | 1973-02-20 | Psychopharmakologisch aktive peptide und peptidderivate |
Country Status (12)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7607684A (nl) * | 1976-07-12 | 1978-01-16 | Akzo Nv | Werkwijze ter bereiding van nieuwe peptiden en peptide-derivaten en de toepassing hiervan. |
| US4623715A (en) | 1984-10-22 | 1986-11-18 | Hoechst Aktiengeselleschaft | Novel peptides which are active on the central nervous system and have an action on the cholinergic system |
| EP0204775A4 (en) * | 1984-12-14 | 1989-10-04 | Univ Trobe | INHIBITOR OF AMINO ACIDS AND PEPTIDES OF HUMAN LEUCOCYTIC ELASTASE. |
| US5462927A (en) * | 1985-04-30 | 1995-10-31 | The Administrators Of The Tulane Educational Fund | Peptides aiding nerve regeneration |
| JP2525798B2 (ja) * | 1987-03-12 | 1996-08-21 | 第一製薬株式会社 | ペプチド誘導体 |
| WO1993000922A1 (en) * | 1991-07-01 | 1993-01-21 | The Administrators Of The Tulane Educational Fund | Peptides aiding nerve regeneration |
| US7176279B2 (en) | 2000-06-28 | 2007-02-13 | Palatin Technologies, Inc. | Cyclic peptide compositions and methods for treatment of sexual dysfunction |
| US6579968B1 (en) * | 1999-06-29 | 2003-06-17 | Palatin Technologies, Inc. | Compositions and methods for treatment of sexual dysfunction |
| CA2419285C (en) * | 2000-08-25 | 2011-08-02 | Research Corporation Technologies, Inc. | New uses for amino acid anticonvulsants |
| IL159797A0 (en) * | 2001-07-11 | 2004-06-20 | Palatin Technologies Inc | Linear and cyclic melanocortin receptor-specific peptides |
| US6974187B2 (en) * | 2004-01-28 | 2005-12-13 | Tachi-S Co., Ltd. | Vehicle seat structure |
| AU2005231034B2 (en) * | 2004-04-08 | 2010-04-08 | Telsar Pharma Inc. | Compound WS727713 |
| KR101176758B1 (ko) * | 2004-04-08 | 2012-08-23 | 아스테라스 세이야쿠 가부시키가이샤 | 화합물 ｗｓ727713 |
| EP2560486B1 (en) * | 2010-04-21 | 2018-11-21 | Signature Therapeutics, Inc. | Compositions comprising enzyme-cleavable amphetamine prodrugs and inhibitors thereof |
| US11590209B2 (en) | 2020-01-21 | 2023-02-28 | Palatin Technologies, Inc. | Use of bremelanotide in patients with controlled hypertension |
| EP4237007A1 (en) * | 2020-11-18 | 2023-09-06 | Mind Medicine, Inc. | Mdma prodrugs to assist psychotherapy |
| WO2023055830A1 (en) | 2021-09-29 | 2023-04-06 | Ensysce Biosciences, Inc. | Enzyme-cleavable methadone prodrugs and methods of use thereof |
Family Cites Families (4)
| 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 |
| NL278010A (enrdf_load_stackoverflow) * | 1961-05-04 | 1900-01-01 | ||
| NL6509727A (enrdf_load_stackoverflow) * | 1965-07-28 | 1967-01-30 | ||
| GB1230472A (enrdf_load_stackoverflow) * | 1967-07-10 | 1971-05-05 |
-
0
- BE BE795788D patent/BE795788A/xx unknown
-
1972
- 1972-02-22 NL NL7202278A patent/NL7202278A/xx unknown
-
1973
- 1973-02-06 ZA ZA730839A patent/ZA73839B/xx unknown
- 1973-02-08 AU AU51979/73A patent/AU471298B2/en not_active Expired
- 1973-02-08 GB GB621973A patent/GB1416271A/en not_active Expired
- 1973-02-12 US US00331945A patent/US3853836A/en not_active Expired - Lifetime
- 1973-02-20 HU HUAO351A patent/HU168890B/hu unknown
- 1973-02-20 DE DE19732308362 patent/DE2308362A1/de active Pending
- 1973-02-21 CH CH245873A patent/CH585192A5/xx not_active IP Right Cessation
- 1973-02-21 CA CA164,274A patent/CA1030953A/en not_active Expired
- 1973-02-21 JP JP48021120A patent/JPS4896586A/ja active Pending
- 1973-02-22 FR FR7306338A patent/FR2181759B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4896586A (enrdf_load_stackoverflow) | 1973-12-10 |
| US3853836A (en) | 1974-12-10 |
| AU471298B2 (en) | 1976-04-15 |
| CA1030953A (en) | 1978-05-09 |
| FR2181759B1 (enrdf_load_stackoverflow) | 1976-09-03 |
| HU168890B (enrdf_load_stackoverflow) | 1976-08-28 |
| ZA73839B (en) | 1973-11-28 |
| CH585192A5 (enrdf_load_stackoverflow) | 1977-02-28 |
| FR2181759A1 (enrdf_load_stackoverflow) | 1973-12-07 |
| BE795788A (nl) | 1973-08-22 |
| AU5197973A (en) | 1974-08-08 |
| NL7202278A (enrdf_load_stackoverflow) | 1973-08-24 |
| GB1416271A (en) | 1975-12-03 |
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