NO823344L - 3-fenyl-1-indanaminer. - Google Patents
3-fenyl-1-indanaminer.Info
- Publication number
- NO823344L NO823344L NO823344A NO823344A NO823344L NO 823344 L NO823344 L NO 823344L NO 823344 A NO823344 A NO 823344A NO 823344 A NO823344 A NO 823344A NO 823344 L NO823344 L NO 823344L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- hydrogen
- compound
- indanamine
- indicated above
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 26
- 239000002585 base Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 24
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000003638 chemical reducing agent Substances 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- SPHAWXCQQFPLSS-UHFFFAOYSA-N 3-phenyl-2,3-dihydro-1h-inden-1-amine Chemical class C12=CC=CC=C2C(N)CC1C1=CC=CC=C1 SPHAWXCQQFPLSS-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 238000005932 reductive alkylation reaction Methods 0.000 claims description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical group NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000002642 lithium compounds Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- UNCBFTIAWJTNTF-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-n,n-dimethyl-2,3-dihydro-1h-inden-1-amine Chemical group C12=CC=CC=C2C(N(C)C)CC1C1=CC=C(Cl)C(Cl)=C1 UNCBFTIAWJTNTF-UHFFFAOYSA-N 0.000 claims 1
- SVFXPTLYMIXFRX-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-n-methyl-2,3-dihydro-1h-inden-1-amine Chemical group C12=CC=CC=C2C(NC)CC1C1=CC=C(Cl)C(Cl)=C1 SVFXPTLYMIXFRX-UHFFFAOYSA-N 0.000 claims 1
- FAVRAXVBHORDCR-UHFFFAOYSA-N 3-(4-bromophenyl)-n,n-dimethyl-2,3-dihydro-1h-inden-1-amine Chemical group C12=CC=CC=C2C(N(C)C)CC1C1=CC=C(Br)C=C1 FAVRAXVBHORDCR-UHFFFAOYSA-N 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 72
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- 239000000243 solution Substances 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- -1 n-amyl Chemical group 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 239000008363 phosphate buffer Substances 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000012047 saturated solution Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- NOIIUHRQUVNIDD-UHFFFAOYSA-N 3-[[oxo(pyridin-4-yl)methyl]hydrazo]-N-(phenylmethyl)propanamide Chemical compound C=1C=CC=CC=1CNC(=O)CCNNC(=O)C1=CC=NC=C1 NOIIUHRQUVNIDD-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 206010015995 Eyelid ptosis Diseases 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 229930006000 Sucrose Natural products 0.000 description 6
- 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 6
- 229960003638 dopamine Drugs 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 229960003057 nialamide Drugs 0.000 description 6
- 201000003004 ptosis Diseases 0.000 description 6
- 239000005720 sucrose Substances 0.000 description 6
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 5
- 210000004556 brain Anatomy 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 150000003840 hydrochlorides Chemical class 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 231100000252 nontoxic Toxicity 0.000 description 5
- 230000003000 nontoxic effect Effects 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 230000001519 thymoleptic effect Effects 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000000935 antidepressant agent Substances 0.000 description 4
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- 239000012259 ether extract Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- YIAPLDFPUUJILH-UHFFFAOYSA-N indan-1-ol Chemical compound C1=CC=C2C(O)CCC2=C1 YIAPLDFPUUJILH-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 3
- SVFXPTLYMIXFRX-XJKSGUPXSA-N (1R,3S)-3-(3,4-dichlorophenyl)-N-methyl-2,3-dihydro-1H-inden-1-amine Chemical compound C1([C@@H]2C[C@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 SVFXPTLYMIXFRX-XJKSGUPXSA-N 0.000 description 3
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- 208000020401 Depressive disease Diseases 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 3
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- 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
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- 238000005119 centrifugation Methods 0.000 description 3
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- 239000008103 glucose Substances 0.000 description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
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- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 235000019799 monosodium phosphate Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000009871 nonspecific binding Effects 0.000 description 3
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 3
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- 238000000746 purification Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 3
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- 208000024891 symptom Diseases 0.000 description 3
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- HDXFCPZKMFTOLH-UHFFFAOYSA-N 1-amino-2,3-dihydroinden-1-ol Chemical compound C1=CC=C2C(N)(O)CCC2=C1 HDXFCPZKMFTOLH-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- PQBBNIIAALJDCF-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-methyl-2,3-dihydroinden-1-imine Chemical compound C12=CC=CC=C2C(=NC)CC1C1=CC=C(F)C=C1 PQBBNIIAALJDCF-UHFFFAOYSA-N 0.000 description 2
- UGPNWCKKVXUXBJ-UHFFFAOYSA-N 3-(dimethylamino)-2,3-dihydroinden-1-one Chemical compound C1=CC=C2C(N(C)C)CC(=O)C2=C1 UGPNWCKKVXUXBJ-UHFFFAOYSA-N 0.000 description 2
- BSAIUCUXHVGXNK-UHFFFAOYSA-N 3-bromo-2,3-dihydroinden-1-one Chemical class C1=CC=C2C(Br)CC(=O)C2=C1 BSAIUCUXHVGXNK-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- 150000001721 carbon Chemical group 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- 239000002552 dosage form Substances 0.000 description 2
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- 239000000543 intermediate Substances 0.000 description 2
- 238000005567 liquid scintillation counting Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8130009 | 1981-10-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO823344L true NO823344L (no) | 1983-04-06 |
Family
ID=10524953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO823344A NO823344L (no) | 1981-10-05 | 1982-10-04 | 3-fenyl-1-indanaminer. |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0076669A1 (el) |
| JP (1) | JPS5877846A (el) |
| AU (1) | AU8898282A (el) |
| DK (1) | DK438482A (el) |
| ES (1) | ES516184A0 (el) |
| FI (1) | FI823360L (el) |
| GR (1) | GR76712B (el) |
| IL (1) | IL66831A0 (el) |
| NO (1) | NO823344L (el) |
| PT (1) | PT75636B (el) |
| ZA (1) | ZA826924B (el) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4866208A (en) * | 1981-12-21 | 1989-09-12 | The Dow Chemical Company | Meta-phenylene diamine derivatives |
| JPS6169747A (ja) * | 1984-08-31 | 1986-04-10 | Otsuka Pharmaceut Co Ltd | ２，３―ジヒドロ―１ｈ―インデン誘導体及びその製造法 |
| DE3583780D1 (de) * | 1984-08-31 | 1991-09-19 | Otsuka Pharma Co Ltd | 2,3-dihydro-1h-inden-derivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen. |
| GB8628644D0 (en) * | 1986-12-01 | 1987-01-07 | Lunbeck A S H | Intermediates |
| WO1998006689A1 (en) * | 1996-08-16 | 1998-02-19 | Allelix Pharm-Eco, L.L.P. | Slow-onset, long-lasting dopamine reuptake blockers |
| US5821386A (en) * | 1997-08-15 | 1998-10-13 | Allelix-Pharm-Eco L.P. | Compounds for treating cocaine abuse |
| WO1999035119A1 (en) * | 1998-01-09 | 1999-07-15 | Pharm-Eco Laboratories, Inc. | Synthesis of 3-aryl-1-indanamines |
| DE29923134U1 (de) * | 1999-11-16 | 2000-06-29 | Schwarz Pharma Ag, 40789 Monheim | Stabile Salze neuartiger Derviate von 3,3-Diphenylpropylaminen |
| EP2911695B1 (en) * | 2012-10-26 | 2023-11-29 | Palomo Limited | Compositions and methods for the treatment of parkinson disease by the selective delivery of oligonucleotide molecules to specific neuron types |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE955594C (de) * | 1953-11-15 | 1957-01-03 | Schering Ag | Verfahren zur Herstellung von 3-Aminoindanen |
| GB971917A (en) * | 1960-11-08 | 1964-10-07 | Schering Ag | New aminoindanes and a process for their manufacture |
| DE2339715A1 (de) * | 1973-08-06 | 1975-02-27 | Hoechst Ag | Basisch substituierte phenylindane und verfahren zu ihrer herstellung |
| NZ196284A (en) * | 1980-02-29 | 1983-12-16 | Kefalas As | 1-piperazino-3-phenylindane derivatives:pharmaceutical compositions |
-
1982
- 1982-09-17 IL IL66831A patent/IL66831A0/xx unknown
- 1982-09-21 ZA ZA826924A patent/ZA826924B/xx unknown
- 1982-10-01 FI FI823360A patent/FI823360L/fi not_active Application Discontinuation
- 1982-10-01 EP EP82305244A patent/EP0076669A1/en not_active Ceased
- 1982-10-01 PT PT75636A patent/PT75636B/pt unknown
- 1982-10-01 GR GR69418A patent/GR76712B/el unknown
- 1982-10-04 AU AU88982/82A patent/AU8898282A/en not_active Abandoned
- 1982-10-04 ES ES516184A patent/ES516184A0/es active Granted
- 1982-10-04 DK DK438482A patent/DK438482A/da not_active Application Discontinuation
- 1982-10-04 NO NO823344A patent/NO823344L/no unknown
- 1982-10-05 JP JP57174106A patent/JPS5877846A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0076669A1 (en) | 1983-04-13 |
| AU8898282A (en) | 1983-04-14 |
| ZA826924B (en) | 1983-08-31 |
| ES8308833A1 (es) | 1983-10-01 |
| FI823360A0 (fi) | 1982-10-01 |
| DK438482A (da) | 1983-04-06 |
| FI823360L (fi) | 1983-04-06 |
| JPS5877846A (ja) | 1983-05-11 |
| PT75636B (en) | 1985-01-11 |
| PT75636A (en) | 1982-11-01 |
| GR76712B (el) | 1984-08-29 |
| IL66831A0 (en) | 1982-12-31 |
| ES516184A0 (es) | 1983-10-01 |
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