FI56826C - Foerfarande foer framstaellning av nya analgetiska basiska etrar - Google Patents
Foerfarande foer framstaellning av nya analgetiska basiska etrar Download PDFInfo
- Publication number
- FI56826C FI56826C FI2684/73A FI268473A FI56826C FI 56826 C FI56826 C FI 56826C FI 2684/73 A FI2684/73 A FI 2684/73A FI 268473 A FI268473 A FI 268473A FI 56826 C FI56826 C FI 56826C
- Authority
- FI
- Finland
- Prior art keywords
- diphenyl
- group
- hydrochloride
- methoxy
- methyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 20
- -1 p-methoxystyryl Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 230000000202 analgesic effect Effects 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000002170 ethers Chemical class 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 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
- 125000005504 styryl group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000002585 base Substances 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 14
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 230000008018 melting Effects 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 7
- 229960005181 morphine Drugs 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 5
- 150000002366 halogen compounds Chemical class 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- FDLVCUOMIAFXNG-UHFFFAOYSA-N methyl(propyl)azanium;chloride Chemical compound Cl.CCCNC FDLVCUOMIAFXNG-UHFFFAOYSA-N 0.000 description 4
- 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 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- WEBHVQDBZRLGAJ-UHFFFAOYSA-N 3-ethoxy-n-methyl-3,3-diphenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(CCNC)(OCC)C1=CC=CC=C1 WEBHVQDBZRLGAJ-UHFFFAOYSA-N 0.000 description 3
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- QFSWEWNANAHUNE-UHFFFAOYSA-N alimadol Chemical compound C=1C=CC=CC=1C(CCNCC=C)(OC)C1=CC=CC=C1 QFSWEWNANAHUNE-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 235000019788 craving Nutrition 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PNFIIZCTZSSUJX-UHFFFAOYSA-N 2,2,2-trifluoro-n-(3-methoxy-3,3-diphenylpropyl)acetamide Chemical compound C=1C=CC=CC=1C(CCNC(=O)C(F)(F)F)(OC)C1=CC=CC=C1 PNFIIZCTZSSUJX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 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
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 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
- 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
- YGDTXDIRMKZHHG-UHFFFAOYSA-N 1-methoxy-6-(4-methoxyphenyl)-1,1-diphenylhex-5-en-2-amine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C=CCCC(N)C(OC)(C=1C=CC=CC=1)C1=CC=CC=C1 YGDTXDIRMKZHHG-UHFFFAOYSA-N 0.000 description 1
- OXOKEWBHGSWFEW-UHFFFAOYSA-N 1-methoxy-n,2-dimethyl-1,1-diphenylhex-5-yn-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(OC)(C(C)(CCC#C)NC)C1=CC=CC=C1 OXOKEWBHGSWFEW-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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
- UVTMYYTWSHCUQX-UHFFFAOYSA-N 2-(cyclopropylmethyl)-1-methoxy-1,1,4-triphenylbutan-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C(N)(CCC=1C=CC=CC=1)CC1CC1)(OC)C1=CC=CC=C1 UVTMYYTWSHCUQX-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- LMVCALNFWYFFQS-UHFFFAOYSA-N 2-methyl-3,3-diphenyl-3-propoxypropan-1-amine Chemical compound C=1C=CC=CC=1C(C(C)CN)(OCCC)C1=CC=CC=C1 LMVCALNFWYFFQS-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
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- WMTBPAOXDXTIOV-UHFFFAOYSA-N 3-ethoxy-2-methyl-3,3-diphenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(C(C)CN)(OCC)C1=CC=CC=C1 WMTBPAOXDXTIOV-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
- NDEXJEOKBJQDNO-UHFFFAOYSA-N 3-ethoxy-3,3-diphenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(CCN)(OCC)C1=CC=CC=C1 NDEXJEOKBJQDNO-UHFFFAOYSA-N 0.000 description 1
- HGFNTGWVSIXNBP-UHFFFAOYSA-N 3-ethoxy-n,2-dimethyl-3,3-diphenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(C(C)CNC)(OCC)C1=CC=CC=C1 HGFNTGWVSIXNBP-UHFFFAOYSA-N 0.000 description 1
- MYGOUCWLYDRZAB-UHFFFAOYSA-N 3-methoxy-2-methyl-3,3-diphenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(C(C)CN)(OC)C1=CC=CC=C1 MYGOUCWLYDRZAB-UHFFFAOYSA-N 0.000 description 1
- HTUWRHWDXKHNSQ-UHFFFAOYSA-N 3-methoxy-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)(OC)CCNCC=CC1=CC=CC=C1 HTUWRHWDXKHNSQ-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
- ULJDDVBBLRHYBP-UHFFFAOYSA-N 3-methoxy-N-methyl-3,3-diphenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(OC)(CCNC)C1=CC=CC=C1 ULJDDVBBLRHYBP-UHFFFAOYSA-N 0.000 description 1
- HTJLJGLSBQBKBU-UHFFFAOYSA-N 3-methoxy-n,2-dimethyl-3,3-diphenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(OC)(C(C)CNC)C1=CC=CC=C1 HTJLJGLSBQBKBU-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
- GIGBSOWSBGIENJ-UHFFFAOYSA-N 4-cyclobutyl-1-methoxy-1,1-diphenylbutan-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC)C(N)CCC1CCC1 GIGBSOWSBGIENJ-UHFFFAOYSA-N 0.000 description 1
- KMIGAPNCAXNDDR-UHFFFAOYSA-N 4-cyclobutyl-1-methoxy-2-methyl-1,1-diphenylbutan-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C(C)(N)CCC1CCC1)(OC)C1=CC=CC=C1 KMIGAPNCAXNDDR-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
- AGSZKNGLWZWRAR-UHFFFAOYSA-N 4-cyclobutyl-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)CCC1CCC1 AGSZKNGLWZWRAR-UHFFFAOYSA-N 0.000 description 1
- CUFPQHCQVPMELF-UHFFFAOYSA-N 4-cyclopropyl-1,1-diphenyl-1-propoxybutan-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCCC)C(N)CCC1CC1 CUFPQHCQVPMELF-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
- TXLOUAHWLDJUPM-UHFFFAOYSA-N 4-cyclopropyl-1-ethoxy-n,2-dimethyl-1,1-diphenylbutan-2-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C(C)(CCC1CC1)NC)(OCC)C1=CC=CC=C1 TXLOUAHWLDJUPM-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
- 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 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
- OGSZHAKYARCHHH-UHFFFAOYSA-N 5-cyclohexylidene-1-ethoxy-2-methyl-1,1-diphenylpentan-2-amine Chemical compound C1(=CC=CC=C1)C(C(CCC=C1CCCCC1)(C)N)(OCC)C1=CC=CC=C1 OGSZHAKYARCHHH-UHFFFAOYSA-N 0.000 description 1
- INXOZYBLCSEGMP-UHFFFAOYSA-N 5-cyclohexylidene-1-methoxy-N,2-dimethyl-1,1-diphenylpentan-2-amine hydrochloride Chemical compound Cl.C1(=CC=CC=C1)C(C(CCC=C1CCCCC1)(C)NC)(OC)C1=CC=CC=C1 INXOZYBLCSEGMP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- KTSGMVRJIQWKEJ-UHFFFAOYSA-N C(C(O)C1=CC=CC=C1)(=O)O.C1(=CC=CC=C1)C(C(CCC=CC1=CC=CC=C1)(C)N)(OC)C1=CC=CC=C1 Chemical compound C(C(O)C1=CC=CC=C1)(=O)O.C1(=CC=CC=C1)C(C(CCC=CC1=CC=CC=C1)(C)N)(OC)C1=CC=CC=C1 KTSGMVRJIQWKEJ-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
- BQQQSVOFGBITEU-UHFFFAOYSA-N Cl.C=1C=CC=CC=1C(C(C)CNCCC=CC)(OC)C1=CC=CC=C1 Chemical compound Cl.C=1C=CC=CC=1C(C(C)CNCCC=CC)(OC)C1=CC=CC=C1 BQQQSVOFGBITEU-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
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 206010013663 drug dependence Diseases 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 125000005843 halogen group Chemical group 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
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 230000003340 mental effect Effects 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
- FQPAXPXVCOHIFV-UHFFFAOYSA-N n-benzyl-3-ethoxy-3,3-diphenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCC)CCNCC1=CC=CC=C1 FQPAXPXVCOHIFV-UHFFFAOYSA-N 0.000 description 1
- DAHOFCRMBFZKDA-UHFFFAOYSA-N n-benzyl-3-methoxy-3,3-diphenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC)CCNCC1=CC=CC=C1 DAHOFCRMBFZKDA-UHFFFAOYSA-N 0.000 description 1
- GOQFSAHGZNUWMQ-UHFFFAOYSA-N n-methyl-3,3-diphenyl-3-propoxypropan-1-amine Chemical compound C=1C=CC=CC=1C(CCNC)(OCCC)C1=CC=CC=C1 GOQFSAHGZNUWMQ-UHFFFAOYSA-N 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/62—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT776472A AT319916B (de) | 1972-09-11 | 1972-09-11 | Verfahren zur Herstellung von neuen basischen Äthern |
| AT776472 | 1972-09-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI56826B FI56826B (fi) | 1979-12-31 |
| FI56826C true FI56826C (fi) | 1980-04-10 |
Family
ID=3599253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2684/73A FI56826C (fi) | 1972-09-11 | 1973-08-29 | Foerfarande foer framstaellning av nya analgetiska basiska etrar |
Country Status (18)
-
1972
- 1972-09-11 AT AT776472A patent/AT319916B/de not_active IP Right Cessation
-
1973
- 1973-08-24 FR FR7330701A patent/FR2198740B1/fr not_active Expired
- 1973-08-27 LU LU68308A patent/LU68308A1/xx unknown
- 1973-08-29 FI FI2684/73A patent/FI56826C/fi active
- 1973-09-04 HU HUCE962A patent/HU166685B/hu unknown
- 1973-09-06 GB GB4206373A patent/GB1377350A/en not_active Expired
- 1973-09-06 CA CA180,396A patent/CA986138A/en not_active Expired
- 1973-09-10 PL PL1973165129A patent/PL86974B1/pl unknown
- 1973-09-10 CH CH835576A patent/CH590206A5/xx not_active IP Right Cessation
- 1973-09-10 ZA ZA737200*A patent/ZA737200B/xx unknown
- 1973-09-10 DD DD173374A patent/DD108521A1/xx unknown
- 1973-09-10 SE SE7312280A patent/SE413892B/xx unknown
- 1973-09-10 PL PL1973183330A patent/PL92115B1/pl unknown
- 1973-09-10 SU SU1957929A patent/SU495825A3/ru active
- 1973-09-10 BE BE135522A patent/BE804692A/xx unknown
- 1973-09-10 CH CH1294973A patent/CH596144A5/xx not_active IP Right Cessation
- 1973-09-11 RO RO7384229A patent/RO68417A/ro unknown
- 1973-09-11 CS CS736291A patent/CS203904B2/cs unknown
- 1973-09-11 ES ES418687A patent/ES418687A1/es not_active Expired
- 1973-09-11 RO RO7300076047A patent/RO63980A/ro unknown
- 1973-09-11 JP JP10176373A patent/JPS5320033B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5320033B2 (enrdf_load_stackoverflow) | 1978-06-24 |
| CH596144A5 (enrdf_load_stackoverflow) | 1978-02-28 |
| CS203904B2 (en) | 1981-03-31 |
| AT319916B (de) | 1975-01-10 |
| BE804692A (fr) | 1974-03-11 |
| JPS4962452A (enrdf_load_stackoverflow) | 1974-06-17 |
| RO68417A (ro) | 1981-09-24 |
| FI56826B (fi) | 1979-12-31 |
| SE413892B (sv) | 1980-06-30 |
| DD108521A1 (enrdf_load_stackoverflow) | 1974-09-20 |
| FR2198740B1 (enrdf_load_stackoverflow) | 1977-01-14 |
| PL92115B1 (en) | 1977-03-31 |
| AU6018473A (en) | 1975-03-13 |
| PL86974B1 (en) | 1976-06-30 |
| SU495825A3 (ru) | 1975-12-15 |
| RO63980A (fr) | 1978-08-15 |
| LU68308A1 (enrdf_load_stackoverflow) | 1973-11-23 |
| ZA737200B (en) | 1974-08-28 |
| CA986138A (en) | 1976-03-23 |
| HU166685B (enrdf_load_stackoverflow) | 1975-05-28 |
| GB1377350A (en) | 1974-12-11 |
| CH590206A5 (enrdf_load_stackoverflow) | 1977-07-29 |
| FR2198740A1 (enrdf_load_stackoverflow) | 1974-04-05 |
| ES418687A1 (es) | 1976-02-16 |
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