FI68807C - Foerfarande foer framstaellning av nya som depressionslaekemedel anvaendbara trans-4-fenyl-1,2,3,4-tetrahydro-1-naftalenaminderivat - Google Patents
Foerfarande foer framstaellning av nya som depressionslaekemedel anvaendbara trans-4-fenyl-1,2,3,4-tetrahydro-1-naftalenaminderivat Download PDFInfo
- Publication number
- FI68807C FI68807C FI803399A FI803399A FI68807C FI 68807 C FI68807 C FI 68807C FI 803399 A FI803399 A FI 803399A FI 803399 A FI803399 A FI 803399A FI 68807 C FI68807 C FI 68807C
- Authority
- FI
- Finland
- Prior art keywords
- trans
- formula
- tetrahydro
- hydrogen
- acid
- Prior art date
Links
- 230000005540 biological transmission Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 75
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 46
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 239000000935 antidepressant agent Substances 0.000 claims description 11
- 229940005513 antidepressants Drugs 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000003377 acid catalyst Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- BLFQGGGGFNSJKA-LWHGMNCYSA-N (1r,4s)-4-(3,4-dichlorophenyl)-n-methyl-1,2,3,4-tetrahydronaphthalen-1-amine;hydrochloride Chemical compound Cl.C1([C@@H]2CC[C@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 BLFQGGGGFNSJKA-LWHGMNCYSA-N 0.000 claims description 2
- IWNWWVPLTTUPBQ-XJKSGUPXSA-N (1r,4s)-4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1([C@@H]2CC[C@H](C3=CC=CC=C32)N)=CC=CC=C1 IWNWWVPLTTUPBQ-XJKSGUPXSA-N 0.000 claims description 2
- 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 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 102000007530 Neurofibromin 1 Human genes 0.000 claims 1
- 108010085793 Neurofibromin 1 Proteins 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 78
- 239000000243 solution Substances 0.000 description 62
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- 229910052799 carbon Inorganic materials 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 28
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 22
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 22
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000000921 elemental analysis Methods 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 16
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 15
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 15
- 229960002748 norepinephrine Drugs 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 239000002585 base Substances 0.000 description 13
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical class C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 11
- 229940076279 serotonin Drugs 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 230000004700 cellular uptake Effects 0.000 description 9
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229960003638 dopamine Drugs 0.000 description 8
- -1 for example Chemical class 0.000 description 8
- 239000012458 free base Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- 239000012259 ether extract Substances 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 6
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000012965 benzophenone Substances 0.000 description 6
- 150000008366 benzophenones Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 5
- 238000011534 incubation Methods 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000000538 analytical sample Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 150000003840 hydrochlorides Chemical class 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- 230000003518 presynaptic effect Effects 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- VGKDLMBJGBXTGI-YVEFUNNKSA-N (1r,4s)-4-(3,4-dichlorophenyl)-n-methyl-1,2,3,4-tetrahydronaphthalen-1-amine Chemical group C1([C@@H]2CC[C@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-YVEFUNNKSA-N 0.000 description 3
- 229940000681 5-hydroxytryptophan Drugs 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 206010044565 Tremor Diseases 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000006286 aqueous extract Substances 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- 239000002024 ethyl acetate extract Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000012286 potassium permanganate Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 210000000225 synapse Anatomy 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- LLUPHTAYNHAVQT-UHFFFAOYSA-N (3,4-dichlorophenyl)-phenylmethanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)C1=CC=CC=C1 LLUPHTAYNHAVQT-UHFFFAOYSA-N 0.000 description 2
- KEOLYBMGRQYQTN-UHFFFAOYSA-N (4-bromophenyl)-phenylmethanone Chemical compound C1=CC(Br)=CC=C1C(=O)C1=CC=CC=C1 KEOLYBMGRQYQTN-UHFFFAOYSA-N 0.000 description 2
- OGTSHGYHILFRHD-UHFFFAOYSA-N (4-fluorophenyl)-phenylmethanone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=CC=C1 OGTSHGYHILFRHD-UHFFFAOYSA-N 0.000 description 2
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 2
- KITYLYRCUBYTCO-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3,4-dihydro-2h-naphthalen-1-ol Chemical compound C1=CC(OC)=CC=C1C1(O)C2=CC=CC=C2CCC1 KITYLYRCUBYTCO-UHFFFAOYSA-N 0.000 description 2
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-dichlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 description 2
- DVKZCJSFZWEOFW-UHFFFAOYSA-N 4-(4-methoxyphenyl)-n-methyl-1,2-dihydronaphthalen-1-amine;hydrochloride Chemical compound Cl.C12=CC=CC=C2C(NC)CC=C1C1=CC=C(OC)C=C1 DVKZCJSFZWEOFW-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- UGVRJVHOJNYEHR-UHFFFAOYSA-N 4-chlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 UGVRJVHOJNYEHR-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- IWNWWVPLTTUPBQ-UHFFFAOYSA-N 4-phenyl-1,2,3,4-tetrahydronaphthalen-1-amine Chemical class C12=CC=CC=C2C(N)CCC1C1=CC=CC=C1 IWNWWVPLTTUPBQ-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 210000001653 corpus striatum Anatomy 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000009837 dry grinding Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- OHTYZZYAMUVKQS-UHFFFAOYSA-N phenyl-[4-(trifluoromethyl)phenyl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)C1=CC=CC=C1 OHTYZZYAMUVKQS-UHFFFAOYSA-N 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 230000001242 postsynaptic effect Effects 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- OPNWBQBGQDRXPF-LRHAYUFXSA-N (1R)-4-(4-fluoro-3-methoxyphenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound CN[C@@H]1CCC(C2=CC=CC=C12)C1=CC(=C(C=C1)F)OC OPNWBQBGQDRXPF-LRHAYUFXSA-N 0.000 description 1
- BLFQGGGGFNSJKA-UQICWFIISA-N (1r)-4-(3,4-dichlorophenyl)-n-methyl-1,2,3,4-tetrahydronaphthalen-1-amine;hydrochloride Chemical compound Cl.C([C@H](C1=CC=CC=C11)NC)CC1C1=CC=C(Cl)C(Cl)=C1 BLFQGGGGFNSJKA-UQICWFIISA-N 0.000 description 1
- JEFAHXOMQYOJGI-JZABEEBUSA-N (1r)-7-chloro-4-(4-chlorophenyl)-n-methyl-1,2,3,4-tetrahydronaphthalen-1-amine;hydrochloride Chemical compound Cl.C([C@H](C1=CC(Cl)=CC=C11)NC)CC1C1=CC=C(Cl)C=C1 JEFAHXOMQYOJGI-JZABEEBUSA-N 0.000 description 1
- LTKRQOGLVNJKBK-SCLBCKFNSA-N (1r,4s)-4-(3,4-dichlorophenyl)-n,n-dimethyl-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1([C@@H]2CC[C@H](C3=CC=CC=C32)N(C)C)=CC=C(Cl)C(Cl)=C1 LTKRQOGLVNJKBK-SCLBCKFNSA-N 0.000 description 1
- WYYWGFVKGGHRTH-MAUKXSAKSA-N (1r,4s)-4-(4-chlorophenyl)-7-methoxy-n-methyl-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1([C@@H]2CC[C@H](C3=CC(OC)=CC=C32)NC)=CC=C(Cl)C=C1 WYYWGFVKGGHRTH-MAUKXSAKSA-N 0.000 description 1
- VBGHDLDPLPNLTB-MAUKXSAKSA-N (1r,4s)-4-(4-chlorophenyl)-n,n-dimethyl-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1([C@@H]2CC[C@H](C3=CC=CC=C32)N(C)C)=CC=C(Cl)C=C1 VBGHDLDPLPNLTB-MAUKXSAKSA-N 0.000 description 1
- QTILPEMKUQBCMU-SQQLFYIASA-N (1r,4s)-4-(4-chlorophenyl)-n-methyl-1,2,3,4-tetrahydronaphthalen-1-amine;hydrochloride Chemical compound Cl.C1([C@@H]2CC[C@H](C3=CC=CC=C32)NC)=CC=C(Cl)C=C1 QTILPEMKUQBCMU-SQQLFYIASA-N 0.000 description 1
- BCOIWMLSVSGXIH-WMLDXEAASA-N (1r,4s)-7-chloro-4-(4-chlorophenyl)-n-methyl-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1([C@@H]2CC[C@H](C3=CC(Cl)=CC=C32)NC)=CC=C(Cl)C=C1 BCOIWMLSVSGXIH-WMLDXEAASA-N 0.000 description 1
- MKSRSZKGUKRVLK-MAUKXSAKSA-N (1r,4s)-n,n-dimethyl-4-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1([C@@H]2CC[C@H](C3=CC=CC=C32)N(C)C)=CC=CC(C(F)(F)F)=C1 MKSRSZKGUKRVLK-MAUKXSAKSA-N 0.000 description 1
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- BLFQGGGGFNSJKA-KELGLJHESA-N (1s,4r)-4-(3,4-dichlorophenyl)-n-methyl-1,2,3,4-tetrahydronaphthalen-1-amine;hydrochloride Chemical compound Cl.C1([C@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 BLFQGGGGFNSJKA-KELGLJHESA-N 0.000 description 1
- FRGRVQZKRCFTHR-CVLQQERVSA-N (1s,4r)-4-(4-bromophenyl)-n-methyl-1,2,3,4-tetrahydronaphthalen-1-amine;hydrochloride Chemical compound Cl.C1([C@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Br)C=C1 FRGRVQZKRCFTHR-CVLQQERVSA-N 0.000 description 1
- VLTYTTRXESKBKI-UHFFFAOYSA-N (2,4-dichlorophenyl)-phenylmethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 VLTYTTRXESKBKI-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
- JRZGPXSSNPTNMA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-amine Chemical class C1=CC=C2C(N)CCCC2=C1 JRZGPXSSNPTNMA-UHFFFAOYSA-N 0.000 description 1
- DETWFIUAXSWCIK-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-ylazanium;chloride Chemical compound [Cl-].C1=CC=C2C([NH3+])CCCC2=C1 DETWFIUAXSWCIK-UHFFFAOYSA-N 0.000 description 1
- FLKBAJVLMSWHDI-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-3,4-dihydro-2h-naphthalen-1-amine;hydrochloride Chemical compound Cl.C1CCC2=CC=CC=C2C1(N)C1=CC=C(Cl)C(Cl)=C1 FLKBAJVLMSWHDI-UHFFFAOYSA-N 0.000 description 1
- KBEGDFHMVUHUBZ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-4-(methylamino)-3,4-dihydro-2h-naphthalen-1-ol Chemical compound C12=CC=CC=C2C(NC)CCC1(O)C1=CC=C(OC)C=C1 KBEGDFHMVUHUBZ-UHFFFAOYSA-N 0.000 description 1
- HTDQSWDEWGSAMN-UHFFFAOYSA-N 1-bromo-2-methoxybenzene Chemical compound COC1=CC=CC=C1Br HTDQSWDEWGSAMN-UHFFFAOYSA-N 0.000 description 1
- PLDWAJLZAAHOGG-UHFFFAOYSA-N 1-bromo-3-methoxybenzene Chemical compound COC1=CC=CC(Br)=C1 PLDWAJLZAAHOGG-UHFFFAOYSA-N 0.000 description 1
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- KWVPFECTOKLOBL-KTKRTIGZSA-N 2-[(z)-octadec-9-enoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCO KWVPFECTOKLOBL-KTKRTIGZSA-N 0.000 description 1
- RZPFVRFSYMUDJO-UHFFFAOYSA-N 2h-naphthalen-1-one Chemical compound C1=CC=C2C(=O)CC=CC2=C1 RZPFVRFSYMUDJO-UHFFFAOYSA-N 0.000 description 1
- VTXNOVCTHUBABW-UHFFFAOYSA-N 3,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C(Cl)=C1 VTXNOVCTHUBABW-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
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- WMRZQZSHORKWBP-UHFFFAOYSA-N 3-ethoxycarbonyl-4-(4-fluorophenyl)-4-phenylbut-3-enoic acid Chemical compound C=1C=C(F)C=CC=1C(=C(CC(O)=O)C(=O)OCC)C1=CC=CC=C1 WMRZQZSHORKWBP-UHFFFAOYSA-N 0.000 description 1
- CCUBHTFLNYYIES-UHFFFAOYSA-N 4,4-bis(4-chlorophenyl)butanoic acid Chemical compound C=1C=C(Cl)C=CC=1C(CCC(=O)O)C1=CC=C(Cl)C=C1 CCUBHTFLNYYIES-UHFFFAOYSA-N 0.000 description 1
- JGMBHJNMQVKDMW-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=C(Cl)C(Cl)=CC=C1C1C2=CC=CC=C2C(=O)CC1 JGMBHJNMQVKDMW-UHFFFAOYSA-N 0.000 description 1
- IOQHRBSCAXDTNE-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-3-ethoxycarbonyl-4-phenylbut-3-enoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(=C(CC(O)=O)C(=O)OCC)C1=CC=CC=C1 IOQHRBSCAXDTNE-UHFFFAOYSA-N 0.000 description 1
- ZBLZQVJTLMFDCG-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-4-phenylbutanoic acid Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(CCC(=O)O)C1=CC=CC=C1 ZBLZQVJTLMFDCG-UHFFFAOYSA-N 0.000 description 1
- OIEBOOCWMVDAJZ-UHFFFAOYSA-N 4-(4-bromophenyl)-4-phenylbut-3-enoic acid Chemical compound C=1C=C(Br)C=CC=1C(=CCC(=O)O)C1=CC=CC=C1 OIEBOOCWMVDAJZ-UHFFFAOYSA-N 0.000 description 1
- ZEIGNLYJYUTFQX-UHFFFAOYSA-N 4-(4-bromophenyl)-4-phenylbutanoic acid Chemical compound C=1C=C(Br)C=CC=1C(CCC(=O)O)C1=CC=CC=C1 ZEIGNLYJYUTFQX-UHFFFAOYSA-N 0.000 description 1
- ZGTVFDARSVHBEF-UHFFFAOYSA-N 4-(4-fluorophenyl)-4-phenylbutanoic acid Chemical compound C=1C=C(F)C=CC=1C(CCC(=O)O)C1=CC=CC=C1 ZGTVFDARSVHBEF-UHFFFAOYSA-N 0.000 description 1
- FHRXAVHXIKEWEU-UHFFFAOYSA-N 4-(4-methoxyphenyl)-1,2-dihydronaphthalene Chemical compound C1=CC(OC)=CC=C1C1=CCCC2=CC=CC=C12 FHRXAVHXIKEWEU-UHFFFAOYSA-N 0.000 description 1
- SEVMQEIGENUPIE-UHFFFAOYSA-N 4-bromo-1-fluoro-2-methoxybenzene Chemical compound COC1=CC(Br)=CC=C1F SEVMQEIGENUPIE-UHFFFAOYSA-N 0.000 description 1
- DWNXGZBXFDNKOR-UHFFFAOYSA-N 4-bromo-2-fluoro-1-methoxybenzene Chemical compound COC1=CC=C(Br)C=C1F DWNXGZBXFDNKOR-UHFFFAOYSA-N 0.000 description 1
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 1
- BGPJTIXJFAGUIF-UHFFFAOYSA-N 4-hydroxy-3,4-dihydro-2h-naphthalen-1-one Chemical class C1=CC=C2C(O)CCC(=O)C2=C1 BGPJTIXJFAGUIF-UHFFFAOYSA-N 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- MNALUTYMBUBKNX-UHFFFAOYSA-N 6-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(OC)=CC=C21 MNALUTYMBUBKNX-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ASCDFTARWARIRO-UHFFFAOYSA-N C(C)OC(=O)C(CC(=O)O)=C(C1=CC=CC=C1)C1=CC=C(C=C1)F.FC1=CC=C(C=C1)C(=CCC(=O)O)C1=CC=CC=C1 Chemical compound C(C)OC(=O)C(CC(=O)O)=C(C1=CC=CC=C1)C1=CC=C(C=C1)F.FC1=CC=C(C=C1)C(=CCC(=O)O)C1=CC=CC=C1 ASCDFTARWARIRO-UHFFFAOYSA-N 0.000 description 1
- RJZLSQZVJWZOOP-HITUICJYSA-N C(\C=C/C(=O)O)(=O)O.CN([C@@H]1CCC(C2=CC=CC=C12)C1=CC(=CC=C1)C(F)(F)F)C Chemical compound C(\C=C/C(=O)O)(=O)O.CN([C@@H]1CCC(C2=CC=CC=C12)C1=CC(=CC=C1)C(F)(F)F)C RJZLSQZVJWZOOP-HITUICJYSA-N 0.000 description 1
- IJFLPRXTTDNJGB-LRHAYUFXSA-N CN[C@@H]1CCC(C2=CC=CC=C12)C3=CC(=C(C=C3)OC)F Chemical compound CN[C@@H]1CCC(C2=CC=CC=C12)C3=CC(=C(C=C3)OC)F IJFLPRXTTDNJGB-LRHAYUFXSA-N 0.000 description 1
- LHUZBYTXHMVIOD-WMLDXEAASA-N CN[C@@H]1CC[C@H](C2=CCCC=C12)C3=CC=C(C=C3)Cl Chemical compound CN[C@@H]1CC[C@H](C2=CCCC=C12)C3=CC=C(C=C3)Cl LHUZBYTXHMVIOD-WMLDXEAASA-N 0.000 description 1
- BXVNBGUBGOCDKI-UHFFFAOYSA-N COC1=CC=C(C=C1)C1=CCCC2=CC=CC=C12.COC1=CC=C(C=C1)C1CCCC2=CC=CC=C12 Chemical compound COC1=CC=C(C=C1)C1=CCCC2=CC=CC=C12.COC1=CC=C(C=C1)C1CCCC2=CC=CC=C12 BXVNBGUBGOCDKI-UHFFFAOYSA-N 0.000 description 1
- QPTSMILUIBRERI-UHFFFAOYSA-N COC1=CC=C(C=C1)C1CCCC2=CC=CC=C12.OC1(CCC(C2=CC=CC=C12)=O)C1=CC=C(C=C1)OC Chemical compound COC1=CC=C(C=C1)C1CCCC2=CC=CC=C12.OC1(CCC(C2=CC=CC=C12)=O)C1=CC=C(C=C1)OC QPTSMILUIBRERI-UHFFFAOYSA-N 0.000 description 1
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 description 1
- DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical class OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 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
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-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
- 239000007818 Grignard reagent Substances 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 102000010909 Monoamine Oxidase Human genes 0.000 description 1
- 108010062431 Monoamine oxidase Proteins 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001398 anti-anorexic effect Effects 0.000 description 1
- 230000002022 anti-cellular effect Effects 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 208000013404 behavioral symptom Diseases 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000008359 benzonitriles Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004958 brain cell Anatomy 0.000 description 1
- 150000004648 butanoic acid derivatives Chemical class 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- QVDYYQXUNAQSNI-UHFFFAOYSA-N ethyl acetate;pentane Chemical compound CCCCC.CCOC(C)=O QVDYYQXUNAQSNI-UHFFFAOYSA-N 0.000 description 1
- CJOFXWAVKWHTFT-XSFVSMFZSA-N fluvoxamine Chemical compound COCCCC\C(=N/OCCN)C1=CC=C(C(F)(F)F)C=C1 CJOFXWAVKWHTFT-XSFVSMFZSA-N 0.000 description 1
- 229960004038 fluvoxamine Drugs 0.000 description 1
- 239000010200 folin Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000002267 hypothalamic effect Effects 0.000 description 1
- 210000003016 hypothalamus Anatomy 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- XPLZAZCGEUUFJL-UHFFFAOYSA-N n-benzyl-3-[2-(pyridine-4-carbonyl)hydrazinyl]propanamide;hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C[NH2+]C(=O)CCNNC(=O)C1=CC=NC=C1 XPLZAZCGEUUFJL-UHFFFAOYSA-N 0.000 description 1
- IWNASFAWDLBFQQ-UHFFFAOYSA-N n-methyl-4-[3-(trifluoromethyl)phenyl]-3,4-dihydro-2h-naphthalen-1-imine Chemical compound C12=CC=CC=C2C(=NC)CCC1C1=CC=CC(C(F)(F)F)=C1 IWNASFAWDLBFQQ-UHFFFAOYSA-N 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000008183 oral pharmaceutical preparation Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- IOXDAYKKVHAKSX-UHFFFAOYSA-N phenyl-[3-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 IOXDAYKKVHAKSX-UHFFFAOYSA-N 0.000 description 1
- 229950009215 phenylbutanoic acid Drugs 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002731 protein assay Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 230000018405 transmission of nerve impulse Effects 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/30—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system formed by two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
- C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
- C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9023779A | 1979-11-01 | 1979-11-01 | |
| US9023779 | 1979-11-01 | ||
| US18444780 | 1980-09-05 | ||
| US06/184,447 US4556676A (en) | 1979-11-01 | 1980-09-05 | Antidepressant derivatives of trans-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI803399L FI803399L (fi) | 1981-05-02 |
| FI68807B FI68807B (fi) | 1985-07-31 |
| FI68807C true FI68807C (fi) | 1985-11-11 |
Family
ID=26782055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI803399A FI68807C (fi) | 1979-11-01 | 1980-10-30 | Foerfarande foer framstaellning av nya som depressionslaekemedel anvaendbara trans-4-fenyl-1,2,3,4-tetrahydro-1-naftalenaminderivat |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4556676A (el) |
| EP (1) | EP0028901B1 (el) |
| KR (1) | KR840002021B1 (el) |
| AR (2) | AR225196A1 (el) |
| AT (1) | ATE2667T1 (el) |
| AU (1) | AU517842B2 (el) |
| CA (1) | CA1130816A (el) |
| DE (1) | DE3062226D1 (el) |
| DK (1) | DK149308C (el) |
| ES (2) | ES8201948A1 (el) |
| FI (1) | FI68807C (el) |
| GR (1) | GR70782B (el) |
| IE (1) | IE50396B1 (el) |
| IL (1) | IL61376A (el) |
| NO (1) | NO149102C (el) |
| PH (1) | PH15468A (el) |
| PT (1) | PT72005B (el) |
| YU (2) | YU41744B (el) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE8004002L (sv) * | 1980-05-29 | 1981-11-30 | Arvidsson Folke Lars Erik | Terapeutiskt anvendbara tetralinderivat |
| US4866208A (en) * | 1981-12-21 | 1989-09-12 | The Dow Chemical Company | Meta-phenylene diamine derivatives |
| US4777288A (en) * | 1987-06-11 | 1988-10-11 | Pfizer Inc. | Process for preparing a 4,4-diphenylbutanoic acid derivative |
| US4839104A (en) * | 1987-06-11 | 1989-06-13 | Pfizer, Inc. | Process for preparing sertraline intermediates |
| FR2623802B1 (fr) * | 1987-11-26 | 1990-05-04 | Lucien Laboratoires | Derives d'amino-4 trifluoromethyl-1 tetralines. leur preparation et leur application en therapeutique |
| FR2642065B1 (fr) * | 1989-01-24 | 1991-05-24 | Lipha | Derives d'acides benzocycloalcenyl dihydroxy alcanoiques, procede de preparation et medicaments les contenant |
| FR2665443B1 (fr) * | 1990-08-03 | 1992-11-06 | Lucien Laboratoires | Derives d'amino-4-methyl-1-tetralines, leur preparation et leur application en therapeutique. |
| US5082970A (en) * | 1991-03-06 | 1992-01-21 | Pfizer Inc. | Process for recycling amine isomer |
| GB9114948D0 (en) * | 1991-07-11 | 1991-08-28 | Pfizer Ltd | Process for preparing sertraline intermediates |
| US5196607A (en) * | 1992-02-14 | 1993-03-23 | Pfizer Inc. | Process for preparing ketone enantiomer |
| US5248699A (en) * | 1992-08-13 | 1993-09-28 | Pfizer Inc. | Sertraline polymorph |
| US5466880A (en) * | 1992-09-15 | 1995-11-14 | Pfizer Inc. | Process for preparing ketone enantiomer |
| EP0697894A4 (en) * | 1993-03-31 | 1996-05-01 | Univ Pennsylvania | DOPAMINE D-3 AND SEROTONIN (5-HT 1A) RECEPTOR LIGANDS AND IMAGING AGENTS |
| DK0724552T3 (da) * | 1993-11-30 | 1997-12-22 | Pfizer | Fremgangsmåde til fremstilling af chiralt tetralon |
| US6410794B1 (en) | 1994-12-16 | 2002-06-25 | Uop Llc | Process for preparation of pharmaceutically desired chiral tetralone from tetralones |
| US6455736B1 (en) | 1994-12-16 | 2002-09-24 | Uop Llc | Process for preparation of pharmaceutically desired sertraline and sertraline analogs |
| HU222341B1 (hu) * | 1996-12-18 | 2003-06-28 | Richter Gedeon Vegyészeti Gyár Rt. | Eljárás sertralin előállítására és az eljárásban alkalmazott intermedier |
| IN182588B (el) | 1998-05-12 | 1999-05-08 | Sun Pharmaceutical Ind Ltd | |
| IN187170B (el) | 2000-01-04 | 2002-02-23 | Sun Pharmaceutical Ind Ltd | |
| DE10006411C2 (de) * | 2000-02-14 | 2002-03-07 | Huf Huelsbeck & Fuerst Gmbh | Elektronischer Zündanlaßschalter für Kraftfahrzeuge und Reserveschlüssel zur Betätigung desselben |
| DE10041478A1 (de) | 2000-08-24 | 2002-03-14 | Sanol Arznei Schwarz Gmbh | Neue pharmazeutische Zusammensetzung |
| US6482440B2 (en) | 2000-09-21 | 2002-11-19 | Phase 2 Discovery, Inc. | Long acting antidepressant microparticles |
| US6723878B2 (en) | 2001-06-15 | 2004-04-20 | Orion Corporation Fermion | Method for preparing sertraline |
| JP2006504693A (ja) * | 2002-09-16 | 2006-02-09 | セプラコア インコーポレーテッド | トランス４−（３，４−ジクロロフェニル）−１，２，３，４−テトラヒドロ−ｎ−メチル−１−ナフタレンアミンによるｃｎｓ障害の治療 |
| US7087785B2 (en) * | 2002-09-16 | 2006-08-08 | Sepracor Inc. | Treatment of CNS disorders with trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine and its formamide |
| US8134029B2 (en) | 2002-09-16 | 2012-03-13 | Sunovion Pharmaceuticals Inc. | Treatment of CNS disorders with trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine |
| DE10334187A1 (de) * | 2003-07-26 | 2005-03-03 | Schwarz Pharma Ag | Substituierte 2-Aminotetraline zur Behandlung von Depressionen |
| DE10334188B4 (de) * | 2003-07-26 | 2007-07-05 | Schwarz Pharma Ag | Verwendung von Rotigotin zur Behandlung von Depressionen |
| US20060014838A1 (en) * | 2004-07-14 | 2006-01-19 | Sudhakar Valluri | Process for converting trans-sertraline to cis-sertraline |
| JP2009500425A (ja) | 2005-07-06 | 2009-01-08 | セプラコア インコーポレーテッド | エスゾピクロン及びトランス４−（３，４−ジクロロフェニル）−１，２，３，４−テトラヒドロ−ｎ−メチル−１−ナフタレンアミン又はトランス４−（３，４−ジクロロフェニル）−１，２，３，４−テトラヒドロ−１−ナフタレンアミンの組み合わせ、並びに閉経期並びに気分、不安、及び認知障害の治療方法 |
| DK2013835T3 (en) * | 2006-03-31 | 2015-12-14 | Sunovion Pharmaceuticals Inc | Preparation of chiral amides and AMINES |
| KR20090015089A (ko) * | 2006-05-31 | 2009-02-11 | 세프라코 아이엔시. | 트랜스 4-(3,4-디클로로페닐)-1,2,3,4-테트라하이드로-1-나프탈렌아민 및 그의 포름아미드에 의한 통증장애 치료방법 |
| US20100279990A1 (en) * | 2006-06-13 | 2010-11-04 | Ramot At Tel-Aviv University Ltd. | Antiproliferative compounds, compositions and methods of use |
| EP1987815A1 (en) * | 2007-05-04 | 2008-11-05 | Schwarz Pharma Ag | Oronasopharyngeally deliverable pharmaceutical compositions of dopamine agonists for the prevention and/or treatment of restless limb disorders |
| US20100081713A1 (en) * | 2008-03-19 | 2010-04-01 | CombinatoRx, (Singapore) Pte. Ltd. | Compositions and methods for treating viral infections |
| WO2015175514A1 (en) * | 2014-05-13 | 2015-11-19 | Sunovion Pharmaceuticals Inc. | Methods and compositions of dasotraline for treatment of adhd |
| WO2015175523A1 (en) * | 2014-05-13 | 2015-11-19 | Sunovion Pharmaceuticals Inc. | Dosage of dasotraline and method for treatment of adhd |
| WO2016046669A2 (en) * | 2014-09-27 | 2016-03-31 | Mohan M Alapati | Compositions and methods for the treatment of depression and neurological diseases |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB793853A (en) * | 1954-09-15 | 1958-04-23 | Schering Ag | Manufacture of new 3-amino-indanes |
| DE1098511B (de) * | 1959-11-21 | 1961-02-02 | Schering Ag | Verfahren zur Abtrennung von analgetisch wirksamen d-1-Phenyl-3-dimethylaminoindan |
| US3704323A (en) * | 1969-12-23 | 1972-11-28 | Squibb & Sons Inc | Indane derivatives |
| GB1420472A (en) * | 1972-09-27 | 1976-01-07 | Pfizer | Aminophenyltetralin compounds |
| US4029731A (en) * | 1974-11-06 | 1977-06-14 | Pfizer Inc. | Aminophenyltetralin compounds |
| US4045488A (en) * | 1974-11-06 | 1977-08-30 | Pfizer Inc. | Aminophenyltetralin compounds |
-
1980
- 1980-09-05 US US06/184,447 patent/US4556676A/en not_active Expired - Lifetime
- 1980-10-28 DE DE8080303810T patent/DE3062226D1/de not_active Expired
- 1980-10-28 AT AT80303810T patent/ATE2667T1/de not_active IP Right Cessation
- 1980-10-28 EP EP80303810A patent/EP0028901B1/en not_active Expired
- 1980-10-29 PH PH24786A patent/PH15468A/en unknown
- 1980-10-30 FI FI803399A patent/FI68807C/fi not_active IP Right Cessation
- 1980-10-30 CA CA363,571A patent/CA1130816A/en not_active Expired
- 1980-10-30 YU YU2774/80A patent/YU41744B/xx unknown
- 1980-10-30 IL IL61376A patent/IL61376A/xx unknown
- 1980-10-30 AR AR283061A patent/AR225196A1/es active
- 1980-10-30 GR GR63248A patent/GR70782B/el unknown
- 1980-10-31 DK DK462480A patent/DK149308C/da not_active IP Right Cessation
- 1980-10-31 NO NO803259A patent/NO149102C/no unknown
- 1980-10-31 IE IE2260/80A patent/IE50396B1/en not_active IP Right Cessation
- 1980-10-31 KR KR1019800004175A patent/KR840002021B1/ko active
- 1980-10-31 ES ES496441A patent/ES8201948A1/es not_active Expired
- 1980-10-31 AU AU63898/80A patent/AU517842B2/en not_active Expired
- 1980-10-31 PT PT72005A patent/PT72005B/pt unknown
-
1981
- 1981-10-06 AR AR286998A patent/AR229106A1/es active
- 1981-11-05 ES ES506893A patent/ES506893A0/es active Granted
-
1983
- 1983-01-07 YU YU33/83A patent/YU42066B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR225196A1 (es) | 1982-02-26 |
| ES8207120A1 (es) | 1982-09-01 |
| FI68807B (fi) | 1985-07-31 |
| YU3383A (en) | 1983-09-30 |
| YU41744B (en) | 1987-12-31 |
| ES496441A0 (es) | 1982-01-16 |
| AU6389880A (en) | 1981-05-07 |
| DK149308B (da) | 1986-04-28 |
| DK462480A (da) | 1981-05-02 |
| FI803399L (fi) | 1981-05-02 |
| EP0028901A1 (en) | 1981-05-20 |
| IE50396B1 (en) | 1986-04-16 |
| KR840002021B1 (ko) | 1984-11-05 |
| NO803259L (no) | 1981-05-04 |
| NO149102B (no) | 1983-11-07 |
| DK149308C (da) | 1986-12-08 |
| ATE2667T1 (de) | 1983-03-15 |
| EP0028901B1 (en) | 1983-03-02 |
| YU277480A (en) | 1983-09-30 |
| IL61376A0 (en) | 1980-12-31 |
| YU42066B (en) | 1988-04-30 |
| ES506893A0 (es) | 1982-09-01 |
| GR70782B (el) | 1983-03-23 |
| US4556676A (en) | 1985-12-03 |
| AU517842B2 (en) | 1981-08-27 |
| NO149102C (no) | 1984-02-15 |
| CA1130816A (en) | 1982-08-31 |
| IL61376A (en) | 1983-10-31 |
| DE3062226D1 (en) | 1983-04-07 |
| AR229106A1 (es) | 1983-06-15 |
| PT72005A (en) | 1980-11-01 |
| PT72005B (en) | 1981-08-31 |
| IE802260L (en) | 1981-05-01 |
| PH15468A (en) | 1983-01-24 |
| ES8201948A1 (es) | 1982-01-16 |
| KR830004201A (ko) | 1983-07-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI68807C (fi) | Foerfarande foer framstaellning av nya som depressionslaekemedel anvaendbara trans-4-fenyl-1,2,3,4-tetrahydro-1-naftalenaminderivat | |
| FI68806C (fi) | Foerfarande foer framstaellning av nya cis-4-fenyl-1,2,3,4-tetrahydro-1-naftalenderivat anvaendbara som depressionslaekemedel | |
| Welch et al. | Nontricyclic antidepressant agents derived from cis-and trans-1-amino-4-aryltetralins | |
| US7105699B2 (en) | Treatment of CNS disorders with trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine and its formamide | |
| US6048876A (en) | Medicament for the alleviation or treatment of symptom derived from ischemic disease and compound useful therefor | |
| US3637740A (en) | Aminobenzocycloalkane compounds | |
| US4876284A (en) | 1-alkyl-2-aminotetralin derivatives | |
| WO2007081542A9 (en) | Tetralone-based monoamine reuptake inhibitors | |
| EP0012643B1 (fr) | Dérivés de la phényl-1 (pipéridyl-4)-3 propanone-1, procédés pour leur préparation, et médicaments les contenant | |
| US10328036B2 (en) | Treatment of CNS disorders with trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine | |
| RU2232753C2 (ru) | 4-замещенные пиперидины, фармацевтическая композиция на их основе и способ лечения заболеваний центральной нервной системы | |
| JPS59497B2 (ja) | トランス−４−フエニル−１，２，３，４−テトラヒドロ−１−ナフタレンアミンの抗抑うつ性誘導体 | |
| US4719219A (en) | Phenyl-azacycloalkanes and use thereof in treatment of central nervous system disorders | |
| EP0293351B1 (en) | New aralkyl esters and processes for their preparation | |
| US4937346A (en) | Phenyl-azacykloalkanes | |
| PL129248B1 (en) | Method of preparation of novel cis isomer derivatives of 4-phenyl-1,2,3,4-tetrahydro-1-naphtaleneamine | |
| NO133664B (el) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired |
Owner name: PFIZER INC. |