DE2263519A1 - 4h-1,3-benzoxazin-2-on-3-acethydroxamsaeurederivate - Google Patents
4h-1,3-benzoxazin-2-on-3-acethydroxamsaeurederivateInfo
- Publication number
- DE2263519A1 DE2263519A1 DE2263519A DE2263519A DE2263519A1 DE 2263519 A1 DE2263519 A1 DE 2263519A1 DE 2263519 A DE2263519 A DE 2263519A DE 2263519 A DE2263519 A DE 2263519A DE 2263519 A1 DE2263519 A1 DE 2263519A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- benzoxazin
- acethydroxamic
- acethydroxamic acid
- acid derivatives
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 4
- -1 β-hydroxyethyl Chemical group 0.000 claims description 4
- 239000000935 antidepressant agent Substances 0.000 claims description 3
- 229940005513 antidepressants Drugs 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000001430 anti-depressive effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 9
- 229960003147 reserpine Drugs 0.000 description 8
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 7
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 7
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 7
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 7
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 7
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 5
- 229960004801 imipramine Drugs 0.000 description 5
- ALMZBCNUAPKJDP-UHFFFAOYSA-N 4h-1,3-benzoxazine Chemical compound C1=CC=C2CN=COC2=C1 ALMZBCNUAPKJDP-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010015995 Eyelid ptosis Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 201000003004 ptosis Diseases 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- 206010049816 Muscle tightness Diseases 0.000 description 1
- RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 description 1
- 229960001171 acetohydroxamic acid Drugs 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- HDCAZTXEZQWTIJ-UHFFFAOYSA-N n,n',n'-triethylethane-1,2-diamine Chemical compound CCNCCN(CC)CC HDCAZTXEZQWTIJ-UHFFFAOYSA-N 0.000 description 1
- 230000003040 nociceptive effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000009154 spontaneous behavior Effects 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3299271 | 1971-12-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2263519A1 true DE2263519A1 (de) | 1973-07-12 |
Family
ID=11236232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2263519A Pending DE2263519A1 (de) | 1971-12-28 | 1972-12-27 | 4h-1,3-benzoxazin-2-on-3-acethydroxamsaeurederivate |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3948890A (enExample) |
| JP (1) | JPS4875581A (enExample) |
| CH (1) | CH577986A5 (enExample) |
| DE (1) | DE2263519A1 (enExample) |
| FR (1) | FR2166010B1 (enExample) |
| GB (1) | GB1359966A (enExample) |
| HU (1) | HU164418B (enExample) |
| SU (1) | SU455543A3 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0507695D0 (en) * | 2005-04-15 | 2005-05-25 | Novartis Ag | Organic compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3658803A (en) * | 1967-08-01 | 1972-04-25 | Farmaceutici Italia | 1 3-benzoxazine derivatives |
-
1972
- 1972-12-19 GB GB5863772A patent/GB1359966A/en not_active Expired
- 1972-12-26 FR FR7246146A patent/FR2166010B1/fr not_active Expired
- 1972-12-26 JP JP47129658A patent/JPS4875581A/ja active Pending
- 1972-12-27 SU SU1864311A patent/SU455543A3/ru active
- 1972-12-27 CH CH1889972A patent/CH577986A5/xx not_active IP Right Cessation
- 1972-12-27 HU HUFA936A patent/HU164418B/hu unknown
- 1972-12-27 DE DE2263519A patent/DE2263519A1/de active Pending
- 1972-12-29 US US05/319,724 patent/US3948890A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4875581A (enExample) | 1973-10-11 |
| CH577986A5 (enExample) | 1976-07-30 |
| HU164418B (enExample) | 1974-02-28 |
| SU455543A3 (ru) | 1974-12-30 |
| US3948890A (en) | 1976-04-06 |
| GB1359966A (en) | 1974-07-17 |
| FR2166010A1 (enExample) | 1973-08-10 |
| FR2166010B1 (enExample) | 1976-07-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1770153B2 (de) | Heterocyclische Aminoketone, deren pharmakologisch verträgliche Säureadditionssalze und Verfahren zu ihrer Herstellung | |
| DE3530046A1 (de) | Aethylendiaminmonoamid-derivate | |
| DE2257715A1 (de) | 6-methylen-6-desoxydihydromorphinund codeinderivate | |
| DE1445186B2 (de) | 3,3'-Di-2-imidazolin-2-yl-carbanilid | |
| DE2221758C2 (de) | Yohimbinderivat, Verfahren zu dessen Herstellung und dieses enthaltende Arzneimittel | |
| DE1645906C3 (de) | 4 Phenyl 1 piperidin carboxamide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen | |
| DE2263519A1 (de) | 4h-1,3-benzoxazin-2-on-3-acethydroxamsaeurederivate | |
| DE2542791C2 (de) | N,N'-Disubstituierte Naphthylacetamidine | |
| DE1965343A1 (de) | Arzneimittel,insbesondere zur Herabsetzung der Schleimviskositaet und Anwendung als hustenstillendes Mittel,und Verfahren zu seiner Herstellung | |
| DE1289849B (de) | 3-(Dibenzo[a, d]-1, 4-cycloheptadien-5-yloxy)-nortropan und Verfahren zu dessen Herstellung | |
| DE2945636A1 (de) | Stabile loesungen von hydrierten ergotalkaloiden bzw. ihren salzen und heparin bzw. seinen salzen sowie verfahren zu deren herstellung | |
| DE2560602C2 (de) | Sauerstoffhaltige Diarylamidine | |
| DE2132113C3 (de) | Derivate und Analoge des Naphthoxybutyramidins und deren Additionssalze mit Säuren, deren Herstellung und diese enthaltende pharmazeutische Mittel | |
| DE2029510B2 (de) | Dibenzofuranderivate und deren pharmazeutisch verträgliche Säureadditionssalze sowie Verfahren zu deren Herstellung und Arzneimittel mit einem Gehalt dieser Verbindungen | |
| DE1795003C3 (de) | 4H-13-Benzoxazin-2-on-3-acetohydroxamsäure, Verfahren zu deren Herstellung und Arzneimittel | |
| DE1767212B1 (de) | Verfahren zur Herstellung injizierbarer Arzneimittel | |
| DE963514C (de) | Verfahren zur Herstellung schwerloeslicher kristallisierter Streptomycin- und Dihydrostreptomycinsalze | |
| DE2156056C3 (de) | 3-tf',2'-Diphenyläthyl)-5-(2piperidino-äthyl)-1,2,4-oxadiazol-4-hydroxybenzoyl-benzoat-(2), dessen Herstellung und diese Verbindungen enthaltende Präparate | |
| CH556323A (de) | Verfahren zur herstellung von neuen naphthylalkylaminen. | |
| DE1235310B (de) | Verfahren zur Herstellung von Nopinsaeurederivaten | |
| AT213395B (de) | Verfahren zur Herstellung des neuen β-Hydroxybuttersäure-cyclohexylamids | |
| AT265530B (de) | Verfahren zur Herstellung von neuen Isochinolinderivaten | |
| DE2235745C3 (de) | 2-Amino-2',6'-propionoxylidid. Verfahren zu dessen Herstellung und dieses enthaltende Arzneimittel | |
| AT221495B (de) | Verfahren zur Herstellung von neuen Dibenzocycloheptanderivaten und deren Salzen bzw. quaternären Ammoniumverbindungen | |
| AT275497B (de) | Verfahren zur Herstellung von neuen 1-Dialkylaminoadamantanen und ihren Salzen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |