JPS6124377B2 - - Google Patents
Info
- Publication number
- JPS6124377B2 JPS6124377B2 JP57215670A JP21567082A JPS6124377B2 JP S6124377 B2 JPS6124377 B2 JP S6124377B2 JP 57215670 A JP57215670 A JP 57215670A JP 21567082 A JP21567082 A JP 21567082A JP S6124377 B2 JPS6124377 B2 JP S6124377B2
- Authority
- JP
- Japan
- Prior art keywords
- residue
- general formula
- mmol
- carbobenzyloxy
- formula
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- -1 hydroxy, p-nitrophenoxy Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 230000009471 action Effects 0.000 description 21
- 239000004480 active ingredient Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 230000000694 effects Effects 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 10
- 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 9
- 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 9
- 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 9
- 235000019155 vitamin A Nutrition 0.000 description 9
- 239000011719 vitamin A Substances 0.000 description 9
- 229940045997 vitamin a Drugs 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 239000003826 tablet Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 229960003080 taurine Drugs 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 229960002989 glutamic acid Drugs 0.000 description 5
- 210000000056 organ Anatomy 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 210000004400 mucous membrane Anatomy 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 210000003491 skin Anatomy 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- 230000029663 wound healing Effects 0.000 description 4
- 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 3
- SNKZJIOFVMKAOJ-UHFFFAOYSA-N 3-Aminopropanesulfonate Chemical compound NCCCS(O)(=O)=O SNKZJIOFVMKAOJ-UHFFFAOYSA-N 0.000 description 3
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- SUHOOTKUPISOBE-UHFFFAOYSA-N O-phosphoethanolamine Chemical compound NCCOP(O)(O)=O SUHOOTKUPISOBE-UHFFFAOYSA-N 0.000 description 3
- 229960005261 aspartic acid Drugs 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 229960004544 cortisone Drugs 0.000 description 3
- XVOYSCVBGLVSOL-UHFFFAOYSA-N cysteic acid Chemical compound OC(=O)C(N)CS(O)(=O)=O XVOYSCVBGLVSOL-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 229940088598 enzyme Drugs 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 102000016943 Muramidase Human genes 0.000 description 2
- 108010014251 Muramidase Proteins 0.000 description 2
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 206010041591 Spinal osteoarthritis Diseases 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 208000036142 Viral infection Diseases 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 239000003674 animal food additive Substances 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 210000000845 cartilage Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000013330 chicken meat Nutrition 0.000 description 2
- 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 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 235000010335 lysozyme Nutrition 0.000 description 2
- 229960000274 lysozyme Drugs 0.000 description 2
- 239000004325 lysozyme 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
- 230000004060 metabolic process Effects 0.000 description 2
- 201000009240 nasopharyngitis Diseases 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 210000002345 respiratory system Anatomy 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 208000005801 spondylosis Diseases 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000011573 trace mineral Substances 0.000 description 2
- 235000013619 trace mineral Nutrition 0.000 description 2
- 230000003612 virological effect Effects 0.000 description 2
- KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-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
- 206010003791 Aura Diseases 0.000 description 1
- 208000000412 Avitaminosis Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000010392 Bone Fractures Diseases 0.000 description 1
- 206010006458 Bronchitis chronic Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 229920001287 Chondroitin sulfate Polymers 0.000 description 1
- UDMBCSSLTHHNCD-UHFFFAOYSA-N Coenzym Q(11) Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(O)=O)C(O)C1O UDMBCSSLTHHNCD-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 206010011732 Cyst Diseases 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical compound CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 description 1
- 208000003556 Dry Eye Syndromes Diseases 0.000 description 1
- 206010013774 Dry eye Diseases 0.000 description 1
- 206010051814 Eschar Diseases 0.000 description 1
- 208000000571 Fibrocystic breast disease Diseases 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010016818 Fluorosis Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 102000006947 Histones Human genes 0.000 description 1
- 108010033040 Histones Proteins 0.000 description 1
- 206010020565 Hyperaemia Diseases 0.000 description 1
- 206010021135 Hypovitaminosis Diseases 0.000 description 1
- 208000002260 Keloid Diseases 0.000 description 1
- 206010023330 Keloid scar Diseases 0.000 description 1
- 208000009319 Keratoconjunctivitis Sicca Diseases 0.000 description 1
- 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 1
- 239000004166 Lanolin Substances 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 102000007327 Protamines Human genes 0.000 description 1
- 108010007568 Protamines Proteins 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 206010039710 Scleroderma Diseases 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 206010042220 Stress ulcer Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 208000002847 Surgical Wound Diseases 0.000 description 1
- 102000016540 Tyrosine aminotransferases Human genes 0.000 description 1
- 108010042606 Tyrosine transaminase Proteins 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 229930003448 Vitamin K Natural products 0.000 description 1
- 235000019742 Vitamins premix Nutrition 0.000 description 1
- 206010047642 Vitiligo Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 230000003044 adaptive effect Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 1
- 229950006790 adenosine phosphate Drugs 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 206010003549 asthenia Diseases 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 210000002805 bone matrix Anatomy 0.000 description 1
- 208000011803 breast fibrocystic disease Diseases 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 208000005882 cadmium poisoning Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229940059329 chondroitin sulfate Drugs 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000000112 colonic effect Effects 0.000 description 1
- 210000000795 conjunctiva Anatomy 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 210000000695 crystalline len Anatomy 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical class CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 208000004042 dental fluorosis Diseases 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 210000002257 embryonic structure Anatomy 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 231100000333 eschar Toxicity 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 210000002175 goblet cell Anatomy 0.000 description 1
- 210000002288 golgi apparatus Anatomy 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 210000003630 histaminocyte Anatomy 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 210000001117 keloid Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 230000006386 memory function Effects 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 229960003151 mercaptamine Drugs 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 239000003538 oral antidiabetic agent Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 238000007248 oxidative elimination reaction Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000199 parathyroid hormone Substances 0.000 description 1
- 231100000915 pathological change Toxicity 0.000 description 1
- 230000036285 pathological change Effects 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 208000028169 periodontal disease Diseases 0.000 description 1
- 230000003239 periodontal effect Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 229940048914 protamine Drugs 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- OENLEHTYJXMVBG-UHFFFAOYSA-N pyridine;hydrate Chemical compound [OH-].C1=CC=[NH+]C=C1 OENLEHTYJXMVBG-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000004223 radioprotective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000002784 sclerotic effect Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- GJPYYNMJTJNYTO-UHFFFAOYSA-J sodium aluminium sulfate Chemical compound [Na+].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GJPYYNMJTJNYTO-UHFFFAOYSA-J 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000021055 solid food Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 210000001258 synovial membrane Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001519 thymoleptic effect Effects 0.000 description 1
- 239000005495 thyroid hormone Substances 0.000 description 1
- 229940036555 thyroid hormone Drugs 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 230000018889 transepithelial transport Effects 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 210000005239 tubule Anatomy 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 150000002266 vitamin A derivatives Chemical class 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 208000030401 vitamin deficiency disease Diseases 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- 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)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Polyamides (AREA)
- Cosmetics (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU928 | 1974-04-29 | ||
| HU74FE00000928A HU171576B (hu) | 1974-04-29 | 1974-04-29 | Sposob otdelenija gamma-l-glutamil-taurina |
| HU1558 | 1975-03-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58131952A JPS58131952A (ja) | 1983-08-06 |
| JPS6124377B2 true JPS6124377B2 (et) | 1986-06-10 |
Family
ID=10996115
Family Applications (13)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5195775A Expired JPS6039647B2 (ja) | 1974-04-29 | 1975-04-28 | ガンマ−ｌ−グルタミル−タウリンの単離方法 |
| JP57215673A Expired JPS6043360B2 (ja) | 1974-04-29 | 1982-12-10 | 新規アミノ酸誘導体の製法 |
| JP21566982A Expired JPS6049629B2 (ja) | 1974-04-29 | 1982-12-10 | 新規アミノ酸誘導体の製法 |
| JP21567482A Pending JPS60120995A (ja) | 1974-04-29 | 1982-12-10 | 新規アミノ酸誘導体の製法 |
| JP21675982A Expired JPS6011026B2 (ja) | 1974-04-29 | 1982-12-10 | 新規アミノ酸誘導体の製法 |
| JP21567582A Expired JPS6011025B2 (ja) | 1974-04-29 | 1982-12-10 | 新規アミノ酸誘導体の製法 |
| JP21567282A Pending JPS58131960A (ja) | 1974-04-29 | 1982-12-10 | 新規アミノ酸誘導体の製法 |
| JP21567182A Expired JPS6011024B2 (ja) | 1974-04-29 | 1982-12-10 | 新規アミノ酸誘導体の製法 |
| JP57215670A Granted JPS58131952A (ja) | 1974-04-29 | 1982-12-10 | 新規アミノ酸誘導体の製法 |
| JP12542984A Granted JPS6041657A (ja) | 1974-04-29 | 1984-06-20 | 新規アミノ酸誘導体の製法 |
| JP12543084A Granted JPS6041658A (ja) | 1974-04-29 | 1984-06-20 | 新規アミノ酸誘導体の製法 |
| JP12655184A Granted JPS6089488A (ja) | 1974-04-29 | 1984-06-21 | 新規アミノ酸誘導体の製法 |
| JP12655284A Granted JPS6041656A (ja) | 1974-04-29 | 1984-06-21 | 新規アミノ酸誘導体の製法 |
Family Applications Before (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5195775A Expired JPS6039647B2 (ja) | 1974-04-29 | 1975-04-28 | ガンマ−ｌ−グルタミル−タウリンの単離方法 |
| JP57215673A Expired JPS6043360B2 (ja) | 1974-04-29 | 1982-12-10 | 新規アミノ酸誘導体の製法 |
| JP21566982A Expired JPS6049629B2 (ja) | 1974-04-29 | 1982-12-10 | 新規アミノ酸誘導体の製法 |
| JP21567482A Pending JPS60120995A (ja) | 1974-04-29 | 1982-12-10 | 新規アミノ酸誘導体の製法 |
| JP21675982A Expired JPS6011026B2 (ja) | 1974-04-29 | 1982-12-10 | 新規アミノ酸誘導体の製法 |
| JP21567582A Expired JPS6011025B2 (ja) | 1974-04-29 | 1982-12-10 | 新規アミノ酸誘導体の製法 |
| JP21567282A Pending JPS58131960A (ja) | 1974-04-29 | 1982-12-10 | 新規アミノ酸誘導体の製法 |
| JP21567182A Expired JPS6011024B2 (ja) | 1974-04-29 | 1982-12-10 | 新規アミノ酸誘導体の製法 |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12542984A Granted JPS6041657A (ja) | 1974-04-29 | 1984-06-20 | 新規アミノ酸誘導体の製法 |
| JP12543084A Granted JPS6041658A (ja) | 1974-04-29 | 1984-06-20 | 新規アミノ酸誘導体の製法 |
| JP12655184A Granted JPS6089488A (ja) | 1974-04-29 | 1984-06-21 | 新規アミノ酸誘導体の製法 |
| JP12655284A Granted JPS6041656A (ja) | 1974-04-29 | 1984-06-21 | 新規アミノ酸誘導体の製法 |
Country Status (16)
| Country | Link |
|---|---|
| JP (13) | JPS6039647B2 (et) |
| AR (1) | AR207243A1 (et) |
| AU (1) | AU497133B2 (et) |
| CS (1) | CS185685B2 (et) |
| DD (1) | DD119580A2 (et) |
| DK (1) | DK182675A (et) |
| ES (1) | ES437046A2 (et) |
| FI (1) | FI53269C (et) |
| HU (1) | HU171576B (et) |
| IL (1) | IL47117A (et) |
| IN (11) | IN141368B (et) |
| NZ (1) | NZ177337A (et) |
| PL (2) | PL110477B1 (et) |
| SU (4) | SU638243A3 (et) |
| YU (1) | YU37477B (et) |
| ZA (1) | ZA752394B (et) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01108884U (et) * | 1988-01-18 | 1989-07-24 | ||
| JPH0245880U (et) * | 1988-09-24 | 1990-03-29 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6233877U (et) * | 1985-08-19 | 1987-02-27 | ||
| JP3592497B2 (ja) * | 1997-09-08 | 2004-11-24 | 日本ブレーキ工業株式会社 | 加熱接着方法及び装置 |
| HK1077154A2 (en) | 2003-12-30 | 2006-02-03 | Vasogen Ireland Ltd | Valve assembly |
| JP2006336072A (ja) * | 2005-06-02 | 2006-12-14 | Tokyo Electric Power Co Inc:The | 簡易防食装置 |
| US7998134B2 (en) | 2007-05-16 | 2011-08-16 | Icu Medical, Inc. | Medical connector |
| US20070088293A1 (en) | 2005-07-06 | 2007-04-19 | Fangrow Thomas F Jr | Medical connector with closeable male luer |
| US9168366B2 (en) | 2008-12-19 | 2015-10-27 | Icu Medical, Inc. | Medical connector with closeable luer connector |
| JP6553357B2 (ja) | 2011-09-09 | 2019-07-31 | アイシーユー・メディカル・インコーポレーテッド | 耐流体性嵌合インターフェースを備えた医療用コネクタ |
-
1974
- 1974-04-29 HU HU74FE00000928A patent/HU171576B/hu unknown
-
1975
- 1975-04-15 ZA ZA00752394A patent/ZA752394B/xx unknown
- 1975-04-18 AU AU80320/75A patent/AU497133B2/en not_active Expired
- 1975-04-18 IL IL4711775A patent/IL47117A/xx unknown
- 1975-04-21 IN IN804/CAL/75A patent/IN141368B/en unknown
- 1975-04-24 CS CS288775A patent/CS185685B2/cs unknown
- 1975-04-26 ES ES437046A patent/ES437046A2/es not_active Expired
- 1975-04-26 IN IN846/CAL/75A patent/IN142471B/en unknown
- 1975-04-28 DD DD18572675A patent/DD119580A2/xx unknown
- 1975-04-28 YU YU109075A patent/YU37477B/xx unknown
- 1975-04-28 FI FI751271A patent/FI53269C/fi not_active IP Right Cessation
- 1975-04-28 DK DK182675A patent/DK182675A/da unknown
- 1975-04-28 JP JP5195775A patent/JPS6039647B2/ja not_active Expired
- 1975-04-28 SU SU752129107A patent/SU638243A3/ru active
- 1975-04-28 NZ NZ17733775A patent/NZ177337A/xx unknown
- 1975-04-29 PL PL18004975A patent/PL110477B1/pl unknown
- 1975-04-29 PL PL19680275A patent/PL108181B1/pl unknown
-
1976
- 1976-04-29 AR AR25854176A patent/AR207243A1/es active
- 1976-05-14 SU SU762356005A patent/SU670214A3/ru active
- 1976-05-26 SU SU762362204A patent/SU648082A3/ru active
- 1976-05-26 SU SU762362206A patent/SU673176A3/ru active
-
1977
- 1977-02-17 IN IN235/CAL/77A patent/IN146299B/en unknown
-
1978
- 1978-09-22 IN IN1058/CAL/78A patent/IN148247B/en unknown
- 1978-09-22 IN IN1059/CAL/78A patent/IN148248B/en unknown
- 1978-09-22 IN IN1057/CAL/78A patent/IN148246B/en unknown
- 1978-09-22 IN IN1054/CAL/78A patent/IN148243B/en unknown
- 1978-09-22 IN IN1055/CAL/78A patent/IN148244B/en unknown
- 1978-09-22 IN IN1053/CAL/78A patent/IN148242B/en unknown
- 1978-09-22 IN IN1060/CAL/78A patent/IN148249B/en unknown
- 1978-09-22 IN IN1056/CAL/78A patent/IN148245B/en unknown
-
1982
- 1982-12-10 JP JP57215673A patent/JPS6043360B2/ja not_active Expired
- 1982-12-10 JP JP21566982A patent/JPS6049629B2/ja not_active Expired
- 1982-12-10 JP JP21567482A patent/JPS60120995A/ja active Pending
- 1982-12-10 JP JP21675982A patent/JPS6011026B2/ja not_active Expired
- 1982-12-10 JP JP21567582A patent/JPS6011025B2/ja not_active Expired
- 1982-12-10 JP JP21567282A patent/JPS58131960A/ja active Pending
- 1982-12-10 JP JP21567182A patent/JPS6011024B2/ja not_active Expired
- 1982-12-10 JP JP57215670A patent/JPS58131952A/ja active Granted
-
1984
- 1984-06-20 JP JP12542984A patent/JPS6041657A/ja active Granted
- 1984-06-20 JP JP12543084A patent/JPS6041658A/ja active Granted
- 1984-06-21 JP JP12655184A patent/JPS6089488A/ja active Granted
- 1984-06-21 JP JP12655284A patent/JPS6041656A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01108884U (et) * | 1988-01-18 | 1989-07-24 | ||
| JPH0245880U (et) * | 1988-09-24 | 1990-03-29 |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4734276A (en) | L-lysine pyruvate and l- histidine pyruvate and their use in therapy of tissue and mucosa damage | |
| JPH07501539A (ja) | Ｎ，ｎ’−ジアセチルシスチンの有機塩 | |
| EP0705244A1 (de) | Nitrato-aminosäure-disulfide zur therapie von erkrankungen des herz-kreislauf-systems | |
| JPS6124377B2 (et) | ||
| JPS6012347B2 (ja) | 新規アミノ酸誘導体の製法 | |
| PT90301B (pt) | Processo para a preparacao de novos derivados 6-fosfono-alquilicos de purina e de composicoes farmaceuticas que os contem | |
| FR2502627A1 (fr) | Derives thioliques de l'erythromycine a activite therapeutique, procede de preparation et produits pharmaceutiques dans lesquels ils apparaissent | |
| JPS58502000A (ja) | 置換ピロ−ル | |
| CS209861B2 (cs) | Způsob výroby nových derivátů aminokyselin | |
| EP0750635A1 (fr) | Peptides pour inhiber la liberation de pepsine | |
| BE881677A (fr) | Nouveaux derives d'acide penicillanique utile notamment comme antibiotiques et leurs procedes de preparation | |
| FR2534909A1 (fr) | Nouveaux derives amines de l'acide 4-phenyl 4-oxo 2-butenoiques, leur preparation, leur application comme medicaments et les compositions les renfermant |