CH617183A5 - - Google Patents
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- CH617183A5 CH617183A5 CH539075A CH539075A CH617183A5 CH 617183 A5 CH617183 A5 CH 617183A5 CH 539075 A CH539075 A CH 539075A CH 539075 A CH539075 A CH 539075A CH 617183 A5 CH617183 A5 CH 617183A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- compounds
- general formula
- compound
- formula
- Prior art date
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- 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
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- 239000011573 trace mineral Substances 0.000 description 3
- 235000013619 trace mineral Nutrition 0.000 description 3
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- 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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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 2
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
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- 229910052698 phosphorus Inorganic materials 0.000 description 2
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- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 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
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- 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NULDEVQACXJZLL-UHFFFAOYSA-N 2-(2-aminoethyldisulfanyl)ethylazanium;chloride Chemical compound Cl.NCCSSCCN NULDEVQACXJZLL-UHFFFAOYSA-N 0.000 description 1
- WJAXXWSZNSFVNG-UHFFFAOYSA-N 2-bromoethanamine;hydron;bromide Chemical compound [Br-].[NH3+]CCBr WJAXXWSZNSFVNG-UHFFFAOYSA-N 0.000 description 1
- 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
- 108020004774 Alkaline Phosphatase Proteins 0.000 description 1
- 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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-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Birds (AREA)
- Hematology (AREA)
- Dermatology (AREA)
- Zoology (AREA)
- Immunology (AREA)
- Nutrition Science (AREA)
- Developmental Biology & Embryology (AREA)
- Biophysics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biomedical Technology (AREA)
- Biotechnology (AREA)
- Cell Biology (AREA)
- Genetics & Genomics (AREA)
- Virology (AREA)
- Gastroenterology & Hepatology (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)
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 (zh) | 1980-05-14 |
Family
ID=26318406
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH539075A CH617183A5 (zh) | 1974-04-29 | 1975-04-28 | |
| CH943279A CH621334A5 (zh) | 1974-04-29 | 1979-10-19 | |
| CH943379A CH624098A5 (zh) | 1974-04-29 | 1979-10-19 | |
| CH943179A CH621333A5 (zh) | 1974-04-29 | 1979-10-19 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH943279A CH621334A5 (zh) | 1974-04-29 | 1979-10-19 | |
| CH943379A CH624098A5 (zh) | 1974-04-29 | 1979-10-19 | |
| CH943179A CH621333A5 (zh) | 1974-04-29 | 1979-10-19 |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS6012347B2 (zh) |
| AR (3) | AR217236A1 (zh) |
| AT (6) | AT361902B (zh) |
| AU (1) | AU499173B2 (zh) |
| BE (1) | BE828546A (zh) |
| BG (4) | BG26517A4 (zh) |
| CA (1) | CA1051802A (zh) |
| CH (4) | CH617183A5 (zh) |
| CS (4) | CS209855B2 (zh) |
| DD (2) | DD125070A5 (zh) |
| DE (2) | DE2518160A1 (zh) |
| DK (10) | DK155433C (zh) |
| EG (1) | EG11847A (zh) |
| ES (4) | ES436986A1 (zh) |
| FI (1) | FI65990C (zh) |
| FR (1) | FR2279388A1 (zh) |
| GB (1) | GB1504541A (zh) |
| IL (1) | IL47149A (zh) |
| NL (1) | NL183186C (zh) |
| NO (2) | NO146430C (zh) |
| PL (2) | PL111746B1 (zh) |
| SE (2) | SE430164B (zh) |
| SU (1) | SU747419A3 (zh) |
Families Citing this family (10)
| 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 |
| KR101443573B1 (ko) | 2006-10-12 | 2014-11-03 | 비에이치아이 리미티드 파트너쉽 | 3-아미노-1-프로판설폰산을 전달하기 위한 방법, 화합물, 조성물 및 비히클 |
| US9662304B1 (en) * | 2013-06-13 | 2017-05-30 | Thermolife International, Llc | Substituted glutaurine compounds and substituted glutaurine derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU169462B (zh) * | 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 DE19752518160 patent/DE2518160A1/de active Granted
- 1975-04-24 DE DE2559989A patent/DE2559989C3/de not_active Expired
- 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 NO NO751504A patent/NO146430C/no unknown
- 1975-04-28 GB GB17608/75A patent/GB1504541A/en not_active Expired
- 1975-04-28 AU AU80564/75A patent/AU499173B2/en not_active Expired
- 1975-04-28 DD DD193288A patent/DD125070A5/xx unknown
- 1975-04-28 DD DD185727A patent/DD122377A5/xx unknown
- 1975-04-28 CA CA225,659A patent/CA1051802A/en not_active Expired
- 1975-04-28 EG EG262/75A patent/EG11847A/xx active
- 1975-04-28 FR FR7513230A patent/FR2279388A1/fr active Granted
- 1975-04-28 CH CH539075A patent/CH617183A5/de not_active IP Right Cessation
- 1975-04-28 SU SU752128794A patent/SU747419A3/ru active
- 1975-04-28 DK DK182875A patent/DK155433C/da not_active IP Right Cessation
- 1975-04-29 BG BG030769A patent/BG26517A4/xx unknown
- 1975-04-29 NL NLAANVRAGE7505075,A patent/NL183186C/xx not_active IP Right Cessation
- 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 BG030770A patent/BG26370A4/xx unknown
- 1975-04-29 BG BG029816A patent/BG26368A3/xx unknown
- 1975-04-29 CS CS752987A patent/CS209855B2/cs unknown
- 1975-04-29 PL PL1975196798A patent/PL111746B1/pl unknown
- 1975-04-29 PL PL1975196801A patent/PL111745B1/pl unknown
- 1975-04-30 JP JP50051612A patent/JPS6012347B2/ja not_active Expired
-
1976
- 1976-04-02 AR AR262769A patent/AR217236A1/es active
- 1976-04-02 AR AR262768A patent/AR218221A1/es active
- 1976-04-02 AR AR262770A patent/AR218222A1/es active
- 1976-11-13 ES ES453305A patent/ES453305A1/es not_active Expired
- 1976-11-13 ES ES453304A patent/ES453304A1/es not_active Expired
- 1976-11-13 ES ES453306A patent/ES453306A1/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 DK442777A patent/DK442777A/da not_active Application Discontinuation
- 1977-10-06 DK DK442677A patent/DK159654C/da not_active IP Right Cessation
- 1977-10-06 DK DK443077A patent/DK159267C/da not_active IP Right Cessation
- 1977-10-06 DK DK442577A patent/DK442577A/da not_active Application Discontinuation
- 1977-10-06 DK DK442877A patent/DK158676C/da active
- 1977-10-06 DK DK442977A patent/DK442977A/da unknown
- 1977-10-06 DK DK442477A patent/DK155732C/da not_active IP Right Cessation
- 1977-10-06 DK DK442377A patent/DK155520C/da not_active IP Right Cessation
-
1978
- 1978-09-22 CS CS786130A patent/CS209858B2/cs unknown
- 1978-09-22 CS CS786129A patent/CS209857B2/cs unknown
- 1978-09-22 CS CS786128A patent/CS209856B2/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 CH943279A patent/CH621334A5/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
-
1981
- 1981-03-10 NO NO810816A patent/NO149036C/no unknown
-
1983
- 1983-05-31 DK DK245783A patent/DK155672C/da not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |