NO781712L - Fremgangsmaate for fremstilling av nye derivater av 4-hydroksytiazolidin-2-tion - Google Patents
Fremgangsmaate for fremstilling av nye derivater av 4-hydroksytiazolidin-2-tionInfo
- Publication number
- NO781712L NO781712L NO78781712A NO781712A NO781712L NO 781712 L NO781712 L NO 781712L NO 78781712 A NO78781712 A NO 78781712A NO 781712 A NO781712 A NO 781712A NO 781712 L NO781712 L NO 781712L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- pyridyl
- dithiocarbamate
- melting point
- triethylammonium
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000012990 dithiocarbamate Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 238000009835 boiling Methods 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- WNQHHKFFJCEFRW-UHFFFAOYSA-N n-(6-methylpyridin-2-yl)carbamodithioate;triethylazanium Chemical compound CC[NH+](CC)CC.CC1=CC=CC(NC([S-])=S)=N1 WNQHHKFFJCEFRW-UHFFFAOYSA-N 0.000 description 9
- 239000012153 distilled water Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- -1 (6-Methyl-2-pyridyl)-thiazolidine-2-thione Chemical compound 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- AALRHBLMAVGWRR-UHFFFAOYSA-N 1-chlorobutan-2-one Chemical compound CCC(=O)CCl AALRHBLMAVGWRR-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- WACNUSGXNNCCDV-UHFFFAOYSA-N n-(6-ethylpyridin-2-yl)carbamodithioate;triethylazanium Chemical compound CC[NH+](CC)CC.CCC1=CC=CC(NC([S-])=S)=N1 WACNUSGXNNCCDV-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- GGTWUPLPAPTFAR-UHFFFAOYSA-N 1-chloro-3-methylbutan-2-one Chemical compound CC(C)C(=O)CCl GGTWUPLPAPTFAR-UHFFFAOYSA-N 0.000 description 2
- FVXNLWRKEVZHKO-UHFFFAOYSA-N 1-chlorohexan-2-one Chemical compound CCCCC(=O)CCl FVXNLWRKEVZHKO-UHFFFAOYSA-N 0.000 description 2
- MGTGUEKJBFTQQW-UHFFFAOYSA-N 1-chloropentan-2-one Chemical compound CCCC(=O)CCl MGTGUEKJBFTQQW-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- WRKBKFRZXJRUKG-UHFFFAOYSA-N 4-hydroxy-1,3-thiazolidine-2-thione Chemical class OC1CSC(=S)N1 WRKBKFRZXJRUKG-UHFFFAOYSA-N 0.000 description 2
- JXKAUUVMXZIJNZ-UHFFFAOYSA-N 6-ethylpyridin-2-amine Chemical compound CCC1=CC=CC(N)=N1 JXKAUUVMXZIJNZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- VFJVXXLZFLLCMV-UHFFFAOYSA-N n,n-diethylethanamine;(5-methylpyridin-2-yl)carbamodithioic acid Chemical compound CCN(CC)CC.CC1=CC=C(NC(S)=S)N=C1 VFJVXXLZFLLCMV-UHFFFAOYSA-N 0.000 description 2
- AFUDIRKIAWIJJT-UHFFFAOYSA-N n-(4-methylpyridin-2-yl)carbamodithioate;triethylazanium Chemical compound CC[NH+](CC)CC.CC1=CC=NC(NC([S-])=S)=C1 AFUDIRKIAWIJJT-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SAIRZMWXVJEBMO-UHFFFAOYSA-N 1-bromo-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)CBr SAIRZMWXVJEBMO-UHFFFAOYSA-N 0.000 description 1
- QVMRSFQXWJGXRL-UHFFFAOYSA-N 1-chloro-4-methylpentan-2-one Chemical compound CC(C)CC(=O)CCl QVMRSFQXWJGXRL-UHFFFAOYSA-N 0.000 description 1
- QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 description 1
- FKAXLEKRJSNZCF-UHFFFAOYSA-N 3-(6-ethylpyridin-2-yl)-4-hydroxy-4-methyl-1,3-thiazolidine-2-thione Chemical compound CCC1=CC=CC(N2C(CSC2=S)(C)O)=N1 FKAXLEKRJSNZCF-UHFFFAOYSA-N 0.000 description 1
- KCPACMFMDRACBZ-UHFFFAOYSA-N 4-butyl-4-hydroxy-3-(6-methylpyridin-2-yl)-1,3-thiazolidine-2-thione Chemical compound CCCCC1(O)CSC(=S)N1C1=CC=CC(C)=N1 KCPACMFMDRACBZ-UHFFFAOYSA-N 0.000 description 1
- SYYBGRAWXXXMMP-UHFFFAOYSA-N 4-hydroxy-3-(6-methylpyridin-2-yl)-1,3-thiazolidine-2-thione Chemical compound CC1=CC=CC(N2C(SCC2O)=S)=N1 SYYBGRAWXXXMMP-UHFFFAOYSA-N 0.000 description 1
- VXNIASIWOMABNY-UHFFFAOYSA-N 4-hydroxy-3-(6-methylpyridin-2-yl)-4-propan-2-yl-1,3-thiazolidine-2-thione Chemical compound CC(C)C1(O)CSC(=S)N1C1=CC=CC(C)=N1 VXNIASIWOMABNY-UHFFFAOYSA-N 0.000 description 1
- XFRCYBBVWOTDKN-UHFFFAOYSA-N 4-hydroxy-3-(6-methylpyridin-2-yl)-4-propyl-1,3-thiazolidine-2-thione Chemical compound CCCC1(O)CSC(=S)N1C1=CC=CC(C)=N1 XFRCYBBVWOTDKN-UHFFFAOYSA-N 0.000 description 1
- XXWQFHCOPPVTTH-UHFFFAOYSA-N 4-hydroxy-4-(2-methylpropyl)-3-(6-methylpyridin-2-yl)-1,3-thiazolidine-2-thione Chemical compound CC(C)CC1(O)CSC(=S)N1C1=CC=CC(C)=N1 XXWQFHCOPPVTTH-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- NRTLTGGGUQIRRT-UHFFFAOYSA-N triethylazanium;bromide Chemical compound [Br-].CC[NH+](CC)CC NRTLTGGGUQIRRT-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7715072A FR2391212A1 (fr) | 1977-05-17 | 1977-05-17 | Nouveaux derives de la thiazolidine, leur preparation et les compositions qui les contiennent |
| FR7812187A FR2424275A1 (fr) | 1978-04-25 | 1978-04-25 | Nouveaux derives de l'hydroxy-4 thiazolidinethione-2, leur preparation et les compositions qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO781712L true NO781712L (no) | 1978-11-20 |
Family
ID=26220025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO78781712A NO781712L (no) | 1977-05-17 | 1978-05-16 | Fremgangsmaate for fremstilling av nye derivater av 4-hydroksytiazolidin-2-tion |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4164579A (it) |
| JP (1) | JPS5416476A (it) |
| AU (1) | AU514150B2 (it) |
| BE (1) | BE867129A (it) |
| CA (1) | CA1092120A (it) |
| DE (1) | DE2821566A1 (it) |
| ES (1) | ES469896A1 (it) |
| FI (1) | FI781567A (it) |
| GB (1) | GB1575274A (it) |
| GR (1) | GR63587B (it) |
| IE (1) | IE46828B1 (it) |
| IL (1) | IL54736A (it) |
| IT (1) | IT1096218B (it) |
| LU (1) | LU79662A1 (it) |
| NL (2) | NL7804971A (it) |
| NO (1) | NO781712L (it) |
| NZ (1) | NZ187289A (it) |
| PT (1) | PT68048B (it) |
| SE (1) | SE7805588L (it) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2441626A1 (fr) * | 1978-11-16 | 1980-06-13 | Rhone Poulenc Ind | Nouveaux derives de la perhydrothiazine-1,3 leur preparation et les medicaments qui les contiennent |
| FR2441613A1 (fr) * | 1978-11-16 | 1980-06-13 | Rhone Poulenc Ind | Nouveaux dithiocarbamates, leur preparation et les medicaments qui les contiennent |
| JPS62183810A (ja) * | 1986-02-07 | 1987-08-12 | S & O:Kk | 放電加工液を得るための液体処理方法 |
| DE19908539A1 (de) * | 1999-02-26 | 2000-08-31 | Aventis Pharma Gmbh | Polycyclische 2-Amino-Dihydrothiazolsysteme, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| CN102432444B (zh) * | 2011-11-22 | 2013-12-11 | 太仓市运通化工厂 | 一种2-溴-2-甲基丙醛的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3726880A (en) * | 1971-09-07 | 1973-04-10 | Parke Davis & Co | Organic amides and methods for their production |
| US3761485A (en) * | 1971-09-07 | 1973-09-25 | Parke Davis & Co | 3-(5-chloro-2-pyridyl)rhodanine and 3-(5-chloro-2-pyridyl)-5-(lower alkyl)rhodanines |
-
1978
- 1978-05-09 NL NL7804971A patent/NL7804971A/xx not_active Application Discontinuation
- 1978-05-09 NL NL7804977A patent/NL7804977A/xx not_active Application Discontinuation
- 1978-05-15 GR GR56236A patent/GR63587B/el unknown
- 1978-05-16 PT PT68048A patent/PT68048B/pt unknown
- 1978-05-16 NO NO78781712A patent/NO781712L/no unknown
- 1978-05-16 US US05/906,599 patent/US4164579A/en not_active Expired - Lifetime
- 1978-05-16 SE SE7805588A patent/SE7805588L/xx unknown
- 1978-05-16 LU LU79662A patent/LU79662A1/xx unknown
- 1978-05-16 JP JP5816578A patent/JPS5416476A/ja active Pending
- 1978-05-16 IL IL54736A patent/IL54736A/xx unknown
- 1978-05-16 BE BE187745A patent/BE867129A/xx unknown
- 1978-05-16 GB GB19927/78A patent/GB1575274A/en not_active Expired
- 1978-05-16 IT IT23470/78A patent/IT1096218B/it active
- 1978-05-16 AU AU36138/78A patent/AU514150B2/en not_active Expired
- 1978-05-16 ES ES469896A patent/ES469896A1/es not_active Expired
- 1978-05-16 IE IE982/78A patent/IE46828B1/en unknown
- 1978-05-16 NZ NZ187289A patent/NZ187289A/xx unknown
- 1978-05-17 FI FI781567A patent/FI781567A/fi not_active Application Discontinuation
- 1978-05-17 DE DE19782821566 patent/DE2821566A1/de not_active Withdrawn
- 1978-05-17 CA CA303,572A patent/CA1092120A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NZ187289A (en) | 1980-09-12 |
| AU514150B2 (en) | 1981-01-29 |
| GB1575274A (en) | 1980-09-17 |
| IE780982L (en) | 1978-11-17 |
| IE46828B1 (en) | 1983-10-05 |
| NL7804977A (nl) | 1978-11-21 |
| NL7804971A (nl) | 1978-11-21 |
| DE2821566A1 (de) | 1978-11-30 |
| ES469896A1 (es) | 1979-01-01 |
| SE7805588L (sv) | 1978-11-18 |
| BE867129A (fr) | 1978-11-16 |
| IT1096218B (it) | 1985-08-26 |
| AU3613878A (en) | 1979-11-22 |
| PT68048B (fr) | 1979-10-24 |
| IT7823470A0 (it) | 1978-05-16 |
| CA1092120A (fr) | 1980-12-23 |
| JPS5416476A (en) | 1979-02-07 |
| LU79662A1 (fr) | 1979-02-02 |
| GR63587B (en) | 1979-11-23 |
| US4164579A (en) | 1979-08-14 |
| PT68048A (fr) | 1978-06-01 |
| FI781567A (fi) | 1978-11-18 |
| IL54736A (en) | 1980-09-16 |
| IL54736A0 (en) | 1978-07-31 |
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