CA2161980A1 - Derives de substitution de methylenedioxy¬3',4':6,7|indolizino-¬1,2-b|quinolinones - Google Patents

Derives de substitution de methylenedioxy¬3',4':6,7|indolizino-¬1,2-b|quinolinones

Info

Publication number: CA2161980A1
Authority: CA; Canada
Prior art keywords: indolizino; methyldioxolo; quinolin; compound; acetyl
Prior art date: 1993-05-03
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002161980A

Other languages

English (en)

Inventor

William Dennis Kingsbury

Israil Pendrak

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

SmithKline Beecham Corp

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1993-05-03

Filing date

1994-05-03

Publication date

1994-11-10

1994-05-03 Application filed by Individual filed Critical Individual

1994-11-10 Publication of CA2161980A1 publication Critical patent/CA2161980A1/fr

Status Abandoned legal-status Critical Current

Links

-1 methylenedioxy Chemical group 0.000 title description 9
229930185107 quinolinone Natural products 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 21
238000000034 method Methods 0.000 claims abstract description 15
208000036142 Viral infection Diseases 0.000 claims abstract description 7
239000000203 mixture Chemical class 0.000 claims abstract description 7
230000009385 viral infection Effects 0.000 claims abstract description 7
150000003839 salts Chemical class 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
239000003085 diluting agent Substances 0.000 claims description 7
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
241000700605 Viruses Species 0.000 claims description 5
150000001450 anions Chemical class 0.000 claims description 4
XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 3
241000701085 Human alphaherpesvirus 3 Species 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
241000700588 Human alphaherpesvirus 1 Species 0.000 claims description 2
241000701074 Human alphaherpesvirus 2 Species 0.000 claims description 2
YJSPDKPPDSKBQZ-UHFFFAOYSA-N 11h-indolizino[1,2-b]quinolin-9-one Chemical compound C1=CC=C2C=C(CN3C(=O)C=CC=C33)C3=NC2=C1 YJSPDKPPDSKBQZ-UHFFFAOYSA-N 0.000 claims 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
241000124008 Mammalia Species 0.000 claims 4
VTGUUCRUFRWKHF-UHFFFAOYSA-N C1=C2C(CN(C)C)=C(CN3C(C(C)=C(C(C)=O)C=C33)=O)C3=NC2=CC2=C1OCO2 Chemical compound C1=C2C(CN(C)C)=C(CN3C(C(C)=C(C(C)=O)C=C33)=O)C3=NC2=CC2=C1OCO2 VTGUUCRUFRWKHF-UHFFFAOYSA-N 0.000 claims 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
XTTRRRKQNATISH-UHFFFAOYSA-N C1=C2C=C(CN3C4=CC(=C(C3=O)C)C(=O)C)C4=NC2=CC2=C1OCO2 Chemical compound C1=C2C=C(CN3C4=CC(=C(C3=O)C)C(=O)C)C4=NC2=CC2=C1OCO2 XTTRRRKQNATISH-UHFFFAOYSA-N 0.000 claims 2
238000009472 formulation Methods 0.000 claims 2
229910052757 nitrogen Inorganic materials 0.000 claims 2
WLMQWLDCEDBSBK-UHFFFAOYSA-N C(C)(=O)C1=C(C(N2CC=3C(=NC=4C=C5C(=CC=4C=3CO)OCO5)C2=C1)=O)C Chemical compound C(C)(=O)C1=C(C(N2CC=3C(=NC=4C=C5C(=CC=4C=3CO)OCO5)C2=C1)=O)C WLMQWLDCEDBSBK-UHFFFAOYSA-N 0.000 claims 1
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239000003937 drug carrier Substances 0.000 claims 1
241001529453 unidentified herpesvirus Species 0.000 claims 1
230000000840 anti-viral effect Effects 0.000 abstract description 8
NGLARVHWMFXVQC-UHFFFAOYSA-N C1=CC=CC2=C3N=C4C=C5OCOC5C(=O)C4=CC3=CN21 Chemical class C1=CC=CC2=C3N=C4C=C5OCOC5C(=O)C4=CC3=CN21 NGLARVHWMFXVQC-UHFFFAOYSA-N 0.000 abstract 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 33
239000007787 solid Substances 0.000 description 29
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
238000005481 NMR spectroscopy Methods 0.000 description 22
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
229910001868 water Inorganic materials 0.000 description 21
239000002904 solvent Substances 0.000 description 19
101150041968 CDC13 gene Proteins 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
125000003118 aryl group Chemical group 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
210000004027 cell Anatomy 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
239000007788 liquid Substances 0.000 description 10
125000004076 pyridyl group Chemical group 0.000 description 10
239000000377 silicon dioxide Substances 0.000 description 10
239000002253 acid Substances 0.000 description 9
230000000694 effects Effects 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
125000005493 quinolyl group Chemical group 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
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150000002500 ions Chemical class 0.000 description 7
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
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235000019439 ethyl acetate Nutrition 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
125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
239000007832 Na2SO4 Substances 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
239000003443 antiviral agent Substances 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
125000004494 ethyl ester group Chemical group 0.000 description 4
238000001990 intravenous administration Methods 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
230000003612 virological effect Effects 0.000 description 4
UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
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108010010803 Gelatin Proteins 0.000 description 3
239000012981 Hank's balanced salt solution Substances 0.000 description 3
206010028980 Neoplasm Diseases 0.000 description 3
229910015346 Ni2B Inorganic materials 0.000 description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
WRLJWIVBUPYRTE-UHFFFAOYSA-N [B].[Ni].[Ni] Chemical compound [B].[Ni].[Ni] WRLJWIVBUPYRTE-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
201000011510 cancer Diseases 0.000 description 3
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239000006071 cream Substances 0.000 description 3
239000012091 fetal bovine serum Substances 0.000 description 3
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235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000010410 layer Substances 0.000 description 3
VMWJCFLUSKZZDX-UHFFFAOYSA-N n,n-dimethylmethanamine Chemical compound [CH2]N(C)C VMWJCFLUSKZZDX-UHFFFAOYSA-N 0.000 description 3
229910017604 nitric acid Inorganic materials 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
238000012360 testing method Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
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XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 2
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WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
QDWJUBJKEHXSMT-UHFFFAOYSA-N boranylidynenickel Chemical compound [Ni]#B QDWJUBJKEHXSMT-UHFFFAOYSA-N 0.000 description 2
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RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
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VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
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125000003545 alkoxy group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000001857 anti-mycotic effect Effects 0.000 description 1
239000002543 antimycotic Substances 0.000 description 1
IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 1
229960001948 caffeine Drugs 0.000 description 1
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
OKTJSMMVPCPJKN-YPZZEJLDSA-N carbon-10 atom Chemical group [10C] OKTJSMMVPCPJKN-YPZZEJLDSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
101150008687 clcA gene Proteins 0.000 description 1
229940125797 compound 12 Drugs 0.000 description 1
229940126543 compound 14 Drugs 0.000 description 1
229940126086 compound 21 Drugs 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
229940087451 cytovene Drugs 0.000 description 1
VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000006196 drop Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000009509 drug development Methods 0.000 description 1
230000000531 effect on virus Effects 0.000 description 1
210000002950 fibroblast Anatomy 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
229940075507 glyceryl monostearate Drugs 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
210000003292 kidney cell Anatomy 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid 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
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000001788 mono and diglycerides of fatty acids 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
101150006638 nte1 gene Proteins 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
239000006072 paste Substances 0.000 description 1
244000052769 pathogen Species 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
HTYIXCKSEQQCJO-UHFFFAOYSA-N phenaglycodol Chemical compound CC(C)(O)C(C)(O)C1=CC=C(Cl)C=C1 HTYIXCKSEQQCJO-UHFFFAOYSA-N 0.000 description 1
229940068886 polyethylene glycol 300 Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
229940071643 prefilled syringe Drugs 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
210000004767 rumen Anatomy 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000001384 succinic acid Substances 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
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 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
229940104230 thymidine Drugs 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229940107931 zovirax Drugs 0.000 description 1

Classifications

- 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
- C07D491/22—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 four or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/475—Quinolines; Isoquinolines having an indole ring, e.g. yohimbine, reserpine, strychnine, vinblastine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Virology (AREA)
Epidemiology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA002161980A 1993-05-03 1994-05-03 Derives de substitution de methylenedioxy¬3',4':6,7|indolizino-¬1,2-b|quinolinones Abandoned CA2161980A1 (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US5713393A	1993-05-03	1993-05-03
US05/057,133		1993-05-03
US21365794A	1994-03-15	1994-03-15
US08/213,657		1994-03-15
PCT/US1994/004866 WO1994025465A1 (fr)	1993-05-03	1994-05-03	METHYLENEDIOXY [3',4':6,7]INDOLIZINO[1,2,b]QUINOLINONES A SUBSTITUTIONS

Publications (1)

Publication Number	Publication Date
CA2161980A1 true CA2161980A1 (fr)	1994-11-10

Family

ID=26736111

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002161980A Abandoned CA2161980A1 (fr)	1993-05-03	1994-05-03	Derives de substitution de methylenedioxy¬3',4':6,7\|indolizino-¬1,2-b\|quinolinones

Country Status (7)

Country	Link
EP (1)	EP0699201A1 (fr)
JP (1)	JPH08509742A (fr)
AU (1)	AU684777B2 (fr)
CA (1)	CA2161980A1 (fr)
MX (1)	MX9403275A (fr)
NZ (1)	NZ266094A (fr)
WO (1)	WO1994025465A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5883255A (en) *	1990-10-31	1999-03-16	Smithkline Beecham Corporation	Substituted indolizino 1,2-b!quinolinones

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5829793B2 (ja) *	1975-02-07	1983-06-24	日本ケミフア（株）	７−アルコキシカルボニル−８−メチルインドリジノ〔１，２−ｂ〕キノリン−９（１１Ｈ）−オンの製法
US4981968A (en) *	1987-03-31	1991-01-01	Research Triangle Institute	Synthesis of camptothecin and analogs thereof
CA1332413C (fr) *	1987-06-25	1994-10-11	Kabushiki Kaisha Yakult Honsha	Derives de la campothecine et methode de preparation
US5225404A (en) *	1989-11-06	1993-07-06	New York University	Methods of treating colon tumors with tumor-inhibiting camptothecin compounds
JPH06502642A (ja) *	1990-10-31	1994-03-24	スミスクライン・ビーチャム・コーポレイション	置換インドリジノ［１，２−ｂ］キノリノン
ATE136898T1 (de) *	1991-10-29	1996-05-15	Glaxo Wellcome Inc	Wasserlösliche camptothecinderivate
JPH05191297A (ja) *	1992-01-10	1993-07-30	Fujitsu Ltd	シリアル／パラレル変換回路

1994
- 1994-05-03 AU AU66704/94A patent/AU684777B2/en not_active Ceased
- 1994-05-03 WO PCT/US1994/004866 patent/WO1994025465A1/fr not_active Ceased
- 1994-05-03 NZ NZ266094A patent/NZ266094A/en unknown
- 1994-05-03 EP EP94915450A patent/EP0699201A1/fr not_active Withdrawn
- 1994-05-03 JP JP6524634A patent/JPH08509742A/ja active Pending
- 1994-05-03 CA CA002161980A patent/CA2161980A1/fr not_active Abandoned
- 1994-05-03 MX MX9403275A patent/MX9403275A/es unknown

Also Published As

Publication number	Publication date
NZ266094A (en)	1997-10-24
MX9403275A (es)	1995-01-31
AU684777B2 (en)	1998-01-08
WO1994025465A1 (fr)	1994-11-10
EP0699201A1 (fr)	1996-03-06
EP0699201A4 (fr)	1996-01-22
AU6670494A (en)	1994-11-21
JPH08509742A (ja)	1996-10-15

Publication	Publication Date	Title
EP0394026B1 (fr)	1993-09-29	Formulation contenant un dèrivè imidazo [4,5-c]quinoline
AU705792B2 (en)	1999-06-03	Water-soluble esters of camptothecin compounds
JPH0633268B2 (ja)	1994-05-02	水溶性カンプトテシン類似体
EP0608565A1 (fr)	1994-08-03	Dérivés de la pyridopyrimidine, leur préparation et utilisation
AU8940491A (en)	1992-05-26	Substituted indolizino(1,2-b)quinolinones
JP2000505448A (ja)	2000-05-09	カンプトテシン誘導体及び抗腫瘍剤としてのその利用
WO1993016698A1 (fr)	1993-09-02	FURO[3',4':6,7]INDOLIZINO[1,2-b]QUINOLINONES SUBSTITUEES
IL91128A (en)	1996-01-31	Pharmaceutical compositions containing 5-heteroaryl-or 5-aryl-substituted imidazo (2,1-a) isoquinolines for the prophylactic treatment of late asthma by inhalation administration
US5385911A (en)	1995-01-31	Anti-herpes castanospermine esters
AR036131A1 (es)	2004-08-11	Derivados de benzo (g) quinolina, un proceso para su preparacion, una composicion farmaceutica y el uso de dichos derivados para la fabricacion de un medicamento
CA2161980A1 (fr)	1994-11-10	Derives de substitution de methylenedioxy¬3',4':6,7\|indolizino-¬1,2-b\|quinolinones
US11319273B2 (en)	2022-05-03	Lipophilic curcumin analogs and methods of inhibiting HIV-1, treating latent HIV in the brain, and preventing HIV-mediated cognitive decline and HIV dementia
US5883255A (en)	1999-03-16	Substituted indolizino 1,2-b!quinolinones
US4361700A (en)	1982-11-30	Pyridopyrimidinone derivatives
FI894506A0 (fi)	1989-09-25	Menetelmä valmistaa terapeuttisesti aktiivisia pyrido/1,2-a/indolijohdannaisia
EP0004173B1 (fr)	1982-09-22	2,3-Dihydroimidazo (1,2-c) pyrimidines, leur préparation, compositions les contenant et leur utilisation comme médicaments
AU669958B2 (en)	1996-06-27	Quinoline and naphthyridine prodrugs
JPH10152438A (ja)	1998-06-09	１−アザキサントン誘導体またはその塩の安定化方法および１−アザキサントン誘導体含有組成物
WO1994025030A1 (fr)	1994-11-10	DIOXOLO[4,5-g]FURO[3',4':6,7]INDOLOZINO[1,2-b]QUINOLINONES SUBSTITUEES
WO1995003803A1 (fr)	1995-02-09	FURO[3',4':6,7]INDOLIZINO[1,2-b]QUINOLINONES SUBSTITUEES
WO1993020818A1 (fr)	1993-10-28	INDOLIZINO[1,2-b]QUINOLINONES SUBSTITUEES
FI87217C (fi)	1992-12-10	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara tiopyranodipyrazolderivat
AU4288893A (en)	1993-11-18	Substituted indolizino(1,2-b)quinolinones
JPWO2005011674A1 (ja)	2006-09-14	気管支喘息の予防及び／または治療剤
JPH04128220A (ja)	1992-04-28	抗ヘルペスウイルス剤

Legal Events

Date	Code	Title	Description
2000-05-03	FZDE	Dead