FI56825C - Foerfarande foer framstaellning av nya analgetiska basiska etrar - Google Patents
Foerfarande foer framstaellning av nya analgetiska basiska etrar Download PDFInfo
- Publication number
- FI56825C FI56825C FI2048/73A FI204873A FI56825C FI 56825 C FI56825 C FI 56825C FI 2048/73 A FI2048/73 A FI 2048/73A FI 204873 A FI204873 A FI 204873A FI 56825 C FI56825 C FI 56825C
- Authority
- FI
- Finland
- Prior art keywords
- diphenyl
- melting point
- methoxy
- hydrochloride
- methyl
- Prior art date
Links
- -1 p-methoxystyryl Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 230000000202 analgesic effect Effects 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 claims description 2
- 230000008018 melting Effects 0.000 description 89
- 238000002844 melting Methods 0.000 description 89
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 9
- 229960005181 morphine Drugs 0.000 description 8
- 239000012280 lithium aluminium hydride Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 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 6
- PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- AAPCZJAWDPTWIO-UHFFFAOYSA-N 3-methoxy-3,3-diphenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(CCN)(OC)C1=CC=CC=C1 AAPCZJAWDPTWIO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OMEMHWMGDBHTCD-UHFFFAOYSA-N N-(3,3-diphenyl-3-propoxypropyl)cyclopropanecarboxamide Chemical compound C1(=CC=CC=C1)C(CCNC(=O)C1CC1)(OCCC)C1=CC=CC=C1 OMEMHWMGDBHTCD-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- FDLVCUOMIAFXNG-UHFFFAOYSA-N methyl(propyl)azanium;chloride Chemical compound Cl.CCCNC FDLVCUOMIAFXNG-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- IEFKUTPZOQYRDT-UHFFFAOYSA-N 4-cyclopropyl-1-methoxy-n,2-dimethyl-1,1-diphenylbutan-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(OC)(C=1C=CC=CC=1)C(C)(NC)CCC1CC1 IEFKUTPZOQYRDT-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- NGJBPROVKSOQSL-UHFFFAOYSA-N N-(3-methoxy-2-methyl-3,3-diphenylpropyl)cyclobutanecarboxamide Chemical compound C1(=CC=CC=C1)C(C(CNC(=O)C1CCC1)C)(OC)C1=CC=CC=C1 NGJBPROVKSOQSL-UHFFFAOYSA-N 0.000 description 2
- HWNRYDPLYDPFKC-UHFFFAOYSA-N N-(3-methoxy-3,3-diphenylpropyl)-3-phenylprop-2-enamide Chemical compound C1(=CC=CC=C1)C(CCNC(C=CC1=CC=CC=C1)=O)(OC)C1=CC=CC=C1 HWNRYDPLYDPFKC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000004645 aluminates Chemical class 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000019788 craving Nutrition 0.000 description 2
- JFWMYCVMQSLLOO-UHFFFAOYSA-N cyclobutanecarbonyl chloride Chemical compound ClC(=O)C1CCC1 JFWMYCVMQSLLOO-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- QGJNZWVMCBLAGI-UHFFFAOYSA-N methyl(propyl)azanium chloride hydrate Chemical compound O.Cl.CNCCC QGJNZWVMCBLAGI-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
- MXYGYQZXMYSNTP-UHFFFAOYSA-N 1-butoxy-4-cyclopropyl-1,1-diphenylbutan-2-amine Chemical compound C1(=CC=CC=C1)C(C(CCC1CC1)N)(OCCCC)C1=CC=CC=C1 MXYGYQZXMYSNTP-UHFFFAOYSA-N 0.000 description 1
- LWODVWRXCVHRBX-UHFFFAOYSA-N 1-butoxy-5-cyclohexylidene-1,1-diphenylpentan-2-amine Chemical compound C1(=CC=CC=C1)C(C(CCC=C1CCCCC1)N)(OCCCC)C1=CC=CC=C1 LWODVWRXCVHRBX-UHFFFAOYSA-N 0.000 description 1
- VNYJGSDKEOQUFH-UHFFFAOYSA-N 1-methoxy-2-methyl-1,1,6-triphenylhex-5-en-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C(C)(N)CCC=CC=1C=CC=CC=1)(OC)C1=CC=CC=C1 VNYJGSDKEOQUFH-UHFFFAOYSA-N 0.000 description 1
- JSVPTUKQHLNUHR-UHFFFAOYSA-N 1-methoxy-n-methyl-1,1-diphenylhex-5-yn-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(OC)(C(CCC#C)NC)C1=CC=CC=C1 JSVPTUKQHLNUHR-UHFFFAOYSA-N 0.000 description 1
- NUURMPYWJOPYSC-UHFFFAOYSA-N 2-(cyclopropylmethyl)-1-ethoxy-1,1,4-triphenylbutan-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C(N)(CCC=1C=CC=CC=1)CC1CC1)(OCC)C1=CC=CC=C1 NUURMPYWJOPYSC-UHFFFAOYSA-N 0.000 description 1
- OBJUOZNLADRGSY-UHFFFAOYSA-N 2-methyl-1,1,6-triphenyl-1-propoxyhex-5-en-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C(C)(N)CCC=CC=1C=CC=CC=1)(OCCC)C1=CC=CC=C1 OBJUOZNLADRGSY-UHFFFAOYSA-N 0.000 description 1
- LVGZJQSCXZRTBW-UHFFFAOYSA-N 3,3-diphenyl-3-propoxypropan-1-amine Chemical compound C=1C=CC=CC=1C(CCN)(OCCC)C1=CC=CC=C1 LVGZJQSCXZRTBW-UHFFFAOYSA-N 0.000 description 1
- BNCLOELSTVUCSF-UHFFFAOYSA-N 3-ethoxy-3,3-diphenyl-n-(3-phenylprop-2-enyl)propan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCC)CCNCC=CC1=CC=CC=C1 BNCLOELSTVUCSF-UHFFFAOYSA-N 0.000 description 1
- FJCUOCVYQKQNGU-UHFFFAOYSA-N 3-ethoxy-3,3-diphenyl-n-prop-2-ynylpropan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CCNCC#C)(OCC)C1=CC=CC=C1 FJCUOCVYQKQNGU-UHFFFAOYSA-N 0.000 description 1
- QKCOKEIMHOFEHO-UHFFFAOYSA-N 3-methoxy-2-methylpropan-1-amine Chemical compound COCC(C)CN QKCOKEIMHOFEHO-UHFFFAOYSA-N 0.000 description 1
- ODGSKZGDQUQMLA-UHFFFAOYSA-N 3-methoxy-3,3-diphenyl-N-(3-phenylprop-2-enyl)propan-1-amine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC)CCNCC=CC1=CC=CC=C1 ODGSKZGDQUQMLA-UHFFFAOYSA-N 0.000 description 1
- VSCPIAIKUBKNGB-UHFFFAOYSA-N 3-methoxy-3,3-diphenyl-n-prop-2-ynylpropan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CCNCC#C)(OC)C1=CC=CC=C1 VSCPIAIKUBKNGB-UHFFFAOYSA-N 0.000 description 1
- BDUBTLFQHNYXPC-UHFFFAOYSA-N 3-methylbut-2-enoyl chloride Chemical compound CC(C)=CC(Cl)=O BDUBTLFQHNYXPC-UHFFFAOYSA-N 0.000 description 1
- GZRVJOJFJHCOJA-UHFFFAOYSA-N 4-cyclobutyl-1-ethoxy-n-methyl-1,1-diphenylbutan-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCC)C(NC)CCC1CCC1 GZRVJOJFJHCOJA-UHFFFAOYSA-N 0.000 description 1
- FPRLZDTYZUPIKM-UHFFFAOYSA-N 4-cyclobutyl-1-methoxy-2-methyl-1,1-diphenylbutan-2-amine Chemical compound C=1C=CC=CC=1C(C(C)(N)CCC1CCC1)(OC)C1=CC=CC=C1 FPRLZDTYZUPIKM-UHFFFAOYSA-N 0.000 description 1
- ILZVYZNIWKZMMD-UHFFFAOYSA-N 4-cyclobutyl-1-methoxy-n,2-dimethyl-1,1-diphenylbutan-2-amine;hydrobromide Chemical compound Br.C=1C=CC=CC=1C(OC)(C=1C=CC=CC=1)C(C)(NC)CCC1CCC1 ILZVYZNIWKZMMD-UHFFFAOYSA-N 0.000 description 1
- JGIFRJSFLLJBTK-UHFFFAOYSA-N 4-cyclopropyl-1,1-diphenyl-1-propoxybutan-2-amine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCCC)C(N)CCC1CC1 JGIFRJSFLLJBTK-UHFFFAOYSA-N 0.000 description 1
- MQJVXIALIAVVQV-UHFFFAOYSA-N 4-cyclopropyl-1-ethoxy-1,1-diphenylbutan-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCC)C(N)CCC1CC1 MQJVXIALIAVVQV-UHFFFAOYSA-N 0.000 description 1
- IJDVREQJIQGPHH-UHFFFAOYSA-N 4-cyclopropyl-1-ethoxy-n-methyl-1,1-diphenylbutan-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCC)C(NC)CCC1CC1 IJDVREQJIQGPHH-UHFFFAOYSA-N 0.000 description 1
- GZOQUDPYTCTWEU-UHFFFAOYSA-N 4-cyclopropyl-1-methoxy-1,1-diphenylbutan-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC)C(N)CCC1CC1 GZOQUDPYTCTWEU-UHFFFAOYSA-N 0.000 description 1
- BEFRDPVUJZBNJT-UHFFFAOYSA-N 4-cyclopropyl-1-methoxy-n-methyl-1,1-diphenylbutan-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(OC)(C=1C=CC=CC=1)C(NC)CCC1CC1 BEFRDPVUJZBNJT-UHFFFAOYSA-N 0.000 description 1
- AHNZCCRQIRWGPR-UHFFFAOYSA-N 4-cyclopropyl-n-methyl-1,1-diphenyl-1-propoxybutan-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCCC)C(NC)CCC1CC1 AHNZCCRQIRWGPR-UHFFFAOYSA-N 0.000 description 1
- WJYXFUVYAHAONU-UHFFFAOYSA-N 5-cyclohexylidene-1-ethoxy-1,1-diphenylpentan-2-amine hydrochloride Chemical compound Cl.C1(=CC=CC=C1)C(C(CCC=C1CCCCC1)N)(OCC)C1=CC=CC=C1 WJYXFUVYAHAONU-UHFFFAOYSA-N 0.000 description 1
- CMXKOLMJVIWSIR-UHFFFAOYSA-N C(C=CC(=O)O)(=O)O.C(CC)NC Chemical compound C(C=CC(=O)O)(=O)O.C(CC)NC CMXKOLMJVIWSIR-UHFFFAOYSA-N 0.000 description 1
- RNIPNFWUZMBJSV-UHFFFAOYSA-N Cl.C1(=CC=CC=C1)C(C(CCC=C1CCCCC1)(C)N)(OC)C1=CC=CC=C1 Chemical compound Cl.C1(=CC=CC=C1)C(C(CCC=C1CCCCC1)(C)N)(OC)C1=CC=CC=C1 RNIPNFWUZMBJSV-UHFFFAOYSA-N 0.000 description 1
- OWVKORJFYVMHTL-UHFFFAOYSA-N Cl.C1(=CC=CC=C1)C(CNCCCCC1CCC1)(OC)C1=CC=CC=C1 Chemical compound Cl.C1(=CC=CC=C1)C(CNCCCCC1CCC1)(OC)C1=CC=CC=C1 OWVKORJFYVMHTL-UHFFFAOYSA-N 0.000 description 1
- PLWUKNBSCFWWBW-UHFFFAOYSA-N Cl.C=1C=CC=CC=1C(CCNCCC=CC)(OCC)C1=CC=CC=C1 Chemical compound Cl.C=1C=CC=CC=1C(CCNCCC=CC)(OCC)C1=CC=CC=C1 PLWUKNBSCFWWBW-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- BHNIKQDQYMOHIP-UHFFFAOYSA-N N-(3-methoxy-3,3-diphenylpropyl)cyclobutanecarboxamide Chemical compound C1(=CC=CC=C1)C(CCNC(=O)C1CCC1)(OC)C1=CC=CC=C1 BHNIKQDQYMOHIP-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QFSWEWNANAHUNE-UHFFFAOYSA-N alimadol Chemical compound C=1C=CC=CC=1C(CCNCC=C)(OC)C1=CC=CC=C1 QFSWEWNANAHUNE-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- JWOSTXBESVWMJW-UHFFFAOYSA-N cyclohexyl sulfamate Chemical compound NS(=O)(=O)OC1CCCCC1 JWOSTXBESVWMJW-UHFFFAOYSA-N 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- GVLGAFRNYJVHBC-UHFFFAOYSA-N hydrate;hydrobromide Chemical compound O.Br GVLGAFRNYJVHBC-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- MGCQZNBCJBRZDT-UHFFFAOYSA-N midodrine hydrochloride Chemical compound [H+].[Cl-].COC1=CC=C(OC)C(C(O)CNC(=O)CN)=C1 MGCQZNBCJBRZDT-UHFFFAOYSA-N 0.000 description 1
- XJSJQANHZLQJSC-UHFFFAOYSA-N n-(3-butoxy-3,3-diphenylpropyl)but-2-en-1-amine Chemical compound C=1C=CC=CC=1C(CCNCC=CC)(OCCCC)C1=CC=CC=C1 XJSJQANHZLQJSC-UHFFFAOYSA-N 0.000 description 1
- JTQVKRXONMISDA-UHFFFAOYSA-N n-(3-ethoxy-3,3-diphenylpropyl)but-2-en-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CCNCC=CC)(OCC)C1=CC=CC=C1 JTQVKRXONMISDA-UHFFFAOYSA-N 0.000 description 1
- YFRYFWQHDBSDRV-UHFFFAOYSA-N n-(3-methoxy-3,3-diphenylpropyl)but-2-en-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CCNCC=CC)(OC)C1=CC=CC=C1 YFRYFWQHDBSDRV-UHFFFAOYSA-N 0.000 description 1
- AHZQJDCOSNLSTF-UHFFFAOYSA-N n-but-2-enyl-3-ethoxy-2-methyl-3,3-diphenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(C(C)CNCC=CC)(OCC)C1=CC=CC=C1 AHZQJDCOSNLSTF-UHFFFAOYSA-N 0.000 description 1
- FLDJJZOWKFYOJU-UHFFFAOYSA-N n-but-2-enyl-3-methoxy-2-methyl-3,3-diphenylpropan-1-amine;hydrate;hydrochloride Chemical compound O.Cl.C=1C=CC=CC=1C(C(C)CNCC=CC)(OC)C1=CC=CC=C1 FLDJJZOWKFYOJU-UHFFFAOYSA-N 0.000 description 1
- QOWRDYNWUMKQJT-UHFFFAOYSA-N n-but-3-ynyl-3-methoxy-2-methyl-3,3-diphenylpropan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C(C)CNCCC#C)(OC)C1=CC=CC=C1 QOWRDYNWUMKQJT-UHFFFAOYSA-N 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/48—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT776572A AT320614B (de) | 1972-09-11 | 1972-09-11 | Verfahren zur Herstellung von neuen basischen Äthern und von deren Säureadditionssalzen |
| AT776572 | 1972-09-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI56825B FI56825B (fi) | 1979-12-31 |
| FI56825C true FI56825C (fi) | 1980-04-10 |
Family
ID=3599260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2048/73A FI56825C (fi) | 1972-09-11 | 1973-06-27 | Foerfarande foer framstaellning av nya analgetiska basiska etrar |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5229736B2 (de) |
| AT (1) | AT320614B (de) |
| CA (1) | CA986539A (de) |
| CH (1) | CH580567A5 (de) |
| CS (1) | CS164754B2 (de) |
| DD (1) | DD106032A1 (de) |
| ES (1) | ES416834A1 (de) |
| FI (1) | FI56825C (de) |
| HU (1) | HU165416B (de) |
| LU (1) | LU67864A1 (de) |
| PL (1) | PL84618B1 (de) |
| RO (1) | RO62912A (de) |
| SE (1) | SE398640B (de) |
| SU (1) | SU488399A3 (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5491200A (en) * | 1977-12-28 | 1979-07-19 | Noboru Nakamura | Safety system for house or like |
-
1972
- 1972-09-11 AT AT776572A patent/AT320614B/de not_active IP Right Cessation
-
1973
- 1973-06-21 CS CS4464A patent/CS164754B2/cs unknown
- 1973-06-22 LU LU67864A patent/LU67864A1/xx unknown
- 1973-06-27 FI FI2048/73A patent/FI56825C/fi active
- 1973-07-06 HU HUOE201A patent/HU165416B/hu unknown
- 1973-07-12 ES ES416834A patent/ES416834A1/es not_active Expired
- 1973-07-30 DD DD172607A patent/DD106032A1/xx unknown
- 1973-07-30 RO RO7300075653A patent/RO62912A/ro unknown
- 1973-07-31 JP JP48085550A patent/JPS5229736B2/ja not_active Expired
- 1973-07-31 SU SU1957933A patent/SU488399A3/ru active
- 1973-07-31 CH CH1117873A patent/CH580567A5/de not_active IP Right Cessation
- 1973-07-31 SE SE7310529A patent/SE398640B/xx unknown
- 1973-09-06 CA CA180422A patent/CA986539A/en not_active Expired
- 1973-09-11 PL PL1973165149A patent/PL84618B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE398640B (sv) | 1978-01-09 |
| RO62912A (fr) | 1977-12-15 |
| CS164754B2 (de) | 1975-11-28 |
| JPS5229736B2 (de) | 1977-08-03 |
| DD106032A1 (de) | 1974-05-20 |
| SU488399A3 (ru) | 1975-10-15 |
| JPS4980051A (de) | 1974-08-02 |
| CA986539A (en) | 1976-03-30 |
| HU165416B (de) | 1974-08-28 |
| FI56825B (fi) | 1979-12-31 |
| LU67864A1 (de) | 1973-08-30 |
| SE7310529L (de) | 1974-03-12 |
| PL84618B1 (en) | 1976-04-30 |
| ES416834A1 (es) | 1976-02-16 |
| AT320614B (de) | 1975-02-25 |
| CH580567A5 (en) | 1976-10-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69606915T2 (de) | Aryl(alkyl)propylamide, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen, die sie enthalten | |
| AU2006224853B2 (en) | Trifluoromethylbenzamide derivatives and therapeutic uses thereof | |
| DE69734773T2 (de) | Nicht-peptidische Bombesin-Rezeptor-Antagonisten | |
| NO155417B (no) | Anlegg for marin, seismisk undersoekelse. | |
| CA2541066C (fr) | Derives d'indanyl-piperazines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
| DE3877709T2 (de) | Indan-derivate und verfahren zu deren herstellung. | |
| PT93218B (pt) | Processo para a preparacao de 2-amino-1,2,3,4-tetra-idronaftalenos e 3-aminocromanos substituidos no anel | |
| JPH06505027A (ja) | グアニジン構造を有する新規化合物及びそれを含む医薬組成物 | |
| US4018830A (en) | Phenylthioaralkylamines | |
| FI56825C (fi) | Foerfarande foer framstaellning av nya analgetiska basiska etrar | |
| RU1776257C (ru) | Способ получени ацилоксипропаноламинов | |
| NO124430B (de) | ||
| US2838509A (en) | 9-aminoalkyl-9-xanthenecarboxamides | |
| US2625567A (en) | 1-benzyloxy-2-alkylaminoindanes | |
| US3320247A (en) | Phenthiazine compounds | |
| CA2143249C (fr) | Nouvelles sulfonamides substituees, leur procede de preparation et les compositions pharmaceutiques les renfermant | |
| US2940992A (en) | 2, 2-diphenyl-3-thiolpropionic acid and derivatives thereof | |
| DE69713128T2 (de) | 4-(1-piperazinyl)benzosäurederivate, verfahren zu ihrer herstellung und ihre therapeutischen verwendungen | |
| US2520178A (en) | 2, 3-diaryl-4-thiazolidones and their preparation | |
| DAHLBOM et al. | Esters and Amides of 2, 6-Dimethyl-and 2, 4, 6-Trimethylphenylcarbamic Acid | |
| US2822391A (en) | Conhj | |
| JP2010505807A (ja) | Ｎｐ−１アンタゴニスト活性を有するアルギニン誘導体 | |
| RU2547096C2 (ru) | N-[2-(адамант-2-ил)аминокарбонилметил]-n'-(диалкиламино)алкилнитробензамиды, обладающие антиаритмической активностью | |
| CH365379A (de) | Verfahren zur Herstellung von neuen, in 3-Stellung mit einer einwertigen Schwefelfunktion substituierten Phenothiazinen | |
| NO123720B (de) |