NO812105L - Nye derivater av 1-(2-,3- eller 4-kinolyl)-2- eller -3-(2- eller 3-piperidyl eller -pyrrolidinyl) etanon eller propanon, samt deres fremstilling og anvendelse - Google Patents

Nye derivater av 1-(2-,3- eller 4-kinolyl)-2- eller -3-(2- eller 3-piperidyl eller -pyrrolidinyl) etanon eller propanon, samt deres fremstilling og anvendelse

Info

Publication number: NO812105L
Authority: NO; Norway
Prior art keywords: group; formula; piperidyl; ethyl; quinoline
Prior art date: 1980-06-20

Application number

NO812105A

Other languages

English (en)

Norwegian (no)

Inventor

Marie-Christine Dubroeucq

Claude Gueremy

Gerard Le Fur

Jacques Mizoule

Original Assignee

Pharmindustrie

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.)

1980-06-20

Filing date

1981-06-19

Publication date

1981-12-21

1981-06-19 Application filed by Pharmindustrie filed Critical Pharmindustrie

1981-12-21 Publication of NO812105L publication Critical patent/NO812105L/no

Links

238000002360 preparation method Methods 0.000 title claims description 25
-1 4-CHINOLYL Chemical class 0.000 title claims description 23
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 title description 48
150000001875 compounds Chemical class 0.000 claims description 74
125000000217 alkyl group Chemical group 0.000 claims description 29
238000000034 method Methods 0.000 claims description 25
125000004432 carbon atom Chemical group C* 0.000 claims description 23
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
125000003710 aryl alkyl group Chemical group 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
239000011707 mineral Substances 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
150000004678 hydrides Chemical class 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 6
230000003288 anthiarrhythmic effect Effects 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 6
239000002184 metal Substances 0.000 claims description 6
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
208000019901 Anxiety disease Diseases 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
229940079593 drug Drugs 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
239000002168 alkylating agent Substances 0.000 claims description 4
229940100198 alkylating agent Drugs 0.000 claims description 4
239000001961 anticonvulsive agent Substances 0.000 claims description 4
235000019253 formic acid Nutrition 0.000 claims description 4
230000000147 hypnotic effect Effects 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
150000001412 amines Chemical group 0.000 claims description 3
239000003416 antiarrhythmic agent Substances 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims description 3
150000003248 quinolines Chemical class 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
150000003222 pyridines Chemical class 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims 2
125000004429 atom Chemical group 0.000 claims 2
235000005985 organic acids Nutrition 0.000 claims 2
230000001773 anti-convulsant effect Effects 0.000 claims 1
229960003965 antiepileptics Drugs 0.000 claims 1
239000007859 condensation product Substances 0.000 claims 1
239000000203 mixture Substances 0.000 description 85
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 82
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 76
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 55
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 54
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 51
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
239000000243 solution Substances 0.000 description 42
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 34
239000000047 product Substances 0.000 description 33
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 30
125000005493 quinolyl group Chemical group 0.000 description 30
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 30
239000000155 melt Substances 0.000 description 28
125000005936 piperidyl group Chemical group 0.000 description 28
229910052943 magnesium sulfate Inorganic materials 0.000 description 27
235000019341 magnesium sulphate Nutrition 0.000 description 27
239000000377 silicon dioxide Substances 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 22
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
239000003921 oil Substances 0.000 description 21
239000012074 organic phase Substances 0.000 description 21
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 18
239000007864 aqueous solution Substances 0.000 description 18
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 18
235000012239 silicon dioxide Nutrition 0.000 description 18
239000000725 suspension Substances 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
239000002904 solvent Substances 0.000 description 17
239000012442 inert solvent Substances 0.000 description 15
239000008188 pellet Substances 0.000 description 14
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 14
229910000105 potassium hydride Inorganic materials 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 13
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000012043 crude product Substances 0.000 description 12
238000010828 elution Methods 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
239000002585 base Substances 0.000 description 11
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 10
FSEXLNMNADBYJU-UHFFFAOYSA-N alpha-Phenylquinoline Natural products C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 9
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 8
BRSGIGKMAFNWJD-UHFFFAOYSA-N 2-phenyl-4-(2-piperidin-3-ylethyl)quinoline Chemical compound C1CCNCC1CCC(C1=CC=CC=C1N=1)=CC=1C1=CC=CC=C1 BRSGIGKMAFNWJD-UHFFFAOYSA-N 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
241000786363 Rhampholeon spectrum Species 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 8
238000009835 boiling Methods 0.000 description 8
239000012429 reaction media Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
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 7
239000003054 catalyst Substances 0.000 description 7
238000004821 distillation Methods 0.000 description 7
XFSBVAOIAHNAPC-XTHSEXKGSA-N 16-Ethyl-1alpha,6alpha,19beta-trimethoxy-4-(methoxymethyl)-aconitane-3alpha,8,10alpha,11,18alpha-pentol, 8-acetate 10-benzoate Chemical compound O([C@H]1[C@]2(O)C[C@H]3[C@@]45C6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)[C@@H]4[C@]([C@@H](C[C@@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-XTHSEXKGSA-N 0.000 description 6
XFSBVAOIAHNAPC-UHFFFAOYSA-N Aconitin Natural products CCN1CC(C(CC2OC)O)(COC)C3C(OC)C(C(C45)(OC(C)=O)C(O)C6OC)C1C32C4CC6(O)C5OC(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
229940039750 aconitine Drugs 0.000 description 6
STDXGNLCJACLFY-UHFFFAOYSA-N aconitine Natural products CCN1CC2(COC)C(O)CC(O)C34C5CC6(O)C(OC)C(O)C(OC(=O)C)(C5C6OC(=O)c7ccccc7)C(C(OC)C23)C14 STDXGNLCJACLFY-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
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 6
229960003529 diazepam Drugs 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
238000001914 filtration Methods 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
235000010755 mineral Nutrition 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 5
239000012071 phase Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
241001465754 Metazoa Species 0.000 description 4
241000700159 Rattus Species 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
229940049706 benzodiazepine Drugs 0.000 description 4
150000001557 benzodiazepines Chemical class 0.000 description 4
238000010908 decantation Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 4
CDSWNSHBEGGCMN-UHFFFAOYSA-N 2-(1-tritylpiperidin-2-yl)ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCC1N(C(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)CCCC1 CDSWNSHBEGGCMN-UHFFFAOYSA-N 0.000 description 3
CFLWTTGQHKSIDT-UHFFFAOYSA-N 2-phenyl-4-(2-piperidin-2-ylethyl)quinoline Chemical compound C1CCCNC1CCC(C1=CC=CC=C1N=1)=CC=1C1=CC=CC=C1 CFLWTTGQHKSIDT-UHFFFAOYSA-N 0.000 description 3
QCTPETPQTGSCSP-UHFFFAOYSA-N 2-phenyl-4-(2-pyridin-2-ylethyl)quinoline Chemical compound C=1C=CC=NC=1CCC(C1=CC=CC=C1N=1)=CC=1C1=CC=CC=C1 QCTPETPQTGSCSP-UHFFFAOYSA-N 0.000 description 3
URNNGNMAXZKPQD-UHFFFAOYSA-N 2-phenyl-4-(3-piperidin-3-ylpropyl)quinoline Chemical compound C=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1CCCC1CCCNC1 URNNGNMAXZKPQD-UHFFFAOYSA-N 0.000 description 3
KEFFBQARWJSKAJ-UHFFFAOYSA-N 2-pyridin-2-yl-1-quinolin-4-ylethanone Chemical compound C=1C=NC2=CC=CC=C2C=1C(=O)CC1=CC=CC=N1 KEFFBQARWJSKAJ-UHFFFAOYSA-N 0.000 description 3
VALTUHGPGRQWMC-UHFFFAOYSA-N 3-piperidin-3-yl-1-quinolin-2-ylpropan-1-one Chemical compound C=1C=C2C=CC=CC2=NC=1C(=O)CCC1CCCNC1 VALTUHGPGRQWMC-UHFFFAOYSA-N 0.000 description 3
HWZNRSJEUMDBKT-UHFFFAOYSA-N 3-piperidin-3-yl-1-quinolin-3-ylpropan-1-one Chemical compound C=1N=C2C=CC=CC2=CC=1C(=O)CCC1CCCNC1 HWZNRSJEUMDBKT-UHFFFAOYSA-N 0.000 description 3
DVUVCZHCYIUJQN-UHFFFAOYSA-N 3-piperidin-3-yl-1-quinolin-4-ylpropan-1-one Chemical compound C=1C=NC2=CC=CC=C2C=1C(=O)CCC1CCCNC1 DVUVCZHCYIUJQN-UHFFFAOYSA-N 0.000 description 3
RQDPDTKHYBQJHF-UHFFFAOYSA-N 4-(2-piperidin-2-ylethyl)quinoline Chemical compound C=1C=NC2=CC=CC=C2C=1CCC1CCCCN1 RQDPDTKHYBQJHF-UHFFFAOYSA-N 0.000 description 3
GANNOMARIJLFDZ-UHFFFAOYSA-N 4-(2-pyridin-2-ylethyl)quinoline Chemical compound C=1C=NC2=CC=CC=C2C=1CCC1=CC=CC=N1 GANNOMARIJLFDZ-UHFFFAOYSA-N 0.000 description 3
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
229940043279 diisopropylamine Drugs 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
239000003326 hypnotic agent Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000002609 medium Substances 0.000 description 3
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
230000010412 perfusion Effects 0.000 description 3
229910003446 platinum oxide Inorganic materials 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
OXPUEGWGIADGJY-UHFFFAOYSA-N 2-(3-piperidin-3-ylpropyl)quinoline Chemical compound C=1C=C2C=CC=CC2=NC=1CCCC1CCCNC1 OXPUEGWGIADGJY-UHFFFAOYSA-N 0.000 description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
WMATYSKXRRXYOW-UHFFFAOYSA-N 2-phenyl-4-(2-piperidin-3-ylethyl)quinoline;hydrochloride Chemical compound Cl.C1CCNCC1CCC(C1=CC=CC=C1N=1)=CC=1C1=CC=CC=C1 WMATYSKXRRXYOW-UHFFFAOYSA-N 0.000 description 2
ZQUSDIDSUYQGMZ-UHFFFAOYSA-N 2-phenyl-4-(2-pyrrolidin-3-ylethyl)quinoline Chemical compound C1CNCC1CCC(C1=CC=CC=C1N=1)=CC=1C1=CC=CC=C1 ZQUSDIDSUYQGMZ-UHFFFAOYSA-N 0.000 description 2
XLIHTECBVOWLKH-UHFFFAOYSA-N 2-phenyl-4-(3-piperidin-2-ylpropyl)quinoline Chemical compound C=1C(C=2C=CC=CC=2)=NC2=CC=CC=C2C=1CCCC1CCCCN1 XLIHTECBVOWLKH-UHFFFAOYSA-N 0.000 description 2
BGDLZXXUILEDNM-UHFFFAOYSA-N 3-(3-piperidin-3-ylpropyl)quinoline Chemical compound C=1N=C2C=CC=CC2=CC=1CCCC1CCCNC1 BGDLZXXUILEDNM-UHFFFAOYSA-N 0.000 description 2
QRHYNKDUDYICET-UHFFFAOYSA-N 4-(2-piperidin-3-ylethyl)-2-[3-(trifluoromethyl)phenyl]quinoline Chemical compound FC(F)(F)C1=CC=CC(C=2N=C3C=CC=CC3=C(CCC3CNCCC3)C=2)=C1 QRHYNKDUDYICET-UHFFFAOYSA-N 0.000 description 2
CFWMLCVZWORYIH-UHFFFAOYSA-N 6-chloro-2-phenyl-4-(2-piperidin-3-ylethyl)quinoline Chemical compound C12=CC(Cl)=CC=C2N=C(C=2C=CC=CC=2)C=C1CCC1CCCNC1 CFWMLCVZWORYIH-UHFFFAOYSA-N 0.000 description 2
FMRBDPUZUYZQSU-UHFFFAOYSA-N 6-methoxy-4-(2-piperidin-3-ylethyl)quinoline Chemical compound C12=CC(OC)=CC=C2N=CC=C1CCC1CCCNC1 FMRBDPUZUYZQSU-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
229940125681 anticonvulsant agent Drugs 0.000 description 2
230000036506 anxiety Effects 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
238000006480 benzoylation reaction Methods 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
239000003638 chemical reducing agent Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
230000000694 effects Effects 0.000 description 2
FJWYVZDPWAPMGN-UHFFFAOYSA-N ethyl quinoline-4-carboxylate Chemical compound C1=CC=C2C(C(=O)OCC)=CC=NC2=C1 FJWYVZDPWAPMGN-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
150000002641 lithium Chemical class 0.000 description 2
238000006053 organic reaction Methods 0.000 description 2
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 2
230000008929 regeneration Effects 0.000 description 2
238000011069 regeneration method Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
PAORVUMOXXAMPL-VIFPVBQESA-N (2r)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl chloride Chemical compound CO[C@@](C(Cl)=O)(C(F)(F)F)C1=CC=CC=C1 PAORVUMOXXAMPL-VIFPVBQESA-N 0.000 description 1
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
WMOCATMBSRXCTN-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-(2-piperidin-3-ylethyl)quinoline Chemical compound C1=CC(Cl)=CC=C1C1=CC(CCC2CNCCC2)=C(C=CC=C2)C2=N1 WMOCATMBSRXCTN-UHFFFAOYSA-N 0.000 description 1
GXFBUBKTTCNIRT-UHFFFAOYSA-N 2-(4-chlorophenyl)quinoline Chemical compound C1=CC(Cl)=CC=C1C1=CC=C(C=CC=C2)C2=N1 GXFBUBKTTCNIRT-UHFFFAOYSA-N 0.000 description 1
VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
RUABRRCEELGMQH-UHFFFAOYSA-N 2-piperidin-3-ylacetaldehyde Chemical compound O=CCC1CCCNC1 RUABRRCEELGMQH-UHFFFAOYSA-N 0.000 description 1
YQZGQXPHGLAEHA-UHFFFAOYSA-N 2-pyridin-2-ylquinoline Chemical compound N1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 YQZGQXPHGLAEHA-UHFFFAOYSA-N 0.000 description 1
XAVCWNGDMHAGKP-UHFFFAOYSA-N 2-pyridin-3-ylquinoline Chemical compound C1=CC2=CC=CC=C2N=C1C1=CC=CN=C1 XAVCWNGDMHAGKP-UHFFFAOYSA-N 0.000 description 1
PAORVUMOXXAMPL-UHFFFAOYSA-N 3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl chloride Chemical compound COC(C(Cl)=O)(C(F)(F)F)C1=CC=CC=C1 PAORVUMOXXAMPL-UHFFFAOYSA-N 0.000 description 1
GKNVIMPWWNFDOX-UHFFFAOYSA-N 3-fluoro-2-phenylpropanoyl chloride Chemical compound FCC(C(=O)Cl)C1=CC=CC=C1 GKNVIMPWWNFDOX-UHFFFAOYSA-N 0.000 description 1
PXSMRCDTPWJQMY-UHFFFAOYSA-N 4-(3-piperidin-3-ylpropyl)quinoline Chemical compound C=1C=NC2=CC=CC=C2C=1CCCC1CCCNC1 PXSMRCDTPWJQMY-UHFFFAOYSA-N 0.000 description 1
FZCMQWDMUOSOLN-UHFFFAOYSA-N 6-methoxy-4-(3-piperidin-3-ylpropyl)quinoline Chemical compound C12=CC(OC)=CC=C2N=CC=C1CCCC1CCCNC1 FZCMQWDMUOSOLN-UHFFFAOYSA-N 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
102100025854 Acyl-coenzyme A thioesterase 1 Human genes 0.000 description 1
101710175445 Acyl-coenzyme A thioesterase 1 Proteins 0.000 description 1
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000854350 Enicospilus group Species 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 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
238000006547 Leuckart Thiophenol synthesis reaction Methods 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
206010047281 Ventricular arrhythmia Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 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
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
230000006793 arrhythmia Effects 0.000 description 1
125000005228 aryl sulfonate group Chemical group 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000007891 compressed tablet Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
239000013078 crystal Substances 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
238000006114 decarboxylation reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000001934 delay Effects 0.000 description 1
238000010586 diagram Methods 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000002996 emotional effect Effects 0.000 description 1
RJFIWCWTENIBKC-UHFFFAOYSA-N ethyl 2-piperidin-3-ylacetate Chemical compound CCOC(=O)CC1CCCNC1 RJFIWCWTENIBKC-UHFFFAOYSA-N 0.000 description 1
DPBSXYRJZFUOIL-UHFFFAOYSA-N ethyl 3-piperidin-3-ylpropanoate Chemical compound CCOC(=O)CCC1CCCNC1 DPBSXYRJZFUOIL-UHFFFAOYSA-N 0.000 description 1
AMTCPYGXTNRQQZ-UHFFFAOYSA-N ethyl 6-methoxyquinoline-4-carboxylate Chemical compound C1=C(OC)C=C2C(C(=O)OCC)=CC=NC2=C1 AMTCPYGXTNRQQZ-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
PWOYTBYNBYNZCO-UHFFFAOYSA-N ethyl quinoline-2-carboxylate Chemical compound C1=CC=CC2=NC(C(=O)OCC)=CC=C21 PWOYTBYNBYNZCO-UHFFFAOYSA-N 0.000 description 1
OTTDACPMYLDVTL-UHFFFAOYSA-N ethyl quinoline-3-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)OCC)=CN=C21 OTTDACPMYLDVTL-UHFFFAOYSA-N 0.000 description 1
OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000006698 induction Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
QKONQSPVWNDJJQ-UHFFFAOYSA-N methyl 2-pyrrolidin-3-ylacetate Chemical compound COC(=O)CC1CCNC1 QKONQSPVWNDJJQ-UHFFFAOYSA-N 0.000 description 1
210000005164 penile vein Anatomy 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
239000006187 pill Substances 0.000 description 1
HAGVWBQWCRHRRA-UHFFFAOYSA-N piperidin-1-yl acetate Chemical compound CC(=O)ON1CCCCC1 HAGVWBQWCRHRRA-UHFFFAOYSA-N 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
230000007017 scission Effects 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride 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
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
230000000392 somatic effect Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
150000003512 tertiary amines Chemical class 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
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
239000002966 varnish Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen 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
- 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
- A61P9/06—Antiarrhythmics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Anesthesiology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)

NO812105A 1980-06-20 1981-06-19 Nye derivater av 1-(2-,3- eller 4-kinolyl)-2- eller -3-(2- eller 3-piperidyl eller -pyrrolidinyl) etanon eller propanon, samt deres fremstilling og anvendelse NO812105L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8013698A FR2485014A1 (fr)	1980-06-20	1980-06-20	Nouveaux derives de (quinolyl-2, -3 ou -4)-1 (piperidyl ou pyrrolidinyl-2 ou -3)-2 ou -3 ethanone ou propanone, procedes pour leur preparation, et leur utilisation comme medicaments

Publications (1)

Publication Number	Publication Date
NO812105L true NO812105L (no)	1981-12-21

Family

ID=9243305

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO812105A NO812105L (no)	1980-06-20	1981-06-19	Nye derivater av 1-(2-,3- eller 4-kinolyl)-2- eller -3-(2- eller 3-piperidyl eller -pyrrolidinyl) etanon eller propanon, samt deres fremstilling og anvendelse

Country Status (16)

Country	Link
US (1)	US4402961A (es)
EP (1)	EP0042781B1 (es)
JP (1)	JPS57102885A (es)
AR (1)	AR227731A1 (es)
AU (1)	AU537379B2 (es)
CA (1)	CA1184180A (es)
DE (1)	DE3169169D1 (es)
DK (1)	DK271981A (es)
ES (3)	ES503166A0 (es)
FR (1)	FR2485014A1 (es)
GR (1)	GR75685B (es)
IL (1)	IL63125A0 (es)
MA (1)	MA19184A1 (es)
NO (1)	NO812105L (es)
PT (1)	PT73232B (es)
ZA (1)	ZA814126B (es)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2471981A1 (fr) *	1979-12-21	1981-06-26	Pharmindustrie	Nouveaux derives de la (piperidyl-4)-2 (quinolyl-4)-1 ethanone, produits intermediaires et procedes pour leur preparation, et leur utilisation comme medicaments
IL62240A0 (en) *	1980-03-06	1981-05-20	Acf Chemiefarma Nv	Novel quinoline derivatives,pharmaceutical compositions containing such compounds,and methods for the preparation of these compounds
GR74482B (es) *	1980-03-06	1984-06-28	Acf Chemiefarma Nv
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
FR2525595A1 (fr) *	1982-04-27	1983-10-28	Pharmuka Lab	Nouveaux derives d'arene et d'heteroarenecarboxamides et leur utilisation comme medicaments
US4560692A (en) *	1984-07-18	1985-12-24	Hoffmann-La Roche Inc.	4-Piperidino-2-phenylquinolines
FR2582514B1 (fr) *	1985-05-30	1988-02-19	Rhone Poulenc Sante	Medicaments a base d'amides, nouveaux amides et leur preparation
FR2664592B1 (fr) *	1990-07-10	1994-09-02	Adir	Nouveaux derives de la piperidine, de la tetrahydropyridine et de la pyrrolidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
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1980
- 1980-06-20 FR FR8013698A patent/FR2485014A1/fr active Granted
1981
- 1981-06-04 GR GR65156A patent/GR75685B/el unknown
- 1981-06-09 US US06/271,877 patent/US4402961A/en not_active Expired - Fee Related
- 1981-06-12 DE DE8181400934T patent/DE3169169D1/de not_active Expired
- 1981-06-12 EP EP81400934A patent/EP0042781B1/fr not_active Expired
- 1981-06-17 ES ES503166A patent/ES503166A0/es active Granted
- 1981-06-17 PT PT73232A patent/PT73232B/pt unknown
- 1981-06-17 CA CA000380003A patent/CA1184180A/fr not_active Expired
- 1981-06-18 ZA ZA814126A patent/ZA814126B/xx unknown
- 1981-06-18 IL IL63125A patent/IL63125A0/xx unknown
- 1981-06-19 JP JP56095167A patent/JPS57102885A/ja active Pending
- 1981-06-19 NO NO812105A patent/NO812105L/no unknown
- 1981-06-19 DK DK271981A patent/DK271981A/da not_active Application Discontinuation
- 1981-06-19 MA MA19394A patent/MA19184A1/fr unknown
- 1981-06-19 AU AU71983/81A patent/AU537379B2/en not_active Ceased
1982
- 1982-01-01 AR AR22773182D patent/AR227731A1/es active
- 1982-06-25 ES ES513449A patent/ES513449A0/es active Granted
- 1982-06-25 ES ES513448A patent/ES8305353A1/es not_active Expired

Also Published As

Publication number	Publication date
ES513448A0 (es)	1983-04-01
FR2485014B1 (es)	1984-05-04
EP0042781B1 (fr)	1985-03-06
IL63125A0 (en)	1981-09-13
MA19184A1 (fr)	1981-12-31
ES8300748A1 (es)	1982-11-01
DE3169169D1 (en)	1985-04-11
ZA814126B (en)	1982-06-30
FR2485014A1 (fr)	1981-12-24
DK271981A (da)	1981-12-21
AR227731A1 (es)	1982-11-30
CA1184180A (fr)	1985-03-19
PT73232B (fr)	1982-07-30
AU7198381A (en)	1981-12-24
GR75685B (es)	1984-08-02
US4402961A (en)	1983-09-06
ES8305354A1 (es)	1983-04-01
PT73232A (fr)	1981-07-01
ES503166A0 (es)	1982-11-01
ES8305353A1 (es)	1983-04-01
JPS57102885A (en)	1982-06-26
EP0042781A1 (fr)	1981-12-30
ES513449A0 (es)	1983-04-01
AU537379B2 (en)	1984-06-21

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NO812105L (no)	1981-12-21	Nye derivater av 1-(2-,3- eller 4-kinolyl)-2- eller -3-(2- eller 3-piperidyl eller -pyrrolidinyl) etanon eller propanon, samt deres fremstilling og anvendelse
US6498168B2 (en)	2002-12-24	Muscarinic antagonists
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US5214055A (en)	1993-05-25	Aminopiperidine 4-oxo-4H-chromen-2-yl compounds
US4711890A (en)	1987-12-08	Pharmaceutical compositions containing azanaphthalene-carboxamide derivatives, azanaphthalene-carboxamide derivatives and process for their use
JPH06340620A (ja)	1994-12-13	新規なアミノピペリジン、アミノピロリジンおよびアミノパーヒドロアゼピン化合物
NO329065B1 (no)	2010-08-09	Derivater av N-[fenyl(piperidin-2yl)metyl]benzamid og anvendelse av de samme i terapeutika
JP2007508358A (ja)	2007-04-05	Ｎ−［フェニル（ピペリジン−２−イル）メチル］ベンズアミド誘導体、この調製方法およびこの治療法における使用
NO851393L (no)	1985-10-10	Fremgangsmaate for fremstilling av n-aryl-n-(4-piperidinyl)amider.
NO831466L (no)	1983-10-28	Nye derivater av aren- og heteroaren-karboksamider
HU195804B (en)	1988-07-28	Process for preparing piperidine derivatives and medical compositions containing them
US4433150A (en)	1984-02-21	2-(4-Piperidyl)-1-(4-quinolyl)-ethanones and ethanes
EA010051B1 (ru)	2008-06-30	Соединения инданилпиперазина, способ их получения и содержащие их фармацевтические композиции
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DK155793B (da)	1989-05-16	Analogifremgangsmaade til fremstilling af 3-substituerede pyrrolidiner eller piperidiner samt 3-substituerede pyrrolidiner eller piperidiner til brug som udgangsmateriale ved fremgangsmaaden
DE69007126T2 (de)	1994-06-01	Muscarin-rezeptor-antagonisten.
NO174553B (no)	1994-02-14	Analogifremgangsmaate for fremstilling av terapeutisk aktiv 4-hete ropentacyklisk-4-(N-(fenyl)amido)piperidinderivat
CA2072520A1 (en)	1992-12-28	2-(1-piperidyl) ethanol derivatives, their preparation and their therapeutic application
NO159532B (no)	1988-10-03	Analogifremgangsmaate for fremstilling av terapeutisk aktive derivater av 1-(4-kinolyl)-2-(4-piperidyl)-etanol eller1-(4-kinolyl)-3-(4-piperidyl)-propanol.
US4411904A (en)	1983-10-25	Diphenylpropanamines, compositions thereof and use thereof
EP0506903A1 (en)	1992-10-07	4-acetoxy-piperidine derivatives, process for their preparation and use as a muscarinic m3-receptor antagonist
US4405789A (en)	1983-09-20	2 Phenyl-3-chloro-4[piperidyl alkyl]quinolines
FI97541B (fi)	1996-09-30	Menetelmä uusien terapeuttisesti käyttökelpoisten N-difenyylialkyylialkoksisubstituoitujen 3-piperidiinikarboksyylihappojohdannaisten valmistamiseksi
DK150477B (da)	1987-03-09	Analogifremgangsmaade til fremstilling af 4-(4-(naphthalenyloxy)-1-piperidinyl)-1-phenyl-1-butanonderivater og mellemprodukter til brug ved fremgangsmaaden
US4364954A (en)	1982-12-21	Diphenylpropanamines, compositions thereof and use thereof