JPH0440356B2 - - Google Patents
Info
- Publication number
- JPH0440356B2 JPH0440356B2 JP62018295A JP1829587A JPH0440356B2 JP H0440356 B2 JPH0440356 B2 JP H0440356B2 JP 62018295 A JP62018295 A JP 62018295A JP 1829587 A JP1829587 A JP 1829587A JP H0440356 B2 JPH0440356 B2 JP H0440356B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- dithiol
- thione
- compound
- lower alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- LEPDMIYUICCABX-UHFFFAOYSA-N 5-methyldithiole-3-thione Chemical compound CC1=CC(=S)SS1 LEPDMIYUICCABX-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- LZENMJMJWQSSNJ-UHFFFAOYSA-N 3H-1,2-dithiole-3-thione Chemical class S=C1C=CSS1 LZENMJMJWQSSNJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 25
- 230000000694 effects Effects 0.000 description 11
- 239000013078 crystal Substances 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 230000036737 immune function Effects 0.000 description 7
- 239000002955 immunomodulating agent Substances 0.000 description 7
- 229940121354 immunomodulator Drugs 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- 230000002519 immonomodulatory effect Effects 0.000 description 6
- AGBQKNBQESQNJD-UHFFFAOYSA-N lipoic acid Chemical compound OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 235000019136 lipoic acid Nutrition 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 210000004988 splenocyte Anatomy 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229960002663 thioctic acid Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical class O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 3
- ICADXNGCMYDRDQ-UHFFFAOYSA-N 4,4-bis(methylsulfanyl)but-3-en-2-one Chemical compound CSC(SC)=CC(C)=O ICADXNGCMYDRDQ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 108010062580 Concanavalin A Proteins 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- -1 dithiol-3-thione compound Chemical class 0.000 description 3
- 201000002491 encephalomyelitis Diseases 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000003053 immunization Effects 0.000 description 3
- 238000002649 immunization Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 201000006417 multiple sclerosis Diseases 0.000 description 3
- HONRSHHPFBMLBT-OWOJBTEDSA-N (e)-3-(4-chlorophenyl)prop-2-enal Chemical compound ClC1=CC=C(\C=C\C=O)C=C1 HONRSHHPFBMLBT-OWOJBTEDSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- AXCXHFKZHDEKTP-NSCUHMNNSA-N 4-methoxycinnamaldehyde Chemical compound COC1=CC=C(\C=C\C=O)C=C1 AXCXHFKZHDEKTP-NSCUHMNNSA-N 0.000 description 2
- IYWBUHTYEIHJMP-UHFFFAOYSA-N 5-(4-phenylbuta-1,3-dienyl)dithiole-3-thione Chemical compound S1SC(=S)C=C1C=CC=CC1=CC=CC=C1 IYWBUHTYEIHJMP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 208000023275 Autoimmune disease Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010061598 Immunodeficiency Diseases 0.000 description 2
- 208000029462 Immunodeficiency disease Diseases 0.000 description 2
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000034994 death Effects 0.000 description 2
- 231100000517 death Toxicity 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000007813 immunodeficiency Effects 0.000 description 2
- 230000016784 immunoglobulin production Effects 0.000 description 2
- 230000002584 immunomodulator Effects 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 229960001614 levamisole Drugs 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- AGBQKNBQESQNJD-SSDOTTSWSA-N (R)-lipoic acid Chemical compound OC(=O)CCCC[C@@H]1CCSS1 AGBQKNBQESQNJD-SSDOTTSWSA-N 0.000 description 1
- NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- HGBCDXOKFIDHNS-UHFFFAOYSA-N 3-(2-chlorophenyl)prop-2-enal Chemical compound ClC1=CC=CC=C1C=CC=O HGBCDXOKFIDHNS-UHFFFAOYSA-N 0.000 description 1
- SJLLZWMNPJCLBC-UHFFFAOYSA-N 3-(3-methylphenyl)prop-2-enal Chemical compound CC1=CC=CC(C=CC=O)=C1 SJLLZWMNPJCLBC-UHFFFAOYSA-N 0.000 description 1
- DKOUYOVAEBQFHU-NSCUHMNNSA-N 3-(4-Methylphenyl)-2-propenal Chemical compound CC1=CC=C(\C=C\C=O)C=C1 DKOUYOVAEBQFHU-NSCUHMNNSA-N 0.000 description 1
- RUKJCCIJLIMGEP-ONEGZZNKSA-N 4-dimethylaminocinnamaldehyde Chemical compound CN(C)C1=CC=C(\C=C\C=O)C=C1 RUKJCCIJLIMGEP-ONEGZZNKSA-N 0.000 description 1
- IDFCDFJATZJYJJ-UHFFFAOYSA-N 5-[4-(2-chlorophenyl)buta-1,3-dienyl]dithiole-3-thione Chemical compound ClC1=CC=CC=C1C=CC=CC1=CC(=S)SS1 IDFCDFJATZJYJJ-UHFFFAOYSA-N 0.000 description 1
- VMBBDXJWMUQRQA-UHFFFAOYSA-N 5-[4-(3-methylphenyl)buta-1,3-dienyl]dithiole-3-thione Chemical compound CC1=CC=CC(C=CC=CC=2SSC(=S)C=2)=C1 VMBBDXJWMUQRQA-UHFFFAOYSA-N 0.000 description 1
- BNCZWSKSIAUPMB-UHFFFAOYSA-N 5-[4-(4-chlorophenyl)buta-1,3-dienyl]dithiole-3-thione Chemical compound C1=CC(Cl)=CC=C1C=CC=CC1=CC(=S)SS1 BNCZWSKSIAUPMB-UHFFFAOYSA-N 0.000 description 1
- PUEVGWRSPNNKLQ-UHFFFAOYSA-N 5-[4-(4-methoxyphenyl)buta-1,3-dienyl]dithiole-3-thione Chemical compound C1=CC(OC)=CC=C1C=CC=CC1=CC(=S)SS1 PUEVGWRSPNNKLQ-UHFFFAOYSA-N 0.000 description 1
- RCYJMGJZEABCDU-UHFFFAOYSA-N 5-[4-(4-methylphenyl)buta-1,3-dienyl]dithiole-3-thione Chemical compound C1=CC(C)=CC=C1C=CC=CC1=CC(=S)SS1 RCYJMGJZEABCDU-UHFFFAOYSA-N 0.000 description 1
- CHRPIKDARCFFAA-UHFFFAOYSA-N 5-[4-[4-(dimethylamino)phenyl]buta-1,3-dienyl]dithiole-3-thione Chemical compound C1=CC(N(C)C)=CC=C1C=CC=CC1=CC(=S)SS1 CHRPIKDARCFFAA-UHFFFAOYSA-N 0.000 description 1
- ZCSKFDIEYBVILK-UHFFFAOYSA-N 5-methyl-3h-dithiole Chemical compound CC1=CCSS1 ZCSKFDIEYBVILK-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 201000010000 Agranulocytosis Diseases 0.000 description 1
- 208000032116 Autoimmune Experimental Encephalomyelitis Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000019838 Blood disease Diseases 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 230000006820 DNA synthesis Effects 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- 206010018687 Granulocytopenia Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010062016 Immunosuppression Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000005777 Lupus Nephritis Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001049988 Mycobacterium tuberculosis H37Ra Species 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 241000144290 Sigmodon hispidus Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 206010049040 Weight fluctuation Diseases 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 210000000628 antibody-producing cell Anatomy 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000035584 blastogenesis Effects 0.000 description 1
- 238000004820 blood count Methods 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 229940117916 cinnamic aldehyde Drugs 0.000 description 1
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 208000014951 hematologic disease Diseases 0.000 description 1
- 208000018706 hematopoietic system disease Diseases 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 238000011694 lewis rat Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- 239000000724 thymus hormone Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/04—Five-membered rings having the hetero atoms in positions 1 and 2, e.g. lipoic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000531036A CA1301177C (en) | 1986-03-05 | 1987-03-03 | Process of producing novel 1,2-dithiol-3-thione derivative |
| DE8787103076T DE3767894D1 (de) | 1986-03-05 | 1987-03-04 | 1,2-dithiol-3-thion-derivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammenstellung. |
| EP87103076A EP0236929B1 (en) | 1986-03-05 | 1987-03-04 | 1,2-dithiol-3-thione derivatives, a process for preparing them and a pharmaceutical composition containing them |
| HU87945A HU200451B (en) | 1986-03-05 | 1987-03-05 | Process for production of derivatives of 1,2-ditiol-3-tion and medical compositions containing them as active substance |
| US07/022,349 US4760078A (en) | 1986-03-05 | 1987-03-05 | Immunomodulator 1,2-dithiol-3-thione derivative composition, use method and process of producing the same |
| KR1019870009838A KR900000968B1 (ko) | 1986-03-05 | 1987-09-04 | 1,2-디티올-3-티온 유도체, 이의 제조방법 및 조성물 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4631886 | 1986-03-05 | ||
| JP61-46318 | 1986-03-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6310785A JPS6310785A (ja) | 1988-01-18 |
| JPH0440356B2 true JPH0440356B2 (no) | 1992-07-02 |
Family
ID=12743812
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62018295A Granted JPS6310785A (ja) | 1986-03-05 | 1987-01-30 | 新規１，２−ジチオ−ル−３−チオン誘導体、その製造方法およびそれを有効成分とする免疫調節剤 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS6310785A (no) |
| KR (1) | KR900000968B1 (no) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH089611B2 (ja) * | 1988-06-20 | 1996-01-31 | 三井東圧化学株式会社 | 新規１，２−ジチオール−３−チオン誘導体およびそれを有効成分とする免疫調節剤 |
| JPH0816059B2 (ja) * | 1993-05-21 | 1996-02-21 | 三井東圧化学株式会社 | 免疫調節剤 |
| KR100484526B1 (ko) * | 2002-11-13 | 2005-04-20 | 씨제이 주식회사 | 티온 유도체, 그 제조방법 및 약제학적 조성물 |
-
1987
- 1987-01-30 JP JP62018295A patent/JPS6310785A/ja active Granted
- 1987-09-04 KR KR1019870009838A patent/KR900000968B1/ko not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR900000968B1 (ko) | 1990-02-23 |
| KR880009006A (ko) | 1988-09-13 |
| JPS6310785A (ja) | 1988-01-18 |
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