BE541782A - - Google Patents
Info
- Publication number
- BE541782A BE541782A BE541782DA BE541782A BE 541782 A BE541782 A BE 541782A BE 541782D A BE541782D A BE 541782DA BE 541782 A BE541782 A BE 541782A
- Authority
- BE
- Belgium
- Prior art keywords
- compound
- grams
- radical
- formula
- alpha
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 23
- -1 alkyl radical Chemical class 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 10
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000007818 Grignard reagent Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 229940124630 bronchodilator Drugs 0.000 description 7
- 230000008602 contraction Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 150000004795 grignard reagents Chemical class 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
- 241000700199 Cavia porcellus Species 0.000 description 5
- 229960001340 histamine Drugs 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000007059 acute toxicity Effects 0.000 description 4
- 231100000403 acute toxicity Toxicity 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007928 intraperitoneal injection Substances 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 230000003000 nontoxic effect Effects 0.000 description 4
- 150000003254 radicals Chemical group 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 210000005062 tracheal ring Anatomy 0.000 description 4
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical group C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 3
- 229960004373 acetylcholine Drugs 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 3
- 229960002179 ephedrine Drugs 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- FPLIHNQJYDCWBM-UHFFFAOYSA-N 2-bromo-1-(2-methoxyphenyl)propan-1-one Chemical compound COC1=CC=CC=C1C(=O)C(C)Br FPLIHNQJYDCWBM-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 2
- 229910001626 barium chloride Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UJEPWZNKGOLNCD-UHFFFAOYSA-N 2-(benzylamino)-1-(2-methoxyphenyl)propan-1-one Chemical compound COC1=CC=CC=C1C(=O)C(C)NCC1=CC=CC=C1 UJEPWZNKGOLNCD-UHFFFAOYSA-N 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-butanol Substances CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical class II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- FGSJNNQVSUVTPW-UHFFFAOYSA-N methoxyphenamine hydrochloride Chemical compound Cl.CNC(C)CC1=CC=CC=C1OC FGSJNNQVSUVTPW-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE541782A true BE541782A (de) |
Family
ID=170649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE541782D BE541782A (de) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE541782A (de) |
-
0
- BE BE541782D patent/BE541782A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| LU82387A1 (fr) | Esters d'acyl-carnitines,leur procede de preparation et compositions pharmaceutiques contenant ces esters | |
| EP0042781A1 (de) | 1-(4- Chinolyl), 2- oder 3- (2- oder 3-piperidyl oder pyrrolidinyl)-Äthanon oder -Propanon, Verfahren zu seiner Herstellung und seine Anwendung als Arzneimittel | |
| FR2658513A1 (fr) | Procede de preparation de l'acide cis-beta-phenylglycidique-(2r,3r). | |
| EP0073161A1 (de) | Pyridazin-Derivate mit einer Wirkung auf das Zentralnervensystem | |
| CH630606A5 (en) | Phenylamidine derivatives useful especially in therapeutics | |
| EP0119107B1 (de) | Bicyclo(4.2.0)oktatriene-1,3,5 Derivate, Verfahren zu deren Herstellung und deren therapeutische Anwendung | |
| EP0017543A1 (de) | Benzothiazolderivate, Verfahren zu ihrer Herstellung und ihre therapeutischen Anwendungen | |
| CA1088099A (fr) | Procede de preparation de nouveaux alcoxy anilides et composes ainsi obtenus | |
| EP0035925A1 (de) | 3-Chlorchinolinderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| BE776316R (fr) | Nouveaux derives d'acides phenyl-acetiques substitues et procede pour leur | |
| EP0354078B1 (de) | Derivate von Benzocyclohepten, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel | |
| CH618977A5 (de) | ||
| FR2491471A1 (fr) | Benzoxazolinones substituees, leur preparation et leur application en therapeutique | |
| EP0837843B1 (de) | Verfahren zur herstellung von enantiomeren der aminoalkylaminophenylpropansäure | |
| BE818471A (fr) | Procede pour preparer des 1-aralkyl-4-amino-methylpiperidine-4-ols | |
| CA1097682A (fr) | Procede d'obtention de derives de l'acide phenylacetique | |
| BE633474A (de) | ||
| BE901066A (fr) | Composes chimiues intermediiares pour la preparation d'aniline substituee et procede de preparation. | |
| BE497580A (de) | ||
| CH516523A (fr) | Procédé de préparation des dérivés des acides a-aminés N-disubstitués par benzoylation | |
| BE539933A (de) | ||
| CH624094A5 (en) | Process for the preparation of 5-amino-2-propargyloxy-N-n-butylbenzamide | |
| CH321872A (fr) | Procédé de préparation d'halogéno-2-amino-2'-diphénylsulfures | |
| CH314549A (fr) | Procédé de préparation d'un 1-p-nitrophényl-2-acylamido-propanediol-1,3 | |
| BE525695A (de) |