NL8520077A - Isothiuroniumzouten. - Google Patents

Isothiuroniumzouten. Download PDF

Info

Publication number: NL8520077A
Authority: NL; Netherlands
Prior art keywords: aminoiminomethyl; formula; salt; salts; compound
Prior art date: 1984-04-03

Application number

NL8520077A

Other languages

English (en)

Dutch (nl)

Original Assignee

Peremartoni Vegyipari Vallalat

Priority date (The priority date 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 date listed.)

1984-04-03

Filing date

1985-04-02

Publication date

1986-02-03

1985-04-02 Application filed by Peremartoni Vegyipari Vallalat filed Critical Peremartoni Vegyipari Vallalat

1986-02-03 Publication of NL8520077A publication Critical patent/NL8520077A/nl

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UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims description 106
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 24
-1 N-aminoiminomethyl-S- (2-chloroethyl) -isothiuronium halide Chemical class 0.000 claims description 20
238000000034 method Methods 0.000 claims description 18
239000004480 active ingredient Substances 0.000 claims description 16
239000000825 pharmaceutical preparation Substances 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 12
125000000753 cycloalkyl group Chemical group 0.000 claims description 12
230000003308 immunostimulating effect Effects 0.000 claims description 11
125000003342 alkenyl group Chemical group 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
125000000304 alkynyl group Chemical group 0.000 claims description 9
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
229940100198 alkylating agent Drugs 0.000 claims description 8
239000002168 alkylating agent Substances 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
125000003710 aryl alkyl group Chemical group 0.000 claims description 7
230000001085 cytostatic effect Effects 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
150000001449 anionic compounds Chemical class 0.000 claims description 5
150000002891 organic anions Chemical class 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 5
HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 claims description 4
239000012458 free base Substances 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
LSJJIWWDYYDQEH-UHFFFAOYSA-N propyl N'-[(E)-hydrazinylidenemethyl]carbamimidothioate Chemical class CCCSC(N)=N\C=N\N LSJJIWWDYYDQEH-UHFFFAOYSA-N 0.000 claims description 3
239000000376 reactant Substances 0.000 claims description 3
AJPJVJJWMMOHRW-UHFFFAOYSA-N 2-hydroxyethyl N'-[(E)-hydrazinylidenemethyl]carbamimidothioate Chemical class N\N=C\N=C(N)SCCO AJPJVJJWMMOHRW-UHFFFAOYSA-N 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
RYNFMSTXOVSICL-UHFFFAOYSA-N methyl N'-[(E)-hydrazinylidenemethyl]carbamimidothioate Chemical class CSC(N)=N\C=N\N RYNFMSTXOVSICL-UHFFFAOYSA-N 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
VQJRHVDJBQBBHU-UHFFFAOYSA-N oxiran-2-ylmethyl N'-[(E)-hydrazinylidenemethyl]carbamimidothioate Chemical class N\N=C\N=C(N)SCC1CO1 VQJRHVDJBQBBHU-UHFFFAOYSA-N 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims 1
BKNASEOAKDDNFJ-UHFFFAOYSA-N ethyl N'-(aminomethyl)carbamimidothioate Chemical class CCS\C(N)=N\CN BKNASEOAKDDNFJ-UHFFFAOYSA-N 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
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125000005500 uronium group Chemical group 0.000 claims 1
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OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 4
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
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125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
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IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 2
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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
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
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
UIVRRYMEZLKNGB-UHFFFAOYSA-N [amino(benzylsulfanyl)methylidene]-methanehydrazonoylazanium;chloride Chemical compound [Cl-].N\N=C\[NH+]=C(N)SCC1=CC=CC=C1 UIVRRYMEZLKNGB-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
RUMGGIDISFRZMI-UHFFFAOYSA-N [amino(ethylsulfanyl)methylidene]-methanehydrazonoylazanium;bromide Chemical compound [Br-].CCSC(N)=[NH+]\C=N\N RUMGGIDISFRZMI-UHFFFAOYSA-N 0.000 description 1
BASCCKRWBUNXPI-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]-methanehydrazonoylazanium;iodide Chemical compound [I-].CSC(N)=[NH+]\C=N\N BASCCKRWBUNXPI-UHFFFAOYSA-N 0.000 description 1
BCXJAXMBHQJZTI-UHFFFAOYSA-N [amino(oxiran-2-ylmethylsulfanyl)methylidene]-methanehydrazonoylazanium;bromide Chemical compound [Br-].N\N=C\[NH+]=C(N)SCC1CO1 BCXJAXMBHQJZTI-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
NCMXBLMDSUQNGF-UHFFFAOYSA-N [amino(propan-2-ylsulfanyl)methylidene]-methanehydrazonoylazanium;bromide Chemical compound [Br-].CC(C)SC(N)=[NH+]\C=N\N NCMXBLMDSUQNGF-UHFFFAOYSA-N 0.000 description 1
NWEYTQZMKPSNFI-UHFFFAOYSA-N [amino-(1-chloro-2-hydroxypropyl)sulfanylmethylidene]-methanehydrazonoylazanium;bromide Chemical compound [Br-].CC(O)C(Cl)SC(N)=[NH+]\C=N\N NWEYTQZMKPSNFI-UHFFFAOYSA-N 0.000 description 1
NTGZUHACFONODY-UHFFFAOYSA-N [benzylsulfanyl-(hydrazinylmethylideneamino)methylidene]-cyclohexylazanium;chloride Chemical compound [Cl-].C1CCCCC1[NH+]=C(/N=C/NN)SCC1=CC=CC=C1 NTGZUHACFONODY-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
208000021841 acute erythroid leukemia Diseases 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000001450 anions Chemical group 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
239000003096 antiparasitic agent Substances 0.000 description 1
239000002956 ash Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
230000031018 biological processes and functions Effects 0.000 description 1
210000000625 blastula Anatomy 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
210000000988 bone and bone Anatomy 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
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
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
239000006285 cell suspension Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
210000000038 chest Anatomy 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
239000006071 cream 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
FOMREUVLMSHRCA-UHFFFAOYSA-N cyclohexyl-[(hydrazinylmethylideneamino)-(oxiran-2-ylmethylsulfanyl)methylidene]azanium;bromide Chemical compound [Br-].C1CCCCC1[NH+]=C(/N=C/NN)SCC1CO1 FOMREUVLMSHRCA-UHFFFAOYSA-N 0.000 description 1
APIVAYPDSWABHH-UHFFFAOYSA-N cyclohexyl-[(hydrazinylmethylideneamino)-propylsulfanylmethylidene]azanium;bromide Chemical compound [Br-].CCCSC(\N=C\NN)=[NH+]C1CCCCC1 APIVAYPDSWABHH-UHFFFAOYSA-N 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
230000002380 cytological effect Effects 0.000 description 1
230000003583 cytomorphological effect Effects 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000002950 deficient Effects 0.000 description 1
230000007850 degeneration Effects 0.000 description 1
230000005786 degenerative changes Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000011161 development Methods 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
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000012636 effector Substances 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000001914 filtration 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
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
230000001435 haemodynamic effect Effects 0.000 description 1
125000004969 haloethyl group Chemical group 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
230000035876 healing Effects 0.000 description 1
230000036541 health Effects 0.000 description 1
230000000004 hemodynamic effect Effects 0.000 description 1
210000004276 hyalin Anatomy 0.000 description 1
RMUFSRMRRDOUHH-UHFFFAOYSA-N hydrazinylmethylidenethiourea Chemical compound NN=CNC(N)=S RMUFSRMRRDOUHH-UHFFFAOYSA-N 0.000 description 1
230000003053 immunization Effects 0.000 description 1
238000002649 immunization Methods 0.000 description 1
229960001438 immunostimulant agent Drugs 0.000 description 1
239000003022 immunostimulating agent Substances 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
208000015181 infectious disease Diseases 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
229910001412 inorganic anion Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([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
230000005923 long-lasting effect Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
208000037843 metastatic solid tumor Diseases 0.000 description 1
229960005485 mitobronitol Drugs 0.000 description 1
239000003226 mitogen Substances 0.000 description 1
VFKZTMPDYBFSTM-GUCUJZIJSA-N mitolactol Chemical compound BrC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CBr VFKZTMPDYBFSTM-GUCUJZIJSA-N 0.000 description 1
229950010913 mitolactol Drugs 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000002950 monocyclic group Chemical group 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
125000001624 naphthyl group Chemical group 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
235000019645 odor Nutrition 0.000 description 1
239000011022 opal Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
229940045681 other alkylating agent in atc Drugs 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
239000003182 parenteral nutrition solution Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
210000001539 phagocyte Anatomy 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
230000001885 phytohemagglutinin Effects 0.000 description 1
230000036470 plasma concentration Effects 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
230000005855 radiation Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000009877 rendering Methods 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
230000004202 respiratory function Effects 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
230000036387 respiratory rate Effects 0.000 description 1
230000004044 response Effects 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
238000007619 statistical method Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
229940104230 thymidine Drugs 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
230000009466 transformation Effects 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
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 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
229940045997 vitamin a Drugs 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
- C07D303/34—Compounds containing oxirane rings with hydrocarbon radicals, substituted by sulphur, selenium or tellurium atoms
- 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Cardiology (AREA)
Tropical Medicine & Parasitology (AREA)
Heart & Thoracic Surgery (AREA)
Anesthesiology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NL8520077A 1984-04-03 1985-04-02 Isothiuroniumzouten. NL8520077A (nl)

Applications Claiming Priority (4)

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
PCT/HU1985/000022 WO1985004399A1 (en)	1984-04-03	1985-04-02	Isothiuronium salts
HU8500022		1985-04-02

Publications (1)

Publication Number	Publication Date
NL8520077A true NL8520077A (nl)	1986-02-03

Family

ID=10953931

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8520077A NL8520077A (nl)	1984-04-03	1985-04-02	Isothiuroniumzouten.

Country Status (10)

Country	Link
US (1)	US4710578A (de)
EP (1)	EP0176546B1 (de)
AT (1)	AT386409B (de)
AU (1)	AU604632B2 (de)
CA (1)	CA1301770C (de)
CH (1)	CH666024A5 (de)
HU (1)	HU196745B (de)
NL (1)	NL8520077A (de)
SU (1)	SU1498384A3 (de)
WO (1)	WO1985004399A1 (de)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
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
US3880560A (en) *	1973-06-19	1975-04-29	Takahashi Seiki Co Ltd	Molding machine for synthetic resin article
DE2426683A1 (de) *	1974-06-01	1975-12-18	Boehringer Mannheim Gmbh	Biguanide und verfahren zu deren herstellung

1984
- 1984-04-03 HU HU841324A patent/HU196745B/hu not_active IP Right Cessation
1985
- 1985-04-02 NL NL8520077A patent/NL8520077A/nl unknown
- 1985-04-02 CA CA000478127A patent/CA1301770C/en not_active Expired - Lifetime
- 1985-04-02 CH CH5171/85A patent/CH666024A5/fr not_active IP Right Cessation
- 1985-04-02 US US06/809,888 patent/US4710578A/en not_active Expired - Fee Related
- 1985-04-02 EP EP85901545A patent/EP0176546B1/de not_active Expired
- 1985-04-02 WO PCT/HU1985/000022 patent/WO1985004399A1/en not_active Ceased
- 1985-04-02 AT AT0901085A patent/AT386409B/de not_active IP Right Cessation
- 1985-04-02 AU AU42136/85A patent/AU604632B2/en not_active Ceased
- 1985-11-29 SU SU853990052A patent/SU1498384A3/ru active

Also Published As

Publication number	Publication date
EP0176546A1 (de)	1986-04-09
EP0176546B1 (de)	1988-03-02
AU604632B2 (en)	1991-01-03
AT386409B (de)	1988-08-25
HU196745B (en)	1989-01-30
US4710578A (en)	1987-12-01
ATA901085A (de)	1988-01-15
CH666024A5 (fr)	1988-06-30
HUT37749A (en)	1986-02-28
SU1498384A3 (ru)	1989-07-30
WO1985004399A1 (en)	1985-10-10
AU4213685A (en)	1985-11-01
CA1301770C (en)	1992-05-26

Publication	Publication Date	Title
JP2945360B2 (ja)	1999-09-06	抗腫瘍性、抗ウイルス性、抗レトロウイルス性および殺虫性スペルミン誘導体
JPS61118394A (ja)	1986-06-05	ガラクトース‐ｃ‐６ナイトロジエンマスタード化合物およびその用途
NL8403353A (nl)	1985-06-17	Nieuwe 6-vinyl-furo-(3,4-c)-pyridinederivaten, hun bereiding en farmaceutische preparaten die ze bevatten.
Zin et al.	2022	Cytotoxicity of asymmetric mononuclear silver (I)-N-heterocyclic carbene complexes against human cervical cancer: Synthesis, crystal structure, DFT calculations and effect of substituents
EP0138558A2 (de)	1985-04-24	Phospholipide und ihre Herstellung und Verwendung
KR860001865B1 (ko)	1986-10-24	2'-데옥시-5-치환 우리딘 유도체의 제조방법
EP4238571A1 (de)	2023-09-06	Verwendung von thymidin-derivaten in der herstellung von arzneimitteln
US6160167A (en)	2000-12-12	Mercaptans and disulfides
KR101975299B1 (ko)	2019-05-07	인돌아세트산의 코어구조를 함유하는 화합물 및 그의 용도
NL8520077A (nl)	1986-02-03	Isothiuroniumzouten.
DE2109331A1 (de)	1971-09-02	1 Oxybenzimidazole
KR880001716B1 (ko)	1988-09-08	무기산의 치환된 티아졸리디닐 에스테르의 제조방법
US4293700A (en)	1981-10-06	2,6-Dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid esters and method for preparing same
EP0011747B1 (de)	1982-05-19	Aminopropanolderivate des 6-Hydroxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-ons, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen
DE69815380T2 (de)	2004-05-13	N,n'-bis (sulfonyl) hydrazine die als antineoplastische mittel nützlich sind
FI80259C (fi)	1990-05-10	Foerfarande foer framstaellning av terapeutiskt anvaendbara isotiuronium-salter.
JPH05501103A (ja)	1993-03-04	ビス―アシルオキシメチル誘導体
JPS62919B2 (de)	1987-01-10
US5091410A (en)	1992-02-25	Thioxanthenone antitumor agents
US3717623A (en)	1973-02-20	Sulfanilyl phenyl urea complexes useful against marek's disease
WO2006034327A1 (en)	2006-03-30	Medicinal disulfide salts
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