CH475190A - Verfahren zur Herstellung von neuen tertiären Aminen - Google Patents
Verfahren zur Herstellung von neuen tertiären AminenInfo
- Publication number
- CH475190A CH475190A CH1401167A CH1401167A CH475190A CH 475190 A CH475190 A CH 475190A CH 1401167 A CH1401167 A CH 1401167A CH 1401167 A CH1401167 A CH 1401167A CH 475190 A CH475190 A CH 475190A
- Authority
- CH
- Switzerland
- Prior art keywords
- dependent
- mol
- ether
- group
- radical
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000003512 tertiary amines Chemical class 0.000 title claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 84
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 42
- -1 aralkyl radical Chemical group 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 14
- 150000002576 ketones Chemical class 0.000 claims description 8
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001302 tertiary amino group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 150000005840 aryl radicals Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 2
- 239000000463 material Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 86
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 51
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 32
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 26
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 21
- 239000011777 magnesium Substances 0.000 description 21
- 229910052749 magnesium Inorganic materials 0.000 description 21
- 239000002585 base Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 19
- 235000011121 sodium hydroxide Nutrition 0.000 description 16
- 235000019270 ammonium chloride Nutrition 0.000 description 13
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000000284 extract Substances 0.000 description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 239000011630 iodine Substances 0.000 description 8
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 4
- BTEPCCLXMPVCIW-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-1,2-diphenylbut-3-en-2-ol Chemical compound C1(=CC=CC=C1)CC(C(=C)CN(C)C)(O)C1=CC=CC=C1 BTEPCCLXMPVCIW-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229940095064 tartrate Drugs 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- MKXIEWUWYKGNNB-UHFFFAOYSA-N 1-(2-bromoprop-2-enyl)pyrrolidine Chemical compound BrC(=C)CN1CCCC1 MKXIEWUWYKGNNB-UHFFFAOYSA-N 0.000 description 2
- YMFWYDYJHRGGPF-UHFFFAOYSA-N 2,3-dibromoprop-1-ene Chemical compound BrCC(Br)=C YMFWYDYJHRGGPF-UHFFFAOYSA-N 0.000 description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229960001270 d- tartaric acid Drugs 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- QGGZBXOADPVUPN-UHFFFAOYSA-N dihydrochalcone Chemical compound C=1C=CC=CC=1C(=O)CCC1=CC=CC=C1 QGGZBXOADPVUPN-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229960001367 tartaric acid Drugs 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 150000003892 tartrate salts Chemical class 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- PBHOMCCEZCLALM-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)butan-1-one Chemical compound C=1C=C(OC)C=CC=1C(CC)C(=O)C1=CC=C(OC)C=C1 PBHOMCCEZCLALM-UHFFFAOYSA-N 0.000 description 1
- SICBLYCPRWNHHP-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethanone Chemical compound C1=CC(OC)=CC=C1CC(=O)C1=CC=C(OC)C=C1 SICBLYCPRWNHHP-UHFFFAOYSA-N 0.000 description 1
- MEUFKDJSKZVDDR-UHFFFAOYSA-N 1,2-diphenyl-3-(piperidin-1-ylmethyl)but-3-en-2-ol hydrochloride Chemical compound Cl.C1(=CC=CC=C1)CC(C(=C)CN1CCCCC1)(O)C1=CC=CC=C1 MEUFKDJSKZVDDR-UHFFFAOYSA-N 0.000 description 1
- HTLVFVWPOZVZCG-UHFFFAOYSA-N 1,2-diphenyl-3-(pyrrolidin-1-ylmethyl)but-3-en-2-ol Chemical compound C1(=CC=CC=C1)CC(C(=C)CN1CCCC1)(O)C1=CC=CC=C1 HTLVFVWPOZVZCG-UHFFFAOYSA-N 0.000 description 1
- VPQXGYRPWUTDSY-UHFFFAOYSA-N 1,2-diphenyl-3-(pyrrolidin-1-ylmethyl)but-3-en-2-ol hydrochloride Chemical compound Cl.C1(=CC=CC=C1)CC(C(=C)CN1CCCC1)(O)C1=CC=CC=C1 VPQXGYRPWUTDSY-UHFFFAOYSA-N 0.000 description 1
- UHKJKVIZTFFFSB-UHFFFAOYSA-N 1,2-diphenylbutan-1-one Chemical compound C=1C=CC=CC=1C(CC)C(=O)C1=CC=CC=C1 UHKJKVIZTFFFSB-UHFFFAOYSA-N 0.000 description 1
- ARTRALZMYCCNTK-UHFFFAOYSA-N 1-(2-bromoprop-2-enyl)piperidine Chemical compound BrC(=C)CN1CCCCC1 ARTRALZMYCCNTK-UHFFFAOYSA-N 0.000 description 1
- DXVALSKCLLBZEB-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-phenylethanone Chemical compound C1=CC(Cl)=CC=C1C(=O)CC1=CC=CC=C1 DXVALSKCLLBZEB-UHFFFAOYSA-N 0.000 description 1
- GUXXMLZIXGCSQC-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[(dimethylamino)methyl]-2-phenylbut-3-en-2-ol Chemical compound ClC1=CC=C(C=C1)CC(C(=C)CN(C)C)(O)C1=CC=CC=C1 GUXXMLZIXGCSQC-UHFFFAOYSA-N 0.000 description 1
- PLALKSRAHVYFOH-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-phenylethanone Chemical compound C1=CC(OC)=CC=C1C(=O)CC1=CC=CC=C1 PLALKSRAHVYFOH-UHFFFAOYSA-N 0.000 description 1
- QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
- ROQNLBXZWMNUCU-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-[(dimethylamino)methyl]-1-phenylbut-3-en-2-ol Chemical compound C1(=CC=CC=C1)CC(C(=C)CN(C)C)(O)C1=CC=C(C=C1)Cl ROQNLBXZWMNUCU-UHFFFAOYSA-N 0.000 description 1
- VTBMXYMZRUZNFT-UHFFFAOYSA-N 3-(diethylaminomethyl)-1,2-diphenylbut-3-en-2-ol hydrochloride Chemical compound Cl.C1(=CC=CC=C1)CC(C(=C)CN(CC)CC)(O)C1=CC=CC=C1 VTBMXYMZRUZNFT-UHFFFAOYSA-N 0.000 description 1
- DEEPSEKAUPPTCG-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-1,2-bis(4-methoxyphenyl)but-3-en-2-ol hydrochloride Chemical compound Cl.COC1=CC=C(C=C1)CC(C(=C)CN(C)C)(O)C1=CC=C(C=C1)OC DEEPSEKAUPPTCG-UHFFFAOYSA-N 0.000 description 1
- XFDLKOZYWQJLGD-UHFFFAOYSA-N 3-[(dimethylamino)methyl]-1-(4-methoxyphenyl)-2-phenylbut-3-en-2-ol Chemical compound COC1=CC=C(C=C1)CC(C(=C)CN(C)C)(O)C1=CC=CC=C1 XFDLKOZYWQJLGD-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- WULUXBDZOYFOKX-UHFFFAOYSA-N Cl.C1(=CC=CC=C1)CC(C(=C)CN(C)C)(O)C1=CC=CC=C1 Chemical compound Cl.C1(=CC=CC=C1)CC(C(=C)CN(C)C)(O)C1=CC=CC=C1 WULUXBDZOYFOKX-UHFFFAOYSA-N 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-L D-tartrate(2-) Chemical compound [O-]C(=O)[C@@H](O)[C@H](O)C([O-])=O FEWJPZIEWOKRBE-LWMBPPNESA-L 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- NLOUUOHFCQJOCA-UHFFFAOYSA-N bis(2-benzyl-4-chlorophenyl)methanone Chemical compound C=1C=CC=CC=1CC1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1CC1=CC=CC=C1 NLOUUOHFCQJOCA-UHFFFAOYSA-N 0.000 description 1
- SXMRBHBGBZCJHV-UHFFFAOYSA-N bis(2-benzyl-4-methoxyphenyl)methanone Chemical compound C=1C=CC=CC=1CC1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1CC1=CC=CC=C1 SXMRBHBGBZCJHV-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229940099690 malic acid Drugs 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 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
- C07D295/092—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 with aromatic radicals attached to the chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Remote Monitoring And Control Of Power-Distribution Networks (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH267765A CH465584A (de) | 1965-02-26 | 1965-02-26 | Verfahren zur Herstellung von neuen tertiären Aminen |
| CH902865 | 1965-06-28 | ||
| CH1311165 | 1965-09-22 | ||
| CH1811865 | 1965-12-30 | ||
| CH1811965 | 1965-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH475190A true CH475190A (de) | 1969-07-15 |
Family
ID=27509073
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1401167A CH475190A (de) | 1965-02-26 | 1965-02-26 | Verfahren zur Herstellung von neuen tertiären Aminen |
| CH267765A CH465584A (de) | 1965-02-26 | 1965-02-26 | Verfahren zur Herstellung von neuen tertiären Aminen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH267765A CH465584A (de) | 1965-02-26 | 1965-02-26 | Verfahren zur Herstellung von neuen tertiären Aminen |
Country Status (16)
| Country | Link |
|---|---|
| BE (3) | BE677035A (pm) |
| BR (3) | BR6677337D0 (pm) |
| CH (2) | CH475190A (pm) |
| CY (1) | CY556A (pm) |
| DE (2) | DE1793640B1 (pm) |
| DK (3) | DK118601B (pm) |
| FI (1) | FI44601C (pm) |
| FR (4) | FR1468478A (pm) |
| GB (3) | GB1068497A (pm) |
| IL (1) | IL25127A (pm) |
| LU (1) | LU50473A1 (pm) |
| MY (1) | MY7000162A (pm) |
| NL (3) | NL6602536A (pm) |
| NO (1) | NO115389B (pm) |
| SE (3) | SE348454B (pm) |
| SU (1) | SU372806A3 (pm) |
-
1965
- 1965-02-26 CH CH1401167A patent/CH475190A/de not_active IP Right Cessation
- 1965-02-26 CH CH267765A patent/CH465584A/de unknown
-
1966
- 1966-02-07 IL IL2512766A patent/IL25127A/xx unknown
- 1966-02-08 GB GB547166A patent/GB1068497A/en not_active Expired
- 1966-02-08 GB GB547366A patent/GB1117623A/en not_active Expired
- 1966-02-08 GB GB547266A patent/GB1117622A/en not_active Expired
- 1966-02-16 LU LU50473A patent/LU50473A1/xx unknown
- 1966-02-17 FR FR50038A patent/FR1468478A/fr not_active Expired
- 1966-02-17 DE DE19661793640 patent/DE1793640B1/de active Pending
- 1966-02-17 DE DE19661568254 patent/DE1568254A1/de active Pending
- 1966-02-17 FR FR50039A patent/FR1468479A/fr not_active Expired
- 1966-02-23 FI FI44866A patent/FI44601C/fi active
- 1966-02-24 BR BR17733766A patent/BR6677337D0/pt unknown
- 1966-02-24 BR BR17733666A patent/BR6677336D0/pt unknown
- 1966-02-24 BR BR17734466A patent/BR6677344D0/pt unknown
- 1966-02-25 NL NL6602536A patent/NL6602536A/xx unknown
- 1966-02-25 SE SE246766A patent/SE348454B/xx unknown
- 1966-02-25 BE BE677035D patent/BE677035A/xx unknown
- 1966-02-25 DK DK98566A patent/DK118601B/da unknown
- 1966-02-25 NL NL6602537A patent/NL6602537A/xx unknown
- 1966-02-25 BE BE677036D patent/BE677036A/xx unknown
- 1966-02-25 NO NO16185366A patent/NO115389B/no unknown
- 1966-02-25 DK DK98666A patent/DK123023B/da unknown
- 1966-02-25 BE BE677034D patent/BE677034A/xx unknown
- 1966-02-25 SE SE246566A patent/SE325266B/xx unknown
- 1966-02-25 NL NL6602535A patent/NL6602535A/xx unknown
- 1966-02-25 SE SE246666A patent/SE348724B/xx unknown
- 1966-02-25 DK DK98766A patent/DK122878B/da unknown
- 1966-03-29 SU SU1064790A patent/SU372806A3/ru active
- 1966-05-10 FR FR60915A patent/FR5349M/fr not_active Expired
- 1966-05-10 FR FR60914A patent/FR5348M/fr not_active Expired
-
1970
- 1970-08-19 CY CY55670A patent/CY556A/xx unknown
- 1970-12-31 MY MY7000162A patent/MY7000162A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1117623A (en) | 1968-06-19 |
| DE1568253B1 (de) | 1971-07-29 |
| FR5349M (pm) | 1967-09-04 |
| DK122878B (da) | 1972-04-24 |
| FR1468478A (fr) | 1967-02-03 |
| DE1568252B2 (de) | 1973-01-04 |
| SE348454B (pm) | 1972-09-04 |
| FR5348M (pm) | 1967-09-04 |
| BE677036A (pm) | 1966-08-25 |
| NO115389B (pm) | 1968-09-30 |
| DE1568252A1 (de) | 1971-06-24 |
| GB1117622A (en) | 1968-06-19 |
| SE348724B (pm) | 1972-09-11 |
| FR1468479A (fr) | 1967-02-03 |
| DK123023B (da) | 1972-05-08 |
| FI44601B (pm) | 1971-08-31 |
| SE325266B (pm) | 1970-06-29 |
| GB1068497A (en) | 1967-05-10 |
| DE1793640B1 (de) | 1973-04-26 |
| CH465584A (de) | 1968-11-30 |
| LU50473A1 (pm) | 1966-04-18 |
| MY7000162A (en) | 1970-12-31 |
| NL6602537A (pm) | 1966-08-29 |
| NL6602536A (pm) | 1966-08-29 |
| BE677034A (pm) | 1966-08-25 |
| DK118601B (da) | 1970-09-14 |
| BR6677344D0 (pt) | 1973-09-06 |
| DE1568254A1 (de) | 1970-03-19 |
| BR6677336D0 (pt) | 1973-09-20 |
| BR6677337D0 (pt) | 1973-09-06 |
| IL25127A (en) | 1969-12-31 |
| BE677035A (pm) | 1966-08-25 |
| SU372806A3 (pm) | 1973-03-01 |
| NL6602535A (pm) | 1966-08-29 |
| FI44601C (fi) | 1971-12-10 |
| CY556A (en) | 1970-08-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |