HRP931066A2 - Heterocyclic compounds - Google Patents
Heterocyclic compounds Download PDFInfo
- Publication number
- HRP931066A2 HRP931066A2 HR931066A HRP931066A HRP931066A2 HR P931066 A2 HRP931066 A2 HR P931066A2 HR 931066 A HR931066 A HR 931066A HR P931066 A HRP931066 A HR P931066A HR P931066 A2 HRP931066 A2 HR P931066A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- carbazole
- carboxylate
- aryl
- dimethylpyrrolo
- Prior art date
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 99
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 29
- -1 CH2OR9 Chemical group 0.000 claims description 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000002252 acyl group Chemical group 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 239000000543 intermediate Substances 0.000 claims description 15
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- IMEDANNZZZGSJH-UHFFFAOYSA-N 1,10-dimethylpyrrolo[3,2-b]carbazole-2-carboxylic acid Chemical compound C12=CC=CC=C2N=C2C1=CC1=NC(C(O)=O)=C(C)C1=C2C IMEDANNZZZGSJH-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 101100134927 Gallus gallus COR8 gene Proteins 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 4
- BLBVUHOUIVNYLH-UHFFFAOYSA-N 1,8,10-trimethylpyrrolo[3,2-b]carbazole-2-carboxylic acid Chemical compound C12=CC=CC(C)=C2N=C2C1=CC1=NC(C(O)=O)=C(C)C1=C2C BLBVUHOUIVNYLH-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- ZEIXVWCPBXQYER-UHFFFAOYSA-N benzyl 1,10-dimethylpyrrolo[3,2-b]carbazole-2-carboxylate Chemical compound N1=C2C=C3C4=CC=CC=C4N=C3C(C)=C2C(C)=C1C(=O)OCC1=CC=CC=C1 ZEIXVWCPBXQYER-UHFFFAOYSA-N 0.000 claims description 3
- JWQRICBZPVNCDX-UHFFFAOYSA-N benzyl 1,8,10-trimethylpyrrolo[3,2-b]carbazole-2-carboxylate Chemical compound N1=C2C=C3C4=CC=CC(C)=C4N=C3C(C)=C2C(C)=C1C(=O)OCC1=CC=CC=C1 JWQRICBZPVNCDX-UHFFFAOYSA-N 0.000 claims description 3
- XZOQKAOJDCSKKG-UHFFFAOYSA-N benzyl 6-methoxy-1,10-dimethylpyrrolo[3,2-b]carbazole-2-carboxylate Chemical compound C12=CC(OC)=CC=C2N=C(C(=C2C=3C)C)C1=CC2=NC=3C(=O)OCC1=CC=CC=C1 XZOQKAOJDCSKKG-UHFFFAOYSA-N 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- RSGRGCAHKSQISR-UHFFFAOYSA-N ethyl 1,10-dimethylpyrrolo[3,2-b]carbazole-2-carboxylate Chemical compound C1=CC=C2C3=CC4=NC(C(=O)OCC)=C(C)C4=C(C)C3=NC2=C1 RSGRGCAHKSQISR-UHFFFAOYSA-N 0.000 claims description 3
- SZJDPYZGJCKQBI-UHFFFAOYSA-N ethyl 6-methoxy-1,10-dimethylpyrrolo[3,2-b]carbazole-2-carboxylate Chemical compound C1=C(OC)C=C2C3=CC4=NC(C(=O)OCC)=C(C)C4=C(C)C3=NC2=C1 SZJDPYZGJCKQBI-UHFFFAOYSA-N 0.000 claims description 3
- UQFYDIXELVLPMP-UHFFFAOYSA-N pyridin-3-yl 1,10-dimethylpyrrolo[3,2-b]carbazole-2-carboxylate Chemical compound CC1=C(C(=C2N=C3C=CC=CC3=C2C=2)C)C=2N=C1C(=O)OC1=CC=CN=C1 UQFYDIXELVLPMP-UHFFFAOYSA-N 0.000 claims description 3
- AFLBOPRWNGGXRJ-UHFFFAOYSA-N (1,10-dimethylpyrrolo[3,2-b]carbazol-2-yl)-imidazol-1-ylmethanone Chemical compound N1=C2C=C3C4=CC=CC=C4N=C3C(C)=C2C(C)=C1C(=O)N1C=CN=C1 AFLBOPRWNGGXRJ-UHFFFAOYSA-N 0.000 claims description 2
- ZKNJJSIPGNAJSV-UHFFFAOYSA-N 6-fluoro-1,10-dimethylpyrrolo[3,2-b]carbazole-2-carboxylic acid Chemical compound C12=CC(F)=CC=C2N=C2C1=CC1=NC(C(O)=O)=C(C)C1=C2C ZKNJJSIPGNAJSV-UHFFFAOYSA-N 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- LURYBIXRRCZRFU-UHFFFAOYSA-N ethyl 1,8,10-trimethylpyrrolo[3,2-b]carbazole-2-carboxylate Chemical compound C12=CC3=NC(C(=O)OCC)=C(C)C3=C(C)C2=NC2=C1C=CC=C2C LURYBIXRRCZRFU-UHFFFAOYSA-N 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 2
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 2
- OTYVXROCDIYHNZ-UHFFFAOYSA-O CCOC(C1=CC(C(C(C=C2C)=C3)=CC4=C3NC=C4)=C2[S+]1C)=O Chemical compound CCOC(C1=CC(C(C(C=C2C)=C3)=CC4=C3NC=C4)=C2[S+]1C)=O OTYVXROCDIYHNZ-UHFFFAOYSA-O 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 152
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 123
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 62
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 238000006243 chemical reaction Methods 0.000 description 49
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 235000019439 ethyl acetate Nutrition 0.000 description 42
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 38
- 239000000203 mixture Substances 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 32
- 239000007787 solid Substances 0.000 description 32
- 210000004027 cell Anatomy 0.000 description 29
- 239000000243 solution Substances 0.000 description 29
- UPFNDLSNGMNHKG-UHFFFAOYSA-N (3-acetyl-1h-pyrrol-2-yl)methyl acetate Chemical compound CC(=O)OCC=1NC=CC=1C(C)=O UPFNDLSNGMNHKG-UHFFFAOYSA-N 0.000 description 28
- 239000004927 clay Substances 0.000 description 23
- 239000000377 silicon dioxide Substances 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000013078 crystal Substances 0.000 description 19
- 238000010992 reflux Methods 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 18
- 238000001914 filtration Methods 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 16
- 238000001953 recrystallisation Methods 0.000 description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 15
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 14
- 238000004587 chromatography analysis Methods 0.000 description 14
- 238000009472 formulation Methods 0.000 description 14
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 12
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 10
- 230000008025 crystallization Effects 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 239000002246 antineoplastic agent Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- GNPYCICLAJBJIL-UHFFFAOYSA-N pyrrolo[3,2-b]carbazole Chemical compound C1=CC=C2C3=CC4=NC=CC4=CC3=NC2=C1 GNPYCICLAJBJIL-UHFFFAOYSA-N 0.000 description 5
- ZICUQTHEODRXHW-UHFFFAOYSA-N pyrrolo[3,2-b]carbazole-2-carboxylic acid Chemical class C1=CC=C2C3=CC4=NC(C(=O)O)=CC4=CC3=NC2=C1 ZICUQTHEODRXHW-UHFFFAOYSA-N 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- BLRHMMGNCXNXJL-UHFFFAOYSA-N 1-methylindole Chemical compound C1=CC=C2N(C)C=CC2=C1 BLRHMMGNCXNXJL-UHFFFAOYSA-N 0.000 description 4
- AARVNZRTEHCDFL-UHFFFAOYSA-N 2-(1-benzothiophen-3-ylmethyl)-1h-pyrrole Chemical compound C=1SC2=CC=CC=C2C=1CC1=CC=CN1 AARVNZRTEHCDFL-UHFFFAOYSA-N 0.000 description 4
- GLZKABLKLDYZNY-UHFFFAOYSA-N 3-(1h-pyrrol-2-ylmethyl)-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1CC1=CC=CN1 GLZKABLKLDYZNY-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000013375 chromatographic separation Methods 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ZATIOUPWFZDOQJ-UHFFFAOYSA-N (3-acetyl-5-methyl-1H-pyrrol-2-yl) acetate Chemical compound CC(=O)OC1=C(C=C(C)N1)C(C)=O ZATIOUPWFZDOQJ-UHFFFAOYSA-N 0.000 description 3
- HCUARRIEZVDMPT-UHFFFAOYSA-M 1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)[O-])=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-M 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 230000002045 lasting effect Effects 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- YMIQLVJVEAAUBI-UHFFFAOYSA-N (3,5-diacetyl-4-methyl-1h-pyrrol-2-yl)methyl acetate Chemical compound CC(=O)OCC=1NC(C(C)=O)=C(C)C=1C(C)=O YMIQLVJVEAAUBI-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- FRZLITKMSGOSQH-UHFFFAOYSA-N 2-(1-benzofuran-2-ylmethyl)-1h-pyrrole Chemical compound C=1C2=CC=CC=C2OC=1CC1=CC=CN1 FRZLITKMSGOSQH-UHFFFAOYSA-N 0.000 description 2
- VPEGMKDOJGRBHW-UHFFFAOYSA-N 2-(chloromethyl)-1h-pyrrole Chemical compound ClCC1=CC=CN1 VPEGMKDOJGRBHW-UHFFFAOYSA-N 0.000 description 2
- OJFOWGWQOFZNNJ-UHFFFAOYSA-N 3,4-dimethyl-1h-pyrrole Chemical compound CC1=CNC=C1C OJFOWGWQOFZNNJ-UHFFFAOYSA-N 0.000 description 2
- ODFFPRGJZRXNHZ-UHFFFAOYSA-N 5-fluoroindole Chemical compound FC1=CC=C2NC=CC2=C1 ODFFPRGJZRXNHZ-UHFFFAOYSA-N 0.000 description 2
- DWAQDRSOVMLGRQ-UHFFFAOYSA-N 5-methoxyindole Chemical compound COC1=CC=C2NC=CC2=C1 DWAQDRSOVMLGRQ-UHFFFAOYSA-N 0.000 description 2
- YYFFEPUCAKVRJX-UHFFFAOYSA-N 6-fluoro-1h-indole Chemical compound FC1=CC=C2C=CNC2=C1 YYFFEPUCAKVRJX-UHFFFAOYSA-N 0.000 description 2
- KGWPHCDTOLQQEP-UHFFFAOYSA-N 7-methylindole Chemical compound CC1=CC=CC2=C1NC=C2 KGWPHCDTOLQQEP-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- 201000008808 Fibrosarcoma Diseases 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
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- YWYGOADDCRYNLL-UHFFFAOYSA-N benzyl 1,3,9,10-tetramethylpyrrolo[3,2-b]carbazole-2-carboxylate Chemical compound CN1C2=CC=3C4=CC=CC=C4N(C)C=3C(C)=C2C(C)=C1C(=O)OCC1=CC=CC=C1 YWYGOADDCRYNLL-UHFFFAOYSA-N 0.000 description 1
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- NHSKAPZNFROCIQ-UHFFFAOYSA-N benzyl 1-(3-methoxy-3-oxopropyl)-10-methylpyrrolo[3,2-b]carbazole-2-carboxylate Chemical compound N1=C2C=C3C4=CC=CC=C4N=C3C(C)=C2C(CCC(=O)OC)=C1C(=O)OCC1=CC=CC=C1 NHSKAPZNFROCIQ-UHFFFAOYSA-N 0.000 description 1
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- SYCWDRSTRARGJC-UHFFFAOYSA-N benzyl 4-acetyl-5-(acetyloxymethyl)-3-(3-methoxy-3-oxopropyl)-1h-pyrrole-2-carboxylate Chemical compound N1C(COC(C)=O)=C(C(C)=O)C(CCC(=O)OC)=C1C(=O)OCC1=CC=CC=C1 SYCWDRSTRARGJC-UHFFFAOYSA-N 0.000 description 1
- IZOZYPGIBDWMAW-UHFFFAOYSA-N benzyl 4-acetyl-5-(acetyloxymethyl)-3-methyl-1h-pyrrole-2-carboxylate Chemical compound CC(=O)C1=C(COC(=O)C)NC(C(=O)OCC=2C=CC=CC=2)=C1C IZOZYPGIBDWMAW-UHFFFAOYSA-N 0.000 description 1
- OYFSTPQSFXJDEW-UHFFFAOYSA-N benzyl 7-fluoro-1,10-dimethylpyrrolo[3,2-b]carbazole-2-carboxylate Chemical compound N1=C2C=C3C4=CC=C(F)C=C4N=C3C(C)=C2C(C)=C1C(=O)OCC1=CC=CC=C1 OYFSTPQSFXJDEW-UHFFFAOYSA-N 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- 238000004364 calculation method Methods 0.000 description 1
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- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
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- 229910052801 chlorine Inorganic materials 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
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- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
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- 239000003085 diluting agent Substances 0.000 description 1
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- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
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- LGQZNZVRAIIGDT-UHFFFAOYSA-N ethyl 1,9,10-trimethyl-3h-pyrrolo[3,2-b]carbazole-2-carboxylate Chemical compound C12=CC=CC=C2N(C)C2=C1C=C1NC(C(=O)OCC)=C(C)C1=C2C LGQZNZVRAIIGDT-UHFFFAOYSA-N 0.000 description 1
- HIONMXUNLZOQBT-UHFFFAOYSA-N ethyl 1-ethyl-10-methylpyrrolo[3,2-b]carbazole-2-carboxylate Chemical compound C1=CC=C2C3=CC4=NC(C(=O)OCC)=C(CC)C4=C(C)C3=NC2=C1 HIONMXUNLZOQBT-UHFFFAOYSA-N 0.000 description 1
- DLMCQCIQUKOJBU-UHFFFAOYSA-N ethyl 2-azido-3-(9h-fluoren-2-yl)prop-2-enoate Chemical compound C1=CC=C2C3=CC=C(C=C(C(=O)OCC)N=[N+]=[N-])C=C3CC2=C1 DLMCQCIQUKOJBU-UHFFFAOYSA-N 0.000 description 1
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- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929215361A GB9215361D0 (en) | 1992-07-20 | 1992-07-20 | Heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP931066A2 true HRP931066A2 (en) | 1995-12-31 |
Family
ID=10718981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR931066A HRP931066A2 (en) | 1992-07-20 | 1993-07-19 | Heterocyclic compounds |
Country Status (23)
| Country | Link |
|---|---|
| EP (1) | EP0651750A1 (es) |
| JP (1) | JPH08502037A (es) |
| KR (1) | KR950702563A (es) |
| CN (1) | CN1088209A (es) |
| AU (1) | AU4579593A (es) |
| BG (1) | BG99359A (es) |
| CA (1) | CA2140662A1 (es) |
| CZ (1) | CZ14995A3 (es) |
| FI (1) | FI950229A (es) |
| GB (1) | GB9215361D0 (es) |
| HR (1) | HRP931066A2 (es) |
| HU (1) | HUT76787A (es) |
| IL (1) | IL106385A0 (es) |
| MX (1) | MX9304355A (es) |
| NO (1) | NO950202D0 (es) |
| NZ (1) | NZ254207A (es) |
| PL (1) | PL307169A1 (es) |
| RU (1) | RU95104939A (es) |
| SI (1) | SI9300390A (es) |
| SK (1) | SK7595A3 (es) |
| WO (1) | WO1994002483A1 (es) |
| YU (1) | YU50293A (es) |
| ZA (1) | ZA935213B (es) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9401921D0 (en) * | 1994-02-01 | 1994-03-30 | Wellcome Found | Heterocyclic compounds |
| GB9413758D0 (en) * | 1994-07-07 | 1994-08-24 | Wellcome Found | Heterocyclic compounds |
| GB9804343D0 (en) * | 1998-02-27 | 1998-04-22 | Univ Cardiff | Chemical compounds |
| US7419992B2 (en) | 2001-02-14 | 2008-09-02 | Wisconsin Alumni Research Foundation | Use of aryl hydrocarbon receptor ligand as a therapeutic intervention in angiogenesis-implicated disorders |
| ATE431823T1 (de) * | 2001-02-14 | 2009-06-15 | Wisconsin Alumni Res Found | Zubereitungen und verwendung eines ah-rezeptor- liganden, 2-(1'h-indol-3'-carbonyl)-thiazol-4- carbonsäure-methylester |
| GB0302094D0 (en) | 2003-01-29 | 2003-02-26 | Pharmagene Lab Ltd | EP4 receptor antagonists |
| GB0324269D0 (en) | 2003-10-16 | 2003-11-19 | Pharmagene Lab Ltd | EP4 receptor antagonists |
| WO2008051523A2 (en) * | 2006-10-23 | 2008-05-02 | Georgetown University | Carbazole derivatives useful as medicaments in cancer therapy |
| JP2012500197A (ja) | 2008-08-15 | 2012-01-05 | ジョージタウン ユニバーシティー | Ｒａｓｓｆ１ａ発現およびヒト癌細胞増殖の蛍光調節剤 |
| JP2012051804A (ja) * | 2008-12-26 | 2012-03-15 | Kyoto Univ | Ｅｇ５阻害剤 |
| KR20160066490A (ko) * | 2014-12-02 | 2016-06-10 | 주식회사 씨앤드씨신약연구소 | 헤테로사이클 유도체 및 그의 용도 |
| US11053255B2 (en) | 2015-06-22 | 2021-07-06 | Georgetown University | Synthesis of mahanine and related compounds |
| CN109776550B (zh) * | 2019-01-17 | 2021-08-10 | 广东轻工职业技术学院 | 一种海洋真菌来源的生物碱化合物及其在制备食品防腐剂中的应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0300688A1 (en) * | 1987-07-21 | 1989-01-25 | FISONS plc | Pyrrole derivatives, process for their preparation and pharmaceutical compositions containing them |
| US5166204A (en) * | 1989-11-01 | 1992-11-24 | Toyama Chemical Co., Ltd. | Isoindole derivatives and salts thereof and antitumor agent comprising the same |
| MC2251A1 (fr) * | 1990-03-20 | 1993-03-25 | Wellcome Found | Composes heterocycliques biocides,leur synthese et leurs internediaires,compositions les contenant et leur utilisation en medecine |
-
1992
- 1992-07-20 GB GB929215361A patent/GB9215361D0/en active Pending
-
1993
- 1993-07-19 SI SI9300390A patent/SI9300390A/sl unknown
- 1993-07-19 HU HU9500171A patent/HUT76787A/hu unknown
- 1993-07-19 WO PCT/GB1993/001512 patent/WO1994002483A1/en not_active Application Discontinuation
- 1993-07-19 IL IL106385A patent/IL106385A0/xx unknown
- 1993-07-19 CN CN93116598A patent/CN1088209A/zh active Pending
- 1993-07-19 CA CA002140662A patent/CA2140662A1/en not_active Abandoned
- 1993-07-19 ZA ZA935213A patent/ZA935213B/xx unknown
- 1993-07-19 CZ CZ95149A patent/CZ14995A3/cs unknown
- 1993-07-19 MX MX9304355A patent/MX9304355A/es not_active IP Right Cessation
- 1993-07-19 PL PL93307169A patent/PL307169A1/xx unknown
- 1993-07-19 NZ NZ254207A patent/NZ254207A/en unknown
- 1993-07-19 HR HR931066A patent/HRP931066A2/hr not_active Application Discontinuation
- 1993-07-19 EP EP93916105A patent/EP0651750A1/en not_active Withdrawn
- 1993-07-19 JP JP6504272A patent/JPH08502037A/ja active Pending
- 1993-07-19 SK SK75-95A patent/SK7595A3/sk unknown
- 1993-07-19 RU RU95104939/04A patent/RU95104939A/ru unknown
- 1993-07-19 AU AU45795/93A patent/AU4579593A/en not_active Abandoned
- 1993-07-19 KR KR1019950700226A patent/KR950702563A/ko not_active Application Discontinuation
- 1993-07-20 YU YU50293A patent/YU50293A/sh unknown
-
1995
- 1995-01-18 BG BG99359A patent/BG99359A/bg unknown
- 1995-01-19 FI FI950229A patent/FI950229A/fi unknown
- 1995-01-19 NO NO950202A patent/NO950202D0/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1088209A (zh) | 1994-06-22 |
| YU50293A (sh) | 1997-01-08 |
| CA2140662A1 (en) | 1994-02-03 |
| NO950202L (no) | 1995-01-19 |
| GB9215361D0 (en) | 1992-09-02 |
| NO950202D0 (no) | 1995-01-19 |
| FI950229A0 (fi) | 1995-01-19 |
| CZ14995A3 (en) | 1995-10-18 |
| HU9500171D0 (en) | 1995-03-28 |
| SK7595A3 (en) | 1995-07-11 |
| PL307169A1 (en) | 1995-05-15 |
| JPH08502037A (ja) | 1996-03-05 |
| MX9304355A (es) | 1994-04-29 |
| SI9300390A (en) | 1994-03-31 |
| RU95104939A (ru) | 1996-10-27 |
| WO1994002483A1 (en) | 1994-02-03 |
| FI950229A (fi) | 1995-03-10 |
| ZA935213B (en) | 1995-01-19 |
| AU4579593A (en) | 1994-02-14 |
| KR950702563A (ko) | 1995-07-29 |
| NZ254207A (en) | 1997-03-24 |
| HUT76787A (en) | 1997-11-28 |
| BG99359A (bg) | 1995-11-30 |
| EP0651750A1 (en) | 1995-05-10 |
| IL106385A0 (en) | 1993-11-15 |
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