SE446532B - Bensimidazol- och bensimidazolidin-derivat - Google Patents
Bensimidazol- och bensimidazolidin-derivatInfo
- Publication number
- SE446532B SE446532B SE7902911A SE7902911A SE446532B SE 446532 B SE446532 B SE 446532B SE 7902911 A SE7902911 A SE 7902911A SE 7902911 A SE7902911 A SE 7902911A SE 446532 B SE446532 B SE 446532B
- Authority
- SE
- Sweden
- Prior art keywords
- chloro
- filtered
- sulfamyl
- amino
- group
- Prior art date
Links
- 239000007787 solid Substances 0.000 claims description 12
- -1 N3-methylguanidino group Chemical group 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 238000004458 analytical method Methods 0.000 claims description 4
- 239000002934 diuretic Substances 0.000 claims description 2
- 230000001882 diuretic effect Effects 0.000 claims description 2
- 239000003480 eluent Substances 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 239000004480 active ingredient Substances 0.000 claims 2
- 235000019687 Lamb Nutrition 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 230000003276 anti-hypertensive effect Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- YWANGSCDWBUSBK-UHFFFAOYSA-N n-(5-chloro-2-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC(Cl)=CC=C1[N+]([O-])=O YWANGSCDWBUSBK-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- ZCWXYZBQDNFULS-UHFFFAOYSA-N 5-chloro-2-nitroaniline Chemical compound NC1=CC(Cl)=CC=C1[N+]([O-])=O ZCWXYZBQDNFULS-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- SEDZBBJNRJOYHT-UHFFFAOYSA-N Cl.ClC1=C(S(N)(=O)=O)C=C2NC(NC(=N)N)=NC2=C1 Chemical compound Cl.ClC1=C(S(N)(=O)=O)C=C2NC(NC(=N)N)=NC2=C1 SEDZBBJNRJOYHT-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- MUUQHCOAOLLHIL-UHFFFAOYSA-N n-(3-chlorophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(Cl)=C1 MUUQHCOAOLLHIL-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- QVMFLESIHLVMFY-UHFFFAOYSA-N 2-amino-6-chloro-3H-benzimidazole-5-sulfonamide hydrobromide Chemical compound Br.ClC1=C(S(N)(=O)=O)C=C2NC(N)=NC2=C1 QVMFLESIHLVMFY-UHFFFAOYSA-N 0.000 description 2
- JJWXBXFGEPDWQX-UHFFFAOYSA-N 4,5-diamino-2-chlorobenzenesulfonamide Chemical compound NC1=CC(Cl)=C(S(N)(=O)=O)C=C1N JJWXBXFGEPDWQX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 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 description 1
- QXNAJOBIZGDYNS-UHFFFAOYSA-N 1-(5-bromo-6-sulfamoyl-2,3-dihydro-1h-benzimidazol-2-yl)-2-methylguanidine Chemical compound BrC1=C(S(N)(=O)=O)C=C2NC(NC(=N)NC)NC2=C1 QXNAJOBIZGDYNS-UHFFFAOYSA-N 0.000 description 1
- KFWHLBDERZMVNM-UHFFFAOYSA-N 1-(5-chloro-6-sulfamoyl-1h-benzimidazol-2-yl)-2-methylguanidine Chemical compound ClC1=C(S(N)(=O)=O)C=C2NC(NC(=N)NC)=NC2=C1 KFWHLBDERZMVNM-UHFFFAOYSA-N 0.000 description 1
- ZPXVZJSQJLEDGL-UHFFFAOYSA-N 2-(5-bromo-6-sulfamoyl-1h-benzimidazol-2-yl)guanidine Chemical compound BrC1=C(S(N)(=O)=O)C=C2NC(NC(=N)N)=NC2=C1 ZPXVZJSQJLEDGL-UHFFFAOYSA-N 0.000 description 1
- PVIGLFFBEJYFAG-UHFFFAOYSA-N 2-(5-bromo-6-sulfamoyl-2,3-dihydro-1h-benzimidazol-2-yl)guanidine Chemical compound BrC1=C(S(N)(=O)=O)C=C2NC(NC(=N)N)NC2=C1 PVIGLFFBEJYFAG-UHFFFAOYSA-N 0.000 description 1
- SEXLJZNKVUXSIG-UHFFFAOYSA-N 2-(6-fluoro-5-sulfamoyl-1h-benzimidazol-2-yl)guanidine Chemical compound FC1=C(S(N)(=O)=O)C=C2NC(NC(=N)N)=NC2=C1 SEXLJZNKVUXSIG-UHFFFAOYSA-N 0.000 description 1
- ASBYMLQXGAHKJL-UHFFFAOYSA-N 2-amino-6-bromo-2,3-dihydro-1h-benzimidazole-5-sulfonamide Chemical compound BrC1=C(S(N)(=O)=O)C=C2NC(N)NC2=C1 ASBYMLQXGAHKJL-UHFFFAOYSA-N 0.000 description 1
- WRXLXZPAKYVLFQ-UHFFFAOYSA-N 2-amino-6-bromo-3h-benzimidazole-5-sulfonamide Chemical compound BrC1=C(S(N)(=O)=O)C=C2NC(N)=NC2=C1 WRXLXZPAKYVLFQ-UHFFFAOYSA-N 0.000 description 1
- YYMJLFVIPZIAFY-UHFFFAOYSA-N 2-amino-6-chloro-2,3-dihydro-1h-benzimidazole-5-sulfonamide Chemical compound ClC1=C(S(N)(=O)=O)C=C2NC(N)NC2=C1 YYMJLFVIPZIAFY-UHFFFAOYSA-N 0.000 description 1
- WPRIQACCRBIARE-UHFFFAOYSA-N 2-amino-6-fluoro-1h-benzimidazole-5-sulfonamide Chemical compound FC1=C(S(N)(=O)=O)C=C2NC(N)=NC2=C1 WPRIQACCRBIARE-UHFFFAOYSA-N 0.000 description 1
- NRZQLPCCBZGDAO-UHFFFAOYSA-N 6-chloro-2-phenyl-3h-benzimidazole-5-sulfonamide Chemical compound N=1C=2C=C(Cl)C(S(=O)(=O)N)=CC=2NC=1C1=CC=CC=C1 NRZQLPCCBZGDAO-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 241000176030 Nanna Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- JWOSTXBESVWMJW-UHFFFAOYSA-N cyclohexyl sulfamate Chemical class NS(=O)(=O)OC1CCCCC1 JWOSTXBESVWMJW-UHFFFAOYSA-N 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-L ethanedisulfonate group Chemical class C(CS(=O)(=O)[O-])S(=O)(=O)[O-] AFAXGSQYZLGZPG-UHFFFAOYSA-L 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000011110 re-filtration Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000002700 urine Anatomy 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
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
-
- 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
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89504878A | 1978-04-10 | 1978-04-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7902911L SE7902911L (sv) | 1979-10-11 |
| SE446532B true SE446532B (sv) | 1986-09-22 |
Family
ID=25403870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7902911A SE446532B (sv) | 1978-04-10 | 1979-04-02 | Bensimidazol- och bensimidazolidin-derivat |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS54138561A (cs) |
| AT (1) | AT372951B (cs) |
| AU (1) | AU531086B2 (cs) |
| BE (1) | BE875425A (cs) |
| CA (1) | CA1126280A (cs) |
| DE (1) | DE2914084A1 (cs) |
| DK (1) | DK139079A (cs) |
| ES (1) | ES479446A1 (cs) |
| FI (1) | FI74461C (cs) |
| FR (1) | FR2422644A1 (cs) |
| GB (1) | GB2018766B (cs) |
| GR (1) | GR68483B (cs) |
| IL (1) | IL57105A (cs) |
| IT (1) | IT1193755B (cs) |
| NL (1) | NL7902802A (cs) |
| NZ (1) | NZ190136A (cs) |
| PT (1) | PT69458A (cs) |
| SE (1) | SE446532B (cs) |
| ZA (1) | ZA791726B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102070466A (zh) * | 2010-12-28 | 2011-05-25 | 天津市筠凯化工科技有限公司 | 5-氯-2-硝基苯胺制备方法 |
| CN108558712A (zh) * | 2018-06-20 | 2018-09-21 | 新乡市锦源化工有限公司 | 一种以乙酰苯胺为原料合成高纯度对氨基苯磺酰胺的方法及对氨基苯磺酰胺 |
| CN110305018B (zh) * | 2019-06-06 | 2022-07-15 | 浙江普洛家园药业有限公司 | 一种3-溴-2-氟硝基苯的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH404675A (de) * | 1961-06-29 | 1965-12-31 | Siegfried Ag | Verfahren zur Herstellung neuer heterocyclischer Sulfonamidoverbindungen |
| FR1469504A (fr) * | 1964-10-22 | 1967-02-17 | Fisons Pest Control Ltd | Composés insecticides |
| FR1477792A (fr) * | 1965-03-24 | 1967-04-21 | Fisons Pest Control Ltd | Nouveaux benzimidazoles |
| GB1163711A (en) * | 1966-01-13 | 1969-09-10 | Fisons Pest Control Ltd | Substituted Benzimidazoles and Biocidally-Active Compositions |
| GB1356244A (en) * | 1970-07-29 | 1974-06-12 | Fisons Ltd | Substituted benzimidazole parasiticides |
-
1979
- 1979-03-26 CA CA324,146A patent/CA1126280A/en not_active Expired
- 1979-04-02 FI FI791083A patent/FI74461C/fi not_active IP Right Cessation
- 1979-04-02 SE SE7902911A patent/SE446532B/sv not_active IP Right Cessation
- 1979-04-02 AU AU45675/79A patent/AU531086B2/en not_active Ceased
- 1979-04-03 GR GR58771A patent/GR68483B/el unknown
- 1979-04-04 DK DK139079A patent/DK139079A/da not_active IP Right Cessation
- 1979-04-06 GB GB7912255A patent/GB2018766B/en not_active Expired
- 1979-04-07 DE DE19792914084 patent/DE2914084A1/de not_active Withdrawn
- 1979-04-09 PT PT69458A patent/PT69458A/pt unknown
- 1979-04-09 JP JP4211979A patent/JPS54138561A/ja active Granted
- 1979-04-09 ES ES479446A patent/ES479446A1/es not_active Expired
- 1979-04-09 BE BE0/194480A patent/BE875425A/xx not_active IP Right Cessation
- 1979-04-09 NZ NZ190136A patent/NZ190136A/xx unknown
- 1979-04-09 AT AT0263379A patent/AT372951B/de not_active IP Right Cessation
- 1979-04-09 FR FR7908945A patent/FR2422644A1/fr active Granted
- 1979-04-10 NL NL7902802A patent/NL7902802A/xx not_active Application Discontinuation
- 1979-04-10 IT IT48686/79A patent/IT1193755B/it active
- 1979-04-10 ZA ZA791726A patent/ZA791726B/xx unknown
- 1979-04-22 IL IL57105A patent/IL57105A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT1193755B (it) | 1988-08-24 |
| IL57105A (en) | 1983-10-31 |
| JPS54138561A (en) | 1979-10-27 |
| ES479446A1 (es) | 1979-08-01 |
| FI74461B (fi) | 1987-10-30 |
| FR2422644B1 (cs) | 1982-12-17 |
| GB2018766A (en) | 1979-10-24 |
| AT372951B (de) | 1983-12-12 |
| DE2914084A1 (de) | 1979-10-25 |
| PT69458A (en) | 1979-05-01 |
| NL7902802A (nl) | 1979-10-12 |
| NZ190136A (en) | 1982-11-23 |
| ATA263379A (de) | 1983-04-15 |
| GR68483B (cs) | 1982-01-04 |
| AU4567579A (en) | 1979-10-18 |
| IT7948686A0 (it) | 1979-04-10 |
| CA1126280A (en) | 1982-06-22 |
| FI74461C (fi) | 1988-02-08 |
| IL57105A0 (en) | 1979-07-25 |
| BE875425A (fr) | 1979-07-31 |
| GB2018766B (en) | 1982-09-22 |
| SE7902911L (sv) | 1979-10-11 |
| AU531086B2 (en) | 1983-08-11 |
| DK139079A (da) | 1979-10-11 |
| FR2422644A1 (fr) | 1979-11-09 |
| ZA791726B (en) | 1980-05-28 |
| FI791083A7 (fi) | 1979-10-11 |
| JPH0250904B2 (cs) | 1990-11-05 |
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