IL129054A - History of xahydrobenzoic acid [C] [1,6] Naphthiridine - 6-benzoyl moiety converted in the three positions 9,8,2 and pharmaceutical preparations containing them - Google Patents
History of xahydrobenzoic acid [C] [1,6] Naphthiridine - 6-benzoyl moiety converted in the three positions 9,8,2 and pharmaceutical preparations containing themInfo
- Publication number
- IL129054A IL129054A IL12905497A IL12905497A IL129054A IL 129054 A IL129054 A IL 129054A IL 12905497 A IL12905497 A IL 12905497A IL 12905497 A IL12905497 A IL 12905497A IL 129054 A IL129054 A IL 129054A
- Authority
- IL
- Israel
- Prior art keywords
- compounds
- alkoxy
- salts
- solvates
- hydrates
- Prior art date
Links
- -1 2,8,9-trisubstituted-hexahydrobenzo [c] [1,6] naphthyridin-6-yl benzoic acid Chemical class 0.000 title claims abstract description 75
- 239000008194 pharmaceutical composition Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 125
- 150000003839 salts Chemical class 0.000 claims abstract description 56
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 34
- 239000012453 solvate Substances 0.000 claims abstract description 34
- 150000004677 hydrates Chemical class 0.000 claims abstract description 30
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 27
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 24
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 20
- 239000011737 fluorine Substances 0.000 claims abstract description 20
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical group 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 141
- 230000003287 optical effect Effects 0.000 claims description 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 13
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 8
- VSOSXKMEQPYESP-UHFFFAOYSA-N 1,6-naphthyridine Chemical compound C1=CN=CC2=CC=CN=C21 VSOSXKMEQPYESP-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 208000017520 skin disease Diseases 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- BWYRUGYLRJXRFN-AXEKQOJOSA-N (3r,4s)-3-(3,4-diethoxyphenyl)-1-methylpiperidin-4-amine;dihydrochloride Chemical compound Cl.Cl.C1=C(OCC)C(OCC)=CC=C1[C@H]1[C@@H](N)CCN(C)C1 BWYRUGYLRJXRFN-AXEKQOJOSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- GOZNZGWCQSNZFX-UHFFFAOYSA-N 1,6-naphthyridine;hydrochloride Chemical compound Cl.C1=CN=CC2=CC=CN=C21 GOZNZGWCQSNZFX-UHFFFAOYSA-N 0.000 claims 1
- ZPDJVYKXQOSYIE-UHFFFAOYSA-N 1-methylpiperidin-1-ium;chloride;hydrochloride Chemical compound Cl.Cl.CN1CCCCC1 ZPDJVYKXQOSYIE-UHFFFAOYSA-N 0.000 claims 1
- BYXCINYJZUMIJI-UHFFFAOYSA-N benzo[c][1,6]naphthyridine Chemical compound C1=NC=C2C3=CC=CC=C3C=NC2=C1 BYXCINYJZUMIJI-UHFFFAOYSA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 abstract description 6
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract description 3
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- 238000000921 elemental analysis Methods 0.000 description 26
- 238000000034 method Methods 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
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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 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- QYQKEEKSROGRBQ-UHFFFAOYSA-N 6-phenylbenzo[b][1,8]naphthyridine Chemical class C1=CC=CC=C1C1=CC=CC2=NC3=NC=CC=C3C=C12 QYQKEEKSROGRBQ-UHFFFAOYSA-N 0.000 description 2
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- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
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- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
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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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- 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
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurology (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Neurosurgery (AREA)
- Hematology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19646298 | 1996-11-11 | ||
| EP96118188 | 1996-11-13 | ||
| DE19739056 | 1997-09-05 | ||
| PCT/EP1997/006096 WO1998021208A1 (en) | 1996-11-11 | 1997-11-05 | Benzonaphthyridines as bronchial therapeutics |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL129054A0 IL129054A0 (en) | 2000-02-17 |
| IL129054A true IL129054A (en) | 2002-07-25 |
Family
ID=27216810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12905497A IL129054A (en) | 1996-11-11 | 1997-11-05 | History of xahydrobenzoic acid [C] [1,6] Naphthiridine - 6-benzoyl moiety converted in the three positions 9,8,2 and pharmaceutical preparations containing them |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6008215A (xx) |
| EP (1) | EP0937074B1 (xx) |
| JP (1) | JP4223075B2 (xx) |
| KR (1) | KR100484045B1 (xx) |
| CN (1) | CN1090188C (xx) |
| AT (1) | ATE234300T1 (xx) |
| AU (1) | AU733129B2 (xx) |
| BG (1) | BG63695B1 (xx) |
| BR (1) | BR9713338B1 (xx) |
| CA (1) | CA2270964C (xx) |
| CY (1) | CY2476B1 (xx) |
| CZ (1) | CZ288752B6 (xx) |
| DE (1) | DE69719778T2 (xx) |
| DK (1) | DK0937074T3 (xx) |
| EA (1) | EA001551B1 (xx) |
| EE (1) | EE03829B1 (xx) |
| ES (1) | ES2195189T3 (xx) |
| GE (1) | GEP20012390B (xx) |
| HK (1) | HK1022151A1 (xx) |
| HU (1) | HU226981B1 (xx) |
| ID (1) | ID22042A (xx) |
| IL (1) | IL129054A (xx) |
| NO (1) | NO312764B1 (xx) |
| NZ (1) | NZ334976A (xx) |
| PL (1) | PL189641B1 (xx) |
| PT (1) | PT937074E (xx) |
| RS (1) | RS49607B (xx) |
| SI (1) | SI0937074T1 (xx) |
| SK (1) | SK283269B6 (xx) |
| TR (1) | TR199900856T2 (xx) |
| WO (1) | WO1998021208A1 (xx) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE234301T1 (de) | 1998-05-05 | 2003-03-15 | Altana Pharma Ag | Neue benzonaphtyridin-n-oxide |
| US6436952B1 (en) | 1998-08-31 | 2002-08-20 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Benzonaphthyridine-N-oxides comprising a PDE3 and PDE4 inhibiting activity |
| IT1303272B1 (it) | 1998-10-29 | 2000-11-06 | Zambon Spa | Derivati triciclici inibitori della fosfodiesterasi 4 |
| AU2107700A (en) | 1999-01-15 | 2000-08-01 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Phenanthridine-n-oxides with pde-iv inhibiting activity |
| JP2002534506A (ja) | 1999-01-15 | 2002-10-15 | ビイク グルデン ロンベルク ヒエーミツシエ フアブリーク ゲゼルシヤフト ミツト ベシユレンクテル ハフツング | Ｐｄｅ−ｉｖ抑制作用を有する多重に置換された６−フェニルフェナントリジン |
| SI1147103T1 (en) | 1999-01-15 | 2005-10-31 | Altana Pharma Ag | Phenantrhridine-n-oxides with pde-iv inhibiting activity |
| ATE312081T1 (de) * | 1999-01-15 | 2005-12-15 | Altana Pharma Ag | 6-phenylphenanthridine mit pde-iv hemmender wirkung |
| SI1212089T1 (sl) | 1999-08-21 | 2006-08-31 | Altana Pharma Ag | Sinergisticna kombinacija roflumilasta in salmeterola |
| NL1017973C2 (nl) * | 2000-05-10 | 2002-11-08 | Tristem Trading Cyprus Ltd | Inrichting. |
| CA2438717C (en) * | 2001-02-21 | 2011-08-30 | Altana Pharma Ag | 6-phenylbenzonaphthyridines |
| US6479493B1 (en) | 2001-08-23 | 2002-11-12 | Cell Pathways, Inc. | Methods for treatment of type I diabetes |
| EP1581533A2 (en) * | 2002-08-17 | 2005-10-05 | ALTANA Pharma AG | Novel benzonaphthyridines |
| EP1537109B1 (en) * | 2002-09-04 | 2007-04-18 | ALTANA Pharma AG | Novel benzonaphthyridines |
| US7470704B2 (en) * | 2002-09-04 | 2008-12-30 | Nycomed Gmbh | Benzonaphthyridines |
| KR101152488B1 (ko) | 2004-03-03 | 2012-07-02 | 니코메드 게엠베하 | 신규 히드록시-6-헤테로아릴페난트리딘 및 ｐｄｅ4 억제제로서의 이의 용도 |
| AR049419A1 (es) * | 2004-03-03 | 2006-08-02 | Altana Pharma Ag | Hidroxi-6-fenilfenantridinas sustituidas con heterociclilo |
| WO2005087745A1 (en) * | 2004-03-10 | 2005-09-22 | Altana Pharma Ag | Novel amido-substituted hydroxy-6-phenylphenanthridines and their use as pde4 inhibitors |
| EP1732925A1 (en) * | 2004-03-17 | 2006-12-20 | Altana Pharma AG | Novel n-(alkoxyalkyl)carbamoyl- substituted 6-phenyl-benzonaphthyridine derivatives and their use as pde3/4 inhibitors |
| ES2365926T3 (es) * | 2004-09-08 | 2011-10-13 | Nycomed Gmbh | 3-oxa-10-aza-fenantrenos como inhibidores de pde4 o pde3/4. |
| US7589205B2 (en) * | 2004-09-08 | 2009-09-15 | Nycomed Gmbh | 3-thia-10-aza-phenanthrene derivatives |
| SI1856093T1 (sl) * | 2005-03-02 | 2010-03-31 | Nycomed Gmbh | Hidrokloridna sol R aR bR dimetoksipiridin il etoksi metoksi a b heksahidrofenantridin ola |
| JP2009512676A (ja) | 2005-10-19 | 2009-03-26 | ランバクシー ラボラトリーズ リミテッド | ムスカリン性受容体アンタゴニストの医薬組成物 |
| TW200808695A (en) * | 2006-06-08 | 2008-02-16 | Amgen Inc | Benzamide derivatives and uses related thereto |
| JP5399905B2 (ja) * | 2006-09-01 | 2014-01-29 | センワ バイオサイエンシズ インコーポレイテッド | セリン−トレオニンタンパク質キナーゼおよびｐａｒｐ調節因子 |
| EP2276761B1 (en) | 2008-04-23 | 2015-07-29 | Rigel Pharmaceuticals, Inc. | Carboxamide compounds for the treatment of metabolic disorders |
| AR079451A1 (es) | 2009-12-18 | 2012-01-25 | Nycomed Gmbh | Compuestos 3,4,4a,10b-tetrahidro-1h-tiopirano[4,3-c]isoquinolina |
| CN108299429B (zh) * | 2018-04-09 | 2021-10-08 | 中南大学 | 一类八氢苯并萘啶化合物及其制备方法和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3899494A (en) * | 1970-05-13 | 1975-08-12 | Sandoz Ltd | Substituted 6-phenyl benzo-naphthyridines |
| EP0247971A3 (en) * | 1986-05-29 | 1990-01-17 | Sandoz Ag | Novel pharmaceutical compositions comprising and use of cis-6-(4-acetanilido)-8,9-dimethoxy-2-methyl-1,2,3,4,4a,10b-hexahydrobenzo[c][1,6]naphthyridin |
| MY105344A (en) * | 1990-05-16 | 1994-09-30 | Byk Gulden Lomberg Chemische Fabrik | New sulphonyl compounds |
-
1997
- 1997-11-05 SK SK623-99A patent/SK283269B6/sk not_active IP Right Cessation
- 1997-11-05 CZ CZ19991675A patent/CZ288752B6/cs not_active IP Right Cessation
- 1997-11-05 SI SI9730535T patent/SI0937074T1/xx unknown
- 1997-11-05 EA EA199900421A patent/EA001551B1/ru not_active IP Right Cessation
- 1997-11-05 WO PCT/EP1997/006096 patent/WO1998021208A1/en active IP Right Grant
- 1997-11-05 TR TR1999/00856T patent/TR199900856T2/xx unknown
- 1997-11-05 ES ES97950093T patent/ES2195189T3/es not_active Expired - Lifetime
- 1997-11-05 JP JP52212098A patent/JP4223075B2/ja not_active Expired - Fee Related
- 1997-11-05 IL IL12905497A patent/IL129054A/en not_active IP Right Cessation
- 1997-11-05 BR BRPI9713338-8A patent/BR9713338B1/pt not_active IP Right Cessation
- 1997-11-05 RS YUP-194/99A patent/RS49607B/sr unknown
- 1997-11-05 CA CA002270964A patent/CA2270964C/en not_active Expired - Fee Related
- 1997-11-05 AT AT97950093T patent/ATE234300T1/de active
- 1997-11-05 AU AU53170/98A patent/AU733129B2/en not_active Ceased
- 1997-11-05 PL PL97333429A patent/PL189641B1/pl unknown
- 1997-11-05 KR KR10-1999-7004024A patent/KR100484045B1/ko not_active IP Right Cessation
- 1997-11-05 ID IDW990180A patent/ID22042A/id unknown
- 1997-11-05 DE DE69719778T patent/DE69719778T2/de not_active Expired - Lifetime
- 1997-11-05 DK DK97950093T patent/DK0937074T3/da active
- 1997-11-05 EP EP97950093A patent/EP0937074B1/en not_active Expired - Lifetime
- 1997-11-05 US US09/284,458 patent/US6008215A/en not_active Expired - Lifetime
- 1997-11-05 CN CN97199529A patent/CN1090188C/zh not_active Expired - Fee Related
- 1997-11-05 EE EEP199900105A patent/EE03829B1/xx not_active IP Right Cessation
- 1997-11-05 PT PT97950093T patent/PT937074E/pt unknown
- 1997-11-05 GE GEAP19974710A patent/GEP20012390B/en unknown
- 1997-11-05 NZ NZ334976A patent/NZ334976A/xx not_active IP Right Cessation
- 1997-11-05 HU HU0000426A patent/HU226981B1/hu not_active IP Right Cessation
-
1999
- 1999-04-05 BG BG103310A patent/BG63695B1/bg unknown
- 1999-05-11 NO NO19992282A patent/NO312764B1/no not_active IP Right Cessation
-
2000
- 2000-02-24 HK HK00101112A patent/HK1022151A1/xx not_active IP Right Cessation
-
2004
- 2004-09-03 CY CY0400068A patent/CY2476B1/xx unknown
Also Published As
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| EP0968211B1 (en) | Tetrazole derivatives | |
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| MM9K | Patent not in force due to non-payment of renewal fees |