IL98310A - תכשירים תרופתיים המכילים תולדות של ציסטין - Google Patents
תכשירים תרופתיים המכילים תולדות של ציסטיןInfo
- Publication number
- IL98310A IL98310A IL9831091A IL9831091A IL98310A IL 98310 A IL98310 A IL 98310A IL 9831091 A IL9831091 A IL 9831091A IL 9831091 A IL9831091 A IL 9831091A IL 98310 A IL98310 A IL 98310A
- Authority
- IL
- Israel
- Prior art keywords
- diacetylcystine
- diisovalerylcystine
- dimethyl ester
- preparation
- dibutyrylcystine
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- LEVWYRKDKASIDU-IMJSIDKUSA-N cystine group Chemical class C([C@@H](C(=O)O)N)SSC[C@@H](C(=O)O)N LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 title abstract description 5
- 210000000987 immune system Anatomy 0.000 claims abstract description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract 5
- 239000004480 active ingredient Substances 0.000 claims abstract 4
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
- 230000003287 optical effect Effects 0.000 claims description 21
- 230000000694 effects Effects 0.000 claims description 18
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 12
- 206010006451 bronchitis Diseases 0.000 claims description 12
- 208000007451 chronic bronchitis Diseases 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 229960003067 cystine Drugs 0.000 claims description 5
- 230000002519 immonomodulatory effect Effects 0.000 claims description 5
- 208000030507 AIDS Diseases 0.000 claims description 4
- 208000031886 HIV Infections Diseases 0.000 claims description 4
- 239000004158 L-cystine Substances 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 230000003143 atherosclerotic effect Effects 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 230000003211 malignant effect Effects 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 206010039083 rhinitis Diseases 0.000 claims description 3
- 208000037357 HIV infectious disease Diseases 0.000 claims description 2
- 230000007547 defect Effects 0.000 claims description 2
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- CVBVDRNGIPXSLU-RYUDHWBXSA-N (2r)-3-[[(2r)-2-carboxy-2-(3-methylbutanoylamino)ethyl]disulfanyl]-2-(3-methylbutanoylamino)propanoic acid Chemical compound CC(C)CC(=O)N[C@H](C(O)=O)CSSC[C@@H](C(O)=O)NC(=O)CC(C)C CVBVDRNGIPXSLU-RYUDHWBXSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- GLVKJHZBJORHTM-KBPBESRZSA-N methyl (2r)-3-[[(2r)-3-methoxy-2-(3-methylbutanoylamino)-3-oxopropyl]disulfanyl]-2-(3-methylbutanoylamino)propanoate Chemical compound CC(C)CC(=O)N[C@H](C(=O)OC)CSSC[C@H](NC(=O)CC(C)C)C(=O)OC GLVKJHZBJORHTM-KBPBESRZSA-N 0.000 claims 1
- 230000000638 stimulation Effects 0.000 abstract 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 11
- 239000013543 active substance Substances 0.000 description 11
- 229960004308 acetylcysteine Drugs 0.000 description 8
- 241000042812 Divales Species 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 206010053613 Type IV hypersensitivity reaction Diseases 0.000 description 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 6
- 230000005951 type IV hypersensitivity Effects 0.000 description 6
- 208000027930 type IV hypersensitivity disease Diseases 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 230000005713 exacerbation Effects 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YTPQSLLEROSACP-UHFFFAOYSA-N 2-acetamido-3-[(2-acetamido-2-carboxyethyl)disulfanyl]propanoic acid Chemical compound CC(=O)NC(C(O)=O)CSSCC(C(O)=O)NC(C)=O YTPQSLLEROSACP-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 235000010980 cellulose Nutrition 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 210000000038 chest Anatomy 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 208000000884 Airway Obstruction Diseases 0.000 description 2
- 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 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 208000019693 Lung disease Diseases 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 239000003022 immunostimulating agent Substances 0.000 description 2
- 230000003308 immunostimulating effect Effects 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- 210000000115 thoracic cavity Anatomy 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 231100000027 toxicology Toxicity 0.000 description 2
- IEXQFIQEVJTLIE-ROUUACIJSA-N (2r)-3-[[(2r)-2-carboxy-2-(octanoylamino)ethyl]disulfanyl]-2-(octanoylamino)propanoic acid Chemical compound CCCCCCCC(=O)N[C@H](C(O)=O)CSSC[C@@H](C(O)=O)NC(=O)CCCCCCC IEXQFIQEVJTLIE-ROUUACIJSA-N 0.000 description 1
- SJHPCNCNNSSLPL-NTMALXAHSA-N (4z)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)/N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-NTMALXAHSA-N 0.000 description 1
- KYNFOMQIXZUKRK-UHFFFAOYSA-N 2,2'-dithiodiethanol Chemical compound OCCSSCCO KYNFOMQIXZUKRK-UHFFFAOYSA-N 0.000 description 1
- AVPDLWTUGIZJLH-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C([O-])=O.C[NH+](C)CCOC(=O)C(C)=C AVPDLWTUGIZJLH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241001222157 Amblyospora stimuli Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- GUBGYTABKSRVRQ-DCSYEGIMSA-N Beta-Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-DCSYEGIMSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000819038 Chichester Species 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-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
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 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 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 235000019393 L-cystine Nutrition 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 240000001307 Myosotis scorpioides Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 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 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 210000001132 alveolar macrophage Anatomy 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011575 calcium Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- 229940116901 diethyldithiocarbamate Drugs 0.000 description 1
- LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 description 1
- 238000007907 direct compression Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229960002737 fructose Drugs 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229960001031 glucose Drugs 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229960001438 immunostimulant agent Drugs 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229960001375 lactose Drugs 0.000 description 1
- 229940041476 lactose 100 mg Drugs 0.000 description 1
- 150000002617 leukotrienes Chemical class 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000011777 magnesium Chemical class 0.000 description 1
- 229910052749 magnesium Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- UGIXRMQUIDKQCU-ZETCQYMHSA-N methyl (2r)-2-(3-methylbutanoylamino)-3-sulfanylpropanoate Chemical compound COC(=O)[C@H](CS)NC(=O)CC(C)C UGIXRMQUIDKQCU-ZETCQYMHSA-N 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 230000000510 mucolytic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 229940100688 oral solution Drugs 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000006025 oxidative dimerization reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000011591 potassium Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000000644 propagated effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- GYTROFMCUJZKNA-UHFFFAOYSA-N triethyl triethoxysilyl silicate Chemical compound CCO[Si](OCC)(OCC)O[Si](OCC)(OCC)OCC GYTROFMCUJZKNA-UHFFFAOYSA-N 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/225—Polycarboxylic acids
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- 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
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- 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
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Emergency Medicine (AREA)
- Pulmonology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Virology (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Oncology (AREA)
- Physical Education & Sports Medicine (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Communicable Diseases (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Tropical Medicine & Parasitology (AREA)
- Heart & Thoracic Surgery (AREA)
- Otolaryngology (AREA)
- Urology & Nephrology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9002067A SE9002067D0 (sv) | 1990-06-08 | 1990-06-08 | The pharmacological use of certain cystine derivatives |
| SE9002275A SE9002275D0 (sv) | 1990-06-28 | 1990-06-28 | Novel 3,3'-dithiobis(propionic acids) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL98310A0 IL98310A0 (en) | 1992-06-21 |
| IL98310A true IL98310A (he) | 1996-08-04 |
Family
ID=26660796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9831091A IL98310A (he) | 1990-06-08 | 1991-05-30 | תכשירים תרופתיים המכילים תולדות של ציסטין |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US5441976A (he) |
| EP (1) | EP0532595B1 (he) |
| JP (1) | JP3204320B2 (he) |
| KR (1) | KR100236253B1 (he) |
| AT (1) | ATE144705T1 (he) |
| AU (1) | AU652946B2 (he) |
| CA (1) | CA2083274C (he) |
| DE (1) | DE69122961T2 (he) |
| DK (1) | DK0532595T3 (he) |
| HK (1) | HK62597A (he) |
| HU (1) | HU215920B (he) |
| IE (1) | IE80754B1 (he) |
| IL (1) | IL98310A (he) |
| LV (2) | LV10186B (he) |
| NO (1) | NO924723D0 (he) |
| NZ (1) | NZ247658A (he) |
| PT (1) | PT97905B (he) |
| RU (1) | RU2119793C1 (he) |
| SG (1) | SG49736A1 (he) |
| WO (1) | WO1991018594A1 (he) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9018994D0 (en) * | 1990-08-31 | 1990-10-17 | Secr Defence | Toxic agent protective compounds |
| US5889050A (en) * | 1991-06-21 | 1999-03-30 | Astra Aktiebolag | 3,3'-dithiobis (propionic acids) and esters thereof |
| SE9103572D0 (sv) * | 1991-11-29 | 1991-11-29 | Astra Ab | Organic salts of n,n'-diacetyl cystine |
| JP2947044B2 (ja) * | 1993-01-27 | 1999-09-13 | 味の素株式会社 | 免疫不全症候群治療の補助療法剤 |
| DE4329857C2 (de) * | 1993-09-03 | 1995-08-24 | Deutsches Krebsforsch | Verbindung zur Stärkung des Immunsystems und von Immunreaktionen |
| SE9500897D0 (sv) * | 1995-03-14 | 1995-03-14 | Astra Ab | The pharmacological use of certain cystine derivatives |
| SE9501067D0 (sv) * | 1995-03-24 | 1995-03-24 | Astra Ab | New peptides |
| SE9602262D0 (sv) * | 1996-06-06 | 1996-06-06 | Astra Ab | New use of derivatives of cystine |
| US20030203006A1 (en) * | 1997-10-29 | 2003-10-30 | Ajinomoto Co. Inc. | Immunomodulator |
| US6197749B1 (en) * | 1997-10-29 | 2001-03-06 | Ajinomoto Co., Inc. | Method of suppressing immune responses by reducing intracellular content of glutathione in macrophages and monocytes |
| WO2000021925A1 (fr) * | 1998-10-09 | 2000-04-20 | Ajinomoto Co., Inc. | Derives de la cysteine |
| EP1004302A3 (en) * | 1998-10-29 | 2003-06-04 | Ajinomoto Co., Inc. | Immunomodulator |
| SE9900438D0 (sv) * | 1999-02-10 | 1999-02-10 | Astra Ab | The pharmacological use of certian cystine derivatives |
| JP3988014B2 (ja) * | 2000-02-02 | 2007-10-10 | 味の素株式会社 | ウイルス感染症予防剤 |
| EP1920763B2 (en) | 2000-11-30 | 2022-06-15 | Vectura Limited | Pharmaceutical compositions for inhalation |
| SE518784C2 (sv) * | 2000-12-27 | 2002-11-19 | Nactilus Ab | "N-Acetyl-L-cystein med kompositioner för behandling av neoplasier" |
| US8530509B2 (en) | 2003-06-20 | 2013-09-10 | Siga Technologies, Inc. | Compounds, compositions and methods for treatment and prevention of orthopoxvirus infections and associated diseases |
| DE102004043055B4 (de) | 2004-09-06 | 2009-04-02 | Siemens Ag | Führungsvorrichtung zur Führung eines bewegbaren Maschinenelementes einer Maschine |
| CA2665210A1 (en) * | 2006-10-03 | 2008-06-05 | Galleon Pharmaceuticals, Inc. | S-nitrosothiol compounds and related derivatives |
| MX348481B (es) * | 2007-04-23 | 2017-06-15 | Siga Tech Inc | Productos quimicos, composiciones y metodos para tratamiento y prevencion de infecciones de virus orthopox y enfermedades asociadas. |
| US7829709B1 (en) | 2007-08-10 | 2010-11-09 | Marquette University | Cysteine prodrugs to treat schizophrenia and drug addiction |
| EP2252596B1 (en) * | 2008-02-07 | 2016-12-28 | Marquette University | Cysteine and cystine prodrugs to treat schizophrenia and reduce drug cravings |
| WO2015163488A1 (en) | 2014-04-25 | 2015-10-29 | Ajinomoto Co., Inc. | Immunostimulating agent |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR8205M (he) * | 1968-12-20 | 1970-09-14 | ||
| US3878305A (en) * | 1972-05-25 | 1975-04-15 | Procter & Gamble | Fortification of foodstuffs with n-acyl derivatives of sulphur-containing l-amino acids |
| US3952115A (en) * | 1975-04-02 | 1976-04-20 | The Procter & Gamble Company | Fortification of foodstuffs with N-acyl derivatives of sulfur-containing L-amino acid esters |
| GB2097256B (en) * | 1981-04-02 | 1985-05-30 | Morelle Jean V | Compositions containing n-butyryl alphaaminoacids |
| FR2503151A1 (fr) * | 1981-04-02 | 1982-10-08 | Morelle Jean | Butyryminoacides soufres. mode de preparation. emploi comme element keratogenique chez l'homme et l'animal et comme agent de fertilisation chez les vegetaux |
| US4708965A (en) * | 1985-09-16 | 1987-11-24 | Morgan Lee R | Method of treating herpes virus infections with N,N'-diacetylcystine and derivatives |
| US4724239A (en) * | 1985-09-16 | 1988-02-09 | Morgan Lee R | Method of treating chemical ulcers with N,N'-diacetylcystine, N-acetyl homocysteine and N-acetyl cysteine |
| US4827016A (en) * | 1985-09-16 | 1989-05-02 | Morgan Lee R | Method and compounds for reducing dermal inflammations |
| IT1249650B (it) * | 1991-05-29 | 1995-03-09 | Poli Ind Chimica Spa | N-(5-tioxo-l-prolil)-l-cisteina e suoi derivati, loro preparazione ed impiego terapeutico |
-
1991
- 1991-05-30 IL IL9831091A patent/IL98310A/he not_active IP Right Cessation
- 1991-06-03 DE DE69122961T patent/DE69122961T2/de not_active Expired - Fee Related
- 1991-06-03 JP JP51096391A patent/JP3204320B2/ja not_active Expired - Fee Related
- 1991-06-03 HU HU9203871A patent/HU215920B/hu not_active IP Right Cessation
- 1991-06-03 DK DK91910813.4T patent/DK0532595T3/da active
- 1991-06-03 AU AU80941/91A patent/AU652946B2/en not_active Ceased
- 1991-06-03 RU RU92016463A patent/RU2119793C1/ru not_active IP Right Cessation
- 1991-06-03 SG SG1996004501A patent/SG49736A1/en unknown
- 1991-06-03 WO PCT/SE1991/000388 patent/WO1991018594A1/en active IP Right Grant
- 1991-06-03 EP EP91910813A patent/EP0532595B1/en not_active Expired - Lifetime
- 1991-06-03 AT AT91910813T patent/ATE144705T1/de not_active IP Right Cessation
- 1991-06-03 CA CA002083274A patent/CA2083274C/en not_active Expired - Fee Related
- 1991-06-03 KR KR1019920703125A patent/KR100236253B1/ko not_active IP Right Cessation
- 1991-06-07 PT PT97905A patent/PT97905B/pt not_active IP Right Cessation
- 1991-06-07 IE IE194591A patent/IE80754B1/en not_active IP Right Cessation
-
1992
- 1992-12-04 US US07/949,648 patent/US5441976A/en not_active Expired - Lifetime
- 1992-12-07 NO NO924723A patent/NO924723D0/no unknown
-
1993
- 1993-05-20 NZ NZ247658A patent/NZ247658A/en unknown
- 1993-08-06 LV LVP-93-1017A patent/LV10186B/en unknown
-
1995
- 1995-06-01 US US08/457,004 patent/US5780508A/en not_active Expired - Fee Related
-
1997
- 1997-05-08 HK HK62597A patent/HK62597A/xx not_active IP Right Cessation
- 1997-10-30 LV LVP-97-219A patent/LV11985B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69122961T2 (de) | 1997-03-13 |
| KR100236253B1 (ko) | 1999-12-15 |
| DK0532595T3 (da) | 1997-04-07 |
| HU215920B (hu) | 1999-03-29 |
| PT97905B (pt) | 1998-10-30 |
| IE911945A1 (en) | 1991-12-18 |
| WO1991018594A1 (en) | 1991-12-12 |
| SG49736A1 (en) | 1998-06-15 |
| IL98310A0 (en) | 1992-06-21 |
| CA2083274C (en) | 2002-05-28 |
| NO924723L (no) | 1992-12-07 |
| US5441976A (en) | 1995-08-15 |
| JP3204320B2 (ja) | 2001-09-04 |
| AU8094191A (en) | 1991-12-31 |
| EP0532595A1 (en) | 1993-03-24 |
| LV11985A (lv) | 1998-03-20 |
| LV10186A (lv) | 1994-10-20 |
| HU9203871D0 (en) | 1993-03-29 |
| AU652946B2 (en) | 1994-09-15 |
| IE80754B1 (en) | 1999-01-13 |
| LV10186B (en) | 1995-08-20 |
| CA2083274A1 (en) | 1991-12-09 |
| ATE144705T1 (de) | 1996-11-15 |
| PT97905A (pt) | 1992-03-31 |
| NZ247658A (en) | 2000-07-28 |
| US5780508A (en) | 1998-07-14 |
| RU2119793C1 (ru) | 1998-10-10 |
| DE69122961D1 (de) | 1996-12-05 |
| LV11985B (en) | 1998-06-20 |
| NO924723D0 (no) | 1992-12-07 |
| HK62597A (en) | 1997-05-16 |
| EP0532595B1 (en) | 1996-10-30 |
| HUT70055A (en) | 1995-09-28 |
| JPH05507705A (ja) | 1993-11-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5441976A (en) | Pharmacological use of certain cystine derivatives | |
| AP350A (en) | Organic salts of N,N-Diacetyl cystine. | |
| DE3907649A1 (de) | Arzneimittel, geeignet bei der bekaempfung von viren und der immunstimulierung | |
| CZ279343B6 (cs) | Nové kyseliny 3,3` -dithiobis(propionové) a jejich estery | |
| EP0727207A1 (en) | The pharmacological use of certain cystine derivatives | |
| NZ238306A (en) | Pharmaceutical compositions containing certain cystine derivatives. | |
| CA2193396A1 (en) | A pharmaceutical composition for the prevention and/or treatment of viral infections and optionally inflammations as well as a method for the treatment thereof | |
| US5889050A (en) | 3,3'-dithiobis (propionic acids) and esters thereof | |
| IE61181B1 (en) | New derivatives of cysteine | |
| DE69905144T2 (de) | N,N'-Diacylthiocystine | |
| AU2008200720B2 (en) | Geranyl compounds | |
| LT3976B (en) | Novel 3,3'-dithiobis(propionic acids) and esthers thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| HC | Change of name of proprietor(s) | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |