NL192682C - Werkwijze voor het bereiden van een heminecomplex, en geneesmiddel. - Google Patents

Werkwijze voor het bereiden van een heminecomplex, en geneesmiddel. Download PDF

Info

Publication number: NL192682C
Authority: NL; Netherlands
Prior art keywords: hemin; hemine; crystalline; arginate; arginine
Prior art date: 1984-12-12

Application number

NL8403782A

Other languages

English (en)

Dutch (nl)

Other versions

NL8403782A (nl

NL192682B (nl

Original Assignee

Leiras Oy

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

1984-12-13

Publication date

1997-12-02

1984-12-13 Application filed by Leiras Oy filed Critical Leiras Oy

1986-07-01 Publication of NL8403782A publication Critical patent/NL8403782A/nl

1997-08-01 Publication of NL192682B publication Critical patent/NL192682B/xx

1997-12-02 Application granted granted Critical

1997-12-02 Publication of NL192682C publication Critical patent/NL192682C/nl

Links

229940025294 hemin Drugs 0.000 title claims description 56
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 description 54
238000000034 method Methods 0.000 title claims description 16
239000003814 drug Substances 0.000 title claims description 6
229940079593 drug Drugs 0.000 title description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 51
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
BTIJJDXEELBZFS-UHFFFAOYSA-K hemin Chemical compound [Cl-].[Fe+3].[N-]1C(C=C2C(=C(C)C(C=C3C(=C(C)C(=C4)[N-]3)C=C)=N2)C=C)=C(C)C(CCC(O)=O)=C1C=C1C(CCC(O)=O)=C(C)C4=N1 BTIJJDXEELBZFS-UHFFFAOYSA-K 0.000 claims description 29
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 15
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 14
229930064664 L-arginine Natural products 0.000 claims description 13
235000014852 L-arginine Nutrition 0.000 claims description 13
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
KDXKERNSBIXSRK-UHFFFAOYSA-M lysinate Chemical compound NCCCCC(N)C([O-])=O KDXKERNSBIXSRK-UHFFFAOYSA-M 0.000 claims description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 9
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 claims description 6
102000004190 Enzymes Human genes 0.000 claims description 6
108090000790 Enzymes Proteins 0.000 claims description 6
235000019766 L-Lysine Nutrition 0.000 claims description 6
239000004472 Lysine Substances 0.000 claims description 6
102000004020 Oxygenases Human genes 0.000 claims description 6
108090000417 Oxygenases Proteins 0.000 claims description 6
239000011877 solvent mixture Substances 0.000 claims description 6
238000002474 experimental method Methods 0.000 claims description 5
-1 hemine compound Chemical class 0.000 claims description 5
238000003756 stirring Methods 0.000 claims description 5
230000000694 effects Effects 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
239000000758 substrate Substances 0.000 claims description 4
239000004475 Arginine Substances 0.000 claims description 3
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 3
235000009697 arginine Nutrition 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
239000000126 substance Substances 0.000 claims 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 claims 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 claims description 2
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 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 claims description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
108010067549 Methemalbumin Proteins 0.000 claims 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims 2
108010017500 Biliverdin reductase Proteins 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
102000004558 biliverdin reductase Human genes 0.000 claims 1
230000000052 comparative effect Effects 0.000 claims 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
230000002255 enzymatic effect Effects 0.000 claims 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 30
229910052742 iron Inorganic materials 0.000 description 15
230000015572 biosynthetic process Effects 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 11
241000097929 Porphyria Species 0.000 description 10
208000010642 Porphyrias Diseases 0.000 description 10
239000000243 solution Substances 0.000 description 10
239000000203 mixture Substances 0.000 description 8
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
206010022971 Iron Deficiencies Diseases 0.000 description 5
229940109738 hematin Drugs 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
201000005060 thrombophlebitis Diseases 0.000 description 4
210000001519 tissue Anatomy 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
208000007502 anemia Diseases 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
235000013305 food Nutrition 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
230000001771 impaired effect Effects 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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
150000008575 L-amino acids Chemical class 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
235000005911 diet Nutrition 0.000 description 2
230000000378 dietary effect Effects 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
230000004064 dysfunction Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000012467 final product Substances 0.000 description 2
230000004054 inflammatory process 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
239000002904 solvent Substances 0.000 description 2
238000002560 therapeutic procedure Methods 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
102000018832 Cytochromes Human genes 0.000 description 1
108010052832 Cytochromes Proteins 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
102000008133 Iron-Binding Proteins Human genes 0.000 description 1
108010035210 Iron-Binding Proteins Proteins 0.000 description 1
208000015710 Iron-Deficiency Anemia Diseases 0.000 description 1
241001508687 Mustela erminea Species 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
230000001154 acute effect Effects 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
230000000567 anti-anemic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
210000000988 bone and bone Anatomy 0.000 description 1
239000002775 capsule Substances 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
230000007547 defect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
230000003292 diminished effect Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
210000003743 erythrocyte Anatomy 0.000 description 1
230000003203 everyday effect Effects 0.000 description 1
230000029142 excretion Effects 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
108060003196 globin Chemical group 0.000 description 1
102000018146 globin Human genes 0.000 description 1
208000035474 group of disease Diseases 0.000 description 1
230000002949 hemolytic effect Effects 0.000 description 1
108010028295 histidylhistidine Proteins 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229940082629 iron antianemic preparations Drugs 0.000 description 1
229910000358 iron sulfate Inorganic materials 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
238000004519 manufacturing process Methods 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
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000012088 reference solution Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 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 description 1
239000013589 supplement Substances 0.000 description 1
238000012360 testing method Methods 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)
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)

NL8403782A 1984-12-12 1984-12-13 Werkwijze voor het bereiden van een heminecomplex, en geneesmiddel. NL192682C (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8431398		1984-12-12
GB08431398A GB2168354B (en)	1984-12-12	1984-12-12	Hemin compound

Publications (3)

Publication Number	Publication Date
NL8403782A NL8403782A (nl)	1986-07-01
NL192682B NL192682B (nl)	1997-08-01
NL192682C true NL192682C (nl)	1997-12-02

Family

ID=10571084

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8403782A NL192682C (nl)	1984-12-12	1984-12-13	Werkwijze voor het bereiden van een heminecomplex, en geneesmiddel.

Country Status (12)

Country	Link
JP (1)	JPH0647541B2 (de)
AT (1)	AT389308B (de)
BE (1)	BE901319A (de)
CA (1)	CA1242713A (de)
CH (1)	CH666273A5 (de)
DE (1)	DE3446887C2 (de)
FR (1)	FR2574662B1 (de)
GB (1)	GB2168354B (de)
LU (1)	LU85716A1 (de)
NL (1)	NL192682C (de)
SE (1)	SE457958B (de)
SU (1)	SU1384188A3 (de)

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 (de) *	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/en not_active Expired

Also Published As

Publication number	Publication date
SE8406263D0 (sv)	1984-12-10
NL8403782A (nl)	1986-07-01
SE8406263L (sv)	1986-06-11
GB8431398D0 (en)	1985-01-23
FR2574662A1 (fr)	1986-06-20
SU1384188A3 (ru)	1988-03-23
SE457958B (sv)	1989-02-13
DE3446887A1 (de)	1986-07-03
FR2574662B1 (fr)	1990-03-02
CH666273A5 (de)	1988-07-15
GB2168354B (en)	1988-12-07
ATA390784A (de)	1989-04-15
LU85716A1 (fr)	1985-07-24
NL192682B (nl)	1997-08-01
JPH0647541B2 (ja)	1994-06-22
GB2168354A (en)	1986-06-18
CA1242713A (en)	1988-10-04
AT389308B (de)	1989-11-27
BE901319A (fr)	1985-04-16
JPS61172821A (ja)	1986-08-04
DE3446887C2 (de)	1994-05-05

Legal Events

Date	Code	Title	Description
1991-08-01	BA	A request for search or an international-type search has been filed
1991-09-02	BB	A search report has been drawn up
1992-02-03	BC	A request for examination has been filed
1996-12-02	CNR	Transfer of rights (patent application after its laying open for public inspection)	Free format text: LEIRAS OY;HUHTAMAEKI OY
2004-09-01	V1	Lapsed because of non-payment of the annual fee	Effective date: 20040701

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EP0474874B1 (de)	1995-10-18	Zusammensetzungen von Maillard-Reaktion inhibitoren
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US6358999B2 (en)	2002-03-19	Use of zinc tranexamate in the treatment of diabetes
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