CA1084933A - 5,6-dimethoxy-2-substituted benzimidazole compounds - Google Patents
5,6-dimethoxy-2-substituted benzimidazole compoundsInfo
- Publication number
- CA1084933A CA1084933A CA291,154A CA291154A CA1084933A CA 1084933 A CA1084933 A CA 1084933A CA 291154 A CA291154 A CA 291154A CA 1084933 A CA1084933 A CA 1084933A
- Authority
- CA
- Canada
- Prior art keywords
- dimethoxy
- benzimidazole
- benzyl
- tetrahydro
- preparing
- 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
- -1 5,6-dimethoxy-2-substituted benzimidazole compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract 4
- 150000003839 salts Chemical class 0.000 claims abstract 4
- CEIXWJHURKEBMQ-UHFFFAOYSA-N Heliamine Chemical compound C1CNCC2=C1C=C(OC)C(OC)=C2 CEIXWJHURKEBMQ-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 5
- DVFRGNSDKWHLEZ-UHFFFAOYSA-N 2-chloro-5,6-dimethoxy-1h-benzimidazole Chemical compound C1=C(OC)C(OC)=CC2=C1NC(Cl)=N2 DVFRGNSDKWHLEZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 6
- WWITWDFTQWYARQ-UHFFFAOYSA-N 2-(5,6-dimethoxy-1h-benzimidazol-2-yl)-6,7-dimethoxy-3,4-dihydro-1h-isoquinoline Chemical compound COC1=C(OC)C=C2NC(N3CCC=4C=C(C(=CC=4C3)OC)OC)=NC2=C1 WWITWDFTQWYARQ-UHFFFAOYSA-N 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- ABGXADJDTPFFSZ-UHFFFAOYSA-N 4-benzylpiperidine Chemical compound C=1C=CC=CC=1CC1CCNCC1 ABGXADJDTPFFSZ-UHFFFAOYSA-N 0.000 claims 2
- BTWUUHKQHOSMIN-UHFFFAOYSA-N 5,6-dimethoxy-1h-benzimidazole Chemical compound C1=C(OC)C(OC)=CC2=C1NC=N2 BTWUUHKQHOSMIN-UHFFFAOYSA-N 0.000 claims 1
- 229940030600 antihypertensive agent Drugs 0.000 abstract description 2
- 239000002220 antihypertensive agent Substances 0.000 abstract description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 230000001631 hypertensive effect Effects 0.000 description 2
- FARSPAVQUKTXLF-UHFFFAOYSA-N 1h-benzimidazol-1-ium;chloride Chemical compound Cl.C1=CC=C2NC=NC2=C1 FARSPAVQUKTXLF-UHFFFAOYSA-N 0.000 description 1
- PPCWDOKVYNKIHV-UHFFFAOYSA-N 2,4-dimethoxy-1h-benzimidazole Chemical compound C1=CC(OC)=C2NC(OC)=NC2=C1 PPCWDOKVYNKIHV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US746,656 | 1976-12-02 | ||
| US05/746,656 US4088765A (en) | 1976-12-02 | 1976-12-02 | 5,6-Dimethoxy-2-heterocyclic benzimidazoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1084933A true CA1084933A (en) | 1980-09-02 |
Family
ID=25001774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA291,154A Expired CA1084933A (en) | 1976-12-02 | 1977-11-17 | 5,6-dimethoxy-2-substituted benzimidazole compounds |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4088765A (Sortimente) |
| JP (1) | JPS5371081A (Sortimente) |
| CA (1) | CA1084933A (Sortimente) |
| FR (1) | FR2372825A1 (Sortimente) |
| GB (1) | GB1573550A (Sortimente) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6867209B1 (en) | 1998-05-22 | 2005-03-15 | Scios, Inc. | Indole-type derivatives as inhibitors of p38 kinase |
| US6448257B1 (en) | 1998-05-22 | 2002-09-10 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
| US6589954B1 (en) * | 1998-05-22 | 2003-07-08 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
| US6340685B1 (en) | 1998-05-22 | 2002-01-22 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
| US6130235A (en) * | 1998-05-22 | 2000-10-10 | Scios Inc. | Compounds and methods to treat cardiac failure and other disorders |
| IL146309A (en) | 1999-05-21 | 2008-03-20 | Scios Inc | Derivatives of the indole type and pharmaceutical preparations containing them as inhibitors of kinase p38 |
| AU2007271243A1 (en) * | 2006-07-03 | 2008-01-10 | Neurosearch A/S | Combinations of monoamine reuptake inhibitors and potassium channel activators |
-
1976
- 1976-12-02 US US05/746,656 patent/US4088765A/en not_active Expired - Lifetime
-
1977
- 1977-11-17 CA CA291,154A patent/CA1084933A/en not_active Expired
- 1977-11-25 JP JP14079877A patent/JPS5371081A/ja active Pending
- 1977-12-01 FR FR7736242A patent/FR2372825A1/fr active Granted
- 1977-12-01 GB GB50132/77A patent/GB1573550A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1573550A (en) | 1980-08-28 |
| US4088765A (en) | 1978-05-09 |
| FR2372825A1 (fr) | 1978-06-30 |
| FR2372825B1 (Sortimente) | 1981-03-06 |
| JPS5371081A (en) | 1978-06-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |