ES2245443T3 - Nuevos esteres de acidos fluoreno-carboxilicos, procedimiento para su preparacion, asi como su utilizacion como medicamentos. - Google Patents
Nuevos esteres de acidos fluoreno-carboxilicos, procedimiento para su preparacion, asi como su utilizacion como medicamentos.Info
- Publication number
- ES2245443T3 ES2245443T3 ES03734600T ES03734600T ES2245443T3 ES 2245443 T3 ES2245443 T3 ES 2245443T3 ES 03734600 T ES03734600 T ES 03734600T ES 03734600 T ES03734600 T ES 03734600T ES 2245443 T3 ES2245443 T3 ES 2245443T3
- Authority
- ES
- Spain
- Prior art keywords
- methyl
- compounds
- acid
- hydroxy
- formula
- 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.)
- Expired - Lifetime
Links
- 239000002253 acid Substances 0.000 title claims description 66
- 150000007513 acids Chemical class 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 13
- 239000003814 drug Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title description 10
- 229940079593 drug Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 96
- -1 hydroxy, methyl Chemical group 0.000 claims abstract description 46
- 150000003254 radicals Chemical class 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 17
- 229910052736 halogen Chemical group 0.000 claims abstract description 13
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 11
- 150000002367 halogens Chemical group 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 150000001450 anions Chemical class 0.000 claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 32
- 239000013543 active substance Substances 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- 230000003454 betamimetic effect Effects 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229940043355 kinase inhibitor Drugs 0.000 claims description 7
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003246 corticosteroid Substances 0.000 claims description 6
- 229960001334 corticosteroids Drugs 0.000 claims description 6
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 claims description 6
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 claims description 6
- 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 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims description 5
- 208000007101 Muscle Cramp Diseases 0.000 claims description 4
- 208000005392 Spasm Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000013067 intermediate product Substances 0.000 claims description 3
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 239000005557 antagonist Substances 0.000 claims description 2
- 230000003266 anti-allergic effect Effects 0.000 claims description 2
- 230000036471 bradycardia Effects 0.000 claims description 2
- 208000006218 bradycardia Diseases 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 239000013312 porous aromatic framework Substances 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims description 2
- 210000001635 urinary tract Anatomy 0.000 claims description 2
- 210000001186 vagus nerve Anatomy 0.000 claims description 2
- 206010056344 Menstrual discomfort Diseases 0.000 claims 1
- 230000001713 cholinergic effect Effects 0.000 claims 1
- 230000002496 gastric effect Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 40
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- 239000000126 substance Substances 0.000 description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 150000002148 esters Chemical class 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 238000007792 addition Methods 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 15
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- 239000003380 propellant Substances 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- PUPWRKQSVGUBQS-UHFFFAOYSA-N 9-methylfluorene-9-carboxylic acid Chemical compound C1=CC=C2C(C)(C(O)=O)C3=CC=CC=C3C2=C1 PUPWRKQSVGUBQS-UHFFFAOYSA-N 0.000 description 12
- 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 12
- 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 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- 239000008101 lactose Substances 0.000 description 12
- 229960001375 lactose Drugs 0.000 description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- 238000000746 purification Methods 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 10
- GXAMYUGOODKVRM-UHFFFAOYSA-N Flurecol Chemical compound C1=CC=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 GXAMYUGOODKVRM-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- BHEFSGMUMYBJRZ-UHFFFAOYSA-N 9-fluorofluorene-9-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)(F)C3=CC=CC=C3C2=C1 BHEFSGMUMYBJRZ-UHFFFAOYSA-N 0.000 description 8
- FIMXSEMBHGTNKT-UHFFFAOYSA-N Scopine Natural products CN1C2CC(O)CC1C1C2O1 FIMXSEMBHGTNKT-UHFFFAOYSA-N 0.000 description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 7
- 239000000443 aerosol Substances 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 229960002848 formoterol Drugs 0.000 description 7
- BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical class NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 6
- 229920002261 Corn starch Polymers 0.000 description 6
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 235000015165 citric acid Nutrition 0.000 description 6
- 239000008120 corn starch Substances 0.000 description 6
- 229940099112 cornstarch Drugs 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 239000001530 fumaric acid Substances 0.000 description 6
- 150000004677 hydrates Chemical class 0.000 description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 235000019698 starch Nutrition 0.000 description 6
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 5
- 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 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 5
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- 229940098779 methanesulfonic acid Drugs 0.000 description 5
- 229940102396 methyl bromide Drugs 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 229960004017 salmeterol Drugs 0.000 description 5
- 235000015424 sodium Nutrition 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 229940037001 sodium edetate Drugs 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 235000012222 talc Nutrition 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- 239000011975 tartaric acid Substances 0.000 description 5
- 235000002906 tartaric acid Nutrition 0.000 description 5
- 238000002560 therapeutic procedure Methods 0.000 description 5
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 4
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 description 4
- 239000007995 HEPES buffer Substances 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
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- 230000015572 biosynthetic process Effects 0.000 description 4
- 229960004436 budesonide Drugs 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 4
- 229960002714 fluticasone Drugs 0.000 description 4
- MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 description 4
- 230000026030 halogenation Effects 0.000 description 4
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- 150000004702 methyl esters Chemical class 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
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- 150000003431 steroids Chemical class 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LUKZNWIVRBCLON-GXOBDPJESA-N Ciclesonide Chemical compound C1([C@H]2O[C@@]3([C@H](O2)C[C@@H]2[C@@]3(C[C@H](O)[C@@H]3[C@@]4(C)C=CC(=O)C=C4CC[C@H]32)C)C(=O)COC(=O)C(C)C)CCCCC1 LUKZNWIVRBCLON-GXOBDPJESA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 3
- JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical compound C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- 229960005070 ascorbic acid Drugs 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 229960003728 ciclesonide Drugs 0.000 description 3
- 230000000536 complexating effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
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Classifications
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- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
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- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/10—Oxygen atoms acylated by aliphatic or araliphatic carboxylic acids, e.g. atropine, scopolamine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/12—Oxygen atoms acylated by aromatic or heteroaromatic carboxylic acids, e.g. cocaine
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Neurology (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10203741A DE10203741A1 (de) | 2002-01-31 | 2002-01-31 | Neue Fluorencarbonsäureester, Verfahren zu deren Herstellung sowie deren Verwendung als Arzneimittel |
| DE10203741 | 2002-01-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2245443T3 true ES2245443T3 (es) | 2006-01-01 |
Family
ID=27588159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES03734600T Expired - Lifetime ES2245443T3 (es) | 2002-01-31 | 2003-01-21 | Nuevos esteres de acidos fluoreno-carboxilicos, procedimiento para su preparacion, asi como su utilizacion como medicamentos. |
Country Status (28)
| Country | Link |
|---|---|
| EP (2) | EP1561751A1 (enExample) |
| JP (1) | JP4484522B2 (enExample) |
| KR (1) | KR100950869B1 (enExample) |
| CN (1) | CN100348598C (enExample) |
| AR (1) | AR038379A1 (enExample) |
| AT (1) | ATE299880T1 (enExample) |
| AU (1) | AU2003210172C1 (enExample) |
| BR (1) | BR0307294A (enExample) |
| CA (1) | CA2472149C (enExample) |
| DE (2) | DE10203741A1 (enExample) |
| EA (1) | EA006966B1 (enExample) |
| EC (1) | ECSP045209A (enExample) |
| ES (1) | ES2245443T3 (enExample) |
| HR (1) | HRP20040690B1 (enExample) |
| IL (1) | IL162527A0 (enExample) |
| ME (1) | MEP43408A (enExample) |
| MX (1) | MXPA04007245A (enExample) |
| MY (1) | MY134582A (enExample) |
| NO (1) | NO328929B1 (enExample) |
| NZ (1) | NZ534784A (enExample) |
| PE (1) | PE20031029A1 (enExample) |
| PL (1) | PL209037B1 (enExample) |
| PT (1) | PT1472251E (enExample) |
| RS (1) | RS50918B (enExample) |
| TW (1) | TWI352077B (enExample) |
| UA (1) | UA78544C2 (enExample) |
| UY (1) | UY27633A1 (enExample) |
| WO (1) | WO2003064419A1 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007500148A (ja) * | 2003-07-28 | 2007-01-11 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｐｄｅｉｖ阻害薬と新規な抗コリン作用薬とを含有する医薬品ならびに呼吸器疾患治療のための該医薬品の使用 |
| ATE420641T1 (de) * | 2003-07-28 | 2009-01-15 | Boehringer Ingelheim Int | Medikamente zur inhalation mit betamimetika und einem anticholinergikum |
| JP2007500147A (ja) * | 2003-07-28 | 2007-01-11 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ステロイド及びフルオレンカルボン酸エステルを含有する吸入用医薬品 |
| WO2005013994A1 (en) * | 2003-07-31 | 2005-02-17 | Boehringer Ingelheim International Gmbh | Medicaments for inhalation comprising anticholinergics and a betamimetic |
| DE102004001607A1 (de) * | 2004-01-09 | 2005-08-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Arzneimittelkombinationen auf der Basis von Scopin- oder Tropensäureestern mit EGFR-Kinase-Hemmern |
| JP2007523116A (ja) * | 2004-02-20 | 2007-08-16 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 抗コリン作用薬及びｐｅｇｓｕｎｅｒｃｅｐｔを基にした新規な医薬組成物 |
| US7507745B2 (en) * | 2004-02-20 | 2009-03-24 | Boehringer Ingelheim International Gmbh | Pharmaceutical compositions based on fluorenecarboxylic acid esters and soluble TNF receptor fusion proteins |
| DE102004016179A1 (de) * | 2004-03-30 | 2005-10-20 | Boehringer Ingelheim Pharma | Verbindungen zur Behandlung von proliferativen Prozessen |
| US20060034776A1 (en) * | 2004-08-10 | 2006-02-16 | Boehringer Ingelheim International Gmbh | Inhalable medicaments containing a new anticholinergic, corticosteroids, and betamimetics |
| DE102004038885A1 (de) * | 2004-08-10 | 2006-02-23 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Aerosolformulierung für die Inhalation enthaltend ein Anticholinergikum |
| ATE427108T1 (de) * | 2004-08-11 | 2009-04-15 | Boehringer Ingelheim Pharma | Anticholinergika enthaltende arzneimittel zur behandlung von krankheiten der ableitenden harnwege |
| DE102005001297A1 (de) * | 2005-01-12 | 2006-07-20 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Aerosolformulierung für die Inhalation enthaltend ein Anticholinergikum |
| EP1855689A1 (en) * | 2005-02-16 | 2007-11-21 | Boehringer Ingelheim International GmbH | Pharmaceutical compositions comprising anticholinergics and etiprednol |
| EP1858554A2 (en) * | 2005-03-09 | 2007-11-28 | Boehringer Ingelheim International GmbH | New pharmaceutical compositions based on anticholinergics and pde 5-inhibitors |
| EP1893203A2 (en) * | 2005-05-31 | 2008-03-05 | Boehringer Ingelheim International GmbH | Medicament containing a betamimetic in conjunction with an anticholinergic and a pde iv inhibitor |
| DE102005030733A1 (de) | 2005-07-01 | 2007-01-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Arzneimittelkombinationen zur Behandlung von Atemwegserkrankungen enthaltend langwirksame Beta-2-Agonisten und wenigstens einen weiteren Wirkstoff |
| US7423146B2 (en) | 2005-11-09 | 2008-09-09 | Boehringer Ingelheim International Gmbh | Process for the manufacturing of pharmaceutically active 3,1-benzoxazine-2-ones |
| CA2660186A1 (en) | 2006-08-07 | 2008-02-14 | Boehringer Ingelheim International Gmbh | Pharmaceutical combinations for the treatment of respiratory diseases |
| PE20080610A1 (es) | 2006-08-22 | 2008-07-15 | Boehringer Ingelheim Int | Nuevos beta-agonistas enantiomericamente puros, procedimientos para su preparacion y uso como medicamentos |
| EP1925296A1 (de) * | 2006-11-22 | 2008-05-28 | Boehringer Ingelheim Pharma GmbH & Co. KG | Stabile Pulverformulierung enthaltend ein neues Anticholinergikum |
| EP1997819A1 (de) * | 2007-05-25 | 2008-12-03 | Boehringer Ingelheim Pharma GmbH & Co. KG | Verfahren zur Herstellung von Scopinestern |
| ES2569359T3 (es) | 2007-07-06 | 2016-05-10 | Vectura Delivery Devices Limited | Inhalador |
| CA2688669A1 (en) * | 2007-07-18 | 2009-01-22 | Boehringer Ingelheim International Gmbh | New combinations for the treatment of respiratory diseases |
| EP2082771A1 (en) | 2008-01-24 | 2009-07-29 | Vectura Delivery Devices Limited | Inhaler |
| EP2082766A1 (en) | 2008-01-24 | 2009-07-29 | Vectura Delivery Devices Limited | Blister Strip Coil Forming |
| EP2082767A1 (en) | 2008-01-24 | 2009-07-29 | Vectura Delivery Devices Limited | Inhaler |
| EP2082772A1 (en) | 2008-01-24 | 2009-07-29 | Vectura Delivery Devices Limited | Inhaler |
| EP2082768A1 (en) | 2008-01-24 | 2009-07-29 | Vectura Delivery Devices Limited | Inhaler |
| EP2093219A1 (de) | 2008-02-22 | 2009-08-26 | Boehringer Ingelheim International Gmbh | Kristalline, enantiomerenreine Salzform eines Betamimetikums und dessen Verwendung als Arzneimittel |
| GB0918450D0 (en) | 2009-10-21 | 2009-12-09 | Innovata Ltd | Composition |
| CN102876318B (zh) * | 2012-09-28 | 2014-07-16 | 宁波大学 | 一种芴羧酸酯荧光材料及其制备方法 |
| US10342786B2 (en) | 2017-10-05 | 2019-07-09 | Fulcrum Therapeutics, Inc. | P38 kinase inhibitors reduce DUX4 and downstream gene expression for the treatment of FSHD |
| CA3078232A1 (en) | 2017-10-05 | 2019-04-11 | Fulcrum Therapeutics, Inc. | Use of p38 inhibitors to reduce expression of dux4 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2221828A (en) * | 1936-04-25 | 1940-11-19 | Merck & Co Inc | Esters of amino alcohols with 9-hydroxyfluorene-9-carboxylic acid and processes for their production |
| DE4108393A1 (de) * | 1991-03-15 | 1992-09-17 | Boehringer Ingelheim Kg | Neue ester bi- und tricyclischer aminoalkohole, ihre herstellung und ihre verwendung in arzneimitteln |
-
2002
- 2002-01-31 DE DE10203741A patent/DE10203741A1/de not_active Withdrawn
-
2003
- 2003-01-21 JP JP2003564042A patent/JP4484522B2/ja not_active Expired - Lifetime
- 2003-01-21 CN CNB038030004A patent/CN100348598C/zh not_active Expired - Fee Related
- 2003-01-21 BR BR0307294-0A patent/BR0307294A/pt not_active Application Discontinuation
- 2003-01-21 RS YUP-656/04A patent/RS50918B/sr unknown
- 2003-01-21 HR HRP20040690AA patent/HRP20040690B1/xx not_active IP Right Cessation
- 2003-01-21 ME MEP-434/08A patent/MEP43408A/xx unknown
- 2003-01-21 EP EP05004525A patent/EP1561751A1/de not_active Withdrawn
- 2003-01-21 PT PT03734600T patent/PT1472251E/pt unknown
- 2003-01-21 MX MXPA04007245A patent/MXPA04007245A/es active IP Right Grant
- 2003-01-21 CA CA2472149A patent/CA2472149C/en not_active Expired - Fee Related
- 2003-01-21 IL IL16252703A patent/IL162527A0/xx not_active IP Right Cessation
- 2003-01-21 AT AT03734600T patent/ATE299880T1/de active
- 2003-01-21 ES ES03734600T patent/ES2245443T3/es not_active Expired - Lifetime
- 2003-01-21 DE DE50300813T patent/DE50300813D1/de not_active Expired - Lifetime
- 2003-01-21 EA EA200400878A patent/EA006966B1/ru not_active IP Right Cessation
- 2003-01-21 UA UA20040807067A patent/UA78544C2/uk unknown
- 2003-01-21 NZ NZ534784A patent/NZ534784A/en not_active IP Right Cessation
- 2003-01-21 KR KR1020047011881A patent/KR100950869B1/ko not_active Expired - Fee Related
- 2003-01-21 EP EP03734600A patent/EP1472251B1/de not_active Expired - Lifetime
- 2003-01-21 AU AU2003210172A patent/AU2003210172C1/en not_active Ceased
- 2003-01-21 WO PCT/EP2003/000534 patent/WO2003064419A1/de not_active Ceased
- 2003-01-21 PL PL369396A patent/PL209037B1/pl unknown
- 2003-01-29 TW TW092101968A patent/TWI352077B/zh active
- 2003-01-29 MY MYPI20030303A patent/MY134582A/en unknown
- 2003-01-29 PE PE2003000092A patent/PE20031029A1/es not_active Application Discontinuation
- 2003-01-30 UY UY27633A patent/UY27633A1/es not_active Application Discontinuation
- 2003-01-31 AR ARP030100288A patent/AR038379A1/es not_active Application Discontinuation
-
2004
- 2004-07-28 EC EC2004005209A patent/ECSP045209A/es unknown
- 2004-08-30 NO NO20043612A patent/NO328929B1/no not_active IP Right Cessation
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