CA1242713A - Procede de preparation d'un nouveau complexe d'hemine utilisable en medecine - Google Patents
Procede de preparation d'un nouveau complexe d'hemine utilisable en medecineInfo
- Publication number
- CA1242713A CA1242713A CA000473658A CA473658A CA1242713A CA 1242713 A CA1242713 A CA 1242713A CA 000473658 A CA000473658 A CA 000473658A CA 473658 A CA473658 A CA 473658A CA 1242713 A CA1242713 A CA 1242713A
- Authority
- CA
- Canada
- Prior art keywords
- hemin
- water
- arginine
- lysine
- arginate
- 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
- 229940025294 hemin Drugs 0.000 title claims abstract description 96
- BTIJJDXEELBZFS-QDUVMHSLSA-K hemin Chemical compound CC1=C(CCC(O)=O)C(C=C2C(CCC(O)=O)=C(C)\C(N2[Fe](Cl)N23)=C\4)=N\C1=C/C2=C(C)C(C=C)=C3\C=C/1C(C)=C(C=C)C/4=N\1 BTIJJDXEELBZFS-QDUVMHSLSA-K 0.000 title claims abstract description 88
- 238000000034 method Methods 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 title abstract description 10
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 230000008569 process Effects 0.000 title description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims abstract description 18
- 229930064664 L-arginine Natural products 0.000 claims abstract description 18
- 235000014852 L-arginine Nutrition 0.000 claims abstract description 18
- KDXKERNSBIXSRK-UHFFFAOYSA-M lysinate Chemical compound NCCCCC(N)C([O-])=O KDXKERNSBIXSRK-UHFFFAOYSA-M 0.000 claims abstract description 10
- 238000002347 injection Methods 0.000 claims abstract description 7
- 239000007924 injection Substances 0.000 claims abstract description 7
- 238000011282 treatment Methods 0.000 claims abstract description 7
- 208000007502 anemia Diseases 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 5
- 239000002775 capsule Substances 0.000 claims abstract description 4
- 235000001014 amino acid Nutrition 0.000 claims abstract 6
- 150000001413 amino acids Chemical class 0.000 claims abstract 6
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 18
- 239000004472 Lysine Substances 0.000 claims description 9
- 235000019766 L-Lysine Nutrition 0.000 claims description 8
- -1 hemin compound Chemical class 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 241000097929 Porphyria Species 0.000 abstract description 11
- 208000010642 Porphyrias Diseases 0.000 abstract description 11
- 239000011877 solvent mixture Substances 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract 1
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 abstract 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 26
- 229910052742 iron Inorganic materials 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 10
- 102000004020 Oxygenases Human genes 0.000 description 8
- 108090000417 Oxygenases Proteins 0.000 description 8
- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 description 6
- 201000005060 thrombophlebitis Diseases 0.000 description 6
- BMUDPLZKKRQECS-UHFFFAOYSA-K 3-[18-(2-carboxyethyl)-8,13-bis(ethenyl)-3,7,12,17-tetramethylporphyrin-21,24-diid-2-yl]propanoic acid iron(3+) hydroxide Chemical compound [OH-].[Fe+3].[N-]1C2=C(C)C(CCC(O)=O)=C1C=C([N-]1)C(CCC(O)=O)=C(C)C1=CC(C(C)=C1C=C)=NC1=CC(C(C)=C1C=C)=NC1=C2 BMUDPLZKKRQECS-UHFFFAOYSA-K 0.000 description 5
- 102000001554 Hemoglobins Human genes 0.000 description 5
- 108010054147 Hemoglobins Proteins 0.000 description 5
- 229940109738 hematin Drugs 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 206010022971 Iron Deficiencies Diseases 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004475 Arginine Substances 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 208000031162 sideroblastic anemia Diseases 0.000 description 3
- 210000003462 vein Anatomy 0.000 description 3
- GWZYPXHJIZCRAJ-UHFFFAOYSA-N Biliverdin Natural products CC1=C(C=C)C(=C/C2=NC(=Cc3[nH]c(C=C/4NC(=O)C(=C4C)C=C)c(C)c3CCC(=O)O)C(=C2C)CCC(=O)O)NC1=O GWZYPXHJIZCRAJ-UHFFFAOYSA-N 0.000 description 2
- RCNSAJSGRJSBKK-NSQVQWHSSA-N Biliverdin IX Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(\C=C/2C(=C(C)C(=C/C=3C(=C(C=C)C(=O)N=3)C)/N\2)CCC(O)=O)N1 RCNSAJSGRJSBKK-NSQVQWHSSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000008575 L-amino acids Chemical class 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 108010067549 Methemalbumin Proteins 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- 235000009697 arginine Nutrition 0.000 description 2
- QBUVFDKTZJNUPP-UHFFFAOYSA-N biliverdin-IXalpha Natural products N1C(=O)C(C)=C(C=C)C1=CC1=C(C)C(CCC(O)=O)=C(C=C2C(=C(C)C(C=C3C(=C(C=C)C(=O)N3)C)=N2)CCC(O)=O)N1 QBUVFDKTZJNUPP-UHFFFAOYSA-N 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000004064 dysfunction Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000320 mechanical mixture Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 1
- WNDUPUMWHYAJOR-SADXPQEKSA-K (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;2-hydroxypropane-1,2,3-tricarboxylate;iron(3+) Chemical compound [Fe+3].OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WNDUPUMWHYAJOR-SADXPQEKSA-K 0.000 description 1
- 108010017500 Biliverdin reductase Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 108010052832 Cytochromes Proteins 0.000 description 1
- 102000018832 Cytochromes Human genes 0.000 description 1
- SGCGMORCWLEJNZ-UWVGGRQHSA-N His-His Chemical compound C([C@H]([NH3+])C(=O)N[C@@H](CC=1NC=NC=1)C([O-])=O)C1=CN=CN1 SGCGMORCWLEJNZ-UWVGGRQHSA-N 0.000 description 1
- 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 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 239000005569 Iron sulphate Substances 0.000 description 1
- 208000015710 Iron-Deficiency Anemia Diseases 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 1
- 208000003056 Vitamin B6 deficiency Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000567 anti-anemic effect Effects 0.000 description 1
- 102000004558 biliverdin reductase Human genes 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000009088 enzymatic function Effects 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 108060003196 globin Proteins 0.000 description 1
- 102000018146 globin Human genes 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- JHGVLAHJJNKSAW-UHFFFAOYSA-N herniarin Natural products C1CC(=O)OC2=CC(OC)=CC=C21 JHGVLAHJJNKSAW-UHFFFAOYSA-N 0.000 description 1
- 108010028295 histidylhistidine Proteins 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229940082629 iron antianemic preparations Drugs 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- VRIVJOXICYMTAG-IYEMJOQQSA-L iron(ii) gluconate Chemical compound [Fe+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O VRIVJOXICYMTAG-IYEMJOQQSA-L 0.000 description 1
- 235000018977 lysine Nutrition 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 229960001416 pilocarpine Drugs 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229940070376 protein Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012088 reference solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon, or a metal, e.g. chelates, vitamin B12
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Medicinal Chemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB08431398A GB2168354B (en) | 1984-12-12 | 1984-12-12 | Hemin compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1242713A true CA1242713A (fr) | 1988-10-04 |
Family
ID=10571084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000473658A Expired CA1242713A (fr) | 1984-12-12 | 1985-02-06 | Procede de preparation d'un nouveau complexe d'hemine utilisable en medecine |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPH0647541B2 (fr) |
| AT (1) | AT389308B (fr) |
| BE (1) | BE901319A (fr) |
| CA (1) | CA1242713A (fr) |
| CH (1) | CH666273A5 (fr) |
| DE (1) | DE3446887C2 (fr) |
| FR (1) | FR2574662B1 (fr) |
| GB (1) | GB2168354B (fr) |
| LU (1) | LU85716A1 (fr) |
| NL (1) | NL192682C (fr) |
| SE (1) | SE457958B (fr) |
| SU (1) | SU1384188A3 (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0645681B2 (ja) * | 1986-02-05 | 1994-06-15 | 美浜 久春 | 修飾ヘム |
| IT1245890B (it) * | 1991-04-12 | 1994-10-25 | Alfa Wassermann Spa | Formulazioni farmaceutiche per uso orale gastroresistenti contenenti acidi biliari. |
| US7994217B2 (en) * | 2002-05-02 | 2011-08-09 | Xanodyne Pharmaceuticals, Inc. | Prenatal multivitamin/multimineral supplement |
| RU2611636C1 (ru) * | 2016-02-25 | 2017-02-28 | Федеральное государственное бюджетное образовательное учреждение высшего образования Новосибирский государственный аграрный университет | Гематоген |
| RU2671633C1 (ru) * | 2017-11-30 | 2018-11-06 | Общество с ограниченной ответственностью "ОКТАВА ХОЛДИНГ" | Высокоэффективный гематоген |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2912M (fr) * | 1963-07-24 | 1964-11-09 | Rech S Pharma E R P H A R Soc | Dichlorhydrate d'hématoporphyrinate de procaine. |
| JPS4930521A (fr) * | 1972-07-17 | 1974-03-19 | ||
| JPS5144623A (ja) * | 1974-10-14 | 1976-04-16 | Green Cross Corp | Chushayoasechirusarichirusanenno seiho |
| DE2527158A1 (de) * | 1975-06-18 | 1976-12-23 | Herz Eberhard | Arzneimittel zur behandlung von infektionskrankheiten und von nicht nachweisbar durch mikroorganismen ausgeloeste entzuendungen in der human- und veterinaermedizin |
| JPS6021570B2 (ja) * | 1978-07-04 | 1985-05-28 | 三共株式会社 | ド−パ類の高濃度製剤の製法 |
| JPS5780317A (en) * | 1980-11-05 | 1982-05-19 | Sumitomo Chem Co Ltd | Preparation of pharmaceutical composition for injection |
| JPS57209211A (en) * | 1981-06-18 | 1982-12-22 | Shiseido Co Ltd | Antimicrobial composition |
-
1984
- 1984-12-10 AT AT0390784A patent/AT389308B/de not_active IP Right Cessation
- 1984-12-10 SE SE8406263A patent/SE457958B/sv not_active IP Right Cessation
- 1984-12-12 GB GB08431398A patent/GB2168354B/en not_active Expired
- 1984-12-13 NL NL8403782A patent/NL192682C/nl not_active IP Right Cessation
- 1984-12-14 FR FR848419134A patent/FR2574662B1/fr not_active Expired - Lifetime
- 1984-12-19 BE BE0/214195A patent/BE901319A/fr not_active IP Right Cessation
- 1984-12-21 DE DE3446887A patent/DE3446887C2/de not_active Expired - Fee Related
- 1984-12-28 LU LU85716A patent/LU85716A1/fr unknown
-
1985
- 1985-01-07 CH CH45/85A patent/CH666273A5/de not_active IP Right Cessation
- 1985-01-09 SU SU3831925A patent/SU1384188A3/ru active
- 1985-01-23 JP JP60009302A patent/JPH0647541B2/ja not_active Expired - Fee Related
- 1985-02-06 CA CA000473658A patent/CA1242713A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ATA390784A (de) | 1989-04-15 |
| SE8406263L (sv) | 1986-06-11 |
| BE901319A (fr) | 1985-04-16 |
| SU1384188A3 (ru) | 1988-03-23 |
| JPS61172821A (ja) | 1986-08-04 |
| NL8403782A (nl) | 1986-07-01 |
| FR2574662A1 (fr) | 1986-06-20 |
| GB2168354A (en) | 1986-06-18 |
| DE3446887C2 (de) | 1994-05-05 |
| GB8431398D0 (en) | 1985-01-23 |
| GB2168354B (en) | 1988-12-07 |
| SE457958B (sv) | 1989-02-13 |
| CH666273A5 (de) | 1988-07-15 |
| JPH0647541B2 (ja) | 1994-06-22 |
| NL192682B (nl) | 1997-08-01 |
| LU85716A1 (fr) | 1985-07-24 |
| NL192682C (nl) | 1997-12-02 |
| AT389308B (de) | 1989-11-27 |
| DE3446887A1 (de) | 1986-07-03 |
| FR2574662B1 (fr) | 1990-03-02 |
| SE8406263D0 (sv) | 1984-12-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5312404B2 (ja) | 置換されたポルフィリン類 | |
| EP0264278B1 (fr) | Compositions de vanadium et peroxyde comme médicaments imitateurs de l'insuline | |
| CA2189528A1 (fr) | Procedes d'utilisation de catalyseurs de decomposition deperoxynitrite et compositions pharmaceutiques a cet effet | |
| CN109678715B (zh) | 2-(1-酰氧正戊基)苯甲酸与碱性氨基酸或氨基胍形成的盐、其制备方法及用途 | |
| EP0172577A1 (fr) | Superoxyde dismutase, sa préparation et compostions pharmaceutiques la contenant | |
| CA1242713A (fr) | Procede de preparation d'un nouveau complexe d'hemine utilisable en medecine | |
| US5008388A (en) | Process for preparation of a new hemin complex | |
| US20090247492A1 (en) | Manganese based organometallic complexes, pharmaceutical compositions and dietetic products | |
| KR20010023870A (ko) | 모노히드록사메이트의 바나듐 착물 및 이를 포함하는 약제조성물 | |
| US3903285A (en) | Method for treating parkinsonism | |
| CN111820406B (zh) | 多肽白藜芦醇制剂及其制备方法和应用以及包含其的保健品或药物组合物 | |
| JPS5865214A (ja) | Ｎ−アシル−ｌ−アスパルチルタウリンを含有する医薬 | |
| FI97950B (fi) | Menetelmä vitamiinituotteen valmistamiseksi | |
| DE2819457A1 (de) | L- oder dl-phenylglycin-derivate, verfahren zu ihrer herstellung und solche derivate enthaltende mittel | |
| US4959394A (en) | Novel Guanidinium aspartates | |
| DK172797B1 (da) | Fremgangsmåde til fremstilling af et fysiologisk virksomt, vandopløseligt hæminkompleks samt anvendelse af dette til fremst | |
| CS247187B2 (cs) | Způsob výroby nového horninového komplexu | |
| KR0144442B1 (ko) | 수용성 비스무스 화합물 및 그의 제조 방법 | |
| DD249028A5 (de) | Verfahren zur herstellung einer neuen haemin-komplexverbindung mit medizinischer verwendbarkeit | |
| JP3406334B2 (ja) | チロシン特異的リン酸化酵素阻害剤及び制癌剤 | |
| PL144343B1 (en) | Method of obtaining novel complex compound of hemine with l-arginin or l-lysine | |
| NO160923B (no) | Analogifremgangsmaate for fremstilling av fysiologisk virksomt, vannopploeselig hemin-arginat og hemin-lysinat. | |
| Finn | The Physical Properties of Chemically Modified Catalases | |
| GB2060638A (en) | Lysine and arginine 5-(2,4-difluorophenyl)-2-hydrobenzoic acid salts, pharmaceutical compositions containing them and their use |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |