DD154976A5 - Verfahren zur herstellung von alkylthiobenzimidazolen - Google Patents
Verfahren zur herstellung von alkylthiobenzimidazolen Download PDFInfo
- Publication number
- DD154976A5 DD154976A5 DD80225693A DD22569380A DD154976A5 DD 154976 A5 DD154976 A5 DD 154976A5 DD 80225693 A DD80225693 A DD 80225693A DD 22569380 A DD22569380 A DD 22569380A DD 154976 A5 DD154976 A5 DD 154976A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- benzimidazole
- reacted
- sulfonic acid
- amino
- preparation
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 16
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims abstract description 7
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 5
- 239000012320 chlorinating reagent Substances 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 150000001350 alkyl halides Chemical class 0.000 claims abstract description 3
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 claims abstract 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims abstract 2
- 150000001556 benzimidazoles Chemical class 0.000 claims abstract 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 150000002739 metals Chemical class 0.000 claims description 4
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 11
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 150000004702 methyl esters Chemical class 0.000 abstract description 2
- 230000000507 anthelmentic effect Effects 0.000 abstract 1
- FPAKSOQSBLHGDU-UHFFFAOYSA-N methyl n-(6-chlorosulfonyl-1h-benzimidazol-2-yl)carbamate Chemical compound C1=C(S(Cl)(=O)=O)C=C2NC(NC(=O)OC)=NC2=C1 FPAKSOQSBLHGDU-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 20
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 229910052717 sulfur Inorganic materials 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000005457 ice water Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- -1 alkyl chloroformate Chemical compound 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- UBHQQKNVFBINEJ-UHFFFAOYSA-N COC(=O)C1=NC2=C(N1N)C=CC(=C2)S(=O)(=O)O Chemical compound COC(=O)C1=NC2=C(N1N)C=CC(=C2)S(=O)(=O)O UBHQQKNVFBINEJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- OUIKOKUYWFLQGD-UHFFFAOYSA-N benzene-1,2-diol;trichlorophosphane Chemical compound ClP(Cl)Cl.OC1=CC=CC=C1O OUIKOKUYWFLQGD-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Photoreceptors In Electrophotography (AREA)
- Paper (AREA)
- Lubricants (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79CI1993A HU182782B (en) | 1979-12-04 | 1979-12-04 | Process for producing alkylthio-benzimidazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD154976A5 true DD154976A5 (de) | 1982-05-05 |
Family
ID=10994778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD80225693A DD154976A5 (de) | 1979-12-04 | 1980-12-03 | Verfahren zur herstellung von alkylthiobenzimidazolen |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4368328A (cs) |
| EP (1) | EP0031473B1 (cs) |
| JP (1) | JPS5695172A (cs) |
| AT (1) | ATE7692T1 (cs) |
| CS (1) | CS237317B2 (cs) |
| DD (1) | DD154976A5 (cs) |
| DE (1) | DE3068071D1 (cs) |
| DK (1) | DK160423C (cs) |
| FI (1) | FI74278C (cs) |
| GR (1) | GR72924B (cs) |
| HU (1) | HU182782B (cs) |
| IL (1) | IL61585A (cs) |
| PL (1) | PL128450B1 (cs) |
| SU (2) | SU1126208A3 (cs) |
| YU (1) | YU42712B (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU196185B (en) * | 1984-12-19 | 1988-10-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing benzimidazol-thiol derivatives |
| HU200167B (en) * | 1987-07-30 | 1990-04-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing substituted benzimidazole derivatives |
| DE4340915A1 (de) * | 1993-02-23 | 1994-08-25 | Heidelberger Druckmasch Ag | Auswechselbare Andrückhülse |
| CN1056368C (zh) * | 1996-04-17 | 2000-09-13 | 常州市合成材料厂 | 阿苯达唑的制备工艺 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2654762A (en) * | 1951-07-14 | 1953-10-06 | Ciba Pharm Prod Inc | Iodinated substituted mercaptoimidazoles |
| DE2441202C2 (de) * | 1974-08-28 | 1986-05-28 | Hoechst Ag, 6230 Frankfurt | 2-Carbalkoxyamino-benzimidazolyl-5(6)-sulfonsäure-phenylester, Verfahren zu ihrer Herstellung und diese enthaltende anthelmintische Mittel |
| US4080461A (en) * | 1975-11-03 | 1978-03-21 | Syntex (U.S.A.) Inc. | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
| SE443977B (sv) * | 1977-05-10 | 1986-03-17 | Chinoin Gyogyszer Es Vegyeszet | Forfarande for framstellning av 5(6)-tio-bensimidazolderivat |
-
1979
- 1979-12-04 HU HU79CI1993A patent/HU182782B/hu not_active IP Right Cessation
-
1980
- 1980-11-28 IL IL61585A patent/IL61585A/xx not_active IP Right Cessation
- 1980-11-28 FI FI803706A patent/FI74278C/fi not_active IP Right Cessation
- 1980-11-28 CS CS808283A patent/CS237317B2/cs unknown
- 1980-12-02 DE DE8080107505T patent/DE3068071D1/de not_active Expired
- 1980-12-02 AT AT80107505T patent/ATE7692T1/de active
- 1980-12-02 EP EP80107505A patent/EP0031473B1/de not_active Expired
- 1980-12-03 GR GR63541A patent/GR72924B/el unknown
- 1980-12-03 DD DD80225693A patent/DD154976A5/de not_active IP Right Cessation
- 1980-12-03 PL PL1980228234A patent/PL128450B1/pl unknown
- 1980-12-03 US US06/212,628 patent/US4368328A/en not_active Expired - Lifetime
- 1980-12-03 DK DK515980A patent/DK160423C/da not_active IP Right Cessation
- 1980-12-03 YU YU3056/80A patent/YU42712B/xx unknown
- 1980-12-04 JP JP17030880A patent/JPS5695172A/ja active Granted
- 1980-12-04 SU SU803212701A patent/SU1126208A3/ru active
-
1981
- 1981-04-13 SU SU813269655A patent/SU981316A1/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5695172A (en) | 1981-08-01 |
| YU42712B (en) | 1988-12-31 |
| HU182782B (en) | 1984-03-28 |
| DE3068071D1 (en) | 1984-07-05 |
| IL61585A0 (en) | 1980-12-31 |
| EP0031473B1 (de) | 1984-05-30 |
| DK160423C (da) | 1991-09-16 |
| ATE7692T1 (de) | 1984-06-15 |
| YU305680A (en) | 1983-10-31 |
| SU1126208A3 (ru) | 1984-11-23 |
| SU981316A1 (ru) | 1982-12-15 |
| PL228234A1 (cs) | 1981-08-21 |
| IL61585A (en) | 1986-04-29 |
| JPS6337103B2 (cs) | 1988-07-22 |
| EP0031473A1 (de) | 1981-07-08 |
| PL128450B1 (en) | 1984-01-31 |
| DK160423B (da) | 1991-03-11 |
| US4368328A (en) | 1983-01-11 |
| FI803706L (fi) | 1981-06-05 |
| GR72924B (cs) | 1984-01-11 |
| CS237317B2 (en) | 1985-07-16 |
| DK515980A (da) | 1981-06-05 |
| FI74278C (fi) | 1988-01-11 |
| FI74278B (fi) | 1987-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |