LU85716A1 - Procede de preparation d'un nouveau compose complexe d'hemine ayant des applications medicales - Google Patents

Procede de preparation d'un nouveau compose complexe d'hemine ayant des applications medicales Download PDF

Info

Publication number: LU85716A1
Authority: LU; Luxembourg
Prior art keywords: hemin; water; arginine; preparation; arginate
Prior art date: 1984-12-12

Application number

LU85716A

Other languages

English (en)

French (fr)

Inventor

Grels Daniel Ingberg

Ritva Laila Aneri Penttilae

Reino Olavi Tokola

Raimo Antero Tenhunen

Original Assignee

Medica Pharma Co Ltd

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

1984-12-28

Publication date

1985-07-24

1984-12-28 Application filed by Medica Pharma Co Ltd filed Critical Medica Pharma Co Ltd

1985-07-24 Publication of LU85716A1 publication Critical patent/LU85716A1/fr

Links

238000000034 method Methods 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 8
230000008569 process Effects 0.000 title claims description 8
-1 HEMINE COMPOUND Chemical class 0.000 title claims description 6
229940025294 hemin Drugs 0.000 claims description 85
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 claims description 82
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 15
229930064664 L-arginine Natural products 0.000 claims description 15
235000014852 L-arginine Nutrition 0.000 claims description 15
241000097929 Porphyria Species 0.000 claims description 13
208000010642 Porphyrias Diseases 0.000 claims description 13
KDXKERNSBIXSRK-UHFFFAOYSA-M lysinate Chemical compound NCCCCC(N)C([O-])=O KDXKERNSBIXSRK-UHFFFAOYSA-M 0.000 claims description 12
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 11
239000000203 mixture Substances 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 9
239000007924 injection Substances 0.000 claims description 7
238000002347 injection Methods 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 7
208000007502 anemia Diseases 0.000 claims description 6
235000019766 L-Lysine Nutrition 0.000 claims description 5
239000004472 Lysine Substances 0.000 claims description 5
239000002775 capsule Substances 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
238000003756 stirring Methods 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 3
239000011877 solvent mixture Substances 0.000 claims description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 2
235000001014 amino acid Nutrition 0.000 claims description 2
150000001413 amino acids Chemical class 0.000 claims description 2
239000000843 powder Substances 0.000 claims description 2
239000002994 raw material Substances 0.000 claims 1
239000011780 sodium chloride Substances 0.000 claims 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 32
229910052742 iron Inorganic materials 0.000 description 16
230000015572 biosynthetic process Effects 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 11
239000000243 solution Substances 0.000 description 10
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
102000004020 Oxygenases Human genes 0.000 description 6
108090000417 Oxygenases Proteins 0.000 description 6
239000000047 product Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
102000001554 Hemoglobins Human genes 0.000 description 5
108010054147 Hemoglobins Proteins 0.000 description 5
206010022971 Iron Deficiencies Diseases 0.000 description 5
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 description 5
201000005060 thrombophlebitis Diseases 0.000 description 5
102000004190 Enzymes Human genes 0.000 description 4
108090000790 Enzymes Proteins 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
208000031162 sideroblastic anemia Diseases 0.000 description 4
239000000758 substrate Substances 0.000 description 4
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 3
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
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000008280 blood Substances 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
235000013305 food Nutrition 0.000 description 3
229940109738 hematin Drugs 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
238000004519 manufacturing process Methods 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
210000003462 vein Anatomy 0.000 description 3
239000004475 Arginine Substances 0.000 description 2
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
206010061218 Inflammation Diseases 0.000 description 2
150000008575 L-amino acids Chemical class 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
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
230000001154 acute effect Effects 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
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
230000007812 deficiency Effects 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
230000009088 enzymatic function Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
238000001990 intravenous administration 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
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
244000283070 Abies balsamea Species 0.000 description 1
235000007173 Abies balsamea Nutrition 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
108010017500 Biliverdin reductase Proteins 0.000 description 1
244000208235 Borassus flabellifer Species 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
239000005569 Iron sulphate Substances 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
238000009825 accumulation Methods 0.000 description 1
230000009471 action 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
239000007864 aqueous solution Substances 0.000 description 1
102000004558 biliverdin reductase Human genes 0.000 description 1
210000001185 bone marrow Anatomy 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
210000003743 erythrocyte Anatomy 0.000 description 1
230000029142 excretion Effects 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
239000012467 final product Substances 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
150000003278 haem Chemical class 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
210000004347 intestinal mucosa Anatomy 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
235000014571 nuts Nutrition 0.000 description 1
238000001139 pH measurement Methods 0.000 description 1
230000002093 peripheral effect Effects 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
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012088 reference solution Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000004550 soluble concentrate Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000013589 supplement Substances 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
150000003722 vitamin derivatives Chemical class 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)
Hematology (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Diabetes (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (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)

LU85716A 1984-12-12 1984-12-28 Procede de preparation d'un nouveau compose complexe d'hemine ayant des applications medicales LU85716A1 (fr)

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 (1)

Publication Number	Publication Date
LU85716A1 true LU85716A1 (fr)	1985-07-24

Family

ID=10571084

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU85716A LU85716A1 (fr)	1984-12-12	1984-12-28	Procede de preparation d'un nouveau compose complexe d'hemine ayant des applications medicales

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
ATA390784A (de)	1989-04-15
FR2574662B1 (fr)	1990-03-02
SE8406263L (sv)	1986-06-11
BE901319A (fr)	1985-04-16
CH666273A5 (de)	1988-07-15
CA1242713A (en)	1988-10-04
DE3446887A1 (de)	1986-07-03
NL192682C (nl)	1997-12-02
SU1384188A3 (ru)	1988-03-23
GB8431398D0 (en)	1985-01-23
SE8406263D0 (sv)	1984-12-10
FR2574662A1 (fr)	1986-06-20
AT389308B (de)	1989-11-27
DE3446887C2 (de)	1994-05-05
JPS61172821A (ja)	1986-08-04
NL8403782A (nl)	1986-07-01
SE457958B (sv)	1989-02-13
GB2168354B (en)	1988-12-07
GB2168354A (en)	1986-06-18
JPH0647541B2 (ja)	1994-06-22
NL192682B (nl)	1997-08-01

Publication	Publication Date	Title
EP0233106A1 (de)	1987-08-19	(-)-Benzhydrylsulfinylacetamid, Verfahren zur Herstellung und Verwendung in der Therapie
LU85716A1 (fr)	1985-07-24	Procede de preparation d'un nouveau compose complexe d'hemine ayant des applications medicales
FI68970C (fi)	1985-12-10	Foerfarande foer framstaellning av en ny medicinskt anvaendbarhemin-foerening
BE1001621A3 (fr)	1989-12-19	Nouveaux derives de l'acide furannuronique, leur preparation et leur utilisation comme medicaments.
FR2548187A1 (fr)	1985-01-04	Composes d'organo-germanium et leurs utilisations therapeutiques en tant qu'inhibiteurs des enzymes qui degradent les peptides opioides
EP0069674A1 (de)	1983-01-12	N-Acyl-L-aspactyl-taurine enthaltende Arzneimittel
WO1993014751A1 (fr)	1993-08-05	Compositions pharmaceutiques contenant comme principe actif des associations de vanadium et/ou de niobium avec des derives du pyrocatechol
CN109925279B (zh)	2021-07-06	一种硫辛酸注射液及其制备方法
WO2001036437A1 (fr)	2001-05-25	DERIVES DE β-D-5-THIOXYLOSE, PROCEDE DE PREPARATION ET UTILISATION EN THERAPEUTIQUE
CH675725A5 (de)	1990-10-31
FR2686511A1 (fr)	1993-07-30	Composition pharmaceutique contenant des associations de vanadium et/ou de niobium avec des acides amines ou des derives d'acides amines.
CS247187B2 (cs)	1986-12-18	Způsob výroby nového horninového komplexu
EP0126012B1 (de)	1988-01-13	Symmetrische Disulfide enthaltende pharmazeutische Zusammensetzungen
FR2546168A1 (fr)	1984-11-23	Dithiodiacetamides cycliques, procede pour leur preparation et compositions pharmaceutiques en contenant
CH670642A5 (de)	1989-06-30
JPH06321778A (ja)	1994-11-22	３−ヒドロキシ酪酸のオリゴマー及びその塩からなる輸液製剤
DK172797B1 (da)	1999-07-19	Fremgangsmåde til fremstilling af et fysiologisk virksomt, vandopløseligt hæminkompleks samt anvendelse af dette til fremst
FR2641465A1 (fr)	1990-07-13	Nouveau capteur de radicaux libres et les compositions pharmaceutiques en contenant
DD249028A5 (de)	1987-08-26	Verfahren zur herstellung einer neuen haemin-komplexverbindung mit medizinischer verwendbarkeit
FR2485372A1 (fr)	1981-12-31	Composition pharmaceutique pour le traitement des etats d'intoxication alcoolique aigue a base de 5-oxo-2-pyrrolidone carboxylate de pyridoxine et procede de preparation de ce dernier
EP0039265A1 (de)	1981-11-04	Biflavanon enthaltende Arzneimittel
WO2004043983A1 (fr)	2004-05-27	Derive du 4-methyl-2-oxo-2h-1-benzopyran-7yl 5-thio-beta-d-xylopyranoside, son procede de preparation et composition pharmaceutique le contenant
HK1013283A1 (en)	1999-08-20	Nitrato amino acid disulphides for use in the therapy of disorders of the cardiovasculary system
BE650426A (de)
EP0624092A1 (de)	1994-11-17	Verwendung von niobiumderivaten zur herstellung von arfneimitteln zur behandlung oder vorbehandlung von stoffwechselstörungen