IL45347A - 7h-indolizino(5,6,7-ij)isoquinoline derivatives processes for the preparation thereof and pharmaceutical compositions containing the same - Google Patents
7h-indolizino(5,6,7-ij)isoquinoline derivatives processes for the preparation thereof and pharmaceutical compositions containing the sameInfo
- Publication number
- IL45347A IL45347A IL45347A IL4534774A IL45347A IL 45347 A IL45347 A IL 45347A IL 45347 A IL45347 A IL 45347A IL 4534774 A IL4534774 A IL 4534774A IL 45347 A IL45347 A IL 45347A
- Authority
- IL
- Israel
- Prior art keywords
- radical
- carbon atoms
- indolizino
- general formula
- salts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 53
- 238000002360 preparation method Methods 0.000 title claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- LXGVPCGSNKMLRI-UHFFFAOYSA-N 2,10-diazatetracyclo[7.6.1.05,16.010,14]hexadeca-1,3,5(16),6,8,11,13-heptaene Chemical class C1=NC(CC=2N3C=CC=2)=C2C3=CC=CC2=C1 LXGVPCGSNKMLRI-UHFFFAOYSA-N 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 82
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 65
- 150000003839 salts Chemical class 0.000 claims description 43
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 19
- HSHAHDDZXBQMDT-UHFFFAOYSA-N 7h-indolizino[5,6,7-ij]isoquinolin-7-one Chemical compound C1=NC(C(=O)C=2N3C=CC=2)=C2C3=CC=CC2=C1 HSHAHDDZXBQMDT-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 150000002923 oximes Chemical class 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 238000007127 saponification reaction Methods 0.000 claims description 3
- BJHXGXAYEJNLHC-UHFFFAOYSA-N 7-isopropoxycarbonylmethoxyimino-7h-indolizino[5,6,7-ij]isoquinoline Chemical compound C1=NC(C(=NOCC(=O)OC(C)C)C=2N3C=CC=2)=C2C3=CC=CC2=C1 BJHXGXAYEJNLHC-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 109
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
- 238000002844 melting Methods 0.000 description 54
- 230000008018 melting Effects 0.000 description 54
- -1 alkoxy radical Chemical class 0.000 description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 49
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 41
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 238000000354 decomposition reaction Methods 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000001953 recrystallisation Methods 0.000 description 21
- 239000000155 melt Substances 0.000 description 20
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000009835 boiling Methods 0.000 description 17
- 239000013078 crystal Substances 0.000 description 17
- 239000000725 suspension Substances 0.000 description 14
- 238000001035 drying Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 11
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 150000002537 isoquinolines Chemical class 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- DFMXJRGGNCRUHZ-UHFFFAOYSA-N 6h-isoquinolin-7-one Chemical compound C1=CN=CC2=CC(=O)CC=C21 DFMXJRGGNCRUHZ-UHFFFAOYSA-N 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 239000012153 distilled water Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- BVMPIDSTEUBIOC-UHFFFAOYSA-N 2-(2,10-diazatetracyclo[7.6.1.05,16.010,14]hexadeca-1,3,5(16),6,8,11,13-heptaen-15-ylideneamino)oxyacetic acid Chemical compound C1=NC(C(=NOCC(=O)O)C=2N3C=CC=2)=C2C3=CC=CC2=C1 BVMPIDSTEUBIOC-UHFFFAOYSA-N 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- KJUPLFBPDWRECV-UHFFFAOYSA-N N-(2,10-diazatetracyclo[7.6.1.05,16.010,14]hexadeca-1,3,5(16),6,8,11,13-heptaen-15-ylidene)hydroxylamine Chemical compound C1=NC(C(=NO)C=2N3C=CC=2)=C2C3=CC=CC2=C1 KJUPLFBPDWRECV-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 230000003226 decolorizating effect Effects 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000242680 Schistosoma mansoni Species 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 150000002466 imines Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- GUSYANXQYUJOBH-UHFFFAOYSA-N isoquinolin-8-amine Chemical class C1=NC=C2C(N)=CC=CC2=C1 GUSYANXQYUJOBH-UHFFFAOYSA-N 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- YTSJWBUJZLIWNE-UHFFFAOYSA-M (2-ethoxy-2-oxoethoxy)azanium;chloride Chemical compound [Cl-].CCOC(=O)CO[NH3+] YTSJWBUJZLIWNE-UHFFFAOYSA-M 0.000 description 2
- KBXIJIPYZKPDRU-UHFFFAOYSA-N (aminooxy)acetic acid hemihydrochloride Chemical compound Cl.NOCC(O)=O.NOCC(O)=O KBXIJIPYZKPDRU-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 2
- YYHXNLCQPSAQEC-UHFFFAOYSA-N 8-pyrrol-1-ylisoquinoline Chemical compound C1=CC=CN1C1=CC=CC2=CC=NC=C12 YYHXNLCQPSAQEC-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-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
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000000507 anthelmentic effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000008119 colloidal silica Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- SXDSDQFSCFZVMY-UHFFFAOYSA-N ethyl 2-(2,10-diazatetracyclo[7.6.1.05,16.010,14]hexadeca-1,3,5(16),6,8,11,13-heptaen-15-ylideneamino)oxyacetate Chemical compound C1=NC(C(=NOCC(=O)OCC)C=2N3C=CC=2)=C2C3=CC=CC2=C1 SXDSDQFSCFZVMY-UHFFFAOYSA-N 0.000 description 2
- HQMDJAQPJKEYHB-UHFFFAOYSA-N ethyl 2-(2,10-diazatetracyclo[7.6.1.05,16.010,14]hexadeca-1,3,5(16),6,8,11,13-heptaen-15-ylideneamino)oxybutanoate Chemical compound C1=NC(C(=NOC(CC)C(=O)OCC)C=2N3C=CC=2)=C2C3=CC=CC2=C1 HQMDJAQPJKEYHB-UHFFFAOYSA-N 0.000 description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229940100445 wheat starch Drugs 0.000 description 2
- LSXKDWGTSHCFPP-UHFFFAOYSA-N 1-bromoheptane Chemical compound CCCCCCCBr LSXKDWGTSHCFPP-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- JCLWXHDMLLDHPL-UHFFFAOYSA-N 1-iodohexane Chemical compound [CH2]CCCCCI JCLWXHDMLLDHPL-UHFFFAOYSA-N 0.000 description 1
- ZLKHNURELCONBB-UHFFFAOYSA-N 2,5-diethoxyoxolane Chemical compound CCOC1CCC(OCC)O1 ZLKHNURELCONBB-UHFFFAOYSA-N 0.000 description 1
- UNUKRWQKEVCJSZ-UHFFFAOYSA-N 2-(2,10-diazatetracyclo[7.6.1.05,16.010,14]hexadeca-1,3,5(16),6,8,11,13-heptaen-15-ylideneamino)oxybutanoic acid Chemical compound C1=NC(C(=NOC(CC)C(O)=O)C=2N3C=CC=2)=C2C3=CC=CC2=C1 UNUKRWQKEVCJSZ-UHFFFAOYSA-N 0.000 description 1
- MSWUXFONJFGRMV-UHFFFAOYSA-N 2-(2,10-diazatetracyclo[7.6.1.05,16.010,14]hexadeca-1,3,5(16),6,8,11,13-heptaen-15-ylideneamino)oxypentanoic acid Chemical compound C1=NC(C(=NOC(CCC)C(O)=O)C=2N3C=CC=2)=C2C3=CC=CC2=C1 MSWUXFONJFGRMV-UHFFFAOYSA-N 0.000 description 1
- ONNXJNLCGRWYCR-UHFFFAOYSA-N 2-aminooxybutanoic acid;hydrochloride Chemical compound Cl.CCC(ON)C(O)=O ONNXJNLCGRWYCR-UHFFFAOYSA-N 0.000 description 1
- CWEWBCLCRPGTIO-UHFFFAOYSA-N 2-aminooxypropanoic acid;hydrochloride Chemical compound Cl.NOC(C)C(O)=O CWEWBCLCRPGTIO-UHFFFAOYSA-N 0.000 description 1
- XRRWTXUSRDXCLW-UHFFFAOYSA-N 3-aminooxypropanoic acid;hydrochloride Chemical compound Cl.NOCCC(O)=O XRRWTXUSRDXCLW-UHFFFAOYSA-N 0.000 description 1
- BSKDHGUEAFEHIH-UHFFFAOYSA-N 3-chloro-7-carboxymethoxyimino-7h-indolizino[5,6,7-ij]isoquinoline Chemical compound C1=NC(C(=NOCC(=O)O)C=2N3C=CC=2)=C2C3=CC=C(Cl)C2=C1 BSKDHGUEAFEHIH-UHFFFAOYSA-N 0.000 description 1
- PGTSXYXHCHGVQR-UHFFFAOYSA-N 3-chloro-7-ethoxycarbonylmethoxyimino-7h-indolizino[5,6,7-ij]isoquinoline Chemical compound C1=NC(C(=NOCC(=O)OCC)C=2N3C=CC=2)=C2C3=CC=C(Cl)C2=C1 PGTSXYXHCHGVQR-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- BAIXIQOQJGWFNJ-UHFFFAOYSA-N 5-chloro-8-pyrrol-1-ylisoquinoline Chemical compound C12=CN=CC=C2C(Cl)=CC=C1N1C=CC=C1 BAIXIQOQJGWFNJ-UHFFFAOYSA-N 0.000 description 1
- SIBIHDYMXLMZOD-UHFFFAOYSA-N 5-chloro-8-pyrrol-1-ylisoquinoline-1-carbonitrile Chemical compound C12=C(C#N)N=CC=C2C(Cl)=CC=C1N1C=CC=C1 SIBIHDYMXLMZOD-UHFFFAOYSA-N 0.000 description 1
- JZNPXPCJZLGGEZ-UHFFFAOYSA-N 5-chloroisoquinolin-8-amine Chemical compound C1=NC=C2C(N)=CC=C(Cl)C2=C1 JZNPXPCJZLGGEZ-UHFFFAOYSA-N 0.000 description 1
- WKGHWSLZIIZEHE-UHFFFAOYSA-N 7-(1-carboxyethoxyimino)-7h-indolizino[5,6,7-ij]isoquinoline Chemical compound C1=NC(C(=NOC(C)C(O)=O)C=2N3C=CC=2)=C2C3=CC=CC2=C1 WKGHWSLZIIZEHE-UHFFFAOYSA-N 0.000 description 1
- YXXCBHQUEOVJOL-UHFFFAOYSA-N 7-acetyloxyimino-7h-indolizino[5,6,7-ij]isoquinoline Chemical compound C1=NC(C(=NOC(=O)C)C=2N3C=CC=2)=C2C3=CC=CC2=C1 YXXCBHQUEOVJOL-UHFFFAOYSA-N 0.000 description 1
- NUUBVXHOZASULU-UHFFFAOYSA-N 7-carbamoylmethoxyimino-7h-indolizino[5,6,7-ij]isoquinoline Chemical compound C1=NC(C(=NOCC(=O)N)C=2N3C=CC=2)=C2C3=CC=CC2=C1 NUUBVXHOZASULU-UHFFFAOYSA-N 0.000 description 1
- JEHMFLWMPAOHDW-UHFFFAOYSA-N 7-chloro-8-pyrrol-1-ylisoquinoline Chemical compound ClC1=CC=C2C=CN=CC2=C1N1C=CC=C1 JEHMFLWMPAOHDW-UHFFFAOYSA-N 0.000 description 1
- UCRRLXCKKSCONJ-UHFFFAOYSA-N 7-chloro-8-pyrrol-1-ylisoquinoline-1-carbonitrile Chemical compound ClC1=CC=C2C=CN=C(C#N)C2=C1N1C=CC=C1 UCRRLXCKKSCONJ-UHFFFAOYSA-N 0.000 description 1
- MNZMTNUGYPSZRQ-UHFFFAOYSA-N 7-chloroisoquinolin-8-amine Chemical compound C1=NC=C2C(N)=C(Cl)C=CC2=C1 MNZMTNUGYPSZRQ-UHFFFAOYSA-N 0.000 description 1
- LYDOQALSQUUOPU-UHFFFAOYSA-N 7-imino-7h-indolizino[5,6,7-ij]isoquinoline Chemical compound C1=NC(C(=N)C=2N3C=CC=2)=C2C3=CC=CC2=C1 LYDOQALSQUUOPU-UHFFFAOYSA-N 0.000 description 1
- PAIRFQAOBJMHIN-UHFFFAOYSA-N 7-methoxy-8-pyrrol-1-ylisoquinoline Chemical compound COC1=CC=C2C=CN=CC2=C1N1C=CC=C1 PAIRFQAOBJMHIN-UHFFFAOYSA-N 0.000 description 1
- YMYXYGWPFNZEET-UHFFFAOYSA-N 7-methoxyisoquinolin-8-amine Chemical compound C1=CN=CC2=C(N)C(OC)=CC=C21 YMYXYGWPFNZEET-UHFFFAOYSA-N 0.000 description 1
- OUJBCCDIJAEIMU-UHFFFAOYSA-N 8-methoxy-2,10-diazatetracyclo[7.6.1.05,16.010,14]hexadeca-1,3,5(16),6,8,11,13-heptaen-15-imine Chemical compound N12C=CC=C2C(=N)C=2C3=C1C(OC)=CC=C3C=CN=2 OUJBCCDIJAEIMU-UHFFFAOYSA-N 0.000 description 1
- 101150058502 Acaca gene Proteins 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- XPGNVMMYRQAXCP-UHFFFAOYSA-N C(C)OC(=O)C(CC1=CC=CC=C1)ON=C1C2=CC=CN2C=2C=CC=C3C=CN=C1C=23 Chemical compound C(C)OC(=O)C(CC1=CC=CC=C1)ON=C1C2=CC=CN2C=2C=CC=C3C=CN=C1C=23 XPGNVMMYRQAXCP-UHFFFAOYSA-N 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- LKVWTUBITRHNKS-UHFFFAOYSA-N N-(6-chloro-2,10-diazatetracyclo[7.6.1.05,16.010,14]hexadeca-1,3,5,7,9(16),11,13-heptaen-15-ylidene)hydroxylamine Chemical compound C1=NC(C(=NO)C=2N3C=CC=2)=C2C3=CC=C(Cl)C2=C1 LKVWTUBITRHNKS-UHFFFAOYSA-N 0.000 description 1
- LQGCFQGOXSVHRA-UHFFFAOYSA-N N-(8-methoxy-2,10-diazatetracyclo[7.6.1.05,16.010,14]hexadeca-1,3,5(16),6,8,11,13-heptaen-15-ylidene)hydroxylamine Chemical compound N12C=CC=C2C(=NO)C=2C3=C1C(OC)=CC=C3C=CN=2 LQGCFQGOXSVHRA-UHFFFAOYSA-N 0.000 description 1
- 241000242678 Schistosoma Species 0.000 description 1
- 241000242683 Schistosoma haematobium Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 230000000425 anti-bilharzial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- FJMGPCOTOKZINX-UHFFFAOYSA-N ethyl 2-(2,10-diazatetracyclo[7.6.1.05,16.010,14]hexadeca-1,3,5(16),6,8,11,13-heptaen-15-ylideneamino)oxy-2-methylpropanoate Chemical compound C1=NC(C(=NOC(C)(C)C(=O)OCC)C=2N3C=CC=2)=C2C3=CC=CC2=C1 FJMGPCOTOKZINX-UHFFFAOYSA-N 0.000 description 1
- JHBBVOSRASYSLK-UHFFFAOYSA-N ethyl 2-(2,10-diazatetracyclo[7.6.1.05,16.010,14]hexadeca-1,3,5(16),6,8,11,13-heptaen-15-ylideneamino)oxypentanoate Chemical compound C1=NC(C(=NOC(CCC)C(=O)OCC)C=2N3C=CC=2)=C2C3=CC=CC2=C1 JHBBVOSRASYSLK-UHFFFAOYSA-N 0.000 description 1
- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 1
- MVCUFNYFDQMSTE-UHFFFAOYSA-N ethyl 2-bromo-3-phenylpropanoate Chemical compound CCOC(=O)C(Br)CC1=CC=CC=C1 MVCUFNYFDQMSTE-UHFFFAOYSA-N 0.000 description 1
- XIMFCGSNSKXPBO-UHFFFAOYSA-N ethyl 2-bromobutanoate Chemical compound CCOC(=O)C(Br)CC XIMFCGSNSKXPBO-UHFFFAOYSA-N 0.000 description 1
- ORSIRXYHFPHWTN-UHFFFAOYSA-N ethyl 2-bromopentanoate Chemical compound CCCC(Br)C(=O)OCC ORSIRXYHFPHWTN-UHFFFAOYSA-N 0.000 description 1
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 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
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ZJVDVOWYYDUKTE-UHFFFAOYSA-N heptyl 2-(2,10-diazatetracyclo[7.6.1.05,16.010,14]hexadeca-1,3,5(16),6,8,11,13-heptaen-15-ylideneamino)oxyacetate Chemical compound C1=NC(C(=NOCC(=O)OCCCCCCC)C=2N3C=CC=2)=C2C3=CC=CC2=C1 ZJVDVOWYYDUKTE-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000008016 pharmaceutical coating Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- MVAHCZOBQYCYFS-UHFFFAOYSA-N propan-2-yl 2-aminooxyacetate;hydrochloride Chemical compound Cl.CC(C)OC(=O)CON MVAHCZOBQYCYFS-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- C07D471/16—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7327649A FR2244515A1 (en) | 1973-07-27 | 1973-07-27 | 7H-Indolizino (5,6,7-i,j)-isoquinolines - as antibilharzial, anthelmintic and antimicrobial agents |
| FR7341616A FR2252087A2 (en) | 1973-11-22 | 1973-11-22 | 7H-Indolizino (5,6,7-i,j)-isoquinolines - as antibilharzial, anthelmintic and antimicrobial agents |
| FR7418808A FR2272668A2 (en) | 1974-05-30 | 1974-05-30 | 7H-Indolizino (5,6,7-i,j)-isoquinolines - as antibilharzial, anthelmintic and antimicrobial agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL45347A0 IL45347A0 (en) | 1974-10-22 |
| IL45347A true IL45347A (en) | 1977-01-31 |
Family
ID=27250154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL45347A IL45347A (en) | 1973-07-27 | 1974-07-25 | 7h-indolizino(5,6,7-ij)isoquinoline derivatives processes for the preparation thereof and pharmaceutical compositions containing the same |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3946019A (de) |
| JP (1) | JPS5041899A (de) |
| AR (1) | AR204011A1 (de) |
| AT (1) | AT335457B (de) |
| CH (1) | CH590282A5 (de) |
| DE (1) | DE2436233A1 (de) |
| EG (1) | EG11219A (de) |
| GB (1) | GB1442102A (de) |
| HU (1) | HU172290B (de) |
| IE (1) | IE39813B1 (de) |
| IL (1) | IL45347A (de) |
| NL (1) | NL7409814A (de) |
| OA (1) | OA04812A (de) |
| PH (1) | PH10500A (de) |
| ZM (1) | ZM12174A1 (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2317880A1 (fr) * | 1975-07-15 | 1977-02-11 | Rhone Poulenc Ind | Compositions agricoles a base de 7h-indolizino(7,6,5-de)isoquinoleine |
| US5227383A (en) * | 1991-06-14 | 1993-07-13 | The University Of Mississippi | Compounds and compositions useful as antifungal and antimycobacterial agents |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3793328A (en) * | 1969-11-03 | 1974-02-19 | Upjohn Co | 8benzoyl 1,2,3,4 tetrahydroquinoline |
| US3784550A (en) * | 1971-08-13 | 1974-01-08 | Squibb & Sons Inc | N-(2,3-dihydroquinobenzoxa(or thia)zepin-3-ylidene)-o-(substituted benzoyl)hydroxylamines |
-
1974
- 1974-01-01 AR AR254909A patent/AR204011A1/es active
- 1974-07-05 OA OA55241A patent/OA04812A/xx unknown
- 1974-07-19 NL NL7409814A patent/NL7409814A/xx not_active Application Discontinuation
- 1974-07-25 ZM ZM121/74A patent/ZM12174A1/xx unknown
- 1974-07-25 US US05/491,642 patent/US3946019A/en not_active Expired - Lifetime
- 1974-07-25 PH PH16091A patent/PH10500A/en unknown
- 1974-07-25 GB GB3290174A patent/GB1442102A/en not_active Expired
- 1974-07-25 HU HU74RO00000789A patent/HU172290B/hu unknown
- 1974-07-25 JP JP49084700A patent/JPS5041899A/ja active Pending
- 1974-07-25 IL IL45347A patent/IL45347A/en unknown
- 1974-07-25 IE IE1578/74A patent/IE39813B1/xx unknown
- 1974-07-26 AT AT616874A patent/AT335457B/de not_active IP Right Cessation
- 1974-07-26 DE DE2436233A patent/DE2436233A1/de not_active Withdrawn
- 1974-07-26 CH CH1035174A patent/CH590282A5/xx not_active IP Right Cessation
- 1974-07-27 EG EG301/74A patent/EG11219A/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| ZM12174A1 (en) | 1975-03-21 |
| DE2436233A1 (de) | 1975-02-13 |
| CH590282A5 (de) | 1977-07-29 |
| ATA616874A (de) | 1976-07-15 |
| AU7166374A (en) | 1976-01-29 |
| GB1442102A (en) | 1976-07-07 |
| JPS5041899A (de) | 1975-04-16 |
| IE39813L (en) | 1975-01-27 |
| PH10500A (en) | 1977-05-17 |
| IE39813B1 (en) | 1979-01-03 |
| IL45347A0 (en) | 1974-10-22 |
| NL7409814A (nl) | 1975-01-29 |
| AR204011A1 (es) | 1975-11-12 |
| OA04812A (fr) | 1980-10-31 |
| US3946019A (en) | 1976-03-23 |
| AT335457B (de) | 1977-03-10 |
| HU172290B (hu) | 1978-07-28 |
| EG11219A (en) | 1977-01-31 |
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