CY1504A - Iron complexes of 3-hydroxypyrid-2-and-4-ones - Google Patents

Iron complexes of 3-hydroxypyrid-2-and-4-ones Download PDF

Info

Publication number: CY1504A
Authority: CY; Cyprus
Prior art keywords: group; hydroxy; aliphatic; aliphatic hydrocarbon; iron
Prior art date: 1983-03-24

Application number

CY1504A

Other languages

English (en)

Inventor

Robert Charles Hider

George Kontoghiorghes

Jack Silver

Michael Arthur Stockham

Original Assignee

Nat Res Dev

Priority date (The priority date 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 date listed.)

1983-03-24

Filing date

1984-03-20

Publication date

1990-08-03

1984-03-20 Application filed by Nat Res Dev filed Critical Nat Res Dev

1990-08-03 Publication of CY1504A publication Critical patent/CY1504A/en

Links

150000002505 iron Chemical class 0.000 title description 35
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 147
125000001931 aliphatic group Chemical group 0.000 claims description 104
150000001875 compounds Chemical class 0.000 claims description 87
229910052742 iron Inorganic materials 0.000 claims description 72
GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical compound OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 claims description 70
-1 aliphatic ester Chemical class 0.000 claims description 54
150000004698 iron complex Chemical class 0.000 claims description 53
229910052757 nitrogen Inorganic materials 0.000 claims description 41
125000004432 carbon atom Chemical group C* 0.000 claims description 40
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
125000001424 substituent group Chemical group 0.000 claims description 39
239000000243 solution Substances 0.000 claims description 35
125000004433 nitrogen atom Chemical group N* 0.000 claims description 31
239000007787 solid Substances 0.000 claims description 27
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
239000008194 pharmaceutical composition Substances 0.000 claims description 26
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
LQUSVSANJKHVTM-UHFFFAOYSA-N 3-hydroxy-3h-pyridin-4-one Chemical compound OC1C=NC=CC1=O LQUSVSANJKHVTM-UHFFFAOYSA-N 0.000 claims description 19
125000003545 alkoxy group Chemical group 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 17
150000002367 halogens Chemical class 0.000 claims description 17
229910052799 carbon Inorganic materials 0.000 claims description 16
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
238000010494 dissociation reaction Methods 0.000 claims description 15
230000005593 dissociations Effects 0.000 claims description 15
ZCUUVWCJGRQCMZ-UHFFFAOYSA-N 3-hydroxypyridin-4-one Natural products OC1=CC=NC=C1O ZCUUVWCJGRQCMZ-UHFFFAOYSA-N 0.000 claims description 14
LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
125000004429 atom Chemical group 0.000 claims description 12
230000007935 neutral effect Effects 0.000 claims description 12
125000002252 acyl group Chemical group 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 11
230000002378 acidificating effect Effects 0.000 claims description 10
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 9
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 9
LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 9
210000002784 stomach Anatomy 0.000 claims description 9
229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 8
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 8
150000008431 aliphatic amides Chemical class 0.000 claims description 7
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 6
210000000936 intestine Anatomy 0.000 claims description 6
125000002015 acyclic group Chemical group 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
150000002500 ions Chemical class 0.000 claims description 5
239000000797 iron chelating agent Substances 0.000 claims description 5
229940075525 iron chelating agent Drugs 0.000 claims description 5
QVXIZJHZWYLVET-UHFFFAOYSA-N 3-hydroxy-2-methyl-3h-pyridin-4-one Chemical compound CC1=NC=CC(=O)C1O QVXIZJHZWYLVET-UHFFFAOYSA-N 0.000 claims description 4
125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
239000000463 material Substances 0.000 claims description 3
239000000725 suspension Substances 0.000 claims description 3
LIPRKYKMVQPYPG-UHFFFAOYSA-N 3-Hydroxy-2H-pyran-2-one Chemical compound OC1=CC=COC1=O LIPRKYKMVQPYPG-UHFFFAOYSA-N 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
230000003111 delayed effect Effects 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
229910021653 sulphate ion Inorganic materials 0.000 claims description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 2
BJKPHFJURKOFKA-UHFFFAOYSA-N 2-(2-oxopyridin-1-yl)-n-propylacetamide Chemical compound CCCNC(=O)CN1C=CC=CC1=O BJKPHFJURKOFKA-UHFFFAOYSA-N 0.000 claims 1
CHDPWGXKKUGCNC-UHFFFAOYSA-N 3-hydroxy-2,6-dimethyl-3h-pyridin-4-one Chemical compound CC1=CC(=O)C(O)C(C)=N1 CHDPWGXKKUGCNC-UHFFFAOYSA-N 0.000 claims 1
MEDNCKZHWTVGSY-UHFFFAOYSA-N 3-hydroxy-6-methyl-3h-pyridin-4-one Chemical compound CC1=CC(=O)C(O)C=N1 MEDNCKZHWTVGSY-UHFFFAOYSA-N 0.000 claims 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 claims 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims 1
125000004849 alkoxymethyl group Chemical group 0.000 claims 1
229940072107 ascorbate Drugs 0.000 claims 1
235000010323 ascorbic acid Nutrition 0.000 claims 1
239000011668 ascorbic acid Substances 0.000 claims 1
239000000839 emulsion Substances 0.000 claims 1
229940050410 gluconate Drugs 0.000 claims 1
125000004970 halomethyl group Chemical group 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
239000011343 solid material Substances 0.000 claims 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
239000000203 mixture Substances 0.000 description 53
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
238000002360 preparation method Methods 0.000 description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
238000000034 method Methods 0.000 description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
239000013078 crystal Substances 0.000 description 16
238000002390 rotary evaporation Methods 0.000 description 13
230000000694 effects Effects 0.000 description 12
150000001721 carbon Chemical group 0.000 description 11
125000004185 ester group Chemical group 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
239000002904 solvent Substances 0.000 description 10
238000006467 substitution reaction Methods 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
150000001450 anions Chemical class 0.000 description 9
210000003743 erythrocyte Anatomy 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
238000005192 partition Methods 0.000 description 9
241000282414 Homo sapiens Species 0.000 description 8
208000015710 Iron-Deficiency Anemia Diseases 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000002253 acid Substances 0.000 description 8
208000007502 anemia Diseases 0.000 description 8
KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
VEYIMQVTPXPUHA-UHFFFAOYSA-N 3-hydroxypyran-4-one Chemical compound OC1=COC=CC1=O VEYIMQVTPXPUHA-UHFFFAOYSA-N 0.000 description 7
235000011167 hydrochloric acid Nutrition 0.000 description 7
229960000443 hydrochloric acid Drugs 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
UWINDMSCWSNWED-UHFFFAOYSA-N 2-methyl-3h-pyridin-4-one Chemical compound CC1=NC=CC(=O)C1 UWINDMSCWSNWED-UHFFFAOYSA-N 0.000 description 6
NQOJWZRPLXJDPX-UHFFFAOYSA-N 2-methylpyrone Natural products CC1=CC(=O)C=CO1 NQOJWZRPLXJDPX-UHFFFAOYSA-N 0.000 description 6
125000003368 amide group Chemical group 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
238000013459 approach Methods 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
230000008901 benefit Effects 0.000 description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
150000001768 cations Chemical class 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 5
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 5
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
239000006227 byproduct Substances 0.000 description 5
238000009472 formulation Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
241000282412 Homo Species 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
241000700159 Rattus Species 0.000 description 4
239000007983 Tris buffer Substances 0.000 description 4
239000002775 capsule Substances 0.000 description 4
238000005538 encapsulation Methods 0.000 description 4
150000002148 esters Chemical group 0.000 description 4
229940052303 ethers for general anesthesia Drugs 0.000 description 4
150000002430 hydrocarbons Chemical group 0.000 description 4
239000002609 medium Substances 0.000 description 4
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
238000007911 parenteral administration Methods 0.000 description 4
235000015108 pies Nutrition 0.000 description 4
210000000813 small intestine Anatomy 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000008247 solid mixture Substances 0.000 description 4
IFMPLEKNXYHLQF-UHFFFAOYSA-N 1-acetyl-3-hydroxypyridin-2-one Chemical compound CC(=O)N1C=CC=C(O)C1=O IFMPLEKNXYHLQF-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
LENZDBCJOHFCAS-UHFFFAOYSA-O Htris Chemical compound OCC([NH3+])(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-O 0.000 description 3
206010065973 Iron Overload Diseases 0.000 description 3
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
241000282887 Suidae Species 0.000 description 3
102000004338 Transferrin Human genes 0.000 description 3
108090000901 Transferrin Proteins 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
108010054176 apotransferrin Proteins 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
229940073608 benzyl chloride Drugs 0.000 description 3
239000000872 buffer Substances 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000011248 coating agent Substances 0.000 description 3
238000000576 coating method Methods 0.000 description 3
229960004132 diethyl ether Drugs 0.000 description 3
XSSKVHCYVBXLKS-UHFFFAOYSA-N ethyl 2-(3-hydroxy-2-oxopyridin-1-yl)acetate Chemical compound CCOC(=O)CN1C=CC=C(O)C1=O XSSKVHCYVBXLKS-UHFFFAOYSA-N 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
229940093499 ethyl acetate Drugs 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
150000002334 glycols Chemical class 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
150000002506 iron compounds Chemical class 0.000 description 3
239000002502 liposome Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000012528 membrane Substances 0.000 description 3
230000001575 pathological effect Effects 0.000 description 3
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000012360 testing method Methods 0.000 description 3
239000012581 transferrin Substances 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
239000011701 zinc Substances 0.000 description 3
UUDALWDRIFYZPM-UHFFFAOYSA-N 1h-pyridine-2,4-dione Chemical compound O=C1CC(=O)C=CN1 UUDALWDRIFYZPM-UHFFFAOYSA-N 0.000 description 2
HHEJKMIMUJVQPB-UHFFFAOYSA-N 2-(3-hydroxy-2-methyl-4-oxopyridin-1-yl)acetic acid Chemical compound CC1=C(O)C(=O)C=CN1CC(O)=O HHEJKMIMUJVQPB-UHFFFAOYSA-N 0.000 description 2
VOVOSCSRCMNBBO-UHFFFAOYSA-N 2-methyl-3H-pyridin-4-one hydrochloride Chemical compound Cl.CC1=NC=CC(C1)=O VOVOSCSRCMNBBO-UHFFFAOYSA-N 0.000 description 2
ZJDRWNJIMXVJQG-UHFFFAOYSA-N 3-hydroxy-1-(2-hydroxyethyl)-2-methylpyridin-4-one Chemical compound CC1=C(O)C(=O)C=CN1CCO ZJDRWNJIMXVJQG-UHFFFAOYSA-N 0.000 description 2
XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
MPOYBFYHRQBZPM-UHFFFAOYSA-N 3h-pyridin-4-one Chemical compound O=C1CC=NC=C1 MPOYBFYHRQBZPM-UHFFFAOYSA-N 0.000 description 2
XATJWQRIODISIG-UHFFFAOYSA-N 5-hydroxy-2-(hydroxymethyl)-1-methylpyridin-4-one Chemical compound CN1C=C(O)C(=O)C=C1CO XATJWQRIODISIG-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
206010002042 Anaemia deficiencies Diseases 0.000 description 2
241001137251 Corvidae Species 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
239000004471 Glycine Substances 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
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CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
102100029469 WD repeat and HMG-box DNA-binding protein 1 Human genes 0.000 description 2
101710097421 WD repeat and HMG-box DNA-binding protein 1 Proteins 0.000 description 2
FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 2
125000004448 alkyl carbonyl group Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000002585 base Substances 0.000 description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
230000027455 binding Effects 0.000 description 2
230000000536 complexating effect Effects 0.000 description 2
239000012043 crude product Substances 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
125000001033 ether group Chemical group 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
229940006199 ferric cation Drugs 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
230000012010 growth Effects 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
238000011534 incubation Methods 0.000 description 2
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XTEVJAUXUQKGOW-UHFFFAOYSA-N methyl 3-(3-hydroxy-2-methyl-4-oxopyridin-1-yl)propanoate;hydrochloride Chemical compound Cl.COC(=O)CCN1C=CC(=O)C(O)=C1C XTEVJAUXUQKGOW-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- 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

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Hematology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Obesity (AREA)
Pyridine Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrane Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

CY1504A 1983-03-24 1984-03-20 Iron complexes of 3-hydroxypyrid-2-and-4-ones CY1504A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB838308055A GB8308055D0 (en)	1983-03-24	1983-03-24	Pharmaceutical compositions

Publications (1)

Publication Number	Publication Date
CY1504A true CY1504A (en)	1990-08-03

Family

ID=10540099

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CY1504A CY1504A (en)	1983-03-24	1984-03-20	Iron complexes of 3-hydroxypyrid-2-and-4-ones

Country Status (9)

Country	Link
US (2)	US4650793A (da)
EP (1)	EP0120670B1 (da)
JP (1)	JPH0625120B2 (da)
CY (1)	CY1504A (da)
DE (1)	DE3475706D1 (da)
DK (1)	DK159305C (da)
GB (2)	GB8308055D0 (da)
HK (1)	HK5190A (da)
SG (1)	SG54389G (da)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4912118A (en) *	1983-09-23	1990-03-27	National Research Development Corporation	Pharmaceutical compositions
GB8329043D0 (en) *	1983-10-31	1983-11-30	Hider R C	Pharmaceutical compositions
US5177068A (en) *	1984-04-19	1993-01-05	National Research Development Corporation	Pharmaceutical compositions
GB8410289D0 (en) *	1984-04-19	1984-05-31	Callingham B A	Pharmaceutical compositions
DE3826846A1 (de) *	1988-08-06	1990-02-08	Goedecke Ag	Alkoxy-4(1h)-pyridon-derivate, verfahren zu deren herstellung und deren verwendung als arzneimittel
GB9006522D0 (en) *	1990-03-23	1990-05-23	Hider Robert C	Metal complexes
GB9209078D0 (en) *	1992-04-27	1992-06-10	Hider Robert C	Pharmaceutical compositions
GB9217099D0 (en) *	1992-08-12	1992-09-23	British Tech Group	Pharmaceutical compositions
EP0833627B1 (en)	1995-06-10	2004-08-18	Vitra Pharmaceuticals Ltd.	Iron compounds, compositions, methods of making the same and uses thereof
EP0767145B1 (en)	1995-10-06	2000-03-15	Calgon Corporation	Use of a synergistic composition for scale control
GB9625638D0 (en) *	1996-12-10	1997-01-29	Cenes Ltd	Therapeutic antioxidants for alzheimer's diease
GB9723078D0 (en) *	1997-10-31	1998-01-07	Cerebrus Ltd	Chemical compounds
US6294152B1 (en) *	1999-01-11	2001-09-25	The University Of Toledo	Iron(III) complexes as contrast agents for image enhancement in magnetic resonance imaging
US6767741B1 (en) *	1999-08-27	2004-07-27	Invitrogen Corporation	Metal binding compounds and their use in cell culture medium compositions
AU2001287850A1 (en) *	2000-09-19	2002-04-02	Vitra Pharmaceuticals Limited	Iron compositions
GB0211500D0 (en) *	2002-05-18	2002-06-26	Vitra Pharmaceuticals Ltd	Method of forming iron hydroxypyrone compounds
CN101679263B (zh)	2007-03-28	2014-01-15	阿普泰克斯科技公司	去铁酮的氟化衍生物
EP2268282B1 (en)	2008-04-25	2014-10-29	Apotex Technologies Inc.	Liquid formulation for deferiprone with palatable taste
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1983
- 1983-03-24 GB GB838308055A patent/GB8308055D0/en active Pending
1984
- 1984-03-20 CY CY1504A patent/CY1504A/en unknown
- 1984-03-20 GB GB08407180A patent/GB2136806B/en not_active Expired
- 1984-03-20 DE DE8484301882T patent/DE3475706D1/de not_active Expired
- 1984-03-20 EP EP84301882A patent/EP0120670B1/en not_active Expired
- 1984-03-22 US US06/592,543 patent/US4650793A/en not_active Ceased
- 1984-03-23 DK DK165984A patent/DK159305C/da not_active IP Right Cessation
- 1984-03-24 JP JP59057186A patent/JPH0625120B2/ja not_active Expired - Lifetime
1989
- 1989-08-24 SG SG54389A patent/SG54389G/en unknown
1990
- 1990-01-25 HK HK51/90A patent/HK5190A/xx not_active IP Right Cessation
1995
- 1995-02-17 US US08/390,588 patent/USRE36831E/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
GB2136806A (en)	1984-09-26
JPH0625120B2 (ja)	1994-04-06
GB8407180D0 (en)	1984-04-26
US4650793A (en)	1987-03-17
DK159305B (da)	1990-10-01
DK159305C (da)	1991-03-04
EP0120670A1 (en)	1984-10-03
DK165984D0 (da)	1984-03-23
SG54389G (en)	1989-12-08
GB8308055D0 (en)	1983-05-05
USRE36831E (en)	2000-08-22
DE3475706D1 (en)	1989-01-26
GB2136806B (en)	1987-04-15
DK165984A (da)	1984-09-25
EP0120670B1 (en)	1988-12-21
HK5190A (en)	1990-02-02
JPS59181258A (ja)	1984-10-15

Publication	Publication Date	Title
CY1504A (en)	1990-08-03	Iron complexes of 3-hydroxypyrid-2-and-4-ones
EP0357150B1 (en)	1993-12-08	Pharmaceutical compositions
EP0138420B1 (en)	1989-11-29	Pharmaceutical compositions containing 1-hydroxypyrid-2-one derivatives
US5104865A (en)	1992-04-14	Iron complexes of hydroxypyridones useful for treating iron overload
JP3014109B2 (ja)	2000-02-28	合成的ｇｔｆクロム物質及びその方法
US4244968A (en)	1981-01-13	Treatment of arthritis and substances for use in such treatment
EP0145228B1 (en)	1991-02-06	Pharmaceutical compositions
CY1510A (en)	1990-08-03	Hydroxypyrid-2-and-4-ones
JPH0460987B2 (da)	1992-09-29
US4550101A (en)	1985-10-29	Iron complexes of hydroxy pyridones useful for treating iron deficiency anemia
CA1286844C (en)	1991-07-23	Pharmaceutical compositions
US5177068A (en)	1993-01-05	Pharmaceutical compositions
US5281578A (en)	1994-01-25	Gallium compounds
GB2117766A (en)	1983-10-19	Pharmaceutical compositions
USRE34313E (en)	1993-07-13	Pharmaceutical compositions
US3998964A (en)	1976-12-21	α-Amino-β-(N-benzylthiocarbamoylthio) propionic acid and therapeutic compositions
EP0305646B1 (en)	1996-11-13	3-Hydroxypyrid-4-ones and pharmaceutical compositions
FI62283C (fi)	1982-12-10	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara n-2'-karboxifenyl-4-klorantranilsyraderivat
DE3434562A1 (de)	1986-03-27	Verwendung von pyrrothinderivaten
US3433789A (en)	1969-03-18	S-benzoyloxymethyl-thiamines
KR820000809B1 (ko)	1982-05-11	신규 피리딘 유도체의 제조방법