AU615244B2 - New derivatives of cysteine, processes for their preparation and their use - Google Patents
New derivatives of cysteine, processes for their preparation and their use Download PDFInfo
- Publication number
- AU615244B2 AU615244B2 AU27292/88A AU2729288A AU615244B2 AU 615244 B2 AU615244 B2 AU 615244B2 AU 27292/88 A AU27292/88 A AU 27292/88A AU 2729288 A AU2729288 A AU 2729288A AU 615244 B2 AU615244 B2 AU 615244B2
- Authority
- AU
- Australia
- Prior art keywords
- compound
- diseases
- international
- document
- cysteine
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 18
- 230000008569 process Effects 0.000 title claims description 10
- 125000000151 cysteine group Chemical class N[C@@H](CS)C(=O)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 48
- 230000003287 optical effect Effects 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 12
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 11
- 208000019693 Lung disease Diseases 0.000 claims description 8
- 210000004072 lung Anatomy 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 5
- 208000004852 Lung Injury Diseases 0.000 claims description 4
- 206010069363 Traumatic lung injury Diseases 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 231100000515 lung injury Toxicity 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 208000018631 connective tissue disease Diseases 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 230000002757 inflammatory effect Effects 0.000 claims description 3
- 210000003097 mucus Anatomy 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 241000509579 Draco Species 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- 241000448280 Elates Species 0.000 claims 2
- 235000019988 mead Nutrition 0.000 claims 2
- LSIXBBPOJBJQHN-UHFFFAOYSA-N 2,3-Dimethylbicyclo[2.2.1]hept-2-ene Chemical compound C1CC2C(C)=C(C)C1C2 LSIXBBPOJBJQHN-UHFFFAOYSA-N 0.000 claims 1
- 241000928610 Coula Species 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- JXVIIQLNUPXOII-UHFFFAOYSA-N Siduron Chemical compound CC1CCCCC1NC(=O)NC1=CC=CC=C1 JXVIIQLNUPXOII-UHFFFAOYSA-N 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 238000002405 diagnostic procedure Methods 0.000 claims 1
- UZUQIGYNEIUVNT-UHFFFAOYSA-N n-[4-(furan-2-yl)-1,3-thiazol-2-yl]formamide Chemical compound S1C(NC=O)=NC(C=2OC=CC=2)=C1 UZUQIGYNEIUVNT-UHFFFAOYSA-N 0.000 claims 1
- 229920001935 styrene-ethylene-butadiene-styrene Polymers 0.000 claims 1
- 230000000153 supplemental effect Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 19
- BWBQXMAXLAHHTK-YFKPBYRVSA-N (2r)-2-(2-methylpropanoylamino)-3-sulfanylpropanoic acid Chemical compound CC(C)C(=O)N[C@@H](CS)C(O)=O BWBQXMAXLAHHTK-YFKPBYRVSA-N 0.000 description 10
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 150000003573 thiols Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229960002433 cysteine Drugs 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000001828 Gelatine Substances 0.000 description 6
- -1 Sulphydryl Compounds Chemical class 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 229920000159 gelatin Polymers 0.000 description 6
- 235000019322 gelatine Nutrition 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- NKIKSSZMMDDQRL-YFKPBYRVSA-N (2r)-2-(2,2-dimethylpropanoylamino)-3-sulfanylpropanoic acid Chemical compound CC(C)(C)C(=O)N[C@@H](CS)C(O)=O NKIKSSZMMDDQRL-YFKPBYRVSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 229920002472 Starch Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 235000018417 cysteine Nutrition 0.000 description 4
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 206010006458 Bronchitis chronic Diseases 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004201 L-cysteine Substances 0.000 description 3
- 235000013878 L-cysteine Nutrition 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 206010006451 bronchitis Diseases 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 208000007451 chronic bronchitis Diseases 0.000 description 3
- 150000001944 cysteine derivatives Chemical class 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 230000002503 metabolic effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000036542 oxidative stress Effects 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 235000010356 sorbitol Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- 229920000945 Amylopectin Polymers 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229930195710 D‐cysteine Natural products 0.000 description 2
- 206010016654 Fibrosis Diseases 0.000 description 2
- 108010024636 Glutathione Proteins 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 235000013681 dietary sucrose Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000004761 fibrosis Effects 0.000 description 2
- 229960003180 glutathione Drugs 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000002926 oxygen Chemical class 0.000 description 2
- 230000036470 plasma concentration Effects 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 235000012015 potatoes Nutrition 0.000 description 2
- LJPYJRMMPVFEKR-UHFFFAOYSA-N prop-2-ynylurea Chemical compound NC(=O)NCC#C LJPYJRMMPVFEKR-UHFFFAOYSA-N 0.000 description 2
- 238000006884 silylation reaction Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 229960004793 sucrose Drugs 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- JLGDXLJLBLWEPD-YFKPBYRVSA-N (2r)-2-(butanoylamino)-3-sulfanylpropanoic acid Chemical compound CCCC(=O)N[C@@H](CS)C(O)=O JLGDXLJLBLWEPD-YFKPBYRVSA-N 0.000 description 1
- NKIKSSZMMDDQRL-RXMQYKEDSA-N (2s)-2-(2,2-dimethylpropanoylamino)-3-sulfanylpropanoic acid Chemical compound CC(C)(C)C(=O)N[C@H](CS)C(O)=O NKIKSSZMMDDQRL-RXMQYKEDSA-N 0.000 description 1
- BWBQXMAXLAHHTK-RXMQYKEDSA-N (2s)-2-(2-methylpropanoylamino)-3-sulfanylpropanoic acid Chemical compound CC(C)C(=O)N[C@H](CS)C(O)=O BWBQXMAXLAHHTK-RXMQYKEDSA-N 0.000 description 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- BWBQXMAXLAHHTK-UHFFFAOYSA-N 2-(2-methylpropanoylamino)-3-sulfanylpropanoic acid Chemical compound CC(C)C(=O)NC(CS)C(O)=O BWBQXMAXLAHHTK-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 102000010079 Coenzyme A-Transferases Human genes 0.000 description 1
- 108010077385 Coenzyme A-Transferases Proteins 0.000 description 1
- 208000027932 Collagen disease Diseases 0.000 description 1
- 201000003883 Cystic fibrosis Diseases 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- 239000004150 EU approved colour Substances 0.000 description 1
- 206010014561 Emphysema Diseases 0.000 description 1
- 244000165918 Eucalyptus papuana Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- 208000011623 Obstructive Lung disease Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 206010035742 Pneumonitis Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 206010037423 Pulmonary oedema Diseases 0.000 description 1
- 208000017442 Retinal disease Diseases 0.000 description 1
- 206010038923 Retinopathy Diseases 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000000729 antidote Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 206010006475 bronchopulmonary dysplasia Diseases 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 239000000850 decongestant Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000005251 gamma ray Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000003676 hair preparation Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 231100000304 hepatotoxicity Toxicity 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000007056 liver toxicity Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Chemical class 0.000 description 1
- 239000011777 magnesium Chemical class 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000000510 mucolytic effect Effects 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- TWEGKFXBDXYJIU-UHFFFAOYSA-M sodium;2-methylpropanoate Chemical compound [Na+].CC(C)C([O-])=O TWEGKFXBDXYJIU-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000001839 systemic circulation Effects 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000013417 toxicology model Methods 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
- C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Ophthalmology & Optometry (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pulmonology (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)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE8704542 | 1987-11-19 | ||
SE8704542A SE8704542D0 (sv) | 1987-11-19 | 1987-11-19 | New derivatives of cysteine |
Publications (2)
Publication Number | Publication Date |
---|---|
AU2729288A AU2729288A (en) | 1989-06-14 |
AU615244B2 true AU615244B2 (en) | 1991-09-26 |
Family
ID=20370284
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU27292/88A Ceased AU615244B2 (en) | 1987-11-19 | 1988-11-16 | New derivatives of cysteine, processes for their preparation and their use |
Country Status (27)
Country | Link |
---|---|
EP (1) | EP0317540B1 (en, 2012) |
JP (1) | JPH02502189A (en, 2012) |
KR (1) | KR890701553A (en, 2012) |
CN (1) | CN1033802A (en, 2012) |
AR (1) | AR245693A1 (en, 2012) |
AT (1) | ATE79371T1 (en, 2012) |
AU (1) | AU615244B2 (en, 2012) |
DD (1) | DD275865A5 (en, 2012) |
DE (1) | DE3873696T2 (en, 2012) |
DK (1) | DK347789D0 (en, 2012) |
EG (1) | EG19066A (en, 2012) |
ES (1) | ES2051891T3 (en, 2012) |
FI (1) | FI93442C (en, 2012) |
GR (1) | GR3006115T3 (en, 2012) |
HU (1) | HU203224B (en, 2012) |
IE (1) | IE61181B1 (en, 2012) |
IL (1) | IL88342A (en, 2012) |
IS (1) | IS1544B (en, 2012) |
MY (1) | MY106950A (en, 2012) |
NO (1) | NO170413C (en, 2012) |
NZ (1) | NZ226898A (en, 2012) |
PL (1) | PL158450B1 (en, 2012) |
PT (1) | PT89035B (en, 2012) |
SE (1) | SE8704542D0 (en, 2012) |
WO (1) | WO1989004825A1 (en, 2012) |
YU (1) | YU46965B (en, 2012) |
ZA (1) | ZA888509B (en, 2012) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE8901570D0 (sv) * | 1989-05-02 | 1989-05-02 | Draco Ab | Organic salts of cysteine derivatives |
WO1990014335A1 (en) * | 1989-05-17 | 1990-11-29 | Aktiebolaget Astra | Process for the n-monoacylation of cysteine |
SE9103572D0 (sv) * | 1991-11-29 | 1991-11-29 | Astra Ab | Organic salts of n,n'-diacetyl cystine |
WO2002013813A1 (en) * | 2000-08-11 | 2002-02-21 | The Lawson Health Research Institute | Compositions and methods for inhibiting islet dysfunction and autoimmune disorders |
EP4426440A1 (en) * | 2021-11-03 | 2024-09-11 | Lankenau Institute for Medical Research | Compositions and methods for assaying glutathione recylcling capacity |
US12350250B2 (en) | 2022-04-01 | 2025-07-08 | The Regent Of The University Of Colorado, A Body Corporate | Aggrelytes for treating ocular conditions |
WO2024243373A1 (en) * | 2023-05-24 | 2024-11-28 | Lento Bio, Inc. | Cysteine derivatives for the treatment of presbyopia |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3091569A (en) * | 1960-08-26 | 1963-05-28 | Mead Johnson & Co | Mucolytic-nu-acylated sulfhydryl compositions and process for treating animal mucus |
GB954268A (en) * | 1962-02-26 | 1964-04-02 | Mead Johnson & Co | Decongestant compositions comprising n-acylated sulphydryl compounds |
FR2470M (fr) * | 1962-03-13 | 1964-04-20 | Mead Johnson & Co | Composition thérapeutique. |
SE312633B (en, 2012) * | 1962-04-26 | 1969-07-21 | Mead Johnson & Co | |
US3184505A (en) * | 1962-06-18 | 1965-05-18 | Mead Johnson & Co | Process for the n-monoacylation of cysteine |
US3242052A (en) * | 1963-08-13 | 1966-03-22 | Mead Johnson & Co | Hair treatment with nu-acylcysteines |
US4093740A (en) * | 1973-02-16 | 1978-06-06 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessier | Fodder for ruminants |
JPS6011888B2 (ja) * | 1978-10-11 | 1985-03-28 | 参天製薬株式会社 | リウマチ疾患治療薬 |
IT1141654B (it) * | 1980-01-31 | 1986-10-08 | Alfa Farmaceutici Spa | Nuovi derivati della cisteina ad attivita' antiinfiammatoria,analgesica,antipiretica e mucolitica |
-
1987
- 1987-11-19 SE SE8704542A patent/SE8704542D0/xx unknown
-
1988
- 1988-11-04 MY MYPI88001267A patent/MY106950A/en unknown
- 1988-11-09 YU YU207888A patent/YU46965B/sh unknown
- 1988-11-09 NZ NZ226898A patent/NZ226898A/en unknown
- 1988-11-10 IL IL88342A patent/IL88342A/xx not_active IP Right Cessation
- 1988-11-14 ZA ZA888509A patent/ZA888509B/xx unknown
- 1988-11-15 IE IE341888A patent/IE61181B1/en not_active IP Right Cessation
- 1988-11-16 DE DE8888850393T patent/DE3873696T2/de not_active Expired - Fee Related
- 1988-11-16 EG EG58988A patent/EG19066A/xx active
- 1988-11-16 AT AT88850393T patent/ATE79371T1/de not_active IP Right Cessation
- 1988-11-16 JP JP63509285A patent/JPH02502189A/ja active Pending
- 1988-11-16 EP EP88850393A patent/EP0317540B1/en not_active Expired - Lifetime
- 1988-11-16 ES ES88850393T patent/ES2051891T3/es not_active Expired - Lifetime
- 1988-11-16 AU AU27292/88A patent/AU615244B2/en not_active Ceased
- 1988-11-16 HU HU886768A patent/HU203224B/hu not_active IP Right Cessation
- 1988-11-16 WO PCT/SE1988/000615 patent/WO1989004825A1/en active IP Right Grant
- 1988-11-17 AR AR88312491A patent/AR245693A1/es active
- 1988-11-17 PL PL1988275851A patent/PL158450B1/pl unknown
- 1988-11-17 DD DD88321910A patent/DD275865A5/de not_active IP Right Cessation
- 1988-11-18 IS IS3413A patent/IS1544B/is unknown
- 1988-11-18 PT PT89035A patent/PT89035B/pt not_active IP Right Cessation
- 1988-11-19 CN CN88108035A patent/CN1033802A/zh active Pending
-
1989
- 1989-07-05 NO NO892787A patent/NO170413C/no unknown
- 1989-07-13 DK DK347789A patent/DK347789D0/da not_active Application Discontinuation
- 1989-07-18 FI FI893478A patent/FI93442C/fi not_active IP Right Cessation
- 1989-07-18 KR KR1019890701345A patent/KR890701553A/ko not_active Ceased
-
1992
- 1992-10-29 GR GR920402436T patent/GR3006115T3/el unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU657827B2 (en) | Organic salts of N, N'-diacetyl cystine | |
US5874468A (en) | Brain targeted low molecular weight hydrophobic antioxidant compounds | |
US4440788A (en) | Cysteine derivatives | |
EP0706512A1 (fr) | Derives d'acetamide et leur utilisation comme modificateurs du comportement de prise alimentaire | |
JPH08511777A (ja) | 二硫化物 | |
JPS62267222A (ja) | 不飽和脂肪酸含有製剤 | |
US20020107176A1 (en) | Brain targeted low molecular weight hydrophobic anti oxidant compounds | |
US5350767A (en) | Derivatives of cysteine | |
HU188058B (en) | Process for preparing chyralic benzyl-mercapto-propionil-amino derivatives | |
JPS56145298A (en) | Aminophenyl derivative and physiologically active preparation containing the same | |
AU615244B2 (en) | New derivatives of cysteine, processes for their preparation and their use | |
US5519054A (en) | Pharmaceutical compositions containing N-acetyl-cysteine derivatives useful for the treatment of cataract | |
PT98121B (pt) | Processo para a preparacao de novos 3,3'-ditio-bis (acidos propionicos) e seus esteres e de composicoes farmaceuticas que os contem | |
FR2493311A1 (fr) | Derives 2,6-c-dimethyltyrosine1-(d-amino-acide)2-(acide e-amino-caproique et acide g-aminobutyrique)5 de la methionine-encephaline, utiles notamment comme analgesiques | |
US8871805B2 (en) | Compound, composition and uses thereof | |
AU2003220894B8 (en) | Kappa-opioid receptor agonist comprising 2-phenylbenzothiazoline derivative | |
EP0475214A1 (en) | Caffeic acid derivatives and pharmaceutical compositions containing the same | |
WO1994002456A1 (en) | Radioimaging and radiochemotherapy phenolic thioether amines and acyl derivatives thereof for use in diagnosing and treating pigmentation disorders | |
RU2168493C2 (ru) | Производные l-аргинина, способ их получения, фармацевтическая композиция, обладающая ингибирующей no-синтазу активностью | |
CH655721A5 (fr) | Derives du furanne et sels d'addition de ces derives leurs procedes de preparation et composition pharmaceutique les contenant. | |
DE69736189T2 (de) | Schwefel enthaltende aminosäurederivate | |
FR2503150A1 (fr) | Mercaptoacyl-carnitines, procede pour leur preparation et leurs utilisations therapeutiques dans le traitement des intoxications et des brulures et en tant qu'agents mucolytiques | |
EP0051682B1 (en) | Cysteine derivatives and process for their preparation | |
US4990534A (en) | Aralkyl esters and processes for their preparation | |
EP0593697A1 (en) | MERCAPTO-ACETAMIDE DERIVATIVES. |