ZA200510323B - Benzo[B]pyrano[3,2-H]acridin-2-one cinnamate compounds, a process for their preparation and pharmaceutical compositions containing them - Google Patents
Benzo[B]pyrano[3,2-H]acridin-2-one cinnamate compounds, a process for their preparation and pharmaceutical compositions containing them Download PDFInfo
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- ZA200510323B ZA200510323B ZA200510323A ZA200510323A ZA200510323B ZA 200510323 B ZA200510323 B ZA 200510323B ZA 200510323 A ZA200510323 A ZA 200510323A ZA 200510323 A ZA200510323 A ZA 200510323A ZA 200510323 B ZA200510323 B ZA 200510323B
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- South Africa
- Prior art keywords
- branched
- linear
- alkyl
- aryl
- group
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- -1 Benzo[B]pyrano[3,2-H]acridin-2-one cinnamate compounds Chemical class 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title description 49
- 238000000034 method Methods 0.000 title description 48
- 239000008194 pharmaceutical composition Substances 0.000 title description 11
- 230000008569 process Effects 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 52
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 15
- 125000005843 halogen group Chemical group 0.000 claims abstract description 12
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 10
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 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 4
- 150000004677 hydrates Chemical class 0.000 claims abstract description 4
- 239000012453 solvate Substances 0.000 claims abstract description 4
- 125000002252 acyl group Chemical group 0.000 claims abstract description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 8
- 239000002585 base Substances 0.000 abstract description 6
- 150000007513 acids Chemical class 0.000 abstract description 3
- 125000005605 benzo group Chemical group 0.000 abstract description 3
- 125000002619 bicyclic group Chemical group 0.000 abstract description 2
- 229910003827 NRaRb Inorganic materials 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000000824 cytostatic agent Substances 0.000 abstract 1
- 230000001085 cytostatic effect Effects 0.000 abstract 1
- 230000010534 mechanism of action Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 87
- 239000000047 product Substances 0.000 description 49
- 238000004949 mass spectrometry Methods 0.000 description 32
- UYUXXCRKWXJQED-UHFFFAOYSA-N 3h-acridin-2-one Chemical compound C1=CC=CC2=CC3=CC(=O)CC=C3N=C21 UYUXXCRKWXJQED-UHFFFAOYSA-N 0.000 description 16
- GXLIFJYFGMHYDY-ZZXKWVIFSA-N 4-chlorocinnamic acid Chemical compound OC(=O)\C=C\C1=CC=C(Cl)C=C1 GXLIFJYFGMHYDY-ZZXKWVIFSA-N 0.000 description 15
- 206010028980 Neoplasm Diseases 0.000 description 13
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 11
- 230000000259 anti-tumor effect Effects 0.000 description 10
- 230000009471 action Effects 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 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 description 5
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- 231100000682 maximum tolerated dose Toxicity 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- ZDWOINJTUCUSJQ-XPSQVAKYSA-N [(5R,6R)-5-acetyloxy-11-methoxy-2,7,7-trimethyl-13-oxo-8-oxa-2-azapentacyclo[12.8.0.03,12.04,9.016,21]docosa-1(22),3,9,11,14,16,18,20-octaen-6-yl] 3-naphthalen-1-ylprop-2-enoate Chemical compound C1=CC=C2C=C(C(=O)C=3C(OC)=CC4=C([C@@H](OC(C)=O)[C@@H](OC(=O)C=CC=5C6=CC=CC=C6C=CC=5)C(C)(C)O4)C=3N3C)C3=CC2=C1 ZDWOINJTUCUSJQ-XPSQVAKYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003725 azepanyl group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- 230000022131 cell cycle Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000007398 colorimetric assay Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 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
- 238000011161 development Methods 0.000 description 1
- 125000005959 diazepanyl group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000005584 early death Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 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
- 239000001963 growth medium Substances 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 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
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000005961 oxazepanyl group Chemical group 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229940100445 wheat starch 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
- C07D491/02—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
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0413682A FR2879600B1 (fr) | 2004-12-22 | 2004-12-22 | Nouveaux derives cinnamates de benzo[b]pyrano[3,2-h]acridin-7-one, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200510323B true ZA200510323B (en) | 2006-12-27 |
Family
ID=34954114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200510323A ZA200510323B (en) | 2004-12-22 | 2005-12-20 | Benzo[B]pyrano[3,2-H]acridin-2-one cinnamate compounds, a process for their preparation and pharmaceutical compositions containing them |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US7144891B2 (de) |
| EP (1) | EP1674101B1 (de) |
| JP (1) | JP2006176525A (de) |
| KR (1) | KR100742060B1 (de) |
| CN (1) | CN1796387A (de) |
| AT (1) | ATE378050T1 (de) |
| AU (1) | AU2005247032A1 (de) |
| BR (1) | BRPI0506019A (de) |
| CA (1) | CA2529630A1 (de) |
| CY (1) | CY1107100T1 (de) |
| DE (1) | DE602005003315T2 (de) |
| DK (1) | DK1674101T3 (de) |
| EA (1) | EA010094B1 (de) |
| ES (1) | ES2297648T3 (de) |
| FR (1) | FR2879600B1 (de) |
| HR (1) | HRP20070524T3 (de) |
| MA (1) | MA27965A1 (de) |
| MX (1) | MXPA05013993A (de) |
| MY (1) | MY138045A (de) |
| NO (1) | NO20056091L (de) |
| NZ (1) | NZ544315A (de) |
| PL (1) | PL1674101T3 (de) |
| PT (1) | PT1674101E (de) |
| SG (1) | SG123675A1 (de) |
| SI (1) | SI1674101T1 (de) |
| ZA (1) | ZA200510323B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| FR2795071B1 (fr) * | 1999-06-16 | 2001-07-27 | Adir | Nouveaux derives de carboxylate de 7-oxo-2,3,7,14- tetrahydro-1h-benzo[b]pyrano[3,2,h] acridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US7056929B2 (en) * | 2001-07-25 | 2006-06-06 | Les Laboratoires Servier | Benzo[b]pyrano[3,2-h]acridin-7-one compounds |
| FR2827864B1 (fr) * | 2001-07-25 | 2005-09-16 | Servier Lab | Nouveaux derives de benzo[b]pyrano[3,2-h]acridin-7-one, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
-
2004
- 2004-12-22 FR FR0413682A patent/FR2879600B1/fr not_active Expired - Fee Related
-
2005
- 2005-12-01 SG SG200507683A patent/SG123675A1/en unknown
- 2005-12-07 MA MA28637A patent/MA27965A1/fr unknown
- 2005-12-09 CA CA002529630A patent/CA2529630A1/fr not_active Abandoned
- 2005-12-20 ZA ZA200510323A patent/ZA200510323B/en unknown
- 2005-12-20 MY MYPI20056024A patent/MY138045A/en unknown
- 2005-12-20 MX MXPA05013993A patent/MXPA05013993A/es unknown
- 2005-12-21 US US11/313,386 patent/US7144891B2/en not_active Expired - Fee Related
- 2005-12-21 ES ES05292744T patent/ES2297648T3/es active Active
- 2005-12-21 NZ NZ544315A patent/NZ544315A/en unknown
- 2005-12-21 NO NO20056091A patent/NO20056091L/no not_active Application Discontinuation
- 2005-12-21 EP EP05292744A patent/EP1674101B1/de active Active
- 2005-12-21 EA EA200501845A patent/EA010094B1/ru unknown
- 2005-12-21 SI SI200530108T patent/SI1674101T1/sl unknown
- 2005-12-21 PL PL05292744T patent/PL1674101T3/pl unknown
- 2005-12-21 AT AT05292744T patent/ATE378050T1/de not_active IP Right Cessation
- 2005-12-21 DK DK05292744T patent/DK1674101T3/da active
- 2005-12-21 DE DE602005003315T patent/DE602005003315T2/de not_active Expired - Fee Related
- 2005-12-21 PT PT05292744T patent/PT1674101E/pt unknown
- 2005-12-22 JP JP2005369129A patent/JP2006176525A/ja active Pending
- 2005-12-22 BR BRPI0506019-2A patent/BRPI0506019A/pt not_active IP Right Cessation
- 2005-12-22 CN CNA2005101328156A patent/CN1796387A/zh active Pending
- 2005-12-22 AU AU2005247032A patent/AU2005247032A1/en not_active Abandoned
- 2005-12-22 KR KR1020050128012A patent/KR100742060B1/ko not_active IP Right Cessation
-
2007
- 2007-11-15 HR HR20070524T patent/HRP20070524T3/xx unknown
- 2007-12-19 CY CY20071101611T patent/CY1107100T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE602005003315D1 (de) | 2007-12-27 |
| PL1674101T3 (pl) | 2008-05-30 |
| US20060135545A1 (en) | 2006-06-22 |
| CY1107100T1 (el) | 2012-10-24 |
| ES2297648T3 (es) | 2008-05-01 |
| AU2005247032A1 (en) | 2006-07-06 |
| DK1674101T3 (da) | 2008-03-03 |
| FR2879600A1 (fr) | 2006-06-23 |
| CA2529630A1 (fr) | 2006-06-22 |
| SI1674101T1 (sl) | 2008-04-30 |
| KR100742060B1 (ko) | 2007-07-23 |
| PT1674101E (pt) | 2007-12-17 |
| EA200501845A2 (ru) | 2006-06-30 |
| ATE378050T1 (de) | 2007-11-15 |
| SG123675A1 (en) | 2006-07-26 |
| FR2879600B1 (fr) | 2007-02-09 |
| MXPA05013993A (es) | 2006-06-21 |
| NO20056091L (no) | 2006-06-23 |
| US7144891B2 (en) | 2006-12-05 |
| HRP20070524T3 (en) | 2008-07-31 |
| EP1674101B1 (de) | 2007-11-14 |
| MA27965A1 (fr) | 2006-07-03 |
| CN1796387A (zh) | 2006-07-05 |
| DE602005003315T2 (de) | 2008-09-25 |
| EA010094B1 (ru) | 2008-06-30 |
| EA200501845A3 (ru) | 2006-10-27 |
| KR20060072093A (ko) | 2006-06-27 |
| BRPI0506019A (pt) | 2006-09-19 |
| EP1674101A1 (de) | 2006-06-28 |
| JP2006176525A (ja) | 2006-07-06 |
| MY138045A (en) | 2009-04-30 |
| NZ544315A (en) | 2006-11-30 |
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