FI80259C - Foerfarande foer framstaellning av terapeutiskt anvaendbara isotiuronium-salter. - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara isotiuronium-salter. Download PDFInfo
- Publication number
- FI80259C FI80259C FI854790A FI854790A FI80259C FI 80259 C FI80259 C FI 80259C FI 854790 A FI854790 A FI 854790A FI 854790 A FI854790 A FI 854790A FI 80259 C FI80259 C FI 80259C
- Authority
- FI
- Finland
- Prior art keywords
- general formula
- compounds
- aminoiminomethyl
- allyl
- isothiuronium
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 83
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- -1 hydroxy, mercapto Chemical group 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 9
- 229940100198 alkylating agent Drugs 0.000 claims description 8
- 239000002168 alkylating agent Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 230000000694 effects Effects 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- 238000012360 testing method Methods 0.000 description 24
- 210000004027 cell Anatomy 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- 206010028980 Neoplasm Diseases 0.000 description 17
- 241001465754 Metazoa Species 0.000 description 15
- 239000013078 crystal Substances 0.000 description 14
- 238000011282 treatment Methods 0.000 description 13
- 230000000259 anti-tumor effect Effects 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 206010003445 Ascites Diseases 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 230000003308 immunostimulating effect Effects 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 210000004881 tumor cell Anatomy 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 239000008187 granular material Substances 0.000 description 10
- PQHJXKOVINDQES-UHFFFAOYSA-N carbonic acid;(e)-hydrazinylmethylidenethiourea Chemical compound OC(O)=O.NN\C=N\C(N)=S PQHJXKOVINDQES-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 210000004698 lymphocyte Anatomy 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 230000005012 migration Effects 0.000 description 8
- 238000013508 migration Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 230000001988 toxicity Effects 0.000 description 8
- 231100000419 toxicity Toxicity 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 210000000987 immune system Anatomy 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- 239000000824 cytostatic agent Substances 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 206010025323 Lymphomas Diseases 0.000 description 4
- 230000010056 antibody-dependent cellular cytotoxicity Effects 0.000 description 4
- 230000004071 biological effect Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 231100000673 dose–response relationship Toxicity 0.000 description 4
- 210000003714 granulocyte Anatomy 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 210000000265 leukocyte Anatomy 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 230000017074 necrotic cell death Effects 0.000 description 4
- 230000003448 neutrophilic effect Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 230000002269 spontaneous effect Effects 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 3
- 208000026310 Breast neoplasm Diseases 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 230000002141 anti-parasite Effects 0.000 description 3
- 239000003096 antiparasitic agent Substances 0.000 description 3
- 230000001472 cytotoxic effect Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 238000001356 surgical procedure Methods 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 2
- 125000005999 2-bromoethyl group Chemical group 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- 241000238876 Acari Species 0.000 description 2
- 229920000936 Agarose Polymers 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- 208000031637 Erythroblastic Acute Leukemia Diseases 0.000 description 2
- 208000036566 Erythroleukaemia Diseases 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 206010027458 Metastases to lung Diseases 0.000 description 2
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 208000021841 acute erythroid leukemia Diseases 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 229960001748 allylthiourea Drugs 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 210000000481 breast Anatomy 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 244000309466 calf Species 0.000 description 2
- TWUUONFGHQPWBB-UHFFFAOYSA-N carbonic acid;(1e)-1-(hydrazinylmethylidene)-3-propan-2-ylthiourea Chemical compound OC(O)=O.CC(C)NC(=S)NC=NN TWUUONFGHQPWBB-UHFFFAOYSA-N 0.000 description 2
- KMPYMDDJOMYIEU-UHFFFAOYSA-N carbonic acid;1-(hydrazinylmethylidene)-3-methylthiourea Chemical compound OC(O)=O.CNC(=S)N=CNN KMPYMDDJOMYIEU-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000030833 cell death Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 230000001085 cytostatic effect Effects 0.000 description 2
- 230000003013 cytotoxicity Effects 0.000 description 2
- 231100000135 cytotoxicity Toxicity 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 210000003743 erythrocyte Anatomy 0.000 description 2
- 230000000004 hemodynamic effect Effects 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 230000001900 immune effect Effects 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000008595 infiltration Effects 0.000 description 2
- 238000001764 infiltration Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 210000002540 macrophage Anatomy 0.000 description 2
- 125000005394 methallyl group Chemical group 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- INDZTCRIYSRWOH-UHFFFAOYSA-N undec-10-enyl carbamimidothioate;hydroiodide Chemical compound I.NC(=N)SCCCCCCCCCC=C INDZTCRIYSRWOH-UHFFFAOYSA-N 0.000 description 2
- 230000002861 ventricular Effects 0.000 description 2
- CGRFDAGBURXLCV-UHFFFAOYSA-N (3e)-1-butyl-3-(hydrazinylmethylidene)thiourea;carbonic acid Chemical compound OC(O)=O.CCCCNC(=S)NC=NN CGRFDAGBURXLCV-UHFFFAOYSA-N 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- TVDCSPSRGSLXOV-UHFFFAOYSA-N 1-bromo-3-chloropropan-2-ol Chemical compound ClCC(O)CBr TVDCSPSRGSLXOV-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- ULIKDJVNUXNQHS-UHFFFAOYSA-N 2-Propene-1-thiol Chemical compound SCC=C ULIKDJVNUXNQHS-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- USEGQJLHQSTGHW-UHFFFAOYSA-N 3-bromo-2-methylprop-1-ene Chemical compound CC(=C)CBr USEGQJLHQSTGHW-UHFFFAOYSA-N 0.000 description 1
- ANKGBEWXYVSQKQ-UHFFFAOYSA-N 3-chloropropyl N'-[(E)-hydrazinylidenemethyl]carbamimidothioate Chemical class N\N=C\N=C(N)SCCCCl ANKGBEWXYVSQKQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- YDZPQDRCDNDFQL-UHFFFAOYSA-N CC(C(NC(=S)N)Cl)O Chemical class CC(C(NC(=S)N)Cl)O YDZPQDRCDNDFQL-UHFFFAOYSA-N 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229940123457 Free radical scavenger Drugs 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 101001093181 Homo sapiens Short coiled-coil protein Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 241001480843 Ixodes ricinus Species 0.000 description 1
- GBKLAYXZNQSPBS-XYSQQLOGSA-N Mannomustine dihydrochloride Chemical compound Cl.Cl.ClCCNC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CNCCCl GBKLAYXZNQSPBS-XYSQQLOGSA-N 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 206010027452 Metastases to bone Diseases 0.000 description 1
- VFKZTMPDYBFSTM-KVTDHHQDSA-N Mitobronitol Chemical compound BrC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CBr VFKZTMPDYBFSTM-KVTDHHQDSA-N 0.000 description 1
- 108091093105 Nuclear DNA Proteins 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 102100036292 Short coiled-coil protein Human genes 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 208000000260 Warts Diseases 0.000 description 1
- QKIGEGSKOLMYBO-UHFFFAOYSA-N [3-chloropropylsulfanyl-(hydrazinylmethylideneamino)methylidene]-propan-2-ylazanium;bromide Chemical compound [Br-].NN/C=N/C(=[NH+]C(C)C)SCCCCl QKIGEGSKOLMYBO-UHFFFAOYSA-N 0.000 description 1
- RAISTJMHQFJKCK-UHFFFAOYSA-N [Br-].NN=CNC(SCCC)=[NH2+] Chemical compound [Br-].NN=CNC(SCCC)=[NH2+] RAISTJMHQFJKCK-UHFFFAOYSA-N 0.000 description 1
- HPKMTWRSCVWPAJ-UHFFFAOYSA-N [amino(2-bromoethylsulfanyl)methylidene]-methanehydrazonoylazanium;bromide Chemical compound [Br-].N\N=C\[NH+]=C(N)SCCBr HPKMTWRSCVWPAJ-UHFFFAOYSA-N 0.000 description 1
- OVMGAEPSTKSJBC-UHFFFAOYSA-N [amino(2-chloroethylsulfanyl)methylidene]-methanehydrazonoylazanium;bromide Chemical compound [Br-].N\N=C\[NH+]=C(N)SCCCl OVMGAEPSTKSJBC-UHFFFAOYSA-N 0.000 description 1
- FNCDWXFRJOMUPU-UHFFFAOYSA-N [amino(2-hydroxyethylsulfanyl)methylidene]-methanehydrazonoylazanium;chloride Chemical compound [Cl-].N\N=C\[NH+]=C(N)SCCO FNCDWXFRJOMUPU-UHFFFAOYSA-N 0.000 description 1
- QYHHXUBXSKNBMM-UHFFFAOYSA-N [amino(3-bromopropylsulfanyl)methylidene]-methanehydrazonoylazanium;bromide Chemical compound [Br-].N\N=C\[NH+]=C(N)SCCCBr QYHHXUBXSKNBMM-UHFFFAOYSA-N 0.000 description 1
- DELBAVAZHVUWIE-UHFFFAOYSA-N [amino(3-chloropropylsulfanyl)methylidene]-methanehydrazonoylazanium;bromide Chemical compound [Br-].N\N=C\[NH+]=C(N)SCCCCl DELBAVAZHVUWIE-UHFFFAOYSA-N 0.000 description 1
- XVOHAPDHTIIEOL-UHFFFAOYSA-N [amino(3-hydroxypropylsulfanyl)methylidene]-methanehydrazonoylazanium;bromide Chemical compound [Br-].N\N=C\[NH+]=C(N)SCCCO XVOHAPDHTIIEOL-UHFFFAOYSA-N 0.000 description 1
- AGPXQWFVAAZXTI-UHFFFAOYSA-N [amino(3-methylbutylsulfanyl)methylidene]-methanehydrazonoylazanium;bromide Chemical compound [Br-].CC(C)CCSC(N)=[NH+]\C=N\N AGPXQWFVAAZXTI-UHFFFAOYSA-N 0.000 description 1
- FASCHSFYAJQHNY-UHFFFAOYSA-N [amino(3-sulfanylpropylsulfanyl)methylidene]-methanehydrazonoylazanium;bromide Chemical compound [Br-].N\N=C\[NH+]=C(N)SCCCS FASCHSFYAJQHNY-UHFFFAOYSA-N 0.000 description 1
- SCJDGNVVSRLVLP-UHFFFAOYSA-N [amino(butylsulfanyl)methylidene]-methanehydrazonoylazanium;bromide Chemical compound [Br-].CCCCSC(N)=[NH+]\C=N\N SCJDGNVVSRLVLP-UHFFFAOYSA-N 0.000 description 1
- SAMLAISPAYGTTR-UHFFFAOYSA-N [amino(prop-2-ynylsulfanyl)methylidene]-[(z)-hydrazinylidenemethyl]azanium;bromide Chemical compound [Br-].N\N=C/[NH+]=C(N)SCC#C SAMLAISPAYGTTR-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000141 anti-hypoxic effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 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
- 239000006227 byproduct Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- BVBWYXDQKWFFFQ-UHFFFAOYSA-N carbonic acid;(1z)-1-(hydrazinylmethylidene)-3-propylthiourea Chemical compound OC(O)=O.CCCNC(=S)NC=NN BVBWYXDQKWFFFQ-UHFFFAOYSA-N 0.000 description 1
- SSQUSLMKNUBPCH-UHFFFAOYSA-N carbonic acid;(3e)-1-cyclohexyl-3-(hydrazinylmethylidene)thiourea Chemical compound OC(O)=O.NN=CNC(=S)NC1CCCCC1 SSQUSLMKNUBPCH-UHFFFAOYSA-N 0.000 description 1
- JQQGUPGSXFENBD-UHFFFAOYSA-N carbonic acid;(3e)-1-ethyl-3-(hydrazinylmethylidene)thiourea Chemical compound OC(O)=O.CCNC(=S)NC=NN JQQGUPGSXFENBD-UHFFFAOYSA-N 0.000 description 1
- 230000003293 cardioprotective effect Effects 0.000 description 1
- 230000005779 cell damage Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 208000037887 cell injury Diseases 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 230000002380 cytological effect Effects 0.000 description 1
- 230000003583 cytomorphological effect Effects 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000005786 degenerative changes Effects 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- OKGXJRGLYVRVNE-UHFFFAOYSA-N diaminomethylidenethiourea Chemical compound NC(N)=NC(N)=S OKGXJRGLYVRVNE-UHFFFAOYSA-N 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 210000000222 eosinocyte Anatomy 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000007760 free radical scavenging Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- RMUFSRMRRDOUHH-UHFFFAOYSA-N hydrazinylmethylidenethiourea Chemical compound NN=CNC(N)=S RMUFSRMRRDOUHH-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000005965 immune activity Effects 0.000 description 1
- 229960001438 immunostimulant agent Drugs 0.000 description 1
- 239000003022 immunostimulating agent Substances 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 208000019420 lymphoid neoplasm Diseases 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 208000037843 metastatic solid tumor Diseases 0.000 description 1
- 210000004088 microvessel Anatomy 0.000 description 1
- 229960005485 mitobronitol Drugs 0.000 description 1
- 239000003226 mitogen Substances 0.000 description 1
- 230000004660 morphological change Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 210000000822 natural killer cell Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 229940045681 other alkylating agent in atc Drugs 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 210000001539 phagocyte Anatomy 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 210000004180 plasmocyte Anatomy 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- LSJJIWWDYYDQEH-UHFFFAOYSA-N propyl N'-[(E)-hydrazinylidenemethyl]carbamimidothioate Chemical class CCCSC(N)=N\C=N\N LSJJIWWDYYDQEH-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004202 respiratory function Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 210000005166 vasculature Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- 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
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (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)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Tropical Medicine & Parasitology (AREA)
- Anesthesiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU132484 | 1984-04-03 | ||
| HU841324A HU196745B (en) | 1984-04-03 | 1984-04-03 | Process for producing n-/amino-imino-methyl/-isothiuronium derivatives with immunostimulant and cytostatic effect |
| HU132485 | 1985-03-19 | ||
| HU132485 | 1985-03-19 | ||
| PCT/HU1985/000022 WO1985004399A1 (en) | 1984-04-03 | 1985-04-02 | Isothiuronium salts |
| HU8500022 | 1985-04-02 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI854790L FI854790L (fi) | 1985-12-03 |
| FI854790A0 FI854790A0 (fi) | 1985-12-03 |
| FI80259B FI80259B (fi) | 1990-01-31 |
| FI80259C true FI80259C (fi) | 1990-05-10 |
Family
ID=26317358
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI854790A FI80259C (fi) | 1984-04-03 | 1985-12-03 | Foerfarande foer framstaellning av terapeutiskt anvaendbara isotiuronium-salter. |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPH0825992B2 (pl) |
| CN (1) | CN1008093B (pl) |
| DE (1) | DE3590133T1 (pl) |
| FI (1) | FI80259C (pl) |
| GB (1) | GB2167750B (pl) |
| IL (1) | IL74743A (pl) |
| NZ (1) | NZ211639A (pl) |
| PL (1) | PL145636B1 (pl) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR788429A (fr) * | 1934-12-14 | 1935-10-10 | Ig Farbenindustrie Ag | Production de combinaisons du guanyle et biguanyle |
| DE2426683A1 (de) * | 1974-06-01 | 1975-12-18 | Boehringer Mannheim Gmbh | Biguanide und verfahren zu deren herstellung |
-
1985
- 1985-03-27 IL IL74743A patent/IL74743A/xx not_active IP Right Cessation
- 1985-03-29 NZ NZ211639A patent/NZ211639A/xx unknown
- 1985-04-02 DE DE19853590133 patent/DE3590133T1/de not_active Withdrawn
- 1985-04-02 JP JP60501619A patent/JPH0825992B2/ja not_active Expired - Lifetime
- 1985-04-02 GB GB08529529A patent/GB2167750B/en not_active Expired
- 1985-04-03 PL PL1985252744A patent/PL145636B1/pl unknown
- 1985-04-24 CN CN85103160A patent/CN1008093B/zh not_active Expired
- 1985-12-03 FI FI854790A patent/FI80259C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB8529529D0 (en) | 1986-01-08 |
| DE3590133T1 (de) | 1986-06-26 |
| PL252744A1 (en) | 1986-08-12 |
| CN85103160A (zh) | 1986-09-17 |
| FI854790L (fi) | 1985-12-03 |
| JPH0825992B2 (ja) | 1996-03-13 |
| FI80259B (fi) | 1990-01-31 |
| FI854790A0 (fi) | 1985-12-03 |
| JPS61501849A (ja) | 1986-08-28 |
| NZ211639A (en) | 1989-03-29 |
| IL74743A (en) | 1992-09-06 |
| CN1008093B (zh) | 1990-05-23 |
| PL145636B1 (en) | 1988-10-31 |
| GB2167750A (en) | 1986-06-04 |
| GB2167750B (en) | 1988-04-27 |
| IL74743A0 (en) | 1985-06-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20020011973A (ko) | 퀴나졸린 및 이의 치료 용도 | |
| US3949089A (en) | Substituted guanidine compounds as antifibrillatory agents | |
| JPH0460987B2 (pl) | ||
| KR840001965B1 (ko) | 안트라센-9,10-비스-카르보닐-히드라존 유도체 제조방법 | |
| EP0094149B1 (en) | Pharmaceutical compositions containing a complex of iron with n-substituted 3-hydroxypyrid-2-one or -4-one derivatives | |
| US4370329A (en) | Piperazine derivatives as circulation-enhancing substances | |
| EP0318330A3 (en) | Glutathione esters for treating ventricular arrhythmia | |
| KR20080004475A (ko) | 표면적으로 양친매성인 중합체 및 올리고머, 그 조성물 및암치료방법으로서의 그 용도 | |
| EP0202673B1 (de) | Cytostatisch wirksame Titanocen-Komplexe | |
| FI80259C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara isotiuronium-salter. | |
| RU2108100C1 (ru) | Иммуномодулятор | |
| KR101191733B1 (ko) | 파골세포 분화 억제 효과를 갖는 신규한 화합물 및 이를 포함하는 약학적 조성물 | |
| CZ321095A3 (en) | Heterocyclic compounds | |
| DE2060968A1 (de) | Neue Thipyrane und Verfahren zu ihrer Herstellung | |
| US6060480A (en) | Preventives/remedies for muscle tissue degenerations | |
| US4710578A (en) | Isothiuronium salts | |
| US7732485B2 (en) | Treatment of cancer | |
| US5091410A (en) | Thioxanthenone antitumor agents | |
| FI75809C (fi) | Foerfarande foer framstaellning av terapeutiskt aktiva vattenloesliga derivat av 6,6'-metylen-bis(2,2,4- trimetyl-1,2-dihydrokinolin). | |
| US3463861A (en) | Compositions and method of treating mycobacterium tuberculosis with 2,2'-(ethylenediimino)-di-1-butanols | |
| US4510147A (en) | Compositions for and medical use of water-soluble derivatives of 6,6-methylene-bis-(2,2,4-trimethyl-1,2-dihydroquinoline) | |
| CN113748119B (zh) | 一种用作iap抑制剂的smac模拟物的结晶及其制备方法 | |
| FI69630C (fi) | Foerfarande foer framstaellning av kvaternaera salter av n,n3-di(beta-brompropionyl)-n1-dispirotripiperazinium vilka salter aer anvaendbara laekemedel mot leukos och tumoerer | |
| RU2021260C1 (ru) | Соли акриловой кислоты, проявляющие цитопротекторную и противоязвенную активность, и состав, обладающий цитопротекторной и противоязвенной активностью | |
| WO1994006781A1 (en) | New compounds for use in the treatment of cancer |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC | Transfer of assignment of patent |
Owner name: THYREOS CORPORATION |
|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: THYREOS CORPORATION |