FI72510C - Foerfarande foer framstaellning av terapeutiskt anvaendbara eterfoereningar. - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara eterfoereningar. Download PDFInfo
- Publication number
- FI72510C FI72510C FI814058A FI814058A FI72510C FI 72510 C FI72510 C FI 72510C FI 814058 A FI814058 A FI 814058A FI 814058 A FI814058 A FI 814058A FI 72510 C FI72510 C FI 72510C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- formyl
- acid
- water
- compounds
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 32
- 238000002360 preparation method Methods 0.000 title claims description 27
- 150000002170 ethers Chemical class 0.000 title claims description 6
- 230000008569 process Effects 0.000 title claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 107
- 150000001875 compounds Chemical class 0.000 claims description 94
- 229910052727 yttrium Inorganic materials 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 29
- -1 5-tetrazolyl Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- XEDONBRPTABQFB-UHFFFAOYSA-N 4-[(2-formyl-3-hydroxyphenoxy)methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1COC1=CC=CC(O)=C1C=O XEDONBRPTABQFB-UHFFFAOYSA-N 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 116
- 239000000243 solution Substances 0.000 description 97
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 94
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
- 239000000203 mixture Substances 0.000 description 66
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 56
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 34
- 235000002639 sodium chloride Nutrition 0.000 description 31
- 239000007787 solid Substances 0.000 description 27
- 238000003756 stirring Methods 0.000 description 25
- 239000000284 extract Substances 0.000 description 24
- 239000002253 acid Substances 0.000 description 23
- 210000004369 blood Anatomy 0.000 description 23
- 239000008280 blood Substances 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 22
- 239000003921 oil Substances 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 20
- 239000001301 oxygen Substances 0.000 description 20
- 229910052760 oxygen Inorganic materials 0.000 description 20
- 210000004027 cell Anatomy 0.000 description 19
- 238000001914 filtration Methods 0.000 description 19
- 238000010992 reflux Methods 0.000 description 19
- 229910052938 sodium sulfate Inorganic materials 0.000 description 19
- 235000011152 sodium sulphate Nutrition 0.000 description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
- 238000009472 formulation Methods 0.000 description 17
- 229910000027 potassium carbonate Inorganic materials 0.000 description 17
- 201000010099 disease Diseases 0.000 description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 16
- 239000003208 petroleum Substances 0.000 description 15
- 235000009518 sodium iodide Nutrition 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 208000007056 sickle cell anemia Diseases 0.000 description 14
- 108010054147 Hemoglobins Proteins 0.000 description 13
- 102000001554 Hemoglobins Human genes 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 210000003743 erythrocyte Anatomy 0.000 description 12
- CFBCZETZIPZOGW-UHFFFAOYSA-N 1-benzofuran-4-ol Chemical compound OC1=CC=CC2=C1C=CO2 CFBCZETZIPZOGW-UHFFFAOYSA-N 0.000 description 10
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 10
- 238000011282 treatment Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 238000000338 in vitro Methods 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 8
- AELJSHCCSWZMLX-UHFFFAOYSA-N ethyl 4-[(2-formyl-3-hydroxyphenoxy)methyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1COC1=CC=CC(O)=C1C=O AELJSHCCSWZMLX-UHFFFAOYSA-N 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- 238000010494 dissociation reaction Methods 0.000 description 6
- 230000005593 dissociations Effects 0.000 description 6
- AFRWBGJRWRHQOV-UHFFFAOYSA-N ethyl 5-bromopentanoate Chemical compound CCOC(=O)CCCCBr AFRWBGJRWRHQOV-UHFFFAOYSA-N 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- TWSIYGATPWEKBK-UHFFFAOYSA-N 4h-1,3-benzodioxine Chemical class C1=CC=C2OCOCC2=C1 TWSIYGATPWEKBK-UHFFFAOYSA-N 0.000 description 5
- KEBYHXYCEYOGHT-UHFFFAOYSA-N 5-(1-benzofuran-4-yloxy)pentanoic acid Chemical compound OC(=O)CCCCOC1=CC=CC2=C1C=CO2 KEBYHXYCEYOGHT-UHFFFAOYSA-N 0.000 description 5
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 5
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 5
- TWQLMAJROCNXEA-UHFFFAOYSA-N ethyl 4-(bromomethyl)benzoate Chemical compound CCOC(=O)C1=CC=C(CBr)C=C1 TWQLMAJROCNXEA-UHFFFAOYSA-N 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 5
- 229910001641 magnesium iodide Inorganic materials 0.000 description 5
- 239000012258 stirred mixture Substances 0.000 description 5
- 150000003536 tetrazoles Chemical class 0.000 description 5
- 239000008215 water for injection Substances 0.000 description 5
- DXMHWTUWSSJRID-UHFFFAOYSA-N 2-methyl-1-benzofuran-4-ol Chemical compound C1=CC=C2OC(C)=CC2=C1O DXMHWTUWSSJRID-UHFFFAOYSA-N 0.000 description 4
- SMFFZOQLHYIRDA-UHFFFAOYSA-N 3,4-dimethoxyphenol Chemical compound COC1=CC=C(O)C=C1OC SMFFZOQLHYIRDA-UHFFFAOYSA-N 0.000 description 4
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 4
- KBWBGANILAOXHI-UHFFFAOYSA-N 5-(2-formyl-3-hydroxyphenoxy)-n-methylsulfonylpentanamide Chemical compound CS(=O)(=O)NC(=O)CCCCOC1=CC=CC(O)=C1C=O KBWBGANILAOXHI-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 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 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 125000001589 carboacyl group Chemical group 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- ASCHANFJRGHKOD-UHFFFAOYSA-N (3-methoxy-4-propoxyphenyl) acetate Chemical compound CCCOC1=CC=C(OC(C)=O)C=C1OC ASCHANFJRGHKOD-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- GSHNZOVUGRZEON-UHFFFAOYSA-N 2-hydroxy-6-(methoxymethoxy)benzaldehyde Chemical compound COCOC1=CC=CC(O)=C1C=O GSHNZOVUGRZEON-UHFFFAOYSA-N 0.000 description 3
- NFFPYJCACRYJQM-UHFFFAOYSA-N 3-(1-benzofuran-4-yloxy)propanenitrile Chemical compound N#CCCOC1=CC=CC2=C1C=CO2 NFFPYJCACRYJQM-UHFFFAOYSA-N 0.000 description 3
- CFHXDPFOAWIMCO-UHFFFAOYSA-N 3-chloro-6-hydroxy-2-methoxybenzaldehyde Chemical compound COC1=C(Cl)C=CC(O)=C1C=O CFHXDPFOAWIMCO-UHFFFAOYSA-N 0.000 description 3
- HEJVIJFVGFESLC-UHFFFAOYSA-N 3-methoxy-4-propoxyphenol Chemical compound CCCOC1=CC=C(O)C=C1OC HEJVIJFVGFESLC-UHFFFAOYSA-N 0.000 description 3
- KGSCRMNLDIWMPE-UHFFFAOYSA-N 4-(methoxymethoxy)-2-methyl-1-benzofuran Chemical compound COCOC1=CC=CC2=C1C=C(C)O2 KGSCRMNLDIWMPE-UHFFFAOYSA-N 0.000 description 3
- NSUDGNLOXMLAEB-UHFFFAOYSA-N 5-(2-formyl-3-hydroxyphenoxy)pentanoic acid Chemical compound OC(=O)CCCCOC1=CC=CC(O)=C1C=O NSUDGNLOXMLAEB-UHFFFAOYSA-N 0.000 description 3
- NIJYKUFMYZYNCN-UHFFFAOYSA-N 5-(2-formyl-3-phenylmethoxyphenoxy)pentanoic acid Chemical compound OC(=O)CCCCOC1=CC=CC(OCC=2C=CC=CC=2)=C1C=O NIJYKUFMYZYNCN-UHFFFAOYSA-N 0.000 description 3
- IUFNEZRKCZYFSG-UHFFFAOYSA-N 5-(4,6-dichloro-2-formyl-3-hydroxyphenoxy)pentanoic acid Chemical compound OC(=O)CCCCOC1=C(Cl)C=C(Cl)C(O)=C1C=O IUFNEZRKCZYFSG-UHFFFAOYSA-N 0.000 description 3
- AEYWTWGAFMYRFW-UHFFFAOYSA-N 5-(4-chloro-2-formyl-3-hydroxyphenoxy)pentanoic acid Chemical compound OC(=O)CCCCOC1=CC=C(Cl)C(O)=C1C=O AEYWTWGAFMYRFW-UHFFFAOYSA-N 0.000 description 3
- HCPKQUXCORABIN-UHFFFAOYSA-N 6-(1-benzofuran-4-yloxy)hexanoic acid Chemical compound OC(=O)CCCCCOC1=CC=CC2=C1C=CO2 HCPKQUXCORABIN-UHFFFAOYSA-N 0.000 description 3
- PKBVOHGNWBQYMY-UHFFFAOYSA-N 6-hydroxy-2-methoxy-3-propoxybenzaldehyde Chemical compound CCCOC1=CC=C(O)C(C=O)=C1OC PKBVOHGNWBQYMY-UHFFFAOYSA-N 0.000 description 3
- DGVPMYXLJJNSOU-UHFFFAOYSA-N 7-(2-formyl-3-hydroxyphenoxy)heptanoic acid Chemical compound OC(=O)CCCCCCOC1=CC=CC(O)=C1C=O DGVPMYXLJJNSOU-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 238000005915 ammonolysis reaction Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 3
- JYSOZGGVTRYSSA-UHFFFAOYSA-N ethyl 4-(1-benzofuran-4-yloxymethyl)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1COC1=CC=CC2=C1C=CO2 JYSOZGGVTRYSSA-UHFFFAOYSA-N 0.000 description 3
- QEGWIXJLDSHEIN-UHFFFAOYSA-N ethyl 4-[(3-acetamido-2-formylphenoxy)methyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1COC1=CC=CC(NC(C)=O)=C1C=O QEGWIXJLDSHEIN-UHFFFAOYSA-N 0.000 description 3
- STSKNIDIEUEWGT-UHFFFAOYSA-N ethyl 5-(2-formyl-3-methoxy-4-propoxyphenoxy)pentanoate Chemical compound CCCOC1=CC=C(OCCCCC(=O)OCC)C(C=O)=C1OC STSKNIDIEUEWGT-UHFFFAOYSA-N 0.000 description 3
- WKNGDZQZYOAAJI-UHFFFAOYSA-N ethyl 5-(2-formyl-3-phenylmethoxyphenoxy)pentanoate Chemical compound CCOC(=O)CCCCOC1=CC=CC(OCC=2C=CC=CC=2)=C1C=O WKNGDZQZYOAAJI-UHFFFAOYSA-N 0.000 description 3
- VDKNZCCLKACNAS-UHFFFAOYSA-N ethyl 7-(2-formyl-3-methoxyphenoxy)heptanoate Chemical compound CCOC(=O)CCCCCCOC1=CC=CC(OC)=C1C=O VDKNZCCLKACNAS-UHFFFAOYSA-N 0.000 description 3
- 238000001879 gelation Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
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- HIVDMVZJKJRWCZ-UHFFFAOYSA-M sodium;3-hydroxy-2-methylthiobenzate Chemical compound [Na+].CC1=C(O)C=CC=C1C([O-])=S HIVDMVZJKJRWCZ-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
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- 238000007920 subcutaneous administration Methods 0.000 description 1
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- 238000011269 treatment regimen Methods 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- YNIRKEZIDLCCMC-UHFFFAOYSA-K trisodium;phosphate;hydrate Chemical compound [OH-].[Na+].[Na+].[Na+].OP([O-])([O-])=O YNIRKEZIDLCCMC-UHFFFAOYSA-K 0.000 description 1
- 208000021331 vascular occlusion disease Diseases 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/74—Unsaturated compounds containing —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/30—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8040512 | 1980-12-18 | ||
| GB8040512 | 1980-12-18 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI814058L FI814058L (fi) | 1982-06-19 |
| FI72510B FI72510B (fi) | 1987-02-27 |
| FI72510C true FI72510C (fi) | 1987-06-08 |
Family
ID=10518062
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI814058A FI72510C (fi) | 1980-12-18 | 1981-12-17 | Foerfarande foer framstaellning av terapeutiskt anvaendbara eterfoereningar. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4535183A (en, 2012) |
| EP (1) | EP0054924B1 (en, 2012) |
| JP (1) | JPS57145844A (en, 2012) |
| DE (1) | DE3175083D1 (en, 2012) |
| DK (1) | DK160866C (en, 2012) |
| FI (1) | FI72510C (en, 2012) |
| GB (1) | GB2090830B (en, 2012) |
| GR (1) | GR76950B (en, 2012) |
| HU (1) | HU190371B (en, 2012) |
| IL (1) | IL64573A (en, 2012) |
| IT (1) | IT1193786B (en, 2012) |
| OA (1) | OA06998A (en, 2012) |
| ZA (1) | ZA818741B (en, 2012) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8318889D0 (en) * | 1983-07-13 | 1983-08-17 | Lilly Industries Ltd | Pharmaceutical compounds |
| US4887995A (en) * | 1985-01-22 | 1989-12-19 | University Of Pittsburgh | Method of treating sickle cell anemia |
| US4731381A (en) * | 1986-04-04 | 1988-03-15 | Merck & Co., Inc. | Method of treating a person for sickle cell anemia |
| IL98405A0 (en) * | 1990-06-11 | 1992-07-15 | Fmc Corp | Pharmaceutical compositions containing enzyme inhibiting agents |
| TW209866B (en, 2012) * | 1991-03-20 | 1993-07-21 | Hoechst Ag | |
| SG48993A1 (en) * | 1992-10-01 | 1998-05-18 | Wellcome Found | Immunopotentiatory agent and physiologically acceptable salts thereof |
| US5872151A (en) * | 1992-10-01 | 1999-02-16 | Glaxo Wellcome Inc. | Immunopotentiatory agents and physiologically acceptable salts thereof |
| US5958980A (en) * | 1993-08-26 | 1999-09-28 | Glaxo Wellcome, Inc. | Immunopotentiatory agent and physiologically acceptable salts thereof |
| US6068834A (en) * | 1994-03-04 | 2000-05-30 | The Procter & Gamble Company | Skin lightening compositions |
| NZ313896A (en) * | 1995-08-28 | 2000-08-25 | American Home Prod | 4-formyl-2-(naphthalenylmethyl)phenoxyacetic acids or salts and antihyperglycemic agents for the treatment of diabetes mellitus |
| JP4316688B2 (ja) * | 1996-07-15 | 2009-08-19 | 日産化学工業株式会社 | 置換ビナフチル化合物及びその製造法 |
| AU7550398A (en) * | 1997-06-05 | 1998-12-21 | Takeda Chemical Industries Ltd. | Heterocyclic compounds, their production and use |
| EP1265840A2 (en) * | 2000-03-17 | 2002-12-18 | Corixa Corporation | Novel amphipathic aldehydes and their use as adjuvants and immunoeffectors |
| JP4688315B2 (ja) * | 2001-02-28 | 2011-05-25 | メルシャン株式会社 | ４−デメトキシダウノマイシノンの製造 |
| US8198328B2 (en) | 2004-01-21 | 2012-06-12 | New York University | Treatment of cancer using benzoic acid derivatives |
| SI3141542T1 (sl) | 2011-12-28 | 2020-11-30 | Global Blood Therapeutics, Inc. | Substituirane spojine benzaldehida in metode njihove uporabe pri povečanju oksigenacije tkiva |
| WO2013102145A1 (en) | 2011-12-28 | 2013-07-04 | Global Blood Therapeutics, Inc. | Substituted heteroaryl aldehyde compounds and methods for their use in increasing tissue oxygenation |
| US9422279B2 (en) | 2013-03-15 | 2016-08-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US10266551B2 (en) * | 2013-03-15 | 2019-04-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| ES2852054T3 (es) * | 2013-03-15 | 2021-09-10 | Global Blood Therapeutics Inc | Compuestos y usos de los mismos para la modulación de hemoglobina |
| US9802900B2 (en) | 2013-03-15 | 2017-10-31 | Global Blood Therapeutics, Inc. | Bicyclic heteroaryl compounds and uses thereof for the modulation of hemoglobin |
| ES2909634T3 (es) * | 2013-03-15 | 2022-05-09 | Global Blood Therapeutics Inc | Compuestos y usos de los mismos para la modulación de hemoglobina |
| US8952171B2 (en) * | 2013-03-15 | 2015-02-10 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9458139B2 (en) | 2013-03-15 | 2016-10-04 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9604999B2 (en) * | 2013-03-15 | 2017-03-28 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| WO2014145040A1 (en) | 2013-03-15 | 2014-09-18 | Global Blood Therapeutics, Inc. | Substituted aldehyde compounds and methods for their use in increasing tissue oxygenation |
| AP2015008718A0 (en) | 2013-03-15 | 2015-09-30 | Global Blood Therapeutics Inc | Compounds and uses thereof for the modulation of hemoglobin |
| EP2970308B1 (en) * | 2013-03-15 | 2021-07-14 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| EP2970184B1 (en) * | 2013-03-15 | 2018-12-05 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| EA202092627A1 (ru) | 2013-11-18 | 2021-09-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
| CN105431147A (zh) | 2014-02-07 | 2016-03-23 | 全球血液疗法股份有限公司 | 2-羟基-6-((2-(1-异丙基-1h-吡唑-5-基)吡啶-3-基)甲氧基)苯甲醛的游离碱的结晶多晶型物 |
| WO2016043849A2 (en) * | 2014-07-24 | 2016-03-24 | Global Blood Therapeutics, Inc. | Compounds for treating acute respiratory distress syndrome or a negative effect thereof |
| MX383691B (es) | 2015-03-06 | 2025-03-14 | Beyondspring Pharmaceuticals Inc | Método de tratamiento de cáncer asociado con una mutación de ras. |
| MA41841A (fr) | 2015-03-30 | 2018-02-06 | Global Blood Therapeutics Inc | Composés aldéhyde pour le traitement de la fibrose pulmonaire, de l'hypoxie, et de maladies auto-immunes et des tissus conjonctifs |
| SG10202108194XA (en) | 2015-07-13 | 2021-09-29 | Beyondspring Pharmaceuticals Inc | Plinabulin compositions |
| WO2017096230A1 (en) | 2015-12-04 | 2017-06-08 | Global Blood Therapeutics, Inc. | Dosing regimens for 2-hydroxy-6-((2-(1-isopropyl-1h-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde |
| BR112018016054A2 (pt) * | 2016-02-08 | 2019-02-12 | Beyondspring Pharmaceuticals, Inc. | composições farmacêuticas e/ou métodos para tratar câncer e/ou para romper vasculatura de tumor associada ao câncer em indivíduo |
| TWI752307B (zh) | 2016-05-12 | 2022-01-11 | 美商全球血液治療公司 | 新穎化合物及製造化合物之方法 |
| SG11201810872UA (en) | 2016-06-06 | 2019-01-30 | Beyondspring Pharmaceuticals Inc | Composition and method for reducing neutropenia |
| TWI778983B (zh) | 2016-10-12 | 2022-10-01 | 美商全球血液治療公司 | 包含2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)吡啶-3-基)甲氧基)-苯甲醛之片劑 |
| EP3565812B1 (en) | 2017-01-06 | 2023-12-27 | Beyondspring Pharmaceuticals, Inc. | Tubulin binding compounds and therapeutic use thereof |
| CA3052190A1 (en) | 2017-02-01 | 2018-08-09 | Beyondspring Pharmaceuticals, Inc. | Method of reducing neutropenia |
| KR20200112881A (ko) | 2018-01-24 | 2020-10-05 | 비욘드스프링 파마수티컬스, 인코포레이티드. | 플리나불린의 투여를 통해 혈소판감소증을 감소시키는 조성물 및 방법 |
| ES2966707T3 (es) | 2018-10-01 | 2024-04-23 | Global Blood Therapeutics Inc | Moduladores de la hemoglobina para el tratamiento de la drepanocitosis |
| SI3880654T1 (sl) | 2018-11-19 | 2022-04-29 | Global Blood Therapeutics, Inc. | 2-formil-3-hidroksifeniloksimetilne spojine, zmožne modulirati hemoglobin |
| CN112778155B (zh) * | 2019-11-11 | 2023-08-11 | 大连万春布林医药有限公司 | 妥卡雷琐衍生物及其用途 |
| JP2024513505A (ja) | 2021-04-09 | 2024-03-25 | ビヨンドスプリング ファーマシューティカルズ，インコーポレイテッド | 腫瘍を治療するための組成物及び方法 |
| CN115636742B (zh) * | 2022-11-11 | 2024-04-09 | 江西亚太科技发展有限公司 | 一种重结晶的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR71054E (fr) * | 1957-02-19 | 1959-10-08 | Rhone Poulenc Sa | Nouveaux dérivés phénoxycarboxyliques |
| FR1186520A (fr) * | 1957-11-18 | 1959-08-26 | Rhone Poulenc Sa | Nouvelles compositions phytohormonales |
| CH543472A (fr) * | 1969-01-31 | 1973-10-31 | Orchimed Sa | Procédé pour la préparation d'acides phénoxyalcoyl-carboxyliques |
| JPS5851972B2 (ja) * | 1976-05-14 | 1983-11-19 | 昭和化学工業株式会社 | １，４−ビス−スチリルベンゼン誘導体およびその製法 |
| DE3061269D1 (en) * | 1979-06-29 | 1983-01-13 | Wellcome Found | Substituted phenol ethers, their preparation, intermediates therefor, pharmaceutical compositions containing them and the preparation thereof |
-
1981
- 1981-12-17 IL IL64573A patent/IL64573A/xx not_active IP Right Cessation
- 1981-12-17 GR GR66822A patent/GR76950B/el unknown
- 1981-12-17 ZA ZA818741A patent/ZA818741B/xx unknown
- 1981-12-17 GB GB8138086A patent/GB2090830B/en not_active Expired
- 1981-12-17 IT IT49937/81A patent/IT1193786B/it active
- 1981-12-17 FI FI814058A patent/FI72510C/fi not_active IP Right Cessation
- 1981-12-17 DE DE8181110553T patent/DE3175083D1/de not_active Expired
- 1981-12-17 JP JP56204493A patent/JPS57145844A/ja active Granted
- 1981-12-17 DK DK561881A patent/DK160866C/da not_active IP Right Cessation
- 1981-12-17 HU HU813807A patent/HU190371B/hu unknown
- 1981-12-17 EP EP81110553A patent/EP0054924B1/en not_active Expired
- 1981-12-18 US US06/332,246 patent/US4535183A/en not_active Expired - Lifetime
-
1982
- 1982-01-16 OA OA57595A patent/OA06998A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4535183A (en) | 1985-08-13 |
| DE3175083D1 (en) | 1986-09-11 |
| IL64573A (en) | 1985-04-30 |
| EP0054924A3 (en) | 1982-09-22 |
| IT1193786B (it) | 1988-08-24 |
| IL64573A0 (en) | 1982-03-31 |
| JPS57145844A (en) | 1982-09-09 |
| IT8149937A0 (it) | 1981-12-17 |
| FI814058L (fi) | 1982-06-19 |
| DK160866B (da) | 1991-04-29 |
| DK561881A (da) | 1982-06-19 |
| EP0054924B1 (en) | 1986-08-06 |
| GR76950B (en, 2012) | 1984-09-04 |
| FI72510B (fi) | 1987-02-27 |
| OA06998A (fr) | 1983-08-31 |
| GB2090830A (en) | 1982-07-21 |
| GB2090830B (en) | 1984-09-26 |
| JPH0249294B2 (en, 2012) | 1990-10-29 |
| HU190371B (en) | 1986-08-28 |
| EP0054924A2 (en) | 1982-06-30 |
| DK160866C (da) | 1991-10-14 |
| ZA818741B (en) | 1983-07-27 |
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Legal Events
| Date | Code | Title | Description |
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| MA | Patent expired |
Owner name: THE WELLCOME FOUNDATION LIMITED |