CA1126280A - Benzimidazole and benzimidazolidine derivatives with diuretic and antihypertensive activity - Google Patents
Benzimidazole and benzimidazolidine derivatives with diuretic and antihypertensive activityInfo
- Publication number
- CA1126280A CA1126280A CA324,146A CA324146A CA1126280A CA 1126280 A CA1126280 A CA 1126280A CA 324146 A CA324146 A CA 324146A CA 1126280 A CA1126280 A CA 1126280A
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- chloro
- sulfamyl
- lower alkyl
- benzimidazole
- 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
- 230000003276 anti-hypertensive effect Effects 0.000 title abstract description 3
- 239000002934 diuretic Substances 0.000 title abstract description 3
- 230000001882 diuretic effect Effects 0.000 title abstract description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title 1
- MXMZCLLIUQEKSN-UHFFFAOYSA-N benzimidazoline Chemical class C1=CC=C2NCNC2=C1 MXMZCLLIUQEKSN-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- -1 amino, substituted amino, guanidino Chemical group 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical group 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 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 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- NIIPOMKMZZUVKA-UHFFFAOYSA-N 1-cyano-1-methylguanidine Chemical compound N#CN(C)C(N)=N NIIPOMKMZZUVKA-UHFFFAOYSA-N 0.000 claims description 2
- 229960000583 acetic acid Drugs 0.000 claims description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 8
- 239000000126 substance Substances 0.000 claims 5
- 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 claims 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 4
- 125000005157 alkyl carboxy group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 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 claims 1
- TVAZJWNYCUFLHK-UHFFFAOYSA-N Cl.ClC1=C(S(N)(=O)=O)C=C2NC(NC(=N)NC)=NC2=C1 Chemical compound Cl.ClC1=C(S(N)(=O)=O)C=C2NC(NC(=N)NC)=NC2=C1 TVAZJWNYCUFLHK-UHFFFAOYSA-N 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims 1
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 19
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 17
- 125000003118 aryl group Chemical group 0.000 abstract description 15
- 239000001257 hydrogen Substances 0.000 abstract description 13
- 125000003107 substituted aryl group Chemical group 0.000 abstract description 10
- 150000002431 hydrogen Chemical class 0.000 abstract description 9
- 125000002252 acyl group Chemical group 0.000 abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 5
- 125000000547 substituted alkyl group Chemical group 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 18
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- OPGUZRRLMQSMAQ-UHFFFAOYSA-N 5-(4-methoxyphenyl)-1-phenylbenzimidazole Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N(C=N2)C=3C=CC=CC=3)C2=C1 OPGUZRRLMQSMAQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910017974 NH40H Inorganic materials 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 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
- VWUWVYJSLNIUEL-UHFFFAOYSA-N 2-amino-6-bromo-3-(2-chlorophenyl)benzimidazole-5-sulfonamide Chemical compound NC1=NC2=CC(Br)=C(S(N)(=O)=O)C=C2N1C1=CC=CC=C1Cl VWUWVYJSLNIUEL-UHFFFAOYSA-N 0.000 description 1
- CRWLLWGOVNSWQY-UHFFFAOYSA-N 2-amino-6-bromo-3-(2-methoxyphenyl)benzimidazole-5-sulfonamide Chemical compound COC1=CC=CC=C1N1C2=CC(S(N)(=O)=O)=C(Br)C=C2N=C1N CRWLLWGOVNSWQY-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
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- ZCWXYZBQDNFULS-UHFFFAOYSA-N 5-chloro-2-nitroaniline Chemical compound NC1=CC(Cl)=CC=C1[N+]([O-])=O ZCWXYZBQDNFULS-UHFFFAOYSA-N 0.000 description 1
- IUKJYOCTKFWPSO-UHFFFAOYSA-N 6-chloro-2-(furan-2-ylmethylamino)-2,3-dihydro-1h-benzimidazole-5-sulfonamide Chemical compound N1C=2C=C(Cl)C(S(=O)(=O)N)=CC=2NC1NCC1=CC=CO1 IUKJYOCTKFWPSO-UHFFFAOYSA-N 0.000 description 1
- HPMCKMUUNDDFJQ-UHFFFAOYSA-N 6-chloro-2-phenyl-2,3-dihydro-1h-benzimidazole-5-sulfonamide Chemical compound N1C=2C=C(Cl)C(S(=O)(=O)N)=CC=2NC1C1=CC=CC=C1 HPMCKMUUNDDFJQ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 101150068326 bro1 gene Proteins 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- JWOSTXBESVWMJW-UHFFFAOYSA-N cyclohexyl sulfamate Chemical class NS(=O)(=O)OC1CCCCC1 JWOSTXBESVWMJW-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000013222 sprague-dawley male rat 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
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003892 tartrate salts Chemical class 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89504878A | 1978-04-10 | 1978-04-10 | |
| US895,048 | 1978-04-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1126280A true CA1126280A (en) | 1982-06-22 |
Family
ID=25403870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA324,146A Expired CA1126280A (en) | 1978-04-10 | 1979-03-26 | Benzimidazole and benzimidazolidine derivatives with diuretic and antihypertensive activity |
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 |
| SE446532B (sv) | 1986-09-22 |
| 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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| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |