DE2003825A1 - Verfahren zur Herstellung von 1-Acyl-2-amino-benzimidazol- und 1,3-Bisacyl-2-imino-benzimidazol-Derivaten - Google Patents
Verfahren zur Herstellung von 1-Acyl-2-amino-benzimidazol- und 1,3-Bisacyl-2-imino-benzimidazol-DerivatenInfo
- Publication number
- DE2003825A1 DE2003825A1 DE19702003825 DE2003825A DE2003825A1 DE 2003825 A1 DE2003825 A1 DE 2003825A1 DE 19702003825 DE19702003825 DE 19702003825 DE 2003825 A DE2003825 A DE 2003825A DE 2003825 A1 DE2003825 A1 DE 2003825A1
- Authority
- DE
- Germany
- Prior art keywords
- benzimidazole
- compound
- aminobenzimidazole
- compounds
- acyl
- 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
- 238000000034 method Methods 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 7
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical class C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
- 239000013078 crystal Substances 0.000 description 29
- 239000000047 product Substances 0.000 description 29
- 238000002844 melting Methods 0.000 description 24
- 230000008018 melting Effects 0.000 description 24
- 238000000354 decomposition reaction Methods 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 19
- -1 2-Amino-benzimidazole compound Chemical class 0.000 description 18
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 239000012458 free base Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- VQFAIAKCILWQPZ-UHFFFAOYSA-N bromoacetone Chemical compound CC(=O)CBr VQFAIAKCILWQPZ-UHFFFAOYSA-N 0.000 description 6
- KQILHTBMAQVQJQ-UHFFFAOYSA-N 1-(4-bromophenyl)-2-[3-[2-(4-bromophenyl)-2-oxoethyl]-2-iminobenzimidazol-1-yl]ethanone Chemical compound C1=CC(Br)=CC=C1C(=O)CN1C(=N)N(CC(=O)C=2C=CC(Br)=CC=2)C2=CC=CC=C21 KQILHTBMAQVQJQ-UHFFFAOYSA-N 0.000 description 4
- PJLGMFNGMNCBKO-UHFFFAOYSA-N 2-(2-aminobenzimidazol-1-yl)-1-phenylethanone Chemical compound NC1=NC2=CC=CC=C2N1CC(=O)C1=CC=CC=C1 PJLGMFNGMNCBKO-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- IXPZYJRRDFZWHJ-UHFFFAOYSA-N 4h-imidazo[1,2-a]benzimidazole Chemical class C1=CC=C2N3C=CN=C3NC2=C1 IXPZYJRRDFZWHJ-UHFFFAOYSA-N 0.000 description 3
- 150000001556 benzimidazoles Chemical class 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- MFYGTMWYVGYJFR-UHFFFAOYSA-N 2-(2-imino-3-phenacylbenzimidazol-1-yl)-1-phenylethanone Chemical compound C12=CC=CC=C2N(CC(=O)C=2C=CC=CC=2)C(=N)N1CC(=O)C1=CC=CC=C1 MFYGTMWYVGYJFR-UHFFFAOYSA-N 0.000 description 2
- JMOKZPTXGIMBNB-UHFFFAOYSA-N 2-(4-chlorophenyl)-3H-imidazo[1,2-a]benzimidazole Chemical compound ClC1=CC=C(C=C1)C=1N=C2NC3=C(N2C1)C=CC=C3 JMOKZPTXGIMBNB-UHFFFAOYSA-N 0.000 description 2
- FKJSFKCZZIXQIP-UHFFFAOYSA-N 2-bromo-1-(4-bromophenyl)ethanone Chemical compound BrCC(=O)C1=CC=C(Br)C=C1 FKJSFKCZZIXQIP-UHFFFAOYSA-N 0.000 description 2
- FLAYZKKEOIAALB-UHFFFAOYSA-N 2-bromo-1-(4-chlorophenyl)ethanone Chemical compound ClC1=CC=C(C(=O)CBr)C=C1 FLAYZKKEOIAALB-UHFFFAOYSA-N 0.000 description 2
- LOYLEFYQOSIFBB-UHFFFAOYSA-N 2-phenyl-3h-imidazo[1,2-a]benzimidazole Chemical compound N1C2=NC3=CC=CC=C3N2C=C1C1=CC=CC=C1 LOYLEFYQOSIFBB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- HCQNNQFCUAGJBD-UHFFFAOYSA-N 1-(4-bromophenyl)-2-chloroethanone Chemical compound ClCC(=O)C1=CC=C(Br)C=C1 HCQNNQFCUAGJBD-UHFFFAOYSA-N 0.000 description 1
- HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
- ZHAORBUAOPBIBP-UHFFFAOYSA-N 2,2-dibromo-1-phenylethanone Chemical compound BrC(Br)C(=O)C1=CC=CC=C1 ZHAORBUAOPBIBP-UHFFFAOYSA-N 0.000 description 1
- FSZSLVDWSBPVQZ-UHFFFAOYSA-N 2,3-diphenylimidazo[1,2-a]benzimidazole Chemical compound C=1C=CC=CC=1N1C2=NC3=CC=CC=C3N2C=C1C1=CC=CC=C1 FSZSLVDWSBPVQZ-UHFFFAOYSA-N 0.000 description 1
- IWUACMRENZNWBB-UHFFFAOYSA-N 2-(2-chlorophenyl)-1,3-oxazole Chemical compound ClC1=CC=CC=C1C1=NC=CO1 IWUACMRENZNWBB-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 101100460385 Caenorhabditis elegans nhx-2 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP597769A JPS4842875B1 (enrdf_load_stackoverflow) | 1969-01-29 | 1969-01-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2003825A1 true DE2003825A1 (de) | 1970-12-10 |
Family
ID=11625886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702003825 Pending DE2003825A1 (de) | 1969-01-29 | 1970-01-28 | Verfahren zur Herstellung von 1-Acyl-2-amino-benzimidazol- und 1,3-Bisacyl-2-imino-benzimidazol-Derivaten |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4842875B1 (enrdf_load_stackoverflow) |
| CA (1) | CA922723A (enrdf_load_stackoverflow) |
| CH (1) | CH529768A (enrdf_load_stackoverflow) |
| DE (1) | DE2003825A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2034505A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1295478A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2638553A1 (de) * | 1975-10-28 | 1977-05-12 | Lilly Co Eli | Thiazolinylbenzimidazole |
| WO2006097534A1 (en) * | 2005-03-17 | 2006-09-21 | Tibotec Pharmaceuticals Ltd | 1,3-dihydro-benzimidazol-2-ylidene amines as inhibitors of respiratory syncytial virus replication |
| US7244730B2 (en) | 2001-04-19 | 2007-07-17 | Eisai Co., Ltd | 2-iminopyrrolidine derivatives |
| US7375236B2 (en) | 2003-02-19 | 2008-05-20 | Eisai Co., Ltd. | Methods for producing cyclic benzamidine derivatives |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100297038A1 (en) * | 2008-01-17 | 2010-11-25 | Givaudan S.A. | Benzimidazole Derivatives And Their Use As Cooling Agents |
-
1969
- 1969-01-29 JP JP597769A patent/JPS4842875B1/ja active Pending
-
1970
- 1970-01-22 CA CA072845A patent/CA922723A/en not_active Expired
- 1970-01-28 FR FR7002999A patent/FR2034505A1/fr active Pending
- 1970-01-28 DE DE19702003825 patent/DE2003825A1/de active Pending
- 1970-01-28 GB GB1295478D patent/GB1295478A/en not_active Expired
- 1970-01-28 CH CH123770A patent/CH529768A/de not_active IP Right Cessation
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2638553A1 (de) * | 1975-10-28 | 1977-05-12 | Lilly Co Eli | Thiazolinylbenzimidazole |
| US7244730B2 (en) | 2001-04-19 | 2007-07-17 | Eisai Co., Ltd | 2-iminopyrrolidine derivatives |
| US7304083B2 (en) | 2001-04-19 | 2007-12-04 | Eisai R&D Management Co., Ltd. | 2-iminoimidazole derivatives (2) |
| US7476688B2 (en) | 2001-04-19 | 2009-01-13 | Eisai R&D Management Co., Ltd. | Cyclic amidine derivatives |
| US7375236B2 (en) | 2003-02-19 | 2008-05-20 | Eisai Co., Ltd. | Methods for producing cyclic benzamidine derivatives |
| WO2006097534A1 (en) * | 2005-03-17 | 2006-09-21 | Tibotec Pharmaceuticals Ltd | 1,3-dihydro-benzimidazol-2-ylidene amines as inhibitors of respiratory syncytial virus replication |
| RU2410382C2 (ru) * | 2005-03-17 | 2011-01-27 | Тиботек Фармасьютикалз Лтд | 1, 3-дигидробензимидазол-2-илиденовые амины в качестве ингибиторов репликации респираторного синцитиального вируса |
| US7956196B2 (en) | 2005-03-17 | 2011-06-07 | Tibotec Pharmaceuticals Ltd. | 1,3-dihydro-benzimidazol-2-ylidene amines as inhibitors of respiratory syncytial virus replication |
| CN101142208B (zh) * | 2005-03-17 | 2012-05-23 | 泰博特克药品有限公司 | 作为呼吸道合胞病毒复制抑制剂的1,3-二氢-苯并咪唑-2-亚基胺 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4842875B1 (enrdf_load_stackoverflow) | 1973-12-14 |
| FR2034505A1 (enrdf_load_stackoverflow) | 1970-12-11 |
| GB1295478A (enrdf_load_stackoverflow) | 1972-11-08 |
| CH529768A (de) | 1972-10-31 |
| CA922723A (en) | 1973-03-13 |
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