DE2023711A1 - N-acroyl-2-aminobenzhydrols antifungals - Google Patents
N-acroyl-2-aminobenzhydrols antifungalsInfo
- Publication number
- DE2023711A1 DE2023711A1 DE19702023711 DE2023711A DE2023711A1 DE 2023711 A1 DE2023711 A1 DE 2023711A1 DE 19702023711 DE19702023711 DE 19702023711 DE 2023711 A DE2023711 A DE 2023711A DE 2023711 A1 DE2023711 A1 DE 2023711A1
- Authority
- DE
- Germany
- Prior art keywords
- acroyl
- aminobenzhydrol
- methyl
- lower alkyl
- 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.)
- Granted
Links
- ZQZPHDCKGGDHIC-UHFFFAOYSA-N N-[2-[hydroxy(phenyl)methyl]phenyl]prop-2-enamide Chemical class C(C=C)(=O)NC1=C(C(C2=CC=CC=C2)O)C=CC=C1 ZQZPHDCKGGDHIC-UHFFFAOYSA-N 0.000 title claims 2
- 229940121375 antifungal agent Drugs 0.000 title 1
- INPGAIYFEYTJNI-UHFFFAOYSA-N N-[hydroxy(diphenyl)methyl]prop-2-enamide Chemical class C(C=C)(=O)NC(C1=CC=CC=C1)(C1=CC=CC=C1)O INPGAIYFEYTJNI-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- ZGAFLPZPTLIDQO-UHFFFAOYSA-N n-[4-chloro-2-[hydroxy(phenyl)methyl]phenyl]prop-2-enamide Chemical compound C=1C(Cl)=CC=C(NC(=O)C=C)C=1C(O)C1=CC=CC=C1 ZGAFLPZPTLIDQO-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000012433 hydrogen halide Substances 0.000 claims description 5
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 150000007514 bases Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
- NAWYZLGDGZTAPN-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanol Chemical class NC1=CC=CC=C1C(O)C1=CC=CC=C1 NAWYZLGDGZTAPN-UHFFFAOYSA-N 0.000 claims 1
- AOWOOJMOOWRPDC-UHFFFAOYSA-N C(=O)(C=C)N(C1=C(C(C2=CC=CC=C2)O)C=C(C=C1)Cl)C Chemical compound C(=O)(C=C)N(C1=C(C(C2=CC=CC=C2)O)C=C(C=C1)Cl)C AOWOOJMOOWRPDC-UHFFFAOYSA-N 0.000 claims 1
- CVWPEGYDDRTHMR-UHFFFAOYSA-N N-[2-[hydroxy(phenyl)methyl]-4-methylphenyl]prop-2-enamide Chemical compound C(C=C)(=O)NC1=C(C(C2=CC=CC=C2)O)C=C(C=C1)C CVWPEGYDDRTHMR-UHFFFAOYSA-N 0.000 claims 1
- VKRQWGUWYQDHAX-UHFFFAOYSA-N N-[2-[hydroxy(phenyl)methyl]-4-nitrophenyl]prop-2-enamide Chemical compound C(C=C)(=O)NC1=C(C(C2=CC=CC=C2)O)C=C(C=C1)[N+](=O)[O-] VKRQWGUWYQDHAX-UHFFFAOYSA-N 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 abstract description 4
- UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 abstract description 4
- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 abstract description 4
- 229960002867 griseofulvin Drugs 0.000 abstract description 4
- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 abstract description 4
- -1 hydroxy, methoxy Chemical group 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 230000000843 anti-fungal effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PKKSAVQQCBTBNZ-UHFFFAOYSA-N amino(diphenyl)methanol Chemical class C=1C=CC=CC=1C(O)(N)C1=CC=CC=C1 PKKSAVQQCBTBNZ-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229960000988 nystatin Drugs 0.000 description 2
- VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- PAHDPXOLONPKTP-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanol Chemical compound NC1=CC=C(Cl)C=C1C(O)C1=CC=CC=C1 PAHDPXOLONPKTP-UHFFFAOYSA-N 0.000 description 1
- ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 description 1
- XOOUJZYAMWOBCR-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone diphenylmethanol Chemical compound C(C1=CC=CC=C1)(C1=CC=CC=C1)O.NC1=C(C(=O)C2=CC=CC=C2)C=CC=C1 XOOUJZYAMWOBCR-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702023711 DE2023711A1 (en) | 1970-05-14 | 1970-05-14 | N-acroyl-2-aminobenzhydrols antifungals |
| AU28531/71A AU2853171A (en) | 1970-05-14 | 1971-05-05 | Substituted amino-benzhydrols and their preparation |
| BE766969A BE766969A (fr) | 1970-05-14 | 1971-05-10 | Aminobenzhydrols substitues et procede pour leur preparation |
| FR7117117A FR2100652A1 (en) | 1970-05-14 | 1971-05-12 | N-acroyl-2-aminobenzhydrols antifungals |
| NL7106613A NL7106613A (enrdf_load_stackoverflow) | 1970-05-14 | 1971-05-13 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702023711 DE2023711A1 (en) | 1970-05-14 | 1970-05-14 | N-acroyl-2-aminobenzhydrols antifungals |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2023711A1 true DE2023711A1 (en) | 1971-12-02 |
| DE2023711C DE2023711C (enrdf_load_stackoverflow) | 1973-02-22 |
Family
ID=5771159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702023711 Granted DE2023711A1 (en) | 1970-05-14 | 1970-05-14 | N-acroyl-2-aminobenzhydrols antifungals |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2023711A1 (enrdf_load_stackoverflow) |
-
1970
- 1970-05-14 DE DE19702023711 patent/DE2023711A1/de active Granted
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |