CS203184B2 - Process for preparing new pyrroloquinoxalinones and pyrrolobenzodiazepinones - Google Patents
Process for preparing new pyrroloquinoxalinones and pyrrolobenzodiazepinones Download PDFInfo
- Publication number
- CS203184B2 CS203184B2 CS781094A CS109478A CS203184B2 CS 203184 B2 CS203184 B2 CS 203184B2 CS 781094 A CS781094 A CS 781094A CS 109478 A CS109478 A CS 109478A CS 203184 B2 CS203184 B2 CS 203184B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- phenyl
- acid
- dihydro
- calculated
- atom
- Prior art date
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- SMZQDPJVHZLLLS-UHFFFAOYSA-N pyrrolo[2,3-h]quinoxalin-2-one Chemical class C1=C2N=CC=C2C2=NC(=O)C=NC2=C1 SMZQDPJVHZLLLS-UHFFFAOYSA-N 0.000 title claims abstract description 5
- VRQOSIAJWZNUSL-UHFFFAOYSA-N 2h-pyrrolo[2,3-i][1,2]benzodiazepin-3-one Chemical class C12=NNC(=O)C=CC2=CC=C2C1=CC=N2 VRQOSIAJWZNUSL-UHFFFAOYSA-N 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 38
- 238000002360 preparation method Methods 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 15
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- OKPCRTAIFSBILC-UHFFFAOYSA-N 3,6-dihydroquinoxaline-2,5-dione Chemical compound O=C1CC=CC2=NC(=O)CN=C21 OKPCRTAIFSBILC-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 239000007809 chemical reaction catalyst Substances 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract description 6
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 6
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 5
- 239000003146 anticoagulant agent Substances 0.000 abstract description 5
- 229960004676 antithrombotic agent Drugs 0.000 abstract description 4
- 241000551547 Dione <red algae> Species 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- 238000004458 analytical method Methods 0.000 description 37
- 238000002425 crystallisation Methods 0.000 description 29
- 230000008025 crystallization Effects 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 23
- -1 it is - methyl Chemical group 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
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- 239000002904 solvent Substances 0.000 description 10
- 238000011282 treatment Methods 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 241000700198 Cavia Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000007363 ring formation reaction Methods 0.000 description 6
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 102000008186 Collagen Human genes 0.000 description 5
- 108010035532 Collagen Proteins 0.000 description 5
- 206010015150 Erythema Diseases 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 229920001436 collagen Polymers 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical class C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- FGEAOSXMQZWHIQ-UHFFFAOYSA-N 2-chloro-2-phenylacetyl chloride Chemical compound ClC(=O)C(Cl)C1=CC=CC=C1 FGEAOSXMQZWHIQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PVHGBNYTCJASNZ-UHFFFAOYSA-N C1=CNC2=C3C=CN=C3C=CC2=N1 Chemical class C1=CNC2=C3C=CN=C3C=CC2=N1 PVHGBNYTCJASNZ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004471 Glycine Substances 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 231100000321 erythema Toxicity 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 150000003252 quinoxalines Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- BERNQQVIUAZUHY-UHFFFAOYSA-N (2-chloro-2-oxo-1-phenylethyl) acetate Chemical compound CC(=O)OC(C(Cl)=O)C1=CC=CC=C1 BERNQQVIUAZUHY-UHFFFAOYSA-N 0.000 description 2
- UZIJSDLMSLIHJC-UHFFFAOYSA-N 1-propylquinoxalin-2-one Chemical compound C1=CC=C2N=CC(=O)N(CCC)C2=C1 UZIJSDLMSLIHJC-UHFFFAOYSA-N 0.000 description 2
- HYTIPJFUWHYQON-UHFFFAOYSA-N 3,4-dihydro-1h-quinoxalin-2-one Chemical compound C1=CC=C2NC(=O)CNC2=C1 HYTIPJFUWHYQON-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- IBVRNLCFTHSDEM-UHFFFAOYSA-N 6h-quinoxalin-5-one Chemical class C1=CN=C2C(=O)CC=CC2=N1 IBVRNLCFTHSDEM-UHFFFAOYSA-N 0.000 description 2
- FYSLFQDLMDRXNP-UHFFFAOYSA-N 7-chloro-3,4-dihydro-1h-quinoxalin-2-one Chemical compound N1CC(=O)NC2=CC(Cl)=CC=C21 FYSLFQDLMDRXNP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 101150101537 Olah gene Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
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- 239000000654 additive Substances 0.000 description 2
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- 238000004220 aggregation Methods 0.000 description 2
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- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
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- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
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- 239000011592 zinc chloride Substances 0.000 description 2
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- HORKYAIEVBUXGM-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoxaline Chemical compound C1=CC=C2NCCNC2=C1 HORKYAIEVBUXGM-UHFFFAOYSA-N 0.000 description 1
- ZHYMGSPDEVXULU-UHFFFAOYSA-N 1,2-benzodiazepin-3-one Chemical class N1=NC(=O)C=CC2=CC=CC=C21 ZHYMGSPDEVXULU-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- IAWKCVVUAYRUNF-UHFFFAOYSA-N 1,9-diazatricyclo[6.4.1.04,13]trideca-2,4(13),5,7,9,11-hexaene Chemical compound C1=CC=NC2=CC=CC3=C2N1C=C3 IAWKCVVUAYRUNF-UHFFFAOYSA-N 0.000 description 1
- UYAZINQILIDECE-UHFFFAOYSA-N 1-chloro-3,4-dihydroquinoxalin-2-one Chemical compound ClN1C(CNC2=CC=CC=C12)=O UYAZINQILIDECE-UHFFFAOYSA-N 0.000 description 1
- QIMNRZXHTWNKAL-UHFFFAOYSA-N 1-propyl-3,4-dihydroquinoxalin-2-one Chemical compound C1=CC=C2N(CCC)C(=O)CNC2=C1 QIMNRZXHTWNKAL-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- IQAIPUWCYPGRQL-UHFFFAOYSA-N 2-hydroxyacetic acid;hydrate Chemical compound O.OCC(O)=O IQAIPUWCYPGRQL-UHFFFAOYSA-N 0.000 description 1
- MWRHWPHADLTIBW-UHFFFAOYSA-N 2h-pyrrolo[3,2-b]quinoxaline Chemical compound C1=CC=CC2=NC3=NCC=C3N=C21 MWRHWPHADLTIBW-UHFFFAOYSA-N 0.000 description 1
- YRELTDGOEVJYLO-UHFFFAOYSA-N 3-ethyl-3,4-dihydro-1h-quinoxalin-2-one Chemical compound C1=CC=C2NC(=O)C(CC)NC2=C1 YRELTDGOEVJYLO-UHFFFAOYSA-N 0.000 description 1
- VFPSXIUJTNCWGH-UHFFFAOYSA-N 3H-quinoxalin-5-one Chemical compound N1=CCN=C2C(=O)C=CC=C21 VFPSXIUJTNCWGH-UHFFFAOYSA-N 0.000 description 1
- VXAZMSMPGZDYOH-UHFFFAOYSA-N 4-(2-hydroxy-2-phenylacetyl)-1,3-dihydroquinoxalin-2-one Chemical compound C1C(=O)NC2=CC=CC=C2N1C(=O)C(O)C1=CC=CC=C1 VXAZMSMPGZDYOH-UHFFFAOYSA-N 0.000 description 1
- XPMRPEIULRSOMD-UHFFFAOYSA-N 7,8-dihydro-1,2-benzodiazepin-6-one Chemical class N1=NC=CC=C2C(=O)CCC=C21 XPMRPEIULRSOMD-UHFFFAOYSA-N 0.000 description 1
- RZRRWGDTYRJZIX-UHFFFAOYSA-N 7,8-dihydro-1,5-benzodiazepin-6-one Chemical class N1=CC=CN=C2C(=O)CCC=C21 RZRRWGDTYRJZIX-UHFFFAOYSA-N 0.000 description 1
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- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 150000002332 glycine derivatives Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- PNDZEEPOYCVIIY-UHFFFAOYSA-N indo-1 Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(OCCOC=2C(=CC=C(C=2)C=2N=C3[CH]C(=CC=C3C=2)C(O)=O)N(CC(O)=O)CC(O)=O)=C1 PNDZEEPOYCVIIY-UHFFFAOYSA-N 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XTBLDMQMUSHDEN-UHFFFAOYSA-N naphthalene-2,3-diamine Chemical compound C1=CC=C2C=C(N)C(N)=CC2=C1 XTBLDMQMUSHDEN-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000004971 nitroalkyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 230000001732 thrombotic effect Effects 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS792091A CS203185B2 (cs) | 1977-02-25 | 1979-03-29 | Způsob výroby 6-hydroxy-6-fenyl-lH-pyrrolo[1,2,3-de ]- -chinoxalin-2,5 (3H,6H) dionu |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/772,154 US4075206A (en) | 1977-02-25 | 1977-02-25 | Substituted pyrroloquinoxalinones and diones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS203184B2 true CS203184B2 (en) | 1981-02-27 |
Family
ID=25094096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS781094A CS203184B2 (en) | 1977-02-25 | 1978-02-21 | Process for preparing new pyrroloquinoxalinones and pyrrolobenzodiazepinones |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US4075206A (de) |
| JP (1) | JPS53111095A (de) |
| AR (1) | AR218056A1 (de) |
| AT (1) | AT361489B (de) |
| AU (1) | AU513391B2 (de) |
| BE (1) | BE864105A (de) |
| BG (1) | BG28565A3 (de) |
| CA (1) | CA1097631A (de) |
| CS (1) | CS203184B2 (de) |
| DD (1) | DD134871A5 (de) |
| DE (1) | DE2807145A1 (de) |
| DK (1) | DK74578A (de) |
| ES (1) | ES467189A1 (de) |
| FR (1) | FR2381767A1 (de) |
| GB (1) | GB1595745A (de) |
| GR (1) | GR68942B (de) |
| IL (1) | IL54086A0 (de) |
| IT (1) | IT1094215B (de) |
| NL (1) | NL7801927A (de) |
| NZ (1) | NZ186512A (de) |
| PH (1) | PH13147A (de) |
| PL (1) | PL204796A1 (de) |
| PT (1) | PT67678B (de) |
| SE (1) | SE7802024L (de) |
| YU (1) | YU39178A (de) |
| ZA (1) | ZA78991B (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4262123A (en) * | 1978-09-11 | 1981-04-14 | The Upjohn Company | Quinoxalinones |
| US4242342A (en) * | 1979-05-31 | 1980-12-30 | The Upjohn Company | Quinoxalinones useful for treating atopic eczema and urticaria |
| US4499270A (en) * | 1981-04-16 | 1985-02-12 | Riker Laboratories, Inc. | Substituted pyridoquinoxaline-6-carboxylic acids and derivatives thereof |
| IL93136A (en) * | 1989-02-23 | 1995-01-24 | Janssen Pharmaceutica Nv | Tetrahydroimidazo (1,4) benzodiazepin-2-thione derivatives, their preparation and pharmaceutical compositions containing them |
| NZ235137A (en) * | 1989-09-13 | 1992-02-25 | Janssen Pharmaceutica Nv | Tetrahydroimidazo(1,4)benzodiazepine derivatives, preparation and pharmaceutical compositions thereof |
| JPH05117276A (ja) * | 1991-10-23 | 1993-05-14 | Sumitomo Pharmaceut Co Ltd | 新規な３環性キノキサリンジオン誘導体 |
| TW260660B (de) * | 1993-04-22 | 1995-10-21 | Sumitomo Pharma | |
| CN114230528B (zh) * | 2021-11-25 | 2024-02-06 | 桂林理工大学 | 一种制备喹喔啉酮衍生物的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3892746A (en) * | 1969-06-09 | 1975-07-01 | American Home Prod | Pyrrolo{8 1,2,3-de{9 quinoxalin-2(3H)-ones and related compounds |
| US3813392A (en) * | 1969-06-09 | 1974-05-28 | J Sellstedt | Pyrrolo(1,2,3-alpha epsilon)quinoxalin-2(3h)-ones and related compounds |
| US3579503A (en) * | 1969-11-03 | 1971-05-18 | Upjohn Co | Pyrrolo(3,2,1-jk)(1,4)benzodiazepinones |
| US3642821A (en) * | 1969-11-03 | 1972-02-15 | Upjohn Co | Tetrahydropyrrolobenzodiazepines |
-
1977
- 1977-02-25 US US05/772,154 patent/US4075206A/en not_active Expired - Lifetime
- 1977-09-26 US US05/836,830 patent/US4087527A/en not_active Expired - Lifetime
-
1978
- 1978-02-17 GB GB6298/78A patent/GB1595745A/en not_active Expired
- 1978-02-20 AU AU33433/78A patent/AU513391B2/en not_active Expired
- 1978-02-20 CA CA297,309A patent/CA1097631A/en not_active Expired
- 1978-02-20 GR GR55496A patent/GR68942B/el unknown
- 1978-02-20 JP JP1902178A patent/JPS53111095A/ja active Pending
- 1978-02-20 ZA ZA00780991A patent/ZA78991B/xx unknown
- 1978-02-20 AR AR271156A patent/AR218056A1/es active
- 1978-02-20 BE BE1008716A patent/BE864105A/xx unknown
- 1978-02-20 FR FR7804728A patent/FR2381767A1/fr active Pending
- 1978-02-20 NZ NZ186512A patent/NZ186512A/xx unknown
- 1978-02-20 DE DE19782807145 patent/DE2807145A1/de not_active Withdrawn
- 1978-02-20 DK DK74578A patent/DK74578A/da unknown
- 1978-02-20 PT PT67678A patent/PT67678B/pt unknown
- 1978-02-20 IT IT20417/78A patent/IT1094215B/it active
- 1978-02-20 PH PH20799A patent/PH13147A/en unknown
- 1978-02-20 IL IL54086A patent/IL54086A0/xx unknown
- 1978-02-21 CS CS781094A patent/CS203184B2/cs unknown
- 1978-02-21 NL NL7801927A patent/NL7801927A/xx not_active Application Discontinuation
- 1978-02-21 ES ES467189A patent/ES467189A1/es not_active Expired
- 1978-02-21 YU YU00391/78A patent/YU39178A/xx unknown
- 1978-02-21 SE SE7802024A patent/SE7802024L/xx unknown
- 1978-02-21 DD DD78203784A patent/DD134871A5/de unknown
- 1978-02-21 BG BG038764A patent/BG28565A3/xx unknown
- 1978-02-21 PL PL20479678A patent/PL204796A1/xx unknown
- 1978-02-23 AT AT131578A patent/AT361489B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GR68942B (de) | 1982-03-29 |
| PL204796A1 (pl) | 1979-04-09 |
| PT67678B (en) | 1979-07-20 |
| DK74578A (da) | 1978-08-26 |
| BE864105A (fr) | 1978-08-21 |
| AR218056A1 (es) | 1980-05-15 |
| AU513391B2 (en) | 1980-11-27 |
| DE2807145A1 (de) | 1978-08-31 |
| YU39178A (en) | 1983-01-21 |
| IL54086A0 (en) | 1978-04-30 |
| ATA131578A (de) | 1980-08-15 |
| ZA78991B (en) | 1979-10-31 |
| PT67678A (en) | 1978-03-01 |
| JPS53111095A (en) | 1978-09-28 |
| NZ186512A (en) | 1981-03-16 |
| BG28565A3 (bg) | 1980-05-15 |
| GB1595745A (en) | 1981-08-19 |
| US4087527A (en) | 1978-05-02 |
| CA1097631A (en) | 1981-03-17 |
| PH13147A (en) | 1979-12-18 |
| ES467189A1 (es) | 1979-08-16 |
| NL7801927A (nl) | 1978-08-29 |
| IT7820417A0 (it) | 1978-02-20 |
| US4075206A (en) | 1978-02-21 |
| AU3343378A (en) | 1979-08-30 |
| FR2381767A1 (fr) | 1978-09-22 |
| DD134871A5 (de) | 1979-03-28 |
| SE7802024L (sv) | 1978-08-26 |
| AT361489B (de) | 1981-03-10 |
| IT1094215B (it) | 1985-07-26 |
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