SE194405C1 - - Google Patents
Info
- Publication number
- SE194405C1 SE194405C1 SE194405DA SE194405C1 SE 194405 C1 SE194405 C1 SE 194405C1 SE 194405D A SE194405D A SE 194405DA SE 194405 C1 SE194405 C1 SE 194405C1
- Authority
- SE
- Sweden
- Prior art keywords
- pyrrolidinol
- phenyl
- methyl
- carbon atoms
- carbethoxy
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 26
- -1 benzyloxyphenyl Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000005059 halophenyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- PRMNSMIFUYOWSC-UHFFFAOYSA-N C(=O)(OCC)N1C(C(CC1C)(O)C1=CC=CC=C1)CC Chemical compound C(=O)(OCC)N1C(C(CC1C)(O)C1=CC=CC=C1)CC PRMNSMIFUYOWSC-UHFFFAOYSA-N 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- HJFUYFYPWSIFJV-UHFFFAOYSA-N ethyl 3-hydroxy-2,5-dimethyl-3-phenylpyrrolidine-1-carboxylate Chemical compound C(=O)(OCC)N1C(C(CC1C)(O)C1=CC=CC=C1)C HJFUYFYPWSIFJV-UHFFFAOYSA-N 0.000 claims description 2
- JANHNNQCVNYTNI-UHFFFAOYSA-N ethyl 4-hydroxy-2,4-diphenylpyrrolidine-1-carboxylate Chemical compound C(=O)(OCC)N1CC(CC1C1=CC=CC=C1)(O)C1=CC=CC=C1 JANHNNQCVNYTNI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical class OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims description 2
- JAYSWVYWAIPZCR-UHFFFAOYSA-N ethyl 4-hydroxy-2-methyl-4-phenylpyrrolidine-1-carboxylate Chemical compound C(=O)(OCC)N1CC(CC1C)(O)C1=CC=CC=C1 JAYSWVYWAIPZCR-UHFFFAOYSA-N 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 3
- 229910001863 barium hydroxide Inorganic materials 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- SAALQYKUFCIMHR-UHFFFAOYSA-N propan-2-ol;2-propan-2-yloxypropane Chemical compound CC(C)O.CC(C)OC(C)C SAALQYKUFCIMHR-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 101150043532 CISH gene Proteins 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- OYJXTOVLKZDGFK-UHFFFAOYSA-N ethanol;2-propan-2-yloxypropane Chemical compound CCO.CC(C)OC(C)C OYJXTOVLKZDGFK-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- NKDWRYOUSGSNJJ-UHFFFAOYSA-N 2,5-dimethyl-3-phenylpyrrolidin-3-ol;hydrochloride Chemical compound Cl.CC1NC(C)CC1(O)C1=CC=CC=C1 NKDWRYOUSGSNJJ-UHFFFAOYSA-N 0.000 description 1
- QPEUXHQMUXOAIA-UHFFFAOYSA-N 2-methyl-3-(3-phenylmethoxyphenyl)pyrrolidin-3-ol;hydrochloride Chemical compound Cl.CC1NCCC1(O)C1=CC=CC(OCC=2C=CC=CC=2)=C1 QPEUXHQMUXOAIA-UHFFFAOYSA-N 0.000 description 1
- BUQMQUWSTWDNBG-UHFFFAOYSA-N 2-methyl-3-(4-methylphenyl)pyrrolidin-3-ol;hydrochloride Chemical compound Cl.CC1NCCC1(O)C1=CC=C(C)C=C1 BUQMQUWSTWDNBG-UHFFFAOYSA-N 0.000 description 1
- VYHVKDVEVWIHKD-UHFFFAOYSA-N 2-methyl-3-phenylpyrrolidin-3-ol;hydrochloride Chemical compound Cl.CC1NCCC1(O)C1=CC=CC=C1 VYHVKDVEVWIHKD-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- VYZCCTOFRXJZTO-UHFFFAOYSA-N 3,5-diphenylpyrrolidin-3-ol;hydrochloride Chemical compound Cl.C1C(O)(C=2C=CC=CC=2)CNC1C1=CC=CC=C1 VYZCCTOFRXJZTO-UHFFFAOYSA-N 0.000 description 1
- WECKVPDFKUSCAG-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-2-methylpyrrolidin-3-ol;hydrochloride Chemical compound Cl.CC1NCCC1(O)C1=CC=C(Cl)C(Cl)=C1 WECKVPDFKUSCAG-UHFFFAOYSA-N 0.000 description 1
- IRJGVMDQSVUSIJ-UHFFFAOYSA-N 3-(3-chlorophenyl)-2-methylpyrrolidin-3-ol;hydrochloride Chemical compound Cl.CC1NCCC1(O)C1=CC=CC(Cl)=C1 IRJGVMDQSVUSIJ-UHFFFAOYSA-N 0.000 description 1
- NARUEBPJJJTZGM-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-methylpyrrolidin-3-ol;hydrochloride Chemical compound Cl.CC1NCCC1(O)C1=CC=C(Cl)C=C1 NARUEBPJJJTZGM-UHFFFAOYSA-N 0.000 description 1
- YTFWSWYRNPLHGY-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-phenylpyrrolidin-3-ol Chemical compound C1C(O)(C=2C=CC(Cl)=CC=2)CNC1C1=CC=CC=C1 YTFWSWYRNPLHGY-UHFFFAOYSA-N 0.000 description 1
- CTGVXLHYDXDBTA-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-phenylpyrrolidin-3-ol;hydrochloride Chemical compound Cl.C1C(O)(C=2C=CC(Cl)=CC=2)CNC1C1=CC=CC=C1 CTGVXLHYDXDBTA-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- UYKQKWDIZLZCBX-UHFFFAOYSA-N 5-(4-methoxyphenyl)-3-phenylpyrrolidin-3-ol Chemical compound C1=CC(OC)=CC=C1C1NCC(O)(C=2C=CC=CC=2)C1 UYKQKWDIZLZCBX-UHFFFAOYSA-N 0.000 description 1
- WDUGJEKIHPMTOH-UHFFFAOYSA-N 5-methyl-3-phenylpyrrolidin-3-ol Chemical compound C1NC(C)CC1(O)C1=CC=CC=C1 WDUGJEKIHPMTOH-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010046798 Uterine leiomyoma Diseases 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229940124572 antihypotensive agent Drugs 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- IPTRBHFYWILBCE-UHFFFAOYSA-N ethyl 3-hydroxy-2-methyl-3-phenylpyrrolidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(O)(C1C)C1=CC=CC=C1 IPTRBHFYWILBCE-UHFFFAOYSA-N 0.000 description 1
- AQCCUQNJHACLSY-UHFFFAOYSA-N ethyl 3-hydroxypyrrolidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(O)C1 AQCCUQNJHACLSY-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 201000010260 leiomyoma Diseases 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- RHMQNXNXUZLEIY-UHFFFAOYSA-N methanol;2-propan-2-yloxypropane Chemical compound OC.CC(C)OC(C)C RHMQNXNXUZLEIY-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- WEVSWKCMKXOKBQ-UHFFFAOYSA-N n,n,2,4,6-pentamethylbenzamide Chemical compound CN(C)C(=O)C1=C(C)C=C(C)C=C1C WEVSWKCMKXOKBQ-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 230000002541 vasodepressive effect Effects 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Landscapes
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE194405T |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE194405C1 true SE194405C1 (cs) | 1964-01-01 |
Family
ID=41980297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE194405D SE194405C1 (cs) |
Country Status (1)
| Country | Link |
|---|---|
| SE (1) | SE194405C1 (cs) |
-
0
- SE SE194405D patent/SE194405C1/sv unknown
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