KR20050074605A - Ltd4 길항근으로서의 신규 트리시클릭 유도체 - Google Patents
Ltd4 길항근으로서의 신규 트리시클릭 유도체 Download PDFInfo
- Publication number
- KR20050074605A KR20050074605A KR1020057008474A KR20057008474A KR20050074605A KR 20050074605 A KR20050074605 A KR 20050074605A KR 1020057008474 A KR1020057008474 A KR 1020057008474A KR 20057008474 A KR20057008474 A KR 20057008474A KR 20050074605 A KR20050074605 A KR 20050074605A
- Authority
- KR
- South Korea
- Prior art keywords
- dihydro
- benzooxepino
- thio
- compound
- pyridin
- 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.)
- Withdrawn
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- -1 monoalkylamino Chemical group 0.000 claims description 200
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 48
- 125000001424 substituent group Chemical group 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000005843 halogen group Chemical group 0.000 claims description 29
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims description 12
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
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- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
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- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 8
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- BPNOGBPLSZHUGE-UHFFFAOYSA-N 2-[1-[[9-[(6,7-difluoroquinolin-2-yl)methoxy]-5,11-dihydro-[1]benzoxepino[3,4-b]pyridin-11-yl]sulfanylmethyl]cyclopropyl]acetic acid Chemical compound C12=CC=CN=C2COC2=CC=C(OCC=3N=C4C=C(F)C(F)=CC4=CC=3)C=C2C1SCC1(CC(=O)O)CC1 BPNOGBPLSZHUGE-UHFFFAOYSA-N 0.000 claims description 4
- JOKNXIFFQCWFHL-UHFFFAOYSA-N 3-[[9-[(6,7-difluoroquinolin-2-yl)methoxy]-5-methyl-6,11-dihydropyrido[2,3-c][2]benzazepin-11-yl]sulfanyl]propanoic acid Chemical compound C1=C2C(SCCC(O)=O)C3=CC=CN=C3N(C)CC2=CC=C1OCC1=CC=C(C=C(F)C(F)=C2)C2=N1 JOKNXIFFQCWFHL-UHFFFAOYSA-N 0.000 claims description 4
- BCTLZWXWOKDEJF-ZZXKWVIFSA-N 3-[[9-[(e)-2-(6,7-difluoroquinolin-2-yl)ethenyl]-5,11-dihydro-[1]benzoxepino[4,3-b]pyridin-11-yl]sulfanyl]propanoic acid Chemical compound O1CC2=CC=CN=C2C(SCCC(=O)O)C2=CC(\C=C\C=3N=C4C=C(F)C(F)=CC4=CC=3)=CC=C21 BCTLZWXWOKDEJF-ZZXKWVIFSA-N 0.000 claims description 4
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- KBNWIWYCOPKHBC-UHFFFAOYSA-N 2-[1-[[9-[(6,7-difluoroquinolin-2-yl)methoxy]-5,11-dihydro-[1]benzoxepino[4,3-b]pyridin-11-yl]sulfanylmethyl]cyclopropyl]acetic acid Chemical compound C12=CC(OCC=3N=C4C=C(F)C(F)=CC4=CC=3)=CC=C2OCC2=CC=CN=C2C1SCC1(CC(=O)O)CC1 KBNWIWYCOPKHBC-UHFFFAOYSA-N 0.000 claims description 3
- GYYISXLMDPGNDD-ZZXKWVIFSA-N 2-[1-[[9-[(e)-2-(6,7-difluoroquinolin-2-yl)ethenyl]-5,11-dihydro-[1]benzoxepino[3,4-b]pyridin-11-yl]sulfanylmethyl]cyclopropyl]acetic acid Chemical compound C12=CC=CN=C2COC2=CC=C(\C=C\C=3N=C4C=C(F)C(F)=CC4=CC=3)C=C2C1SCC1(CC(=O)O)CC1 GYYISXLMDPGNDD-ZZXKWVIFSA-N 0.000 claims description 3
- ROJDXFZAEPIOCC-UHFFFAOYSA-N 2-[[9-[(7-chloro-6-fluoroquinolin-2-yl)methoxy]-5,11-dihydro-[1]benzoxepino[3,4-b]pyridin-11-yl]sulfanyl]acetic acid Chemical compound C1=C2C(SCC(=O)O)C3=CC=CN=C3COC2=CC=C1OCC1=CC=C(C=C(F)C(Cl)=C2)C2=N1 ROJDXFZAEPIOCC-UHFFFAOYSA-N 0.000 claims description 3
- OLKUFZKAFAHFAP-UHFFFAOYSA-N 3-[[9-[(6,7-difluoroquinolin-2-yl)methoxy]-5,11-dihydro-[1]benzoxepino[3,4-b]pyridin-11-yl]sulfanyl]-3-methylbutanoic acid Chemical compound C1=C2C(SC(C)(CC(O)=O)C)C3=CC=CN=C3COC2=CC=C1OCC1=CC=C(C=C(F)C(F)=C2)C2=N1 OLKUFZKAFAHFAP-UHFFFAOYSA-N 0.000 claims description 3
- WUUCIVNJEOVHOV-UHFFFAOYSA-N 3-[[9-[(6,7-difluoroquinolin-2-yl)methoxy]-5,11-dihydro-[1]benzoxepino[3,4-b]pyridin-11-yl]sulfanyl]propanoic acid Chemical compound C1=C2C(SCCC(=O)O)C3=CC=CN=C3COC2=CC=C1OCC1=CC=C(C=C(F)C(F)=C2)C2=N1 WUUCIVNJEOVHOV-UHFFFAOYSA-N 0.000 claims description 3
- WWUVRNPLHSRXHV-UHFFFAOYSA-N 3-[[9-[(6,7-difluoroquinolin-2-yl)methoxy]-5,11-dihydro-[1]benzoxepino[4,3-b]pyridin-11-yl]sulfanyl]propanoic acid Chemical compound O1CC2=CC=CN=C2C(SCCC(=O)O)C2=CC(OCC=3N=C4C=C(F)C(F)=CC4=CC=3)=CC=C21 WWUVRNPLHSRXHV-UHFFFAOYSA-N 0.000 claims description 3
- QPNKWUKRPUIIAQ-UHFFFAOYSA-N 3-[[9-[(7-chloro-6-fluoroquinolin-2-yl)methoxy]-5,11-dihydro-[1]benzoxepino[3,4-b]pyridin-11-yl]sulfanyl]propanoic acid Chemical compound C1=C2C(SCCC(=O)O)C3=CC=CN=C3COC2=CC=C1OCC1=CC=C(C=C(F)C(Cl)=C2)C2=N1 QPNKWUKRPUIIAQ-UHFFFAOYSA-N 0.000 claims description 3
- XBQBKXHXJXVKPN-ZZXKWVIFSA-N 3-[[9-[(e)-2-(6,7-difluoroquinolin-2-yl)ethenyl]-5,11-dihydro-[1]benzoxepino[3,4-b]pyridin-11-yl]sulfanyl]propanoic acid Chemical compound O1CC2=NC=CC=C2C(SCCC(=O)O)C2=CC(\C=C\C=3N=C4C=C(F)C(F)=CC4=CC=3)=CC=C21 XBQBKXHXJXVKPN-ZZXKWVIFSA-N 0.000 claims description 3
- PMSGXRLYMCEJQU-ZZXKWVIFSA-N 9-[(e)-2-(6,7-difluoroquinolin-2-yl)ethenyl]-11-[2-(2h-tetrazol-5-yl)ethylsulfanyl]-5,11-dihydro-[1]benzoxepino[3,4-b]pyridine Chemical compound N1=C2C=C(F)C(F)=CC2=CC=C1\C=C\C(C=C12)=CC=C1OCC1=NC=CC=C1C2SCCC1=NN=NN1 PMSGXRLYMCEJQU-ZZXKWVIFSA-N 0.000 claims description 3
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- 125000004423 acyloxy group Chemical group 0.000 claims description 3
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- 239000000938 histamine H1 antagonist Substances 0.000 claims description 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
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- PNOCLWDEJRKWDF-UHFFFAOYSA-N 2-[[9-[(6,7-difluoroquinolin-2-yl)methoxy]-5,11-dihydro-[1]benzoxepino[3,4-b]pyridin-11-yl]sulfanyl]acetic acid Chemical compound C1=C2C(SCC(=O)O)C3=CC=CN=C3COC2=CC=C1OCC1=CC=C(C=C(F)C(F)=C2)C2=N1 PNOCLWDEJRKWDF-UHFFFAOYSA-N 0.000 claims description 2
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- MHABCZSIDVZHOQ-UHFFFAOYSA-N 3-[[9-[(6,7-difluoroquinolin-2-yl)methoxy]-5,11-dihydro-[1]benzoxepino[3,4-b]pyridin-11-yl]sulfanyl]-2,2-dimethylpropanoic acid Chemical compound C1=C2C(SCC(C)(C)C(O)=O)C3=CC=CN=C3COC2=CC=C1OCC1=CC=C(C=C(F)C(F)=C2)C2=N1 MHABCZSIDVZHOQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005418 aryl aryl group Chemical group 0.000 claims description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 2
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- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 1
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- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000007939 sustained release tablet Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical class Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- JKVRTUCVPZTEQZ-UHFFFAOYSA-N tributyltin azide Chemical compound CCCC[Sn](CCCC)(CCCC)N=[N+]=[N-] JKVRTUCVPZTEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XQKBFQXWZCFNFF-UHFFFAOYSA-K triiodosamarium Chemical compound I[Sm](I)I XQKBFQXWZCFNFF-UHFFFAOYSA-K 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000002569 water oil cream Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
-
- 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
- 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
- A61P11/02—Nasal agents, e.g. decongestants
-
- 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
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P31/12—Antivirals
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Communicable Diseases (AREA)
- Biomedical Technology (AREA)
- Virology (AREA)
- Neurosurgery (AREA)
- Otolaryngology (AREA)
- Oncology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200202590A ES2211315B1 (es) | 2002-11-12 | 2002-11-12 | Nuevos compuestos triciclicos. |
| ES200202590 | 2002-11-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20050074605A true KR20050074605A (ko) | 2005-07-18 |
Family
ID=32309630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020057008474A Withdrawn KR20050074605A (ko) | 2002-11-12 | 2003-11-11 | Ltd4 길항근으로서의 신규 트리시클릭 유도체 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US7557212B2 (https=) |
| EP (1) | EP1560834B1 (https=) |
| JP (1) | JP2006508116A (https=) |
| KR (1) | KR20050074605A (https=) |
| CN (1) | CN100379742C (https=) |
| AT (1) | ATE399170T1 (https=) |
| AU (1) | AU2003288032A1 (https=) |
| BR (1) | BR0315462A (https=) |
| CA (1) | CA2505491A1 (https=) |
| CO (1) | CO5700775A2 (https=) |
| DE (1) | DE60321810D1 (https=) |
| EC (1) | ECSP055844A (https=) |
| ES (2) | ES2211315B1 (https=) |
| MX (1) | MXPA05005017A (https=) |
| NO (1) | NO20052858L (https=) |
| RU (1) | RU2330855C2 (https=) |
| UA (1) | UA80996C2 (https=) |
| WO (1) | WO2004043966A1 (https=) |
| ZA (1) | ZA200503806B (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2165768B1 (es) | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| US7214687B2 (en) | 1999-07-14 | 2007-05-08 | Almirall Ag | Quinuclidine derivatives and medicinal compositions containing the same |
| ATE474601T1 (de) | 2004-05-31 | 2010-08-15 | Almirall Sa | Kombinationen mit antimuskarin-wirkstoffen und pde4-hemmern |
| ES2257152B1 (es) | 2004-05-31 | 2007-07-01 | Laboratorios Almirall S.A. | Combinaciones que comprenden agentes antimuscarinicos y agonistas beta-adrenergicos. |
| RU2408584C2 (ru) | 2005-06-23 | 2011-01-10 | Мерк Шарп Энд Домэ Корп. | Ингибиторы тирозинкиназы |
| JP2009513580A (ja) * | 2005-10-21 | 2009-04-02 | メルク エンド カムパニー インコーポレーテッド | チロシンキナーゼ阻害剤 |
| TW200813021A (en) | 2006-07-10 | 2008-03-16 | Merck & Co Inc | Tyrosine kinase inhibitors |
| ES2298049B1 (es) | 2006-07-21 | 2009-10-20 | Laboratorios Almirall S.A. | Procedimiento para fabricar bromuro de 3(r)-(2-hidroxi-2,2-ditien-2-ilacetoxi)-1-(3-fenoxipropil)-1-azoniabiciclo (2.2.2) octano. |
| EP2100599A1 (en) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| EP2100598A1 (en) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| EP2108641A1 (en) | 2008-04-11 | 2009-10-14 | Laboratorios Almirall, S.A. | New substituted spiro[cycloalkyl-1,3'-indo]-2'(1'H)-one derivatives and their use as p38 mitogen-activated kinase inhibitors |
| EP2113503A1 (en) | 2008-04-28 | 2009-11-04 | Laboratorios Almirall, S.A. | New substituted indolin-2-one derivatives and their use as p39 mitogen-activated kinase inhibitors |
| EP2322176A1 (en) | 2009-11-11 | 2011-05-18 | Almirall, S.A. | New 7-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one derivatives |
| EP2510928A1 (en) | 2011-04-15 | 2012-10-17 | Almirall, S.A. | Aclidinium for use in improving the quality of sleep in respiratory patients |
| CA2842881A1 (en) | 2011-07-26 | 2013-04-11 | Rajendrasinh RATHOD | Cysteinyl leukotriene antagonists |
| JP2019081709A (ja) * | 2016-03-18 | 2019-05-30 | 石原産業株式会社 | 有害生物防除剤 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0411048A1 (en) * | 1988-04-28 | 1991-02-06 | Schering Corporation | Novel benzopyrido piperidine, piperidylidene and piperazine compounds, compositions, methods of manufacture and methods of use |
| NZ234883A (en) * | 1989-08-22 | 1995-01-27 | Merck Frosst Canada Inc | Quinolin-2-ylmethoxy indole derivatives, preparation and pharmaceutical compositions thereof |
| AU674569B2 (en) * | 1993-02-16 | 1997-01-02 | Ube Industries, Ltd. | Quinoline derivative |
| CZ298578B6 (cs) * | 1997-11-25 | 2007-11-14 | Schering Corporation | Heterocyklickou skupinou substituovaná tricyklická sloucenina a farmaceutický prostredek ji obsahující |
| US20030216571A1 (en) * | 1999-12-28 | 2003-11-20 | Yoshiaki Kuroki | Tricyclic compounds |
| JP2006151809A (ja) * | 2002-12-26 | 2006-06-15 | Ube Ind Ltd | ベンゾシクロヘプタピリジン化合物 |
-
2002
- 2002-11-12 ES ES200202590A patent/ES2211315B1/es not_active Expired - Fee Related
-
2003
- 2003-11-11 JP JP2004550982A patent/JP2006508116A/ja active Pending
- 2003-11-11 AT AT03779886T patent/ATE399170T1/de not_active IP Right Cessation
- 2003-11-11 UA UAA200505509A patent/UA80996C2/uk unknown
- 2003-11-11 US US10/534,487 patent/US7557212B2/en not_active Expired - Fee Related
- 2003-11-11 RU RU2005118757/04A patent/RU2330855C2/ru not_active IP Right Cessation
- 2003-11-11 KR KR1020057008474A patent/KR20050074605A/ko not_active Withdrawn
- 2003-11-11 BR BR0315462-9A patent/BR0315462A/pt not_active IP Right Cessation
- 2003-11-11 AU AU2003288032A patent/AU2003288032A1/en not_active Abandoned
- 2003-11-11 EP EP03779886A patent/EP1560834B1/en not_active Expired - Lifetime
- 2003-11-11 CN CNB2003801085261A patent/CN100379742C/zh not_active Expired - Fee Related
- 2003-11-11 WO PCT/EP2003/012581 patent/WO2004043966A1/en not_active Ceased
- 2003-11-11 DE DE60321810T patent/DE60321810D1/de not_active Expired - Lifetime
- 2003-11-11 ES ES03779886T patent/ES2306906T3/es not_active Expired - Lifetime
- 2003-11-11 MX MXPA05005017A patent/MXPA05005017A/es not_active Application Discontinuation
- 2003-11-11 CA CA002505491A patent/CA2505491A1/en not_active Abandoned
-
2005
- 2005-05-11 ZA ZA200503806A patent/ZA200503806B/en unknown
- 2005-06-09 EC EC2005005844A patent/ECSP055844A/es unknown
- 2005-06-10 CO CO05056627A patent/CO5700775A2/es unknown
- 2005-06-13 NO NO20052858A patent/NO20052858L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1560834B1 (en) | 2008-06-25 |
| ZA200503806B (en) | 2006-08-30 |
| ES2306906T3 (es) | 2008-11-16 |
| EP1560834A1 (en) | 2005-08-10 |
| ES2211315A1 (es) | 2004-07-01 |
| CN100379742C (zh) | 2008-04-09 |
| WO2004043966A1 (en) | 2004-05-27 |
| CN1735618A (zh) | 2006-02-15 |
| ECSP055844A (es) | 2005-09-20 |
| NO20052858L (no) | 2005-08-12 |
| CO5700775A2 (es) | 2006-11-30 |
| BR0315462A (pt) | 2005-08-23 |
| ATE399170T1 (de) | 2008-07-15 |
| UA80996C2 (en) | 2007-11-26 |
| NO20052858D0 (no) | 2005-06-13 |
| JP2006508116A (ja) | 2006-03-09 |
| MXPA05005017A (es) | 2005-08-03 |
| US7557212B2 (en) | 2009-07-07 |
| DE60321810D1 (de) | 2008-08-07 |
| AU2003288032A1 (en) | 2004-06-03 |
| RU2005118757A (ru) | 2006-02-27 |
| RU2330855C2 (ru) | 2008-08-10 |
| CA2505491A1 (en) | 2004-05-27 |
| ES2211315B1 (es) | 2005-10-16 |
| US20060116363A1 (en) | 2006-06-01 |
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| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20050512 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |