IL125146A - History - 3phenyl - 2 (methyl converted) Tropan, their preparation and pharmaceutical preparations containing them - Google Patents

History - 3phenyl - 2 (methyl converted) Tropan, their preparation and pharmaceutical preparations containing them

Info

Publication number: IL125146A
Authority: IL; Israel
Prior art keywords: tropane; dichlorophenyl; compound; nortropane; chlorophenyl
Prior art date: 1996-02-22

Application number

IL12514697A

Other languages

English (en)

Hebrew (he)

Other versions

IL125146A0 (en

Original Assignee

Neurosearch As

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.)

1996-02-22

Filing date

1997-02-21

Publication date

2002-03-10

1997-02-21 Application filed by Neurosearch As filed Critical Neurosearch As

1999-01-26 Publication of IL125146A0 publication Critical patent/IL125146A0/xx

2002-03-10 Publication of IL125146A publication Critical patent/IL125146A/en

Links

125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims abstract description 15
238000002360 preparation method Methods 0.000 title claims description 23
239000008194 pharmaceutical composition Substances 0.000 title claims description 12
150000003813 tropane derivatives Chemical class 0.000 title description 6
239000000203 mixture Substances 0.000 claims abstract description 54
229930004006 tropane Natural products 0.000 claims abstract description 35
-1 tropane compound Chemical class 0.000 claims abstract description 29
150000003839 salts Chemical class 0.000 claims abstract description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 10
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
239000001257 hydrogen Substances 0.000 claims abstract description 7
229910052736 halogen Inorganic materials 0.000 claims abstract description 5
150000002367 halogens Chemical group 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
125000001424 substituent group Chemical group 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
150000001875 compounds Chemical class 0.000 claims description 85
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
XLRPYZSEQKXZAA-OCAPTIKFSA-N tropane Chemical compound C1CC[C@H]2CC[C@@H]1N2C XLRPYZSEQKXZAA-OCAPTIKFSA-N 0.000 claims description 27
238000000034 method Methods 0.000 claims description 23
208000035475 disorder Diseases 0.000 claims description 18
230000005764 inhibitory process Effects 0.000 claims description 14
201000010099 disease Diseases 0.000 claims description 10
208000008589 Obesity Diseases 0.000 claims description 9
235000020824 obesity Nutrition 0.000 claims description 9
208000011117 substance-related disease Diseases 0.000 claims description 8
208000024827 Alzheimer disease Diseases 0.000 claims description 7
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
230000001561 neurotransmitter reuptake Effects 0.000 claims description 7
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 claims description 6
208000027089 Parkinsonian disease Diseases 0.000 claims description 6
206010034010 Parkinsonism Diseases 0.000 claims description 6
206010013663 drug dependence Diseases 0.000 claims description 6
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 5
206010039966 Senile dementia Diseases 0.000 claims description 5
201000003631 narcolepsy Diseases 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
230000007074 memory dysfunction Effects 0.000 claims description 4
241001465754 Metazoa Species 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
PGYDXVBZYKQYCS-VPWBDBDCSA-N (1s,3s,4r,5r)-3-(3,4-dichlorophenyl)-4-(methoxymethyl)-8-methyl-8-azabicyclo[3.2.1]octane Chemical compound C1([C@@H]2[C@@H](COC)[C@]3(CC[C@@](C2)(N3C)[H])[H])=CC=C(Cl)C(Cl)=C1 PGYDXVBZYKQYCS-VPWBDBDCSA-N 0.000 claims description 2
HTKSGXUNQZSQKB-VBRUCIBASA-N (1s,5r)-3-(3,4-dichlorophenyl)-4-(ethylsulfanylmethyl)-8-methyl-8-azabicyclo[3.2.1]octane Chemical compound CCSCC([C@]1(CC[C@@](C2)(N1C)[H])[H])C2C1=CC=C(Cl)C(Cl)=C1 HTKSGXUNQZSQKB-VBRUCIBASA-N 0.000 claims description 2
208000026097 Factitious disease Diseases 0.000 claims description 2
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IIUOULDVNOMXAP-ZJIFWQFVSA-N (1s,3s,4r,5r)-3-(4-chlorophenyl)-4-(methoxymethyl)-8-methyl-8-azabicyclo[3.2.1]octane Chemical compound C1([C@@H]2[C@@H](COC)[C@]3(CC[C@@](C2)(N3C)[H])[H])=CC=C(Cl)C=C1 IIUOULDVNOMXAP-ZJIFWQFVSA-N 0.000 claims 1
VCVWXKKWDOJNIT-VBRUCIBASA-N (1s,5r)-3-(3,4-dichlorophenyl)-4-(ethoxymethyl)-8-methyl-8-azabicyclo[3.2.1]octane Chemical compound CCOCC([C@]1(CC[C@@](C2)(N1C)[H])[H])C2C1=CC=C(Cl)C(Cl)=C1 VCVWXKKWDOJNIT-VBRUCIBASA-N 0.000 claims 1
PGYDXVBZYKQYCS-PIISCBOPSA-N (1s,5r)-3-(3,4-dichlorophenyl)-4-(methoxymethyl)-8-methyl-8-azabicyclo[3.2.1]octane Chemical compound COCC([C@]1(CC[C@@](C2)(N1C)[H])[H])C2C1=CC=C(Cl)C(Cl)=C1 PGYDXVBZYKQYCS-PIISCBOPSA-N 0.000 claims 1
IJIHFJXJGNXNBL-FAYHIZQSSA-N (1s,5r)-3-(3,4-dichlorophenyl)-8-methyl-4-(propan-2-yloxymethyl)-8-azabicyclo[3.2.1]octane Chemical compound CC(C)OCC([C@]1(CC[C@@](C2)(N1C)[H])[H])C2C1=CC=C(Cl)C(Cl)=C1 IJIHFJXJGNXNBL-FAYHIZQSSA-N 0.000 claims 1
IIUOULDVNOMXAP-SLTXQBBLSA-N (1s,5r)-3-(4-chlorophenyl)-4-(methoxymethyl)-8-methyl-8-azabicyclo[3.2.1]octane Chemical compound COCC([C@]1(CC[C@@](C2)(N1C)[H])[H])C2C1=CC=C(Cl)C=C1 IIUOULDVNOMXAP-SLTXQBBLSA-N 0.000 claims 1
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125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 abstract description 2
239000003901 neurotransmitter uptake inhibitor Substances 0.000 abstract 1
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
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239000000725 suspension Substances 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
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VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 12
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
239000007788 liquid Substances 0.000 description 9
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CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 8
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
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229910052943 magnesium sulfate Inorganic materials 0.000 description 8
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SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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108010044266 Dopamine Plasma Membrane Transport Proteins Proteins 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000872 buffer Substances 0.000 description 6
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SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 6
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230000001419 dependent effect Effects 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000028436 dopamine uptake Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
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238000003379 elimination reaction Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
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210000002615 epidermis Anatomy 0.000 description 1
230000001856 erectile effect Effects 0.000 description 1
KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229960002464 fluoxetine Drugs 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000003349 gelling agent Substances 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
230000000971 hippocampal effect Effects 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001793 isothiazol-3-yl group Chemical group [H]C1=C([H])C(*)=NS1 0.000 description 1
125000004500 isothiazol-4-yl group Chemical group S1N=CC(=C1)* 0.000 description 1
125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 description 1
125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 1
125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 description 1
125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
230000029849 luteinization Effects 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
208000024714 major depressive disease Diseases 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
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230000001404 mediated effect Effects 0.000 description 1
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LATFBQGSWGHBGW-JRJWNBDDSA-N methyl (1R,2R,3S,5S)-8-methyl-3-phenylmethoxy-8-azabicyclo[3.2.1]octane-2-carboxylate hydrochloride Chemical compound Cl.COC(=O)[C@@H]1[C@H]2CC[C@@H](C[C@@H]1OCc1ccccc1)N2C LATFBQGSWGHBGW-JRJWNBDDSA-N 0.000 description 1
RLLMNWXOZDXKCQ-KSUSIZLGSA-N methyl (1R,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate hydrochloride Chemical compound Cl.COC(=O)C1[C@H]2CC[C@@H](CC1O)N2C RLLMNWXOZDXKCQ-KSUSIZLGSA-N 0.000 description 1
ZEOHVQFWFVMPGM-ZQDZILKHSA-N methyl (1s,3r,4r,5s)-3-(4-chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate Chemical compound C1([C@H]2[C@H]([C@@]3(CC[C@@](C2)(N3C)[H])[H])C(=O)OC)=CC=C(Cl)C=C1 ZEOHVQFWFVMPGM-ZQDZILKHSA-N 0.000 description 1
ZEOHVQFWFVMPGM-AJNGGQMLSA-N methyl (1s,3r,4s,5s)-3-(4-chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate Chemical compound C1([C@H]2[C@@H]([C@@]3(CC[C@@](C2)(N3C)[H])[H])C(=O)OC)=CC=C(Cl)C=C1 ZEOHVQFWFVMPGM-AJNGGQMLSA-N 0.000 description 1
WXEMSGQRTGSYOG-PMDVUHRTSA-N methyl (1s,5r)-8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-4-carboxylate Chemical compound C1C(=O)C(C(=O)OC)[C@@]2([H])CC[C@]1([H])N2C WXEMSGQRTGSYOG-PMDVUHRTSA-N 0.000 description 1
WXEMSGQRTGSYOG-ASLNEKEESA-N methyl (1s,5s)-8-methyl-3-oxo-8-azabicyclo[3.2.1]octane-4-carboxylate Chemical compound C1C(=O)C(C(=O)OC)[C@]2([H])CC[C@]1([H])N2C WXEMSGQRTGSYOG-ASLNEKEESA-N 0.000 description 1
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230000000407 monoamine reuptake Effects 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
239000002324 mouth wash Substances 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-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
125000001624 naphthyl group Chemical group 0.000 description 1
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238000010899 nucleation Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 1
125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 description 1
125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 description 1
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238000007911 parenteral administration Methods 0.000 description 1
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229920001277 pectin Polymers 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
239000000825 pharmaceutical preparation Substances 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
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230000001242 postsynaptic effect Effects 0.000 description 1
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
229960002601 protriptyline Drugs 0.000 description 1
BWPIARFWQZKAIA-UHFFFAOYSA-N protriptyline Chemical compound C1=CC2=CC=CC=C2C(CCCNC)C2=CC=CC=C21 BWPIARFWQZKAIA-UHFFFAOYSA-N 0.000 description 1
239000013014 purified material Substances 0.000 description 1
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000004044 response Effects 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000000862 serotonergic effect Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
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239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
230000003019 stabilising effect Effects 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
230000005062 synaptic transmission Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
230000008719 thickening Effects 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
208000002271 trichotillomania Diseases 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
QUSLQENMLDRCTO-YJNKXOJESA-N win 35428 Chemical compound C1([C@H]2C[C@@H]3CC[C@@H](N3C)[C@H]2C(=O)OC)=CC=C(F)C=C1 QUSLQENMLDRCTO-YJNKXOJESA-N 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
- 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
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- 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
- A61P25/24—Antidepressants
- 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
- A61P25/28—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
- 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
- A61P25/36—Opioid-abuse
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Neurosurgery (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Psychiatry (AREA)
Addiction (AREA)
Pain & Pain Management (AREA)
Hematology (AREA)
Diabetes (AREA)
Child & Adolescent Psychology (AREA)
Obesity (AREA)
Hospice & Palliative Care (AREA)
Psychology (AREA)
Emergency Medicine (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL12514697A 1996-02-22 1997-02-21 History - 3phenyl - 2 (methyl converted) Tropan, their preparation and pharmaceutical preparations containing them IL125146A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DK19496		1996-02-22
PCT/EP1997/000850 WO1997030997A1 (fr)	1996-02-22	1997-02-21	Derives du tropane, leur preparation et utilisation

Publications (2)

Publication Number	Publication Date
IL125146A0 IL125146A0 (en)	1999-01-26
IL125146A true IL125146A (en)	2002-03-10

Family

ID=8090830

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12514697A IL125146A (en)	1996-02-22	1997-02-21	History - 3phenyl - 2 (methyl converted) Tropan, their preparation and pharmaceutical preparations containing them

Country Status (31)

Country	Link
US (3)	US6288079B1 (fr)
EP (2)	EP0885220B1 (fr)
JP (1)	JP3238414B2 (fr)
KR (1)	KR100446571B1 (fr)
CN (1)	CN1077574C (fr)
AT (1)	ATE203023T1 (fr)
AU (1)	AU720358B2 (fr)
BG (1)	BG63945B1 (fr)
BR (1)	BR9707636A (fr)
CA (1)	CA2244773C (fr)
CZ (1)	CZ287007B6 (fr)
DE (1)	DE69705608T2 (fr)
DK (1)	DK0885220T3 (fr)
EE (1)	EE04751B1 (fr)
ES (1)	ES2159839T3 (fr)
GR (1)	GR3036829T3 (fr)
HU (1)	HU228356B1 (fr)
IL (1)	IL125146A (fr)
IS (1)	IS1824B (fr)
NO (1)	NO318731B1 (fr)
NZ (1)	NZ330886A (fr)
PL (1)	PL185132B1 (fr)
PT (1)	PT885220E (fr)
RU (1)	RU2167876C2 (fr)
SG (1)	SG99853A1 (fr)
SI (1)	SI0885220T1 (fr)
SK (1)	SK281813B6 (fr)
TR (1)	TR199801641T2 (fr)
UA (1)	UA49872C2 (fr)
WO (1)	WO1997030997A1 (fr)
ZA (1)	ZA971525B (fr)

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Publication number	Priority date	Publication date	Assignee	Title
JP4386399B2 (ja) *	1998-09-30	2009-12-16	日本メジフィジックス株式会社	光学活性トロピノンモノカルボン酸エステル誘導体の製造法
AUPP627498A0 (en)	1998-10-02	1998-10-22	University Of Queensland, The	Novel peptides - i
JP2005508872A (ja) *	2001-05-23	2005-04-07	ニューロサーチ、アクティーゼルスカブ	トロパン誘導体及びこれをモノアミン神経伝達物質再取り込み阻害剤として使用する方法
CA2373559C (fr) *	2001-10-11	2010-07-27	Organix, Inc.	Inhibiteurs du transport de la serotonine
AU2002348135A1 (en) *	2001-10-31	2003-05-12	Recovery Pharmaceuticals, Inc.	Methods for the treatment of addiction
US7381733B2 (en)	2001-11-30	2008-06-03	Neurosearch A/S	Tropane derivatives having dopamine reuptake inhibitor activity for the treatment of ischemic diseases
CA2484482C (fr)	2002-05-30	2011-07-26	Neurosearch A/S	Triple inhibiteurs de recaptage de momoamine pour le traitement de douleur chronique
WO2004039778A1 (fr)	2002-11-01	2004-05-13	Neurosearch A/S	Nouveaux derives de piperidine et leur utilisation en tant qu'inhibiteurs de recaptage de neurotransmetteurs de la monoamine
EP2412719A1 (fr)	2002-12-02	2012-02-01	Xenome Ltd	Pptides de chi-conotoxine
WO2004050690A1 (fr)	2002-12-02	2004-06-17	Xenome Ltd	Nouveaux peptides (-i) de $g(x)-conotoxine
CN100551924C (zh) *	2003-02-12	2009-10-21	神经研究公司	8-氮杂-双环[3.2.1]辛烷衍生物和它们作为单胺神经递质再摄取抑制剂的用途
WO2004072071A1 (fr)	2003-02-12	2004-08-26	Neurosearch A/S	8 nouveaux derives de 8-aza-bicyclo[3.2.1]octane et leur utilisation en tant qu'inhibiteurs du recaptage des neurotransmetteurs monoamines
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1997
- 1997-02-21 JP JP52981097A patent/JP3238414B2/ja not_active Expired - Fee Related
- 1997-02-21 EP EP97903355A patent/EP0885220B1/fr not_active Expired - Lifetime
- 1997-02-21 DE DE69705608T patent/DE69705608T2/de not_active Expired - Lifetime
- 1997-02-21 SG SG9903902A patent/SG99853A1/en unknown
- 1997-02-21 ES ES97903355T patent/ES2159839T3/es not_active Expired - Lifetime
- 1997-02-21 EP EP01108256A patent/EP1130020A1/fr not_active Withdrawn
- 1997-02-21 IL IL12514697A patent/IL125146A/en not_active IP Right Cessation
- 1997-02-21 CZ CZ19982520A patent/CZ287007B6/cs not_active IP Right Cessation
- 1997-02-21 SK SK929-98A patent/SK281813B6/sk not_active IP Right Cessation
- 1997-02-21 AU AU17940/97A patent/AU720358B2/en not_active Ceased
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- 1997-02-21 CA CA002244773A patent/CA2244773C/fr not_active Expired - Lifetime
- 1997-02-21 BR BR9707636A patent/BR9707636A/pt not_active IP Right Cessation
- 1997-02-21 HU HU9901199A patent/HU228356B1/hu not_active IP Right Cessation
- 1997-02-21 PT PT97903355T patent/PT885220E/pt unknown
- 1997-02-21 RU RU98117314/04A patent/RU2167876C2/ru active
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- 1997-02-21 PL PL97328503A patent/PL185132B1/pl not_active IP Right Cessation
- 1997-02-21 KR KR10-1998-0706518A patent/KR100446571B1/ko not_active Expired - Fee Related
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- 1997-02-21 WO PCT/EP1997/000850 patent/WO1997030997A1/fr not_active Ceased
- 1997-02-21 SI SI9730163T patent/SI0885220T1/xx unknown
- 1997-02-21 UA UA98073814A patent/UA49872C2/uk unknown
- 1997-02-21 AT AT97903355T patent/ATE203023T1/de active
- 1997-02-21 EE EE9800254A patent/EE04751B1/xx not_active IP Right Cessation
- 1997-02-21 US US09/101,524 patent/US6288079B1/en not_active Expired - Lifetime
- 1997-02-21 CN CN97192505A patent/CN1077574C/zh not_active Expired - Fee Related
1998
- 1998-07-15 BG BG102637A patent/BG63945B1/bg unknown
- 1998-08-17 IS IS4825A patent/IS1824B/is unknown
- 1998-08-21 NO NO19983877A patent/NO318731B1/no not_active IP Right Cessation
2001
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2002
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Publication number	Publication date
SK281813B6 (sk)	2001-08-06
PL185132B1 (pl)	2003-02-28
BG102637A (en)	1999-06-30
US6395748B2 (en)	2002-05-28
JP3238414B2 (ja)	2001-12-17
EP0885220A1 (fr)	1998-12-23
HU228356B1 (en)	2013-03-28
HK1018957A1 (en)	2000-01-14
WO1997030997A1 (fr)	1997-08-28
AU1794097A (en)	1997-09-10
TR199801641T2 (xx)	1998-11-23
KR100446571B1 (ko)	2004-11-03
CN1077574C (zh)	2002-01-09
EE9800254A (et)	1999-02-15
DK0885220T3 (da)	2001-10-15
BG63945B1 (bg)	2003-07-31
DE69705608D1 (de)	2001-08-16
CA2244773A1 (fr)	1997-08-28
CA2244773C (fr)	2006-01-03
NO318731B1 (no)	2005-05-02
RU2167876C2 (ru)	2001-05-27
NO983877D0 (no)	1998-08-21
AU720358B2 (en)	2000-06-01
US20020128284A1 (en)	2002-09-12
HUP9901199A3 (en)	2001-02-28
CN1211982A (zh)	1999-03-24
SG99853A1 (en)	2003-11-27
GR3036829T3 (en)	2002-01-31
ES2159839T3 (es)	2001-10-16
CZ252098A3 (cs)	1998-11-11
DE69705608T2 (de)	2002-05-16
JP2000504739A (ja)	2000-04-18
IS1824B (is)	2002-10-01
EP1130020A1 (fr)	2001-09-05
EE04751B1 (et)	2006-12-15
EP0885220B1 (fr)	2001-07-11
SK92998A3 (en)	1998-11-04
SI0885220T1 (en)	2001-12-31
NO983877L (no)	1998-08-21
HUP9901199A2 (hu)	1999-08-30
IL125146A0 (en)	1999-01-26
KR19990087127A (ko)	1999-12-15
BR9707636A (pt)	1999-07-27
PT885220E (pt)	2001-11-30
CZ287007B6 (en)	2000-08-16
US6288079B1 (en)	2001-09-11
US20010018444A1 (en)	2001-08-30
IS4825A (is)	1998-08-17
PL328503A1 (en)	1999-02-01
NZ330886A (en)	1999-02-25
UA49872C2 (uk)	2002-10-15
ZA971525B (en)	1997-10-21
ATE203023T1 (de)	2001-07-15

Legal Events

Date	Code	Title
2002-08-14	FF	Patent granted
2002-08-14	KB	Patent renewed
2003-04-10	KB	Patent renewed
2007-05-21	KB	Patent renewed
2011-02-28	KB	Patent renewed
2015-09-24	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
US6288079B1 (en)	2001-09-11	Tropane-derivatives, their preparation and use
US5998405A (en)	1999-12-07	Fused tropane-derivatives as neurotransmitter reuptake inhibitors
SK28798A3 (en)	1998-09-09	8-azabicyclo[3.2.1]oct-2-ene derivatives, their preparation and use
EP0756596B1 (fr)	2002-08-21	Derives de tropane-2-aldoxime en tant qu'inhibiteurs de recaptage des neurotransmetteurs
US6376673B1 (en)	2002-04-23	Piperidine derivatives as neurotransmitter re-uptake inhibitors
JP4588444B2 (ja)	2010-12-01	ジアザビシクロノナン及び−デカン誘導体並びにこれをオピオイドレセプターリガンドとして使用する方法
JPH06293759A (ja)	1994-10-21	アルキル置換複素環式化合物
MXPA98003554A (en)	1998-11-16	Frozen tropan derivatives, its preparation and