CS216901B2 - Způsob výroby nových anilidů kyselin aminoalkanových - Google Patents
Způsob výroby nových anilidů kyselin aminoalkanových Download PDFInfo
- Publication number
- CS216901B2 CS216901B2 CS9574A CS9574A CS216901B2 CS 216901 B2 CS216901 B2 CS 216901B2 CS 9574 A CS9574 A CS 9574A CS 9574 A CS9574 A CS 9574A CS 216901 B2 CS216901 B2 CS 216901B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hydrogen
- methyl
- ethyl
- group
- acid
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 21
- 150000003931 anilides Chemical class 0.000 title claims description 15
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000007513 acids Chemical class 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- -1 p-toluenesulfonyloxy group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000011630 iodine Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 65
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- 150000001875 compounds Chemical class 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
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- 239000000243 solution Substances 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 229910052799 carbon Inorganic materials 0.000 description 17
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- 241001465754 Metazoa Species 0.000 description 6
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- 238000004458 analytical method Methods 0.000 description 6
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- 239000003814 drug Substances 0.000 description 6
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 6
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- 239000007787 solid Substances 0.000 description 6
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- ILLHORFDXDLILE-UHFFFAOYSA-N 2-bromopropanoyl bromide Chemical compound CC(Br)C(Br)=O ILLHORFDXDLILE-UHFFFAOYSA-N 0.000 description 4
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
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- 239000003416 antiarrhythmic agent Substances 0.000 description 4
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- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
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- 239000000126 substance Substances 0.000 description 4
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- 208000003663 ventricular fibrillation Diseases 0.000 description 4
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- CUNLUFUNMBWECT-UHFFFAOYSA-N 3-amino-n-(2-chloro-6-methylphenyl)butanamide Chemical compound CC(N)CC(=O)NC1=C(C)C=CC=C1Cl CUNLUFUNMBWECT-UHFFFAOYSA-N 0.000 description 3
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- 239000000969 carrier Substances 0.000 description 1
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- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- REQCZEXYDRLIBE-UHFFFAOYSA-N procainamide Chemical compound CCN(CC)CCNC(=O)C1=CC=C(N)C=C1 REQCZEXYDRLIBE-UHFFFAOYSA-N 0.000 description 1
- 229960000244 procainamide Drugs 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS772982A CS216902B2 (cs) | 1973-01-08 | 1977-05-05 | Způsob výroby nových anilidů kyselin aminoalkanových |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32159073A | 1973-01-08 | 1973-01-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS216901B2 true CS216901B2 (cs) | 1982-12-31 |
Family
ID=23251210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS9574A CS216901B2 (cs) | 1973-01-08 | 1974-01-07 | Způsob výroby nových anilidů kyselin aminoalkanových |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS58198452A (enrdf_load_stackoverflow) |
| AT (1) | AT339285B (enrdf_load_stackoverflow) |
| BE (1) | BE809440A (enrdf_load_stackoverflow) |
| CS (1) | CS216901B2 (enrdf_load_stackoverflow) |
| ZA (1) | ZA74114B (enrdf_load_stackoverflow) |
-
1974
- 1974-01-01 ZA ZA740114A patent/ZA74114B/xx unknown
- 1974-01-07 CS CS9574A patent/CS216901B2/cs unknown
- 1974-01-07 AT AT7474A patent/AT339285B/de not_active IP Right Cessation
- 1974-01-07 BE BE139556A patent/BE809440A/xx not_active IP Right Cessation
-
1982
- 1982-11-24 JP JP20471782A patent/JPS58198452A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6154777B2 (enrdf_load_stackoverflow) | 1986-11-25 |
| BE809440A (fr) | 1974-07-08 |
| ZA74114B (en) | 1974-12-24 |
| ATA7474A (de) | 1977-02-15 |
| JPS58198452A (ja) | 1983-11-18 |
| AT339285B (de) | 1977-10-10 |
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