NZ244460A - N-(methyl or ethyl)-3-phenyl-3-(2-alkylthiophenoxy)propylamines and medicaments - Google Patents
N-(methyl or ethyl)-3-phenyl-3-(2-alkylthiophenoxy)propylamines and medicamentsInfo
- Publication number
- NZ244460A NZ244460A NZ244460A NZ24446092A NZ244460A NZ 244460 A NZ244460 A NZ 244460A NZ 244460 A NZ244460 A NZ 244460A NZ 24446092 A NZ24446092 A NZ 24446092A NZ 244460 A NZ244460 A NZ 244460A
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- formula
- phenyl
- acid addition
- pharmaceutically acceptable
- Prior art date
Links
- 125000006308 propyl amino group Chemical group 0.000 title abstract description 3
- 239000003814 drug Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 229920002472 Starch Polymers 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 235000019698 starch Nutrition 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 239000008107 starch Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- 125000001475 halogen functional group Chemical group 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 235000019359 magnesium stearate Nutrition 0.000 claims description 4
- IUTPYKBKYDVRDB-UHFFFAOYSA-N n-methyl-3-(2-methylphenyl)sulfanyl-3-phenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(CCNC)SC1=CC=CC=C1C IUTPYKBKYDVRDB-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- 235000010980 cellulose Nutrition 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 239000007903 gelatin capsule Substances 0.000 claims description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000000454 talc Substances 0.000 claims description 3
- 229910052623 talc Inorganic materials 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 238000005576 amination reaction Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 235000012222 talc Nutrition 0.000 claims description 2
- 238000005303 weighing Methods 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims 1
- 239000008108 microcrystalline cellulose Substances 0.000 claims 1
- 229940016286 microcrystalline cellulose Drugs 0.000 claims 1
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 abstract description 19
- 229960002748 norepinephrine Drugs 0.000 abstract description 19
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 abstract description 18
- 208000012902 Nervous system disease Diseases 0.000 abstract 1
- 208000025966 Neurological disease Diseases 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 210000002569 neuron Anatomy 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 241000124008 Mammalia Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229940093915 gynecological organic acid Drugs 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- -1 para-toluenesulfonic Chemical class 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 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
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 230000012154 norepinephrine uptake Effects 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 229930006000 Sucrose Natural products 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 230000005062 synaptic transmission Effects 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- DYKZDPNOXOTEHQ-UHFFFAOYSA-N 1-(3-chloro-1-phenylpropoxy)-2-methylsulfanylbenzene Chemical compound CSC1=CC=CC=C1OC(CCCl)C1=CC=CC=C1 DYKZDPNOXOTEHQ-UHFFFAOYSA-N 0.000 description 1
- HCSBTDBGTNZOAB-UHFFFAOYSA-N 2,3-dinitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O HCSBTDBGTNZOAB-UHFFFAOYSA-N 0.000 description 1
- LXUNZSDDXMPKLP-UHFFFAOYSA-N 2-Methylbenzenethiol Chemical compound CC1=CC=CC=C1S LXUNZSDDXMPKLP-UHFFFAOYSA-N 0.000 description 1
- JZFUHAGLMZWKTF-UHFFFAOYSA-N 3-chloro-1-phenylpropan-1-ol Chemical compound ClCCC(O)C1=CC=CC=C1 JZFUHAGLMZWKTF-UHFFFAOYSA-N 0.000 description 1
- KTJRGPZVSKWRTJ-UHFFFAOYSA-N 3-chloro-1-phenylpropan-1-one Chemical compound ClCCC(=O)C1=CC=CC=C1 KTJRGPZVSKWRTJ-UHFFFAOYSA-N 0.000 description 1
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
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- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
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- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 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 1
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- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
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- VZIYNJNIJMZLNZ-UHFFFAOYSA-N N-methyl-3-(2-methylphenyl)sulfanyl-3-phenylpropan-1-amine hydrochloride Chemical compound Cl.CNCCC(SC1=C(C=CC=C1)C)C1=CC=CC=C1 VZIYNJNIJMZLNZ-UHFFFAOYSA-N 0.000 description 1
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- 238000001085 differential centrifugation Methods 0.000 description 1
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- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
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- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/29—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
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- 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
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
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- A61P39/02—Antidotes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Toxicology (AREA)
- Epidemiology (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)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/766,993 US5281624A (en) | 1991-09-27 | 1991-09-27 | N-alkyl-3-phenyl-3-(2-substituted phenoxy) propylamines and pharmaceutical use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ244460A true NZ244460A (en) | 1994-10-26 |
Family
ID=25078150
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ244460A NZ244460A (en) | 1991-09-27 | 1992-09-23 | N-(methyl or ethyl)-3-phenyl-3-(2-alkylthiophenoxy)propylamines and medicaments |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US5281624A (en, 2012) |
| EP (1) | EP0534756A3 (en, 2012) |
| JP (2) | JPH05238996A (en, 2012) |
| KR (1) | KR100221180B1 (en, 2012) |
| CN (1) | CN1033580C (en, 2012) |
| AT (1) | ATE124934T1 (en, 2012) |
| AU (1) | AU655075B2 (en, 2012) |
| BR (2) | BR9203743A (en, 2012) |
| CA (2) | CA2079161C (en, 2012) |
| CZ (1) | CZ281817B6 (en, 2012) |
| DE (1) | DE69203424T2 (en, 2012) |
| FI (1) | FI111250B (en, 2012) |
| HU (1) | HU215519B (en, 2012) |
| IL (1) | IL103277A (en, 2012) |
| MX (1) | MX9205433A (en, 2012) |
| MY (1) | MY108304A (en, 2012) |
| NO (1) | NO178109C (en, 2012) |
| NZ (1) | NZ244460A (en, 2012) |
| RU (1) | RU2057120C1 (en, 2012) |
| SK (1) | SK290892A3 (en, 2012) |
| TW (1) | TW249225B (en, 2012) |
| YU (1) | YU87192A (en, 2012) |
| ZA (1) | ZA927240B (en, 2012) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7087765B2 (en) * | 1995-06-07 | 2006-08-08 | Nps Pharmaceuticals, Inc. | Compounds active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders and diseases |
| US6071970A (en) * | 1993-02-08 | 2000-06-06 | Nps Pharmaceuticals, Inc. | Compounds active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders and diseases |
| US6017965A (en) * | 1993-02-08 | 2000-01-25 | Nps Pharmaceuticals, Inc. | Compounds active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders and diseases |
| TW344661B (en) * | 1993-11-24 | 1998-11-11 | Lilly Co Eli | Pharmaceutical composition for treatment of incontinence |
| EA000856B1 (ru) * | 1995-07-24 | 2000-06-26 | Эли Лилли Энд Компани | Способ лечения синдрома дефицита внимания/гиперактивности |
| CA2266070A1 (en) * | 1996-09-19 | 1998-03-26 | American Home Products Corporation | Method of treating urinary incontinence |
| US6586427B2 (en) | 1998-04-09 | 2003-07-01 | Pharmacia & Upjohn Company | Treatments for nervous disorders |
| DE69926616T2 (de) * | 1998-04-09 | 2006-05-24 | Pharmacia & Upjohn Co. Llc, Kalamazoo | Verwendung von reboxetine zur behandlung neuropsychiatrischer beschwerden |
| US6342533B1 (en) | 1998-12-01 | 2002-01-29 | Sepracor, Inc. | Derivatives of (−)-venlafaxine and methods of preparing and using the same |
| EP1466889B1 (en) * | 1999-04-06 | 2008-06-04 | Sepracor Inc. | O-Desmethylvenlafaxine succinate |
| DE60022504T2 (de) | 1999-05-24 | 2006-06-29 | Mitsubishi Pharma Corp. | Phenoxypropylamin-derivate |
| DE60035232T2 (de) | 1999-07-01 | 2008-02-14 | Pharmacia & Upjohn Co. Llc, Kalamazoo | (S,S)-Reboxetin zur Behandlung von chronischem Müdigkeits-Syndrom |
| US20040034106A1 (en) * | 2001-11-06 | 2004-02-19 | Read Holly Ann | Treatment of anxiety disorders |
| PT1455770E (pt) * | 2001-11-30 | 2007-09-06 | Lilly Co Eli | Uso de inibidores de reabsorção da norepinefrina para o tratamento dos transtornos de tiques. |
| US20050009925A1 (en) * | 2001-12-11 | 2005-01-13 | Bymaster Franklin Porter | Use of norepinephrine reuptake inhibitors for the treatment of cognitive failure |
| US6846823B2 (en) * | 2003-04-04 | 2005-01-25 | Dynogen Pharmaceuticals, Inc. | Method of treating lower urinary tract disorders |
| CA2536161A1 (en) * | 2003-08-27 | 2005-03-10 | Eli Lilly And Company | Treatment of pervasive developmental disorders with norepinephrine reuptake inhibitors |
| JP2007513945A (ja) * | 2003-12-12 | 2007-05-31 | イーライ リリー アンド カンパニー | 体熱感、衝動調節障害および一般的な病状による人格変化の治療 |
| ITMI20061987A1 (it) * | 2006-10-16 | 2008-04-17 | Archimica Srl | Processo per la sintesi di arilossipropilammine ed eteroarilossipropilammine. |
| WO2019076904A1 (en) * | 2017-10-16 | 2019-04-25 | Esteve Pharmaceuticals, S.A. | PROPANAMINE DERIVATIVES FOR THE TREATMENT OF PAIN AND PAIN DISEASES ASSOCIATED WITH PAIN |
| CN113121394B (zh) * | 2019-12-30 | 2022-11-08 | 中国药科大学 | 一种苯氧乙酸类衍生物的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4194009A (en) * | 1974-01-10 | 1980-03-18 | Eli Lilly And Company | Aryloxyphenylpropylamines for obtaining a psychotropic effect |
| US4313896A (en) * | 1974-01-10 | 1982-02-02 | Eli Lilly And Company | Aryloxyphenylpropylamines |
| US4314081A (en) * | 1974-01-10 | 1982-02-02 | Eli Lilly And Company | Arloxyphenylpropylamines |
| US4018895A (en) * | 1974-01-10 | 1977-04-19 | Eli Lilly And Company | Aryloxyphenylpropylamines in treating depression |
| US4584404A (en) * | 1974-01-10 | 1986-04-22 | Eli Lilly And Company | Substituted phenoxyphenylproply dimethylamines |
| US4626549A (en) * | 1974-01-10 | 1986-12-02 | Eli Lilly And Company | Treatment of obesity with aryloxyphenylpropylamines |
| IL89854A (en) * | 1988-04-08 | 1994-02-27 | Lilly Co Eli | Phenoxypropanamines, the process for their preparation and medicinal preparations containing them |
-
1991
- 1991-09-27 US US07/766,993 patent/US5281624A/en not_active Expired - Lifetime
-
1992
- 1992-09-22 CZ CS922908A patent/CZ281817B6/cs not_active IP Right Cessation
- 1992-09-22 ZA ZA927240A patent/ZA927240B/xx unknown
- 1992-09-22 SK SK2908-92A patent/SK290892A3/sk unknown
- 1992-09-23 MY MYPI92001704A patent/MY108304A/en unknown
- 1992-09-23 NZ NZ244460A patent/NZ244460A/en unknown
- 1992-09-24 DE DE69203424T patent/DE69203424T2/de not_active Expired - Fee Related
- 1992-09-24 HU HU9203051A patent/HU215519B/hu not_active IP Right Cessation
- 1992-09-24 NO NO923710A patent/NO178109C/no unknown
- 1992-09-24 IL IL103277A patent/IL103277A/xx not_active IP Right Cessation
- 1992-09-24 MX MX9205433A patent/MX9205433A/es not_active IP Right Cessation
- 1992-09-24 EP EP19920308708 patent/EP0534756A3/en not_active Withdrawn
- 1992-09-24 AT AT92308709T patent/ATE124934T1/de not_active IP Right Cessation
- 1992-09-25 CA CA002079161A patent/CA2079161C/en not_active Expired - Fee Related
- 1992-09-25 FI FI924305A patent/FI111250B/fi active
- 1992-09-25 AU AU25370/92A patent/AU655075B2/en not_active Ceased
- 1992-09-25 KR KR1019920017511A patent/KR100221180B1/ko not_active Expired - Fee Related
- 1992-09-25 BR BR929203743A patent/BR9203743A/pt not_active Application Discontinuation
- 1992-09-25 YU YU87192A patent/YU87192A/sh unknown
- 1992-09-25 CA CA002079162A patent/CA2079162A1/en not_active Abandoned
- 1992-09-25 RU SU5052706/04A patent/RU2057120C1/ru not_active IP Right Cessation
- 1992-09-25 JP JP4256333A patent/JPH05238996A/ja not_active Withdrawn
- 1992-09-25 JP JP25632792A patent/JP3256291B2/ja not_active Expired - Fee Related
- 1992-09-26 CN CN92111081A patent/CN1033580C/zh not_active Expired - Fee Related
- 1992-11-10 TW TW081108988A patent/TW249225B/zh active
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1997
- 1997-04-30 BR BR1100384-7A patent/BR1100384A/pt active IP Right Grant
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