NO317304B1 - Tetrahydropyridoetere - Google Patents
Tetrahydropyridoetere Download PDFInfo
- Publication number
- NO317304B1 NO317304B1 NO20011243A NO20011243A NO317304B1 NO 317304 B1 NO317304 B1 NO 317304B1 NO 20011243 A NO20011243 A NO 20011243A NO 20011243 A NO20011243 A NO 20011243A NO 317304 B1 NO317304 B1 NO 317304B1
- Authority
- NO
- Norway
- Prior art keywords
- hydroxy
- dimethyl
- phenyl
- methoxyethoxy
- naphthyridine
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 93
- PWILYDZRJORZDR-MISYRCLQSA-N (7r,8r,9r)-7-(2-methoxyethoxy)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCCOC)=CC=CC=C1 PWILYDZRJORZDR-MISYRCLQSA-N 0.000 claims abstract 3
- -1 hydroxy, methoxy, ethoxy, isopropoxy, methoxyethoxy Chemical group 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 239000003814 drug Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 229940079593 drug Drugs 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- PFUDJBXGGYVENA-BHIYHBOVSA-N (7r,8r,9r)-7,8-dimethoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine Chemical compound C1([C@@H]2[C@H]([C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)OC)=CC=CC=C1 PFUDJBXGGYVENA-BHIYHBOVSA-N 0.000 claims 1
- RJASEHFHFJEXPR-BHIYHBOVSA-N (7r,8r,9r)-7-ethoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCC)=CC=CC=C1 RJASEHFHFJEXPR-BHIYHBOVSA-N 0.000 claims 1
- GDQBYAHOQAFREY-RYQLBKOJSA-N (7r,8s,9s)-7-methoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@H]2[C@H](O)[C@@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)=CC=CC=C1 GDQBYAHOQAFREY-RYQLBKOJSA-N 0.000 claims 1
- LHJMQBVQSCNUMD-RLLQIKCJSA-N (7s,8r,9r)-2,3-dimethyl-9-phenyl-7-propan-2-yloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC(C)C)=CC=CC=C1 LHJMQBVQSCNUMD-RLLQIKCJSA-N 0.000 claims 1
- RJASEHFHFJEXPR-QRQLOZEOSA-N (7s,8r,9r)-7-ethoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OCC)=CC=CC=C1 RJASEHFHFJEXPR-QRQLOZEOSA-N 0.000 claims 1
- GDQBYAHOQAFREY-NXHRZFHOSA-N (7s,8r,9r)-7-methoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@@H]2[C@@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)=CC=CC=C1 GDQBYAHOQAFREY-NXHRZFHOSA-N 0.000 claims 1
- GDQBYAHOQAFREY-SZMVWBNQSA-N (7s,8s,9s)-7-methoxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-8-ol Chemical compound C1([C@H]2[C@H](O)[C@H](C3=C(C4=NC(C)=C(C)N4C=C3)N2)OC)=CC=CC=C1 GDQBYAHOQAFREY-SZMVWBNQSA-N 0.000 claims 1
- 230000028327 secretion Effects 0.000 abstract description 2
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
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- 239000000243 solution Substances 0.000 description 16
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
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- 238000006243 chemical reaction Methods 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- FHHGNULEXOWEKU-DJIMGWMZSA-N (7r,8r,9r)-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine-7,8-diol Chemical compound C1([C@H]2NC=3C4=NC(=C(N4C=CC=3[C@@H](O)[C@@H]2O)C)C)=CC=CC=C1 FHHGNULEXOWEKU-DJIMGWMZSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000010413 mother solution Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- MXBVNILGVJVVMH-UHFFFAOYSA-N 1,7-naphthyridine Chemical compound C1=NC=CC2=CC=CN=C21 MXBVNILGVJVVMH-UHFFFAOYSA-N 0.000 description 4
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 4
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- 210000002784 stomach Anatomy 0.000 description 4
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- 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 3
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- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 3
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (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)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843504 | 1998-09-23 | ||
| EP98117988 | 1998-09-23 | ||
| PCT/EP1999/006899 WO2000017200A1 (en) | 1998-09-23 | 1999-09-17 | Tetrahydropyridoethers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20011243D0 NO20011243D0 (no) | 2001-03-12 |
| NO20011243L NO20011243L (no) | 2001-03-12 |
| NO317304B1 true NO317304B1 (no) | 2004-10-04 |
Family
ID=26049024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20011243A NO317304B1 (no) | 1998-09-23 | 2001-03-12 | Tetrahydropyridoetere |
Country Status (31)
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CZ292335B6 (cs) | 1998-09-23 | 2003-09-17 | Altana Pharma Ag | Tetrahydropyridoethery, jejich použití a farmaceutický prostředek |
| US6503923B1 (en) | 1999-04-17 | 2003-01-07 | Altana Pharma Ag | Haloalkoxy imidazonaphthyridines |
| CA2285516C (en) * | 1999-05-12 | 2010-12-07 | President And Fellows Of Harvard College | Dopamine transporter imaging agents |
| MXPA02009549A (es) * | 2000-03-29 | 2004-05-14 | Altana Pharma Ag | Imidazopiridinas triciclicas. |
| ATE311389T1 (de) * | 2000-03-29 | 2005-12-15 | Altana Pharma Ag | Wirkstoffvorläufer von imidazopyridin-derivaten |
| CN1692113A (zh) * | 2000-10-25 | 2005-11-02 | 奥坦纳医药公司 | 作为胃分泌抑制剂的多取代咪唑并吡啶 |
| UA80393C2 (uk) | 2000-12-07 | 2007-09-25 | Алтана Фарма Аг | Фармацевтична композиція, яка містить інгібітор фде 4, диспергований в матриці |
| WO2002069968A1 (en) * | 2001-03-08 | 2002-09-12 | Astrazeneca Ab | New use |
| EP1414821B1 (en) | 2001-08-02 | 2006-08-16 | ALTANA Pharma AG | Tricyclic epoxides |
| CN1656096A (zh) * | 2001-08-03 | 2005-08-17 | 奥坦纳医药公司 | 用于治疗胃肠病症的烷基－取代的咪唑吡啶 |
| WO2003014120A1 (en) * | 2001-08-03 | 2003-02-20 | Altana Pharma Ag | Amino-substituted imidazopyridines for the treatment of gastrointestinal diseases |
| EP1476445A1 (en) | 2002-02-15 | 2004-11-17 | ALTANA Pharma AG | Tricyclic n-acyl compounds |
| MY140561A (en) | 2002-02-20 | 2009-12-31 | Nycomed Gmbh | Dosage form containing pde 4 inhibitor as active ingredient |
| AU2003227710A1 (en) * | 2002-05-07 | 2003-11-11 | Altana Pharma Ag | New combination of reversible proton pump inhibitors and airway therapeutics for treating airway disorders |
| MXPA05005117A (es) | 2002-11-19 | 2005-07-01 | Altana Pharma Ag | Imidazopiridinas 8-sustituidas. |
| US7879833B2 (en) | 2002-12-12 | 2011-02-01 | Nycomed Gmbh | Combination medicament |
| KR20050088176A (ko) * | 2002-12-20 | 2005-09-02 | 알타나 파마 아게 | 8-트리알킬실록시-2-메틸-9-페닐-7-옥소-7,8,9,10-테트라히드로이미다조[1,2-ｈ][1,7]나프티리딘 |
| EP1599175A2 (en) * | 2003-02-17 | 2005-11-30 | ALTANA Pharma AG | Imidazopyridines containing combinations and their use in treating gastrointestinal inflammatory disorders |
| MXPA04008070A (es) | 2003-03-10 | 2004-11-26 | Altana Pharma Ag | Novedoso proceso para la preparacion de roflumilasto. |
| TW200503783A (en) * | 2003-04-11 | 2005-02-01 | Altana Pharma Ag | Oral pharmaceutical preparation for proton pump antagonists |
| SA04250092B1 (ar) * | 2003-05-14 | 2008-05-04 | التانا فاروا ايه جي | مركب وسيط جديد لتحضير مركبات إيميدازوبيريدين imidazopyridines فعالة علاجياً |
| WO2004105795A1 (en) * | 2003-05-27 | 2004-12-09 | Altana Pharma Ag | Pharmaceutical combinations of a proton pump inhibitor and a compound which modifies gastrointestinal motility |
| AU2004268641A1 (en) * | 2003-08-29 | 2005-03-10 | Dynogen Pharmaceuticals, Inc. | Compositions useful for treating gastrointestinal motility disorders |
| ES2452691T5 (es) | 2003-09-16 | 2022-09-14 | Covis Pharma Gmbh | Uso de ciclesonida para el tratamiento de enfermedades respiratorias |
| EP1974730A1 (en) | 2003-11-03 | 2008-10-01 | AstraZeneca AB | Imidazo[1,2-a]pyridine derivatives for use in the treatment of sleep disturbance due to silent gastro-esophageal reflux |
| AU2004298453A1 (en) | 2003-12-19 | 2005-06-30 | Altana Pharma Ag | Intermediates for the preparation of tricyclic dihydropyrano -imidazo -pyridines derivatives |
| NZ549011A (en) * | 2004-02-17 | 2009-04-30 | Altana Pharma Ag | Tricyclic imidazopyridines and intermediates for the synthesis thereof |
| PL1784404T3 (pl) | 2004-09-03 | 2012-04-30 | Yuhan Corp | Pochodne pirolo[2,3-c]pirydyny i sposoby ich wytwarzania |
| EP1784403B1 (en) | 2004-09-03 | 2013-07-17 | Yuhan Corporation | Pyrrolo[3,2-b]pyridine derivatives and processes for the preparation thereof |
| US8148529B2 (en) | 2004-09-03 | 2012-04-03 | Yuhan Corporation | Pyrrolo[3,2-C] pyridine derivatives and processes for the preparation thereof |
| JP5383183B2 (ja) * | 2005-03-16 | 2014-01-08 | タケダ ゲゼルシャフト ミット ベシュレンクテル ハフツング | ロフルミラストを含有する矯味された剤形 |
| EP2080513A1 (en) | 2008-01-16 | 2009-07-22 | Schraermeyer, Ulrich, Prof. Dr. rer. nat | Tetrahydropyridoethers for treatment of AMD |
| WO2011004882A1 (ja) * | 2009-07-09 | 2011-01-13 | ラクオリア創薬株式会社 | 消化管運動異常が関与する疾患を治療するためのアシッドポンプ拮抗剤 |
| WO2012027240A1 (en) * | 2010-08-23 | 2012-03-01 | Schering Corporation | Fused tricyclic inhibitors of mammalian target of rapamycin |
| KR101699145B1 (ko) * | 2012-06-15 | 2017-02-03 | (주)바이오팜솔루션즈 | 페닐알킬설파메이트 화합물 및 이를 포함하는 근육 이완제 조성물 |
| EP3054949A1 (en) | 2013-10-08 | 2016-08-17 | Katairo GmbH | Tetrahydropyridoethers for the treatment of stargardt's disease |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4468400A (en) * | 1982-12-20 | 1984-08-28 | Schering Corporation | Antiulcer tricyclic imidazo [1,2-a]pyridines |
| DE3855692D1 (de) | 1987-07-16 | 1997-01-16 | Byk Gulden Lomberg Chem Fab | Imidazo[1,2-a]pyridine |
| SE9401197D0 (sv) * | 1994-04-11 | 1994-04-11 | Astra Ab | Active compounds |
| AU702166B2 (en) * | 1994-07-28 | 1999-02-18 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Acylimidazopyridines |
| WO1998042707A1 (en) * | 1997-03-24 | 1998-10-01 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Tetrahydropyrido compounds |
| CU23088A3 (es) * | 1997-03-24 | 2005-10-19 | Altana Pharma Ag | Compuestos de tetra-hidropiridina. |
| CZ292335B6 (cs) | 1998-09-23 | 2003-09-17 | Altana Pharma Ag | Tetrahydropyridoethery, jejich použití a farmaceutický prostředek |
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1999
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- 1999-09-17 CN CNB998112992A patent/CN1155598C/zh not_active Expired - Fee Related
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