SK14352003A3 - Piperazino-deriváty, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents

Piperazino-deriváty, farmaceutický prostriedok s ich obsahom a ich použitie Download PDF

Info

Publication number: SK14352003A3
Authority: SK; Slovakia
Prior art keywords: phenyl; alkyl; alkoxy; hydrogen; general formula
Prior art date: 2001-04-25

Application number

SK1435-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Armin Hatzelmann

Daniela Bundschuh

Johannes Barsig

Hans-Peter Kley

Gerhard Grundler

Beate Schmidt

Geert Jan Sterk

Original Assignee

Altana Pharma Ag

Priority date (The priority date 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 date listed.)

2001-04-25

Filing date

2002-04-24

Publication date

2004-04-06

2002-04-24 Application filed by Altana Pharma Ag filed Critical Altana Pharma Ag

2004-04-06 Publication of SK14352003A3 publication Critical patent/SK14352003A3/sk

Links

229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title abstract description 5
239000002587 phosphodiesterase IV inhibitor Substances 0.000 title abstract description 5
150000001875 compounds Chemical class 0.000 claims abstract description 124
-1 Piperazino Chemical class 0.000 claims description 277
229910052739 hydrogen Inorganic materials 0.000 claims description 40
239000001257 hydrogen Substances 0.000 claims description 40
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
150000003839 salts Chemical class 0.000 claims description 36
125000004076 pyridyl group Chemical group 0.000 claims description 30
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 27
150000002431 hydrogen Chemical class 0.000 claims description 27
229910052736 halogen Inorganic materials 0.000 claims description 25
150000002367 halogens Chemical class 0.000 claims description 23
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 18
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
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
201000010099 disease Diseases 0.000 claims description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
238000011282 treatment Methods 0.000 claims description 13
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 12
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 12
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 12
125000001072 heteroaryl group Chemical group 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
239000003814 drug Substances 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 10
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 9
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 9
125000003003 spiro group Chemical group 0.000 claims description 8
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 6
125000001041 indolyl group Chemical group 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
150000002430 hydrocarbons Chemical group 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 4
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
150000004885 piperazines Chemical class 0.000 claims description 3
208000023504 respiratory system disease Diseases 0.000 claims description 2
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 claims description 2
JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical compound C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-UHFFFAOYSA-N 0.000 claims 2
125000005843 halogen group Chemical group 0.000 claims 2
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 2
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 abstract description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
239000000543 intermediate Substances 0.000 description 39
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
239000000243 solution Substances 0.000 description 19
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239000000203 mixture Substances 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
230000000694 effects Effects 0.000 description 12
238000000034 method Methods 0.000 description 12
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 11
239000002904 solvent Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
239000012458 free base Substances 0.000 description 10
239000000546 pharmaceutical excipient Substances 0.000 description 9
239000002253 acid Substances 0.000 description 7
150000001555 benzenes Chemical class 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
239000007858 starting material Substances 0.000 description 7
NGZFTPGHJJBJHZ-UHFFFAOYSA-N 4a,5,8,8a-tetrahydro-2h-phthalazin-1-one Chemical compound C1C=CCC2C(=O)NN=CC21 NGZFTPGHJJBJHZ-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
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KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 4
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HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
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Classifications

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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
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- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/02—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 two hetero rings
- C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D417/02—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 two hetero rings
- C07D417/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond

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SK1435-2003A 2001-04-25 2002-04-24 Piperazino-deriváty, farmaceutický prostriedok s ich obsahom a ich použitie SK14352003A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP01110227		2001-04-25
PCT/EP2002/004494 WO2002085885A1 (en)	2001-04-25	2002-04-24	Piperazino-derivatives and their use as pde4 inhibitor

Publications (1)

Publication Number	Publication Date
SK14352003A3 true SK14352003A3 (sk)	2004-04-06

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ID=8177248

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1435-2003A SK14352003A3 (sk)	2001-04-25	2002-04-24	Piperazino-deriváty, farmaceutický prostriedok s ich obsahom a ich použitie

Country Status (22)

Country	Link
US (1)	US7022696B2 (ru)
EP (1)	EP1385838A1 (ru)
JP (2)	JP4021329B2 (ru)
KR (1)	KR20030089723A (ru)
CN (1)	CN1505624A (ru)
AU (1)	AU2002315311B2 (ru)
BG (1)	BG108187A (ru)
BR (1)	BR0209076A (ru)
CA (1)	CA2445236A1 (ru)
CZ (1)	CZ20033205A3 (ru)
EA (1)	EA200301101A1 (ru)
EE (1)	EE200300513A (ru)
HR (1)	HRP20030869A2 (ru)
HU (1)	HUP0303469A3 (ru)
IL (1)	IL157870A0 (ru)
MX (1)	MXPA03009806A (ru)
NO (1)	NO20034804L (ru)
NZ (1)	NZ529363A (ru)
PL (1)	PL363544A1 (ru)
SK (1)	SK14352003A3 (ru)
WO (1)	WO2002085885A1 (ru)
ZA (1)	ZA200308931B (ru)

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HRP20030636B1 (en)	2001-02-15	2012-05-31	Nycomed Gmbh	Phthalayinone-piperidino-derivatives as pde4 inhibitors
KR100974901B1 (ko) *	2001-12-28	2010-08-10	아카디아 파마슈티칼스 인코포레이티드	모노아민 수용체 조정자로서의 스피로아자사이클릭 화합물
CA2494650A1 (en) *	2002-08-10	2004-03-04	Altana Pharma Ag	Pyridazinone-derivatives as pde4 inhibitors
HRP20050197A2 (en) *	2002-08-10	2006-06-30	Altana Pharma Ag	Piperidine-n-oxide-derivatives
JP2005538140A (ja) *	2002-08-10	2005-12-15	アルタナ　ファルマ　アクチエンゲゼルシャフト	Ｐｄｅ４インヒビターとしてのピペリジン−ピリダゾン及びフタラゾン
US20080227790A1 (en) *	2004-02-04	2008-09-18	Altana Pharma Ag	Pyridazinone Derivatives and their Use as Pde4 Inhibitors
AU2005210042B2 (en)	2004-02-04	2011-04-21	Takeda Gmbh	2-(piperidin-4-yl) -4, 5-dihydro-2H-pyridazin-3-one derivatives as PDE4 inhibitors
CN101163681A (zh) *	2005-04-21	2008-04-16	日本新药株式会社	2,3-二氮杂萘酮衍生物及其医药品
WO2007070506A2 (en)	2005-12-14	2007-06-21	Amgen Inc.	Diaza heterocyclic sulfonamide derivatives and their uses
KR100843352B1 (ko) *	2007-01-30	2008-07-03	한국과학기술연구원	세로토닌 수용체 5-ＨＴ2ａ 또는 5-ＨＴ2ｃ의 길항제로활성을 갖는 1,2-다이하이드로-1-옥소프탈라지닐 피페라진화합물 및 이의 제조방법
EP2804603A1 (en)	2012-01-10	2014-11-26	President and Fellows of Harvard College	Beta-cell replication promoting compounds and methods of their use

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JPS6419077A (en) *	1987-07-13	1989-01-23	Yamanouchi Pharma Co Ltd	Thiazolidine derivative
US5716954A (en)	1991-10-09	1998-02-10	Syntex U.S.A. Inc.	Benzopyridazinone and pyridopyridazinone compounds
JP3245165B2 (ja)	1991-10-09	2002-01-07	シンテックス（ユー・エス・エイ）・インコーポレイテッド	ピリドピリダジノンおよびピリダジンチオン化合物
BR9307570A (pt)	1992-12-02	1999-05-25	Pfizer	Diéteres de catecol como inibidores seletivos de pdeiv
DE19533975A1 (de)	1995-09-14	1997-03-20	Merck Patent Gmbh	Arylalkyl-diazinone
DE19546918A1 (de) *	1995-12-15	1997-06-19	Bayer Ag	Bicyclische Heterocyclen
ES2193508T3 (es)	1997-01-15	2003-11-01	Altana Pharma Ag	Ftalizinonas.
AU1760399A (en) *	1997-12-15	1999-07-05	Byk Gulden Lomberg Chemische Fabrik Gmbh	New phthalazinones
ATE258930T1 (de)	1997-12-15	2004-02-15	Altana Pharma Ag	Dihydrobenzifurane
EP0934933A1 (en)	1998-02-06	1999-08-11	Byk Gulden Lomberg Chemische Fabrik GmbH	Phthalazinones
DK1070056T3 (da)	1998-03-14	2004-11-08	Altana Pharma Ag	Phthalazinon-PDE III/IV-inhibitorer
WO2001019818A1 (en)	1999-09-14	2001-03-22	Byk Gulden Lomberg Chemische Fabrik Gmbh	Phthalazinone derivatives as pd3/4 inhibitors
HUP0203487A2 (hu)	1999-10-25	2003-02-28	Byk Gulden Lomberg Chemische Fabrik Gmbh	Tetrahidrotiopirán-ftalazinon-származékok, mint PDE4-inhibitorok és ezeket tartalmazó gyógyszerkészítmények
EP1228046B1 (en) *	1999-10-25	2007-09-26	Nycomed GmbH	Phthalazinone derivatives as pde 4 inhibitors
CZ20023997A3 (cs)	2000-06-05	2003-05-14	Altana Pharma Ag	Pyridazinonové deriváty
EE200300514A (et) *	2001-04-25	2004-02-16	Altana Pharma Ag	Ftalasinoonid, nende kasutamine hingamisteede haigusnähte leevendavate ravimite valmistamiseks ningneid sisaldavad ravimid

2002
- 2002-04-24 JP JP2002583412A patent/JP4021329B2/ja not_active Expired - Fee Related
- 2002-04-24 MX MXPA03009806A patent/MXPA03009806A/es active IP Right Grant
- 2002-04-24 NZ NZ529363A patent/NZ529363A/en unknown
- 2002-04-24 AU AU2002315311A patent/AU2002315311B2/en not_active Ceased
- 2002-04-24 SK SK1435-2003A patent/SK14352003A3/sk not_active Application Discontinuation
- 2002-04-24 HR HR20030869A patent/HRP20030869A2/hr not_active Application Discontinuation
- 2002-04-24 CN CNA028087720A patent/CN1505624A/zh active Pending
- 2002-04-24 WO PCT/EP2002/004494 patent/WO2002085885A1/en not_active Ceased
- 2002-04-24 EP EP02740498A patent/EP1385838A1/en not_active Withdrawn
- 2002-04-24 EA EA200301101A patent/EA200301101A1/ru unknown
- 2002-04-24 KR KR10-2003-7013849A patent/KR20030089723A/ko not_active Ceased
- 2002-04-24 IL IL15787002A patent/IL157870A0/xx unknown
- 2002-04-24 HU HU0303469A patent/HUP0303469A3/hu unknown
- 2002-04-24 CA CA002445236A patent/CA2445236A1/en not_active Abandoned
- 2002-04-24 US US10/475,656 patent/US7022696B2/en not_active Expired - Fee Related
- 2002-04-24 BR BR0209076-7A patent/BR0209076A/pt not_active Application Discontinuation
- 2002-04-24 EE EEP200300513A patent/EE200300513A/xx unknown
- 2002-04-24 CZ CZ20033205A patent/CZ20033205A3/cs unknown
- 2002-04-24 PL PL02363544A patent/PL363544A1/xx not_active Application Discontinuation
- 2002-09-23 BG BG108187A patent/BG108187A/bg unknown
2003
- 2003-10-27 NO NO20034804A patent/NO20034804L/no unknown
- 2003-11-17 ZA ZA200308931A patent/ZA200308931B/en unknown
2005
- 2005-11-21 JP JP2005336182A patent/JP2006096766A/ja not_active Withdrawn

Also Published As

Publication number	Publication date
AU2002315311B2 (en)	2007-12-06
BR0209076A (pt)	2004-08-10
PL363544A1 (en)	2004-11-29
ZA200308931B (en)	2004-06-09
JP2006096766A (ja)	2006-04-13
JP4021329B2 (ja)	2007-12-12
EA200301101A1 (ru)	2004-04-29
CZ20033205A3 (en)	2004-03-17
JP2004526785A (ja)	2004-09-02
HRP20030869A2 (en)	2005-08-31
CA2445236A1 (en)	2002-10-31
WO2002085885A1 (en)	2002-10-31
EE200300513A (et)	2004-02-16
KR20030089723A (ko)	2003-11-22
EP1385838A1 (en)	2004-02-04
NO20034804D0 (no)	2003-10-27
IL157870A0 (en)	2004-03-28
CN1505624A (zh)	2004-06-16
NO20034804L (no)	2003-12-29
US7022696B2 (en)	2006-04-04
HUP0303469A2 (hu)	2004-03-01
HUP0303469A3 (en)	2004-04-28
US20040132721A1 (en)	2004-07-08
BG108187A (bg)	2004-09-30
NZ529363A (en)	2005-08-26
MXPA03009806A (es)	2004-01-29

Legal Events

Date	Code	Title	Description
2010-08-09	FC9A	Refused patent application

Publication	Publication Date	Title
JP4555684B2 (ja)	2010-10-06	Ｐｄｅ４阻害剤としての、ピロリジンジオンにより置換されたピペリジン−フタラゾン
JP4301812B2 (ja)	2009-07-22	Ｐｄｅ４インヒビターとしてのフタラインオン−ピペリジノ−誘導体
US20060166995A1 (en)	2006-07-27	Piperidine-n-oxide-derivatives
JP2005538138A (ja)	2005-12-15	Ｐｄｅ４インヒビターとしてのピリダジノン誘導体
WO2004018449A1 (en)	2004-03-04	Piperidine-derivatives as pde4 inhibitors
AU2002234634A1 (en)	2003-02-20	Phthalayinone-piperidino-derivatives as PDE4 inhibitors
US20030166655A1 (en)	2003-09-04	Tetrahydrothiopy ranphthalazinone derivatives as PDE4 inhibitors
US7022696B2 (en)	2006-04-04	Piperazino-derivatives and their use as PDE4 inhibitor
AU781503B2 (en)	2005-05-26	Phthalazinone derivatives as PDE 4 inhibitors
AU2002315311A1 (en)	2003-04-17	Piperazino-derivatives and their use as PDE4 inhibitor
EP1720854A1 (en)	2006-11-15	Phthalzinone derivatives as pde4 inhibitors
WO2005075437A1 (en)	2005-08-18	Pyridazinone derivatives and their use as pde4 inhibitors