FR2516922A1 - Acides (oxo-4-4h-(1)-benzopyran-8-yl) alcanoiques, sels et derives, preparation et medicament les contenant - Google Patents
Acides (oxo-4-4h-(1)-benzopyran-8-yl) alcanoiques, sels et derives, preparation et medicament les contenant Download PDFInfo
- Publication number
- FR2516922A1 FR2516922A1 FR8122020A FR8122020A FR2516922A1 FR 2516922 A1 FR2516922 A1 FR 2516922A1 FR 8122020 A FR8122020 A FR 8122020A FR 8122020 A FR8122020 A FR 8122020A FR 2516922 A1 FR2516922 A1 FR 2516922A1
- Authority
- FR
- France
- Prior art keywords
- phenyl
- benzopyran
- formula
- lower alkyl
- radical
- Prior art date
- 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.)
- Granted
Links
- 239000002253 acid Substances 0.000 title claims abstract description 31
- 150000007513 acids Chemical class 0.000 title claims abstract description 18
- 239000003814 drug Substances 0.000 title claims abstract description 7
- 229940079593 drug Drugs 0.000 title claims abstract description 4
- 238000002360 preparation method Methods 0.000 title claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 150000002148 esters Chemical class 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 150000001408 amides Chemical class 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 37
- -1 alkali metal salts Chemical class 0.000 claims description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- 150000002825 nitriles Chemical class 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 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
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 2
- 150000002690 malonic acid derivatives Chemical class 0.000 claims description 2
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 2
- 239000011707 mineral Substances 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 235000005985 organic acids Nutrition 0.000 claims 2
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 2
- 229940113083 morpholine Drugs 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 1
- QDLFVXRWLQSBTF-UHFFFAOYSA-N 1,1,2-triethylhydrazine Chemical compound CCNN(CC)CC QDLFVXRWLQSBTF-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- ZAPMTSHEXFEPSD-UHFFFAOYSA-N 4-(2-chloroethyl)morpholine Chemical compound ClCCN1CCOCC1 ZAPMTSHEXFEPSD-UHFFFAOYSA-N 0.000 description 1
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-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
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 229910018663 Mn O Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- 241000831652 Salinivibrio sharmensis Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940100197 antimetabolite Drugs 0.000 description 1
- 239000002256 antimetabolite Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 210000003567 ascitic fluid Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000280 densification Methods 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ZONYXWQDUYMKFB-UHFFFAOYSA-N flavanone Chemical compound O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 description 1
- 229960002949 fluorouracil Drugs 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 208000003747 lymphoid leukemia Diseases 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- RLZZZVKAURTHCP-UHFFFAOYSA-N phenanthrene-3,4-diol Chemical compound C1=CC=C2C3=C(O)C(O)=CC=C3C=CC2=C1 RLZZZVKAURTHCP-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- 235000012222 talc Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
- C07D311/36—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only not hydrogenated in the hetero ring, e.g. isoflavones
-
- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
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- 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)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
- Control Of Motors That Do Not Use Commutators (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (28)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8122020A FR2516922A1 (fr) | 1981-11-25 | 1981-11-25 | Acides (oxo-4-4h-(1)-benzopyran-8-yl) alcanoiques, sels et derives, preparation et medicament les contenant |
| ZA828436A ZA828436B (en) | 1981-11-25 | 1982-11-16 | (oxo-4-4h-(1)-benzopyran-8-yl)alcanoic acids, salts and derivatives,their manufacture and medicines containing them |
| IL67291A IL67291A0 (en) | 1981-11-25 | 1982-11-17 | (4-oxo-4h-(1)-benzopyran-8-yl)alkanoic acids and salts and derivatives thereof,their manufacture and pharmaceutical compositions containing them |
| IE2752/82A IE54130B1 (en) | 1981-11-25 | 1982-11-18 | (4-oxo-4h-(1)-benzopyran-8-yl)-alkanoic acids, salts and derivatives, their manufacture and medicines containing them |
| IN848/DEL/82A IN158843B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-11-25 | 1982-11-18 | |
| AU90730/82A AU563190B2 (en) | 1981-11-25 | 1982-11-19 | 8-carboxyalkyl-4h-benzo(b)pyran-4-ones |
| HU823764A HU192112B (en) | 1981-11-25 | 1982-11-23 | Process for preparing new 4-oxo-4h-/1/-benzo-pyran-8-yl-alkanecarboxylic acids |
| ES517637A ES8308323A1 (es) | 1981-11-25 | 1982-11-24 | Un procedimiento de preparacion de los acidos(oxo-4-4h-(1)-benzopiran-8-il)-alcanoicos. |
| DE8282402137T DE3277970D1 (en) | 1981-11-25 | 1982-11-24 | (4-oxo-4h-(1)-benzopyran-8-yl)-alkanoic acids, salts and derivatives, preparation and medicines containing them |
| FR8219640A FR2536397A2 (en) | 1981-11-25 | 1982-11-24 | [4-oxo-4H-1-Benzopyran-8-yl]alkanoic acids, their salts and derivatives, their preparation and medicinal products containing them |
| CS828426A CS248035B2 (en) | 1981-11-25 | 1982-11-24 | Production method of the(4(oxo-4h)1(-benzopyran-8-yl)carboxyle acides |
| NZ202596A NZ202596A (en) | 1981-11-25 | 1982-11-24 | 4-oxo-4h(1)-benzopyran-8-yl-alkanoic acids,derivatives and pharmaceutical compositions |
| MA19863A MA19650A1 (fr) | 1981-11-25 | 1982-11-24 | Procede de preparation d'acide (oxo-4-4H-(1)-benzopuran-8-yl) |
| SU823516803A SU1250171A3 (ru) | 1981-11-25 | 1982-11-24 | Способ получени производных @ 4-(4н)-оксо-8-бензопиранил @ -уксусной кислоты |
| EP82402137A EP0080934B1 (fr) | 1981-11-25 | 1982-11-24 | Acides (oxo-4-4H-(1)-benzopyran-8-yl) alcanoiques, sels et dérivés, préparation et médicaments les contenant |
| MX010425A MX173498B (es) | 1981-11-25 | 1982-11-24 | Procedimiento para la preparacion de acidos 4£- oxo-4h (1)-benzopiran-8-il| alcanoicos y derivados. |
| DK523082A DK164163C (da) | 1981-11-25 | 1982-11-24 | Analogifremgangsmaade til fremstilling af 4-oxo-4h-oe1aa-benzopyran-8-yl-alkansyrer eller estere eller dialkylaminoalkylamider deraf eller alkalimetalsalte deraf samt 4-oxo-4h-oe1aa-benzopyran-8-yl-alkannitriler til anvendelse som mellemprodukter |
| NO823940A NO159169C (no) | 1981-11-25 | 1982-11-24 | Analogifremgansmaate for fremstilling av derivater av (okso-4-4h-(1)-benzopyran-8-yl)eddiksyre med antitumoral terapeutisk aktivitet. |
| AT82402137T ATE31927T1 (de) | 1981-11-25 | 1982-11-24 | (4-oxo-4h-(1)-benzopyran-8-yl)-alkansaueren, salze und derivate, herstellung und diese enthaltende arzneimittel. |
| MX888182A MX155838A (es) | 1981-11-25 | 1982-11-24 | Procedimiento para la preparacion de acidos(4-oxo-4h(1)-benzopiran-bil)alcandicos y derivados de los mismos |
| OA57850A OA07257A (fr) | 1981-11-25 | 1982-11-25 | Acides (oxo-4-4h-(1)-benzopyran-8-yl) alcanoïque, sels et dérivés, préparation et médicaments les contenant. |
| CA000416354A CA1213595A (fr) | 1981-11-25 | 1982-11-25 | Acides ¬oxo-4-4h-(|-benzopyran-8-yl| alcanoique sels et derives, preparation |
| DD82245217A DD204919A5 (de) | 1981-11-25 | 1982-11-25 | Verfahren zur herstellung von (4-oxo-4h-1-benzopyran-8-yl)-alkancarbonsaeuren und deren alkalimetallsalzen, estern, aminoestern und amiden |
| JP57205582A JPS5896082A (ja) | 1981-11-25 | 1982-11-25 | 〔４−オキソ−４ｈ−〔１〕−ベンゾピラン−８−イル〕アルカン酸およびその誘導体、その製造方法、およびこれを含有する医薬組成物 |
| YU2649/82A YU43726B (en) | 1981-11-25 | 1982-11-25 | Process for obtaining (oxo-4-4h(1)benzopyrane-8-yl-alkanic acids |
| YU1630/84A YU43675B (en) | 1981-11-25 | 1984-09-21 | Process for obtaining derivatives of (oxo-4-4h(1)benzopyrane-8-yl)alcanic acids |
| US06/669,037 US4602034A (en) | 1981-11-25 | 1984-11-06 | (Oxo-4-4H-(1)-benzopyran-8-yl) alkanoic acids, salts and derivatives, their manufacture and medicines containing them |
| US06/872,381 US4783533A (en) | 1981-11-25 | 1986-05-29 | [Oxo-4-4H-[1]-benzopyran-8-yl]alcanoic acids, salts and derivatives, their manufacture and medicines containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8122020A FR2516922A1 (fr) | 1981-11-25 | 1981-11-25 | Acides (oxo-4-4h-(1)-benzopyran-8-yl) alcanoiques, sels et derives, preparation et medicament les contenant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2516922A1 true FR2516922A1 (fr) | 1983-05-27 |
| FR2516922B1 FR2516922B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-02-10 |
Family
ID=9264332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8122020A Granted FR2516922A1 (fr) | 1981-11-25 | 1981-11-25 | Acides (oxo-4-4h-(1)-benzopyran-8-yl) alcanoiques, sels et derives, preparation et medicament les contenant |
Country Status (24)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2536397A2 (en) * | 1981-11-25 | 1984-05-25 | Lipha | [4-oxo-4H-1-Benzopyran-8-yl]alkanoic acids, their salts and derivatives, their preparation and medicinal products containing them |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3311004A1 (de) * | 1983-03-25 | 1984-09-27 | Bayer Ag, 5090 Leverkusen | Chromon- und thiochromon-8-aldehyde, sowie ein verfahren zu ihrer herstellung |
| JPS62215581A (ja) * | 1986-03-18 | 1987-09-22 | Koichi Shiyudo | フラボンカルボン酸誘導体 |
| IL85554A0 (en) * | 1987-03-02 | 1988-08-31 | Takeda Chemical Industries Ltd | Chromone derivatives |
| USH1427H (en) * | 1988-04-06 | 1995-04-04 | Briet; Phillipe | Substituted flavonoid compounds, their salts, their manufacture and their use in combination with interleukin-2 |
| IL89840A (en) * | 1988-04-06 | 1996-10-31 | Lipha | Substituted flavonoid compounds and salts thereof their preparation and pharmaceutical composition containing them |
| US5116954A (en) * | 1988-04-06 | 1992-05-26 | Lipha, Lyonnaise Industrielle Pharmaceutique | Pharmaceutically useful flavonoic compounds containing at least one substituent on the benzopyranone ring moiety |
| US5126129A (en) * | 1988-05-23 | 1992-06-30 | The Government Of The United States Of America As Represented By The Secretary Of The Department Of Health & Human Services | Cancer therapy using interleukin-2 and flavone compounds |
| US5238954A (en) * | 1989-01-19 | 1993-08-24 | The Upjohn Company | Fluorinated flavone acetic acid |
| DE68913997T2 (de) * | 1989-01-19 | 1994-07-28 | Upjohn Co | Fluorierte flavon-essigsäure. |
| SK281016B6 (sk) * | 1992-02-05 | 2000-10-09 | Boehringer Ingelheim Kg | Amidínové deriváty, spôsob ich výroby, použitie a farmaceutické prostriedky s ich obsahom |
| US5703130A (en) * | 1995-06-07 | 1997-12-30 | Institute Of Materia Medica, An Institute Of The Chinese Academy Of Medical Sciences | Chalcone retinoids and methods of use of same |
| US5716982A (en) * | 1995-06-07 | 1998-02-10 | Institute Of Materia Medica, An Institute Of The Chinese Academy Of Medical Sciences | Retinoids and methods of use of same |
| US5968940A (en) * | 1995-06-08 | 1999-10-19 | Institute Of Materia Medica | Retinoids and methods of use of same |
| JP4638098B2 (ja) * | 1999-06-14 | 2011-02-23 | キャンサー・リサーチ・テクノロジー・リミテッド | 癌治療 |
| CA2389924A1 (en) | 2000-01-24 | 2001-07-26 | Jozef S. Mruk | Use of flavone 8-acetic acid in vascular and cardiovascular interventions and acute coronary syndromes |
| AU2001282717A1 (en) * | 2000-07-28 | 2002-02-13 | Cancer Research Technology Limited | Cancer treatment by combination therapy |
| GB0121285D0 (en) * | 2001-09-03 | 2001-10-24 | Cancer Res Ventures Ltd | Anti-cancer combinations |
| GB2386836B (en) * | 2002-03-22 | 2006-07-26 | Cancer Res Ventures Ltd | Anti-cancer combinations |
| GB2394658A (en) * | 2002-11-01 | 2004-05-05 | Cancer Rec Tech Ltd | Oral anti-cancer composition |
| GB0321999D0 (en) * | 2003-09-19 | 2003-10-22 | Cancer Rec Tech Ltd | Anti-cancer combinations |
| JP2009506019A (ja) * | 2005-08-26 | 2009-02-12 | アンティソーマ・ピーエルシー | 癌治療のための組み合わせ |
| WO2011023287A1 (en) | 2009-08-27 | 2011-03-03 | Merck Patent Gmbh | Use of faa and its derivatives in cosmetics and dermatology |
| DK2496567T3 (en) | 2009-11-05 | 2017-10-30 | Rhizen Pharmaceuticals S A | PRESENT UNKNOWN BENZOPYRANKINA MODULATORS |
| CN103304531A (zh) * | 2013-06-25 | 2013-09-18 | 南方医科大学 | 一种3-芳基黄酮乙酸 |
| WO2017156520A1 (en) * | 2016-03-11 | 2017-09-14 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Icariin and icaritin derivatives |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR4092M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1963-10-10 | 1966-04-18 | ||
| FR2255894A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-12-27 | 1975-07-25 | Erba Carlo Spa | |
| FR2281112A1 (fr) * | 1974-08-05 | 1976-03-05 | Lipha | Nouveau medicament choleretique et anti-inflammatoire |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2921070A (en) * | 1957-11-05 | 1960-01-12 | Recordati Lab Farmacologico S | Basic esters of 3-methylflavone-8-carboxylic acid |
| BE757821A (fr) * | 1970-08-01 | 1971-04-01 | Recordati Chem Pharm | Procede de preparation de l'acide 3-propionyl-salicylique et dederives de cet acide |
| US4148900A (en) * | 1973-12-27 | 1979-04-10 | Carlo Erba S.P.A. | 5:6-Benzo-γ-pyrone derivatives and process for their preparation |
| GB1469823A (en) * | 1974-08-13 | 1977-04-06 | Farma Lepori | Flavone derivatives |
| DE2549745A1 (de) * | 1974-11-20 | 1976-05-26 | Lipha | Durch einen chromonylrest substituierte propionsaeuren sowie deren derivate und verwendungen |
-
1981
- 1981-11-25 FR FR8122020A patent/FR2516922A1/fr active Granted
-
1982
- 1982-11-16 ZA ZA828436A patent/ZA828436B/xx unknown
- 1982-11-17 IL IL67291A patent/IL67291A0/xx not_active IP Right Cessation
- 1982-11-18 IN IN848/DEL/82A patent/IN158843B/en unknown
- 1982-11-18 IE IE2752/82A patent/IE54130B1/en not_active IP Right Cessation
- 1982-11-19 AU AU90730/82A patent/AU563190B2/en not_active Ceased
- 1982-11-23 HU HU823764A patent/HU192112B/hu not_active IP Right Cessation
- 1982-11-24 NO NO823940A patent/NO159169C/no unknown
- 1982-11-24 AT AT82402137T patent/ATE31927T1/de not_active IP Right Cessation
- 1982-11-24 MA MA19863A patent/MA19650A1/fr unknown
- 1982-11-24 CS CS828426A patent/CS248035B2/cs unknown
- 1982-11-24 DE DE8282402137T patent/DE3277970D1/de not_active Expired
- 1982-11-24 SU SU823516803A patent/SU1250171A3/ru active
- 1982-11-24 DK DK523082A patent/DK164163C/da not_active IP Right Cessation
- 1982-11-24 ES ES517637A patent/ES8308323A1/es not_active Expired
- 1982-11-24 EP EP82402137A patent/EP0080934B1/fr not_active Expired
- 1982-11-24 MX MX010425A patent/MX173498B/es unknown
- 1982-11-24 NZ NZ202596A patent/NZ202596A/en unknown
- 1982-11-25 CA CA000416354A patent/CA1213595A/fr not_active Expired
- 1982-11-25 YU YU2649/82A patent/YU43726B/xx unknown
- 1982-11-25 DD DD82245217A patent/DD204919A5/de unknown
- 1982-11-25 JP JP57205582A patent/JPS5896082A/ja active Granted
- 1982-11-25 OA OA57850A patent/OA07257A/xx unknown
-
1984
- 1984-09-21 YU YU1630/84A patent/YU43675B/xx unknown
- 1984-11-06 US US06/669,037 patent/US4602034A/en not_active Expired - Fee Related
-
1986
- 1986-05-29 US US06/872,381 patent/US4783533A/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR4092M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1963-10-10 | 1966-04-18 | ||
| FR2255894A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-12-27 | 1975-07-25 | Erba Carlo Spa | |
| FR2281112A1 (fr) * | 1974-08-05 | 1976-03-05 | Lipha | Nouveau medicament choleretique et anti-inflammatoire |
Non-Patent Citations (1)
| Title |
|---|
| CA1973 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2536397A2 (en) * | 1981-11-25 | 1984-05-25 | Lipha | [4-oxo-4H-1-Benzopyran-8-yl]alkanoic acids, their salts and derivatives, their preparation and medicinal products containing them |
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