KR920009767A - S(+)-페닐 알칸산 및 α-히드록시알칸산을 함유하는 착물 - Google Patents
S(+)-페닐 알칸산 및 α-히드록시알칸산을 함유하는 착물 Download PDFInfo
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- KR920009767A KR920009767A KR1019910020369A KR910020369A KR920009767A KR 920009767 A KR920009767 A KR 920009767A KR 1019910020369 A KR1019910020369 A KR 1019910020369A KR 910020369 A KR910020369 A KR 910020369A KR 920009767 A KR920009767 A KR 920009767A
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- 239000002253 acid Substances 0.000 title claims 23
- -1 (+)-phenyl Chemical group 0.000 title claims 12
- 239000013543 active substance Substances 0.000 claims 11
- 239000000243 solution Substances 0.000 claims 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 239000008196 pharmacological composition Substances 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 5
- HEFNNWSXXWATRW-JTQLQIEISA-N dexibuprofen Chemical compound CC(C)CC1=CC=C([C@H](C)C(O)=O)C=C1 HEFNNWSXXWATRW-JTQLQIEISA-N 0.000 claims 4
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 239000004305 biphenyl Substances 0.000 claims 3
- 239000011521 glass Substances 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 238000003756 stirring Methods 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 230000000202 analgesic effect Effects 0.000 claims 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims 2
- 230000000845 anti-microbial effect Effects 0.000 claims 2
- 230000001754 anti-pyretic effect Effects 0.000 claims 2
- 239000002221 antipyretic Substances 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 229960001680 ibuprofen Drugs 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 239000012223 aqueous fraction Substances 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- 230000036760 body temperature Effects 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 238000009792 diffusion process Methods 0.000 claims 1
- 230000008014 freezing Effects 0.000 claims 1
- 238000007710 freezing Methods 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- 239000012452 mother liquor Substances 0.000 claims 1
- 229960002009 naproxen Drugs 0.000 claims 1
- 230000003204 osmotic effect Effects 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 239000005518 polymer electrolyte Substances 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 239000002356 single layer Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/132—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing rings
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
- A61K9/146—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic macromolecular compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Communicable Diseases (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (15)
- 착물 결합이 R1-COOH···-OOC-R2 R1-COO-···HOC-R2(여기서, R1-COOH는 S(+)-페닐알칸산을, R2-COOH는 α-히드록시알칸산을 표시함)의 형태인 양성자 스윗치를 갖는 카르복실레이트-카르복실 상호작용에 기초하는 것이고 S(+)-페닐 알칸산의 카르복실기에 관계된 pKa 값이 3.5-3.9 범위이며, α-히드록시알칸산의 카르복실기에 관계된 pKa 값은 1.8-2.9범위에 드는 것을 특징으로 하는, 화학양론비 1 : 1의 S(+)-페닐알칸산과, α-히드록시알칸산으로 이루어진 수소다리-결합 착물.
- 제1항에 있어서, α-히드록시알칸산이 다음 일반식을 갖는 것이 특징인 착물 :상기식중 X=OH, Z=H, OH 또는 NH2A=탄소원자 1-10개를 함유하고, 필요시 아미노기 또는 1-6개의 히드록실기를 함유하는 알킬렌사슬 또는 결합임.
- 제1항 또는 2항에 있어서, α-히드록시알칸산의 카르복실기와 관편된 pKa 값이 1.9-2.5의 범위인 것이 특징인 착물.
- 전술한 항중 어느 한항에 있어서, 락트산의 에난티오머를 함유하는 것이 특징인 착물.
- 전술한 항중 어느 한항에 있어서, S(+)-페닐알칸산으로서 S(+)-이부프로펜 또는 S(+)-나프록센이 사용되는 것이 특징인 착물.
- 전술한 항중 어느 한항에 있어서, 착물이 S(+)-페닐알칸산, 바람직하게는S(+)-나프록센이 사용되는 것이 특징인 착물.
- a)수성매질(오직 물) 또는 pH범위가 5.5-7.5(20℃)인 약한 완충 수용액으로 부터의 제조를 위해, 예컨대 pHH 6.0-7.5(20℃)dml 0.01M-0.001M-K2HPO4/KH2PO4완충액을제조하고 여기에 동량의 S(+)-페닐 알칸산을 계속 저어주면서 첨가한 다음; b) 맑고 투명한 용액이 얻어진 때가지 (보통 20분후)상기 용액을 계속 교반하면서 40℃까지 가열하여 (수조) 모든 S(+)-페닐알칸산을 용액에 도입한 후; c)묽은 인산(H3PO4)를 첨가함으로써 용액의 pH를 pH 5.5-6.0으로 조정한 다음 (20℃) 동량의(상응하는) α-히드록시알칸산을 계속 교반하면서 도입하고; d)20분후 착물 생성물 완료하여 그로부터 0-4℃로 냉각한 다음 착물을 결정형태로 침전시켜 소결 유리 깔때기 또는 유리 필터(IG4)를 통해 모액으로 부터 분리하거나; e)d)단계 대신 워터 제트 진공중 회전 증발기(수조온도 25-30℃)내에서 맑은 용액을 절반 부피로 감소시켜, 무색(무정형)침전물을 생성시키고 이를 IG4 유리 필터를 통해 여과시켜 물/에탄올(70/30 V/V)이나 또는 에틸 아세테이트 (100%)로 부터 재결정시키는 단계로 됨을 특징으로 하는, 전술한 항중 어느 한항에 따른 착물의 제조방법.
- 진술한 항중 어느 한항에 따른 착물 한가지 이상과 생리적으로 허용되는 임의의 부가적인 부형제 또는 담체를 함유하는 약리적 조성물.
- 제8항에 있어서, 활성물질 착물이 S(+)-페닐 알칸산과 α-히드록시알칸산으로 구성됨을 특징으로 하는, 페닐 알칸산과 α-히드록시알칸산으로된 활성물질 착물과 생리적으로 허용되는 임의의 부가적인 보조물질을 함유하는, 항염, 해열, 항미생물 및 진통 효과를 갖는, 페닐 알칸산에 기초한 약리적 조성물.
- 제8항 도는 9항에 있어서, 활성물질 착물이 S(+)-이부프로펜이나 S(+)-나프록센 및 α-히드록시알칸산으로 구성되고, 조성물 중량의 0.1 내지 90% (w/w)을 차지함을 특징으로 하는, 이부프로펜이나 나프록센 및 α-히드록시알칸산과 생리적으로 허용되는 임의의 부가적인 보조물질을 함유하는, 항염, 해열, 항미생물 및 진통효과를 갖는, 이부프로펜이나 나트록센에 기초한 약리적 조성물.
- 제8항 내지 제10항중 어느 한 항에 있어서, S(+)-이부프로펜이나 S(+)-나프록센을 50내지 800mg, 바람직하게는 100내지 600mg, 더욱 바람직하게는 100내지 300mg 함유하는 것인 특징인 약리적 조성물.
- 제8항 내지 11항중 어느 한 항에 있어서, a)활성물질이 일분자 형태 이온으로서 담체에 용해되고, b)활성물질이 그의 본래 배치 및/또는 생물학적으로 활성인 키랄(에난티오머)배치로서 존재하며, c)활성물질의 물분율이 37℃에서 0.001 내지 0.67 이고, d)담체는 체온에서 용융되고, 상-균일 등방성이며, e)담체 및 활성물질로 구성된 등방성 용액이 실온에서 응고하며, f)응고된 용액은 결정성 또는 비결정성이고 활성물질을 결정형태로 함유하거나 또는 활성물질을 결정화시킬 수 있고, g)일분자층 또는 이온 용액이 삼투압 효과를 갖고 물 빙점을 저하시키며 h)폴리머 전해질내에 용해된 활성물질이 온도-의존성 확산계수 및 온도-의존성 비존도성을 갖는 등방성 용액임을 특징으로 하는 20-80℃ 범위에서 응고하고 수용성인, 폴리에틸렌 글리콜중 한가지 이상의 활성물질 착물과 수용성 담체로 이루어진 약리적 조성물.
- 제8항 내지 제12항중 어느 한항에 있어서, 경구 또는 비경구 투여에 적합한 투여에 적합한 투여량이 1일 S(+)-이부프로펜 50-1200mg, 보통 100-800mg, 바람직하게는 200-600mg 범위이고, 국소 투여시 적합한 투여량은 1일 10-200mg 범위인 것이 특징인 약리적 조성물.
- 전술한 항중 어느 한항에 있어서, S(+)-페닐 알칸산이 다음 일반식을 갖는 것이 특징은 착물.상기식중, R은 저급 알킬, Ar은 예컨대 페닐, 디페닐, 및 나프탈과 같이 방향족계내에 탄소원자를 12개까지 갖는 모토시클릭, 폴리시클릭 또는 오르토-축합된 폴리시클릭 방향족기이고 이 방향족기의 치환체에는 1개 이상의 할로겐 원자, C1-C4알킬, 벤질, 히드록시, C1-C2알콕시, 펜녹시 및 벤조일기가 포함됨.
- 제14항에 있어서, 치환 아릴이 4-이소부틸-페닐, 3-페녹시-페닐, 2-플루오로-4-디페닐, 4′-플루오로-4-디페닐, 6-메톡시-2-나프틸, 5-클로로-6-메톡시-2-나프틸 및 5-브로모-6-메톡시-나프틸, 4-클로로-페닐, 4-디플루오로-메톡시-페닐, 6-히드록시-2-나프틸, 및 5-브로모-6-히드록시-2-나프틸중에서 선택된 것이 특징인 착물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4036459 | 1990-11-15 | ||
DEP4036459.3 | 1990-11-15 |
Publications (1)
Publication Number | Publication Date |
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KR920009767A true KR920009767A (ko) | 1992-06-25 |
Family
ID=6418340
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019910020369A KR920009767A (ko) | 1990-11-15 | 1991-11-15 | S(+)-페닐 알칸산 및 α-히드록시알칸산을 함유하는 착물 |
Country Status (18)
Country | Link |
---|---|
US (1) | US5254728A (ko) |
EP (1) | EP0486964B1 (ko) |
JP (1) | JPH0656738A (ko) |
KR (1) | KR920009767A (ko) |
CN (1) | CN1061405A (ko) |
AT (1) | ATE137487T1 (ko) |
AU (1) | AU643168B2 (ko) |
BG (1) | BG95488A (ko) |
BR (1) | BR9104995A (ko) |
CA (1) | CA2055682A1 (ko) |
CS (1) | CS346691A3 (ko) |
DE (2) | DE59107762D1 (ko) |
ES (1) | ES2089091T3 (ko) |
HU (1) | HUT59653A (ko) |
MX (1) | MX9102087A (ko) |
NZ (1) | NZ240618A (ko) |
PL (1) | PL292414A1 (ko) |
ZA (1) | ZA919076B (ko) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HUT59692A (en) * | 1990-11-15 | 1992-06-29 | Puetter Medice Chem Pharm | Process for producing complexes containing s/+/-phenyl-alkanoic acids and aminosugars |
TW442287B (en) * | 1995-06-13 | 2001-06-23 | American Home Produits Corp | Organoleptically acceptable oral pharmaceutical composition comprising the S(+)1,8-diethyl-1-1,3,4,9-tetrahydropyrano[3,4-b] indole-1-acetic acid (Etodolac) |
JP4707201B2 (ja) * | 1997-02-04 | 2011-06-22 | 千寿製薬株式会社 | ピリドンカルボン酸の可溶化方法、その可溶化剤および可溶化されたピリドンカルボン酸からなる水性液剤 |
DE10003757A1 (de) * | 2000-01-28 | 2001-08-02 | Knoll Ag | Ibuprofen-Wirkstoffzubereitung |
US20100222311A1 (en) * | 2007-10-19 | 2010-09-02 | Purdue Research Foundation | Solid formulations of crystalline compounds |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IN166447B (ko) * | 1985-11-27 | 1990-05-12 | Ethicon Inc | |
DE3836863A1 (de) * | 1988-10-27 | 1990-05-03 | Klosa Josef | Fluessige, geloeste antirheumatische arzneizubereitungen |
DE69022678T2 (de) * | 1989-10-17 | 1996-03-21 | Merck & Co Inc | S(+)-Ibuprofen-L-Aminosäure und S(+)-Ibuprofen-D-Aminosäure als Analgetika mit grösserem pharmakologischem Potential. |
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 |
HUT59692A (en) * | 1990-11-15 | 1992-06-29 | Puetter Medice Chem Pharm | Process for producing complexes containing s/+/-phenyl-alkanoic acids and aminosugars |
-
1991
- 1991-11-14 HU HU913573A patent/HUT59653A/hu unknown
- 1991-11-15 BG BG095488A patent/BG95488A/bg unknown
- 1991-11-15 CA CA002055682A patent/CA2055682A1/en not_active Abandoned
- 1991-11-15 ZA ZA919076A patent/ZA919076B/xx unknown
- 1991-11-15 AU AU87909/91A patent/AU643168B2/en not_active Ceased
- 1991-11-15 NZ NZ240618A patent/NZ240618A/en unknown
- 1991-11-15 US US07/792,485 patent/US5254728A/en not_active Expired - Fee Related
- 1991-11-15 ES ES91119524T patent/ES2089091T3/es not_active Expired - Lifetime
- 1991-11-15 CN CN91110741A patent/CN1061405A/zh active Pending
- 1991-11-15 DE DE59107762T patent/DE59107762D1/de not_active Expired - Fee Related
- 1991-11-15 PL PL29241491A patent/PL292414A1/xx unknown
- 1991-11-15 EP EP91119524A patent/EP0486964B1/de not_active Expired - Lifetime
- 1991-11-15 MX MX9102087A patent/MX9102087A/es unknown
- 1991-11-15 CS CS913466A patent/CS346691A3/cs unknown
- 1991-11-15 AT AT91119524T patent/ATE137487T1/de not_active IP Right Cessation
- 1991-11-15 DE DE4137699A patent/DE4137699A1/de not_active Withdrawn
- 1991-11-15 KR KR1019910020369A patent/KR920009767A/ko not_active Application Discontinuation
- 1991-11-15 JP JP3354101A patent/JPH0656738A/ja active Pending
- 1991-11-18 BR BR919104995A patent/BR9104995A/pt not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
CA2055682A1 (en) | 1992-05-16 |
MX9102087A (es) | 1992-10-30 |
CN1061405A (zh) | 1992-05-27 |
US5254728A (en) | 1993-10-19 |
ZA919076B (en) | 1992-08-26 |
HU913573D0 (en) | 1992-01-28 |
DE59107762D1 (de) | 1996-06-05 |
AU643168B2 (en) | 1993-11-04 |
NZ240618A (en) | 1994-10-26 |
DE4137699A1 (de) | 1992-05-27 |
EP0486964B1 (de) | 1996-05-01 |
CS346691A3 (en) | 1992-06-17 |
BR9104995A (pt) | 1992-06-23 |
AU8790991A (en) | 1992-05-21 |
EP0486964A3 (en) | 1992-12-16 |
PL292414A1 (en) | 1992-10-19 |
EP0486964A2 (de) | 1992-05-27 |
ATE137487T1 (de) | 1996-05-15 |
JPH0656738A (ja) | 1994-03-01 |
BG95488A (bg) | 1993-12-24 |
ES2089091T3 (es) | 1996-10-01 |
HUT59653A (en) | 1992-06-29 |
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