BE583826A - - Google Patents
Info
- Publication number
- BE583826A BE583826A BE583826DA BE583826A BE 583826 A BE583826 A BE 583826A BE 583826D A BE583826D A BE 583826DA BE 583826 A BE583826 A BE 583826A
- Authority
- BE
- Belgium
- Prior art keywords
- sep
- methyl
- dicarbamate
- ethyl
- butyl
- Prior art date
Links
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 claims description 394
- 150000001875 compounds Chemical class 0.000 claims description 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
- -1 2-methyl-2-ethyl Chemical group 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 35
- 238000002360 preparation method Methods 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 21
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 20
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- KXDHJXZQYSOELW-UHFFFAOYSA-M carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 13
- QOOXGUCQYVVEFD-UHFFFAOYSA-N 2-butyl-2-methylpropane-1,3-diol Chemical compound CCCCC(C)(CO)CO QOOXGUCQYVVEFD-UHFFFAOYSA-N 0.000 claims description 10
- 206010021118 Hypotonia Diseases 0.000 claims description 10
- 230000036640 muscle relaxation Effects 0.000 claims description 10
- 238000007112 amidation reaction Methods 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 8
- 150000002009 diols Chemical class 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 7
- XLJMAIOERFSOGZ-UHFFFAOYSA-N 420-05-3 Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 7
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims description 6
- 230000000875 corresponding Effects 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-Propanediol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N [N-]=C=O Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 5
- VNAWKNVDKFZFSU-UHFFFAOYSA-N 2-ethyl-2-methylpropane-1,3-diol Chemical compound CCC(C)(CO)CO VNAWKNVDKFZFSU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- NCTPQXCGJHWDQF-UHFFFAOYSA-N 2-ethyl-2-propan-2-ylpropane-1,3-diol Chemical compound CCC(CO)(CO)C(C)C NCTPQXCGJHWDQF-UHFFFAOYSA-N 0.000 claims description 2
- QPIAAQDLOJNQMP-UHFFFAOYSA-N 2-ethyl-2-propylpropane-1,3-diol Chemical compound CCCC(CC)(CO)CO QPIAAQDLOJNQMP-UHFFFAOYSA-N 0.000 claims description 2
- NJHQOQAEEYIWOB-UHFFFAOYSA-N 2-methyl-2-propan-2-ylpropane-1,3-diol Chemical compound CC(C)C(C)(CO)CO NJHQOQAEEYIWOB-UHFFFAOYSA-N 0.000 claims description 2
- 210000003205 Muscles Anatomy 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 2
- 230000002040 relaxant effect Effects 0.000 claims description 2
- HTXVEEVTGGCUNC-UHFFFAOYSA-N heptane-1,3-diol Chemical compound CCCCC(O)CCO HTXVEEVTGGCUNC-UHFFFAOYSA-N 0.000 claims 6
- XRVCFZPJAHWYTB-UHFFFAOYSA-N 2,2-diethylpropane-1,3-diol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 claims 3
- DSKYSDCYIODJPC-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol Chemical compound CCCCC(CC)(CO)CO DSKYSDCYIODJPC-UHFFFAOYSA-N 0.000 claims 2
- SIMYRXPCIUXDGR-UHFFFAOYSA-N 2-butylpropane-1,3-diol Chemical compound CCCCC(CO)CO SIMYRXPCIUXDGR-UHFFFAOYSA-N 0.000 claims 1
- HYFFNAVAMIJUIP-UHFFFAOYSA-N 2-ethylpropane-1,3-diol Chemical compound CCC(CO)CO HYFFNAVAMIJUIP-UHFFFAOYSA-N 0.000 claims 1
- 230000003000 nontoxic Effects 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 238000004821 distillation Methods 0.000 description 10
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical group NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 9
- 229960004815 Meprobamate Drugs 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 7
- 231100000636 lethal dose Toxicity 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000012264 purified product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
- JWDYCNIAQWPBHD-UHFFFAOYSA-N Mephenesin Chemical compound CC1=CC=CC=C1OCC(O)CO JWDYCNIAQWPBHD-UHFFFAOYSA-N 0.000 description 4
- 206010028334 Muscle spasms Diseases 0.000 description 4
- 208000005392 Spasm Diseases 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000011343 solid material Substances 0.000 description 4
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M Sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 3
- YFHICDDUDORKJB-UHFFFAOYSA-N Trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000012024 dehydrating agents Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drugs Drugs 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 229960003861 mephenesin Drugs 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 229940054025 Carbamate anxiolytics Drugs 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N Isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- SRTHRWZAMDZJOS-UHFFFAOYSA-N Lithium hydride Chemical compound [H-].[Li+] SRTHRWZAMDZJOS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000005712 crystallization Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000000199 molecular distillation Methods 0.000 description 2
- 239000003158 myorelaxant agent Substances 0.000 description 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 2
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- 239000001184 potassium carbonate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- JVZZUPJFERSVRN-UHFFFAOYSA-N 2-methyl-2-propylpropane-1,3-diol Chemical compound CCCC(C)(CO)CO JVZZUPJFERSVRN-UHFFFAOYSA-N 0.000 description 1
- CHWUDIOGEZKMMC-UHFFFAOYSA-N 5-ethyl-5-methyl-1,3-dioxan-2-one Chemical compound CCC1(C)COC(=O)OC1 CHWUDIOGEZKMMC-UHFFFAOYSA-N 0.000 description 1
- XJKJWTWGDGIQRH-BFIDDRIFSA-N Alginic acid Chemical compound O1[C@@H](C(O)=O)[C@@H](OC)[C@H](O)[C@H](O)[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](C)[C@@H](O)[C@H]1O XJKJWTWGDGIQRH-BFIDDRIFSA-N 0.000 description 1
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N Ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 210000003169 Central Nervous System Anatomy 0.000 description 1
- 206010008129 Cerebral palsy Diseases 0.000 description 1
- 210000001072 Colon Anatomy 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- UFEJKYYYVXYMMS-UHFFFAOYSA-M N-methylcarbamate Chemical compound CNC([O-])=O UFEJKYYYVXYMMS-UHFFFAOYSA-M 0.000 description 1
- IQRVRJMJNKERNO-UHFFFAOYSA-M N-prop-2-ynylcarbamate Chemical compound [O-]C(=O)NCC#C IQRVRJMJNKERNO-UHFFFAOYSA-M 0.000 description 1
- KNTZCGBYFGEMFR-UHFFFAOYSA-M N-propan-2-ylcarbamate Chemical compound CC(C)NC([O-])=O KNTZCGBYFGEMFR-UHFFFAOYSA-M 0.000 description 1
- KBJXDTIYSSQJAI-UHFFFAOYSA-M N-propylcarbamate Chemical compound CCCNC([O-])=O KBJXDTIYSSQJAI-UHFFFAOYSA-M 0.000 description 1
- 206010072736 Rheumatic disease Diseases 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N Sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- FEMYUNCOXYVXAB-UHFFFAOYSA-N [2-(hydroxymethyl)-2-methylhexyl] carbamate Chemical compound CCCCC(C)(CO)COC(N)=O FEMYUNCOXYVXAB-UHFFFAOYSA-N 0.000 description 1
- YLMQVJBJTFVYNN-UHFFFAOYSA-N [2-(hydroxymethyl)-2-methylpentyl] carbamate Chemical compound CCCC(C)(CO)COC(N)=O YLMQVJBJTFVYNN-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- XHODMTAOVMFHQJ-UHFFFAOYSA-N aluminum;propan-2-ol Chemical compound [Al].CC(C)O XHODMTAOVMFHQJ-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008079 hexane Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- AVIYEYCFMVPYST-UHFFFAOYSA-N hexane-1,3-diol Chemical compound CCCC(O)CCO AVIYEYCFMVPYST-UHFFFAOYSA-N 0.000 description 1
- 230000000147 hypnotic Effects 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 230000001077 hypotensive Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N isocyanate Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 230000000926 neurological Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 230000001624 sedative Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-M stearate Chemical compound CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- DSPYCWLYGXGJNJ-UHFFFAOYSA-N tert-butyl N-prop-2-ynylcarbamate Chemical compound CC(C)(C)OC(=O)NCC#C DSPYCWLYGXGJNJ-UHFFFAOYSA-N 0.000 description 1
- 230000002936 tranquilizing Effects 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE583826A true BE583826A (it) |
Family
ID=191414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE583826D BE583826A (it) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE583826A (it) |
-
0
- BE BE583826D patent/BE583826A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2937119A (en) | Nu-monosubstituted-2, 2-dialkyl-1, 3-propanediol dicarbamates | |
| WO2004020430A2 (fr) | Derives de dioxane-2-alkylcarbamates, leur preparation et leur application en therapeutique | |
| EP0927173B1 (fr) | [2-(1-piperazinyl)ethoxy]methyle substitues | |
| PL188805B1 (pl) | Sposób wytwarzania (S)-4-{[3-[2-(dimetyloamino)etylo]-1H-indol-5-ilo]metylo}-2-oksazolidynonu, związki pośrednie i sposoby ich wytwarzania | |
| CH645090A5 (fr) | Derives de phenylethylamine et leur preparation ainsi que composition contenant ces derives. | |
| EP0376850B1 (fr) | Dérivés du benzène, leur préparation et compositions pharmaceutiques les contenant | |
| BE885303A (fr) | Glycinamides | |
| BE583826A (it) | ||
| FR2534915A1 (fr) | Nouveaux derives de 2-(phenoxymethyl)-morpholine, utilisation en therapeutique et procede de preparation | |
| EP0585165B1 (fr) | Procédé de préparation d'isocyanates d'acyle | |
| BE567079A (it) | ||
| EP0820434B1 (fr) | Derives de la phenoxyethylamine possedant une haute affinite pour le recepteur 5-ht 1a, leur procede de preparation, leur application comme medicament et les compositions pharmaceutiques les renfermant | |
| CH407147A (fr) | Procédé de préparation de composés antitumoraux | |
| WO1995029154A1 (fr) | Nouveaux derives de benzylamines, leur procede de fabrication et les compositions pharmaceutiques les renfermant | |
| BE632153A (it) | ||
| FR2690917A1 (fr) | Aminoesters, leur procédé de préparation et leur application en thérapeutique. | |
| BE499947A (it) | ||
| BE799932A (fr) | Nouvelles 6-amino-s-triazinediones utiles comme herbicdes | |
| BE503348A (it) | ||
| BE482123A (it) | ||
| BE608019A (it) | ||
| FR2611716A1 (fr) | Derives de diisobutylxanthine substituee en position 7 utiles comme bronchodilatateurs, procede pour leur preparation et composition pharmaceutique les contenant | |
| CH352665A (fr) | Procédé de préparation de dicarbamates | |
| BE585646A (it) | ||
| CH395961A (fr) | Procédé de fabrication de carbamates organiques |