DE2429561C3 - Verfahren zur Herstellung von in 5-StelIung substituierten 2-Aminophenolen und bestimmte dieser Aminophenole als solche - Google Patents
Verfahren zur Herstellung von in 5-StelIung substituierten 2-Aminophenolen und bestimmte dieser Aminophenole als solcheInfo
- Publication number
- DE2429561C3 DE2429561C3 DE19742429561 DE2429561A DE2429561C3 DE 2429561 C3 DE2429561 C3 DE 2429561C3 DE 19742429561 DE19742429561 DE 19742429561 DE 2429561 A DE2429561 A DE 2429561A DE 2429561 C3 DE2429561 C3 DE 2429561C3
- Authority
- DE
- Germany
- Prior art keywords
- aminophenols
- alcohol
- hydrogen atom
- substituted
- preparation
- 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
- 238000000034 method Methods 0.000 title claims description 13
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical group NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
- -1 alkyl radical Chemical class 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229930182555 Penicillin Natural products 0.000 description 4
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 229940049954 penicillin Drugs 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 3
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 2
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 2
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 2
- 229960001138 acetylsalicylic acid Drugs 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 229940095731 candida albicans Drugs 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- KCOPAESEGCGTKM-UHFFFAOYSA-N 1,3-oxazol-4-one Chemical compound O=C1COC=N1 KCOPAESEGCGTKM-UHFFFAOYSA-N 0.000 description 1
- QQZFVONVJPXCSQ-UHFFFAOYSA-N 1-(4-amino-2-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC=C(N)C=C1O QQZFVONVJPXCSQ-UHFFFAOYSA-N 0.000 description 1
- UPULOMQHYQDNNT-UHFFFAOYSA-N 5h-1,3-oxazol-2-one Chemical group O=C1OCC=N1 UPULOMQHYQDNNT-UHFFFAOYSA-N 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical class CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 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
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7323282A FR2244465B1 (enrdf_load_stackoverflow) | 1973-06-26 | 1973-06-26 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2429561A1 DE2429561A1 (de) | 1975-01-16 |
| DE2429561B2 DE2429561B2 (de) | 1977-12-22 |
| DE2429561C3 true DE2429561C3 (de) | 1978-08-24 |
Family
ID=9121570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742429561 Expired DE2429561C3 (de) | 1973-06-26 | 1974-06-20 | Verfahren zur Herstellung von in 5-StelIung substituierten 2-Aminophenolen und bestimmte dieser Aminophenole als solche |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5069032A (enrdf_load_stackoverflow) |
| DE (1) | DE2429561C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2244465B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1425430A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3168532D1 (en) * | 1980-11-15 | 1985-03-07 | Fisons Plc | Process for the production of 3-amino-4,6-diacetyl phenol or a derivative thereof |
| US5221742A (en) * | 1990-12-21 | 1993-06-22 | Ortho Pharmaceutical Corporation | Process for the preparation of 6-(3,4-dihydro-3-oxo-1,4(2h)-benzoxazin-7-yl)-2,3,4,5-tetrahydropyridazin-3-ones |
-
1973
- 1973-06-26 FR FR7323282A patent/FR2244465B1/fr not_active Expired
-
1974
- 1974-06-20 DE DE19742429561 patent/DE2429561C3/de not_active Expired
- 1974-06-24 GB GB2795374A patent/GB1425430A/en not_active Expired
- 1974-06-26 JP JP7374474A patent/JPS5069032A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2244465B1 (enrdf_load_stackoverflow) | 1977-07-01 |
| DE2429561A1 (de) | 1975-01-16 |
| DE2429561B2 (de) | 1977-12-22 |
| FR2244465A1 (enrdf_load_stackoverflow) | 1975-04-18 |
| JPS5069032A (enrdf_load_stackoverflow) | 1975-06-09 |
| GB1425430A (en) | 1976-02-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1906527B2 (de) | Thioninderivate, Verfahren zu deren Herstellung und pharmazeutische Präparate, welche diese enthalten | |
| DE2842263A1 (de) | Herstellung chromogener pyridinverbindungen | |
| DE2429561C3 (de) | Verfahren zur Herstellung von in 5-StelIung substituierten 2-Aminophenolen und bestimmte dieser Aminophenole als solche | |
| DE2818351A1 (de) | Benzoesaeurederivate, verfahren zu ihrer herstellung und ihre therapeutische verwendung | |
| DE1620141A1 (de) | Verfahren zur Herstellung eines Aminomethylindols | |
| DE2746550C2 (enrdf_load_stackoverflow) | ||
| DE1939111C3 (de) | Derivate der N- eckige Klammer auf 3-Trifluormethylphenyl eckige Klammer zu -anthranilsäure, Verfahren zu ihrer Herstellung und pharmakologisch wirksame Zubereitungen derselben | |
| DE3104883C2 (de) | Benzylidenderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DE1795402B2 (de) | 4-(3',4',5'-Trimethoxycinnamoy I)l-(äthoxycarbonylmethyl)-piperazin | |
| DE2046904A1 (de) | Indohzinessigsauren und Verfahren zu ihrer Herstellung | |
| DE2244265A1 (de) | Neue imidazolderivate, ihre herstellung und die medizinischen zusammensetzungen, die sie enthalten | |
| DE2141640A1 (de) | l,2,3,4-Tetrahydrocarbazol-2-carbonsäure-Derivate | |
| DE2024049B2 (de) | Alpha-(3,4-dihydroxyphenyl)-alpha(2-piperidinyl)-methanol | |
| DE1815804A1 (de) | Verfahren zur Herstellung einer neuen substituierten Anthranilsaeure | |
| DE79385C (de) | Verfahren zur Darstellung von p-Amidoj'-phenylchinolin und p-Amido-7--phenylchh>aldin | |
| CH478762A (de) | Verfahren zur Herstellung von neuen substituierten Zimtsäuren | |
| DE2416024A1 (de) | Neue organische verbindungen und verfahren zu deren herstellung | |
| DE1670936C3 (de) | 3-Carbonsäureamido-chinoxalin-di-Nojdde-0,4), ein Verfahren zu ihrer Herstellung und diese enthaltende antibakterielle Mittel | |
| DE2252323B2 (de) | 3,6-Dialkyl-23-dihydro-2,9-dioxo-6H,9H-thiazolo [5,4-fJ chinolin-e-carbonyl- Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Bakterizide | |
| DE344501C (enrdf_load_stackoverflow) | ||
| DE1595875C (de) | Phenothiazine und Verfahren zu deren Herstellung | |
| DE1795153A1 (de) | Neue N-substituierte Piperidinspiroverbindungen,ihre Verwendung und Herstellung | |
| DE1770775A1 (de) | Neue Dibenzazepinderivate und Verfahren zu ihrer Herstellung | |
| DE212205C (enrdf_load_stackoverflow) | ||
| DE1901167C3 (de) | Substituierte Indole, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |