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 medecine

Info

Publication number: CA1242713A
Authority: CA; Canada
Prior art keywords: hemin; water; arginine; lysine; arginate
Prior art date: 1984-12-12
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

Application number

CA000473658A

Other languages

English (en)

Inventor

Raimo A. Tenhunen

Reino O. Tokola

Ritva L.A. Penttila

Grels D. Ingberg

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Huhtamaki Oyj

Original Assignee

Huhtamaki Oyj

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.)

1984-12-12

Filing date

1985-02-06

Publication date

1988-10-04

1985-02-06 Application filed by Huhtamaki Oyj filed Critical Huhtamaki Oyj

1988-10-04 Application granted granted Critical

1988-10-04 Publication of CA1242713A publication Critical patent/CA1242713A/fr

Status Expired legal-status Critical Current

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 or vitamin B12

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Hematology (AREA)
Pharmacology & Pharmacy (AREA)
Diabetes (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (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)

CA000473658A 1984-12-12 1985-02-06 Procede de preparation d'un nouveau complexe d'hemine utilisable en medecine Expired CA1242713A (fr)

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 (11)

* Cited by examiner, † Cited by third party
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.
RU2200016C2 (ru) *	2000-11-09	2003-03-10	Всероссийская научно-исследовательская опытная станция пантового оленеводства	Способ производства пантогематогена
RU2179027C1 (ru) *	2000-12-18	2002-02-10	Кочерга Олег Иванович	Гематоген
RU2186571C1 (ru) *	2001-01-15	2002-08-10	Карякин Александр Вадимович	Детские лекарственные формы, стимулирующие кроветворение
US7994217B2 (en) *	2002-05-02	2011-08-09	Xanodyne Pharmaceuticals, Inc.	Prenatal multivitamin/multimineral supplement
RU2268058C2 (ru) *	2004-03-29	2006-01-20	Всероссийский научно-исследовательский институт пантового оленеводства (ВНИИПО)	Способ получения биологически активного продукта из пантов и крови оленя
RU2297841C2 (ru) *	2005-07-01	2007-04-27	Закрытое акционерное общество "Медицинский антидопинговый центр"	Лекарственное средство наружного применения и способ его получения
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
CN117546938B (zh) *	2023-10-29	2026-03-27	华中农业大学	血红素在植物基/微生物基蛋白模拟肉食品及生物铁强化型饮品中的应用

Family Cites Families (7)

* Cited by examiner, † Cited by third party
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 SE SE8406263A patent/SE457958B/sv not_active IP Right Cessation
- 1984-12-10 AT AT0390784A patent/AT389308B/de 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
JPS61172821A (ja)	1986-08-04
LU85716A1 (fr)	1985-07-24
SE457958B (sv)	1989-02-13
NL192682B (nl)	1997-08-01
DE3446887A1 (de)	1986-07-03
GB2168354B (en)	1988-12-07
AT389308B (de)	1989-11-27
FR2574662A1 (fr)	1986-06-20
GB8431398D0 (en)	1985-01-23
JPH0647541B2 (ja)	1994-06-22
FR2574662B1 (fr)	1990-03-02
SE8406263D0 (sv)	1984-12-10
BE901319A (fr)	1985-04-16
CH666273A5 (de)	1988-07-15
ATA390784A (de)	1989-04-15
DE3446887C2 (de)	1994-05-05
NL8403782A (nl)	1986-07-01
NL192682C (nl)	1997-12-02
SU1384188A3 (ru)	1988-03-23
GB2168354A (en)	1986-06-18
SE8406263L (sv)	1986-06-11

Legal Events

Date	Code	Title	Description
2005-10-04	MKEX	Expiry

Publication	Publication Date	Title
CA1242713A (fr)	1988-10-04	Procede de preparation d'un nouveau complexe d'hemine utilisable en medecine
US5069913A (en)	1991-12-03	Vanadium-peroxide compositions as insulin mimickers
CA2189528A1 (fr)	1995-11-23	Procedes d'utilisation de catalyseurs de decomposition deperoxynitrite et compositions pharmaceutiques a cet effet
EP0172577A1 (fr)	1986-02-26	Superoxyde dismutase, sa préparation et compostions pharmaceutiques la contenant
US5008388A (en)	1991-04-16	Process for preparation of a new hemin complex
US20090247492A1 (en)	2009-10-01	Manganese based organometallic complexes, pharmaceutical compositions and dietetic products
US4110441A (en)	1978-08-29	Gamma-l-glutamyl cholamine phosphate
KR20010023870A (ko)	2001-03-26	모노히드록사메이트의 바나듐 착물 및 이를 포함하는 약제조성물
US3903285A (en)	1975-09-02	Method for treating parkinsonism
White	1941	Growth-inhibition produced in rats by the oral administration of sodium benzoate: Effects of various dietary supplements
CN111820406B (zh)	2022-07-19	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)	1983-04-18	Ｎ−アシル−ｌ−アスパルチルタウリンを含有する医薬
CS247187B2 (cs)	1986-12-18	Způsob výroby nového horninového komplexu
DE2819457A1 (de)	1978-11-09	L- oder dl-phenylglycin-derivate, verfahren zu ihrer herstellung und solche derivate enthaltende mittel
US4959394A (en)	1990-09-25	Novel Guanidinium aspartates
DK172797B1 (da)	1999-07-19	Fremgangsmåde til fremstilling af et fysiologisk virksomt, vandopløseligt hæminkompleks samt anvendelse af dette til fremst
KR20050052366A (ko)	2005-06-02	유기태 금속이 축적된 미생물 제제 및 이의 제조 방법
KR0144442B1 (ko)	1998-07-15	수용성 비스무스 화합물 및 그의 제조 방법
DD249028A5 (de)	1987-08-26	Verfahren zur herstellung einer neuen haemin-komplexverbindung mit medizinischer verwendbarkeit
JP3406334B2 (ja)	2003-05-12	チロシン特異的リン酸化酵素阻害剤及び制癌剤
PL144343B1 (en)	1988-05-31	Method of obtaining novel complex compound of hemine with l-arginin or l-lysine
NO160923B (no)	1989-03-06	Analogifremgangsmaate for fremstilling av fysiologisk virksomt, vannopploeselig hemin-arginat og hemin-lysinat.
CN119306777A (zh)	2025-01-14	一种二氟代苯磺酰莫诺苷衍生物及其合成方法和应用
Finn	1986	The Physical Properties of Chemically Modified Catalases
JPH02169519A (ja)	1990-06-29	血管拡張剤