DD258609A5 - Aminosaeure-derivate, verfahren zu ihrer herstellung und verwendung - Google Patents
Aminosaeure-derivate, verfahren zu ihrer herstellung und verwendung Download PDFInfo
- Publication number
- DD258609A5 DD258609A5 DD86293752A DD29375286A DD258609A5 DD 258609 A5 DD258609 A5 DD 258609A5 DD 86293752 A DD86293752 A DD 86293752A DD 29375286 A DD29375286 A DD 29375286A DD 258609 A5 DD258609 A5 DD 258609A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- carboxylic acid
- tetrahydro
- general formula
- hydrogen
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 35
- 150000003862 amino acid derivatives Chemical class 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 230000008569 process Effects 0.000 claims abstract description 11
- 125000003277 amino group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
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- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 239000011593 sulfur Chemical group 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
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- -1 (S) -ethoxycarbonyl-3-phenylpropyl Chemical group 0.000 claims description 28
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- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical class OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- 125000001176 L-lysyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C([H])([H])C([H])([H])C(N([H])[H])([H])[H] 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- ORWYRWWVDCYOMK-HBZPZAIKSA-N angiotensin I Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 ORWYRWWVDCYOMK-HBZPZAIKSA-N 0.000 description 1
- 229950006323 angiotensin ii Drugs 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 230000003185 calcium uptake Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000003943 catecholamines Chemical class 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229940109275 cyclamate Drugs 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- ZLZXSWNRZFMSSS-UHFFFAOYSA-N ethyl 2-bromo-4-phenylbutanoate Chemical compound CCOC(=O)C(Br)CCC1=CC=CC=C1 ZLZXSWNRZFMSSS-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000003977 halocarboxylic acids Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 125000001288 lysyl group Chemical group 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SFODXSNBHRXQST-OGFXRTJISA-N methyl (6r)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-6-carboxylate;hydrochloride Chemical compound Cl.C1N[C@@H](C(=O)OC)CC2=C1C=CS2 SFODXSNBHRXQST-OGFXRTJISA-N 0.000 description 1
- SFODXSNBHRXQST-FJXQXJEOSA-N methyl (6s)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-6-carboxylate;hydrochloride Chemical compound Cl.C1N[C@H](C(=O)OC)CC2=C1C=CS2 SFODXSNBHRXQST-FJXQXJEOSA-N 0.000 description 1
- MGCDAKLEZAZUGN-UHFFFAOYSA-N methyl 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-4-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C1NCCC2=C1C=CS2 MGCDAKLEZAZUGN-UHFFFAOYSA-N 0.000 description 1
- SFODXSNBHRXQST-UHFFFAOYSA-N methyl 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-6-carboxylate;hydrochloride Chemical compound Cl.C1NC(C(=O)OC)CC2=C1C=CS2 SFODXSNBHRXQST-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
- 229960001597 nifedipine Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000008023 pharmaceutical filler Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 230000000894 saliuretic effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical group COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
- C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
-
- 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)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853529960 DE3529960A1 (de) | 1985-08-22 | 1985-08-22 | Aminosaeure-derivate, verfahren zu ihrer herstellung und verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD258609A5 true DD258609A5 (de) | 1988-07-27 |
Family
ID=6279053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86293752A DD258609A5 (de) | 1985-08-22 | 1986-08-20 | Aminosaeure-derivate, verfahren zu ihrer herstellung und verwendung |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5008273A (fr) |
| EP (1) | EP0213499A3 (fr) |
| JP (1) | JPS6245598A (fr) |
| KR (1) | KR870002145A (fr) |
| AU (1) | AU594969B2 (fr) |
| DD (1) | DD258609A5 (fr) |
| DE (1) | DE3529960A1 (fr) |
| DK (1) | DK398986A (fr) |
| ES (1) | ES2001875A6 (fr) |
| FI (1) | FI863358A (fr) |
| GR (1) | GR862183B (fr) |
| HU (1) | HU196434B (fr) |
| IL (1) | IL79792A (fr) |
| NO (1) | NO164982C (fr) |
| NZ (1) | NZ217310A (fr) |
| PL (1) | PL148493B1 (fr) |
| PT (1) | PT83239B (fr) |
| SU (1) | SU1544188A3 (fr) |
| YU (1) | YU146686A (fr) |
| ZA (1) | ZA866311B (fr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3801587A1 (de) * | 1988-01-21 | 1989-08-03 | Hoechst Ag | Neue aminosaeureglyceride, verfahren zu ihrer herstellung, sie enthaltende arzneimittel und deren verwendung |
| CA1340588C (fr) * | 1988-06-13 | 1999-06-08 | Balraj Krishan Handa | Derive d'aminoacides |
| US5162336A (en) * | 1990-06-21 | 1992-11-10 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Tetrahydro-pyrido-indoles as cholecystokinin and gastrin antagonists |
| US5688762A (en) * | 1995-09-06 | 1997-11-18 | Steiner; Zoltan W. | Method of treating hypertension using animal stomach mucosa extract and endogenous protease-inhibitor peptides |
| US5922839A (en) * | 1995-09-06 | 1999-07-13 | Steiner; Zoltan W. | Method of treating hypertension using a composition containing a dried animal stomach mucosa and endogenous protease-inhibitor peptides |
| WO2001004090A2 (fr) * | 1999-07-09 | 2001-01-18 | Ortho-Mcneil Pharmaceutical, Inc. | Tetrahydro-isoquinolines et tetrahydrothienopyridines neurotrophiques, compositions et procedes associes |
| CA2609812C (fr) * | 2005-05-27 | 2013-12-24 | University Of Cape Town | Inhibiteurs de l'enzyme de conversion d'angiotensine i (ace) |
| US7632796B2 (en) | 2005-10-28 | 2009-12-15 | Dynaloy, Llc | Dynamic multi-purpose composition for the removal of photoresists and method for its use |
| US8263539B2 (en) * | 2005-10-28 | 2012-09-11 | Dynaloy, Llc | Dynamic multi-purpose composition for the removal of photoresists and methods for its use |
| US9329486B2 (en) | 2005-10-28 | 2016-05-03 | Dynaloy, Llc | Dynamic multi-purpose composition for the removal of photoresists and method for its use |
| TWI450052B (zh) * | 2008-06-24 | 2014-08-21 | Dynaloy Llc | 用於後段製程操作有效之剝離溶液 |
| US8987181B2 (en) | 2011-11-08 | 2015-03-24 | Dynaloy, Llc | Photoresist and post etch residue cleaning solution |
| US9158202B2 (en) | 2012-11-21 | 2015-10-13 | Dynaloy, Llc | Process and composition for removing substances from substrates |
| US9029268B2 (en) | 2012-11-21 | 2015-05-12 | Dynaloy, Llc | Process for etching metals |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2487829A2 (fr) * | 1979-12-07 | 1982-02-05 | Science Union & Cie | Nouveaux imino acides substitues, leurs procedes de preparation et leur emploi comme inhibiteur d'enzyme |
| US4344949A (en) * | 1980-10-03 | 1982-08-17 | Warner-Lambert Company | Substituted acyl derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids |
| DE3174844D1 (en) * | 1980-10-23 | 1986-07-24 | Schering Corp | Carboxyalkyl dipeptides, processes for their production and pharmaceutical compositions containing them |
| DE3302125A1 (de) * | 1983-01-22 | 1984-07-26 | Boehringer Ingelheim KG, 6507 Ingelheim | Aminosaeure-derivate, verfahren zu ihrer herstellung und verwendung |
-
1985
- 1985-08-22 DE DE19853529960 patent/DE3529960A1/de not_active Withdrawn
-
1986
- 1986-08-04 SU SU864027899A patent/SU1544188A3/ru active
- 1986-08-14 EP EP86111239A patent/EP0213499A3/fr not_active Withdrawn
- 1986-08-20 DD DD86293752A patent/DD258609A5/de not_active IP Right Cessation
- 1986-08-20 PL PL1986261087A patent/PL148493B1/pl unknown
- 1986-08-20 FI FI863358A patent/FI863358A/fi not_active Application Discontinuation
- 1986-08-21 YU YU01466/86A patent/YU146686A/xx unknown
- 1986-08-21 ZA ZA866311A patent/ZA866311B/xx unknown
- 1986-08-21 DK DK398986A patent/DK398986A/da not_active Application Discontinuation
- 1986-08-21 IL IL79792A patent/IL79792A/xx unknown
- 1986-08-21 JP JP61194129A patent/JPS6245598A/ja active Pending
- 1986-08-21 NZ NZ217310A patent/NZ217310A/en unknown
- 1986-08-21 HU HU863645A patent/HU196434B/hu not_active IP Right Cessation
- 1986-08-21 NO NO863373A patent/NO164982C/no unknown
- 1986-08-21 ES ES8601245A patent/ES2001875A6/es not_active Expired
- 1986-08-21 AU AU61691/86A patent/AU594969B2/en not_active Ceased
- 1986-08-21 KR KR1019860006897A patent/KR870002145A/ko not_active Application Discontinuation
- 1986-08-22 GR GR862183A patent/GR862183B/el unknown
- 1986-08-22 PT PT83239A patent/PT83239B/pt not_active IP Right Cessation
-
1989
- 1989-09-06 US US07/403,628 patent/US5008273A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0213499A2 (fr) | 1987-03-11 |
| US5008273A (en) | 1991-04-16 |
| KR870002145A (ko) | 1987-03-30 |
| DK398986D0 (da) | 1986-08-21 |
| GR862183B (en) | 1986-12-23 |
| NO164982C (no) | 1990-12-05 |
| SU1544188A3 (ru) | 1990-02-15 |
| NO863373D0 (no) | 1986-08-21 |
| DK398986A (da) | 1987-02-23 |
| EP0213499A3 (fr) | 1989-08-23 |
| NO863373L (no) | 1987-02-23 |
| JPS6245598A (ja) | 1987-02-27 |
| ZA866311B (en) | 1988-04-27 |
| PL261087A1 (en) | 1988-04-14 |
| NO164982B (no) | 1990-08-27 |
| PT83239B (pt) | 1989-03-30 |
| DE3529960A1 (de) | 1987-03-05 |
| FI863358A (fi) | 1987-02-23 |
| PL148493B1 (en) | 1989-10-31 |
| IL79792A0 (en) | 1986-11-30 |
| HU196434B (en) | 1988-11-28 |
| NZ217310A (en) | 1990-01-29 |
| HUT42505A (en) | 1987-07-28 |
| AU594969B2 (en) | 1990-03-22 |
| ES2001875A6 (es) | 1988-07-01 |
| FI863358A0 (fi) | 1986-08-20 |
| IL79792A (en) | 1990-11-05 |
| AU6169186A (en) | 1987-02-26 |
| PT83239A (de) | 1986-09-01 |
| YU146686A (en) | 1988-02-29 |
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| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |