DD298909A5 - Verfahren zur herstellung 8-substituierter 2-aminotetraline - Google Patents

Verfahren zur herstellung 8-substituierter 2-aminotetraline Download PDF

Info

Publication number: DD298909A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; aryl; hydrogen; dor; compound
Prior art date: 1989-05-26

Application number

DD90340992A

Other languages

German (de)

English (en)

Inventor

Nils-Erik Anden

Hoeoek Berit Ch E Backlund

Anna L M Bjoerk

Uli A Hacksell

Sven-Erik Hillver

Liu Ye

Eva Ch Mellin

Eva M Persson

Karl J Vallgarda

Yu Hong

Original Assignee

��@��k��

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.)

1989-05-26

Filing date

1990-05-25

Publication date

1992-03-19

1990-05-25 Application filed by ��@��k�� filed Critical ��@��k��

1992-03-19 Publication of DD298909A5 publication Critical patent/DD298909A5/de

Links

-1 8-SUBSTITUTED 2-AMINOTETRALINE Chemical class 0.000 title claims description 36
238000004519 manufacturing process Methods 0.000 title description 2
125000003118 aryl group Chemical group 0.000 claims abstract description 31
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
239000001257 hydrogen Substances 0.000 claims abstract description 22
150000001875 compounds Chemical class 0.000 claims abstract description 16
229910052736 halogen Inorganic materials 0.000 claims abstract description 15
150000002367 halogens Chemical class 0.000 claims abstract description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
238000011282 treatment Methods 0.000 claims abstract description 8
238000000034 method Methods 0.000 claims abstract description 6
150000003839 salts Chemical class 0.000 claims abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
125000005842 heteroatom Chemical group 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 3
125000000217 alkyl group Chemical group 0.000 claims description 36
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 27
235000019256 formaldehyde Nutrition 0.000 claims description 27
229960004279 formaldehyde Drugs 0.000 claims description 27
239000000203 mixture Substances 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 16
125000003710 aryl alkyl group Chemical group 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 10
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 9
229910002091 carbon monoxide Inorganic materials 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
229910052723 transition metal Inorganic materials 0.000 claims description 4
150000003624 transition metals Chemical class 0.000 claims description 4
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
229910052796 boron Inorganic materials 0.000 claims description 2
125000001207 fluorophenyl group Chemical group 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 3
125000003342 alkenyl group Chemical group 0.000 claims 2
238000006464 oxidative addition reaction Methods 0.000 claims 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
235000012571 Ficus glomerata Nutrition 0.000 claims 1
240000000365 Ficus racemosa Species 0.000 claims 1
235000015125 Sterculia urens Nutrition 0.000 claims 1
238000000137 annealing Methods 0.000 claims 1
150000005840 aryl radicals Chemical class 0.000 claims 1
239000002585 base Substances 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 claims 1
125000004663 dialkyl amino group Chemical group 0.000 claims 1
230000007062 hydrolysis Effects 0.000 claims 1
238000006460 hydrolysis reaction Methods 0.000 claims 1
125000006431 methyl cyclopropyl group Chemical group 0.000 claims 1
125000002524 organometallic group Chemical group 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 3
239000000825 pharmaceutical preparation Substances 0.000 abstract description 2
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 abstract 1
208000035475 disorder Diseases 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 29
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 18
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 18
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 17
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
239000000243 solution Substances 0.000 description 12
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
239000003054 catalyst Substances 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
239000003814 drug Substances 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
230000005062 synaptic transmission Effects 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000010410 layer Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
235000006408 oxalic acid Nutrition 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
239000002243 precursor Substances 0.000 description 5
WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 5
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 4
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000011534 incubation Methods 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000006467 substitution reaction Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000013543 active substance Substances 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
210000003169 central nervous system Anatomy 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000002808 molecular sieve Substances 0.000 description 3
MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 3
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
229920000945 Amylopectin Polymers 0.000 description 2
208000019901 Anxiety disease Diseases 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
208000020401 Depressive disease Diseases 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
229930006000 Sucrose Natural products 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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
230000036506 anxiety Effects 0.000 description 2
235000010323 ascorbic acid Nutrition 0.000 description 2
229960005070 ascorbic acid Drugs 0.000 description 2
239000011668 ascorbic acid Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000004927 clay Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
235000008504 concentrate Nutrition 0.000 description 2
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
230000006872 improvement Effects 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000002858 neurotransmitter agent Substances 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
COHOGNZHAUOXPA-UHFFFAOYSA-N trimethyl(phenyl)stannane Chemical compound C[Sn](C)(C)C1=CC=CC=C1 COHOGNZHAUOXPA-UHFFFAOYSA-N 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
125000006727 (C1-C6) alkenyl group Chemical group 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
PYBXNVMQWQTECE-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-ol hydrochloride Chemical compound Cl.C1=CC=C2C(O)CCCC2=C1 PYBXNVMQWQTECE-UHFFFAOYSA-N 0.000 description 1
HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-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
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 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
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
241000263296 Diodon Species 0.000 description 1
241000790917 Dioxys <bee> Species 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
235000019759 Maize starch Nutrition 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000005662 Paraffin oil Substances 0.000 description 1
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CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
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239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
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239000010802 sludge Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
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239000003381 stabilizer Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
235000013547 stew Nutrition 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
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235000020357 syrup Nutrition 0.000 description 1
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Substances C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
- C07C211/41—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems
- C07C211/42—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems with six-membered aromatic rings being part of the condensed ring systems
- 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
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, 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
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/20—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C229/50—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms being part of the same condensed ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Hospice & Palliative Care (AREA)
Anesthesiology (AREA)
Urology & Nephrology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Nutrition Science (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Peptides Or Proteins (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Indole Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Thiazole And Isothizaole Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Furan Compounds (AREA)
Hydrogenated Pyridines (AREA)
Saccharide Compounds (AREA)

DD90340992A 1989-05-26 1990-05-25 Verfahren zur herstellung 8-substituierter 2-aminotetraline DD298909A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SE8901889A SE8901889D0 (sv)	1989-05-26	1989-05-26	Novel 8-substituted-2-aminotetralines

Publications (1)

Publication Number	Publication Date
DD298909A5 true DD298909A5 (de)	1992-03-19

Family

ID=20376074

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90340992A DD298909A5 (de)	1989-05-26	1990-05-25	Verfahren zur herstellung 8-substituierter 2-aminotetraline

Country Status (41)

Country	Link
US (1)	US5635537A (da)
EP (1)	EP0399982B1 (da)
JP (1)	JP2818692B2 (da)
KR (1)	KR100193981B1 (da)
CN (1)	CN1023399C (da)
AT (1)	ATE129696T1 (da)
AU (1)	AU644081B2 (da)
CA (1)	CA2032498C (da)
CY (1)	CY1989A (da)
CZ (1)	CZ286038B6 (da)
DD (1)	DD298909A5 (da)
DE (1)	DE69023274T2 (da)
DK (1)	DK0399982T3 (da)
DZ (1)	DZ1417A1 (da)
ES (1)	ES2078962T3 (da)
FI (1)	FI114151B (da)
GR (1)	GR3018566T3 (da)
HK (1)	HK55697A (da)
HR (1)	HRP920622B1 (da)
HU (2)	HUT58685A (da)
IE (1)	IE75057B1 (da)
IL (1)	IL94428A (da)
IS (1)	IS1663B (da)
JO (1)	JO1617B1 (da)
LT (1)	LT3966B (da)
LV (2)	LV10243B (da)
MX (1)	MX20842A (da)
NO (1)	NO176603C (da)
NZ (1)	NZ233724A (da)
PH (1)	PH31110A (da)
PL (2)	PL165166B1 (da)
PT (1)	PT94163B (da)
RU (1)	RU2093507C1 (da)
SA (1)	SA90100274B1 (da)
SE (1)	SE8901889D0 (da)
SI (1)	SI9011006B (da)
SK (1)	SK256090A3 (da)
UA (1)	UA40562C2 (da)
WO (1)	WO1990014330A1 (da)
YU (1)	YU48830B (da)
ZA (1)	ZA903801B (da)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2785879B2 (ja)	1989-05-31	1998-08-13	ジ・アップジョン・カンパニー	治療学的に有用な２―アミノテトラリン誘導体
EP0471515B1 (en) *	1990-08-15	1997-03-05	Eli Lilly And Company	Ring-substituted 2-amino-1,2,3,4-tetra-hydronaphthalenes, 3-aminochromanes and 3-aminothiochromanes
US5643784A (en) *	1990-12-04	1997-07-01	H, Lundbeck A/S	Indan derivatives
IL114760A (en) *	1991-02-08	1997-11-20	Lilly Co Eli	Ring-substituted-2-amino-1,2,3,4-tetrahydronaphthalenes and 3-aminochromanes intermediates thereto
US5643934A (en) *	1991-03-28	1997-07-01	Eli Lilly And Company	6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz [CD]indoles
US5244911A (en) *	1991-03-28	1993-09-14	Eli Lilly And Company	6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz(cd)indoles and pharmaceutical use thereof
US5347013A (en) *	1991-03-28	1994-09-13	Eli Lilly And Company	6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz[cd]indoles
US5244912A (en) *	1991-03-28	1993-09-14	Eli Lilly And Company	6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz(cd)indoles and pharmaceutical use thereof
NZ243065A (en)	1991-06-13	1995-07-26	Lundbeck & Co As H	Piperidine derivatives and pharmaceutical compositions
SE9103745D0 (sv) *	1991-12-18	1991-12-18	Wikstroem Haakan	Aryl-triflates and related compounds
DK78692D0 (da) *	1992-06-12	1992-06-12	Lundbeck & Co As H	Dimere piperidin- og piperazinderivater
SE9301732D0 (sv) *	1993-05-18	1993-05-18	Haakan Wilhelm Wikstroem	New centrally acting 5-,6-,7-, and 8-substituted sulphone esters of n-monosubstituted 2-aminotetralins
AU1106195A (en) *	1994-11-09	1996-06-06	Novo Nordisk A/S	Heterocyclic compounds, their preparation and use
GB9509156D0 (en) *	1995-05-05	1995-06-28	Sandoz Ltd	Organic compounds
CN101119965B (zh) *	2004-12-21	2012-09-26	弗·哈夫曼-拉罗切有限公司	萘满和茚满衍生物及其用途
ATE409179T1 (de) *	2004-12-21	2008-10-15	Hoffmann La Roche	Tetralin- und indanderivate und deren anwendungen als 5-ht-antagonisten
US8053603B2 (en)	2006-01-06	2011-11-08	Sunovion Pharmaceuticals Inc.	Tetralone-based monoamine reuptake inhibitors
EP4308603A1 (en)	2021-03-17	2024-01-24	Receptos Llc	Methods of treating atopic dermatitis with anti il-13 antibodies

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2752659A1 (de) *	1976-12-07	1978-06-08	Sandoz Ag	Neue tetralinderivate, ihre herstellung und verwendung
US4247907A (en) *	1978-11-27	1981-01-27	International Business Machines Corporation	Method and apparatus for typing characters and optically readable binary representations thereof on same page
SE8004002L (sv) *	1980-05-29	1981-11-30	Arvidsson Folke Lars Erik	Terapeutiskt anvendbara tetralinderivat
IL65501A (en) *	1981-05-08	1986-04-29	Astra Laekemedel Ab	1-alkyl-2-aminotetralin derivatives,process for their preparation and pharmaceutical compositions containing them
DE3479314D1 (en) *	1984-05-22	1989-09-14	Nelson Res & Dev	Substituted 2-aminotetralins and processes for synthesis
DE3660959D1 (de) *	1985-06-26	1988-11-24	Smithkline Beckman Corp	Benz-trisubstituted 2-aminotetralins
IL79323A (en) *	1985-07-10	1990-03-19	Sanofi Sa	Phenylethanolaminotetralines,their preparation and pharmaceutical compositions containing them
DE3718317A1 (de) *	1986-12-10	1988-06-16	Bayer Ag	Substituierte basische 2-aminotetraline
DE3719924A1 (de) *	1986-12-22	1988-06-30	Bayer Ag	8-substituierte 2-aminotetraline
DK0452390T3 (da) *	1989-01-09	1995-04-03	Upjohn Co	Halogensubstituerede aminotetraliner
JP2785879B2 (ja) *	1989-05-31	1998-08-13	ジ・アップジョン・カンパニー	治療学的に有用な２―アミノテトラリン誘導体

1989
- 1989-05-26 SE SE8901889A patent/SE8901889D0/xx unknown
1990
- 1990-05-17 IL IL9442890A patent/IL94428A/en not_active IP Right Cessation
- 1990-05-17 ZA ZA903801A patent/ZA903801B/xx unknown
- 1990-05-18 NZ NZ233724A patent/NZ233724A/xx unknown
- 1990-05-22 IE IE183390A patent/IE75057B1/en not_active IP Right Cessation
- 1990-05-23 KR KR1019910700092A patent/KR100193981B1/ko not_active Expired - Fee Related
- 1990-05-23 DE DE69023274T patent/DE69023274T2/de not_active Expired - Lifetime
- 1990-05-23 JP JP2508698A patent/JP2818692B2/ja not_active Expired - Lifetime
- 1990-05-23 HU HU904810A patent/HUT58685A/hu unknown
- 1990-05-23 AT AT90850209T patent/ATE129696T1/de not_active IP Right Cessation
- 1990-05-23 ES ES90850209T patent/ES2078962T3/es not_active Expired - Lifetime
- 1990-05-23 EP EP90850209A patent/EP0399982B1/en not_active Expired - Lifetime
- 1990-05-23 DZ DZ900088A patent/DZ1417A1/fr active
- 1990-05-23 MX MX2084290A patent/MX20842A/es unknown
- 1990-05-23 UA UA4894777A patent/UA40562C2/uk unknown
- 1990-05-23 RU SU904894777A patent/RU2093507C1/ru active
- 1990-05-23 DK DK90850209.9T patent/DK0399982T3/da active
- 1990-05-23 SI SI9011006A patent/SI9011006B/sl unknown
- 1990-05-23 CA CA002032498A patent/CA2032498C/en not_active Expired - Lifetime
- 1990-05-23 IS IS3580A patent/IS1663B/is unknown
- 1990-05-23 YU YU100690A patent/YU48830B/sh unknown
- 1990-05-23 WO PCT/SE1990/000351 patent/WO1990014330A1/en not_active Ceased
- 1990-05-23 AU AU58185/90A patent/AU644081B2/en not_active Expired
- 1990-05-24 PL PL90285330A patent/PL165166B1/pl unknown
- 1990-05-24 PL PL90300984A patent/PL164245B1/pl unknown
- 1990-05-25 PT PT94163A patent/PT94163B/pt not_active IP Right Cessation
- 1990-05-25 CZ CS902560A patent/CZ286038B6/cs not_active IP Right Cessation
- 1990-05-25 SK SK2560-90A patent/SK256090A3/sk not_active IP Right Cessation
- 1990-05-25 DD DD90340992A patent/DD298909A5/de unknown
- 1990-05-25 PH PH40567A patent/PH31110A/en unknown
- 1990-05-26 JO JO19901617A patent/JO1617B1/en active
- 1990-05-26 CN CN90103956A patent/CN1023399C/zh not_active Expired - Lifetime
- 1990-06-09 SA SA90100274A patent/SA90100274B1/ar unknown
1991
- 1991-01-25 FI FI910381A patent/FI114151B/fi active
- 1991-01-25 NO NO910310A patent/NO176603C/no not_active IP Right Cessation
1992
- 1992-09-30 HR HRP-1006/90A patent/HRP920622B1/xx not_active IP Right Cessation
1993
- 1993-03-18 US US08/033,013 patent/US5635537A/en not_active Expired - Lifetime
- 1993-06-30 LV LVP-93-869A patent/LV10243B/xx unknown
- 1993-12-30 LT LTIP1723A patent/LT3966B/lt not_active IP Right Cessation
1995
- 1995-06-30 HU HU95P/P00719P patent/HU211880A9/hu unknown
- 1995-12-29 GR GR950403703T patent/GR3018566T3/el unknown
1996
- 1996-11-01 LV LVP-96-420A patent/LV11736B/en unknown
1997
- 1997-05-01 HK HK55697A patent/HK55697A/en not_active IP Right Cessation
- 1997-09-05 CY CY198997A patent/CY1989A/xx unknown

Also Published As

Publication number	Publication date
NO910310D0 (no)	1991-01-25
NO176603B (no)	1995-01-23
PL165166B1 (pl)	1994-11-30
SA90100274B1 (ar)	2005-06-01
LV11736A (lv)	1997-04-20
ATE129696T1 (de)	1995-11-15
YU100690A (en)	1992-05-28
ZA903801B (en)	1991-01-30
FI910381A0 (fi)	1991-01-25
IS1663B (is)	1997-07-04
HK55697A (en)	1997-05-09
SI9011006B (sl)	1998-12-31
PL164245B1 (pl)	1994-07-29
HRP920622B1 (en)	2000-04-30
EP0399982B1 (en)	1995-11-02
US5635537A (en)	1997-06-03
GR3018566T3 (en)	1996-03-31
DE69023274T2 (de)	1996-04-11
LV11736B (en)	1997-10-20
HU904810D0 (en)	1991-06-28
FI114151B (fi)	2004-08-31
KR920701121A (ko)	1992-08-11
CA2032498A1 (en)	1990-11-27
SE8901889D0 (sv)	1989-05-26
CN1023399C (zh)	1994-01-05
PL285330A1 (en)	1991-11-04
SK280731B6 (sk)	2000-07-11
NO176603C (no)	1995-05-03
LTIP1723A (en)	1995-08-25
PH31110A (en)	1998-02-23
SK256090A3 (en)	2000-07-11
NO910310L (no)	1991-01-25
ES2078962T3 (es)	1996-01-01
SI9011006A (en)	1997-12-31
JP2818692B2 (ja)	1998-10-30
DK0399982T3 (da)	1996-03-04
IE75057B1 (en)	1997-08-27
DE69023274D1 (de)	1995-12-07
HRP920622A2 (en)	1998-06-30
JPH04500362A (ja)	1992-01-23
CZ286038B6 (cs)	1999-12-15
NZ233724A (en)	1993-01-27
KR100193981B1 (ko)	1999-06-15
WO1990014330A1 (en)	1990-11-29
DZ1417A1 (fr)	2004-09-13
RU2093507C1 (ru)	1997-10-20
LV10243B (en)	1995-04-20
CA2032498C (en)	2002-03-26
AU5818590A (en)	1990-12-18
AU644081B2 (en)	1993-12-02
IS3580A7 (is)	1990-11-27
PT94163B (pt)	1996-12-31
IL94428A0 (en)	1991-03-10
YU48830B (sh)	2002-03-18
HU211880A9 (en)	1995-12-28
IE901833L (en)	1990-11-26
PT94163A (pt)	1991-01-08
LT3966B (en)	1996-05-27
HUT58685A (en)	1992-03-30
CY1989A (en)	1997-09-05
CN1047494A (zh)	1990-12-05
MX20842A (es)	1993-11-01
JO1617B1 (en)	1991-11-27
CZ256090A3 (cs)	1999-10-13
IL94428A (en)	1995-12-31
EP0399982A1 (en)	1990-11-28
LV10243A (lv)	1994-10-20
UA40562C2 (uk)	2001-08-15

Legal Events

Date	Code	Title	Description
2004-04-28	IF04	In force in the year 2004	Expiry date: 20100526

Publication	Publication Date	Title
DE69704679T2 (de)	2001-09-13	4-phenylpiperidin-derivate
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DE69701298T2 (de)	2000-10-05	Hydroxypyridin-Derivate, ihre Herstellung und ihre pharmazeutische Verwendung
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DE69617995T2 (de)	2002-05-16	Indolalkylderivate von benzodioxanmenthylamin als 5-ht1a rezeptor liganden
DE3853863T2 (de)	1995-09-21	4-Aminopyridinderivate.
DE69023274T2 (de)	1996-04-11	8-Substituierte-2-Aminotetraline.
DE3878371T2 (de)	1993-07-08	Psychotropische bizyklische imide.
DD273633A5 (de)	1989-11-22	Verfahren zur herstellung von 4-aminopyridin-derivaten
DD264919A5 (de)	1989-02-15	Verfahren zur herstellung von 5-hydroxy-3-aminochromanen
DE2539907A1 (de)	1976-03-25	4a-aryl-cis-decahydroisochinoline und diese verbindungen enthaltende arzneimittel
DE2347142A1 (de)	1974-04-25	Chemisches verfahren
DE69510510T2 (de)	1999-11-18	N-benzoylmethylsubstituierte paroxetinderivate
DE2016721A1 (da)	1970-10-29
DE2364685A1 (de)	1975-07-03	Phenoxyalkylamine und verfahren zu ihrer herstellung
DE69022442T2 (de)	1996-05-09	Aminoalkoxyphenyl-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Zusammensetzungen.
DE3419223A1 (de)	1984-12-06	Substituierte acylpiperazinochinazoline, ein verfahren zu deren herstellung und diese enthaltende pharmazeutische zubereitungen
DE3223877C2 (da)	1990-08-30
DD275052A1 (de)	1990-01-10	Verfahren zur herstellung von 2,3,4,5,6,7-hexahydro-2,7-methano-1,5-benzoxozorin bzw.-1,4-benzoxazonin-verbindungen
DE69901522T2 (de)	2003-01-09	Benzozyclobutanverbindungen, deren Herstellungsverfahren und diese enthaltende pharmazeutische Zusammenstellungen
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