JPH0455191B2 - - Google Patents
Info
- Publication number
- JPH0455191B2 JPH0455191B2 JP1440484A JP1440484A JPH0455191B2 JP H0455191 B2 JPH0455191 B2 JP H0455191B2 JP 1440484 A JP1440484 A JP 1440484A JP 1440484 A JP1440484 A JP 1440484A JP H0455191 B2 JPH0455191 B2 JP H0455191B2
- Authority
- JP
- Japan
- Prior art keywords
- dione
- dithiol
- ylidene
- general formula
- group
- 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
Links
- -1 Dithiol-2-ylidene Chemical class 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 7
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- 208000019423 liver disease Diseases 0.000 claims description 6
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- IBNLVXNNYIGLLB-UHFFFAOYSA-N 4-propan-2-ylcyclohexane-1,3-dione Chemical compound CC(C)C1CCC(=O)CC1=O IBNLVXNNYIGLLB-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- LOGSONSNCYTHPS-UHFFFAOYSA-N cyclopentane-1,3-dione Chemical compound O=C1CCC(=O)C1 LOGSONSNCYTHPS-UHFFFAOYSA-N 0.000 claims description 3
- BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical compound CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229940124597 therapeutic agent Drugs 0.000 claims description 3
- BXDJIVKCVVTETR-UHFFFAOYSA-N 4-methylcyclohexane-1,3-dione Chemical compound CC1CCC(=O)CC1=O BXDJIVKCVVTETR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 description 9
- 206010067125 Liver injury Diseases 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 231100000234 hepatic damage Toxicity 0.000 description 7
- 230000008818 liver damage Effects 0.000 description 7
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- IRKODEMCSCXDOI-UHFFFAOYSA-M 1,3-dithiol-2-ylidene(methyl)sulfanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CSC=1SC=C[S+]=1 IRKODEMCSCXDOI-UHFFFAOYSA-M 0.000 description 3
- RFLIZWSLNXFRIC-UHFFFAOYSA-N 2-(1,3-dithiol-2-ylidene)-5,5-dimethylcyclohexane-1,3-dione Chemical compound O=C1CC(C)(C)CC(=O)C1=C1SC=CS1 RFLIZWSLNXFRIC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 102100036475 Alanine aminotransferase 1 Human genes 0.000 description 3
- 108010082126 Alanine transaminase Proteins 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000001771 impaired effect Effects 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- WPHAFPAFYDFOJR-UHFFFAOYSA-N 2-(1,3-dithiol-2-ylidene)-4-methylcyclohexane-1,3-dione Chemical compound O=C1C(C)CCC(=O)C1=C1SC=CS1 WPHAFPAFYDFOJR-UHFFFAOYSA-N 0.000 description 2
- VIOPPSBIJRKGEG-UHFFFAOYSA-N 2-(1,3-dithiol-2-ylidene)-4-propan-2-ylcyclohexane-1,3-dione Chemical compound O=C1C(C(C)C)CCC(=O)C1=C1SC=CS1 VIOPPSBIJRKGEG-UHFFFAOYSA-N 0.000 description 2
- YYYUZRHTQUIZIM-UHFFFAOYSA-N 2-(1,3-dithiol-2-ylidene)cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1=C1SC=CS1 YYYUZRHTQUIZIM-UHFFFAOYSA-N 0.000 description 2
- XJGAZCWXULIQTB-UHFFFAOYSA-N 2-(1,3-dithiol-2-ylidene)cyclopentane-1,3-dione Chemical compound O=C1CCC(=O)C1=C1SC=CS1 XJGAZCWXULIQTB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WYKJWNVWJOKVQP-UHFFFAOYSA-N 1,3-dithiole-2-thione Chemical compound S=C1SC=CS1 WYKJWNVWJOKVQP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SURCGQGDUADKBL-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-5-nitrobenzo[de]isoquinoline-1,3-dione Chemical compound [O-][N+](=O)C1=CC(C(N(NCCO)C2=O)=O)=C3C2=CC=CC3=C1 SURCGQGDUADKBL-UHFFFAOYSA-N 0.000 description 1
- PLGPBTCNKJQJHQ-UHFFFAOYSA-N 4,4-dimethylcyclohexane-1,3-dione Chemical compound CC1(C)CCC(=O)CC1=O PLGPBTCNKJQJHQ-UHFFFAOYSA-N 0.000 description 1
- TWQLMCLEFOMAGX-UHFFFAOYSA-N 4-ethyl-5-methylcyclohexane-1,3-dione Chemical compound CCC1C(C)CC(=O)CC1=O TWQLMCLEFOMAGX-UHFFFAOYSA-N 0.000 description 1
- IDESFDLCRXUSGK-UHFFFAOYSA-N 4-ethylcyclohexane-1,3-dione Chemical compound CCC1CCC(=O)CC1=O IDESFDLCRXUSGK-UHFFFAOYSA-N 0.000 description 1
- RRPRDBWLNNQNDM-UHFFFAOYSA-N 5,5-dibenzylcyclohexane-1,3-dione Chemical compound C1C(=O)CC(=O)CC1(CC=1C=CC=CC=1)CC1=CC=CC=C1 RRPRDBWLNNQNDM-UHFFFAOYSA-N 0.000 description 1
- VUUNCMULTZRHHS-UHFFFAOYSA-N 5,5-diethylcyclohexane-1,3-dione Chemical compound CCC1(CC)CC(=O)CC(=O)C1 VUUNCMULTZRHHS-UHFFFAOYSA-N 0.000 description 1
- QPDAUGDDIALNNE-UHFFFAOYSA-N 5,5-dimethyl-4-phenylcyclohexane-1,3-dione Chemical compound CC1(C)CC(=O)CC(=O)C1C1=CC=CC=C1 QPDAUGDDIALNNE-UHFFFAOYSA-N 0.000 description 1
- IYUHIAGDLSLWOQ-UHFFFAOYSA-N 5-methyl-5-phenylcyclohexane-1,3-dione Chemical compound C=1C=CC=CC=1C1(C)CC(=O)CC(=O)C1 IYUHIAGDLSLWOQ-UHFFFAOYSA-N 0.000 description 1
- DMIIMPQQPXUKOO-UHFFFAOYSA-N 5-methylcyclohexane-1,3-dione Chemical compound CC1CC(=O)CC(=O)C1 DMIIMPQQPXUKOO-UHFFFAOYSA-N 0.000 description 1
- UPPYKNLSSLIIAZ-UHFFFAOYSA-N 5-phenylcyclohexane-1,3-dione Chemical compound C1C(=O)CC(=O)CC1C1=CC=CC=C1 UPPYKNLSSLIIAZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-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
- 238000009835 boiling Methods 0.000 description 1
- GHAFORRTMVIXHS-UHFFFAOYSA-L bromosulfophthalein sodium Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(O)=CC=C1C1(C=2C=C(C(O)=CC=2)S([O-])(=O)=O)C(C(Br)=C(Br)C(Br)=C2Br)=C2C(=O)O1 GHAFORRTMVIXHS-UHFFFAOYSA-L 0.000 description 1
- 239000006172 buffering agent Substances 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
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 231100000753 hepatic injury Toxicity 0.000 description 1
- 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 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient 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
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1440484A JPS60161980A (ja) | 1984-01-31 | 1984-01-31 | １，３−ジチオ−ル−２−イリデン誘導体 |
| CN 85105298 CN85105298A (zh) | 1984-01-31 | 1985-07-10 | 1，3-二硫杂环戊二烯-2-亚基衍生物的制备方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1440484A JPS60161980A (ja) | 1984-01-31 | 1984-01-31 | １，３−ジチオ−ル−２−イリデン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60161980A JPS60161980A (ja) | 1985-08-23 |
| JPH0455191B2 true JPH0455191B2 (nl) | 1992-09-02 |
Family
ID=11860105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1440484A Granted JPS60161980A (ja) | 1984-01-31 | 1984-01-31 | １，３−ジチオ−ル−２−イリデン誘導体 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS60161980A (nl) |
| CN (1) | CN85105298A (nl) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4863925A (en) * | 1986-09-24 | 1989-09-05 | Nihon Nohyaku Co., Ltd. | Cyclohexanedione derivative for hepatic disorders and a process for producing the same |
| AT389310B (de) * | 1988-03-09 | 1989-11-27 | Nihon Nohyaku Co Ltd | Cyclohexandion-derivat und verfahren zu seiner herstellung |
-
1984
- 1984-01-31 JP JP1440484A patent/JPS60161980A/ja active Granted
-
1985
- 1985-07-10 CN CN 85105298 patent/CN85105298A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN85105298A (zh) | 1987-01-28 |
| JPS60161980A (ja) | 1985-08-23 |
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