JP2003502278A - 新規のｎ−オキシド - Google Patents
新規のｎ−オキシドInfo
- Publication number
- JP2003502278A JP2003502278A JP2000593602A JP2000593602A JP2003502278A JP 2003502278 A JP2003502278 A JP 2003502278A JP 2000593602 A JP2000593602 A JP 2000593602A JP 2000593602 A JP2000593602 A JP 2000593602A JP 2003502278 A JP2003502278 A JP 2003502278A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- formula
- alkoxy
- substituted
- hydrogen
- 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- Withdrawn
Links
- 150000001204 N-oxides Chemical class 0.000 title claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 83
- 239000003814 drug Substances 0.000 claims abstract description 17
- -1 2H- tetrazol-5-yl group Chemical group 0.000 claims description 46
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- 150000002431 hydrogen Chemical group 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 208000023504 respiratory system disease Diseases 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 description 5
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 208000006673 asthma Diseases 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- BIVMWDQSMDXTCT-RYUDHWBXSA-N (1s,2s)-2-(3,4-dimethoxyphenyl)cyclohexan-1-amine Chemical compound C1=C(OC)C(OC)=CC=C1[C@H]1[C@@H](N)CCCC1 BIVMWDQSMDXTCT-RYUDHWBXSA-N 0.000 description 4
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 4
- 101000909851 Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) cAMP/cGMP dual specificity phosphodiesterase Rv0805 Proteins 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 208000010668 atopic eczema Diseases 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 210000000440 neutrophil Anatomy 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical group C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 208000017520 skin disease Diseases 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 150000003536 tetrazoles Chemical class 0.000 description 4
- 102000003390 tumor necrosis factor Human genes 0.000 description 4
- XXWONCALJGBUFK-UHFFFAOYSA-N 6-phenylphenanthridine Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2C2=CC=CC=C12 XXWONCALJGBUFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 230000000172 allergic effect Effects 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 210000002345 respiratory system Anatomy 0.000 description 3
- 239000012603 secondary packaging material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- SCTLXXMFDHZDFW-PXNSSMCTSA-N (4as,10bs)-6-[4-(2-ethyltetrazol-5-yl)phenyl]-8,9-dimethoxy-1,2,3,4,4a,10b-hexahydrophenanthridine Chemical compound CCN1N=NC(C=2C=CC(=CC=2)C=2C3=CC(OC)=C(OC)C=C3[C@@H]3CCCC[C@@H]3N=2)=N1 SCTLXXMFDHZDFW-PXNSSMCTSA-N 0.000 description 2
- CKUUWZSXSMTFIO-RYUDHWBXSA-N 1,2-dimethoxy-4-[(1s,2s)-2-nitrocyclohexyl]benzene Chemical compound C1=C(OC)C(OC)=CC=C1[C@H]1[C@@H]([N+]([O-])=O)CCCC1 CKUUWZSXSMTFIO-RYUDHWBXSA-N 0.000 description 2
- SYJMYDMKPSZMSB-AATRIKPKSA-N 1,2-dimethoxy-4-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C=C1OC SYJMYDMKPSZMSB-AATRIKPKSA-N 0.000 description 2
- 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 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 2
- 102000004127 Cytokines Human genes 0.000 description 2
- 108090000695 Cytokines Proteins 0.000 description 2
- 208000010228 Erectile Dysfunction Diseases 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 108010044467 Isoenzymes Proteins 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- 206010038419 Renal colic Diseases 0.000 description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 2
- 206010040070 Septic Shock Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 2
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- 230000029936 alkylation Effects 0.000 description 2
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- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
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- 125000004802 cyanophenyl group Chemical group 0.000 description 2
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
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- 238000000921 elemental analysis Methods 0.000 description 2
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
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- FEWOIZJGLIFICL-WOJBJXKFSA-N n-[(1r,2r)-2-(3,4-dimethoxyphenyl)cyclohexyl]-4-(2-ethyltetrazol-5-yl)benzamide Chemical compound CCN1N=NC(C=2C=CC(=CC=2)C(=O)N[C@H]2[C@H](CCCC2)C=2C=C(OC)C(OC)=CC=2)=N1 FEWOIZJGLIFICL-WOJBJXKFSA-N 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
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- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- BSGIEESBTVXEOH-UHFFFAOYSA-N 5-oxidophenanthridin-5-ium Chemical compound C1=CC=C2[N+]([O-])=CC3=CC=CC=C3C2=C1 BSGIEESBTVXEOH-UHFFFAOYSA-N 0.000 description 1
- JTKIQRJYVVHKRH-UHFFFAOYSA-N 6-pyridin-2-ylphenanthridine Chemical compound N1=CC=CC=C1C1=NC2=CC=CC=C2C2=CC=CC=C12 JTKIQRJYVVHKRH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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- 208000000884 Airway Obstruction Diseases 0.000 description 1
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- 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
- C07D401/10—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 carbon chain containing aromatic rings
-
- 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
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- 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
- A61P11/04—Drugs for disorders of the respiratory system for throat disorders
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- 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
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Junction Field-Effect Transistors (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99100693.3 | 1999-01-15 | ||
| EP99100693 | 1999-01-15 | ||
| PCT/EP2000/000192 WO2000042034A1 (en) | 1999-01-15 | 2000-01-13 | Phenanthridine-n-oxides with pde-iv inhibiting activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003502278A true JP2003502278A (ja) | 2003-01-21 |
| JP2003502278A5 JP2003502278A5 (https=) | 2007-03-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000593602A Withdrawn JP2003502278A (ja) | 1999-01-15 | 2000-01-13 | 新規のｎ−オキシド |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6534519B1 (https=) |
| EP (1) | EP1147103B1 (https=) |
| JP (1) | JP2003502278A (https=) |
| AT (1) | ATE294793T1 (https=) |
| AU (1) | AU2290000A (https=) |
| CA (1) | CA2359449A1 (https=) |
| DE (1) | DE60019894T2 (https=) |
| DK (1) | DK1147103T3 (https=) |
| ES (1) | ES2241571T3 (https=) |
| PT (1) | PT1147103E (https=) |
| SI (1) | SI1147103T1 (https=) |
| WO (1) | WO2000042034A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002534508A (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 | Ｐｅｄ−ｉｖ阻害作用を有するフェニルフェナントリジン |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2396026A1 (en) | 2000-01-11 | 2001-07-19 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Phenanthridine-n-oxides |
| PT1303506E (pt) | 2000-07-14 | 2005-06-30 | Altana Pharma Ag | 6-heteroarilfenantridinas |
| CA2495827C (en) * | 2002-08-29 | 2012-05-08 | Altana Pharma Ag | 2-hydroxy-6-phenylphenanthridines as pde-4 inhibitors |
| ES2281658T3 (es) | 2002-08-29 | 2007-10-01 | Nycomed Gmbh | 3-hidroxi-6-fenilfenantridinas como inhibidores de pde-4. |
| EP1658270A1 (en) * | 2003-07-31 | 2006-05-24 | ALTANA Pharma AG | Novel 6-phenylphenantridines |
| CA2533636A1 (en) * | 2003-07-31 | 2005-02-10 | Altana Pharma Ag | Novel 6-phenylphenanthridines |
| US20050187278A1 (en) * | 2003-08-28 | 2005-08-25 | Pharmacia Corporation | Treatment or prevention of vascular disorders with Cox-2 inhibitors in combination with cyclic AMP-specific phosphodiesterase inhibitors |
| WO2005023253A1 (en) * | 2003-09-05 | 2005-03-17 | Altana Pharma Ag | Use of pde4 inhibitors for the treatment of diabetes mellitus |
| AU2005212857B2 (en) | 2004-02-18 | 2011-04-28 | Takeda Gmbh | Novel guanidinyl-substituted hydroxy-6-phenylphenenthridines as effective phosphodiesterase (PDE) 4 inhibitors |
| AR049419A1 (es) * | 2004-03-03 | 2006-08-02 | Altana Pharma Ag | Hidroxi-6-fenilfenantridinas sustituidas con heterociclilo |
| CN104803974A (zh) | 2004-03-03 | 2015-07-29 | 塔科达有限责任公司 | 新的羟基-6-杂芳基菲啶及其作为pde4抑制剂的用途 |
| JP2007527901A (ja) * | 2004-03-10 | 2007-10-04 | アルタナ ファルマ アクチエンゲゼルシャフト | アミド置換された新規のヒドロキシ−６−フェニルフェナントリジン及びｐｄｅ４インヒビターとしてのそれらの使用 |
| ES2337083T3 (es) | 2005-03-02 | 2010-04-20 | Nycomed Gmbh | (2r,4ar,10br)-6-(2,6-dimetoxipiridin-3-il)-9-exoti-8-metoxi-1,2,3,4,4a,10b-hexahidrofenantridin-2-ol, sal de hc1. |
| AU2006222060B2 (en) | 2005-03-08 | 2011-09-01 | Takeda Gmbh | Roflumilast for the treatment of diabetes mellitus |
| MX2010003155A (es) | 2007-10-04 | 2010-04-01 | Hoffmann La Roche | Derivados de ciclopropil aril amida y uso de los mismos. |
| WO2013106547A1 (en) | 2012-01-10 | 2013-07-18 | President And Fellows Of Harvard College | Beta-cell replication promoting compounds and methods of their use |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5455252A (en) * | 1993-03-31 | 1995-10-03 | Syntex (U.S.A.) Inc. | Optionally substituted 6,8-quinolines |
| US5475003A (en) * | 1994-03-03 | 1995-12-12 | Syntex (U.S.A.) Inc. | 8-phenylcyclopentenoquinoline and 8-phenylcyclohexenoquinoline derivatives |
| CA2143143A1 (en) * | 1994-03-08 | 1995-09-09 | Toshihiko Tanaka | 3-phenylpyrrolidine derivatives |
| US5466697A (en) * | 1994-07-13 | 1995-11-14 | Syntex (U.S.A.) Inc. | 8-phenyl-1,6-naphthyridin-5-ones |
| UA48216C2 (uk) | 1996-01-31 | 2002-08-15 | Бік Гулден Ломберг Кеміше Фабрік Гмбх | Фенантридини та лікарський засіб для лікування захворювань дихальних шляхів |
| US6127378A (en) | 1996-03-26 | 2000-10-03 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Phenanthridines substituted in the 6 position |
| WO1997035854A1 (de) * | 1996-03-26 | 1997-10-02 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Neue in 6-position substituierte phenanthridine |
| GB9622386D0 (en) | 1996-10-28 | 1997-01-08 | Sandoz Ltd | Organic compounds |
| EE03829B1 (et) | 1996-11-11 | 2002-08-15 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Bensonaftüridiinid, nende kasutamine bronhiaalravimi valmistamiseks ning neid sisaldav ravim |
| GB9626643D0 (en) | 1996-12-21 | 1997-02-12 | Astra Pharma Prod | Compounds |
| JP2001514640A (ja) | 1997-03-07 | 2001-09-11 | 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 | 新規のテトラゾール |
| CA2291153A1 (en) | 1997-06-03 | 1998-12-10 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Benzonaphthyridine |
| DE69822162T2 (de) | 1997-07-25 | 2005-01-27 | Altana Pharma Ag | Neue tetrazolderivate |
| AU5970199A (en) | 1998-08-31 | 2000-03-21 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Benzonaphthyridine-n-oxides comprising a pde3 and pde4 inhibiting activity |
-
2000
- 2000-01-13 AT AT00901539T patent/ATE294793T1/de not_active IP Right Cessation
- 2000-01-13 JP JP2000593602A patent/JP2003502278A/ja not_active Withdrawn
- 2000-01-13 ES ES00901539T patent/ES2241571T3/es not_active Expired - Lifetime
- 2000-01-13 US US09/889,146 patent/US6534519B1/en not_active Expired - Fee Related
- 2000-01-13 PT PT00901539T patent/PT1147103E/pt unknown
- 2000-01-13 CA CA002359449A patent/CA2359449A1/en not_active Abandoned
- 2000-01-13 DK DK00901539T patent/DK1147103T3/da active
- 2000-01-13 DE DE60019894T patent/DE60019894T2/de not_active Expired - Fee Related
- 2000-01-13 AU AU22900/00A patent/AU2290000A/en not_active Abandoned
- 2000-01-13 WO PCT/EP2000/000192 patent/WO2000042034A1/en not_active Ceased
- 2000-01-13 EP EP00901539A patent/EP1147103B1/en not_active Expired - Lifetime
- 2000-01-13 SI SI200030713T patent/SI1147103T1/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002534508A (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 | Ｐｅｄ−ｉｖ阻害作用を有するフェニルフェナントリジン |
Also Published As
| Publication number | Publication date |
|---|---|
| DK1147103T3 (da) | 2005-08-29 |
| DE60019894D1 (de) | 2005-06-09 |
| DE60019894T2 (de) | 2006-01-12 |
| CA2359449A1 (en) | 2000-07-20 |
| EP1147103B1 (en) | 2005-05-04 |
| WO2000042034A1 (en) | 2000-07-20 |
| ES2241571T3 (es) | 2005-11-01 |
| PT1147103E (pt) | 2005-08-31 |
| SI1147103T1 (en) | 2005-10-31 |
| ATE294793T1 (de) | 2005-05-15 |
| EP1147103A1 (en) | 2001-10-24 |
| US6534519B1 (en) | 2003-03-18 |
| AU2290000A (en) | 2000-08-01 |
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