BE550358A - - Google Patents
Info
- Publication number
- BE550358A BE550358A BE550358DA BE550358A BE 550358 A BE550358 A BE 550358A BE 550358D A BE550358D A BE 550358DA BE 550358 A BE550358 A BE 550358A
- Authority
- BE
- Belgium
- Prior art keywords
- carbon atoms
- methyl
- group
- fus
- alkyl
- Prior art date
Links
- -1 (for example Chemical group 0.000 claims description 27
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000008051 alkyl sulfates Chemical class 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 150000008050 dialkyl sulfates Chemical class 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000004429 atoms Chemical group 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 238000000354 decomposition reaction Methods 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- MUBZPKHOEPUJKR-UHFFFAOYSA-L oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000003921 oil Substances 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 239000000284 extract Substances 0.000 description 8
- 229920000591 gum Polymers 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 230000005712 crystallization Effects 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- MSYLETHDEIJMAF-UHFFFAOYSA-N 2,2-diphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(C(=O)Cl)C1=CC=CC=C1 MSYLETHDEIJMAF-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M Sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- XFZJGFIKQCCLGK-UHFFFAOYSA-M 1,1-dimethyl-4-phenylpiperazinium iodide Chemical compound [I-].C1C[N+](C)(C)CCN1C1=CC=CC=C1 XFZJGFIKQCCLGK-UHFFFAOYSA-M 0.000 description 2
- MDOFZALLRARRAF-UHFFFAOYSA-N 2,2-bis(4-methylphenyl)acetyl chloride Chemical compound C1=CC(C)=CC=C1C(C(Cl)=O)C1=CC=C(C)C=C1 MDOFZALLRARRAF-UHFFFAOYSA-N 0.000 description 2
- 229960004373 Acetylcholine Drugs 0.000 description 2
- 208000006218 Bradycardia Diseases 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- VZJFGSRCJCXDSG-UHFFFAOYSA-N Hexamethonium Chemical compound C[N+](C)(C)CCCCCC[N+](C)(C)C VZJFGSRCJCXDSG-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000036471 bradycardia Effects 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003457 ganglion blocking agent Substances 0.000 description 2
- 230000002496 gastric Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229950002932 hexamethonium Drugs 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000001631 hypertensive Effects 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 230000003389 potentiating Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 150000003385 sodium Chemical class 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 230000001515 vagal Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-O 1-methylpyrrolidin-1-ium Chemical compound C[NH+]1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-O 0.000 description 1
- YAQLSKVCTLCIIE-UHFFFAOYSA-M 2-bromobutanoate Chemical compound CCC(Br)C([O-])=O YAQLSKVCTLCIIE-UHFFFAOYSA-M 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 1
- HXHGULXINZUGJX-UHFFFAOYSA-N 4-chlorobutanol Chemical compound OCCCCCl HXHGULXINZUGJX-UHFFFAOYSA-N 0.000 description 1
- UUDBITGUQWFKPS-UHFFFAOYSA-N 4-chlorobutyl 2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C(=O)OCCCCCl)C1=CC=CC=C1 UUDBITGUQWFKPS-UHFFFAOYSA-N 0.000 description 1
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- NDTSRXAMMQDVSW-UHFFFAOYSA-N Benzthiazide Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1N=C2CSCC1=CC=CC=C1 NDTSRXAMMQDVSW-UHFFFAOYSA-N 0.000 description 1
- 210000001772 Blood Platelets Anatomy 0.000 description 1
- QGEXLENBFSTDMV-UHFFFAOYSA-M C(C)N(CCN(C)CC(=O)[O-])CC Chemical compound C(C)N(CCN(C)CC(=O)[O-])CC QGEXLENBFSTDMV-UHFFFAOYSA-M 0.000 description 1
- VWOYXMFIZOMELY-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(=O)OCCCCCCBr)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C(C(=O)OCCCCCCBr)C1=CC=CC=C1 VWOYXMFIZOMELY-UHFFFAOYSA-N 0.000 description 1
- JEICOVOKGJNPEQ-UHFFFAOYSA-M C1(=CC=CC=C1)C(CCC1CN(CCC1)CCN(C)CC(=O)[O-])C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C(CCC1CN(CCC1)CCN(C)CC(=O)[O-])C1=CC=CC=C1 JEICOVOKGJNPEQ-UHFFFAOYSA-M 0.000 description 1
- XFZSCRAPYWUYTD-UHFFFAOYSA-N CN(CCN1CCOCC1)CCCC(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound CN(CCN1CCOCC1)CCCC(=O)OC(C1=CC=CC=C1)C1=CC=CC=C1 XFZSCRAPYWUYTD-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N Ethyl iodide Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N Ethyl radical Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 210000003405 Ileum Anatomy 0.000 description 1
- SFLSHLFXELFNJZ-MRVPVSSYSA-N L-Noradrenaline Natural products NC[C@@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-MRVPVSSYSA-N 0.000 description 1
- 210000001165 Lymph Nodes Anatomy 0.000 description 1
- 208000006550 Mydriasis Diseases 0.000 description 1
- MKDYQLJYEBWUIG-UHFFFAOYSA-N N',N'-diethyl-N-methylethane-1,2-diamine Chemical compound CCN(CC)CCNC MKDYQLJYEBWUIG-UHFFFAOYSA-N 0.000 description 1
- GYGYDOOXVKDZCF-UHFFFAOYSA-N N-methyl-2-pyrrolidin-1-ylethanamine Chemical compound CNCCN1CCCC1 GYGYDOOXVKDZCF-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229960002748 Norepinephrine Drugs 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229940083599 Sodium Iodide Drugs 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000003042 antagnostic Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- YIOCIFXUGBYCJR-UHFFFAOYSA-N bis(4-chlorophenyl)acetic acid Chemical compound C=1C=C(Cl)C=CC=1C(C(=O)O)C1=CC=C(Cl)C=C1 YIOCIFXUGBYCJR-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- HOVYVWBNTMDKKB-UHFFFAOYSA-N ethyl 2-[2-(diethylamino)ethyl-methylamino]acetate Chemical compound CCOC(=O)CN(C)CCN(CC)CC HOVYVWBNTMDKKB-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000020828 fasting Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 230000000574 ganglionic Effects 0.000 description 1
- 239000008079 hexane Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- XSBSKEQEUFOSDD-UHFFFAOYSA-N pentolinium ion Chemical compound C1CCC[N+]1(C)CCCCC[N+]1(C)CCCC1 XSBSKEQEUFOSDD-UHFFFAOYSA-N 0.000 description 1
- 229950008637 pentolonium Drugs 0.000 description 1
- 230000002093 peripheral Effects 0.000 description 1
- 230000036378 peristaltic reflex Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000004936 stimulating Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical compound CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE550358A true BE550358A (nl) |
Family
ID=176275
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE550358D BE550358A (nl) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE550358A (nl) |
-
0
- BE BE550358D patent/BE550358A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1088939A (fr) | Medicaments derives de l'indole | |
| EP0231139B1 (fr) | Nouveaux dérivés de dihydrobenzofuranne - et de chromane -carboxamides, leurs procédés de préparation et leur utilisation comme neuroleptiques | |
| EP0307303A1 (fr) | [(Pyrimidinyl-2)-aminoalkyl]-1 pipéridines, leur préparation et leur application en thérapeutique | |
| EP1707564A2 (fr) | Derives d'indanyl-piperazines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
| FR2681325A1 (fr) | Derives de l'aminomethyl-4 piperidine, leur preparation et leur application en therapeutique. | |
| EP0343050B1 (fr) | Dérivés de phényl-6 pipérazinyl-alkyl-3 1H,3H-pyrimidinedione-2,4, leur préparation et leur application en thérapeutique | |
| FR2699918A1 (fr) | Ligands sélectifs des récepteurs 5HY1D-5HT1B dérivés d'indole-pipérazine utiles comme médicaments. | |
| EP0114850B1 (fr) | Nouveaux derives substitues du 2,5-diamino 1,4-diazole, leurs procedes de preparation et les compositions pharmaceutiques en renfermant | |
| EP0122827B1 (fr) | (Carbéthoxy-2 benzalkylamido-4 phénoxy)-1 amino-3 propanols-2, leurs préparations et leurs utilisations en thérapeutique | |
| EP0002978B1 (fr) | Dérivés de thiazolidinedione-2,4, leur préparation et leur application en thérapeutique | |
| CH542177A (fr) | Procédé de préparation d'amino-alcools et de leurs sels | |
| BE550358A (nl) | ||
| FR2634207A1 (fr) | Derives de ((piperidinyl-4)methyl) benzazepines, leur preparation et leur application en therapeutique | |
| CH625802A5 (en) | Process for the preparation of phenylpiperazine derivatives | |
| EP0105881B1 (fr) | Nouvelles cyanoguanidines, leur procede d'obtention et les compositions pharmaceutiques en renfermant | |
| CA1211441A (fr) | Procede de preparation de nouvelles piperidinoguanidines substituees, et des compositions pharmaceutiques en renfermant | |
| FR2702211A1 (fr) | Nouveaux dérivés de la phénoxy-2 éthylamine, leur préparation et leur application en thérapeutique. | |
| FR2572075A1 (fr) | Nouveaux derives de la 4-dioxino-(4,5-c)-pyridine et leur procede de preparation | |
| EP0106860B1 (fr) | Nouvelles carboxamidoguanidines, leur procede d'obtention et les compositions pharmaceutiques en renfermant | |
| EP0099822B1 (fr) | Nouveaux 1-(2-carbalkoxy 4-(thiénylalkylamido)phénoxy) 3-amino 2-propanols, leur préparation et leurs applications en thérapeutique | |
| BE484419A (nl) | ||
| BE535964A (nl) | ||
| BE671440A (nl) | ||
| BE488997A (nl) | ||
| BE873102A (fr) | Composes de l'ether aminophenylique utilises pour le traitement de l'arteriosclerose |