DES0031249MA - - Google Patents
Info
- Publication number
- DES0031249MA DES0031249MA DES0031249MA DE S0031249M A DES0031249M A DE S0031249MA DE S0031249M A DES0031249M A DE S0031249MA
- Authority
- DE
- Germany
- Prior art keywords
- piperidine
- amount
- methyl
- abs
- alcohol
- 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.)
- Active
Links
- 239000000460 chlorine Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 241000251730 Chondrichthyes Species 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- LKRMTUUCKBQGFO-UHFFFAOYSA-N N-phenylpiperidin-4-amine Chemical class C1CNCCC1NC1=CC=CC=C1 LKRMTUUCKBQGFO-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 14
- 239000008096 xylene Substances 0.000 description 14
- 239000002585 base Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ODZPKZBBUMBTMG-UHFFFAOYSA-N Sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 6
- 229940095064 tartrate Drugs 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000001476 alcoholic Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-L oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 3
- FUOHKPSBGLXIRL-UHFFFAOYSA-N 2-(chloromethyl)thiophene Chemical compound ClCC1=CC=CS1 FUOHKPSBGLXIRL-UHFFFAOYSA-N 0.000 description 2
- RGAWORKAZJRWOL-UHFFFAOYSA-N 2-bromo-5-(chloromethyl)thiophene Chemical compound ClCC1=CC=C(Br)S1 RGAWORKAZJRWOL-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000036880 Cls Effects 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 150000003053 piperidines Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 229960001367 tartaric acid Drugs 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- MQTKXCOGYOYAMW-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)thiophene Chemical compound ClCC1=CC=C(Cl)S1 MQTKXCOGYOYAMW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- KMJZFJMFHOPFPJ-UHFFFAOYSA-N N-phenylpiperidin-1-amine Chemical compound C1CCCCN1NC1=CC=CC=C1 KMJZFJMFHOPFPJ-UHFFFAOYSA-N 0.000 description 1
- KJFMBFZCATUALV-UHFFFAOYSA-N Phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 101710024753 SERPINB14 Proteins 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Family
ID=
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69103206T2 (de) | Neue Derivate des Aminopiperidins, Aminopyrrolidins und des Aminoperhydroazepins, Verfahren zur Herstellung und diese enthaltende Arzneimittel. | |
| DE2503815C2 (de) | Indazol-Derivate, Verfahren zu ihrer Herstellung und Arzneimittel | |
| DE897405C (de) | Verfahren zur Herstellung substituierter Piperazine | |
| DE1249281B (xx) | ||
| US2846437A (en) | Lower alkyl 4-phenyl-1-(substituted-alkyl) piperidine-4-carboxylates and preparationthereof | |
| DE2313258A1 (de) | Verfahren zur herstellung von butyrophenonderivaten und ihren salzen neue butyrophenonderivate, ihre salze und diese verbindungen enthaltende arzneimittel | |
| WO1999062893A2 (de) | Neue neurokininantagonisten, verfahren zu ihrer herstellung und diese verbindungen enthaltende pharmazeutische zusammensetzungen | |
| DE2167193C2 (de) | 4-(4-Hydroxypiperidino)-N,N,3-trimethyl-2,2-diphenylbutyramide und Verfahren zu ihrer Herstellung | |
| DE2426149B2 (de) | 7-Fluor-substituierte Phenothiazine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel | |
| DE1493454C3 (de) | 1 -Aryloxy^-hydroxy-S-isopropylaminopropane und deren Salze sowie deren Herstellung und darauf basierende Arzneimittel | |
| DE2642856A1 (de) | N-aryl-n-(4-piperidinyl)-arylacetamide, verfahren zu ihrer herstellung und arzneimittel | |
| DE961348C (de) | Verfahren zur Herstellung neuer 4-(Phenylamino)-piperidin-verbindungen | |
| DES0031249MA (xx) | ||
| DE2456098C3 (de) | Xanthen- und Thioxanthen-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE1620746A1 (de) | Verfahren zur Herstellung von Phenothiazin-Derivaten | |
| DE1090667B (de) | Verfahren zur Herstellung von basischen Phenthiazinderivaten | |
| DE1959365B2 (de) | Basische N-[2-(2- Phenylbicydo-(2i,l)-heptyl]carbamate | |
| DE1006421B (de) | Verfahren zur Herstellung von basischen Derivaten des Iminodibenzyls | |
| US3093651A (en) | Nu-alkyl-2-(2-[9-carbazolyl-ethyl])-piperidines | |
| DE964048C (de) | Verfahren zur Herstellung neuer, antihistaminwirksamer Piperazinabkoemmlinge | |
| DE1287582B (de) | Verfahren zur Herstellung von disubstituierten Isoxazol-Verbindungen und ihrer nicht toxischen Salze | |
| DE2065426A1 (de) | Phenylbutanol-derivate, ihre salze, verfahren zu ihrer herstellung und die verbindungen enthaltende arzneimittel | |
| DE1937629A1 (de) | Nitrofuryl-aminoalkoxy-pyrimidine | |
| DE1643265C3 (de) | Kernsubstituierte 2-Aminomethylbenzhydrole, Verfahren zu deren Herstellung und Arzneimittel auf der Basis dieser Verbindungen | |
| DE3151123A1 (de) | 1,4-disubstituierte piperazinderivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitungen |