CZ281817B6 - N-Alkyl-3-fenyl-3-(2-alkylthiofenoxy)propylamin způsob jeho přípravy a farmaceutický prostředek který ho obsahuje - Google Patents

N-Alkyl-3-fenyl-3-(2-alkylthiofenoxy)propylamin způsob jeho přípravy a farmaceutický prostředek který ho obsahuje Download PDF

Info

Publication number: CZ281817B6
Authority: CZ; Czechia
Prior art keywords: phenyl; alkyl; formula; alkylthiophenoxy; propylamine
Prior art date: 1991-09-27

Application number

CS922908A

Other languages

Czech (cs)

English (en)

Inventor

Donald Richard Gehlert

David Wayne Robertson

David Taiwai Wong

Original Assignee

Eli Lilly And Company

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1991-09-27

Filing date

1992-09-22

Publication date

1997-02-12

1992-09-22 Application filed by Eli Lilly And Company filed Critical Eli Lilly And Company

1993-04-14 Publication of CZ290892A3 publication Critical patent/CZ290892A3/cs

1997-02-12 Publication of CZ281817B6 publication Critical patent/CZ281817B6/cs

Links

WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 title claims description 15
238000000034 method Methods 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 6
230000008569 process Effects 0.000 title claims description 5
239000000825 pharmaceutical preparation Substances 0.000 title 1
150000001875 compounds Chemical group 0.000 claims description 40
150000003839 salts Chemical class 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 15
239000008194 pharmaceutical composition Substances 0.000 claims description 13
150000001412 amines Chemical class 0.000 claims description 7
230000012154 norepinephrine uptake Effects 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 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
125000006239 protecting group Chemical group 0.000 claims description 4
230000002485 urinary effect Effects 0.000 claims description 4
208000032841 Bulimia Diseases 0.000 claims description 3
206010006550 Bulimia nervosa Diseases 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 3
239000003112 inhibitor Substances 0.000 claims description 3
LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical compound NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
238000005576 amination reaction Methods 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
208000020401 Depressive disease Diseases 0.000 claims 2
125000005843 halogen group Chemical group 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
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229960002748 norepinephrine Drugs 0.000 abstract description 16
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 abstract description 15
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 abstract description 15
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
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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
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238000009825 accumulation Methods 0.000 description 2
239000012267 brine Substances 0.000 description 2
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
201000010099 disease Diseases 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
239000008103 glucose Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-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
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239000011734 sodium Substances 0.000 description 2
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
230000005062 synaptic transmission Effects 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
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-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
AXCPQHPNAZONTH-UHFFFAOYSA-N 2-chloro-1-phenylpropan-1-one Chemical compound CC(Cl)C(=O)C1=CC=CC=C1 AXCPQHPNAZONTH-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
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XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
235000011180 diphosphates Nutrition 0.000 description 1
108700006189 dopamine beta hydroxylase deficiency Proteins 0.000 description 1
208000009308 dopamine beta-hydroxylase deficiency Diseases 0.000 description 1
238000009509 drug development Methods 0.000 description 1
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239000000706 filtrate Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
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239000012458 free base Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
229940014259 gelatin Drugs 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940079826 hydrogen sulfite Drugs 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
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239000008101 lactose Substances 0.000 description 1
239000010410 layer Substances 0.000 description 1
238000012417 linear regression Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000005567 liquid scintillation counting Methods 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000005341 metaphosphate group Chemical group 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
IZYBEMGNIUSSAX-UHFFFAOYSA-N methyl benzenecarboperoxoate Chemical compound COOC(=O)C1=CC=CC=C1 IZYBEMGNIUSSAX-UHFFFAOYSA-N 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
201000003631 narcolepsy Diseases 0.000 description 1
ITJNARMNRKSWTA-UHFFFAOYSA-N nisoxetine Chemical compound C=1C=CC=CC=1C(CCNC)OC1=CC=CC=C1OC ITJNARMNRKSWTA-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
229950009215 phenylbutanoic acid Drugs 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000003518 presynaptic effect Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical class CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
230000003938 response to stress Effects 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
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
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
239000012058 sterile packaged powder Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
235000011044 succinic acid Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid group Chemical group C(CCC(=O)O)(=O)O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
210000003568 synaptosome Anatomy 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
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
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229940071104 xylenesulfonate Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/48—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing rings
- 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
- C07C323/23—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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
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- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- 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
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
- 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)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
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Veterinary Medicine (AREA)
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Animal Behavior & Ethology (AREA)
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Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Biomedical Technology (AREA)
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Neurosurgery (AREA)
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Urology & Nephrology (AREA)
Endocrinology (AREA)
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Addiction (AREA)
Pain & Pain Management (AREA)
Toxicology (AREA)
Reproductive Health (AREA)
Hospice & Palliative Care (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)

CS922908A 1991-09-27 1992-09-22 N-Alkyl-3-fenyl-3-(2-alkylthiofenoxy)propylamin způsob jeho přípravy a farmaceutický prostředek který ho obsahuje CZ281817B6 (cs)

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 (2)

Publication Number	Publication Date
CZ290892A3 CZ290892A3 (en)	1993-04-14
CZ281817B6 true CZ281817B6 (cs)	1997-02-12

Family

ID=25078150

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS922908A CZ281817B6 (cs)	1991-09-27	1992-09-22	N-Alkyl-3-fenyl-3-(2-alkylthiofenoxy)propylamin způsob jeho přípravy a farmaceutický prostředek který ho obsahuje

Country Status (23)

Country	Link
US (1)	US5281624A (2)
EP (1)	EP0534756A3 (2)
JP (2)	JP3256291B2 (2)
KR (1)	KR100221180B1 (2)
CN (1)	CN1033580C (2)
AT (1)	ATE124934T1 (2)
AU (1)	AU655075B2 (2)
BR (2)	BR9203743A (2)
CA (2)	CA2079162A1 (2)
CZ (1)	CZ281817B6 (2)
DE (1)	DE69203424T2 (2)
FI (1)	FI111250B (2)
HU (1)	HU215519B (2)
IL (1)	IL103277A (2)
MX (1)	MX9205433A (2)
MY (1)	MY108304A (2)
NO (1)	NO178109C (2)
NZ (1)	NZ244460A (2)
RU (1)	RU2057120C1 (2)
SK (1)	SK290892A3 (2)
TW (1)	TW249225B (2)
YU (1)	YU87192A (2)
ZA (1)	ZA927240B (2)

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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
TW344661B (en) *	1993-11-24	1998-11-11	Lilly Co Eli	Pharmaceutical composition for treatment of incontinence
NZ313076A (en) *	1995-07-24	1999-11-29	Lilly Co Eli	Medicament containing duloxetine for treating hyperactivity and attention deficiency disorders
JP2001502302A (ja) *	1996-09-19	2001-02-20	アメリカン・ホーム・プロダクツ・コーポレイション	尿失禁を治療する方法
IL138855A0 (en) *	1998-04-09	2001-10-31	Upjohn Co	New treatments for nervous disorders
US6586427B2 (en)	1998-04-09	2003-07-01	Pharmacia & Upjohn Company	Treatments for nervous disorders
US6342533B1 (en)	1998-12-01	2002-01-29	Sepracor, Inc.	Derivatives of (−)-venlafaxine and methods of preparing and using the same
DE60039132D1 (de) *	1999-04-06	2008-07-17	Sepracor Inc	O-Desmethylvenlafaxin-Succinat
CN1164574C (zh) *	1999-05-24	2004-09-01	三菱制药株式会社	苯氧基丙胺类化合物
US6465458B1 (en) *	1999-07-01	2002-10-15	Pharmacia & Upjohn Company	Method of treating or preventing chronic pain with a highly selective norepinephrine reuptake inhibitor
US20040034106A1 (en) *	2001-11-06	2004-02-19	Read Holly Ann	Treatment of anxiety disorders
DE60220825T2 (de) *	2001-11-30	2008-03-06	Eli Lilly And Co., Indianapolis	Verwendung von norepinephrinwiederaufnahmehemmern zur behandlung von ticks
BR0213581A (pt) *	2001-12-11	2004-08-24	Lilly Co Eli	Uso de um inibidor de recaptação de norepinefrina seletivo
EP1539181B1 (en) *	2003-04-04	2007-06-27	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
EP1729754B1 (en) *	2003-12-12	2008-07-02	Eli Lilly And Company	Selective norepinephrine reuptake inhibitors for the treatment of hot flashes
ITMI20061987A1 (it)	2006-10-16	2008-04-17	Archimica Srl	Processo per la sintesi di arilossipropilammine ed eteroarilossipropilammine.
JP2020536941A (ja) *	2017-10-16	2020-12-17	エステベファーマシューティカルズ, ソシエダッドアノニマEsteve Pharmaceuticals, S.A.	疼痛及び疼痛に関連する状態を治療するためのプロパンアミン誘導体
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

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US4018895A (en) *	1974-01-10	1977-04-19	Eli Lilly And Company	Aryloxyphenylpropylamines in treating depression
US4626549A (en) *	1974-01-10	1986-12-02	Eli Lilly And Company	Treatment of obesity with aryloxyphenylpropylamines
US4314081A (en) *	1974-01-10	1982-02-02	Eli Lilly And Company	Arloxyphenylpropylamines
US4584404A (en) *	1974-01-10	1986-04-22	Eli Lilly And Company	Substituted phenoxyphenylproply dimethylamines
US4313896A (en) *	1974-01-10	1982-02-02	Eli Lilly And Company	Aryloxyphenylpropylamines
US4194009A (en) *	1974-01-10	1980-03-18	Eli Lilly And Company	Aryloxyphenylpropylamines for obtaining a psychotropic effect
CA1337128C (en) *	1988-04-08	1995-09-26	David Wayne Robertson	Propanamine derivatives

1991
- 1991-09-27 US US07/766,993 patent/US5281624A/en not_active Expired - Lifetime
1992
- 1992-09-22 ZA ZA927240A patent/ZA927240B/xx unknown
- 1992-09-22 SK SK2908-92A patent/SK290892A3/sk unknown
- 1992-09-22 CZ CS922908A patent/CZ281817B6/cs not_active IP Right Cessation
- 1992-09-23 NZ NZ244460A patent/NZ244460A/en unknown
- 1992-09-23 MY MYPI92001704A patent/MY108304A/en unknown
- 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 DE DE69203424T patent/DE69203424T2/de not_active Expired - Fee Related
- 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 HU HU9203051A patent/HU215519B/hu not_active IP Right Cessation
- 1992-09-24 AT AT92308709T patent/ATE124934T1/de not_active IP Right Cessation
- 1992-09-25 AU AU25370/92A patent/AU655075B2/en not_active Ceased
- 1992-09-25 RU SU5052706/04A patent/RU2057120C1/ru not_active IP Right Cessation
- 1992-09-25 JP JP25632792A patent/JP3256291B2/ja not_active Expired - Fee Related
- 1992-09-25 FI FI924305A patent/FI111250B/fi active
- 1992-09-25 BR BR929203743A patent/BR9203743A/pt not_active Application Discontinuation
- 1992-09-25 CA CA002079162A patent/CA2079162A1/en not_active Abandoned
- 1992-09-25 YU YU87192A patent/YU87192A/sh unknown
- 1992-09-25 CA CA002079161A patent/CA2079161C/en not_active Expired - Fee Related
- 1992-09-25 KR KR1019920017511A patent/KR100221180B1/ko not_active Expired - Fee Related
- 1992-09-25 JP JP4256333A patent/JPH05238996A/ja not_active Withdrawn
- 1992-09-26 CN CN92111081A patent/CN1033580C/zh not_active Expired - Fee Related
- 1992-11-10 TW TW081108988A patent/TW249225B/zh active
1997
- 1997-04-30 BR BR1100384-7A patent/BR1100384A/pt active IP Right Grant

Also Published As

Publication number	Publication date
HUT65375A (en)	1994-05-02
HU215519B (hu)	1999-01-28
AU2537092A (en)	1993-04-01
NZ244460A (en)	1994-10-26
DE69203424D1 (de)	1995-08-17
MY108304A (en)	1996-09-30
FI924305A0 (fi)	1992-09-25
RU2057120C1 (ru)	1996-03-27
DE69203424T2 (de)	1996-01-11
FI924305L (fi)	1993-03-28
AU655075B2 (en)	1994-12-01
HU9203051D0 (en)	1992-12-28
YU87192A (sh)	1995-10-24
EP0534756A2 (en)	1993-03-31
KR100221180B1 (ko)	1999-09-15
IL103277A (en)	1997-11-20
NO923710D0 (no)	1992-09-24
FI111250B (fi)	2003-06-30
NO923710L (no)	1993-03-29
JPH05238996A (ja)	1993-09-17
KR930005972A (ko)	1993-04-20
MX9205433A (es)	1993-03-01
SK280480B6 (sk)	2000-02-14
TW249225B (2)	1995-06-11
SK290892A3 (en)	2000-02-14
CN1033580C (zh)	1996-12-18
CA2079161A1 (en)	1993-03-28
JP3256291B2 (ja)	2002-02-12
ZA927240B (en)	1994-03-22
IL103277A0 (en)	1993-02-21
CA2079161C (en)	2004-02-17
EP0534756A3 (en)	1993-06-16
CZ290892A3 (en)	1993-04-14
BR1100384A (pt)	1999-08-31
US5281624A (en)	1994-01-25
BR9203743A (pt)	1993-04-20
JPH05201961A (ja)	1993-08-10
CN1071416A (zh)	1993-04-28
ATE124934T1 (de)	1995-07-15
NO178109B (no)	1995-10-16
NO178109C (no)	1996-01-24
CA2079162A1 (en)	1993-03-28

Legal Events

Date	Code	Title	Description
2000-06-30	IF00	In force as of 2000-06-30 in czech republic
2004-06-16	MM4A	Patent lapsed due to non-payment of fee	Effective date: 20030922

Publication	Publication Date	Title
CZ281817B6 (cs)	1997-02-12	N-Alkyl-3-fenyl-3-(2-alkylthiofenoxy)propylamin způsob jeho přípravy a farmaceutický prostředek který ho obsahuje
CS227019B2 (en)	1984-04-16	Method of preparing (-)-n-methyl-3-(2-methylphenyloxy)-3-phenylpropylamine
US4313896A (en)	1982-02-02	Aryloxyphenylpropylamines
EP0288188A1 (en)	1988-10-26	1-Phenyl-3-naphthalenyloxy-propanamines
JPH0348679A (ja)	1991-03-01	テトラゾール系興奮性アミノ酸受容体アンタゴニスト
EP0369685B1 (en)	1995-04-19	Fluoxetine analog
KR20160126988A (ko)	2016-11-02	아미노카보닐카바메이트 화합물
US20110092578A1 (en)	2011-04-21	Broad Spectrum Gram-Positive Antimicrobials and Anthelmintics with Efficacy Against Drug-Resistant Strains and Mycobacterium Species
RU2001911C1 (ru)	1993-10-30	Способ получени замещенных 1,2,3,4-тетрагидронафталинов или их фармацевтически приемлемых аддитивных солей кислоты
EP0537915B1 (en)	1995-07-12	N-alkyl-3-phenyl-3-(2-alkylthiophenoxy)propylamines as norepinephrine inhibitors
DE60010758T2 (de)	2005-05-12	Piperidin-derivate und ihre verwendung als serotonin rezeptor antagonisten
DE69828522T2 (de)	2005-12-15	Antithrombotische mittel
EP0591581B1 (en)	1995-08-09	N-Alkyl-3-phenyl-3-(2-alkylthiophenoxy)propylamines
CA1336287C (en)	1995-07-11	Selective serotonin uptake inhibitors
DE69619156T2 (de)	2002-08-14	Verwendung von alpha-Aminomethyl-3,4-dichlorbenzylthioaceamiden zur Herstellung eines dopaminwiederergreifungshemmenden Medikaments sowie Verbindungen zur Verwendung derselben