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
-
- 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98117988 | 1998-09-23 | ||
| DE19843504 | 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)
| Country | Link |
|---|---|
| US (4) | US6436953B1 (zh) |
| EP (1) | EP1115725B1 (zh) |
| JP (1) | JP4145492B2 (zh) |
| KR (1) | KR100668400B1 (zh) |
| CN (2) | CN1155598C (zh) |
| AT (1) | ATE231862T1 (zh) |
| AU (1) | AU763463B2 (zh) |
| BG (1) | BG65195B1 (zh) |
| BR (1) | BR9914044A (zh) |
| CA (1) | CA2344251A1 (zh) |
| CZ (1) | CZ292335B6 (zh) |
| DE (1) | DE69905178T2 (zh) |
| DK (1) | DK1115725T3 (zh) |
| EA (1) | EA005377B1 (zh) |
| EE (1) | EE04677B1 (zh) |
| ES (1) | ES2191464T3 (zh) |
| GE (1) | GEP20032926B (zh) |
| HK (1) | HK1038360B (zh) |
| HR (1) | HRP20010224A2 (zh) |
| HU (1) | HUP0102990A3 (zh) |
| ID (1) | ID28896A (zh) |
| IL (2) | IL142063A0 (zh) |
| NO (1) | NO317304B1 (zh) |
| NZ (1) | NZ510610A (zh) |
| PL (1) | PL193616B1 (zh) |
| PT (1) | PT1115725E (zh) |
| RS (1) | RS50145B (zh) |
| SI (1) | SI1115725T1 (zh) |
| SK (1) | SK285165B6 (zh) |
| TR (1) | TR200100805T2 (zh) |
| WO (1) | WO2000017200A1 (zh) |
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| CZ292335B6 (cs) * | 1998-09-23 | 2003-09-17 | Altana Pharma Ag | Tetrahydropyridoethery, jejich použití a farmaceutický prostředek |
| DE60002855T2 (de) * | 1999-04-17 | 2004-05-06 | Altana Pharma Ag | Haloalkoxy-imidazonaphthyridine |
| CA2285516C (en) * | 1999-05-12 | 2010-12-07 | President And Fellows Of Harvard College | Dopamine transporter imaging agents |
| CA2404477A1 (en) * | 2000-03-29 | 2001-10-04 | Altana Pharma Ag | Tricyclic imidazopyridines |
| MXPA02009551A (es) * | 2000-03-29 | 2004-05-14 | Altana Pharma Ag | Profarmacos de derivados de imidazopiridina. |
| 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 |
| MXPA03007888A (es) * | 2001-03-08 | 2003-12-04 | Astrazeneca Ab | Compuestos para tratamiento y prevencion de ulcera gastrica inducida por medicamentos. |
| US6927292B2 (en) | 2001-08-02 | 2005-08-09 | Altana Pharma Ag | Tricyclic epoxides |
| EP1417208A1 (en) * | 2001-08-03 | 2004-05-12 | ALTANA Pharma AG | Amino-substituted imidazopyridines for the treatment of gastrointestinal diseases |
| CA2452801A1 (en) * | 2001-08-03 | 2003-02-27 | Altana Pharma Ag | Alkyl-substituted imidazopyridines for the treatment of gastrointestinal disorders |
| KR20040081204A (ko) | 2002-02-15 | 2004-09-20 | 알타나 파마 아게 | 트리시클릭 ｎ-아실 화합물 |
| 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 |
| NZ540504A (en) | 2002-11-19 | 2007-12-21 | Altana Pharma Ag | 8-Substituted imidazopyridines for the treatment of gastrointestinal disorders |
| JP4755495B2 (ja) | 2002-12-12 | 2011-08-24 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | 組合せ医薬品 |
| BR0316752A (pt) * | 2002-12-20 | 2005-10-25 | Altana Pharma Ag | Silil éteres |
| CA2515676A1 (en) * | 2003-02-17 | 2004-08-26 | Altana Pharma Ag | Imidazopyridines containing combinations and their use in treating gastrointestinal inflammatory disorders |
| KR101179012B1 (ko) | 2003-03-10 | 2012-09-03 | 니코메드 게엠베하 | 로플루미라스트 신규한 제조 방법 |
| 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 |
| MXPA05012463A (es) * | 2003-05-27 | 2006-01-30 | Altana Pharma Ag | Combinaciones farmaceuticas de un inhibidor de bomba protonica y un compuesto que modifica la motilidad gastrointestinal. |
| JP2007507425A (ja) * | 2003-08-29 | 2007-03-29 | ダイノゲン ファーマシューティカルズ，インコーポレイテッド | 胃腸管運動障害を処置するために有用な組成物 |
| WO2005025578A1 (en) | 2003-09-16 | 2005-03-24 | Altana Pharma Ag | Use of ciclesonide for the treatment of respiratory diseases |
| EP1682133A1 (en) | 2003-11-03 | 2006-07-26 | AstraZeneca AB | Imidazo 1,2-a pyridine derivatives for the treatment of silent gastro-esophageal reflux |
| CA2549860A1 (en) | 2003-12-19 | 2005-06-30 | Altana Pharma Ag | Intermediates for the preparation of tricyclic dihydropyrano -imidazo -pyridines derivatives |
| AR047605A1 (es) * | 2004-02-17 | 2006-01-25 | Altana Pharma Ag | Imidazopiridinas triciclicas e intermediarios en la sintesis de las mismas,sus procesos de preparacion,composiciones farmaceuticas que los contienen y usos. |
| ES2367312T3 (es) | 2004-09-03 | 2011-11-02 | Yuhan Corporation | DERIVADOS DE PIRROLO [3,2-c] PIRIDINA Y PROCESOS PARA LA PREPARACIÓN DE LOS MISMOS. |
| KR100958830B1 (ko) | 2004-09-03 | 2010-05-24 | 주식회사유한양행 | 피롤로[2,3-ｃ]피리딘 유도체 및 그의 제조방법 |
| ES2426920T3 (es) | 2004-09-03 | 2013-10-25 | Yuhan Corporation | Derivados de pirrolo[3,2-B]piridina y procesos para su preparación |
| EP1861074B1 (en) * | 2005-03-16 | 2013-04-24 | Takeda GmbH | Taste masked dosage form containing roflumilast |
| EP2080513A1 (en) | 2008-01-16 | 2009-07-22 | Schraermeyer, Ulrich, Prof. Dr. rer. nat | Tetrahydropyridoethers for treatment of AMD |
| US8648080B2 (en) | 2009-07-09 | 2014-02-11 | Raqualia Pharma Inc. | Acid pump antagonist for the treatment of diseases involved in abnormal gastrointestinal motility |
| WO2012027240A1 (en) * | 2010-08-23 | 2012-03-01 | Schering Corporation | Fused tricyclic inhibitors of mammalian target of rapamycin |
| EP2861571B1 (en) * | 2012-06-15 | 2017-05-03 | Bio-Pharm Solutions Co., Ltd. | Phenylalkyl sulfamate compound and muscle relaxant composition comprising the same |
| WO2015052256A1 (en) | 2013-10-08 | 2015-04-16 | Katairo Gmbh | Tetrahydropyridoethers for the treatment of stargardt's disease |
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|---|---|---|---|---|
| US4468400A (en) * | 1982-12-20 | 1984-08-28 | Schering Corporation | Antiulcer tricyclic imidazo [1,2-a]pyridines |
| CA1327796C (en) | 1987-07-16 | 1994-03-15 | Jorg Senn-Bilfinger | Diazoles |
| SE9401197D0 (sv) * | 1994-04-11 | 1994-04-11 | Astra Ab | Active compounds |
| CA2196076A1 (en) * | 1994-07-28 | 1996-02-08 | Gerhard Grundler | Acyl imidazopyridines |
| WO1998042707A1 (en) * | 1997-03-24 | 1998-10-01 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Tetrahydropyrido compounds |
| ID22718A (id) * | 1997-03-24 | 1999-12-09 | Byk Gulden Lomberg Chem Fab | Senyawa-senyawa tetrahidropirido |
| CZ292335B6 (cs) | 1998-09-23 | 2003-09-17 | Altana Pharma Ag | Tetrahydropyridoethery, jejich použití a farmaceutický prostředek |
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1999
- 1999-09-17 CZ CZ20011082A patent/CZ292335B6/cs not_active IP Right Cessation
- 1999-09-17 RS YUP-214/01A patent/RS50145B/sr unknown
- 1999-09-17 ES ES99948776T patent/ES2191464T3/es not_active Expired - Lifetime
- 1999-09-17 CA CA002344251A patent/CA2344251A1/en not_active Abandoned
- 1999-09-17 BR BR9914044-6A patent/BR9914044A/pt not_active Application Discontinuation
- 1999-09-17 IL IL14206399A patent/IL142063A0/xx active IP Right Grant
- 1999-09-17 TR TR2001/00805T patent/TR200100805T2/xx unknown
- 1999-09-17 DE DE69905178T patent/DE69905178T2/de not_active Expired - Lifetime
- 1999-09-17 WO PCT/EP1999/006899 patent/WO2000017200A1/en active IP Right Grant
- 1999-09-17 ID IDW20010682A patent/ID28896A/id unknown
- 1999-09-17 DK DK99948776T patent/DK1115725T3/da active
- 1999-09-17 AT AT99948776T patent/ATE231862T1/de not_active IP Right Cessation
- 1999-09-17 HU HU0102990A patent/HUP0102990A3/hu unknown
- 1999-09-17 SK SK399-2001A patent/SK285165B6/sk not_active IP Right Cessation
- 1999-09-17 NZ NZ510610A patent/NZ510610A/en unknown
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- 1999-09-17 CN CNB998112992A patent/CN1155598C/zh not_active Expired - Fee Related
- 1999-09-17 US US09/582,212 patent/US6436953B1/en not_active Expired - Lifetime
- 1999-09-17 KR KR1020017003553A patent/KR100668400B1/ko not_active IP Right Cessation
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- 1999-09-17 JP JP2000574109A patent/JP4145492B2/ja not_active Expired - Lifetime
- 1999-09-17 EA EA200100315A patent/EA005377B1/ru not_active IP Right Cessation
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- 1999-09-17 PT PT99948776T patent/PT1115725E/pt unknown
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2001
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2002
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