DE2343037A1 - MEDICINAL PRODUCTS WITH ANTIDEPRESSIVE EFFECT - Google Patents
MEDICINAL PRODUCTS WITH ANTIDEPRESSIVE EFFECTInfo
- Publication number
- DE2343037A1 DE2343037A1 DE19732343037 DE2343037A DE2343037A1 DE 2343037 A1 DE2343037 A1 DE 2343037A1 DE 19732343037 DE19732343037 DE 19732343037 DE 2343037 A DE2343037 A DE 2343037A DE 2343037 A1 DE2343037 A1 DE 2343037A1
- Authority
- DE
- Germany
- Prior art keywords
- prolinamide
- effect
- pyroglutamyl
- medicinal products
- trh
- 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
- 230000001430 anti-depressive effect Effects 0.000 title claims description 7
- 229940126601 medicinal product Drugs 0.000 title 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 4
- -1 L-pyroglutamyl Chemical group 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 3
- TVLAAZVYMRMYSE-VIFPVBQESA-N (2s)-2-amino-3-(1h-imidazol-5-yl)-1-pyrrolidin-1-ylpropan-1-one Chemical compound C([C@H](N)C(=O)N1CCCC1)C1=CNC=N1 TVLAAZVYMRMYSE-VIFPVBQESA-N 0.000 claims description 2
- LNCFUHAPNTYMJB-IUCAKERBSA-N His-Pro Chemical compound C([C@H](N)C(=O)N1[C@@H](CCC1)C(O)=O)C1=CN=CN1 LNCFUHAPNTYMJB-IUCAKERBSA-N 0.000 claims description 2
- 229960002885 histidine Drugs 0.000 claims description 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 2
- HAZDSEVQCDGJTA-RYUDHWBXSA-N (2s)-1-[(2s)-2-amino-3-phenylpropanoyl]pyrrolidine-2-carboxamide Chemical compound C([C@H](N)C(=O)N1[C@@H](CCC1)C(N)=O)C1=CC=CC=C1 HAZDSEVQCDGJTA-RYUDHWBXSA-N 0.000 claims 1
- XNSAINXGIQZQOO-SRVKXCTJSA-N protirelin Chemical compound NC(=O)[C@@H]1CCCN1C(=O)[C@@H](NC(=O)[C@H]1NC(=O)CC1)CC1=CN=CN1 XNSAINXGIQZQOO-SRVKXCTJSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002775 capsule Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 229920001592 potato starch Polymers 0.000 description 3
- 230000003578 releasing effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 102000003946 Prolactin Human genes 0.000 description 2
- 108010057464 Prolactin Proteins 0.000 description 2
- 208000028017 Psychotic disease Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229940097325 prolactin Drugs 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical group OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 1
- 101000904177 Clupea pallasii Gonadoliberin-1 Proteins 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 239000000579 Gonadotropin-Releasing Hormone Substances 0.000 description 1
- 206010020850 Hyperthyroidism Diseases 0.000 description 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 101000857870 Squalus acanthias Gonadoliberin Proteins 0.000 description 1
- 102000011923 Thyrotropin Human genes 0.000 description 1
- 108010061174 Thyrotropin Proteins 0.000 description 1
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- XLXSAKCOAKORKW-AQJXLSMYSA-N gonadorelin Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 XLXSAKCOAKORKW-AQJXLSMYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 208000015238 neurotic disease Diseases 0.000 description 1
- XFWCSGJOVUQCME-YUMQZZPRSA-N pEH Chemical compound C([C@@H](C(=O)O)NC(=O)[C@H]1NC(=O)CC1)C1=CNC=N1 XFWCSGJOVUQCME-YUMQZZPRSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001646 thyrotropic effect Effects 0.000 description 1
- 229960000874 thyrotropin Drugs 0.000 description 1
- 230000001748 thyrotropin Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06173—Dipeptides with the first amino acid being heterocyclic and Glp-amino acid; Derivatives thereof
-
- 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
- C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
- C07K5/0825—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp and Glp-amino acid; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
FARBWERKE HOECHST AKTIENGESELLSCHAFTFARBWERKE HOECHST AKTIENGESELLSCHAFT
vormals Meister Lucius & Brüning 0*5/ Q Π Q Π formerly Master Lucius & Brüning 0 * 5 / Q Π Q Π
Aktenzeichen: HOE 73/F 253File number: HOE 73 / F 253
Dr.HG/kaDr.HG / ka
Datum: 23. August 1973Date: August 23, 1973
Aus der US-Patentschrift 3.737.5^9 ist bereits bekannt, daß das Tripeptidamid L-Pyroglutamyl-L-histidyl-L-prolinamid (TRH) nicht nur die Freisetzung von Thyreotropem Hormon bewirkt, sondern auch antidepressive Wirkung besitzt. TRH hat bei seiner Anwendung als Antidepressivum jedoch den Nachteil der stark thyreotropin-ausschüttenden Wirkung.From US Pat. No. 3,737.5 ^ 9 it is already known that the tripeptide amide L-pyroglutamyl-L-histidyl-L-prolinamide (TRH) not only causes the release of thyrotropic hormone, but also has an antidepressant effect. TRH has at his Use as an antidepressant, however, has the disadvantage of the strong thyrotropin-releasing effect.
Überraschenderweise wurde nun gefunden, daß bei Verbindungen mit geringer Abänderung des TRH-Moleküls die antidepressive Wirkung nahezu unverändert bleibt obwohl die TRH-Wirkung gering oder auch nicht mehr vorhanden ist.Surprisingly, it has now been found that in compounds with little modification of the TRH molecule, the antidepressant Effect remains almost unchanged although the TRH effect is low or no longer present.
Gegenstand der Erfindung sind Arzneimittel gegen neurotische und psychotische Erkrankungen, insbesondere von Depressionen, dadurch gekennzeichnet, daß sie L-Pyroglutamylpeptide der allgemeinen Formel IThe invention relates to drugs against neurotic and psychotic diseases, in particular depression, characterized in that they contain L-pyroglutamyl peptides of the general Formula I.
L Giu-L Giu-
GIu-X (i)GIu-X (i)
wobei X den L-Histidin-, den L-Histidin-pyrrolidid-, den L-Histidyl-L-prolin-, den L-Histidyl-L-trypthophanamid-, den L-Phenylalanyl-L-prolinamid-, den L-Methionyl-L-prolinamid- oder den L-Lysyl-L-prolinamid-rest bedeutet, enthalten.where X denotes the L-histidine, the L-histidine pyrrolidide, the L-histidyl-L-proline, the L-histidyl-L-trypthophanamid-, the L-phenylalanyl-L-prolinamid-, the L-methionyl-L-prolinamid- or denotes the L-lysyl-L-prolinamide residue.
509810/0935509810/0935
Die Stoffe der allgemeinen Formel I sind bekannt und können in an sich bekannter Weise nach den Methoden der Peptidchemie hergestellt werden.The substances of the general formula I are known and can be prepared in a manner known per se by the methods of peptide chemistry will.
L-Pyroglutamyl-L-histidin, von dem noch keine biologische Wirkung bekannt war, wurde als Zwischenprodukt zur Synthese von LH-RH synthetisiert (Chem. Ber. 105, 2872 (1972)). L-Pyroglutamyl-L-histidin-pyrrolidid (Chem. Ber. J_0J5, 2872 (1972), L-Pyroglutamyl-L-histidyl-L-prolin (HeIv. Chem. Acta £3, 63 (197O)), L-Pyroglutamyl-L-phenylalanyl-L-prolinamid(«T.Med. Chem. _1_5_, 219 (1972)), L-Pyroglutamyl-L-methionyl-L-prolinamid (j. Med. Chem. _P5, 479 (1972)) und L-Pyroglutamyl-L-lysyl-L-prolinamid (HeIv. chim. Acta %k_, 135 (1971) haben eine abgeschwächte TRH-Wirkung. Diese Substanzen zeigen auch noch schwach prolactinausschüttende Wirkung.L-pyroglutamyl-L-histidine, of which no biological activity was known, was synthesized as an intermediate for the synthesis of LH-RH (Chem. Ber. 105 , 2872 (1972)). L-pyroglutamyl-L-histidine-pyrrolidide (Chem. Ber. J_0J5, 2872 (1972), L-pyroglutamyl-L-histidyl-L-proline (HeIv. Chem. Acta £ 3, 63 (197O)), L-pyroglutamyl -L-phenylalanyl-L-prolinamide ("T. Med. Chem. _1_5_, 219 (1972)), L-pyroglutamyl-L-methionyl-L-prolinamide (j. Med. Chem. _P5, 479 (1972)) and L-pyroglutamyl-L-lysyl-L-prolinamide (HeIv. Chim. Acta % k_, 135 (1971) have a weakened TRH effect. These substances also show a weak prolactin-releasing effect.
Alle Verbindungen der Formel I zeigen in dem Dopa-Potenzierungstest (Everett, Fed. Proc. _2J3, 198 (1964)) eine dem TRH vergleichbare antidepress^e Wirkung:All compounds of formula I show in the dopa potentiation test (Everett, Fed. Proc. _2J3, 198 (1964)) one comparable to the TRH antidepressant effect:
Prozentsatz der Übererreung in Abhängigkeit von der Dosis (mg/kg) Percentage of overexcitation depending on the dose (mg / kg)
0.50.5
TRHTRH
-His-OH LGIu-His-pyrrolidid LGlu-His-Pro~0H LGlu-His-Trp-NH ι—ι <*■ -His-OH LGIu-His-pyrrolidide LGlu-His-Pro ~ 0H LGlu-His-Trp-NH ι-ι <* ■
I-Glu-Phe-Pro-NH2 I-Glu-Phe-Pro-NH 2
LG.lu-Met-Pro-NHQ '-GIu-Ly s-Pro-NH„ KontrolleLG.lu-Met-Pro-NH Q '-GIu-Ly s-Pro-NH "Control
509810/0935509810/0935
Bei Anwendung dieser Substanzen zur Behandlung von ηeurotischen und psychotischen Erkrankungen, insbesondere von Depressionen ist im Gegensatz zu TRH bei den erfindungsgemäßen Produkten keine Hyperthyreose zu befürchten. Auch die prolactinausschüttende Wirkung von TRII (BeIg. Patent No. 790 851) ist beiden erfindungsgemäßen Verbindungen abgeschwächt.When using these substances for the treatment of ηeurotic and psychotic illnesses, especially depression, is in contrast to TRH in the products according to the invention not to worry about hyperthyroidism. Also the prolactin-releasing one Effect of TRII (BeIg. Patent No. 790 851) is both compounds according to the invention weakened.
Die erfindungsgemäßen Arzneipräparate können z. B. in Form einer Tablette oder Pille, als Kapsel oder Tropfen oral verabfolgt werden oder gelbst in einer physiologischen Kochsalzlösung intravenös oder intramuskulär appliziert werden. In geeigneter Zubereitung können sie auch intranasal verabreicht werden. Die oral zu verabreichende Dosis bewegt sich in Abhängigkeit der jeweiligen Erkrankung zwischen 10 und 1000 mg. Intravenös appliziert genügen 0.1 bis 10 mg Wirksubstanz.The medicinal preparations according to the invention can, for. B. in shape a tablet or pill, as a capsule or drop, or yellow in a physiological saline solution administered intravenously or intramuscularly. In a suitable preparation they can also be administered intranasally will. The dose to be administered orally ranges between 10 and 1000 mg, depending on the particular disease. Intravenously applied, 0.1 to 10 mg of active substance are sufficient.
Abkürzung:Abbreviation:
I—GIu = PyroglutaminsäureI-GIu = pyroglutamic acid
509810/0935509810/0935
Beispiel example Λ Λ ;;
500 g eines Wirkstoffs werden mit 282 g Kartoffelstärke und 56Ο g Lactose vermischt, die Mischung mit einer alkoholischen Lösung von 8 g Gelatine befeuchtet und granuliert. Nach dein Trocknen mischt man 60 g Kartoffelstärke, 10g Magnesiumstearat, 20 g hochdisperses Siliciumoxid und 60 g Talk zu und presst die Mischung zu 100OO Tabletten von je I50 mg Gewicht. Jede Tablette enthält 50 mg Wirkstoff.500 g of an active ingredient are mixed with 282 g of potato starch and 56Ο g of lactose mixed, the mixture with an alcoholic Solution of 8 g of gelatin moistened and granulated. After drying, mix 60 g potato starch, 10 g magnesium stearate, 20 g of highly disperse silicon oxide and 60 g of talc are added and the mixture is pressed into 10000 tablets, each weighing 150 mg. Each tablet contains 50 mg of active ingredient.
50 g Wirkstoff werden mit k96 g Lactose vermischt. Man befeuchtet die Mischung gleichmäßig mit einer wässrigen Mischung von k g Gelatine und granuliert. Das getrocknete Granulat, vermischt mit 20 g Kartoffelstärke und 30 g Talk, wird gleichmäßig in 2000 Hartgelatine-Kapseln der Größe 1 gefüllt. Jede Kapsel enthält 25 mg Wirkstoff.50 g of active ingredient are mixed with k96 g of lactose. The mixture is moistened uniformly with an aqueous mixture of k g of gelatin and granulated. The dried granules, mixed with 20 g of potato starch and 30 g of talc, are evenly filled into 2000 size 1 hard gelatine capsules. Each capsule contains 25 mg of active ingredient.
9 Liter destilliertes Wasser werden zum Sieden erhitzt und darin 20 g p-Hydroxybenzoesäuremethylester gelöst. Mein kühlt auf ca. 30°C ab, gibt 89.58 g Na2HPO^, 35·^ g Citronensäure, 9 liters of distilled water are heated to the boil and 20 g of methyl p-hydroxybenzoate are dissolved in it. Mine cools down to about 30 ° C, gives 89.58 g Na 2 HPO ^, 35 ^ g citric acid,
10 g Natx-iumchlorid und 25Ο g Mannit zu und löst dann darin 50 g Wirksubstanz auf. Man füllt mit destilliertem Wasser auf 10 1 auf und filtriert die Lösung. Diese Flüssigkeit kann als Nasentropfen Verwendung finden.10 g of sodium chloride and 25Ο g of mannitol and then dissolve in it 50 g of active ingredient. It is filled with distilled water to 10 1 and filtered the solution. This liquid can be used as a nose drop.
509810/0935509810/0935
Claims (1)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732343037 DE2343037A1 (en) | 1973-08-25 | 1973-08-25 | MEDICINAL PRODUCTS WITH ANTIDEPRESSIVE EFFECT |
| NL7411104A NL7411104A (en) | 1973-08-25 | 1974-08-20 | MEDICINAL PRODUCT WITH ANTI-PRESSIVE ACTIVITY. |
| AU72592/74A AU7259274A (en) | 1973-08-25 | 1974-08-22 | Medicaments |
| LU70784A LU70784A1 (en) | 1973-08-25 | 1974-08-23 | |
| ZA00745423A ZA745423B (en) | 1973-08-25 | 1974-08-23 | Medicaments having an antidepressive effect |
| DK452374A DK452374A (en) | 1973-08-25 | 1974-08-23 | |
| BE147919A BE819200A (en) | 1973-08-25 | 1974-08-26 | MEDICINAL PRODUCT HAVING AN ANTI-DEPRESSIVE EFFECT |
| FR7429137A FR2241307A1 (en) | 1973-08-25 | 1974-08-26 | Antidepressant peptide cpds. - contg. pyroglutamyl as the N-terminal amino-acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732343037 DE2343037A1 (en) | 1973-08-25 | 1973-08-25 | MEDICINAL PRODUCTS WITH ANTIDEPRESSIVE EFFECT |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2343037A1 true DE2343037A1 (en) | 1975-03-06 |
Family
ID=5890743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732343037 Pending DE2343037A1 (en) | 1973-08-25 | 1973-08-25 | MEDICINAL PRODUCTS WITH ANTIDEPRESSIVE EFFECT |
Country Status (8)
| Country | Link |
|---|---|
| AU (1) | AU7259274A (en) |
| BE (1) | BE819200A (en) |
| DE (1) | DE2343037A1 (en) |
| DK (1) | DK452374A (en) |
| FR (1) | FR2241307A1 (en) |
| LU (1) | LU70784A1 (en) |
| NL (1) | NL7411104A (en) |
| ZA (1) | ZA745423B (en) |
Cited By (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3024256A1 (en) * | 1979-06-28 | 1981-01-08 | Richter Gedeon Vegyeszet | PEPTIDAMIDES, METHOD FOR THE PRODUCTION THEREOF, AND MEDICINAL PRODUCTS CONTAINING THE SAME |
| US5766633A (en) | 1993-04-22 | 1998-06-16 | Emisphere Technologies, Inc. | Oral drug delivery compositions and methods |
| US5773647A (en) * | 1997-02-07 | 1998-06-30 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5776888A (en) * | 1997-02-07 | 1998-07-07 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5804688A (en) | 1997-02-07 | 1998-09-08 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5811127A (en) | 1992-06-15 | 1998-09-22 | Emisphere Technologies, Inc. | Desferrioxamine oral delivery system |
| US5824345A (en) | 1995-06-07 | 1998-10-20 | Emisphere Technologies, Inc. | Fragrances and flavorants |
| US5863944A (en) | 1997-04-30 | 1999-01-26 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5866536A (en) | 1995-03-31 | 1999-02-02 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5879681A (en) | 1997-02-07 | 1999-03-09 | Emisphere Technolgies Inc. | Compounds and compositions for delivering active agents |
| US5935601A (en) * | 1994-04-22 | 1999-08-10 | Emisphere Technologies, Inc. | Modified amino acids for drug delivery |
| US5939381A (en) | 1997-02-07 | 1999-08-17 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5955503A (en) | 1993-04-22 | 1999-09-21 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5962710A (en) | 1997-05-09 | 1999-10-05 | Emisphere Technologies, Inc. | Method of preparing salicyloylamino acids |
| US5972387A (en) | 1992-12-21 | 1999-10-26 | Emisphere Technologies, Inc. | Modified hydrolyzed vegetable protein microspheres and methods for preparation and use thereof |
| US5990166A (en) | 1997-02-07 | 1999-11-23 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US6051258A (en) | 1995-06-07 | 2000-04-18 | Emisphere Technologies, Inc. | Proteinoid emulsions and methods for preparation and use thereof |
| US6051561A (en) * | 1997-02-07 | 2000-04-18 | Emisphere Technologies Inc. | Compounds and compositions for delivering active agents |
| US6060513A (en) | 1997-02-07 | 2000-05-09 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US6071510A (en) | 1995-03-31 | 2000-06-06 | Emisphere Technologies, Inc. | Modified amino acids and compositions comprising the same for delivering active agents |
| US6071538A (en) | 1992-06-15 | 2000-06-06 | Emisphere Technologies, Inc. | Oral delivery composition comprising supramolecular complex |
| US6084112A (en) | 1995-09-11 | 2000-07-04 | Emisphere Technologies, Inc. | Method for preparing ω-aminoalkanoic acid derivatives from cycloalkanones |
| US6100285A (en) | 1995-06-07 | 2000-08-08 | Emisphere Technologies, Inc. | Method of solubilizing itraconazole |
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| US6242495B1 (en) | 1997-02-07 | 2001-06-05 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US6346242B1 (en) | 1995-03-31 | 2002-02-12 | Emishpere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US6358504B1 (en) | 1997-02-07 | 2002-03-19 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US6375983B1 (en) | 1996-06-14 | 2002-04-23 | Emisphere Technologies, Inc. | Microencapsulated fragrances and method for preparation |
| US6413550B1 (en) | 1992-06-15 | 2002-07-02 | Emisphere Technologies, Inc. | Proteinoid carriers and methods for preparation and use thereof |
| EP1893192A4 (en) * | 2005-06-08 | 2010-03-31 | Univ North Carolina | METHODS FOR FACILITATING NEURAL CELL SURVIVAL USING NON-PEPTIDE AND PEPTIDE NEUROTROPHIN MIMETICS OF THE BDNF TYPE |
| US9828330B2 (en) | 2013-03-15 | 2017-11-28 | Pharmatrophix, Inc. | Non-peptide BDNF neurotrophin mimetics |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU4125578A (en) * | 1977-11-09 | 1979-05-17 | Merck & Co Inc | Tripeptides |
| HU184481B (en) * | 1981-10-02 | 1984-08-28 | Richter Gedeon Vegyeszet | Process for producing tripeptides for diminishing appetite |
| IT1186733B (en) * | 1985-06-05 | 1987-12-16 | Eniricerche Spa | TRIPEPTIDIC COMPOUNDS WITH HYPOTHENSIVE ACTION |
-
1973
- 1973-08-25 DE DE19732343037 patent/DE2343037A1/en active Pending
-
1974
- 1974-08-20 NL NL7411104A patent/NL7411104A/en unknown
- 1974-08-22 AU AU72592/74A patent/AU7259274A/en not_active Expired
- 1974-08-23 LU LU70784A patent/LU70784A1/xx unknown
- 1974-08-23 DK DK452374A patent/DK452374A/da unknown
- 1974-08-23 ZA ZA00745423A patent/ZA745423B/en unknown
- 1974-08-26 FR FR7429137A patent/FR2241307A1/en active Granted
- 1974-08-26 BE BE147919A patent/BE819200A/en unknown
Cited By (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3024256A1 (en) * | 1979-06-28 | 1981-01-08 | Richter Gedeon Vegyeszet | PEPTIDAMIDES, METHOD FOR THE PRODUCTION THEREOF, AND MEDICINAL PRODUCTS CONTAINING THE SAME |
| US6348207B1 (en) | 1992-06-15 | 2002-02-19 | Emisiphere Technologies, Inc. | Orally deliverable supramolecular complex |
| US6245359B1 (en) | 1992-06-15 | 2001-06-12 | Emisphere Technologies, Inc. | Active agent transport systems |
| US6099856A (en) | 1992-06-15 | 2000-08-08 | Emisphere Technologies, Inc. | Active agent transport systems |
| US6071538A (en) | 1992-06-15 | 2000-06-06 | Emisphere Technologies, Inc. | Oral delivery composition comprising supramolecular complex |
| US5811127A (en) | 1992-06-15 | 1998-09-22 | Emisphere Technologies, Inc. | Desferrioxamine oral delivery system |
| US6413550B1 (en) | 1992-06-15 | 2002-07-02 | Emisphere Technologies, Inc. | Proteinoid carriers and methods for preparation and use thereof |
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| US5972387A (en) | 1992-12-21 | 1999-10-26 | Emisphere Technologies, Inc. | Modified hydrolyzed vegetable protein microspheres and methods for preparation and use thereof |
| US5955503A (en) | 1993-04-22 | 1999-09-21 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
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| US6051258A (en) | 1995-06-07 | 2000-04-18 | Emisphere Technologies, Inc. | Proteinoid emulsions and methods for preparation and use thereof |
| US6461545B1 (en) | 1995-06-07 | 2002-10-08 | Emisphere Technologies, Inc. | Method of solubilizing and encapsulating itraconazole |
| US5824345A (en) | 1995-06-07 | 1998-10-20 | Emisphere Technologies, Inc. | Fragrances and flavorants |
| US6084112A (en) | 1995-09-11 | 2000-07-04 | Emisphere Technologies, Inc. | Method for preparing ω-aminoalkanoic acid derivatives from cycloalkanones |
| US6375983B1 (en) | 1996-06-14 | 2002-04-23 | Emisphere Technologies, Inc. | Microencapsulated fragrances and method for preparation |
| US6358504B1 (en) | 1997-02-07 | 2002-03-19 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5773647A (en) * | 1997-02-07 | 1998-06-30 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US8686154B2 (en) | 1997-02-07 | 2014-04-01 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
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| US5939381A (en) | 1997-02-07 | 1999-08-17 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
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| US7553872B2 (en) | 1997-02-07 | 2009-06-30 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US6060513A (en) | 1997-02-07 | 2000-05-09 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5776888A (en) * | 1997-02-07 | 1998-07-07 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5990166A (en) | 1997-02-07 | 1999-11-23 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
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| US5863944A (en) | 1997-04-30 | 1999-01-26 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5962710A (en) | 1997-05-09 | 1999-10-05 | Emisphere Technologies, Inc. | Method of preparing salicyloylamino acids |
| EP1893192A4 (en) * | 2005-06-08 | 2010-03-31 | Univ North Carolina | METHODS FOR FACILITATING NEURAL CELL SURVIVAL USING NON-PEPTIDE AND PEPTIDE NEUROTROPHIN MIMETICS OF THE BDNF TYPE |
| US8686045B2 (en) | 2005-06-08 | 2014-04-01 | The University Of North Carolina At Chapel Hill | Methods of facilitating neural cell survival using non-peptide and peptide BDNF neurotrophin mimetics |
| US9604907B2 (en) | 2005-06-08 | 2017-03-28 | The University Of North Carolina At Chapel Hill | Methods of facilitating neural cell survival using non-peptide and peptide BDNF neurotrophin mimetics |
| US9828330B2 (en) | 2013-03-15 | 2017-11-28 | Pharmatrophix, Inc. | Non-peptide BDNF neurotrophin mimetics |
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Also Published As
| Publication number | Publication date |
|---|---|
| AU7259274A (en) | 1976-02-26 |
| DK452374A (en) | 1975-04-28 |
| ZA745423B (en) | 1975-08-27 |
| LU70784A1 (en) | 1976-08-19 |
| FR2241307A1 (en) | 1975-03-21 |
| BE819200A (en) | 1975-02-26 |
| FR2241307B1 (en) | 1978-07-21 |
| NL7411104A (en) | 1975-02-27 |
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