FI118767B - Uudet akronysiinianalogit, menetelmä niiden valmistamiseksi ja niitä sisältävät farmaseuttiset koostumukset - Google Patents

Uudet akronysiinianalogit, menetelmä niiden valmistamiseksi ja niitä sisältävät farmaseuttiset koostumukset Download PDF

Info

Publication number: FI118767B
Authority: FI; Finland
Prior art keywords: formula; compound; defined above; give; compounds
Prior art date: 1994-02-17

Application number

FI950681A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI950681A0 (fi

FI950681L (fi

Inventor

Yves Rolland

Michel Koch

Francois Tillequin

Alexios-Leandros Skaltsounis

Alain Pierre

Ghanem Atassi

Original Assignee

Servier Lab

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.)

1994-02-17

Filing date

1995-02-15

Publication date

2008-03-14

1995-02-15 Application filed by Servier Lab filed Critical Servier Lab

1995-02-15 Publication of FI950681A0 publication Critical patent/FI950681A0/fi

1995-08-18 Publication of FI950681L publication Critical patent/FI950681L/fi

2008-03-14 Application granted granted Critical

2008-03-14 Publication of FI118767B publication Critical patent/FI118767B/fi

Links

150000001875 compounds Chemical class 0.000 title claims description 78
238000002360 preparation method Methods 0.000 title claims description 17
238000000034 method Methods 0.000 title claims description 10
239000008194 pharmaceutical composition Substances 0.000 title claims description 7
230000008569 process Effects 0.000 title description 3
125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
125000002252 acyl group Chemical group 0.000 claims abstract description 11
-1 diastereoisomers Chemical class 0.000 claims abstract description 11
239000002253 acid Substances 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
150000001204 N-oxides Chemical class 0.000 claims abstract description 8
150000003839 salts Chemical class 0.000 claims abstract description 8
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
150000002367 halogens Chemical class 0.000 claims abstract description 6
206010028980 Neoplasm Diseases 0.000 claims description 21
230000000259 anti-tumor effect Effects 0.000 claims description 11
239000002585 base Substances 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
150000008064 anhydrides Chemical class 0.000 claims description 7
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 5
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
238000010992 reflux Methods 0.000 claims description 5
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
229910000489 osmium tetroxide Inorganic materials 0.000 claims description 3
239000012285 osmium tetroxide Substances 0.000 claims description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
125000003158 alcohol group Chemical group 0.000 claims description 2
230000001476 alcoholic effect Effects 0.000 claims description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
239000000010 aprotic solvent Substances 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
150000008050 dialkyl sulfates Chemical class 0.000 claims description 2
150000002009 diols Chemical class 0.000 claims description 2
229910001510 metal chloride Inorganic materials 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
239000003880 polar aprotic solvent Substances 0.000 claims description 2
125000005133 alkynyloxy group Chemical group 0.000 claims 4
125000003342 alkenyl group Chemical group 0.000 claims 3
125000000304 alkynyl group Chemical group 0.000 claims 3
125000005090 alkenylcarbonyl group Chemical group 0.000 claims 2
125000005087 alkynylcarbonyl group Chemical group 0.000 claims 2
239000004480 active ingredient Substances 0.000 claims 1
125000003302 alkenyloxy group Chemical group 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
230000000007 visual effect Effects 0.000 claims 1
150000002430 hydrocarbons Chemical class 0.000 abstract description 4
239000004215 Carbon black (E152) Substances 0.000 abstract 2
125000001475 halogen functional group Chemical group 0.000 abstract 2
229930195733 hydrocarbon Natural products 0.000 abstract 2
150000007513 acids Chemical class 0.000 abstract 1
SMPZPKRDRQOOHT-UHFFFAOYSA-N acronycine Chemical class CN1C2=CC=CC=C2C(=O)C2=C1C(C=CC(C)(C)O1)=C1C=C2OC SMPZPKRDRQOOHT-UHFFFAOYSA-N 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
230000003595 spectral effect Effects 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
210000004027 cell Anatomy 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
ZTKMNYDOFAYRAK-UHFFFAOYSA-N isoacronycine Natural products CN1C2=CC=CC=C2C(=O)C2=C1C=C1OC(C)(C)C=CC1=C2OC ZTKMNYDOFAYRAK-UHFFFAOYSA-N 0.000 description 7
241001465754 Metazoa Species 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
241000699670 Mus sp. Species 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000003480 eluent Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
210000001072 colon Anatomy 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
241001529936 Murinae Species 0.000 description 2
241000699660 Mus musculus Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
201000011510 cancer Diseases 0.000 description 2
239000002775 capsule Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
208000029742 colonic neoplasm Diseases 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
239000012634 fragment Substances 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
208000032839 leukemia Diseases 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000011580 nude mouse model Methods 0.000 description 2
239000002674 ointment Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
239000000829 suppository Substances 0.000 description 2
210000004881 tumor cell Anatomy 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
BPVPHYHXLGNGOO-UHFFFAOYSA-N 4-methyl-4-oxidomorpholin-4-ium;dihydrate Chemical compound O.O.C[N+]1([O-])CCOCC1 BPVPHYHXLGNGOO-UHFFFAOYSA-N 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000605411 Lloydia Species 0.000 description 1
235000019759 Maize starch Nutrition 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
239000012980 RPMI-1640 medium Substances 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
210000000683 abdominal cavity Anatomy 0.000 description 1
230000009471 action Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
150000003797 alkaloid derivatives Chemical class 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
238000003556 assay Methods 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
201000010897 colon adenocarcinoma Diseases 0.000 description 1
238000004737 colorimetric analysis Methods 0.000 description 1
229940125810 compound 20 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
239000002254 cytotoxic agent Substances 0.000 description 1
231100000599 cytotoxic agent Toxicity 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
231100000135 cytotoxicity Toxicity 0.000 description 1
230000003013 cytotoxicity Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
239000012091 fetal bovine serum Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
229960002949 fluorouracil Drugs 0.000 description 1
239000007789 gas Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000002609 medium Substances 0.000 description 1
239000007923 nasal drop Substances 0.000 description 1
229940100662 nasal drops Drugs 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
230000008520 organization Effects 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical class [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
238000005303 weighing Methods 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 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
- C07D491/02—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
- 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
- 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
- C07D491/12—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 three hetero rings
- C07D491/14—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Medicines Containing Plant Substances (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Saccharide Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Peptides Or Proteins (AREA)

FI950681A 1994-02-17 1995-02-15 Uudet akronysiinianalogit, menetelmä niiden valmistamiseksi ja niitä sisältävät farmaseuttiset koostumukset FI118767B (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9401806		1994-02-17
FR9401806A FR2716197B1 (fr)	1994-02-17	1994-02-17	Nouveaux analogues de l'acronycine, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent.

Publications (3)

Publication Number	Publication Date
FI950681A0 FI950681A0 (fi)	1995-02-15
FI950681L FI950681L (fi)	1995-08-18
FI118767B true FI118767B (fi)	2008-03-14

Family

ID=9460176

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI950681A FI118767B (fi)	1994-02-17	1995-02-15	Uudet akronysiinianalogit, menetelmä niiden valmistamiseksi ja niitä sisältävät farmaseuttiset koostumukset

Country Status (17)

Country	Link
US (1)	US5567707A (el)
EP (1)	EP0668281B1 (el)
JP (1)	JP2675271B2 (el)
CN (1)	CN1055926C (el)
AT (1)	ATE191216T1 (el)
AU (1)	AU680080B2 (el)
CA (1)	CA2142560C (el)
DE (1)	DE69515922T2 (el)
DK (1)	DK0668281T3 (el)
ES (1)	ES2146722T3 (el)
FI (1)	FI118767B (el)
FR (1)	FR2716197B1 (el)
GR (1)	GR3033003T3 (el)
NO (1)	NO308472B1 (el)
NZ (1)	NZ270509A (el)
PT (1)	PT668281E (el)
ZA (1)	ZA951334B (el)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6130161A (en)	1997-05-30	2000-10-10	International Business Machines Corporation	Method of forming copper interconnections with enhanced electromigration resistance and reduced defect sensitivity
FR2772765B1 (fr) *	1997-12-19	2000-03-17	Adir	Nouveaux derives de l'acronycine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
FR2856687B1 (fr) *	2003-06-25	2005-09-16	Servier Lab	Nouveaux derives de benzo[a]pyrano[3,2-h]acridin-7-one, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
FR2902792A1 (fr) *	2006-06-21	2007-12-28	Servier Lab	Nouveaux derives cinnamates de tetrahydro-7h-pyrano(2,3-c)acridin-7-one, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

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US3624087A (en) *	1967-07-17	1971-11-30	Lilly Co Eli	Synthesis of acronycine and related compounds
US3621041A (en) *	1968-07-05	1971-11-16	Lilly Co Eli	Chromans
US3673163A (en) *	1970-06-16	1972-06-27	Lilly Co Eli	Pharmacological preparation containing an acronycine-polyvinylprrolidone coprecipitate
US3657249A (en) *	1970-10-12	1972-04-18	Lilly Co Eli	Synthesis of nordihydroacronycine and related compounds
US3715359A (en) *	1971-07-02	1973-02-06	Lilly Co Eli	Hydroxylated acronycine
US3943137A (en) *	1973-07-09	1976-03-09	University Of Kansas Endowment Association	Acronycine derivatives

1994
- 1994-02-17 FR FR9401806A patent/FR2716197B1/fr not_active Expired - Fee Related
1995
- 1995-02-15 EP EP95400314A patent/EP0668281B1/fr not_active Expired - Lifetime
- 1995-02-15 DE DE69515922T patent/DE69515922T2/de not_active Expired - Fee Related
- 1995-02-15 ES ES95400314T patent/ES2146722T3/es not_active Expired - Lifetime
- 1995-02-15 CA CA002142560A patent/CA2142560C/fr not_active Expired - Fee Related
- 1995-02-15 AT AT95400314T patent/ATE191216T1/de not_active IP Right Cessation
- 1995-02-15 DK DK95400314T patent/DK0668281T3/da active
- 1995-02-15 PT PT95400314T patent/PT668281E/pt unknown
- 1995-02-15 JP JP7026866A patent/JP2675271B2/ja not_active Expired - Fee Related
- 1995-02-15 FI FI950681A patent/FI118767B/fi active
- 1995-02-16 US US08/389,798 patent/US5567707A/en not_active Expired - Lifetime
- 1995-02-16 NO NO950574A patent/NO308472B1/no unknown
- 1995-02-16 AU AU12287/95A patent/AU680080B2/en not_active Ceased
- 1995-02-16 NZ NZ270509A patent/NZ270509A/en not_active IP Right Cessation
- 1995-02-17 ZA ZA951334A patent/ZA951334B/xx unknown
- 1995-02-17 CN CN95102005A patent/CN1055926C/zh not_active Expired - Fee Related
2000
- 2000-03-30 GR GR20000400612T patent/GR3033003T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPH07252257A (ja)	1995-10-03
NZ270509A (en)	1996-03-26
GR3033003T3 (en)	2000-07-31
FI950681A0 (fi)	1995-02-15
FR2716197B1 (fr)	1996-04-19
PT668281E (pt)	2000-07-31
ZA951334B (en)	1995-10-23
US5567707A (en)	1996-10-22
AU680080B2 (en)	1997-07-17
CN1055926C (zh)	2000-08-30
FR2716197A1 (fr)	1995-08-18
NO308472B1 (no)	2000-09-18
NO950574D0 (no)	1995-02-16
CA2142560C (fr)	2002-04-09
NO950574L (no)	1995-08-18
JP2675271B2 (ja)	1997-11-12
DE69515922D1 (de)	2000-05-04
CA2142560A1 (fr)	1995-08-18
CN1113490A (zh)	1995-12-20
ES2146722T3 (es)	2000-08-16
FI950681L (fi)	1995-08-18
DK0668281T3 (da)	2000-08-14
EP0668281A1 (fr)	1995-08-23
AU1228795A (en)	1995-08-24
EP0668281B1 (fr)	2000-03-29
DE69515922T2 (de)	2000-11-02
ATE191216T1 (de)	2000-04-15

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