ZA200306815B - Phthalayinone-piperidino-derivatives as PDE4 inhibitors. - Google Patents
Phthalayinone-piperidino-derivatives as PDE4 inhibitors. Download PDFInfo
- Publication number
- ZA200306815B ZA200306815B ZA200306815A ZA200306815A ZA200306815B ZA 200306815 B ZA200306815 B ZA 200306815B ZA 200306815 A ZA200306815 A ZA 200306815A ZA 200306815 A ZA200306815 A ZA 200306815A ZA 200306815 B ZA200306815 B ZA 200306815B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- alkyl
- alkoxy
- tetrahydro
- piperidin
- Prior art date
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- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title description 3
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title description 3
- -1 5-dimethylaminonaphthalin-1-yl Chemical group 0.000 claims description 138
- 150000001875 compounds Chemical class 0.000 claims description 94
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 94
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims description 55
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 125000004076 pyridyl group Chemical group 0.000 claims description 22
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 239000011737 fluorine Substances 0.000 claims description 17
- 125000001153 fluoro group Chemical group F* 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 11
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 10
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000003003 spiro group Chemical group 0.000 claims description 7
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 150000002430 hydrocarbons Chemical group 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- VBKPPDYGFUZOAJ-UHFFFAOYSA-N 5-oxopentanoic acid Chemical compound OC(=O)CCCC=O VBKPPDYGFUZOAJ-UHFFFAOYSA-N 0.000 claims description 3
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
- GSDIOOSPCUFPSE-UHFFFAOYSA-N 3,4,4a,5-tetrahydro-2h-phthalazin-1-one Chemical compound C1C=CC=C2C(=O)NNCC21 GSDIOOSPCUFPSE-UHFFFAOYSA-N 0.000 claims description 2
- OEFNVAZNTGKKSO-CTNGQTDRSA-N C1=2CC(C)(C)OC=2C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1C1CCN(C(=O)NC(C)(C)C)CC1 Chemical compound C1=2CC(C)(C)OC=2C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1C1CCN(C(=O)NC(C)(C)C)CC1 OEFNVAZNTGKKSO-CTNGQTDRSA-N 0.000 claims description 2
- JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical group C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-UHFFFAOYSA-N 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 235000013350 formula milk Nutrition 0.000 claims 27
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical compound C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 claims 2
- QWJOSUUTFBUYBX-DUXSLQFZSA-N (4aS,8aR)-4-(3,4-dimethoxyphenyl)-2-[1-(1-phenylethyl)piperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(C(C)C=2C=CC=CC=2)CC1 QWJOSUUTFBUYBX-DUXSLQFZSA-N 0.000 claims 1
- IRQAORMVIRUVSL-IZZNHLLZSA-N (4as,8ar)-4-(3,4-diethoxyphenyl)-2-[1-(4-methylphenyl)sulfonylpiperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OCC)C(OCC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(S(=O)(=O)C=2C=CC(C)=CC=2)CC1 IRQAORMVIRUVSL-IZZNHLLZSA-N 0.000 claims 1
- WGTSMCZWJIQJKN-WUFINQPMSA-N (4as,8ar)-4-(3,4-diethoxyphenyl)-2-[1-[2-[4-[2-(dimethylamino)ethyl]piperazin-1-yl]acetyl]piperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OCC)C(OCC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(C(=O)CN2CCN(CCN(C)C)CC2)CC1 WGTSMCZWJIQJKN-WUFINQPMSA-N 0.000 claims 1
- YWHBSFAATHJDAA-VQTJNVASSA-N (4as,8ar)-4-(3,4-dimethoxyphenyl)-2-(1-pyrimidin-2-ylpiperidin-4-yl)-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(C=2N=CC=CN=2)CC1 YWHBSFAATHJDAA-VQTJNVASSA-N 0.000 claims 1
- AMRVEJYMDSINDP-XZOQPEGZSA-N (4as,8ar)-4-(3,4-dimethoxyphenyl)-2-[1-(4-nitrophenyl)piperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(C=2C=CC(=CC=2)[N+]([O-])=O)CC1 AMRVEJYMDSINDP-XZOQPEGZSA-N 0.000 claims 1
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- IDSNOSDXUZNXFS-RRPNLBNLSA-N (4as,8ar)-4-(3,4-dimethoxyphenyl)-2-[1-[5-(dimethylamino)naphthalen-1-yl]sulfonylpiperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(S(=O)(=O)C=2C3=CC=CC(=C3C=CC=2)N(C)C)CC1 IDSNOSDXUZNXFS-RRPNLBNLSA-N 0.000 claims 1
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- LWBCVAKHMSFVIE-FCHUYYIVSA-N 4-[(4as,8ar)-4-(3,4-diethoxyphenyl)-1-oxo-4a,5,8,8a-tetrahydrophthalazin-2-yl]-n-tert-butylpiperidine-1-carboxamide Chemical compound C1=C(OCC)C(OCC)=CC=C1C([C@H]1CC=CC[C@H]1C1=O)=NN1C1CCN(C(=O)NC(C)(C)C)CC1 LWBCVAKHMSFVIE-FCHUYYIVSA-N 0.000 claims 1
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- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- 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
- A61P9/08—Vasodilators for multiple indications
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- 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
- C07D401/14—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 three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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Applications Claiming Priority (1)
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EP01103496 | 2001-02-15 |
Publications (1)
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ZA200306815B true ZA200306815B (en) | 2004-06-17 |
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ZA200306815A ZA200306815B (en) | 2001-02-15 | 2003-09-01 | Phthalayinone-piperidino-derivatives as PDE4 inhibitors. |
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US (3) | US6953853B2 (hu) |
EP (1) | EP1362044A1 (hu) |
JP (1) | JP4301812B2 (hu) |
KR (1) | KR20030074817A (hu) |
CN (1) | CN1524080A (hu) |
AU (1) | AU2002234634B2 (hu) |
BG (1) | BG108124A (hu) |
BR (1) | BR0207278A (hu) |
CA (1) | CA2438520C (hu) |
CZ (1) | CZ20032491A3 (hu) |
EA (1) | EA200300836A1 (hu) |
EE (1) | EE05386B1 (hu) |
HR (1) | HRP20030636B1 (hu) |
HU (1) | HUP0303193A3 (hu) |
IL (1) | IL156812A0 (hu) |
MX (1) | MXPA03007310A (hu) |
NO (1) | NO325245B1 (hu) |
NZ (1) | NZ527424A (hu) |
PL (1) | PL363391A1 (hu) |
SK (1) | SK11382003A3 (hu) |
WO (1) | WO2002064584A1 (hu) |
ZA (1) | ZA200306815B (hu) |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
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CZ20032491A3 (cs) | 2001-02-15 | 2004-01-14 | Altana Pharma Ag | Ftalazinonpiperidinové deriváty |
PL210463B1 (pl) * | 2001-09-19 | 2012-01-31 | Nycomed Gmbh | Zastosowanie kombinacji roflumilastu z diklofenakiem w leczeniu zapalnych chorób stawów |
MXPA05001354A (es) * | 2002-08-10 | 2005-04-28 | Altana Pharma Ag | Piperidina-ftalazonas sustituidas por pirrolidinodiona como inhibidores pde4. |
PL373146A1 (en) * | 2002-08-10 | 2005-08-22 | Altana Pharma Ag | Pyridazinone-derivatives as pde4 inhibitors |
AU2003255376A1 (en) * | 2002-08-10 | 2004-03-11 | Altana Pharma Ag | Piperidine-derivatives as pde4 inhibitors |
PL373597A1 (en) * | 2002-08-10 | 2005-09-05 | Altana Pharma Ag | Piperidine-n-oxide-derivatives |
PL378247A1 (pl) * | 2003-01-14 | 2006-03-20 | Altana Pharma Ag | Inhibitory PDE4 w terapii nowotworów komórek limfoidalnych |
WO2004098605A1 (en) * | 2003-05-12 | 2004-11-18 | Altana Pharma Ag | Pharmaceutical composition comprising a pde4 inhibitor and il-1 trap |
WO2004098606A1 (en) * | 2003-05-12 | 2004-11-18 | Altana Pharma Ag | Composition comprising a pde4 inhibitor and shuil-1r ii |
WO2004098578A2 (en) * | 2003-05-12 | 2004-11-18 | Altana Pharma Ag | Composition comprising a pde4 inhibitor and a tnf-alfa antagonist selected from infliximab, adalimumab, cdp870 and cdp517 |
WO2004098633A1 (en) * | 2003-05-12 | 2004-11-18 | Altana Pharma Ag | Composition comprising a pde-4 inhibitor and a tnf alpha antagonist |
JP2006528229A (ja) * | 2003-05-22 | 2006-12-14 | アルタナ ファルマ アクチエンゲゼルシャフト | Pde4阻害剤及びpde5阻害剤を含有する組成物 |
US7776893B2 (en) | 2003-09-05 | 2010-08-17 | Nycomed Gmbh | Use of PDE4 inhibitors for the treatment of diabetes mellitus |
JP4778449B2 (ja) * | 2004-02-04 | 2011-09-21 | 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 | Pde4インヒビターとしての2−(ピペリジン−4−イル)−4,5−ジヒドロ−2h−ピリダジン−3−オン誘導体 |
EP1716123A1 (en) * | 2004-02-04 | 2006-11-02 | Altana Pharma AG | Pyridazinone derivatives and their use as pde4 inhibitors |
EP1720854A1 (en) * | 2004-02-04 | 2006-11-15 | Altana Pharma AG | Phthalzinone derivatives as pde4 inhibitors |
EA015382B1 (ru) | 2005-03-08 | 2011-08-30 | Никомед Гмбх | Применение рофлумиласта для лечения сахарного диабета типа 2 |
CA2628570A1 (en) | 2005-11-09 | 2007-05-18 | Combinatorx, Incorporated | Methods, compositions, and kits for the treatment of medical conditions |
US20080004271A1 (en) * | 2006-01-17 | 2008-01-03 | Mckenna Jeffrey M | Inhibitors of TNFalpha, PDE4 and B-RAF, compositions thereof and methods of use therewith |
ATE535244T1 (de) | 2006-07-05 | 2011-12-15 | Nycomed Gmbh | Kombination aus atorvastatin mit einem phosphodiesterase-4-hemmer zur behandlung von entzündlichen lungenerkrankungen |
ES2341813T3 (es) * | 2006-12-20 | 2010-06-28 | Glaxo Group Limited | 4-bencil-1 (2h)-ftalazinonas como antagonistas del receptor h1. |
MY154498A (en) | 2007-05-16 | 2015-06-30 | Takeda Gmbh | Pyrazolone derivatives as pde4 inhibitors |
AR074318A1 (es) | 2008-11-14 | 2011-01-05 | Nycomed Gmbh | Derivados heterociclicos de pirazolona, composiciones farmaceuticas que los contienen y uso de los mismos para el tratamiento de enfermedades de las vias respiratorias. |
EP2517058B1 (en) * | 2009-12-21 | 2020-07-15 | Hewlett-Packard Enterprise Development LP | Circuit switched optical interconnection fabric |
CA2837248A1 (en) | 2011-06-17 | 2012-12-20 | Takeda Gmbh | Novel phthalazinone -pyrrolopyrimidinecarboxamide derivatives |
WO2013106547A1 (en) | 2012-01-10 | 2013-07-18 | President And Fellows Of Harvard College | Beta-cell replication promoting compounds and methods of their use |
EP3165224A1 (en) | 2015-11-09 | 2017-05-10 | Albert-Ludwigs-Universität Freiburg | Use of pde4 inhibitors for the prophylaxis and/or therapy of dyslipoproteinaemia and related disorders |
JP6820717B2 (ja) | 2016-10-28 | 2021-01-27 | 株式会社日立ハイテク | プラズマ処理装置 |
CN113121417A (zh) * | 2019-12-30 | 2021-07-16 | 苏州盛迪亚生物医药有限公司 | 一种新型哌啶衍生物及其药物用途 |
WO2021192210A1 (ja) | 2020-03-27 | 2021-09-30 | 株式会社日立ハイテク | 半導体製造方法 |
Family Cites Families (18)
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ES2105920B1 (es) * | 1991-10-09 | 1998-07-01 | Syntex Inc | Procedimiento para preparar compuestos de benzo-y piridopiridazinona y piridazinationa. |
NZ257955A (en) | 1992-12-02 | 1996-05-28 | Pfizer | Catechol diethers pharmaceutical compositions |
DE19533975A1 (de) | 1995-09-14 | 1997-03-20 | Merck Patent Gmbh | Arylalkyl-diazinone |
SK283270B6 (sk) | 1997-01-15 | 2003-04-01 | Altana Pharma Ag | Ftalazinóny, farmaceutické prostriedky s ich obsahom a ich použitie |
AU1760399A (en) | 1997-12-15 | 1999-07-05 | Byk Gulden Lomberg Chemische Fabrik Gmbh | New phthalazinones |
JP2002508368A (ja) * | 1997-12-15 | 2002-03-19 | 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 | ジヒドロベンゾフラン |
EP0934933A1 (en) | 1998-02-06 | 1999-08-11 | Byk Gulden Lomberg Chemische Fabrik GmbH | Phthalazinones |
SI1070056T1 (en) * | 1998-03-14 | 2004-12-31 | Altana Pharma Ag | Phthalazinone pde iii/iv inhibitors |
WO2001019818A1 (en) | 1999-09-14 | 2001-03-22 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Phthalazinone derivatives as pd3/4 inhibitors |
TR200201128T2 (tr) | 1999-10-25 | 2002-08-21 | Byk Gulden Lomberg Chemische Fabrik Gmbh | PDE4 inhibitörleri olarak tetrahidrotiyopiranfitalazinon türevleri. |
AU781503B2 (en) * | 1999-10-25 | 2005-05-26 | Altana Pharma Ag | Phthalazinone derivatives as PDE 4 inhibitors |
WO2001094319A1 (en) | 2000-06-05 | 2001-12-13 | Altana Pharma Ag | Compounds effective as beta-2-adrenoreceptor agonists as well as pde4-inhibitors |
CZ20032491A3 (cs) * | 2001-02-15 | 2004-01-14 | Altana Pharma Ag | Ftalazinonpiperidinové deriváty |
EA200301100A1 (ru) | 2001-04-25 | 2004-06-24 | Алтана Фарма Аг | Новые фталазиноны |
PL363544A1 (en) | 2001-04-25 | 2004-11-29 | Altana Pharma Ag | Piperazino-derivatives and their use as pde4 inhibitor |
PL373146A1 (en) | 2002-08-10 | 2005-08-22 | Altana Pharma Ag | Pyridazinone-derivatives as pde4 inhibitors |
MXPA05001354A (es) | 2002-08-10 | 2005-04-28 | Altana Pharma Ag | Piperidina-ftalazonas sustituidas por pirrolidinodiona como inhibidores pde4. |
PL373597A1 (en) | 2002-08-10 | 2005-09-05 | Altana Pharma Ag | Piperidine-n-oxide-derivatives |
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2002
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- 2002-02-14 KR KR10-2003-7010552A patent/KR20030074817A/ko not_active Application Discontinuation
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2003
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2006
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EE05386B1 (et) | 2011-02-15 |
CZ20032491A3 (cs) | 2004-01-14 |
HUP0303193A2 (hu) | 2003-12-29 |
JP2004518727A (ja) | 2004-06-24 |
CA2438520A1 (en) | 2002-08-22 |
KR20030074817A (ko) | 2003-09-19 |
PL363391A1 (en) | 2004-11-15 |
US6953853B2 (en) | 2005-10-11 |
HRP20030636A2 (en) | 2005-06-30 |
EE200300311A (et) | 2003-10-15 |
SK11382003A3 (sk) | 2004-01-08 |
BR0207278A (pt) | 2004-02-10 |
US20050234062A1 (en) | 2005-10-20 |
NO20033618D0 (no) | 2003-08-14 |
CA2438520C (en) | 2011-10-04 |
BG108124A (bg) | 2004-08-31 |
HRP20030636B1 (en) | 2012-05-31 |
US7179810B2 (en) | 2007-02-20 |
CN1524080A (zh) | 2004-08-25 |
IL156812A0 (en) | 2004-02-08 |
EP1362044A1 (en) | 2003-11-19 |
US20070129373A1 (en) | 2007-06-07 |
US20040067946A1 (en) | 2004-04-08 |
MXPA03007310A (es) | 2003-12-04 |
NO325245B1 (no) | 2008-03-10 |
NO20033618L (no) | 2003-10-15 |
EA200300836A1 (ru) | 2004-02-26 |
NZ527424A (en) | 2005-02-25 |
WO2002064584A1 (en) | 2002-08-22 |
HUP0303193A3 (en) | 2007-08-28 |
AU2002234634B2 (en) | 2007-07-26 |
JP4301812B2 (ja) | 2009-07-22 |
US7531540B2 (en) | 2009-05-12 |
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