SU1318164A3 - Способ получени производных 5-амино-1,2-дитиол-3-она - Google Patents
Способ получени производных 5-амино-1,2-дитиол-3-она Download PDFInfo
- Publication number
- SU1318164A3 SU1318164A3 SU843703553A SU3703553A SU1318164A3 SU 1318164 A3 SU1318164 A3 SU 1318164A3 SU 843703553 A SU843703553 A SU 843703553A SU 3703553 A SU3703553 A SU 3703553A SU 1318164 A3 SU1318164 A3 SU 1318164A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dithiol
- general formula
- amino
- tetrahydro
- dichloro
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- IRGJAPXKRFEBNA-UHFFFAOYSA-N 5-aminodithiol-3-one Chemical class NC1=CC(=O)SS1 IRGJAPXKRFEBNA-UHFFFAOYSA-N 0.000 title claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 18
- QGSRKGWCQSATCL-UHFFFAOYSA-N 4,5-dichloro-3h-1,3-dithiol-2-one Chemical compound ClC=1SSC(=O)C=1Cl QGSRKGWCQSATCL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 235000015497 potassium bicarbonate Nutrition 0.000 claims abstract description 4
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims abstract description 4
- 239000011736 potassium bicarbonate Substances 0.000 claims abstract description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims abstract description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 150000001412 amines Chemical class 0.000 claims abstract 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- 230000000144 pharmacologic effect Effects 0.000 claims description 3
- QRAOZQGIUIDZQZ-UHFFFAOYSA-N 4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzoxazine Chemical compound C=1C=C2N(C)CCOC2=CC=1B1OC(C)(C)C(C)(C)O1 QRAOZQGIUIDZQZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 2
- SXLZJUPRTINRQQ-UHFFFAOYSA-N 4-methyl-2,3-dihydro-1h-quinoxaline Chemical compound C1=CC=C2N(C)CCNC2=C1 SXLZJUPRTINRQQ-UHFFFAOYSA-N 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 208000025747 Rheumatic disease Diseases 0.000 abstract description 4
- MZBVNYACSSGXID-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-1-benzazepine Chemical compound N1CCCCC2=CC=CC=C21 MZBVNYACSSGXID-UHFFFAOYSA-N 0.000 abstract description 2
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 239000013543 active substance Substances 0.000 abstract 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 150000003463 sulfur Chemical class 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- -1 5-amino-1 Chemical class 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003701 inert diluent 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
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000008055 phosphate buffer solution Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JPTJBBJVZPURSQ-UHFFFAOYSA-N 4-chlorodithiol-3-one Chemical compound ClC1=CSSC1=O JPTJBBJVZPURSQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 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
- 241000699670 Mus sp. Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 206010057249 Phagocytosis Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229920000392 Zymosan Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- WQZGKKKJIJFFOK-DVKNGEFBSA-N alpha-D-glucose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-DVKNGEFBSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
- 125000002785 azepinyl group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 230000000112 colonic effect Effects 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000011534 incubation Methods 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
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- QXUAFCKBYYPTPQ-ZWKAXHIPSA-L magnesium (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(2R,3S,4R,5R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol octadecanoate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O QXUAFCKBYYPTPQ-ZWKAXHIPSA-L 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 210000003024 peritoneal macrophage Anatomy 0.000 description 1
- 230000008782 phagocytosis Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8303005A FR2541680B1 (fr) | 1983-02-24 | 1983-02-24 | Nouveaux derives de l'amino-5 dithiole-1,2 one-3, leur preparation et les compositions medicinales qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1318164A3 true SU1318164A3 (ru) | 1987-06-15 |
Family
ID=9286218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU843703553A SU1318164A3 (ru) | 1983-02-24 | 1984-02-23 | Способ получени производных 5-амино-1,2-дитиол-3-она |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4576954A (enExample) |
| EP (1) | EP0119896B1 (enExample) |
| JP (1) | JPS59163383A (enExample) |
| KR (1) | KR900006745B1 (enExample) |
| AT (1) | ATE22690T1 (enExample) |
| AU (1) | AU567718B2 (enExample) |
| CA (1) | CA1227197A (enExample) |
| DE (1) | DE3460896D1 (enExample) |
| DK (1) | DK159111C (enExample) |
| ES (1) | ES8500939A1 (enExample) |
| FR (1) | FR2541680B1 (enExample) |
| GR (1) | GR81662B (enExample) |
| HU (1) | HU194863B (enExample) |
| IE (1) | IE56920B1 (enExample) |
| NO (1) | NO169388C (enExample) |
| NZ (1) | NZ207244A (enExample) |
| SU (1) | SU1318164A3 (enExample) |
| ZA (1) | ZA841274B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2169731C2 (ru) * | 1997-04-02 | 2001-06-27 | Санкио Компани, Лимитед | Производные дитиолана, лекарственные средства |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI435729B (zh) | 2005-11-09 | 2014-05-01 | Combinatorx Inc | 治療病症之方法，組合物及套組 |
| RU2720237C2 (ru) | 2013-11-18 | 2020-04-28 | Форма Терапеутикс, Инк. | Композиции, содержащие бензопиперазин, в качестве ингибиторов бромодоменов вет |
| DK3071203T3 (da) | 2013-11-18 | 2021-03-15 | Forma Therapeutics Inc | Tetrahydroquinolinsammensætninger som bet-bromdomæne-inhibitorer |
| TW202009235A (zh) | 2018-08-17 | 2020-03-01 | 印度商皮埃企業有限公司 | 1,2-二硫醇酮化合物及其用途 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1498374A (fr) * | 1965-06-11 | 1967-10-20 | Agripat Sa | Produits fongicides et bactéricides, utilisables en agriculture |
| US3527867A (en) * | 1965-06-11 | 1970-09-08 | Geigy Chem Corp | Agents inhibiting fungus growth and method of controlling fungi therewith |
| US3772273A (en) * | 1969-01-17 | 1973-11-13 | Allied Chem | Derivatives of quinoxaline |
| US3984405A (en) * | 1971-06-28 | 1976-10-05 | E. R. Squibb & Sons, Inc. | Anti-inflammatory agents |
| BE795970A (fr) * | 1972-02-29 | 1973-08-27 | Pfizer | Nouveaux derives de quinoleine, quinoxaline et quinazoline er composition pharmaceutiques les contenant |
| JPS5819644B2 (ja) * | 1975-03-13 | 1983-04-19 | ウェルファイド株式会社 | スイチユウボウオザイ |
| FR2347928A1 (fr) * | 1976-04-15 | 1977-11-10 | Rhone Poulenc Ind | Nouveaux derives du dithiole-1,2, leur preparation et les compositions qui les contiennent |
| SE444319B (sv) * | 1977-11-18 | 1986-04-07 | Roussel Uclaf | Nya imidazobensoxazinderivat, forfarande for framstellning derav och farmaceutiska kompositioner innehallande dessa foreningar |
| US4254118A (en) * | 1979-08-13 | 1981-03-03 | Ayerst, Mckenna & Harrison Inc. | 1-Oxo-5H-pyrimido[2,1-c][1,4]benzthiazine-2-carboxylic acid esters |
| US4273773A (en) * | 1979-09-24 | 1981-06-16 | American Home Products Corporation | Antihypertensive tricyclic isoindole derivatives |
| US4477378A (en) * | 1980-02-05 | 1984-10-16 | Schering Corp. | Esters of substituted 8-hydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines |
| CA1211437A (en) * | 1981-08-12 | 1986-09-16 | Rene Borer | Benzazepines |
-
1983
- 1983-02-24 FR FR8303005A patent/FR2541680B1/fr not_active Expired
-
1984
- 1984-02-21 ZA ZA841274A patent/ZA841274B/xx unknown
- 1984-02-21 US US06/582,043 patent/US4576954A/en not_active Expired - Fee Related
- 1984-02-22 GR GR73885A patent/GR81662B/el unknown
- 1984-02-22 IE IE418/84A patent/IE56920B1/en not_active IP Right Cessation
- 1984-02-22 NZ NZ207244A patent/NZ207244A/en unknown
- 1984-02-23 AU AU24855/84A patent/AU567718B2/en not_active Ceased
- 1984-02-23 HU HU84724A patent/HU194863B/hu not_active IP Right Cessation
- 1984-02-23 NO NO840698A patent/NO169388C/no unknown
- 1984-02-23 EP EP84400368A patent/EP0119896B1/fr not_active Expired
- 1984-02-23 DK DK093984A patent/DK159111C/da not_active IP Right Cessation
- 1984-02-23 KR KR1019840000890A patent/KR900006745B1/ko not_active Expired
- 1984-02-23 ES ES529986A patent/ES8500939A1/es not_active Expired
- 1984-02-23 JP JP59031542A patent/JPS59163383A/ja active Pending
- 1984-02-23 CA CA000448088A patent/CA1227197A/fr not_active Expired
- 1984-02-23 AT AT84400368T patent/ATE22690T1/de active
- 1984-02-23 DE DE8484400368T patent/DE3460896D1/de not_active Expired
- 1984-02-23 SU SU843703553A patent/SU1318164A3/ru active
Non-Patent Citations (1)
| Title |
|---|
| Бюлер К., Пирсон Д. Органические синтезы. Ч. 1 М.: Мир, 1973, с. 504. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2169731C2 (ru) * | 1997-04-02 | 2001-06-27 | Санкио Компани, Лимитед | Производные дитиолана, лекарственные средства |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE22690T1 (de) | 1986-10-15 |
| EP0119896A1 (fr) | 1984-09-26 |
| FR2541680B1 (fr) | 1985-06-14 |
| CA1227197A (fr) | 1987-09-22 |
| KR900006745B1 (ko) | 1990-09-20 |
| US4576954A (en) | 1986-03-18 |
| NO840698L (no) | 1984-08-27 |
| DK159111C (da) | 1991-02-11 |
| NO169388B (no) | 1992-03-09 |
| AU567718B2 (en) | 1987-12-03 |
| ZA841274B (en) | 1984-09-26 |
| HUT35663A (en) | 1985-07-29 |
| NZ207244A (en) | 1986-12-05 |
| DK93984D0 (da) | 1984-02-23 |
| DE3460896D1 (en) | 1986-11-13 |
| FR2541680A1 (fr) | 1984-08-31 |
| KR840008025A (ko) | 1984-12-12 |
| NO169388C (no) | 1992-06-17 |
| EP0119896B1 (fr) | 1986-10-08 |
| GR81662B (enExample) | 1984-12-12 |
| DK159111B (da) | 1990-09-03 |
| IE56920B1 (en) | 1992-01-29 |
| AU2485584A (en) | 1984-08-30 |
| IE840418L (en) | 1984-08-24 |
| ES529986A0 (es) | 1984-11-01 |
| JPS59163383A (ja) | 1984-09-14 |
| HU194863B (en) | 1988-03-28 |
| DK93984A (da) | 1984-08-25 |
| ES8500939A1 (es) | 1984-11-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN116514777B (zh) | 驱动蛋白kif18a抑制剂及其应用 | |
| DE69310475T2 (de) | Benzokondensierte Lactame | |
| DE69426376T2 (de) | Substituierte Azepino (2,1-a)isochinolin Verbindungen | |
| JP2021519282A (ja) | ＨＩＦ−２−αの阻害薬による消化器系の炎症軽減方法 | |
| EP4595965A2 (en) | Heteroalkyl dihydroquinoline sulfonamide compounds | |
| MC1491A1 (fr) | Nouveaux composes bicycliques,procedes pour les preparer et formules pharmaceutiques contenant ces composes | |
| EP0692483A1 (en) | Cell adhesion inhibitor and thienotriazolodiazepine compound | |
| JP7584802B2 (ja) | 高活性ｓｔｉｎｇタンパク質アゴニスト | |
| US4985445A (en) | Cancer cell metastasis inhibitors and novel compounds | |
| WO2021055589A1 (en) | Heteroaryl plasma kallikrein inhibitors | |
| SU1318164A3 (ru) | Способ получени производных 5-амино-1,2-дитиол-3-она | |
| CN120359210A (zh) | Cyp11b2抑制剂化合物、药物组合物及其应用 | |
| US8252942B2 (en) | Substituted imidazoline compounds | |
| EP4273143B1 (en) | Derivative of 2,5-diketopiperazine compound, and preparation method therefor, pharmaceutical composition thereof and use thereof | |
| DE69221634T2 (de) | 5-Piperazinylalkyl)-1,5-Benzothiazepinone verwendbar als Calciumantagonisten | |
| EP0399626B1 (en) | Substituted pyridine compounds, their production, and pharmaceutical compositions containing them | |
| EP0237138A1 (en) | Heterocyclic compounds, their preparation and, pharmaceutical compositions containing them | |
| EP3790885B1 (en) | 1-imidazothiadiazolo-2h-pyrrol-5-one derivatives | |
| JP2008530053A (ja) | 癌の治療のための抗増殖性剤としてのテトラヒドロピリドチオフェン | |
| CN108084193A (zh) | 一种brd4蛋白抑制剂 | |
| SK695188A3 (en) | Enolether amide 1,1-dioxo-6-chloro-4-hydroxy-2-methyl-n-(2- -pyridyl)-2h-thieno (2,3-e)-1,2-thiazine-3-carboxylic acid, method of its production and pharmaceutical agent | |
| AU2004283822A1 (en) | Glutamine fructose-6-phosphate amidotransferase (GFAT) inhibitors | |
| US5066649A (en) | 8,9-annelated-1,2,3,4-tetrahydro-β-carboline derivatives | |
| EA003511B1 (ru) | Производные пиперазинона и их применение | |
| EP3652183B1 (en) | 2-oxo-1,3-oxazolidinyl imidazothiadiazole derivatives |