DE2257311A1 - Benzimidazolyl-aminoimidazoline, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate - Google Patents
Benzimidazolyl-aminoimidazoline, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparateInfo
- Publication number
- DE2257311A1 DE2257311A1 DE2257311A DE2257311A DE2257311A1 DE 2257311 A1 DE2257311 A1 DE 2257311A1 DE 2257311 A DE2257311 A DE 2257311A DE 2257311 A DE2257311 A DE 2257311A DE 2257311 A1 DE2257311 A1 DE 2257311A1
- Authority
- DE
- Germany
- Prior art keywords
- amino
- imidazoline
- benzimidazolyl
- aminoimidazolines
- hydrogen
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims description 45
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 5
- -1 Methoxy, methyl Chemical group 0.000 claims description 87
- 239000012458 free base Substances 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 19
- BGYJQMRDFPLGBJ-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)-4,5-dihydroimidazol-1-amine Chemical class NN1CCN=C1C1=NC2=CC=CC=C2N1 BGYJQMRDFPLGBJ-UHFFFAOYSA-N 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 229910021645 metal ion Inorganic materials 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- GCHHYTZTTDCGLJ-UHFFFAOYSA-N 2-(5,6-dichloro-1h-benzimidazol-2-yl)-4,5-dihydroimidazol-1-amine Chemical compound NN1CCN=C1C1=NC2=CC(Cl)=C(Cl)C=C2N1 GCHHYTZTTDCGLJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims description 2
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 3
- SIHDEOIVINNENC-UHFFFAOYSA-N 2-(4,5,6-trichloro-1h-benzimidazol-2-yl)-4,5-dihydroimidazol-1-amine Chemical compound NN1CCN=C1C1=NC2=C(Cl)C(Cl)=C(Cl)C=C2N1 SIHDEOIVINNENC-UHFFFAOYSA-N 0.000 claims 1
- FZSCVAANHLZQMA-UHFFFAOYSA-N 2-(6-bromo-1H-benzimidazol-2-yl)-4,5-dihydroimidazol-1-amine Chemical compound BrC1=CC2=C(N=C(N2)C=2N(CCN=2)N)C=C1 FZSCVAANHLZQMA-UHFFFAOYSA-N 0.000 claims 1
- QXNDIGKDSGJBTE-UHFFFAOYSA-N 2-(6-chloro-1h-benzimidazol-2-yl)-4,5-dihydroimidazol-1-amine Chemical compound NN1CCN=C1C1=NC2=CC=C(Cl)C=C2N1 QXNDIGKDSGJBTE-UHFFFAOYSA-N 0.000 claims 1
- CCEGNMHJNVWZNU-UHFFFAOYSA-N 2-n-(4,5-dihydro-1h-imidazol-2-yl)-3h-benzimidazole-2,5-diamine Chemical compound N1C2=CC(N)=CC=C2N=C1NC1=NCCN1 CCEGNMHJNVWZNU-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- FQQAXLOKQCCFHT-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)-1h-benzimidazol-2-amine Chemical compound N1CCN=C1NC1=NC2=CC=CC=C2N1 FQQAXLOKQCCFHT-UHFFFAOYSA-N 0.000 claims 1
- KZHOPFZCMQYNKZ-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)-6-methoxy-1h-benzimidazol-2-amine Chemical compound N1C2=CC(OC)=CC=C2N=C1NC1=NCCN1 KZHOPFZCMQYNKZ-UHFFFAOYSA-N 0.000 claims 1
- SGTVEKFVBDFJFA-UHFFFAOYSA-N n-[2-(1-amino-4,5-dihydroimidazol-2-yl)-3h-benzimidazol-5-yl]acetamide Chemical compound N1C2=CC(NC(=O)C)=CC=C2N=C1C1=NCCN1N SGTVEKFVBDFJFA-UHFFFAOYSA-N 0.000 claims 1
- LBQAJLBSGOBDQF-UHFFFAOYSA-N nitro azanylidynemethanesulfonate Chemical group [O-][N+](=O)OS(=O)(=O)C#N LBQAJLBSGOBDQF-UHFFFAOYSA-N 0.000 claims 1
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- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 15
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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- JJWCTKUQWXYIIU-UHFFFAOYSA-N 2-Benzimidazolylguanidine Chemical compound C1=CC=C2NC(N=C(N)N)=NC2=C1 JJWCTKUQWXYIIU-UHFFFAOYSA-N 0.000 description 4
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- ACGDKVXYNVEAGU-UHFFFAOYSA-N guanethidine Chemical compound NC(N)=NCCN1CCCCCCC1 ACGDKVXYNVEAGU-UHFFFAOYSA-N 0.000 description 4
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- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 229940035339 tri-chlor Drugs 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 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
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5449871A GB1410017A (en) | 1971-11-24 | 1971-11-24 | Benzimidazole derivatives |
| US30871972A | 1972-11-22 | 1972-11-22 | |
| US05/511,227 US3935314A (en) | 1971-11-24 | 1974-10-02 | Anti-hypertensive compositions of benzimidazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2257311A1 true DE2257311A1 (de) | 1973-06-07 |
Family
ID=27260358
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2257311A Pending DE2257311A1 (de) | 1971-11-24 | 1972-11-22 | Benzimidazolyl-aminoimidazoline, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate |
| DE2257312A Pending DE2257312A1 (de) | 1971-11-24 | 1972-11-22 | 2-aminobenzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2257312A Pending DE2257312A1 (de) | 1971-11-24 | 1972-11-22 | 2-aminobenzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3935314A (enExample) |
| JP (3) | JPS4862764A (enExample) |
| AT (1) | AT319938B (enExample) |
| AU (1) | AU4916772A (enExample) |
| BE (2) | BE791907A (enExample) |
| DE (2) | DE2257311A1 (enExample) |
| FR (2) | FR2160994B1 (enExample) |
| GB (1) | GB1410017A (enExample) |
| NL (2) | NL7215919A (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2816627A1 (de) * | 1978-04-17 | 1979-10-25 | Beiersdorf Ag | 2-(n-amino-isoindolinyl)-imidazolin und verfahren zu seiner herstellung |
| DE2905501A1 (de) * | 1979-02-14 | 1980-08-28 | Beiersdorf Ag | Neue kondensierte, stickstoffhaltige heterocyclische verbindungen und verfahren zu deren herstellung |
| US4297490A (en) | 1977-01-14 | 1981-10-27 | Sandoz Ltd. | Bicyclic heterocyclic amino derivatives |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5478858A (en) * | 1993-12-17 | 1995-12-26 | The Procter & Gamble Company | 5-(2-imidazolinylamino) benzimidazole compounds useful as alpha-2 adrenoceptor agonists |
| AU704972B2 (en) | 1994-08-04 | 1999-05-13 | H. Lundbeck A/S | Novel benzimidazole derivatives |
| US6495583B1 (en) | 1997-03-25 | 2002-12-17 | Synaptic Pharmaceutical Corporation | Benzimidazole derivatives |
| WO2011058139A1 (en) * | 2009-11-12 | 2011-05-19 | Selvita Sp. Z O. O. | A compound, a process for its preparation, a pharmaceutical composition, use of a compound, a method for modulating or regulating serine/threonine kinases and a serine/threonine kinases modulating agent |
| US8604217B2 (en) * | 2009-11-12 | 2013-12-10 | Selvita S.A. | Compound, a process for its preparation, a pharmaceutical composition, use of a compound, a method for modulating or regulating serine/threonine kinases and a serine/threonine kinases modulating agent |
| US20150203812A1 (en) * | 2014-01-20 | 2015-07-23 | Francesco Tombola | Inhibitors of Voltage Gated Ion Channels |
| TWI685338B (zh) * | 2017-12-14 | 2020-02-21 | 柯瑞 伊里阿斯 Ｊ | 使用非可吸收性口服投予之化合物之包括第2型糖尿病、脂肪肝炎及相關病況之人類代謝症候群之預防及治療 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3749789A (en) * | 1970-02-27 | 1973-07-31 | Merck & Co Inc | Anthelmintic compositions containing benzimidazoles and method of use |
| FR2116246B1 (enExample) * | 1970-12-01 | 1974-03-22 | Delalande Sa | |
| US3749734A (en) * | 1971-07-12 | 1973-07-31 | Merck & Co Inc | 1-cyanobenzimidazoles |
| US3738994A (en) * | 1971-08-13 | 1973-06-12 | Merck & Co Inc | 2-cyano-polyhalobenzimidazoles |
| US3760081A (en) * | 1972-01-24 | 1973-09-18 | Upjohn Co | Method of treatment |
-
0
- BE BE791908D patent/BE791908A/xx unknown
- BE BE791907D patent/BE791907A/xx unknown
-
1971
- 1971-11-24 GB GB5449871A patent/GB1410017A/en not_active Expired
-
1972
- 1972-11-21 JP JP47117663A patent/JPS4862764A/ja active Pending
- 1972-11-21 JP JP47117662A patent/JPS4862763A/ja active Pending
- 1972-11-21 AT AT989572A patent/AT319938B/de not_active IP Right Cessation
- 1972-11-21 JP JP47117661A patent/JPS4862762A/ja active Pending
- 1972-11-22 DE DE2257311A patent/DE2257311A1/de active Pending
- 1972-11-22 DE DE2257312A patent/DE2257312A1/de active Pending
- 1972-11-22 AU AU49167/72A patent/AU4916772A/en not_active Expired
- 1972-11-23 NL NL7215919A patent/NL7215919A/xx unknown
- 1972-11-23 FR FR7241623A patent/FR2160994B1/fr not_active Expired
- 1972-11-23 FR FR7241624A patent/FR2160995B1/fr not_active Expired
- 1972-11-23 NL NL7215920A patent/NL7215920A/xx unknown
-
1974
- 1974-10-02 US US05/511,227 patent/US3935314A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4297490A (en) | 1977-01-14 | 1981-10-27 | Sandoz Ltd. | Bicyclic heterocyclic amino derivatives |
| DE2816627A1 (de) * | 1978-04-17 | 1979-10-25 | Beiersdorf Ag | 2-(n-amino-isoindolinyl)-imidazolin und verfahren zu seiner herstellung |
| DE2905501A1 (de) * | 1979-02-14 | 1980-08-28 | Beiersdorf Ag | Neue kondensierte, stickstoffhaltige heterocyclische verbindungen und verfahren zu deren herstellung |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1410017A (en) | 1975-10-15 |
| NL7215920A (enExample) | 1973-05-28 |
| FR2160995B1 (enExample) | 1975-10-17 |
| DE2257312A1 (de) | 1973-06-07 |
| FR2160995A1 (enExample) | 1973-07-06 |
| AU4916772A (en) | 1974-05-23 |
| JPS4862762A (enExample) | 1973-09-01 |
| BE791908A (fr) | 1973-05-24 |
| US3935314A (en) | 1976-01-27 |
| JPS4862763A (enExample) | 1973-09-01 |
| JPS4862764A (enExample) | 1973-09-01 |
| FR2160994A1 (enExample) | 1973-07-06 |
| BE791907A (fr) | 1973-05-24 |
| NL7215919A (enExample) | 1973-05-28 |
| FR2160994B1 (enExample) | 1976-05-21 |
| AT319938B (de) | 1975-01-10 |
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