DE69022678T2 - S(+)-Ibuprofen-L-Aminosäure und S(+)-Ibuprofen-D-Aminosäure als Analgetika mit grösserem pharmakologischem Potential. - Google Patents
S(+)-Ibuprofen-L-Aminosäure und S(+)-Ibuprofen-D-Aminosäure als Analgetika mit grösserem pharmakologischem Potential.Info
- Publication number
- DE69022678T2 DE69022678T2 DE69022678T DE69022678T DE69022678T2 DE 69022678 T2 DE69022678 T2 DE 69022678T2 DE 69022678 T DE69022678 T DE 69022678T DE 69022678 T DE69022678 T DE 69022678T DE 69022678 T2 DE69022678 T2 DE 69022678T2
- Authority
- DE
- Germany
- Prior art keywords
- ibuprofen
- amino acid
- lysine
- analgesics
- crystalline
- 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 - Fee Related
Links
- 229940035676 analgesics Drugs 0.000 title 1
- 239000000730 antalgic agent Substances 0.000 title 1
- 230000000144 pharmacologic effect Effects 0.000 title 1
- IHHXIUAEPKVVII-PTKYJSHISA-N [(5s)-5-amino-5-carboxypentyl]azanium;(2s)-2-[4-(2-methylpropyl)phenyl]propanoate Chemical compound NCCCC[C@H](N)C(O)=O.CC(C)CC1=CC=C([C@H](C)C(O)=O)C=C1 IHHXIUAEPKVVII-PTKYJSHISA-N 0.000 claims description 16
- 208000002193 Pain Diseases 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- IHHXIUAEPKVVII-APFIOPMWSA-N (2s)-2,6-diaminohexanoic acid;(2r)-2-[4-(2-methylpropyl)phenyl]propanoic acid Chemical class NCCCC[C@H](N)C(O)=O.CC(C)CC1=CC=C([C@@H](C)C(O)=O)C=C1 IHHXIUAEPKVVII-APFIOPMWSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 230000000202 analgesic effect Effects 0.000 abstract description 9
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 18
- 229960001680 ibuprofen Drugs 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 8
- HEFNNWSXXWATRW-JTQLQIEISA-N dexibuprofen Chemical compound CC(C)CC1=CC=C([C@H](C)C(O)=O)C=C1 HEFNNWSXXWATRW-JTQLQIEISA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000004472 Lysine Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- -1 flavorings Substances 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- 208000005171 Dysmenorrhea Diseases 0.000 description 2
- 206010013935 Dysmenorrhoea Diseases 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 235000019766 L-Lysine Nutrition 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-M lysinate Chemical class NCCCCC(N)C([O-])=O KDXKERNSBIXSRK-UHFFFAOYSA-M 0.000 description 2
- 235000018977 lysine Nutrition 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 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
- 150000008545 L-lysines Chemical class 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 208000004550 Postoperative Pain Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000003821 menstrual periods Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/08—Saturated compounds having a carboxyl group bound to a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/26—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one amino group bound to the carbon skeleton, e.g. lysine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (5)
1. Kristallines S(+)-Ibuprofen-L-lysin, das im wesentlichen frei von
irgendeinem anderen Ibuprofen-lysin-Stereoisomer ist.
2. Die Verbindung nach Anspruch 1, worin das Gewichtsverhältnis von
S(+)-Ibuprofen-L-lysin zu anderen Stereoisomeren wenigstens 95:5 ist.
3. Die Verbindung nach Anspruch 1, worin das Gewichtsverhältnis
wenigstens 99:1 ist.
4. Eine pharmazeutische Zusammensetzung, die eine wie in irgendeinem der
Ansprüche 1 bis 3 beanspruchte Verbindung und einen nicht toxischen,
pharmazeutisch annehmbaren Träger umfaßt.
5. Die Verwendung einer wie in irgendeinem der Ansprüche 1 bis 3
beanspruchten Verbindung für die Herstellung eines Medikaments zur
Schmerzund Endzündungsbehandlung bei einem Menschen.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US42246689A | 1989-10-17 | 1989-10-17 |
Publications (2)
Publication Number | Publication Date |
---|---|
DE69022678D1 DE69022678D1 (de) | 1995-11-02 |
DE69022678T2 true DE69022678T2 (de) | 1996-03-21 |
Family
ID=23675012
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE69022678T Expired - Fee Related DE69022678T2 (de) | 1989-10-17 | 1990-10-11 | S(+)-Ibuprofen-L-Aminosäure und S(+)-Ibuprofen-D-Aminosäure als Analgetika mit grösserem pharmakologischem Potential. |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP0424028B1 (de) |
JP (1) | JPH03206064A (de) |
KR (1) | KR910007858A (de) |
AT (1) | ATE128452T1 (de) |
AU (1) | AU635074B2 (de) |
CA (1) | CA2027624A1 (de) |
DE (1) | DE69022678T2 (de) |
DK (1) | DK0424028T3 (de) |
IE (1) | IE68508B1 (de) |
PT (1) | PT95564B (de) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HUT59656A (en) * | 1990-11-15 | 1992-06-29 | Puetter Medice Chem Pharm | Process for producing s/+/-phenyl-alkanoic acids and alpha-amino-acids containing complexes and pharmaceutical compositions containing them as active components |
HUT59653A (en) * | 1990-11-15 | 1992-06-29 | Puetter Medice Chem Pharm | Process for producing complexes containing s/+/-phenyl-alcanoic acids and alpha-hydroxy-alcanoic acids and pharmaceutical compositions containing them as active components |
US5552160A (en) * | 1991-01-25 | 1996-09-03 | Nanosystems L.L.C. | Surface modified NSAID nanoparticles |
GB9200114D0 (en) * | 1992-01-04 | 1992-02-26 | Scras | Dual inhibitors of no synthase and cyclooxygenase |
FR2687673B1 (fr) * | 1992-01-13 | 1995-07-07 | Jung Jean | Sels amines d'acides arylcarboxyliques, sterilisables, solubles dans l'eau, utilises en ophtalmologie et/ou dans la sphere otorhinolaryngologique. |
ATE151740T1 (de) * | 1992-12-02 | 1997-05-15 | Knoll Ag | Verfahren zur herstellung von im wesentlichen enantiomeren der phenylpropionsäuren |
IT1264856B1 (it) * | 1993-06-21 | 1996-10-17 | Zambon Spa | Composizione farmaceutica ad attivita' analgesica |
IT1264855B1 (it) * | 1993-06-21 | 1996-10-17 | Zambon Spa | Composizioni farmaceutiche contenenti sali dell'acido s(+)-2-(4-isobutilfenil) propionico con amminoacidi basici |
IT1266583B1 (it) * | 1993-07-30 | 1997-01-09 | Zambon Spa | Processo per la preparazione di sali dell'acido 2-(4-isobutilfenil)- propionico |
EP0740935A4 (de) * | 1994-02-24 | 1999-06-16 | Otsuka Pharma Co Ltd | Verstärker der analgetischen aktivität |
ES2105948B1 (es) * | 1994-10-31 | 1998-07-01 | Zambon Spa | Procedimiento para la preparacion de sales de acido 2-(4-isobutilfenil) propionico. |
US7914814B2 (en) | 1997-09-17 | 2011-03-29 | Strategic Science & Technologies, Llc | Topical delivery of arginine of cause beneficial effects |
AU737199B2 (en) * | 1997-09-17 | 2001-08-09 | Strategic Science & Technologies, Llc | A delivery of arginine to cause beneficial effects |
KR100523242B1 (ko) * | 2000-05-18 | 2005-10-24 | 한미약품 주식회사 | 이부프로펜을 함유하는 정제 조성물 |
ES2429443T3 (es) | 2004-04-19 | 2013-11-14 | Strategic Science & Technologies, Llc | Suministro transdérmico de sustancias beneficiosas efectuado mediante un entorno de fuerza iónica elevada |
US9226909B2 (en) | 2004-04-19 | 2016-01-05 | Strategic Science & Technologies, Llc | Beneficial effects of increasing local blood flow |
ES2303468B1 (es) * | 2007-01-22 | 2009-06-08 | Masterfarm, S.L | "una composicion farmaceutica pulverulenta que comprende ibuprofeno". |
US9072659B2 (en) | 2009-06-24 | 2015-07-07 | Strategic Science & Technologies, Llc | Topical composition containing naproxen |
US11684624B2 (en) | 2009-06-24 | 2023-06-27 | Strategic Science & Technologies, Llc | Treatment of erectile dysfunction and other indications |
KR101643797B1 (ko) | 2009-06-24 | 2016-07-28 | 스트러티직 사이언스 앤드 테크놀로지스, 엘엘씨 | 이부프로펜을 함유하는 국소 조성물 |
CN101978955A (zh) * | 2010-11-05 | 2011-02-23 | 航天中心医院 | 右旋布洛芬氨基酸盐片剂及其制备方法 |
JP2014504592A (ja) | 2010-12-29 | 2014-02-24 | ストラテジック サイエンス アンド テクノロジーズ, エルエルシー | 勃起不全および他の適応症の処置 |
JP2014501283A (ja) | 2010-12-29 | 2014-01-20 | ストラテジック サイエンス アンド テクノロジーズ, エルエルシー | アレルギーおよび他の適応症の処置のためのシステムおよび方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH377368A (de) * | 1960-04-07 | 1964-05-15 | Inventa Ag | Verfahren zur Reinigung von 1(+)-Lysin |
IT1059677B (it) * | 1974-03-22 | 1982-06-21 | Neopharmed Spa | Sale di lisina ad azione terapeutica |
DE3669103D1 (de) * | 1986-11-14 | 1990-04-05 | Puetter Medice Chem Pharm | Ibuprofen enthaltendes arzneimittel. |
US4851444A (en) * | 1987-07-10 | 1989-07-25 | Analgesic Associates | Onset-hastened/enhanced analgesia |
-
1990
- 1990-10-11 AT AT90311150T patent/ATE128452T1/de not_active IP Right Cessation
- 1990-10-11 DK DK90311150.8T patent/DK0424028T3/da active
- 1990-10-11 DE DE69022678T patent/DE69022678T2/de not_active Expired - Fee Related
- 1990-10-11 PT PT95564A patent/PT95564B/pt not_active IP Right Cessation
- 1990-10-11 EP EP90311150A patent/EP0424028B1/de not_active Expired - Lifetime
- 1990-10-15 CA CA002027624A patent/CA2027624A1/en not_active Abandoned
- 1990-10-16 AU AU64692/90A patent/AU635074B2/en not_active Ceased
- 1990-10-16 KR KR1019900016429A patent/KR910007858A/ko not_active Application Discontinuation
- 1990-10-16 IE IE371790A patent/IE68508B1/en not_active IP Right Cessation
- 1990-10-17 JP JP2276564A patent/JPH03206064A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
DK0424028T3 (da) | 1996-01-29 |
JPH03206064A (ja) | 1991-09-09 |
CA2027624A1 (en) | 1991-04-18 |
PT95564B (pt) | 1997-11-28 |
EP0424028B1 (de) | 1995-09-27 |
IE68508B1 (en) | 1996-06-26 |
AU6469290A (en) | 1991-04-26 |
EP0424028A3 (en) | 1992-06-10 |
IE903717A1 (en) | 1991-04-24 |
DE69022678D1 (de) | 1995-11-02 |
KR910007858A (ko) | 1991-05-30 |
AU635074B2 (en) | 1993-03-11 |
EP0424028A2 (de) | 1991-04-24 |
ATE128452T1 (de) | 1995-10-15 |
PT95564A (pt) | 1991-08-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE69022678T2 (de) | S(+)-Ibuprofen-L-Aminosäure und S(+)-Ibuprofen-D-Aminosäure als Analgetika mit grösserem pharmakologischem Potential. | |
DE69409969T2 (de) | Salze der mehrfach ungesättigten fettsäuren und diese enthaltende pharmazeutischen zusammensetzungen | |
DE69329400T2 (de) | L-Dopa Ester enthaltende Zusammensetzung | |
DE69414720T2 (de) | Kristallines, wasserfreies mofetilmycophenolat und zubereitungen zu deren intravenösen anwendung | |
DE3907649C2 (de) | Arzneimittel, geeignet bei der Bekämpfung von Viren und zur Immunstimulierung | |
DE3424781C2 (de) | Verwendung von L-Carnosin zur Tumorbehandlung | |
DE69202166T2 (de) | Verwendung von Tetrahydrothienopyridinderivate als Angiogenese-Inhibitoren. | |
DE2451161A1 (de) | Stabile prostaglandin-e-gruppen enthaltende arzneimittelzubereitung sowie verfahren zu deren herstellung | |
DE2900887A1 (de) | Verfahren zur gewinnung einer natuerlichen polarfraktion mit antipsoriatischer wirksamkeit | |
DE3907688C2 (de) | Salze von ungesättigten Fettsäuren mit Aminosäuren, Verfahren zu ihrer Herstellung sowie die Verwendung der ersteren und von weiteren derartigen Salzen | |
DE3854121T2 (de) | Arzneimittelzusammensetzungen zur behandlung von psoriasis. | |
EP1154766B1 (de) | Verwendung von r-arylpropionsäuren zur herstellung von arzneimitteln, zur behandlung von erkrankungen bei mensch und tier, welche durch die hemmung der aktivierung von nf-kappa b therapeutisch beeinflusst werden können | |
DE2353797A1 (de) | Stabilisierung von prostaglandinen | |
DE69307895T2 (de) | Therapeutische verwendung von phosphoryl-l-serin-n-acyl-sphingosin | |
DE3538619A1 (de) | Arzneimittel, die isomere des hydroxyprolin enthalten | |
DE69023939T2 (de) | Förderung der Osteogenese durch Verwendung von Vitamin D-Derivaten. | |
CH647677A5 (de) | 4'-(acridinylamino)-methansulfon-anisidid enthaltende pharmazeutische zusammensetzung. | |
CH624098A5 (de) | ||
EP0493662A1 (de) | Verwendung von Superoxiddismutasen für die Herstellung von Arzneimitteln zur Prophylaxe und/oder Behandlung von Organversagen bei Risikopatienten mit Polytrauma als Unfallfolge | |
DE3873210T2 (de) | Verwendung von benzylpyridin-derivaten zur herstellung eines arzneimittels zur behandlung der demenz. | |
EP0223850B1 (de) | Arzneimittel, die derivate des prolin oder hydroxyprolin enthalten | |
DE2633891C2 (de) | Tris-(hydroxymethyl)-aminomethansalz der 2-(5-Benzoylthienyl)-α-methylessigsäure, Verfahren zu dessen Herstellung und dieses enthaltende pharmazeutische Zusammensetzungen | |
DE2131679A1 (de) | 3,4,5-Trimethoxybenzamidocarbonsaeure und ihre Salze sowie Arzneipraeparate | |
DE2318784A1 (de) | N-(2,4-dihydroxybenzoyl)-4-aminosalizylsaeure | |
DE2605243A1 (de) | Pyrazolessigsaeurehaltiges arzneimittel |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
8364 | No opposition during term of opposition | ||
8339 | Ceased/non-payment of the annual fee |