CH617183A5 - - Google Patents

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Info

Publication number: CH617183A5
Authority: CH; Switzerland
Prior art keywords: group; compounds; general formula; compound; formula
Prior art date: 1974-04-29

Application number

CH539075A

Other languages

German (de)

English (en)

Inventor

Laszlo Feuer

Arpad Furka

Ferenc Sebestyen

Jolan Hercsel-Szepespataky

Erzsebet Bendefy-Dobay

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

Priority date (The priority date 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 date listed.)

1974-04-29

Filing date

1975-04-28

Publication date

1980-05-14

1974-04-29 Priority claimed from HU74FE00000928A external-priority patent/HU171576B/hu

1975-03-26 Priority claimed from HU74CI1558A external-priority patent/HU174114B/hu

1975-04-28 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1980-05-14 Publication of CH617183A5 publication Critical patent/CH617183A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 58
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 57
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 55
XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 48
229960003080 taurine Drugs 0.000 claims description 43
239000000203 mixture Substances 0.000 claims description 34
238000000034 method Methods 0.000 claims description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
238000002360 preparation method Methods 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 17
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 12
229960000583 acetic acid Drugs 0.000 claims description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
229910019142 PO4 Inorganic materials 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 10
239000012362 glacial acetic acid Substances 0.000 claims description 10
239000010452 phosphate Substances 0.000 claims description 10
125000006239 protecting group Chemical group 0.000 claims description 10
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 9
-1 suc-cinimidoxy Chemical group 0.000 claims description 7
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 6
SNKZJIOFVMKAOJ-UHFFFAOYSA-N 3-Aminopropanesulfonate Chemical compound NCCCS(O)(=O)=O SNKZJIOFVMKAOJ-UHFFFAOYSA-N 0.000 claims description 5
229940099500 cystamine Drugs 0.000 claims description 5
230000008569 process Effects 0.000 claims description 5
SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
150000007530 organic bases Chemical class 0.000 claims description 4
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
125000003545 alkoxy group Chemical group 0.000 claims 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical group [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 3
125000002252 acyl group Chemical group 0.000 claims 3
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 3
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 3
125000000000 cycloalkoxy group Chemical group 0.000 claims 3
229910052736 halogen Inorganic materials 0.000 claims 3
125000005843 halogen group Chemical group 0.000 claims 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
239000003513 alkali Substances 0.000 claims 2
229910001854 alkali hydroxide Inorganic materials 0.000 claims 2
150000001540 azides Chemical class 0.000 claims 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
238000007127 saponification reaction Methods 0.000 claims 2
ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims 1
ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 claims 1
FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 claims 1
ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 claims 1
229910000272 alkali metal oxide Inorganic materials 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 1
150000008064 anhydrides Chemical class 0.000 claims 1
125000003710 aryl alkyl group Chemical group 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 claims 1
FIZJLXAYKPNXIJ-UHFFFAOYSA-N phenylmethoxycarbonylcarbamic acid Chemical compound OC(=O)NC(=O)OCC1=CC=CC=C1 FIZJLXAYKPNXIJ-UHFFFAOYSA-N 0.000 claims 1
125000003107 substituted aryl group Chemical group 0.000 claims 1
230000009885 systemic effect Effects 0.000 claims 1
239000000243 solution Substances 0.000 description 58
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
239000000126 substance Substances 0.000 description 27
230000000694 effects Effects 0.000 description 25
239000000047 product Substances 0.000 description 25
XVOYSCVBGLVSOL-UHFFFAOYSA-N cysteic acid Chemical compound OC(=O)C(N)CS(O)(=O)=O XVOYSCVBGLVSOL-UHFFFAOYSA-N 0.000 description 22
238000001962 electrophoresis Methods 0.000 description 20
235000019441 ethanol Nutrition 0.000 description 20
239000004480 active ingredient Substances 0.000 description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
239000011541 reaction mixture Substances 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
230000001965 increasing effect Effects 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
229940086542 triethylamine Drugs 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 12
238000003756 stirring Methods 0.000 description 12
229960002989 glutamic acid Drugs 0.000 description 10
229920001467 poly(styrenesulfonates) Polymers 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
238000001816 cooling Methods 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
235000019155 vitamin A Nutrition 0.000 description 8
239000011719 vitamin A Substances 0.000 description 8
FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 7
FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 7
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 7
229940045997 vitamin a Drugs 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
230000009286 beneficial effect Effects 0.000 description 6
230000000144 pharmacologic effect Effects 0.000 description 6
210000003491 skin Anatomy 0.000 description 6
239000004471 Glycine Substances 0.000 description 5
241000700159 Rattus Species 0.000 description 5
230000006378 damage Effects 0.000 description 5
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 5
239000005457 ice water Substances 0.000 description 5
229960003151 mercaptamine Drugs 0.000 description 5
210000000056 organ Anatomy 0.000 description 5
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000013543 active substance Substances 0.000 description 4
239000000654 additive Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
239000002537 cosmetic Substances 0.000 description 4
239000012043 crude product Substances 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000155 melt Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
210000001519 tissue Anatomy 0.000 description 4
230000029663 wound healing Effects 0.000 description 4
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
101100328518 Caenorhabditis elegans cnt-1 gene Proteins 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
208000027418 Wounds and injury Diseases 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000003708 ampul Substances 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
229960005261 aspartic acid Drugs 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 3
WMJRPJZQQSSDBU-UHFFFAOYSA-L disodium;sulfite;heptahydrate Chemical compound O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])=O WMJRPJZQQSSDBU-UHFFFAOYSA-L 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
238000005342 ion exchange Methods 0.000 description 3
210000003734 kidney Anatomy 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000002844 melting Methods 0.000 description 3
210000004400 mucous membrane Anatomy 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
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239000011573 trace mineral Substances 0.000 description 3
235000013619 trace mineral Nutrition 0.000 description 3
238000005406 washing Methods 0.000 description 3
FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 2
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
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MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 2
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PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
241000233866 Fungi Species 0.000 description 2
241000287828 Gallus gallus Species 0.000 description 2
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239000012535 impurity Substances 0.000 description 2
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229910052698 phosphorus Inorganic materials 0.000 description 2
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238000000746 purification Methods 0.000 description 2
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229910000029 sodium carbonate Inorganic materials 0.000 description 2
229910001415 sodium ion Inorganic materials 0.000 description 2
208000005801 spondylosis Diseases 0.000 description 2
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239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
PCPIXZZGBZWHJO-DKWTVANSSA-N (2r)-2-amino-3-sulfopropanoic acid;hydrate Chemical compound O.OC(=O)[C@@H](N)CS(O)(=O)=O PCPIXZZGBZWHJO-DKWTVANSSA-N 0.000 description 1
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NULDEVQACXJZLL-UHFFFAOYSA-N 2-(2-aminoethyldisulfanyl)ethylazanium;chloride Chemical compound Cl.NCCSSCCN NULDEVQACXJZLL-UHFFFAOYSA-N 0.000 description 1
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SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 description 1
229910002012 Aerosil® Inorganic materials 0.000 description 1
102000002260 Alkaline Phosphatase Human genes 0.000 description 1
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ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
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Animal Behavior & Ethology (AREA)
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Public Health (AREA)
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Biochemistry (AREA)
Molecular Biology (AREA)
Endocrinology (AREA)
Hematology (AREA)
Obesity (AREA)
Birds (AREA)
Immunology (AREA)
Dermatology (AREA)
Zoology (AREA)
Virology (AREA)
Biophysics (AREA)
Cell Biology (AREA)
Biotechnology (AREA)
Biomedical Technology (AREA)
Nutrition Science (AREA)
Gastroenterology & Hepatology (AREA)
Developmental Biology & Embryology (AREA)
Genetics & Genomics (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

CH539075A 1974-04-29 1975-04-28 CH617183A5 (hu)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU74FE00000928A HU171576B (hu)	1974-04-29	1974-04-29	Sposob otdelenija gamma-l-glutamil-taurina
HU74CI1558A HU174114B (hu)	1975-03-26	1975-03-26	Sposob poluchenija novykh proizvodnykh aminokislot

Publications (1)

Publication Number	Publication Date
CH617183A5 true CH617183A5 (hu)	1980-05-14

Family

ID=26318406

Family Applications (4)

Application Number	Title	Priority Date
CH539075A CH617183A5 (hu)	1974-04-29	1975-04-28
CH943379A CH624098A5 (hu)	1974-04-29	1979-10-19
CH943179A CH621333A5 (hu)	1974-04-29	1979-10-19
CH943279A CH621334A5 (hu)	1974-04-29	1979-10-19

Family Applications After (3)

Application Number	Title	Priority Date
CH943379A CH624098A5 (hu)	1974-04-29	1979-10-19
CH943179A CH621333A5 (hu)	1974-04-29	1979-10-19
CH943279A CH621334A5 (hu)	1974-04-29	1979-10-19

Country Status (23)

Country	Link
JP (1)	JPS6012347B2 (hu)
AR (3)	AR218222A1 (hu)
AT (6)	AT361902B (hu)
AU (1)	AU499173B2 (hu)
BE (1)	BE828546A (hu)
BG (4)	BG26369A4 (hu)
CA (1)	CA1051802A (hu)
CH (4)	CH617183A5 (hu)
CS (4)	CS209855B2 (hu)
DD (2)	DD122377A5 (hu)
DE (2)	DE2559989C3 (hu)
DK (10)	DK155433C (hu)
EG (1)	EG11847A (hu)
ES (4)	ES436986A1 (hu)
FI (1)	FI65990C (hu)
FR (1)	FR2279388A1 (hu)
GB (1)	GB1504541A (hu)
IL (1)	IL47149A (hu)
NL (1)	NL183186C (hu)
NO (2)	NO146430C (hu)
PL (2)	PL111745B1 (hu)
SE (2)	SE430164B (hu)
SU (1)	SU747419A3 (hu)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU178199B (en) *	1976-05-06	1982-03-28	Chinoin Gyogyszer Es Vegyeszet	New process for producing amides of omega-amino-carboxylic acids
HU180443B (en) *	1979-04-02	1983-03-28	Chinoin Gyogyszer Es Vegyeszet	Process for preparing a pharmaceutical preparation with synergetic action against radiation
HU185632B (en) *	1981-03-27	1985-03-28	Chinoin Gyogyszer Es Vegyeszet	New process for preparing gamma-glutamyl-taurine
CH665645A5 (fr) *	1981-07-09	1988-05-31	Michel Flork	Derives de dipeptides et leur procede de preparation.
HU208072B (en) *	1990-02-28	1993-08-30	Chinoin Gyogyszer Es Vegyeszet	Process for producing pharmaceutical composition suitable for preventing and curing autoimmune diseases and skin affections caused by heat and light radiacion
JPH0680964A (ja) *	1991-12-27	1994-03-22	Sogo Yatsukou Kk	活性酸素消去剤
JPH11180846A (ja) *	1997-12-15	1999-07-06	Sogo Pharmaceut Co Ltd	化粧料
DE10133197A1 (de) *	2001-07-07	2003-01-23	Beiersdorf Ag	Aminosäuren enthaltende kosmetische und dermatologische Zubereitungen zur Behandlung und aktiven Prävention trockener Haut und anderer negativer Veränderungen der physiologischen Homöostase der gesunden Haut
ES2533463T3 (es)	2006-10-12	2015-04-10	Bhi Limited Partnership	Métodos, compuestos, composiciones y vehículos para suministrar ácido 3-amino-1-propanosulfónico
US9662304B1 (en) *	2013-06-13	2017-05-30	Thermolife International, Llc	Substituted glutaurine compounds and substituted glutaurine derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU169462B (hu) *	1971-08-04	1976-11-28

1975
- 1975-04-23 IL IL47149A patent/IL47149A/xx unknown
- 1975-04-24 AT AT314075A patent/AT361902B/de not_active IP Right Cessation
- 1975-04-24 DE DE2559989A patent/DE2559989C3/de not_active Expired
- 1975-04-24 DE DE19752518160 patent/DE2518160A1/de active Granted
- 1975-04-25 FI FI751256A patent/FI65990C/fi not_active IP Right Cessation
- 1975-04-25 ES ES436986A patent/ES436986A1/es not_active Expired
- 1975-04-25 SE SE7504828A patent/SE430164B/xx not_active IP Right Cessation
- 1975-04-28 DD DD185727A patent/DD122377A5/xx unknown
- 1975-04-28 CA CA225,659A patent/CA1051802A/en not_active Expired
- 1975-04-28 SU SU752128794A patent/SU747419A3/ru active
- 1975-04-28 CH CH539075A patent/CH617183A5/de not_active IP Right Cessation
- 1975-04-28 NO NO751504A patent/NO146430C/no unknown
- 1975-04-28 AU AU80564/75A patent/AU499173B2/en not_active Expired
- 1975-04-28 DK DK182875A patent/DK155433C/da not_active IP Right Cessation
- 1975-04-28 EG EG262/75A patent/EG11847A/xx active
- 1975-04-28 DD DD193288A patent/DD125070A5/xx unknown
- 1975-04-28 FR FR7513230A patent/FR2279388A1/fr active Granted
- 1975-04-28 GB GB17608/75A patent/GB1504541A/en not_active Expired
- 1975-04-29 PL PL1975196801A patent/PL111745B1/pl unknown
- 1975-04-29 BE BE155914A patent/BE828546A/xx not_active IP Right Cessation
- 1975-04-29 BG BG030768A patent/BG26369A4/xx unknown
- 1975-04-29 BG BG029816A patent/BG26368A3/xx unknown
- 1975-04-29 PL PL1975196798A patent/PL111746B1/pl unknown
- 1975-04-29 BG BG030770A patent/BG26370A4/xx unknown
- 1975-04-29 BG BG030769A patent/BG26517A4/xx unknown
- 1975-04-29 CS CS752987A patent/CS209855B2/cs unknown
- 1975-04-29 NL NLAANVRAGE7505075,A patent/NL183186C/xx not_active IP Right Cessation
- 1975-04-30 JP JP50051612A patent/JPS6012347B2/ja not_active Expired
1976
- 1976-04-02 AR AR262770A patent/AR218222A1/es active
- 1976-04-02 AR AR262768A patent/AR218221A1/es active
- 1976-04-02 AR AR262769A patent/AR217236A1/es active
- 1976-11-13 ES ES453304A patent/ES453304A1/es not_active Expired
- 1976-11-13 ES ES453306A patent/ES453306A1/es not_active Expired
- 1976-11-13 ES ES453305A patent/ES453305A1/es not_active Expired
1977
- 1977-08-30 AT AT624777A patent/AT359084B/de not_active Expired
- 1977-08-30 AT AT624877A patent/AT359085B/de not_active IP Right Cessation
- 1977-08-30 AT AT624977A patent/AT351007B/de not_active IP Right Cessation
- 1977-10-06 DK DK442877A patent/DK158676C/da active
- 1977-10-06 DK DK442477A patent/DK155732C/da not_active IP Right Cessation
- 1977-10-06 DK DK442677A patent/DK159654C/da not_active IP Right Cessation
- 1977-10-06 DK DK442777A patent/DK442777A/da not_active Application Discontinuation
- 1977-10-06 DK DK442377A patent/DK155520C/da not_active IP Right Cessation
- 1977-10-06 DK DK442577A patent/DK442577A/da not_active Application Discontinuation
- 1977-10-06 DK DK443077A patent/DK159267C/da not_active IP Right Cessation
- 1977-10-06 DK DK442977A patent/DK442977A/da unknown
1978
- 1978-09-22 CS CS786128A patent/CS209856B2/cs unknown
- 1978-09-22 CS CS786129A patent/CS209857B2/cs unknown
- 1978-09-22 CS CS786130A patent/CS209858B2/cs unknown
- 1978-12-14 SE SE7812884A patent/SE441356B/sv not_active IP Right Cessation
1979
- 1979-04-30 AT AT0323079A patent/AT374484B/de not_active IP Right Cessation
- 1979-04-30 AT AT0323179A patent/AT370724B/de not_active IP Right Cessation
- 1979-10-19 CH CH943379A patent/CH624098A5/de not_active IP Right Cessation
- 1979-10-19 CH CH943179A patent/CH621333A5/de not_active IP Right Cessation
- 1979-10-19 CH CH943279A patent/CH621334A5/de not_active IP Right Cessation
1981
- 1981-03-10 NO NO810816A patent/NO149036C/no unknown
1983
- 1983-05-31 DK DK245783A patent/DK155672C/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK159267C (da)	1991-02-18
DK159654C (da)	1991-04-08
AT359085B (de)	1980-10-27
GB1504541A (en)	1978-03-22
DK155520B (da)	1989-04-17
NO146430B (no)	1982-06-21
DE2559989C3 (de)	1981-11-19
JPS514121A (hu)	1976-01-14
DK442477A (da)	1977-10-06
DK155732B (da)	1989-05-08
CS209856B2 (en)	1981-12-31
NL183186C (nl)	1988-08-16
DK155433B (da)	1989-04-10
NO149036B (no)	1983-10-24
AT370724B (de)	1983-04-25
DK442877A (da)	1977-10-06
DK245783A (da)	1983-05-31
DK442577A (da)	1977-10-06
IL47149A (en)	1979-05-31
DK442777A (da)	1977-10-06
AU499173B2 (en)	1979-04-05
DD122377A5 (hu)	1976-10-05
DD125070A5 (hu)	1977-03-30
NL7505075A (nl)	1975-10-31
DK442677A (da)	1977-10-06
ES436986A1 (es)	1977-06-16
FI751256A (hu)	1975-10-30
AU8056475A (en)	1976-11-04
DK158676B (da)	1990-07-02
DK155672C (da)	1989-10-09
SE430164B (sv)	1983-10-24
FI65990B (fi)	1984-04-30
BG26368A3 (bg)	1979-03-15
DK443077A (da)	1977-10-06
DK158676C (da)	1991-01-14
ATA624877A (de)	1980-03-15
SE441356B (sv)	1985-09-30
SU747419A3 (ru)	1980-07-23
CS209857B2 (en)	1981-12-31
DE2518160A1 (de)	1975-11-20
AT374484B (de)	1984-04-25
BE828546A (fr)	1975-08-18
DK245783D0 (da)	1983-05-31
DK442377A (da)	1977-10-06
JPS6012347B2 (ja)	1985-04-01
AT351007B (de)	1979-07-10
ES453304A1 (es)	1977-11-16
AR217236A1 (es)	1980-03-14
DK155672B (da)	1989-05-01
NO810816L (no)	1975-10-30
NO146430C (no)	1982-09-29
CS209858B2 (en)	1981-12-31
FR2279388A1 (fr)	1976-02-20
ATA323179A (de)	1982-09-15
ATA624777A (de)	1980-03-15
IL47149A0 (en)	1975-06-25
AR218221A1 (es)	1980-05-30
ATA314075A (de)	1980-09-15
CS209855B2 (en)	1981-12-31
EG11847A (en)	1979-06-30
CH624098A5 (hu)	1981-07-15
BG26370A4 (bg)	1979-03-15
CA1051802A (en)	1979-04-03
DK159267B (da)	1990-09-24
ES453306A1 (es)	1977-11-16
SE7812884L (sv)	1978-12-14
DE2559989B1 (de)	1981-02-05
PL111746B1 (en)	1980-09-30
SE7504828L (sv)	1975-10-30
NO751504L (hu)	1975-10-30
DK159654B (da)	1990-11-12
ATA624977A (de)	1978-12-15
BG26517A4 (bg)	1979-04-12
AT361902B (de)	1981-04-10
ATA323079A (de)	1983-09-15
DK155433C (da)	1989-10-16
NO149036C (no)	1984-02-01
DK155732C (da)	1989-10-02
ES453305A1 (es)	1977-11-16
AT359084B (de)	1980-10-27
CH621333A5 (hu)	1981-01-30
BG26369A4 (bg)	1979-03-15
CH621334A5 (hu)	1981-01-30
DK442977A (da)	1977-10-06
AR218222A1 (es)	1980-05-30
FR2279388B1 (hu)	1978-07-28
DE2518160C2 (hu)	1993-05-06
FI65990C (fi)	1984-08-10
DK182875A (da)	1975-10-30
PL111745B1 (en)	1980-09-30
DK155520C (da)	1989-10-16

Publication	Publication Date	Title
EP0079022B1 (de)	1986-03-12	Derivate der cis, endo-2-Azabicyclo-(3.3.0)-octan-3-carbonsäure, Verfahren zu ihrer Herstellung, diese enthaltende Mittel und deren Verwendung
DE2228012C3 (de)	1980-01-17	Phthalidester der 6- [D(-)- a Aminophenylacetamido] -penicillansäure und Verfahren zu seiner Herstellung
DE2634288B2 (hu)	1979-06-28
EP0003056B1 (de)	1982-08-18	N-substituierte omega-Aminoalkanoyl-omega-aminoalkansäuren, ihre Verwendung und Verfahren zu ihrer Herstellung sowie diese Verbindungen enthaltende Arzneimittel
DE2549783C3 (de)	1980-03-20	Triglyceride mit entzündungshemmender Wirkung
CH617183A5 (hu)	1980-05-14
EP0127726A1 (de)	1984-12-12	Hydroxamsäuren, ihre Herstellung und ihre Verwendung in pharmazeutischen Mitteln
JPS6133816B2 (hu)	1986-08-04
DE2156835B2 (de)	1973-12-20	Peptide und deren Verwendung zur Feststellung der Enzymsuffizienz bzw. -insuffizienz im Pankreas tierischer Organismen
CH621780A5 (hu)	1981-02-27
EP0100516B1 (de)	1987-10-14	3-Beta-(3'-(Carboxypropionyloxy))-ursa-9(11),12-dien-28-carbonsäure sowie ihre Salze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0013891B1 (de)	1982-05-19	Dipeptide zur Verwendung bei der Heilung von Krankheiten, einige neue Stoffe aus dieser Verbindungsgruppe, Dipeptide enthaltende Arzneimittel und deren Herstellung
EP0009777A1 (de)	1980-04-16	Retinsäure- und 7,8-Dehydro-retinsäure-N-(carboxy)-phenyl-amide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel
DE1926359A1 (de)	1970-05-21	oxylkansaeuren
DE2618936C3 (de)	1979-05-03	N-Acyl-glutamine, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
DE2736268A1 (de)	1978-02-16	Neue 5-thiazolalkylamin-derivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen
EP0007347B1 (de)	1981-12-30	Lipidsenkende Alkylenglykolderivate und Verfahren zu ihrer Herstellung
DE2145686C3 (de)	1978-02-16	2-Chlor-S-sulfamylbenzoesäurederivate, Verfahren zu ihrer Herstellung und Arzneimittel, die diese Verbindungen enthalten
DE1670539C3 (de)	1975-10-09	Diacylthiamine und Verfahren zu deren Herstellung
DE1795423C3 (de)	1974-02-28	Pivaloyloxymethyl-alpha-aminobenzylpenicillinat
DE3153733C2 (de)	1994-05-19	Thiocarnitinhydrochloride
DE2357778C3 (de)	1977-10-06	Neue Ester von 21-Mercaptosteroiden, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zubereitungen
DE2753768A1 (de)	1979-06-07	Antiphologistisch wirkende arzneimittel
DE1049869B (de)	1959-02-05	Verfahren zur Herstellung von a-Glutamyl-peptiden
DE2145686B2 (de)	1977-07-07	2-chlor-5-sulfamylbenzoesaeurederivate, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten

Legal Events

Date	Code	Title	Description
1994-12-30	PL	Patent ceased
2024-10-31	PL	Patent ceased