DE1470097A1 - Benzmidazole,Benzoxazole und Benzothiazole und Verfahren zu ihrer Herstellung - Google Patents
Benzmidazole,Benzoxazole und Benzothiazole und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1470097A1 DE1470097A1 DE19641470097 DE1470097A DE1470097A1 DE 1470097 A1 DE1470097 A1 DE 1470097A1 DE 19641470097 DE19641470097 DE 19641470097 DE 1470097 A DE1470097 A DE 1470097A DE 1470097 A1 DE1470097 A1 DE 1470097A1
- Authority
- DE
- Germany
- Prior art keywords
- solution
- water
- formula
- thiazolyl
- acid
- 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 31
- 230000008569 process Effects 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 9
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title description 23
- 150000000183 1,3-benzoxazoles Chemical class 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims description 54
- -1 carboalkoxy Chemical group 0.000 claims description 53
- 239000002253 acid Substances 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 229910052702 rhenium Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005059 halophenyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000005518 carboxamido group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000008186 active pharmaceutical agent Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 113
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 107
- 239000000243 solution Substances 0.000 description 94
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 74
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 70
- 239000000203 mixture Substances 0.000 description 55
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- 235000019441 ethanol Nutrition 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 239000000047 product Substances 0.000 description 38
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 238000003756 stirring Methods 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- 150000001556 benzimidazoles Chemical class 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000000126 substance Substances 0.000 description 20
- 239000007787 solid Substances 0.000 description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- 125000000335 thiazolyl group Chemical group 0.000 description 16
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- 241001465754 Metazoa Species 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 14
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 239000003208 petroleum Substances 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
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- 150000003254 radicals Chemical class 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- DWYHDSLIWMUSOO-UHFFFAOYSA-N 2-phenyl-1h-benzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2N1 DWYHDSLIWMUSOO-UHFFFAOYSA-N 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
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- 239000003674 animal food additive Substances 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 7
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- 238000004519 manufacturing process Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 6
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 6
- XBHOUXSGHYZCNH-UHFFFAOYSA-N 2-phenyl-1,3-benzothiazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2S1 XBHOUXSGHYZCNH-UHFFFAOYSA-N 0.000 description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
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- 150000001409 amidines Chemical class 0.000 description 5
- 150000003931 anilides Chemical class 0.000 description 5
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 5
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- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
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- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 4
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- 125000003118 aryl group Chemical group 0.000 description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
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- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- HJZYBDPHAHGHAZ-UHFFFAOYSA-N thiadiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSN=N1 HJZYBDPHAHGHAZ-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32168363A | 1963-11-06 | 1963-11-06 | |
| US33286163A | 1963-12-23 | 1963-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1470097A1 true DE1470097A1 (de) | 1969-06-04 |
Family
ID=26983075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641470097 Pending DE1470097A1 (de) | 1963-11-06 | 1964-10-23 | Benzmidazole,Benzoxazole und Benzothiazole und Verfahren zu ihrer Herstellung |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE655336A (enrdf_load_stackoverflow) |
| CH (1) | CH471131A (enrdf_load_stackoverflow) |
| DE (1) | DE1470097A1 (enrdf_load_stackoverflow) |
| DK (1) | DK124262B (enrdf_load_stackoverflow) |
| FR (2) | FR1568715A (enrdf_load_stackoverflow) |
| GB (1) | GB1088096A (enrdf_load_stackoverflow) |
| IL (1) | IL22272A (enrdf_load_stackoverflow) |
| NL (1) | NL6412728A (enrdf_load_stackoverflow) |
| NO (1) | NO118911B (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007118137A1 (en) * | 2006-04-07 | 2007-10-18 | Methylgene Inc. | Benzamide derivatives as inhibitors of histone deacetylase |
| US7595343B2 (en) | 2001-09-14 | 2009-09-29 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| US7838520B2 (en) | 2001-09-14 | 2010-11-23 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| US7868204B2 (en) | 2001-09-14 | 2011-01-11 | Methylgene Inc. | Inhibitors of histone deacetylase |
| US7868205B2 (en) | 2003-09-24 | 2011-01-11 | Methylgene Inc. | Inhibitors of histone deacetylase |
| US8088805B2 (en) | 2004-03-26 | 2012-01-03 | Methylgene Inc. | Inhibitors of histone deacetylase |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8524899B2 (en) * | 2003-03-04 | 2013-09-03 | California Institute Of Technology | Alternative heterocycles for DNA recognition |
| PT2895465T (pt) * | 2012-04-20 | 2019-01-16 | Boehringer Ingelheim Animal Health Usa Inc | Composições parasiticidas compreendendo derivados de benzimidazoles, os seus métodos e as suas utilizações |
-
1964
- 1964-10-18 IL IL2227264A patent/IL22272A/xx unknown
- 1964-10-23 DE DE19641470097 patent/DE1470097A1/de active Pending
- 1964-11-02 NL NL6412728A patent/NL6412728A/xx unknown
- 1964-11-04 GB GB44965/64A patent/GB1088096A/en not_active Expired
- 1964-11-05 NO NO15543764A patent/NO118911B/no unknown
- 1964-11-05 FR FR994013A patent/FR1568715A/fr not_active Expired
- 1964-11-05 BE BE655336D patent/BE655336A/xx unknown
- 1964-11-06 CH CH1437864A patent/CH471131A/de not_active IP Right Cessation
- 1964-11-06 DK DK549264A patent/DK124262B/da unknown
-
1965
- 1965-02-04 FR FR4430A patent/FR4039M/fr not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7595343B2 (en) | 2001-09-14 | 2009-09-29 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| US7838520B2 (en) | 2001-09-14 | 2010-11-23 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| US7868204B2 (en) | 2001-09-14 | 2011-01-11 | Methylgene Inc. | Inhibitors of histone deacetylase |
| US7868205B2 (en) | 2003-09-24 | 2011-01-11 | Methylgene Inc. | Inhibitors of histone deacetylase |
| US8088805B2 (en) | 2004-03-26 | 2012-01-03 | Methylgene Inc. | Inhibitors of histone deacetylase |
| WO2007118137A1 (en) * | 2006-04-07 | 2007-10-18 | Methylgene Inc. | Benzamide derivatives as inhibitors of histone deacetylase |
| US8598168B2 (en) | 2006-04-07 | 2013-12-03 | Methylgene Inc. | Inhibitors of histone deacetylase |
Also Published As
| Publication number | Publication date |
|---|---|
| NO118911B (enrdf_load_stackoverflow) | 1970-03-02 |
| BE655336A (enrdf_load_stackoverflow) | 1965-05-05 |
| FR4039M (enrdf_load_stackoverflow) | 1966-03-28 |
| DK124262B (da) | 1972-10-02 |
| NL6412728A (enrdf_load_stackoverflow) | 1965-05-07 |
| GB1088096A (en) | 1967-10-18 |
| FR1568715A (enrdf_load_stackoverflow) | 1969-05-30 |
| IL22272A (en) | 1969-02-27 |
| CH471131A (de) | 1969-04-15 |
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