NO810776L - Nye 3-klor-kinolin-derivater og deres fremstilling - Google Patents
Nye 3-klor-kinolin-derivater og deres fremstillingInfo
- Publication number
- NO810776L NO810776L NO810776A NO810776A NO810776L NO 810776 L NO810776 L NO 810776L NO 810776 A NO810776 A NO 810776A NO 810776 A NO810776 A NO 810776A NO 810776 L NO810776 L NO 810776L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- carbon atoms
- alkyl
- group
- hydrogen atom
- Prior art date
Links
- 150000005647 3-chloroquinolines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 229940125681 anticonvulsant agent Drugs 0.000 claims description 4
- 239000001961 anticonvulsive agent Substances 0.000 claims description 4
- 150000004678 hydrides Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000003326 hypnotic agent Substances 0.000 claims description 4
- 230000000147 hypnotic effect Effects 0.000 claims description 4
- 150000002475 indoles Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 3
- PFBUKDPBVNJDEW-UHFFFAOYSA-N dichlorocarbene Chemical class Cl[C]Cl PFBUKDPBVNJDEW-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 57
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000000155 melt Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 241000786363 Rhampholeon spectrum Species 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 150000001557 benzodiazepines Chemical class 0.000 description 7
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 7
- 229960003529 diazepam Drugs 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 229940049706 benzodiazepine Drugs 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- CVODZCQCPAYFCL-UHFFFAOYSA-N 2-phenyl-3-(2-piperidin-4-ylethyl)-1h-indole Chemical compound C1CNCCC1CCC(C1=CC=CC=C1N1)=C1C1=CC=CC=C1 CVODZCQCPAYFCL-UHFFFAOYSA-N 0.000 description 3
- MFCNTWPTEPRQDX-UHFFFAOYSA-N 3-(2-piperidin-3-ylethyl)-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1CCC1CCCNC1 MFCNTWPTEPRQDX-UHFFFAOYSA-N 0.000 description 3
- ACGZWTQIIOSSFL-UHFFFAOYSA-N 3-chloro-6-methoxy-4-(2-piperidin-4-ylethyl)quinoline Chemical compound C12=CC(OC)=CC=C2N=CC(Cl)=C1CCC1CCNCC1 ACGZWTQIIOSSFL-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- -1 Lithium aluminum hydride Chemical compound 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IHSUJMKYLPMXNR-UHFFFAOYSA-N 1,3-bis[3-(1h-indol-2-yl)piperidin-3-yl]propan-2-one Chemical compound C1CCNCC1(C=1NC2=CC=CC=C2C=1)CC(=O)CC1(C=2NC3=CC=CC=C3C=2)CCCNC1 IHSUJMKYLPMXNR-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- GYMBONQRGZKLKM-UHFFFAOYSA-N 2-(2-piperidin-4-ylethyl)-1h-indole Chemical compound C=1C2=CC=CC=C2NC=1CCC1CCNCC1 GYMBONQRGZKLKM-UHFFFAOYSA-N 0.000 description 2
- GUXCBXYIRHKLGC-UHFFFAOYSA-N 2-phenyl-3-(2-pyridin-4-ylethyl)-1h-indole Chemical compound C=1C=CC=CC=1C=1NC2=CC=CC=C2C=1CCC1=CC=NC=C1 GUXCBXYIRHKLGC-UHFFFAOYSA-N 0.000 description 2
- IXYYQCYFGTVUBM-UHFFFAOYSA-N 3,6-dichloro-4-(2-piperidin-4-ylethyl)quinoline Chemical compound C12=CC(Cl)=CC=C2N=CC(Cl)=C1CCC1CCNCC1 IXYYQCYFGTVUBM-UHFFFAOYSA-N 0.000 description 2
- LZVMMEZSLWACAE-UHFFFAOYSA-N 3-chloro-2-(2-piperidin-4-ylethyl)quinoline Chemical compound ClC1=CC2=CC=CC=C2N=C1CCC1CCNCC1 LZVMMEZSLWACAE-UHFFFAOYSA-N 0.000 description 2
- FUINNYQDCIKNEO-UHFFFAOYSA-N 3-chloro-2-methyl-4-(2-piperidin-4-ylethyl)quinoline Chemical compound ClC=1C(C)=NC2=CC=CC=C2C=1CCC1CCNCC1 FUINNYQDCIKNEO-UHFFFAOYSA-N 0.000 description 2
- IQIVZMAXIHEQCA-UHFFFAOYSA-N 3-chloro-2-phenyl-4-(2-piperidin-4-ylethyl)quinoline Chemical compound C12=CC=CC=C2N=C(C=2C=CC=CC=2)C(Cl)=C1CCC1CCNCC1 IQIVZMAXIHEQCA-UHFFFAOYSA-N 0.000 description 2
- IGJLTOQNHJAOAG-UHFFFAOYSA-N 3-chloro-4-(2-piperidin-3-ylethyl)quinoline Chemical compound ClC1=CN=C2C=CC=CC2=C1CCC1CCCNC1 IGJLTOQNHJAOAG-UHFFFAOYSA-N 0.000 description 2
- RMGHCRHRCZEWFH-UHFFFAOYSA-N 3-chloro-4-(piperidin-4-ylmethyl)quinoline Chemical compound ClC1=CN=C2C=CC=CC2=C1CC1CCNCC1 RMGHCRHRCZEWFH-UHFFFAOYSA-N 0.000 description 2
- HBQVSPKNMJKKSJ-UHFFFAOYSA-N 3-chloro-6-methoxy-4-(piperidin-4-ylmethyl)quinoline Chemical compound C12=CC(OC)=CC=C2N=CC(Cl)=C1CC1CCNCC1 HBQVSPKNMJKKSJ-UHFFFAOYSA-N 0.000 description 2
- JGUJRMFGADCUKS-UHFFFAOYSA-N 3-chloro-6-methoxy-4-[2-(1-methylpiperidin-4-yl)ethyl]quinoline Chemical compound C12=CC(OC)=CC=C2N=CC(Cl)=C1CCC1CCN(C)CC1 JGUJRMFGADCUKS-UHFFFAOYSA-N 0.000 description 2
- PFSJTEXPGBUCNF-UHFFFAOYSA-N 3-chloro-8-methyl-4-(piperidin-4-ylmethyl)quinoline Chemical compound ClC1=CN=C2C(C)=CC=CC2=C1CC1CCNCC1 PFSJTEXPGBUCNF-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- WESPSDKPPIZUFI-UHFFFAOYSA-N ethyl 4-[2-(3-chloro-6-methoxyquinolin-4-yl)ethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1CCC1=C(Cl)C=NC2=CC=C(OC)C=C12 WESPSDKPPIZUFI-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- SADQVAVFGNTEOD-UHFFFAOYSA-N indalpine Chemical compound C=1NC2=CC=CC=C2C=1CCC1CCNCC1 SADQVAVFGNTEOD-UHFFFAOYSA-N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- HKYWCJOLDLYIOL-UHFFFAOYSA-N 3-(piperidin-4-ylmethyl)-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1CC1CCNCC1 HKYWCJOLDLYIOL-UHFFFAOYSA-N 0.000 description 1
- TVVBVVALCFSDHR-UHFFFAOYSA-N 3-chloro-4-(2-piperidin-4-ylethyl)quinoline Chemical compound ClC1=CN=C2C=CC=CC2=C1CCC1CCNCC1 TVVBVVALCFSDHR-UHFFFAOYSA-N 0.000 description 1
- VBTGJRLNPIVUSE-UHFFFAOYSA-N 5-chloro-3-(2-piperidin-4-ylethyl)-1h-indole Chemical compound C12=CC(Cl)=CC=C2NC=C1CCC1CCNCC1 VBTGJRLNPIVUSE-UHFFFAOYSA-N 0.000 description 1
- IIKBAURXMKGMGY-UHFFFAOYSA-N 5-methoxy-3-(2-piperidin-4-ylethyl)-1h-indole Chemical compound C12=CC(OC)=CC=C2NC=C1CCC1CCNCC1 IIKBAURXMKGMGY-UHFFFAOYSA-N 0.000 description 1
- GAVVCINZHZDZIS-UHFFFAOYSA-N 7-methyl-3-(piperidin-4-ylmethyl)-1h-indole Chemical compound C=1NC=2C(C)=CC=CC=2C=1CC1CCNCC1 GAVVCINZHZDZIS-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- DOAYJPJLHNHQSU-UHFFFAOYSA-N aluminum;lithium;hydrate Chemical compound [Li].O.[Al] DOAYJPJLHNHQSU-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UPBWIICFGYMCPC-UHFFFAOYSA-N bis(2-methoxyethoxy)aluminum Chemical compound COCCO[Al]OCCOC UPBWIICFGYMCPC-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- YALYLPKSKBQFJP-UHFFFAOYSA-N chloroform;n-ethylethanamine Chemical compound ClC(Cl)Cl.CCNCC YALYLPKSKBQFJP-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002996 emotional effect Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Anesthesiology (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8005152A FR2477544A1 (fr) | 1980-03-07 | 1980-03-07 | Nouveaux derives de la chloro-3 quinoleine, procedes pour leur preparation, et leur utilisation comme medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO810776L true NO810776L (no) | 1981-09-08 |
Family
ID=9239431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO810776A NO810776L (no) | 1980-03-07 | 1981-03-06 | Nye 3-klor-kinolin-derivater og deres fremstilling |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US4405789A (ja) |
| EP (1) | EP0035925B1 (ja) |
| JP (1) | JPS56139482A (ja) |
| AT (1) | AT376217B (ja) |
| AU (1) | AU540680B2 (ja) |
| CA (1) | CA1167444A (ja) |
| DE (1) | DE3167536D1 (ja) |
| DK (1) | DK101481A (ja) |
| FR (1) | FR2477544A1 (ja) |
| NO (1) | NO810776L (ja) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2495470A1 (fr) * | 1980-12-05 | 1982-06-11 | Pharmindustrie | Nouveaux medicaments a base de derives de (quinolyl-4)-1 (piperidyl-4)-2 ethanol ou (quinolyl-4)-1 (piperidyl-4)-3 propanol |
| US5240942A (en) * | 1990-07-10 | 1993-08-31 | Adir Et Compagnie | Piperidine, tetrahydropyridine and pyrrolidine compounds |
| CA2092112A1 (en) * | 1992-03-23 | 1993-09-24 | Nobuyoshi Iwata | Indole and indazole derivatives, for the treatment and prophylaxis of cerebral disorders, their preparation and their use |
| EP1907384A2 (en) * | 2005-06-30 | 2008-04-09 | Prosidion Limited | Gpcr agonists |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2354771A1 (fr) * | 1976-06-18 | 1978-01-13 | Mar Pha Etu Expl Marques | ((quinolyl-4)-3 propyl-1) -4 piperidines, leur preparation et leur utilisation comme medicaments |
-
1980
- 1980-03-07 FR FR8005152A patent/FR2477544A1/fr active Granted
-
1981
- 1981-02-11 AT AT0063381A patent/AT376217B/de not_active IP Right Cessation
- 1981-02-24 US US06/237,784 patent/US4405789A/en not_active Expired - Fee Related
- 1981-02-24 DE DE8181400283T patent/DE3167536D1/de not_active Expired
- 1981-02-24 EP EP81400283A patent/EP0035925B1/fr not_active Expired
- 1981-03-05 CA CA000372413A patent/CA1167444A/fr not_active Expired
- 1981-03-06 JP JP3237081A patent/JPS56139482A/ja active Pending
- 1981-03-06 NO NO810776A patent/NO810776L/no unknown
- 1981-03-06 DK DK101481A patent/DK101481A/da not_active Application Discontinuation
- 1981-03-06 AU AU68143/81A patent/AU540680B2/en not_active Expired - Fee Related
-
1982
- 1982-09-29 US US06/426,543 patent/US4493838A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0035925B1 (fr) | 1984-12-05 |
| DK101481A (da) | 1981-09-08 |
| AU6814381A (en) | 1981-09-10 |
| CA1167444A (fr) | 1984-05-15 |
| ATA63381A (de) | 1984-03-15 |
| JPS56139482A (en) | 1981-10-30 |
| FR2477544B1 (ja) | 1983-10-21 |
| US4493838A (en) | 1985-01-15 |
| AT376217B (de) | 1984-10-25 |
| US4405789A (en) | 1983-09-20 |
| EP0035925A1 (fr) | 1981-09-16 |
| FR2477544A1 (fr) | 1981-09-11 |
| AU540680B2 (en) | 1984-11-29 |
| DE3167536D1 (en) | 1985-01-17 |
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