FI79314C - Foerfarande foer framstaellning av terapeutiskt anvaendbara 2-fenyl-imidazo/1,2-a/kinolin-1-acetamider. - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara 2-fenyl-imidazo/1,2-a/kinolin-1-acetamider. Download PDFInfo
- Publication number
- FI79314C FI79314C FI853027A FI853027A FI79314C FI 79314 C FI79314 C FI 79314C FI 853027 A FI853027 A FI 853027A FI 853027 A FI853027 A FI 853027A FI 79314 C FI79314 C FI 79314C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- compound
- methyl
- quinoline
- give
- Prior art date
Links
- -1 2-Phenyl-imidazo [1,2-a] quinoline-1-acetamides Chemical class 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 65
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- GCMNJUJAKQGROZ-UHFFFAOYSA-N 1,2-Dihydroquinolin-2-imine Chemical compound C1=CC=CC2=NC(N)=CC=C21 GCMNJUJAKQGROZ-UHFFFAOYSA-N 0.000 claims description 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 150000002825 nitriles Chemical class 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 4
- 239000005695 Ammonium acetate Substances 0.000 claims description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 4
- 229940043376 ammonium acetate Drugs 0.000 claims description 4
- 235000019257 ammonium acetate Nutrition 0.000 claims description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000005936 piperidyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000008040 ionic compounds Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 claims 2
- 229940125810 compound 20 Drugs 0.000 claims 1
- 108010041382 compound 20 Proteins 0.000 claims 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 241001465754 Metazoa Species 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 230000000694 effects Effects 0.000 description 14
- 238000002474 experimental method Methods 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 241000700159 Rattus Species 0.000 description 12
- 125000001309 chloro group Chemical group Cl* 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 230000007958 sleep Effects 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 206010010904 Convulsion Diseases 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 230000000949 anxiolytic effect Effects 0.000 description 5
- 230000001624 sedative effect Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000002249 anxiolytic agent Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 229940005530 anxiolytics Drugs 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 230000000147 hypnotic effect Effects 0.000 description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000035939 shock Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- GXFZCDMWGMFGFL-KKXMJGKMSA-N (+)-Tubocurarine chloride hydrochloride Chemical compound [Cl-].[Cl-].C([C@H]1[N+](C)(C)CCC=2C=C(C(=C(OC3=CC=C(C=C3)C[C@H]3C=4C=C(C(=CC=4CC[NH+]3C)OC)O3)C=21)O)OC)C1=CC=C(O)C3=C1 GXFZCDMWGMFGFL-KKXMJGKMSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 241001111317 Chondrodendron tomentosum Species 0.000 description 2
- 239000008709 Curare Substances 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
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000003651 drinking water Substances 0.000 description 2
- 235000020188 drinking water Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 description 2
- HJMONQQZFQKQPS-UHFFFAOYSA-N imidazo[1,2-a]quinoline Chemical class C1=CC=C2N3C=CN=C3C=CC2=C1 HJMONQQZFQKQPS-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical compound C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 description 1
- GUCOHALGSMFJNM-UHFFFAOYSA-N 2-(2h-quinolin-1-yl)acetamide Chemical compound C1=CC=C2N(CC(=O)N)CC=CC2=C1 GUCOHALGSMFJNM-UHFFFAOYSA-N 0.000 description 1
- OWMDVXXXAJDNKC-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)imidazo[1,2-a]quinolin-1-yl]-n-methylacetamide Chemical compound N1=C2C=CC3=CC=CC=C3N2C(CC(=O)NC)=C1C1=CC=C(Cl)C=C1 OWMDVXXXAJDNKC-UHFFFAOYSA-N 0.000 description 1
- PBYRQOOLDMKCDX-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)imidazo[1,2-a]quinolin-1-yl]acetic acid Chemical compound N1=C2C=CC3=CC=CC=C3N2C(CC(=O)O)=C1C1=CC=C(Cl)C=C1 PBYRQOOLDMKCDX-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- DOAZFHJDIDQFMT-UHFFFAOYSA-N C1(=CC=CC=C1)C=1N=C2N(C3=CC=CC=C3C=C2)C1CC(=O)N(C)C Chemical compound C1(=CC=CC=C1)C=1N=C2N(C3=CC=CC=C3C=C2)C1CC(=O)N(C)C DOAZFHJDIDQFMT-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 206010066296 Cerebral calcification Diseases 0.000 description 1
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
- 238000000585 Mann–Whitney U test Methods 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- CPYGBGOXCJJJGC-GKLGUMFISA-L alcuronium chloride Chemical compound [Cl-].[Cl-].C/1([C@@H]23)=C\N([C@H]4\5)C6=CC=CC=C6[C@]4(CC[N@@+]4(CC=C)C\C6=C\CO)[C@@H]4C[C@@H]6C/5=C/N3C3=CC=CC=C3[C@@]22CC[N@@+]3(CC=C)C/C(=C/CO)[C@@H]\1C[C@H]32 CPYGBGOXCJJJGC-GKLGUMFISA-L 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 230000001054 cortical effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 238000002566 electrocorticography Methods 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000001061 forehead Anatomy 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 238000002690 local anesthesia Methods 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 230000004617 sleep duration Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- SJUQWYQVPNNFBF-UHFFFAOYSA-M sodium;butanoic acid;hydroxide Chemical compound [OH-].[Na+].CCCC(O)=O SJUQWYQVPNNFBF-UHFFFAOYSA-M 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229940072358 xylocaine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8412446 | 1984-08-07 | ||
| FR8412446A FR2568879B1 (fr) | 1984-08-07 | 1984-08-07 | Imidazo(1,2-a)quinolines, leur preparation et leur application en therapeutique |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI853027A0 FI853027A0 (fi) | 1985-08-06 |
| FI853027L FI853027L (fi) | 1986-02-08 |
| FI79314B FI79314B (fi) | 1989-08-31 |
| FI79314C true FI79314C (fi) | 1989-12-11 |
Family
ID=9306855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI853027A FI79314C (fi) | 1984-08-07 | 1985-08-06 | Foerfarande foer framstaellning av terapeutiskt anvaendbara 2-fenyl-imidazo/1,2-a/kinolin-1-acetamider. |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0172097B1 (en, 2012) |
| JP (1) | JPS6147484A (en, 2012) |
| KR (1) | KR860001814A (en, 2012) |
| AR (1) | AR240674A1 (en, 2012) |
| AT (1) | ATE41001T1 (en, 2012) |
| AU (1) | AU573880B2 (en, 2012) |
| CA (1) | CA1263389A (en, 2012) |
| DE (1) | DE3568430D1 (en, 2012) |
| DK (1) | DK161963B (en, 2012) |
| ES (1) | ES8604593A1 (en, 2012) |
| FI (1) | FI79314C (en, 2012) |
| FR (1) | FR2568879B1 (en, 2012) |
| GR (1) | GR851929B (en, 2012) |
| HU (1) | HU199838B (en, 2012) |
| IL (1) | IL76019A0 (en, 2012) |
| MX (1) | MX161035A (en, 2012) |
| NO (1) | NO162188C (en, 2012) |
| NZ (1) | NZ213014A (en, 2012) |
| PT (1) | PT80920B (en, 2012) |
| ZA (1) | ZA855937B (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2593179B1 (fr) * | 1986-01-22 | 1988-04-01 | Synthelabo | Derives d'imidazo(1,2-a)quinoleines, leur preparation et leur application en therapeutique |
| FR2606410B1 (fr) * | 1986-11-07 | 1989-02-24 | Synthelabo | Imidazopyridines, leur preparation et leur application en therapeutique |
| EP0607076A1 (fr) * | 1993-01-15 | 1994-07-20 | Synthelabo | Dérivés de 9h-imidazo 1,2-a benzimidazole-3-acétamide à activité GABA |
| FR2700547B1 (fr) * | 1993-01-15 | 1995-02-17 | Synthelabo | Dérivés d'imidazo[2,1-b]benzosélénazole-3-acétamide, leur préparation et leur application en thérapeutique. |
| FR2700544B1 (fr) * | 1993-01-15 | 1995-02-17 | Synthelabo | Dérivés de 9H-imidazo[1,2-a]benzimidazole-3-acétamide, leur préparation et leur application en thérapeutique. |
| FR2707987B1 (fr) * | 1993-07-22 | 1995-09-08 | Synthelabo | Dérivés de 9H-imidazo[1,2-a]benzimidazole-3-acétamide, leur préparation et leur application en thérapeutique . |
| FR2719843B1 (fr) * | 1994-05-10 | 1996-06-07 | Synthelabo | Dérivés de 5,6-dihydro-4h-imidazo [2',1':2,3] imidazo-[4,5,1-ij] quinoléine et de 4,5-dihydroimidazo [1,2-a] pyrrolo-[1,2,3-cd] benzimidazole, leur préparation et leur application en thérapeutique. |
| FR2722501B1 (fr) * | 1994-07-13 | 1996-08-09 | Synthelabo | Derives de 9h-imidazo(1,2-a)benzimidazole-3-acetamide, leur preparation et leur application en therapeutique |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2492382A1 (fr) * | 1980-10-22 | 1982-04-23 | Synthelabo | Derives d'imidazo (1,2-a) pyridine, leur preparation et leur application en therapeutique |
-
1984
- 1984-08-07 FR FR8412446A patent/FR2568879B1/fr not_active Expired
-
1985
- 1985-07-30 DE DE8585401555T patent/DE3568430D1/de not_active Expired
- 1985-07-30 AT AT85401555T patent/ATE41001T1/de not_active IP Right Cessation
- 1985-07-30 EP EP85401555A patent/EP0172097B1/fr not_active Expired
- 1985-08-06 HU HU852992A patent/HU199838B/hu not_active IP Right Cessation
- 1985-08-06 PT PT80920A patent/PT80920B/pt not_active IP Right Cessation
- 1985-08-06 ZA ZA855937A patent/ZA855937B/xx unknown
- 1985-08-06 AU AU45814/85A patent/AU573880B2/en not_active Ceased
- 1985-08-06 NZ NZ213014A patent/NZ213014A/en unknown
- 1985-08-06 ES ES545929A patent/ES8604593A1/es not_active Expired
- 1985-08-06 JP JP60173976A patent/JPS6147484A/ja active Pending
- 1985-08-06 AR AR30120285A patent/AR240674A1/es active
- 1985-08-06 CA CA000488164A patent/CA1263389A/en not_active Expired
- 1985-08-06 IL IL76019A patent/IL76019A0/xx not_active IP Right Cessation
- 1985-08-06 KR KR1019850005659A patent/KR860001814A/ko not_active Ceased
- 1985-08-06 MX MX206216A patent/MX161035A/es unknown
- 1985-08-06 DK DK356985A patent/DK161963B/da not_active IP Right Cessation
- 1985-08-06 GR GR851929A patent/GR851929B/el unknown
- 1985-08-06 NO NO853099A patent/NO162188C/no unknown
- 1985-08-06 FI FI853027A patent/FI79314C/fi not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES545929A0 (es) | 1986-02-01 |
| NO162188B (no) | 1989-08-14 |
| KR860001814A (ko) | 1986-03-22 |
| AR240674A1 (es) | 1990-08-31 |
| FR2568879B1 (fr) | 1986-12-12 |
| DK356985D0 (da) | 1985-08-06 |
| AU4581485A (en) | 1986-02-13 |
| AU573880B2 (en) | 1988-06-23 |
| HU199838B (en) | 1990-03-28 |
| CA1263389A (en) | 1989-11-28 |
| NZ213014A (en) | 1988-05-30 |
| FI853027A0 (fi) | 1985-08-06 |
| MX161035A (es) | 1990-07-11 |
| EP0172097A1 (fr) | 1986-02-19 |
| FI853027L (fi) | 1986-02-08 |
| EP0172097B1 (fr) | 1989-03-01 |
| IL76019A0 (en) | 1985-12-31 |
| DK356985A (da) | 1986-02-08 |
| DE3568430D1 (en) | 1989-04-06 |
| PT80920B (pt) | 1987-12-30 |
| FR2568879A1 (fr) | 1986-02-14 |
| ES8604593A1 (es) | 1986-02-01 |
| NO162188C (no) | 1989-11-29 |
| DK161963B (da) | 1991-09-02 |
| FI79314B (fi) | 1989-08-31 |
| NO853099L (no) | 1986-02-10 |
| ATE41001T1 (de) | 1989-03-15 |
| GR851929B (en, 2012) | 1985-12-09 |
| HUT38636A (en) | 1986-06-30 |
| ZA855937B (en) | 1986-03-26 |
| JPS6147484A (ja) | 1986-03-07 |
| PT80920A (fr) | 1985-09-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69919364T2 (de) | Pyrroloindole, pyridoindole und azepinoindole als 5-ht2c agonisten | |
| KR910004450B1 (ko) | 3-아크릴아미노메틸이미다조[1,2-a]피리딘 유도체, 그의 제법 및 그를 포함하는 의약조성물 | |
| JP5972964B2 (ja) | 抗腫瘍剤としての三環式および四環式ピラゾロ［３，４−ｂ］ピリジン化合物 | |
| SK278605B6 (en) | Substituted bridged diazabicycloalkylquinolone carboxylic acids, method of producing and pharmaceutical compositions containing them | |
| JPH09504519A (ja) | ピリダジノキノリン化合物 | |
| JPS6072891A (ja) | ピリミド〔４，５−ｇ〕キノリンおよびその製造中間体 | |
| KR20030070590A (ko) | 세로토닌 효능제 및 길항제로서 치환된 피롤로퀴놀린 및피리도퀴놀린 | |
| US8039500B2 (en) | Fused heterocyclic compounds | |
| JP2003516989A (ja) | Ｇａｂａ受容体リガンドとしてのピラゾロ−ピリジン誘導体 | |
| JP3116230B2 (ja) | 三環式縮合ピリミジン誘導体 | |
| FI79314C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara 2-fenyl-imidazo/1,2-a/kinolin-1-acetamider. | |
| ES2342417T3 (es) | 1,8-naftiridinas como antagonistas de crf. | |
| FI92068C (fi) | Menetelmä uusien terapeuttisesti käyttökelpoisten 7-fluori-4-okso-8-(1-piperatsinyyli)-1,4-dihydro-1,8-bentso/b/naftyridiini-3-karboksyylihappojen valmistamiseksi | |
| KR20100031610A (ko) | 아데노신 Ａ3 수용체 리간드로서의 트리아졸로[1,5-ａ]퀴놀린 | |
| JPWO2003068776A1 (ja) | ［１，２，４］トリアゾロ［１，５−ｃ］ピリミジン誘導体 | |
| AU685881B2 (en) | 5-heteroarylindole derivatives as benzodiazepine receptor site agonists and antagonists | |
| US4767755A (en) | 3-(acylaminomethyl)imidazo[1,2-a]pyridine derivatives and pharmaceutical compositions | |
| JPH0853450A (ja) | ５，６−ジヒドロ−４Ｈ−イミダゾ［２’，１’：２，３］イミダゾ［４，５，１−ｉｊ］キノリンと４，５−ジヒドロイミダゾ［１，２−ａ］ピロロ［１，２，３−ｃｄ］ベンゾイミダゾール誘導体、その製法及びその治療への応用 | |
| US4675323A (en) | Imidazo(1,2-a)quinoline derivatives useful as anxiolytic agents | |
| EA005071B1 (ru) | ЗАМЕЩЕННЫЕ ПИРАЗОЛО[4,3-e]ДИАЗЕПИНЫ, ФАРМАЦЕВТИЧЕСКИЕ КОМПОЗИЦИИ, СОДЕРЖАЩИЕ ИХ, И ПРИМЕНЕНИЕ В КАЧЕСТВЕ ЛЕКАРСТВЕННЫХ ПРОДУКТОВ | |
| JP6595011B2 (ja) | 新規ホスホジエステラーゼ５阻害剤とその使用 | |
| FI84723B (fi) | Foerfarande foer framstaellning av terapeutiskt aktiva 2-(1,8-naftyridin-2-yl)-isoindolin-1-oner. | |
| JPS62169782A (ja) | １−（アシルアミノメチル）イミダゾ〔１，２−ａ〕キノリン誘導体、その製造法および医薬への応用 | |
| CZ285584B6 (cs) | 2,4,8-Trisubstituvané-3H,6H-1,4,5a,8a tetraazaacenaftylen-3,5-(4H)-diony a 2,4,8 trisubstiuované-4,5-dihydro-5-thioxo-3H,6H-1,4,5a ,8a-tetraazaacenaftylen-3-ony | |
| JPH10508617A (ja) | ピリダジノキノリン化合物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: SYNTHELABO |