EP0771202A1 - VERWENDUNG VON (S)-ADENOSYL-L-METHIONIN (SAMe) UND DESSEN PHYSIOLOGISCH VERTRÄGLICHEN SALZEN ZUR BEHANDLUNG VON REPERFUSIONSSCHÄDEN, DIE DURCH TEMPORÄRE FOKALE ISCHÄMIE AUSGELÖST WERDEN - Google Patents
VERWENDUNG VON (S)-ADENOSYL-L-METHIONIN (SAMe) UND DESSEN PHYSIOLOGISCH VERTRÄGLICHEN SALZEN ZUR BEHANDLUNG VON REPERFUSIONSSCHÄDEN, DIE DURCH TEMPORÄRE FOKALE ISCHÄMIE AUSGELÖST WERDENInfo
- Publication number
- EP0771202A1 EP0771202A1 EP95924974A EP95924974A EP0771202A1 EP 0771202 A1 EP0771202 A1 EP 0771202A1 EP 95924974 A EP95924974 A EP 95924974A EP 95924974 A EP95924974 A EP 95924974A EP 0771202 A1 EP0771202 A1 EP 0771202A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- same
- methionine
- reperfusion damage
- adenosyl
- physiologically compatible
- 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.)
- Withdrawn
Links
- 206010063837 Reperfusion injury Diseases 0.000 title claims abstract description 13
- 208000028867 ischemia Diseases 0.000 title claims abstract description 13
- 150000003839 salts Chemical class 0.000 title claims abstract description 9
- 230000001960 triggered effect Effects 0.000 title claims abstract description 5
- 229960004452 methionine Drugs 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 2
- 206010008118 cerebral infarction Diseases 0.000 description 7
- 230000010410 reperfusion Effects 0.000 description 5
- 210000004556 brain Anatomy 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 201000006474 Brain Ischemia Diseases 0.000 description 3
- 206010008120 Cerebral ischaemia Diseases 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002253 anti-ischaemic effect Effects 0.000 description 2
- 230000036770 blood supply Effects 0.000 description 2
- 208000026106 cerebrovascular disease Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000902 placebo Substances 0.000 description 2
- 229940068196 placebo Drugs 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- PKDBCJSWQUOKDO-UHFFFAOYSA-M 2,3,5-triphenyltetrazolium chloride Chemical compound [Cl-].C1=CC=CC=C1C(N=[N+]1C=2C=CC=CC=2)=NN1C1=CC=CC=C1 PKDBCJSWQUOKDO-UHFFFAOYSA-M 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 108010023197 Streptokinase Proteins 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 108050006955 Tissue-type plasminogen activator Proteins 0.000 description 1
- 208000032109 Transient ischaemic attack Diseases 0.000 description 1
- 108090000435 Urokinase-type plasminogen activator Proteins 0.000 description 1
- 102000003990 Urokinase-type plasminogen activator Human genes 0.000 description 1
- 206010053648 Vascular occlusion Diseases 0.000 description 1
- 206010047163 Vasospasm Diseases 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 230000003851 biochemical process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 201000008247 brain infarction Diseases 0.000 description 1
- FUDAIDRKVVTJFF-UHFFFAOYSA-N butane-1,1-disulfonic acid Chemical compound CCCC(S(O)(=O)=O)S(O)(=O)=O FUDAIDRKVVTJFF-UHFFFAOYSA-N 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 description 1
- 229960003132 halothane Drugs 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 238000007917 intracranial administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 208000023589 ischemic disease Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229960005202 streptokinase Drugs 0.000 description 1
- 238000011477 surgical intervention Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000009424 thromboembolic effect Effects 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 201000010875 transient cerebral ischemia Diseases 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
- 208000021331 vascular occlusion disease Diseases 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7076—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Definitions
- SAMe -Adenosyl-L-methionine
- SAMe can be used for various indications relating to central damage.
- the main manifestations of temporary focal ischemia are the following: (1) acute thromboembolic ischemia, where reperfusion by administration of thrombolytically active substances (such as urokinase, streptokinase or t-PA) or by surgery Measures are initiated, (2) vasospasms that dissolve spontaneously or after administration of vasodilatory substances, (3) surgical interventions, in which the temporary occlusion of an artery is initiated for operational reasons, and (4) transient ischemic attacks with unexplained
- the present invention relates to the use of SAMe and its physiologically tolerable salts for the treatment of reperfusion damage which is triggered by temporary focal ischemia.
- SAMe is preferably used in the form of a salt with a physiologically acceptable acid.
- Preferred acids are: hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, citric acid, tartaric acid, methanesulfonic acid, p-toluenesulfonic acid and butanedisulfonic acid.
- SAMe or its salts are administered for these indications in an amount of 10 to 1000 mg / kg body weight.
- SAMe can be administered parenterally (intravenously, intraarterially or intramuscularly) in a customary manner, with intravenous infusion being the preferred form of administration.
- the above amount is usually infused into the patient once over a period of 1 to 24 hours.
- SAMe can be applied in the usual galeni Customer application forms liquid, z. B. as a solution.
- the application forms normally contain the active ingredient in an amount of 1 to 50%, preferably 5 to 20%.
- the effect of SAMe on the size of the cerebral infarction caused by temporary focal cerebral ischemia was determined in the rat using the modified method of Chen et al. (Stroke 17: 738, 1986). For this, the right-sided A. cerebri media and the two Aa. carotis sess under halothane anesthesia exposed and occluded for 90 min. The size of the cerebral infarction was determined 24 hours later after staining with triphenyltetrazolium chloride.
- test animals were treated with 40 mg / kg + 100 mg / kg / h SAMe intravenously.
- the bolus was given either at the end of the 90-minute occlusion or 30 minutes later; the continuous infusion was maintained for 6 hours.
- Table 1 the temporary vascular occlusion resulted in significantly smaller cerebral infarcts when treated with SAMe than when treated with placebo (0.9% NaCl solution).
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Cardiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4425280 | 1994-07-16 | ||
| DE4425280A DE4425280C2 (de) | 1994-07-16 | 1994-07-16 | Verwendung von (S)-Adenosyl-L-methionin und dessen physiologisch verträglichen Salzen zur Behandlung von Reperfusionsschäden, die nach temporärer fokaler Ischämie ausgelöst werden |
| PCT/EP1995/002598 WO1996002252A1 (de) | 1994-07-16 | 1995-07-05 | VERWENDUNG VON (S)-ADENOSYL-L-METHIONIN (SAMe) UND DESSEN PHYSIOLOGISCH VERTRÄGLICHEN SALZEN ZUR BEHANDLUNG VON REPERFUSIONSSCHÄDEN, DIE DURCH TEMPORÄRE FOKALE ISCHÄMIE AUSGELÖST WERDEN |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0771202A1 true EP0771202A1 (de) | 1997-05-07 |
Family
ID=6523426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP95924974A Withdrawn EP0771202A1 (de) | 1994-07-16 | 1995-07-05 | VERWENDUNG VON (S)-ADENOSYL-L-METHIONIN (SAMe) UND DESSEN PHYSIOLOGISCH VERTRÄGLICHEN SALZEN ZUR BEHANDLUNG VON REPERFUSIONSSCHÄDEN, DIE DURCH TEMPORÄRE FOKALE ISCHÄMIE AUSGELÖST WERDEN |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5776911A (no) |
| EP (1) | EP0771202A1 (no) |
| JP (1) | JPH10502652A (no) |
| KR (1) | KR970704442A (no) |
| AU (1) | AU2927195A (no) |
| BG (1) | BG101145A (no) |
| CA (1) | CA2195345A1 (no) |
| CZ (1) | CZ12297A3 (no) |
| DE (1) | DE4425280C2 (no) |
| FI (1) | FI970165A (no) |
| HR (1) | HRP950405A2 (no) |
| HU (1) | HUT76834A (no) |
| IL (1) | IL114540A0 (no) |
| NO (1) | NO970185L (no) |
| PL (1) | PL318318A1 (no) |
| SI (1) | SI9520087A (no) |
| WO (1) | WO1996002252A1 (no) |
| ZA (1) | ZA955865B (no) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19515275A1 (de) * | 1995-04-26 | 1996-10-31 | Knoll Ag | Neue Verwendung von (S)-Adenosyl-L-methionin(SAMe) |
| IT1317920B1 (it) * | 2000-10-20 | 2003-07-15 | Univ Roma | S-adenosilmetionina e suoi derivati per il trattamento e laprevenzione della malattia di alzheimer. |
| US8841344B2 (en) | 2002-10-03 | 2014-09-23 | Hill's Pet Nutrition, Inc. | Method of using omega-3 fatty acids |
| FR2884421B1 (fr) | 2005-04-15 | 2007-08-10 | Virbac Sa | Nouveaux moyens de regulation des troubles du comportement chez les animaux de compagnie |
| EP1874937A2 (en) * | 2005-04-20 | 2008-01-09 | BASF Plant Science GmbH | Expression cassettes for seed-preferential expression in plants |
| CA2718469C (en) | 2008-03-17 | 2017-07-04 | National Research Council Of Canada | Aromatic prenyltransferase from hop |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1173990B (it) * | 1984-05-16 | 1987-06-24 | Bioresearch Spa | Sali stabili della solfo-adenosil-l-metionina (same) particolarmente adatti per uso parenterale |
| JPH0770235B2 (ja) * | 1988-06-24 | 1995-07-31 | 株式会社東芝 | 不揮発性メモリ回路装置 |
| JPH02290896A (ja) * | 1989-04-28 | 1990-11-30 | Fuji Kagaku Kogyo Kk | 新規なｓ―アデノシルメチオニン誘導体 |
-
1994
- 1994-07-16 DE DE4425280A patent/DE4425280C2/de not_active Expired - Fee Related
-
1995
- 1995-07-05 SI SI9520087A patent/SI9520087A/sl unknown
- 1995-07-05 JP JP8504640A patent/JPH10502652A/ja active Pending
- 1995-07-05 US US08/776,006 patent/US5776911A/en not_active Expired - Lifetime
- 1995-07-05 AU AU29271/95A patent/AU2927195A/en not_active Abandoned
- 1995-07-05 EP EP95924974A patent/EP0771202A1/de not_active Withdrawn
- 1995-07-05 PL PL95318318A patent/PL318318A1/xx unknown
- 1995-07-05 CZ CZ97122A patent/CZ12297A3/cs unknown
- 1995-07-05 KR KR1019970700288A patent/KR970704442A/ko not_active Application Discontinuation
- 1995-07-05 CA CA002195345A patent/CA2195345A1/en not_active Abandoned
- 1995-07-05 HU HU9700130A patent/HUT76834A/hu unknown
- 1995-07-05 WO PCT/EP1995/002598 patent/WO1996002252A1/de not_active Application Discontinuation
- 1995-07-11 IL IL11454095A patent/IL114540A0/xx unknown
- 1995-07-14 ZA ZA955865A patent/ZA955865B/xx unknown
- 1995-07-14 HR HRP4425280.3A patent/HRP950405A2/hr not_active Application Discontinuation
-
1997
- 1997-01-15 FI FI970165A patent/FI970165A/fi not_active Application Discontinuation
- 1997-01-15 NO NO970185A patent/NO970185L/no unknown
- 1997-01-17 BG BG101145A patent/BG101145A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9602252A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| KR970704442A (ko) | 1997-09-06 |
| PL318318A1 (en) | 1997-06-09 |
| US5776911A (en) | 1998-07-07 |
| DE4425280A1 (de) | 1996-01-18 |
| NO970185D0 (no) | 1997-01-15 |
| BG101145A (en) | 1997-08-29 |
| CA2195345A1 (en) | 1996-02-01 |
| ZA955865B (en) | 1997-01-14 |
| HU9700130D0 (en) | 1997-02-28 |
| FI970165A0 (fi) | 1997-01-15 |
| HRP950405A2 (en) | 1997-10-31 |
| FI970165A (fi) | 1997-03-14 |
| JPH10502652A (ja) | 1998-03-10 |
| MX9700439A (es) | 1998-05-31 |
| WO1996002252A1 (de) | 1996-02-01 |
| IL114540A0 (en) | 1995-11-27 |
| CZ12297A3 (cs) | 1998-04-15 |
| HUT76834A (en) | 1997-11-28 |
| NO970185L (no) | 1997-03-12 |
| SI9520087A (en) | 1997-08-31 |
| AU2927195A (en) | 1996-02-16 |
| DE4425280C2 (de) | 1997-05-07 |
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| 18W | Application withdrawn |
Withdrawal date: 19980617 |