DK168290B1 - 4-Amino-2,3-alkylen-quinolinderivater, en fremgangsmåde til deres fremstilling og anvendelse til fremstilling af et lægemiddel med aktivitet til lettelse af hukommelses-dysfunktion samt farmaceutisk præparat indeholdende et af de nævnte derivater - Google Patents

4-Amino-2,3-alkylen-quinolinderivater, en fremgangsmåde til deres fremstilling og anvendelse til fremstilling af et lægemiddel med aktivitet til lettelse af hukommelses-dysfunktion samt farmaceutisk præparat indeholdende et af de nævnte derivater Download PDF

Info

Publication number: DK168290B1
Authority: DK; Denmark
Prior art keywords: lower alkyl; formula; compound; hydrogen; given above
Prior art date: 1988-11-16

Application number

DK571989A

Other languages

Danish (da)

English (en)

Other versions

DK571989D0 (da

DK571989A (da

Inventor

Gregory Michael Shutske

Iv John Dick Tomer

Original Assignee

Hoechst Roussel Pharma

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.)

1988-11-16

Filing date

1989-11-15

Publication date

1994-03-07

1989-11-15 Application filed by Hoechst Roussel Pharma filed Critical Hoechst Roussel Pharma

1989-11-15 Publication of DK571989D0 publication Critical patent/DK571989D0/da

1990-05-17 Publication of DK571989A publication Critical patent/DK571989A/da

1994-03-07 Application granted granted Critical

1994-03-07 Publication of DK168290B1 publication Critical patent/DK168290B1/da

Links

230000007074 memory dysfunction Effects 0.000 title claims abstract description 6
230000000694 effects Effects 0.000 title claims description 7
229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title claims description 3
239000003814 drug Substances 0.000 title claims description 3
239000008194 pharmaceutical composition Substances 0.000 title claims description 3
238000002360 preparation method Methods 0.000 title abstract description 11
238000000034 method Methods 0.000 title abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 121
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 70
239000001257 hydrogen Substances 0.000 claims abstract description 32
150000002431 hydrogen Chemical group 0.000 claims abstract description 25
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 8
150000002367 halogens Chemical class 0.000 claims abstract description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
125000001589 carboacyl group Chemical group 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims description 108
-1 formamide acetal Chemical class 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 7
229910052740 iodine Inorganic materials 0.000 claims description 6
OUNOOOJPOPXGMC-UHFFFAOYSA-N (9-amino-1,2,3,4-tetrahydroacridin-2-yl) acetate Chemical group C1=CC=C2C(N)=C(CC(OC(=O)C)CC3)C3=NC2=C1 OUNOOOJPOPXGMC-UHFFFAOYSA-N 0.000 claims description 4
PYCYYSWVRAEADT-UHFFFAOYSA-N 9-amino-1,2,3,4-tetrahydroacridin-2-ol Chemical group C1=CC=C2C(N)=C(CC(O)CC3)C3=NC2=C1 PYCYYSWVRAEADT-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
229910021529 ammonia Inorganic materials 0.000 claims description 4
238000003797 solvolysis reaction Methods 0.000 claims description 4
150000001263 acyl chlorides Chemical class 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
ITYFEHDODMKJTO-UHFFFAOYSA-N (9-amino-1,2,3,4-tetrahydroacridin-2-yl) hexanoate Chemical group C1=CC=C2C(N)=C(CC(OC(=O)CCCCC)CC3)C3=NC2=C1 ITYFEHDODMKJTO-UHFFFAOYSA-N 0.000 claims description 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 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
239000012453 solvate Substances 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
BUNBLKHZETWLOA-UHFFFAOYSA-N (9-amino-1,2,3,4-tetrahydroacridin-2-yl) butanoate Chemical group C1=CC=C2C(N)=C(CC(OC(=O)CCC)CC3)C3=NC2=C1 BUNBLKHZETWLOA-UHFFFAOYSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 claims 1
108090000623 proteins and genes Proteins 0.000 claims 1
208000024827 Alzheimer disease Diseases 0.000 abstract description 3
230000006949 cholinergic function Effects 0.000 abstract description 3
125000004122 cyclic group Chemical group 0.000 abstract 1
230000003247 decreasing effect Effects 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 64
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 44
229910052799 carbon Inorganic materials 0.000 description 38
239000011541 reaction mixture Substances 0.000 description 33
239000000203 mixture Substances 0.000 description 27
235000019439 ethyl acetate Nutrition 0.000 description 25
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
239000000047 product Substances 0.000 description 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
238000004458 analytical method Methods 0.000 description 19
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 16
239000003921 oil Substances 0.000 description 16
239000007787 solid Substances 0.000 description 15
238000001953 recrystallisation Methods 0.000 description 14
239000000725 suspension Substances 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
238000000354 decomposition reaction Methods 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
239000012074 organic phase Substances 0.000 description 11
239000000243 solution Substances 0.000 description 11
238000003818 flash chromatography Methods 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
235000019341 magnesium sulphate Nutrition 0.000 description 10
239000002904 solvent Substances 0.000 description 10
LMTURPQMQMCBTQ-UHFFFAOYSA-N 9-amino-1,2,3,4-tetrahydroacridin-2-ol;hydrochloride Chemical compound Cl.C1=CC=C2C(N)=C(CC(O)CC3)C3=NC2=C1 LMTURPQMQMCBTQ-UHFFFAOYSA-N 0.000 description 9
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 9
238000001665 trituration Methods 0.000 description 9
238000010438 heat treatment Methods 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
238000001035 drying Methods 0.000 description 7
239000000463 material Substances 0.000 description 7
238000000746 purification Methods 0.000 description 7
239000008096 xylene Substances 0.000 description 7
150000003738 xylenes Chemical class 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
AWQQHONKCURCNN-UHFFFAOYSA-N 2-phenylmethoxy-1,2,3,4-tetrahydroacridin-9-amine Chemical compound C1CC2=NC3=CC=CC=C3C(N)=C2CC1OCC1=CC=CC=C1 AWQQHONKCURCNN-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
238000001914 filtration Methods 0.000 description 5
239000003826 tablet Substances 0.000 description 5
AQQYGAAPUPCKOX-UHFFFAOYSA-N 4-phenylmethoxy-1,2,3,4-tetrahydroacridin-9-amine Chemical compound C12=NC3=CC=CC=C3C(N)=C2CCCC1OCC1=CC=CC=C1 AQQYGAAPUPCKOX-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000011592 zinc chloride Substances 0.000 description 4
235000005074 zinc chloride Nutrition 0.000 description 4
BISIFJGUTDFVFR-UHFFFAOYSA-N 9-amino-1,2,3,4-tetrahydroacridin-4-ol Chemical compound C1=CC=C2C(N)=C(CCCC3O)C3=NC2=C1 BISIFJGUTDFVFR-UHFFFAOYSA-N 0.000 description 3
229930000680 A04AD01 - Scopolamine Natural products 0.000 description 3
102100033639 Acetylcholinesterase Human genes 0.000 description 3
108010022752 Acetylcholinesterase Proteins 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 3
STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
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239000013081 microcrystal Substances 0.000 description 3
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239000000126 substance Substances 0.000 description 3
XAXVRJNWNPBYOM-UHFFFAOYSA-N (9-amino-1,2,3,4-tetrahydroacridin-2-yl) dodecanoate Chemical compound C1=CC=C2C(N)=C(CC(OC(=O)CCCCCCCCCCC)CC3)C3=NC2=C1 XAXVRJNWNPBYOM-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
FFGVIYUANJAFJS-UHFFFAOYSA-N 4-phenylmethoxycyclohexan-1-one Chemical compound C1CC(=O)CCC1OCC1=CC=CC=C1 FFGVIYUANJAFJS-UHFFFAOYSA-N 0.000 description 2
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CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
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229960000583 acetic acid Drugs 0.000 description 2
229940022698 acetylcholinesterase Drugs 0.000 description 2
238000003556 assay Methods 0.000 description 2
239000002585 base Substances 0.000 description 2
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239000003795 chemical substances by application Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 2
NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
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239000012458 free base Substances 0.000 description 2
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238000007327 hydrogenolysis reaction Methods 0.000 description 2
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 2
230000001771 impaired effect Effects 0.000 description 2
239000007788 liquid Substances 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
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
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OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
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PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
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PGFIGQYRXMHWLC-UHFFFAOYSA-N (9-amino-1,2,3,4-tetrahydroacridin-2-yl) propanoate Chemical compound C1=CC=C2C(N)=C(CC(OC(=O)CC)CC3)C3=NC2=C1 PGFIGQYRXMHWLC-UHFFFAOYSA-N 0.000 description 1
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ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
HLVVITIHAZBPKB-UHFFFAOYSA-N 9-amino-1,2,3,4-tetrahydroacridin-1-ol Chemical compound C1=CC=C2C(N)=C(C(O)CCC3)C3=NC2=C1 HLVVITIHAZBPKB-UHFFFAOYSA-N 0.000 description 1
XUPOVMAQJOIDMZ-UHFFFAOYSA-N 9-amino-2,3,3a,4-tetrahydro-1h-cyclopenta[b]quinolin-1-ol Chemical compound N1C2=CC=CC=C2C(N)=C2C1CCC2O XUPOVMAQJOIDMZ-UHFFFAOYSA-N 0.000 description 1
UDVZTVYMAWMTTP-UHFFFAOYSA-N 9-chloro-1,2,3,4-tetrahydroacridin-4-ol Chemical compound C1=CC=C2N=C3C(O)CCCC3=C(Cl)C2=C1 UDVZTVYMAWMTTP-UHFFFAOYSA-N 0.000 description 1
ZGRZYQPIPJVQLD-UHFFFAOYSA-N 9-chloro-10-oxido-1,2,3,4-tetrahydroacridin-10-ium Chemical compound C1=CC=C2[N+]([O-])=C(CCCC3)C3=C(Cl)C2=C1 ZGRZYQPIPJVQLD-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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
239000002841 Lewis acid Substances 0.000 description 1
244000246386 Mentha pulegium Species 0.000 description 1
235000016257 Mentha pulegium Nutrition 0.000 description 1
235000004357 Mentha x piperita Nutrition 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
238000006972 Polonovski rearrangement reaction Methods 0.000 description 1
241000700159 Rattus Species 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
229960004373 acetylcholine Drugs 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000000305 astragalus gummifer gum Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000002051 biphasic effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
229940112822 chewing gum Drugs 0.000 description 1
235000015218 chewing gum Nutrition 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
150000003997 cyclic ketones Chemical class 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000002950 deficient Effects 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000002702 enteric coating Substances 0.000 description 1
238000009505 enteric coating Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000010685 fatty oil Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 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
235000001050 hortel pimenta Nutrition 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000011630 iodine Substances 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
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
125000005905 mesyloxy group Chemical group 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229960001047 methyl salicylate Drugs 0.000 description 1
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
ZZZWGVYBZDIUTE-UHFFFAOYSA-N n'-(2-hydroxy-1,2,3,4-tetrahydroacridin-9-yl)-n,n-dimethylmethanimidamide Chemical compound C1=CC=C2C(N=CN(C)C)=C(CC(O)CC3)C3=NC2=C1 ZZZWGVYBZDIUTE-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000007968 orange flavor Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
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
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
235000012773 waffles Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
- C07D219/10—Nitrogen atoms attached in position 9
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
- C07D219/10—Nitrogen atoms attached in position 9
- C07D219/12—Amino-alkylamino radicals attached in position 9

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Hydrogenated Pyridines (AREA)
Saccharide Compounds (AREA)

DK571989A 1988-11-16 1989-11-15 4-Amino-2,3-alkylen-quinolinderivater, en fremgangsmåde til deres fremstilling og anvendelse til fremstilling af et lægemiddel med aktivitet til lettelse af hukommelses-dysfunktion samt farmaceutisk præparat indeholdende et af de nævnte derivater DK168290B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US27178888A	1988-11-16	1988-11-16
US27178888		1988-11-16

Publications (3)

Publication Number	Publication Date
DK571989D0 DK571989D0 (da)	1989-11-15
DK571989A DK571989A (da)	1990-05-17
DK168290B1 true DK168290B1 (da)	1994-03-07

Family

ID=23037088

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK571989A DK168290B1 (da)	1988-11-16	1989-11-15	4-Amino-2,3-alkylen-quinolinderivater, en fremgangsmåde til deres fremstilling og anvendelse til fremstilling af et lægemiddel med aktivitet til lettelse af hukommelses-dysfunktion samt farmaceutisk præparat indeholdende et af de nævnte derivater

Country Status (15)

Country	Link
EP (1)	EP0369388B1 (fi)
KR (1)	KR0156241B1 (fi)
AT (1)	ATE89553T1 (fi)
CA (1)	CA2003023C (fi)
DE (1)	DE68906647T2 (fi)
DK (1)	DK168290B1 (fi)
ES (1)	ES2054987T3 (fi)
FI (1)	FI90417C (fi)
HU (2)	HU208674B (fi)
IE (1)	IE63038B1 (fi)
IL (1)	IL92307A0 (fi)
NO (1)	NO894547L (fi)
NZ (1)	NZ231376A (fi)
PT (1)	PT92319B (fi)
ZA (1)	ZA898720B (fi)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TW200462B (fi) *	1990-09-27	1993-02-21	Hoechst Roussel Pharma
GB2264707A (en) *	1991-06-18	1993-09-08	Roger Michael Marchbanks	Acridine derivatives for treating alzheimer's disease
US5466696A (en) *	1992-09-10	1995-11-14	Warner Lambert Company	Tacrine and cytochrome P450 oxidase inhibitors and methods of use
US5422350A (en) *	1992-09-10	1995-06-06	Warner-Lambert Company	Nitrogen substituted acridine and cytochrome P450 inhibitors and methods of use
WO2019207604A1 (en) *	2018-04-25	2019-10-31	Rajiv Gandhi Centre For Biotechnology	Tacrine derivatives targeting nmda receptor, acetylcholine esterase, butyryl choline and beta secretase activity

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3582995D1 (de) *	1984-10-25	1991-07-04	Hoechst Roussel Pharma	9-amino-1,2,3,4-tetrahydroacridin-1-ol und verwandte verbindungen, verfahren zu ihrer herstellung und verwendung als arzneimittel.
IL85741A (en) *	1987-03-17	1996-05-14	Hoechst Roussel Pharma	Substituted tetrahydroacridines a process for their preparation and pharmaceutical compositions containing substituted alpha-amino-tetrahydroacridines

1989
- 1989-11-14 NZ NZ231376A patent/NZ231376A/en unknown
- 1989-11-14 KR KR1019890016456A patent/KR0156241B1/ko not_active Expired - Fee Related
- 1989-11-14 DE DE89121037T patent/DE68906647T2/de not_active Expired - Fee Related
- 1989-11-14 AT AT89121037T patent/ATE89553T1/de not_active IP Right Cessation
- 1989-11-14 IL IL92307A patent/IL92307A0/xx unknown
- 1989-11-14 EP EP89121037A patent/EP0369388B1/en not_active Expired - Lifetime
- 1989-11-14 FI FI895416A patent/FI90417C/fi not_active IP Right Cessation
- 1989-11-14 ES ES89121037T patent/ES2054987T3/es not_active Expired - Lifetime
- 1989-11-15 CA CA002003023A patent/CA2003023C/en not_active Expired - Fee Related
- 1989-11-15 IE IE365989A patent/IE63038B1/en not_active IP Right Cessation
- 1989-11-15 ZA ZA898720A patent/ZA898720B/xx unknown
- 1989-11-15 DK DK571989A patent/DK168290B1/da not_active IP Right Cessation
- 1989-11-15 PT PT92319A patent/PT92319B/pt active IP Right Grant
- 1989-11-15 NO NO89894547A patent/NO894547L/no unknown
- 1989-11-16 HU HU593189A patent/HU208674B/hu unknown
1995
- 1995-06-22 HU HU95P/P00336P patent/HU211701A9/hu unknown

Also Published As

Publication number	Publication date
DE68906647T2 (de)	1993-10-07
CA2003023A1 (en)	1990-05-16
DE68906647D1 (de)	1993-06-24
HU895931D0 (en)	1990-02-28
NO894547D0 (no)	1989-11-15
PT92319A (pt)	1990-05-31
DK571989D0 (da)	1989-11-15
ATE89553T1 (de)	1993-06-15
NO894547L (no)	1990-05-18
DK571989A (da)	1990-05-17
ZA898720B (en)	1990-08-29
IE893659L (en)	1990-05-16
IE63038B1 (en)	1995-03-22
CA2003023C (en)	2001-05-29
FI90417B (fi)	1993-10-29
IL92307A0 (en)	1990-07-26
FI895416A0 (fi)	1989-11-14
PT92319B (pt)	1995-08-09
HU211701A9 (en)	1995-12-28
HUT53087A (en)	1990-09-28
HU208674B (en)	1993-12-28
ES2054987T3 (es)	1994-08-16
FI90417C (fi)	1994-02-10
EP0369388B1 (en)	1993-05-19
KR0156241B1 (ko)	1998-11-16
KR900007809A (ko)	1990-06-02
NZ231376A (en)	1992-05-26
EP0369388A1 (en)	1990-05-23

Publication	Publication Date	Title
DK167250B1 (da)	1993-09-27	9-amino-acridinderivater, fremgangsmaade til deres fremstilling, farmaceutiske praeparater deraf og deres anvendelse til fremstilling af laegemidler
US4695573A (en)	1987-09-22	9-amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds
KR100706462B1 (ko)	2007-04-10	시노메닌 및 시노메닌 화합물, 이의 합성 방법 및 용도
KR100255414B1 (ko)	2000-05-01	글루탐산염 수용기 길항근으로서의 삼환 퀴녹살린디온
JP2714536B2 (ja)	1998-02-16	２−（ピペリジン−４−イル，ピリジン−４−イルおよびテトラヒドロピリジン−４−イル）ベンゾフラン−７−オールおよびカルバメート誘導体
FI101297B (fi)	1998-05-29	Menetelmä terapeuttisesti käyttökelpoisten £(N-bentsyylipiperidin-4-yy li)metyyli\|-(tetra- tai heksahydro)asetnaftylen-1-onien tai -olien val mistamiseksi
US5100891A (en)	1992-03-31	Substituted 1,2,3,4-tetrahydrocyclopent[b]indoles, 1,2,3,3a,4,8a-hexahydrocyclopent[B]indoles and related compounds
IL99581A (en)	1995-07-31	Substituted-4-amino-3-pyridinols, a process for their preparation and pharmaceutical compositions containing them
KR100201515B1 (ko)	1999-06-15	1-(치환된 피리디닐아미노)-1에이치-인돌-5-일 치환된 카바메이트, 이의 제조방법 및 이를 포함하는 약제학적 조성물
DK168290B1 (da)	1994-03-07	4-Amino-2,3-alkylen-quinolinderivater, en fremgangsmåde til deres fremstilling og anvendelse til fremstilling af et lægemiddel med aktivitet til lettelse af hukommelses-dysfunktion samt farmaceutisk præparat indeholdende et af de nævnte derivater
IE74907B1 (en)	1997-08-13	1- (Pyrido[3,4-b]-1,4-oxazinyl-4-yl)-1H-indoles intermediates and a process for their preparation and their use as medicaments
EP2861593A1 (en)	2015-04-22	Tricyclic compounds as kat ii inhibitors
DE69201141T2 (de)	1995-05-11	NMDA-Antagonisten.
US4754050A (en)	1988-06-28	9-amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds
KR20200113027A (ko)	2020-10-05	신규 화합물
NO179519B (no)	1996-07-15	Analogifremgangsmåte for fremstilling av 3-(1,2-benzisoksazol-3-yl)-4-pyridinaminer og derivater derav
US4927820A (en)	1990-05-22	Fused heterocyclic derivatives of 1,2,3,4-tetrahydroacridine
US5192789A (en)	1993-03-09	Substituted 1,2,3,4-tetrahydrocyclopent[b]indoles, 1,2,3,3a,4,8a-hexahydrocyclopent[b]indoles and related compounds
AU621416B2 (en)	1992-03-12	Hydroxy-1,2,3,4-tetrahydroaminoacridines, a process for their preparation and their use as medicaments
IL94664A (en)	1994-11-11	4,5,5a,6-tetrahydro-3h-isoxyzolo (5, 4, 3-kl) acridine derivatives, a process for their preparation and pharmaceutical compositions containing them
FR2816619A1 (fr)	2002-05-17	Derives de benzimidazole, leur preparation et leur application en therapeutique
FI90872C (fi)	1994-04-11	Menetelmä terapeuttisesti aktiivisten 1,2,3a,4,5,6-heksahydro/1,3/oksatsino/6,5,4-kl/akridiinijohdannaisten valmistamiseksi
HU209674B (en)	1994-10-28	Apparatus for burning fat, mainly of animal origin

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