JPH0825992B2 - イソチウロニウム塩 - Google Patents

イソチウロニウム塩

Info

Publication number: JPH0825992B2
Authority: JP; Japan
Prior art keywords: aminoiminomethyl; salt; isothiuronium; compound; formula
Prior art date: 1984-04-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP60501619A

Other languages

English (en)

Japanese (ja)

Other versions

JPS61501849A (ja

Inventor

ベルテシ，クサバ

モルナル，アツテイラ

ラヨスグクゾギイ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

SAIRIOSU CORP

Original Assignee

SAIRIOSU CORP

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

1996-03-13

1984-04-03 Priority claimed from HU841324A external-priority patent/HU196745B/hu

1985-04-02 Application filed by SAIRIOSU CORP filed Critical SAIRIOSU CORP

1986-08-28 Publication of JPS61501849A publication Critical patent/JPS61501849A/ja

1996-03-13 Publication of JPH0825992B2 publication Critical patent/JPH0825992B2/ja

2011-03-13 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 title claims description 9
150000001875 compounds Chemical class 0.000 claims description 100
239000000203 mixture Substances 0.000 claims description 25
239000004480 active ingredient Substances 0.000 claims description 24
-1 hydroxy, mercapto Chemical class 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 23
238000000034 method Methods 0.000 claims description 20
239000008194 pharmaceutical composition Substances 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 16
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
230000003308 immunostimulating effect Effects 0.000 claims description 11
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 9
229940100198 alkylating agent Drugs 0.000 claims description 7
239000002168 alkylating agent Substances 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
150000001449 anionic compounds Chemical class 0.000 claims description 6
229910001412 inorganic anion Inorganic materials 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 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 4
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 claims description 3
239000012458 free base Substances 0.000 claims description 3
RYNFMSTXOVSICL-UHFFFAOYSA-N methyl N'-[(E)-hydrazinylidenemethyl]carbamimidothioate Chemical class CSC(N)=N\C=N\N RYNFMSTXOVSICL-UHFFFAOYSA-N 0.000 claims description 3
239000000546 pharmaceutical excipient 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
XMNDURLIDGHVAB-UHFFFAOYSA-N (1-chloro-2-hydroxypropyl) N'-[(E)-hydrazinylidenemethyl]carbamimidothioate Chemical class CC(O)C(Cl)SC(N)=N\C=N\N XMNDURLIDGHVAB-UHFFFAOYSA-N 0.000 claims description 2
UHBMCLKMNFOVHK-UHFFFAOYSA-N 2-chloroethyl N'-[(E)-hydrazinylidenemethyl]carbamimidothioate Chemical class N\N=C\N=C(N)SCCCl UHBMCLKMNFOVHK-UHFFFAOYSA-N 0.000 claims description 2
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
ANKGBEWXYVSQKQ-UHFFFAOYSA-N 3-chloropropyl N'-[(E)-hydrazinylidenemethyl]carbamimidothioate Chemical class N\N=C\N=C(N)SCCCCl ANKGBEWXYVSQKQ-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
150000001298 alcohols Chemical class 0.000 claims description 2
150000001350 alkyl halides Chemical class 0.000 claims description 2
150000002170 ethers Chemical class 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
125000000962 organic group Chemical group 0.000 claims 3
239000003937 drug carrier Substances 0.000 claims 2
BKNASEOAKDDNFJ-UHFFFAOYSA-N ethyl N'-(aminomethyl)carbamimidothioate Chemical class CCS\C(N)=N\CN BKNASEOAKDDNFJ-UHFFFAOYSA-N 0.000 claims 2
150000008050 dialkyl sulfates Chemical class 0.000 claims 1
150000002825 nitriles Chemical class 0.000 claims 1
230000008018 melting Effects 0.000 description 36
238000002844 melting Methods 0.000 description 36
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
230000000694 effects Effects 0.000 description 33
239000011541 reaction mixture Substances 0.000 description 31
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
210000004027 cell Anatomy 0.000 description 21
206010028980 Neoplasm Diseases 0.000 description 19
239000013078 crystal Substances 0.000 description 18
238000012360 testing method Methods 0.000 description 17
239000000706 filtrate Substances 0.000 description 16
238000009835 boiling Methods 0.000 description 15
238000003756 stirring Methods 0.000 description 14
238000011282 treatment Methods 0.000 description 14
239000000725 suspension Substances 0.000 description 13
241001465754 Metazoa Species 0.000 description 12
PQHJXKOVINDQES-UHFFFAOYSA-N carbonic acid;(e)-hydrazinylmethylidenethiourea Chemical compound OC(O)=O.NN\C=N\C(N)=S PQHJXKOVINDQES-UHFFFAOYSA-N 0.000 description 12
206010003445 Ascites Diseases 0.000 description 11
210000004698 lymphocyte Anatomy 0.000 description 11
210000004881 tumor cell Anatomy 0.000 description 11
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
230000000259 anti-tumor effect Effects 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
239000000463 material Substances 0.000 description 9
239000008187 granular material Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
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
241000699670 Mus sp. Species 0.000 description 6
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239000000243 solution Substances 0.000 description 6
210000001519 tissue Anatomy 0.000 description 6
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231100000419 toxicity Toxicity 0.000 description 6
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
239000003708 ampul Substances 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000001569 carbon dioxide Substances 0.000 description 5
229910002092 carbon dioxide Inorganic materials 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000007789 gas Substances 0.000 description 5
210000004565 granule cell Anatomy 0.000 description 5
229910000037 hydrogen sulfide Inorganic materials 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
239000002904 solvent Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
241000282472 Canis lupus familiaris Species 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
125000000304 alkynyl group Chemical group 0.000 description 4
230000010056 antibody-dependent cellular cytotoxicity Effects 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
231100000673 dose–response relationship Toxicity 0.000 description 4
239000008298 dragée Substances 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
210000002381 plasma Anatomy 0.000 description 4
231100000331 toxic Toxicity 0.000 description 4
230000002588 toxic effect Effects 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
241000238876 Acari Species 0.000 description 3
206010025323 Lymphomas Diseases 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
125000003342 alkenyl group Chemical group 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000001472 cytotoxic effect Effects 0.000 description 3
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
210000003743 erythrocyte Anatomy 0.000 description 3
238000001914 filtration Methods 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
210000000265 leukocyte Anatomy 0.000 description 3
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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
229920000936 Agarose Polymers 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
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206010027476 Metastases Diseases 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
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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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
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
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TVDCSPSRGSLXOV-UHFFFAOYSA-N 1-bromo-3-chloropropan-2-ol Chemical compound ClCC(O)CBr TVDCSPSRGSLXOV-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
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125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
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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
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
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
230000009471 action Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000910 agglutinin Substances 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001450 anions Chemical group 0.000 description 1
230000007953 anoxia Effects 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
239000003096 antiparasitic agent Substances 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
238000001574 biopsy Methods 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
230000037396 body weight Effects 0.000 description 1
SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
208000035269 cancer or benign tumor Diseases 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
KMPYMDDJOMYIEU-UHFFFAOYSA-N carbonic acid;1-(hydrazinylmethylidene)-3-methylthiourea Chemical compound OC(O)=O.CNC(=S)N=CNN KMPYMDDJOMYIEU-UHFFFAOYSA-N 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
230000003293 cardioprotective effect Effects 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
230000005779 cell damage Effects 0.000 description 1
208000037887 cell injury Diseases 0.000 description 1
230000004709 cell invasion Effects 0.000 description 1
230000022534 cell killing Effects 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
230000004087 circulation Effects 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 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
230000002380 cytological effect Effects 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
OKGXJRGLYVRVNE-UHFFFAOYSA-N diaminomethylidenethiourea Chemical compound NC(N)=NC(N)=S OKGXJRGLYVRVNE-UHFFFAOYSA-N 0.000 description 1
QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003344 environmental pollutant Substances 0.000 description 1
230000002327 eosinophilic effect Effects 0.000 description 1
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000002474 experimental method 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
239000006260 foam Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000007710 freezing Methods 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000036541 health 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
230000005965 immune activity Effects 0.000 description 1
230000001900 immune effect Effects 0.000 description 1
229960001438 immunostimulant agent Drugs 0.000 description 1
239000003022 immunostimulating agent Substances 0.000 description 1
230000001506 immunosuppresive effect Effects 0.000 description 1
229960003444 immunosuppressant agent Drugs 0.000 description 1
230000001861 immunosuppressant effect Effects 0.000 description 1
239000003018 immunosuppressive agent Substances 0.000 description 1
238000002513 implantation Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
210000005007 innate immune system Anatomy 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
230000009545 invasion Effects 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
229960001317 isoprenaline Drugs 0.000 description 1
229940039009 isoproterenol Drugs 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
230000033001 locomotion Effects 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
229960005485 mitobronitol Drugs 0.000 description 1
239000003226 mitogen Substances 0.000 description 1
231100001224 moderate toxicity Toxicity 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
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
210000000822 natural killer cell Anatomy 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
230000000174 oncolytic effect Effects 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
229940045681 other alkylating agent in atc Drugs 0.000 description 1
201000002528 pancreatic cancer Diseases 0.000 description 1
244000045947 parasite Species 0.000 description 1
239000002245 particle Substances 0.000 description 1
210000001539 phagocyte Anatomy 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
230000001885 phytohemagglutinin Effects 0.000 description 1
230000036470 plasma concentration Effects 0.000 description 1
231100000719 pollutant Toxicity 0.000 description 1
125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
230000005855 radiation Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000002271 resection Methods 0.000 description 1
230000004202 respiratory function Effects 0.000 description 1
230000036387 respiratory rate Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000012216 screening Methods 0.000 description 1
239000012748 slip agent Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
230000001629 suppression Effects 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
229940104230 thymidine Drugs 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000048 toxicity data Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 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)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Biomedical Technology (AREA)
Heart & Thoracic Surgery (AREA)
Tropical Medicine & Parasitology (AREA)
Anesthesiology (AREA)
Cardiology (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)

JP60501619A 1984-04-03 1985-04-02 イソチウロニウム塩 Expired - Lifetime JPH0825992B2 (ja)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
HU841324A HU196745B (en)	1984-04-03	1984-04-03	Process for producing n-/amino-imino-methyl/-isothiuronium derivatives with immunostimulant and cytostatic effect
HU1324/84		1985-03-19
HU132485		1985-03-19
PCT/HU1985/000022 WO1985004399A1 (en)	1984-04-03	1985-04-02	Isothiuronium salts

Publications (2)

Publication Number	Publication Date
JPS61501849A JPS61501849A (ja)	1986-08-28
JPH0825992B2 true JPH0825992B2 (ja)	1996-03-13

Family

ID=26317358

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP60501619A Expired - Lifetime JPH0825992B2 (ja)	1984-04-03	1985-04-02	イソチウロニウム塩

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)

* 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
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 JP JP60501619A patent/JPH0825992B2/ja not_active Expired - Lifetime
- 1985-04-02 DE DE19853590133 patent/DE3590133T1/de not_active Withdrawn
- 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
FI80259B (fi)	1990-01-31
PL145636B1 (en)	1988-10-31
DE3590133T1 (de)	1986-06-26
PL252744A1 (en)	1986-08-12
GB8529529D0 (en)	1986-01-08
FI854790A0 (fi)	1985-12-03
GB2167750A (en)	1986-06-04
GB2167750B (en)	1988-04-27
CN1008093B (zh)	1990-05-23
IL74743A0 (en)	1985-06-30
CN85103160A (zh)	1986-09-17
JPS61501849A (ja)	1986-08-28
FI854790L (fi)	1985-12-03
NZ211639A (en)	1989-03-29
FI80259C (fi)	1990-05-10
IL74743A (en)	1992-09-06

Publication	Publication Date	Title
JP2748333B2 (ja)	1998-05-06	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
US4511582A (en)	1985-04-16	Phenanthrene derivatives
US4551282A (en)	1985-11-05	Triphenylene derivatives
KR860001865B1 (ko)	1986-10-24	2'-데옥시-5-치환 우리딘 유도체의 제조방법
RU2027442C1 (ru)	1995-01-27	Вещество, обладающее противоопухолевой активностью
RU2108100C1 (ru)	1998-04-10	Иммуномодулятор
US3993781A (en)	1976-11-23	1,6-Dibromo-1,6-dideoxy-dulcitol and pharmaceutical compositions containing same
US4571335A (en)	1986-02-18	Method of inhibiting herpetic lesions by the use of platinum coordination compounds
US3824276A (en)	1974-07-16	Substituted-2-oxobutyraldehyde bis(thiosemicarbazones)
FI80259B (fi)	1990-01-31	Foerfarande foer framstaellning av terapeutiskt anvaendbara isotiuronium-salter.
US4430347A (en)	1984-02-07	Cystamine derivatives suitable for use as medicaments
US4710578A (en)	1987-12-01	Isothiuronium salts
US4416878A (en)	1983-11-22	[8-(Dialkylamino alkoxy)-caffeine]-platinum complex compounds and pharmaceutical products containing the same
SE436208B (sv)	1984-11-19	Sett att framstella 5-fluoro-uracilderivat
FI75809B (fi)	1988-04-29	Foerfarande foer framstaellning av terapeutiskt aktiva vattenloesliga derivat av 6,6'-metylen-bis(2,2,4- trimetyl-1,2-dihydrokinolin).
US4939156A (en)	1990-07-03	New tetramethyl-cis-diaza-bicyclo{4.2.0}octane-3,5-dione derivatives having differentiation-inducing activity and antiviral activity
US4510147A (en)	1985-04-09	Compositions for and medical use of water-soluble derivatives of 6,6-methylene-bis-(2,2,4-trimethyl-1,2-dihydroquinoline)
KR19990034285A (ko)	1999-05-15	항암활성을 갖는 육두구 추출물
US4481201A (en)	1984-11-06	Pharmaceutical composition containing N,N3 -di-(β-bromopropionyl)-N1,N2 -dispirotripiperazinium dichloride
CN113748119B (zh)	2024-04-02	一种用作iap抑制剂的smac模拟物的结晶及其制备方法
RU2171811C2 (ru)	2001-08-10	КРИСТАЛЛИЧЕСКИЙ ТРИГИДРОХЛОРИД ДЕОКСИСПЕРГУАЛИНА В β-ФОРМЕ, ОБЛАДАЮЩИЙ ПРОТИВООПУХОЛЕВОЙ АКТИВНОСТЬЮ И СПОСОБ ЕГО ПОЛУЧЕНИЯ
JPS61189292A (ja)	1986-08-22	５−フルオロデオキシウリジン誘導体の新規な固溶体及びこれを活性成分として含有する制癌剤
JPS6011685B2 (ja)	1985-03-27	トランス−４−アミノメチルシクロヘキサン−１−カルボン酸誘導体制癌剤
JPS6366287B2 (pl)	1988-12-20
US4046897A (en)	1977-09-06	5-Mercaptopyridoxine alkanesulfonates and methods of use and pharmaceutical compositions