DE1595907A1 - Verfahren zur Herstellung von 5-Aryl-2-cycloalkylamino-4-oxazolinonen - Google Patents
Verfahren zur Herstellung von 5-Aryl-2-cycloalkylamino-4-oxazolinonenInfo
- Publication number
- DE1595907A1 DE1595907A1 DE19661595907 DE1595907A DE1595907A1 DE 1595907 A1 DE1595907 A1 DE 1595907A1 DE 19661595907 DE19661595907 DE 19661595907 DE 1595907 A DE1595907 A DE 1595907A DE 1595907 A1 DE1595907 A1 DE 1595907A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- aryl
- hydrogen
- alkyl
- 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.)
- Pending
Links
- 238000002360 preparation method Methods 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 4
- -1 cycloalkyl radical Chemical class 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000007945 N-acyl ureas Chemical class 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 8
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229960000632 dexamfetamine Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000002830 appetite depressant Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 208000000269 Hyperkinesis Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- UIXTUDLFNOIGRA-UHFFFAOYSA-N n-carbamoyl-2-chloroacetamide Chemical compound NC(=O)NC(=O)CCl UIXTUDLFNOIGRA-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- KCOPAESEGCGTKM-UHFFFAOYSA-N 1,3-oxazol-4-one Chemical compound O=C1COC=N1 KCOPAESEGCGTKM-UHFFFAOYSA-N 0.000 description 1
- MQBHQCAEEIVRMO-UHFFFAOYSA-N 1-cyclopropyl-1-methylurea Chemical compound NC(=O)N(C)C1CC1 MQBHQCAEEIVRMO-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940025084 amphetamine Drugs 0.000 description 1
- 230000002891 anorexigenic effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 230000005792 cardiovascular activity Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000002920 convulsive effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000037023 motor activity Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 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
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D263/48—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (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 |
|---|---|---|---|
| FR32611A FR4827M (forum.php) | 1965-09-24 | 1965-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1595907A1 true DE1595907A1 (de) | 1970-03-12 |
Family
ID=8589053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661595907 Pending DE1595907A1 (de) | 1965-09-24 | 1966-09-17 | Verfahren zur Herstellung von 5-Aryl-2-cycloalkylamino-4-oxazolinonen |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT262280B (forum.php) |
| BE (1) | BE687084A (forum.php) |
| CH (1) | CH466291A (forum.php) |
| DE (1) | DE1595907A1 (forum.php) |
| FR (1) | FR4827M (forum.php) |
| GB (1) | GB1109470A (forum.php) |
| LU (1) | LU52005A1 (forum.php) |
| NL (1) | NL6613484A (forum.php) |
-
1965
- 1965-09-24 FR FR32611A patent/FR4827M/fr not_active Expired
-
1966
- 1966-09-17 DE DE19661595907 patent/DE1595907A1/de active Pending
- 1966-09-19 BE BE687084D patent/BE687084A/xx unknown
- 1966-09-21 LU LU52005A patent/LU52005A1/xx unknown
- 1966-09-21 CH CH1359066A patent/CH466291A/fr unknown
- 1966-09-21 AT AT885566A patent/AT262280B/de active
- 1966-09-22 GB GB42399/66A patent/GB1109470A/en not_active Expired
- 1966-09-23 NL NL6613484A patent/NL6613484A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT262280B (de) | 1968-06-10 |
| NL6613484A (forum.php) | 1967-03-28 |
| LU52005A1 (forum.php) | 1966-11-21 |
| FR4827M (forum.php) | 1967-02-13 |
| GB1109470A (en) | 1968-04-10 |
| BE687084A (forum.php) | 1967-03-01 |
| CH466291A (fr) | 1968-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1179556B (de) | Verfahren zur herstellung von freiem oder acyliertem n-(4-diäthylaminobutyl)-salicyclsäureamid | |
| DE2160148C2 (de) | Arzneimittel und bestimmte Sulfoxide als solche | |
| CH380734A (de) | Verfahren zur Herstellung von neuen s-Triazinderivaten | |
| DE2829580C2 (de) | 2-Formylchinoxalin-1,4-dioxid-cyanoacetylhydrazon, Verfahren zu seiner Herstellung und Zusammensetzungen mit dieser Verbindung | |
| DE1518764B2 (de) | In der 7-SteUung substituierte S-Phenyl^-oxo^-dihydro-lH-M-benzodiazepin-3-carbonsäuresalze und -alkylester | |
| DE2129960C2 (de) | Thioureidoderivate enthaltende therapeutische Zusammensetzungen, Verfahren zu deren Herstellung sowie die Thioureidoderivate | |
| DE1159937B (de) | Verfahren zur Herstellung von Hydrindensulfonylharnstoffen | |
| DE1595907A1 (de) | Verfahren zur Herstellung von 5-Aryl-2-cycloalkylamino-4-oxazolinonen | |
| DE1813918C3 (de) | 2-Hydroxymethyl-3-carbonsäureamido--chinoxalin-M-di-N-oxide, ein Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende antibakterielle Mittel | |
| DE2557033C2 (de) | Acylderivate des 1,2-5,6-Dianhydro-dulcits, Verfahren zu deren Herstellung und diese Verbindungen enthaltende anticarcinogene Mittel | |
| DE1670937B2 (de) | 2-Halogenmethyl-3-carbonsäureamidochinoxalin-di-N-oxide-0.4) | |
| DE1232966B (de) | Verfahren zur Herstellung von (+)-Enantiomorphen von Indolverbindungen | |
| DE2309100C2 (de) | N-Acylierte Aminophenolätherderivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Formulierung zur Behandlung von Leberegelinfektionen bei Säugern | |
| DE850297C (de) | Verfahren zur Herstellung von Amidinsalzen | |
| DE1670936C3 (de) | 3-Carbonsäureamido-chinoxalin-di-Nojdde-0,4), ein Verfahren zu ihrer Herstellung und diese enthaltende antibakterielle Mittel | |
| AT338288B (de) | Verfahren zur herstellung neuer 7,7'-verbruckter bis-theophylline | |
| DE1177645B (de) | Verfahren zur Herstellung von kondensierten heterocyclischen Verbindungen | |
| DE2404924A1 (de) | Ergolinderivate | |
| AT237606B (de) | Verfahren zur Herstellung des neuen N-(4-Diäthylaminobutyl) -salicylsäureamids, seiner O-Acylderivate und der Salze dieser basischen Amide | |
| DE1545589C3 (de) | Tetracyclinderivate und Verfahren zu ihrer Herstellung | |
| DE1695156C (de) | Tetrahydroisochinohn derivate Ausscheidung aus 1244788 | |
| DE1071086B (forum.php) | ||
| DE1198368B (de) | Verfahren zur Herstellung von 5-(2, 6-Dimethoxyphenoxymethyl)-oxazolidon-(2) | |
| DE1620200B2 (de) | 7 Oxo desacetamido colchicin derivate, ein Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel Ausscheidung aus 1235322 | |
| DE1137438B (de) | Verfahren zur Herstellung von sedativ bzw. hypnotisch wirksamen Carbaminsaeureestern |