DE2517270A1 - Derivate des 2h,3h-benzimidazo-(1, 2-b)-oxazols - Google Patents
Derivate des 2h,3h-benzimidazo-(1, 2-b)-oxazolsInfo
- Publication number
- DE2517270A1 DE2517270A1 DE19752517270 DE2517270A DE2517270A1 DE 2517270 A1 DE2517270 A1 DE 2517270A1 DE 19752517270 DE19752517270 DE 19752517270 DE 2517270 A DE2517270 A DE 2517270A DE 2517270 A1 DE2517270 A1 DE 2517270A1
- Authority
- DE
- Germany
- Prior art keywords
- benzimidazo
- oxazole
- general formula
- compounds
- represent
- 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
- AYPSHJCKSDNETA-UHFFFAOYSA-N 2-chloro-1h-benzimidazole Chemical class C1=CC=C2NC(Cl)=NC2=C1 AYPSHJCKSDNETA-UHFFFAOYSA-N 0.000 title claims description 9
- 102000006635 beta-lactamase Human genes 0.000 title claims description 6
- ACNQNJXQUDTPHA-UHFFFAOYSA-N 2h-imidazo[4,5-e][1,3]benzoxazole Chemical compound C1=C2N=CN=C2C2=NCOC2=C1 ACNQNJXQUDTPHA-UHFFFAOYSA-N 0.000 title 1
- 108090000204 Dipeptidase 1 Proteins 0.000 title 1
- 239000004593 Epoxy Substances 0.000 title 1
- 150000003944 halohydrins Chemical class 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- -1 pyrrolidino, piperidino Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 18
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 108020004256 Beta-lactamase Proteins 0.000 claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 239000000543 intermediate Substances 0.000 claims description 3
- TUUXUMGGHRZSML-UHFFFAOYSA-N 2-ethyl-1,2-dihydro-[1,3]oxazolo[3,2-a]benzimidazole Chemical compound C1=CC=C2N3CC(CC)OC3=NC2=C1 TUUXUMGGHRZSML-UHFFFAOYSA-N 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229930182555 Penicillin Natural products 0.000 abstract description 5
- 150000002960 penicillins Chemical class 0.000 abstract description 5
- 229930186147 Cephalosporin Natural products 0.000 abstract description 4
- 229940124587 cephalosporin Drugs 0.000 abstract description 4
- 150000001780 cephalosporins Chemical class 0.000 abstract description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 239000003781 beta lactamase inhibitor Substances 0.000 abstract 1
- 229940126813 beta-lactamase inhibitor Drugs 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 150000002916 oxazoles Chemical class 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000203 mixture Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 241000786363 Rhampholeon spectrum Species 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- MCDPBZJERFZKCU-UHFFFAOYSA-N 1-(2-chlorobenzimidazol-1-yl)butan-2-ol Chemical compound C1=CC=C2N(CC(O)CC)C(Cl)=NC2=C1 MCDPBZJERFZKCU-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 241000219470 Mirabilis Species 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 2
- 229960000723 ampicillin Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical group O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 description 2
- XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 description 2
- 229960000603 cefalotin Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- XHXRGDWCSOGFTK-UHFFFAOYSA-N 2-(2-chlorobenzimidazol-1-yl)ethanol Chemical compound C1=CC=C2N(CCO)C(Cl)=NC2=C1 XHXRGDWCSOGFTK-UHFFFAOYSA-N 0.000 description 1
- OCVXSFKKWXMYPF-UHFFFAOYSA-N 2-chloroimidazole Chemical compound ClC1=NC=CN1 OCVXSFKKWXMYPF-UHFFFAOYSA-N 0.000 description 1
- NKUSMWHUSCQNTN-UHFFFAOYSA-N 5,7-dioxa-2-azabicyclo[4.1.0]heptane Chemical compound N1CCOC2OC21 NKUSMWHUSCQNTN-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- VYXHEFOZRVPJRK-UHFFFAOYSA-N ethyl 3-methyloxirane-2-carboxylate Chemical compound CCOC(=O)C1OC1C VYXHEFOZRVPJRK-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752517270 DE2517270A1 (de) | 1975-04-18 | 1975-04-18 | Derivate des 2h,3h-benzimidazo-(1, 2-b)-oxazols |
| LU72533A LU72533A1 (enExample) | 1975-04-18 | 1975-05-20 | |
| BE161871A BE835570Q (fr) | 1975-04-18 | 1975-11-13 | Procede de preparation de derives de 2h, 3h-benzimidazo(1, 2-b)-oxazole |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752517270 DE2517270A1 (de) | 1975-04-18 | 1975-04-18 | Derivate des 2h,3h-benzimidazo-(1, 2-b)-oxazols |
| LU72533A LU72533A1 (enExample) | 1975-04-18 | 1975-05-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2517270A1 true DE2517270A1 (de) | 1976-10-21 |
Family
ID=25768789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752517270 Pending DE2517270A1 (de) | 1975-04-18 | 1975-04-18 | Derivate des 2h,3h-benzimidazo-(1, 2-b)-oxazols |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE835570Q (enExample) |
| DE (1) | DE2517270A1 (enExample) |
| LU (1) | LU72533A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2370747A1 (fr) * | 1976-10-13 | 1978-06-09 | Italchemi Spa | Nouveaux derives du 2h,3h-benzimidazo (1,2-b) oxazole ainsi que leur application en therapeutique |
-
1975
- 1975-04-18 DE DE19752517270 patent/DE2517270A1/de active Pending
- 1975-05-20 LU LU72533A patent/LU72533A1/xx unknown
- 1975-11-13 BE BE161871A patent/BE835570Q/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| LU72533A1 (enExample) | 1975-10-08 |
| BE835570Q (fr) | 1976-03-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |