JPH0154339B2 - - Google Patents
Info
- Publication number
- JPH0154339B2 JPH0154339B2 JP55087645A JP8764580A JPH0154339B2 JP H0154339 B2 JPH0154339 B2 JP H0154339B2 JP 55087645 A JP55087645 A JP 55087645A JP 8764580 A JP8764580 A JP 8764580A JP H0154339 B2 JPH0154339 B2 JP H0154339B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- formyl
- hydrogen
- salt
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 143
- 239000000243 solution Substances 0.000 claims description 81
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 76
- -1 ether compound Chemical class 0.000 claims description 62
- 150000003839 salts Chemical class 0.000 claims description 60
- 239000000203 mixture Substances 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 210000004369 blood Anatomy 0.000 claims description 31
- 239000008280 blood Substances 0.000 claims description 31
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
- 238000004519 manufacturing process Methods 0.000 claims description 30
- 239000001301 oxygen Substances 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 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 claims description 24
- 239000008194 pharmaceutical composition Substances 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 23
- 238000010494 dissociation reaction Methods 0.000 claims description 18
- 230000005593 dissociations Effects 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 231100000252 nontoxic Toxicity 0.000 claims description 9
- 230000003000 nontoxic effect Effects 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 claims description 8
- 229910001641 magnesium iodide Inorganic materials 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- PVPWPJFEUIVMSW-UHFFFAOYSA-N ethyl 5-(2-formyl-3-hydroxyphenoxy)pentanoate Chemical compound CCOC(=O)CCCCOC1=CC=CC(O)=C1C=O PVPWPJFEUIVMSW-UHFFFAOYSA-N 0.000 claims description 6
- XPKJLBBVFHFSEM-UHFFFAOYSA-N 5-(2-formyl-3-hydroxyphenoxy)-2,2-dimethylpentanoic acid Chemical compound OC(=O)C(C)(C)CCCOC1=CC=CC(O)=C1C=O XPKJLBBVFHFSEM-UHFFFAOYSA-N 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- QYLSCHCZGSONML-UHFFFAOYSA-N 5-(2-formyl-3-hydroxyphenoxy)-2-methylpentanoic acid Chemical compound OC(=O)C(C)CCCOC1=CC=CC(O)=C1C=O QYLSCHCZGSONML-UHFFFAOYSA-N 0.000 claims description 4
- FYUSDHGUBKZBON-UHFFFAOYSA-N 5-(2-formyl-3-hydroxyphenoxy)pentanenitrile Chemical compound OC1=CC=CC(OCCCCC#N)=C1C=O FYUSDHGUBKZBON-UHFFFAOYSA-N 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 4
- 238000002347 injection Methods 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- SLOWFFLRNJZBAZ-UHFFFAOYSA-N 3-[(2-formyl-3-hydroxyphenoxy)methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(COC=2C(=C(O)C=CC=2)C=O)=C1 SLOWFFLRNJZBAZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 238000007911 parenteral administration Methods 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- MCZIMYJCVWHKOK-UHFFFAOYSA-N ethyl 5-(2-formyl-3-methoxyphenoxy)pentanoate Chemical compound CCOC(=O)CCCCOC1=CC=CC(OC)=C1C=O MCZIMYJCVWHKOK-UHFFFAOYSA-N 0.000 claims description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 51
- 235000002639 sodium chloride Nutrition 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
- 239000007787 solid Substances 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 24
- 210000004027 cell Anatomy 0.000 description 22
- 238000002844 melting Methods 0.000 description 22
- 230000008018 melting Effects 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 22
- 238000003756 stirring Methods 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 238000001816 cooling Methods 0.000 description 17
- 239000003208 petroleum Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000010410 layer Substances 0.000 description 15
- 241000700159 Rattus Species 0.000 description 14
- 230000000694 effects Effects 0.000 description 14
- 238000000338 in vitro Methods 0.000 description 14
- 239000007788 liquid Substances 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 12
- 235000017557 sodium bicarbonate Nutrition 0.000 description 12
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 150000001408 amides Chemical class 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 150000002148 esters Chemical class 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
- 239000003921 oil Substances 0.000 description 8
- 235000009518 sodium iodide Nutrition 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 230000037396 body weight Effects 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 6
- KKGWWGPCKRNRNW-UHFFFAOYSA-N C(=O)C1=C(OCCCCC(=O)O)C=CC=C1OC.C(=O)C1=C(OCCCCC(=O)O)C=CC=C1O Chemical compound C(=O)C1=C(OCCCCC(=O)O)C=CC=C1OC.C(=O)C1=C(OCCCCC(=O)O)C=CC=C1O KKGWWGPCKRNRNW-UHFFFAOYSA-N 0.000 description 5
- 102000001554 Hemoglobins Human genes 0.000 description 5
- 108010054147 Hemoglobins Proteins 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
- 239000012074 organic phase Substances 0.000 description 5
- 208000007056 sickle cell anemia Diseases 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000008215 water for injection Substances 0.000 description 5
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 4
- 206010021143 Hypoxia Diseases 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- AFRWBGJRWRHQOV-UHFFFAOYSA-N ethyl 5-bromopentanoate Chemical compound CCOC(=O)CCCCBr AFRWBGJRWRHQOV-UHFFFAOYSA-N 0.000 description 4
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000010561 standard procedure Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 239000003146 anticoagulant agent Substances 0.000 description 3
- 229940127219 anticoagulant drug Drugs 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000007954 hypoxia Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 230000005980 lung dysfunction Effects 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229940068041 phytic acid Drugs 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- OVBFMEVBMNZIBR-UHFFFAOYSA-N -2-Methylpentanoic acid Natural products CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 2
- IJRKANNOPXMZSG-SSPAHAAFSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC(=O)CC(O)(C(O)=O)CC(O)=O IJRKANNOPXMZSG-SSPAHAAFSA-N 0.000 description 2
- FRXRLTATMMDVNZ-UHFFFAOYSA-N 5-(2-formyl-3-hydroxyphenoxy)pentanamide Chemical compound NC(=O)CCCCOC1=CC=CC(O)=C1C=O FRXRLTATMMDVNZ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- 206010006458 Bronchitis chronic Diseases 0.000 description 2
- BKROBWQGDCDWJN-UHFFFAOYSA-N C(C(C)C)[AlH]CC(C)C.[Na] Chemical compound C(C(C)C)[AlH]CC(C)C.[Na] BKROBWQGDCDWJN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 206010014561 Emphysema Diseases 0.000 description 2
- ICMAFTSLXCXHRK-UHFFFAOYSA-N Ethyl pentanoate Chemical compound CCCCC(=O)OCC ICMAFTSLXCXHRK-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000005915 ammonolysis reaction Methods 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 210000000601 blood cell Anatomy 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 206010006451 bronchitis Diseases 0.000 description 2
- XAAHAAMILDNBPS-UHFFFAOYSA-L calcium hydrogenphosphate dihydrate Chemical compound O.O.[Ca+2].OP([O-])([O-])=O XAAHAAMILDNBPS-UHFFFAOYSA-L 0.000 description 2
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000007932 molded tablet Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- JPSAMYBDBKJMPH-UHFFFAOYSA-N n,n-diethyl-5-(2-formyl-3-hydroxyphenoxy)pentanamide Chemical compound CCN(CC)C(=O)CCCCOC1=CC=CC(O)=C1C=O JPSAMYBDBKJMPH-UHFFFAOYSA-N 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 125000001749 primary amide group Chemical group 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- JADFCQKRKICRKI-UHFFFAOYSA-N quinoline;sulfane Chemical compound S.N1=CC=CC2=CC=CC=C21 JADFCQKRKICRKI-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000000637 radiosensitizating effect Effects 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 150000003334 secondary amides Chemical class 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- LNSMYUNNQPBRRB-UHFFFAOYSA-M sodium;5-(2-formyl-3-hydroxyphenoxy)pentanoate Chemical compound [Na+].OC1=CC=CC(OCCCCC([O-])=O)=C1C=O LNSMYUNNQPBRRB-UHFFFAOYSA-M 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- LHYPLJGBYPAQAK-UHFFFAOYSA-M sodium;pentanoate Chemical compound [Na+].CCCCC([O-])=O LHYPLJGBYPAQAK-UHFFFAOYSA-M 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000007939 sustained release tablet Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07C59/125—Saturated compounds having only one carboxyl group and containing ether groups, groups, groups, or 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
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pulmonology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7922781 | 1979-06-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5649335A JPS5649335A (en) | 1981-05-02 |
| JPH0154339B2 true JPH0154339B2 (cg-RX-API-DMAC7.html) | 1989-11-17 |
Family
ID=10506199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8764580A Granted JPS5649335A (en) | 1979-06-29 | 1980-06-27 | Ether compound |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4410537A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0022229B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5649335A (cg-RX-API-DMAC7.html) |
| KR (2) | KR850000073B1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU545274B2 (cg-RX-API-DMAC7.html) |
| DE (1) | DE3061269D1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK159770C (cg-RX-API-DMAC7.html) |
| FI (1) | FI71929C (cg-RX-API-DMAC7.html) |
| GB (1) | GB2053218B (cg-RX-API-DMAC7.html) |
| GR (1) | GR68748B (cg-RX-API-DMAC7.html) |
| HU (1) | HU190774B (cg-RX-API-DMAC7.html) |
| IL (1) | IL60422A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1133025B (cg-RX-API-DMAC7.html) |
| MW (1) | MW2380A1 (cg-RX-API-DMAC7.html) |
| OA (1) | OA06699A (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA803880B (cg-RX-API-DMAC7.html) |
| ZM (1) | ZM5780A1 (cg-RX-API-DMAC7.html) |
| ZW (1) | ZW14480A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU190371B (en) * | 1980-12-18 | 1986-08-28 | The Wellcome Foundation Ltd,Gb | Process for producing ether-type compounds and pharmaceutical compositions containing them as active agents |
| GB8606913D0 (en) * | 1986-03-20 | 1986-04-23 | Hider R C | Treatment of sickle cell disease |
| AU6019898A (en) | 1997-01-09 | 1998-08-03 | Cohesion Technologies, Inc. | Devices for tissue repair and methods for preparation and use thereof |
| RU2300516C2 (ru) * | 1999-11-05 | 2007-06-10 | Эмисфере Текнолоджиз, Инк. | Соединения феноксикарбоновой кислоты и композиции для доставки активных веществ |
| US7279597B1 (en) | 1999-11-05 | 2007-10-09 | Emisphere Technologies, Inc. | Phenyl amine carboxylic acid compounds and compositions for delivering active agents |
| JP2004501057A (ja) * | 1999-11-05 | 2004-01-15 | エミスフェアー・テクノロジーズ・インク | フェニルアミンカルボン酸化合物及び活性剤を送達するための組成物 |
| US7129274B1 (en) | 1999-11-05 | 2006-10-31 | Emisphere Technologies Inc. | Phenoxy carboxylic acid compounds and compositions for delivering active agents |
| CA2403553A1 (en) * | 2000-03-17 | 2001-09-27 | David Johnson | Novel amphipathic aldehydes and their use as adjuvants and immunoeffectors |
| US8246969B2 (en) | 2001-11-16 | 2012-08-21 | Skinmedica, Inc. | Compositions containing aromatic aldehydes and their use in treatments |
| KR101916489B1 (ko) | 2011-01-07 | 2018-11-07 | 알러간, 인코포레이티드 | 멜라닌 변형 조성물들 및 이의 사용 방법들 |
| ES2790358T3 (es) * | 2011-12-28 | 2020-10-27 | Global Blood Therapeutics Inc | Compuestos de heteroaril aldehído sustituido y métodos para su uso en el aumento de la oxigenación tisular |
| SI3738434T1 (sl) | 2011-12-28 | 2024-01-31 | Global Blood Therapeutics, Inc. | Vmesne spojine za pridobivanje substituiranih benzaldehidnih spojin in postopki njihove uporabe pri povečanju oksigenacije tkiv |
| US9458139B2 (en) | 2013-03-15 | 2016-10-04 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| SG11201507453VA (en) | 2013-03-15 | 2015-10-29 | Global Blood Therapeutics Inc | Compounds and uses thereof for the modulation of hemoglobin |
| US9422279B2 (en) | 2013-03-15 | 2016-08-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US20140274961A1 (en) | 2013-03-15 | 2014-09-18 | 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 |
| EP2970196B1 (en) * | 2013-03-15 | 2020-11-25 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US10100043B2 (en) | 2013-03-15 | 2018-10-16 | Global Blood Therapeutics, Inc. | Substituted aldehyde compounds and methods for their use in increasing tissue oxygenation |
| US8952171B2 (en) | 2013-03-15 | 2015-02-10 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9802900B2 (en) | 2013-03-15 | 2017-10-31 | Global Blood Therapeutics, Inc. | Bicyclic heteroaryl compounds and uses thereof for the modulation of hemoglobin |
| US9981939B2 (en) | 2013-03-15 | 2018-05-29 | 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 |
| WO2015027067A2 (en) * | 2013-08-23 | 2015-02-26 | Virginia Commonwealth University | Ester nitrates derivatives of aromatic aldehydes with multiple pharmalogic properties to treat sickle cell disease |
| EA201992707A1 (ru) | 2013-11-18 | 2020-06-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
| DK3102208T4 (da) | 2014-02-07 | 2024-08-26 | Global Blood Therapeutics Inc | Krystallinsk polymorph af den frie base af 2-hydroxy-6-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyd |
| CA2978567A1 (en) | 2015-03-06 | 2016-09-15 | Beyondspring Pharmaceuticals, Inc. | Method of treating cancer associated with a ras mutation using plinabulin |
| 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 |
| ES3039236T3 (en) | 2015-12-04 | 2025-10-20 | Global Blood Therapeutics Inc | Dosing regimens for 2-hydroxy-6-((2-(1-isopropyl-1h-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde |
| US10912748B2 (en) * | 2016-02-08 | 2021-02-09 | Beyondspring Pharmaceuticals, Inc. | Compositions containing tucaresol or its analogs |
| TWI663160B (zh) | 2016-05-12 | 2019-06-21 | 全球血液治療公司 | 用於合成2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)-吡啶-3-基)甲氧基)苯甲醛之方法 |
| SG11201810872UA (en) | 2016-06-06 | 2019-01-30 | Beyondspring Pharmaceuticals Inc | Composition and method for reducing neutropenia |
| TW202332423A (zh) | 2016-10-12 | 2023-08-16 | 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 |
| JP2020503363A (ja) | 2017-01-06 | 2020-01-30 | 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 | チューブリン結合化合物およびその治療的使用 |
| CN110381938A (zh) | 2017-02-01 | 2019-10-25 | 大连万春布林医药有限公司 | 减少中性粒细胞缺乏症的方法 |
| US11401241B2 (en) * | 2018-03-22 | 2022-08-02 | Virginia Commonwealth University | Aromatic aldehydes with sustained and enhanced in vitro and in vivo pharmacologic activity to treat sickle cell disease |
| US11014884B2 (en) | 2018-10-01 | 2021-05-25 | Global Blood Therapeutics, Inc. | Modulators of hemoglobin |
| KR102842589B1 (ko) | 2018-11-19 | 2025-08-04 | 글로벌 블러드 테라퓨틱스, 인크. | 헤모글로빈을 조정할 수 있는 2-포르밀-3-히드록시페닐옥시메틸 화합물 |
| WO2020163689A1 (en) | 2019-02-08 | 2020-08-13 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | 20-hete formation inhibitors |
| EP4319751A4 (en) | 2021-04-09 | 2025-02-26 | Beyondspring Pharmaceuticals, Inc. | THERAPEUTIC COMPOSITIONS AND METHODS FOR THE TREATING OF TUMORS |
| IL320636A (en) * | 2022-11-07 | 2025-07-01 | Univ Virginia Commonwealth | Benzaldehyde compounds with destabilizing effects on polymers for the treatment of sickle cell disease |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL105100C (cg-RX-API-DMAC7.html) * | 1958-04-30 | |||
| CH543472A (fr) * | 1969-01-31 | 1973-10-31 | Orchimed Sa | Procédé pour la préparation d'acides phénoxyalcoyl-carboxyliques |
| CH550776A (de) | 1971-03-05 | 1974-06-28 | Ciba Geigy Ag | Herstellung neuer bis-stilbenverbindungen. |
| DE2209128C3 (de) | 1971-03-05 | 1981-10-22 | CIBA-GEIGY AG, 4002 Basel | Bis-Stilbenverbindungen, Verfahren zu deren Herstellung und deren Verwendung als optische Aufheller |
| GB1511645A (en) | 1974-05-31 | 1978-05-24 | Univ Ife | Sickle cell anaemia treatment |
| US4137309A (en) * | 1976-10-14 | 1979-01-30 | The Procter & Gamble Company | Therapeutic treatment |
-
1980
- 1980-06-27 ZA ZA00803880A patent/ZA803880B/xx unknown
- 1980-06-27 MW MW23/80A patent/MW2380A1/xx unknown
- 1980-06-27 IT IT49108/80A patent/IT1133025B/it active
- 1980-06-27 KR KR1019800002541A patent/KR850000073B1/ko not_active Expired
- 1980-06-27 DE DE8080103657T patent/DE3061269D1/de not_active Expired
- 1980-06-27 JP JP8764580A patent/JPS5649335A/ja active Granted
- 1980-06-27 DK DK279780A patent/DK159770C/da not_active IP Right Cessation
- 1980-06-27 EP EP80103657A patent/EP0022229B1/en not_active Expired
- 1980-06-27 FI FI802052A patent/FI71929C/fi not_active IP Right Cessation
- 1980-06-27 GB GB8021219A patent/GB2053218B/en not_active Expired
- 1980-06-27 IL IL60422A patent/IL60422A/xx not_active IP Right Cessation
- 1980-06-27 GR GR62311A patent/GR68748B/el unknown
- 1980-06-27 ZW ZW144/80A patent/ZW14480A1/xx unknown
- 1980-06-27 HU HU801601A patent/HU190774B/hu not_active IP Right Cessation
- 1980-06-27 AU AU59697/80A patent/AU545274B2/en not_active Ceased
- 1980-06-27 ZM ZM57/80A patent/ZM5780A1/xx unknown
- 1980-08-09 OA OA57193A patent/OA06699A/xx unknown
-
1981
- 1981-06-09 US US06/271,950 patent/US4410537A/en not_active Expired - Lifetime
-
1984
- 1984-03-13 KR KR1019840001263A patent/KR850000072B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ZW14480A1 (en) | 1982-03-17 |
| KR850000073B1 (ko) | 1985-02-18 |
| EP0022229A1 (en) | 1981-01-14 |
| KR840004668A (ko) | 1984-10-22 |
| IL60422A0 (en) | 1980-09-16 |
| ZA803880B (en) | 1982-02-24 |
| GB2053218A (en) | 1981-02-04 |
| ZM5780A1 (en) | 1983-11-21 |
| US4410537A (en) | 1983-10-18 |
| KR830002693A (ko) | 1983-05-30 |
| HU190774B (en) | 1986-11-28 |
| GB2053218B (en) | 1984-01-25 |
| MW2380A1 (en) | 1982-03-10 |
| GR68748B (cg-RX-API-DMAC7.html) | 1982-02-16 |
| FI802052A7 (fi) | 1980-12-30 |
| FI71929C (fi) | 1987-03-09 |
| FI71929B (fi) | 1986-11-28 |
| DK279780A (da) | 1980-12-30 |
| DE3061269D1 (en) | 1983-01-13 |
| KR850000072B1 (ko) | 1985-02-18 |
| AU5969780A (en) | 1981-01-08 |
| DK159770B (da) | 1990-12-03 |
| JPS5649335A (en) | 1981-05-02 |
| IT1133025B (it) | 1986-07-09 |
| OA06699A (fr) | 1982-05-31 |
| IT8049108A0 (it) | 1980-06-27 |
| IL60422A (en) | 1984-06-29 |
| DK159770C (da) | 1991-04-22 |
| AU545274B2 (en) | 1985-07-11 |
| EP0022229B1 (en) | 1982-12-08 |
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