HRP20030869A2 - Piperazino-derivatives and their use as pde4 inhibitor - Google Patents
Piperazino-derivatives and their use as pde4 inhibitor Download PDFInfo
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- HRP20030869A2 HRP20030869A2 HR20030869A HRP20030869A HRP20030869A2 HR P20030869 A2 HRP20030869 A2 HR P20030869A2 HR 20030869 A HR20030869 A HR 20030869A HR P20030869 A HRP20030869 A HR P20030869A HR P20030869 A2 HRP20030869 A2 HR P20030869A2
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- Croatia
- Prior art keywords
- phenyl
- alkyl
- alkoxy
- compounds
- hydrogen
- Prior art date
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- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title description 4
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title description 4
- -1 phenylprop-1-en-3-yl Chemical group 0.000 claims description 184
- 150000001875 compounds Chemical class 0.000 claims description 139
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 39
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 35
- 125000004076 pyridyl group Chemical group 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 125000001153 fluoro group Chemical group F* 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 13
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 13
- 125000003118 aryl group Chemical group 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 9
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- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 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
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 5
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- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 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 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 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
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical group OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
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- 125000005843 halogen group Chemical group 0.000 claims 14
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- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical group C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 55
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- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 6
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Classifications
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- C07—ORGANIC CHEMISTRY
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C—CHEMISTRY; METALLURGY
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- 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
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Applications Claiming Priority (2)
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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)
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HRP20030869A2 true HRP20030869A2 (en) | 2005-08-31 |
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HR20030869A HRP20030869A2 (en) | 2001-04-25 | 2003-10-24 | Piperazino-derivatives and their use as pde4 inhibitor |
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US (1) | US7022696B2 (pl) |
EP (1) | EP1385838A1 (pl) |
JP (2) | JP4021329B2 (pl) |
KR (1) | KR20030089723A (pl) |
CN (1) | CN1505624A (pl) |
AU (1) | AU2002315311B2 (pl) |
BG (1) | BG108187A (pl) |
BR (1) | BR0209076A (pl) |
CA (1) | CA2445236A1 (pl) |
CZ (1) | CZ20033205A3 (pl) |
EA (1) | EA200301101A1 (pl) |
EE (1) | EE200300513A (pl) |
HR (1) | HRP20030869A2 (pl) |
HU (1) | HUP0303469A3 (pl) |
IL (1) | IL157870A0 (pl) |
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NZ (1) | NZ529363A (pl) |
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Families Citing this family (11)
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CZ20032491A3 (cs) | 2001-02-15 | 2004-01-14 | Altana Pharma Ag | Ftalazinonpiperidinové deriváty |
US6911452B2 (en) * | 2001-12-28 | 2005-06-28 | Acadia Pharmaceuticals Inc. | Spiroazacyclic compounds as monoamine receptor modulators |
PL373146A1 (pl) * | 2002-08-10 | 2005-08-22 | Altana Pharma Ag | Pochodne pirydazynonu jako inhibitory PDE4 |
MXPA05001354A (es) * | 2002-08-10 | 2005-04-28 | Altana Pharma Ag | Piperidina-ftalazonas sustituidas por pirrolidinodiona como inhibidores pde4. |
PL373597A1 (pl) * | 2002-08-10 | 2005-09-05 | Altana Pharma Ag | Pochodne N-tlenku piperydyny |
EP1716123A1 (en) * | 2004-02-04 | 2006-11-02 | Altana Pharma AG | Pyridazinone derivatives and their use as pde4 inhibitors |
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 |
RU2007143049A (ru) * | 2005-04-21 | 2009-05-27 | Ниппон Синяку Ко., Лтд. (Jp) | Производное фталазинона и содержащая его фармацевтическая композиция |
US7825122B2 (en) | 2005-12-14 | 2010-11-02 | 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 |
WO2013106547A1 (en) | 2012-01-10 | 2013-07-18 | 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 |
ES2105920B1 (es) | 1991-10-09 | 1998-07-01 | Syntex Inc | Procedimiento para preparar compuestos de benzo-y piridopiridazinona y piridazinationa. |
US5716954A (en) * | 1991-10-09 | 1998-02-10 | Syntex U.S.A. Inc. | Benzopyridazinone and pyridopyridazinone compounds |
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 |
DE19546918A1 (de) * | 1995-12-15 | 1997-06-19 | Bayer Ag | Bicyclische Heterocyclen |
SK283270B6 (sk) * | 1997-01-15 | 2003-04-01 | Altana Pharma Ag | Ftalazinóny, farmaceutické prostriedky s ich obsahom a ich použitie |
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 |
AU1760399A (en) * | 1997-12-15 | 1999-07-05 | Byk Gulden Lomberg Chemische Fabrik Gmbh | New phthalazinones |
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 |
AU781503B2 (en) * | 1999-10-25 | 2005-05-26 | Altana Pharma Ag | Phthalazinone derivatives as PDE 4 inhibitors |
TR200201128T2 (tr) * | 1999-10-25 | 2002-08-21 | Byk Gulden Lomberg Chemische Fabrik Gmbh | PDE4 inhibitörleri olarak tetrahidrotiyopiranfitalazinon türevleri. |
WO2001094319A1 (en) | 2000-06-05 | 2001-12-13 | Altana Pharma Ag | Compounds effective as beta-2-adrenoreceptor agonists as well as pde4-inhibitors |
EA200301100A1 (ru) * | 2001-04-25 | 2004-06-24 | Алтана Фарма Аг | Новые фталазиноны |
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BG108187A (bg) | 2004-09-30 |
US7022696B2 (en) | 2006-04-04 |
IL157870A0 (en) | 2004-03-28 |
BR0209076A (pt) | 2004-08-10 |
NZ529363A (en) | 2005-08-26 |
JP2006096766A (ja) | 2006-04-13 |
CA2445236A1 (en) | 2002-10-31 |
EP1385838A1 (en) | 2004-02-04 |
JP4021329B2 (ja) | 2007-12-12 |
EA200301101A1 (ru) | 2004-04-29 |
MXPA03009806A (es) | 2004-01-29 |
SK14352003A3 (sk) | 2004-04-06 |
EE200300513A (et) | 2004-02-16 |
CN1505624A (zh) | 2004-06-16 |
NO20034804D0 (no) | 2003-10-27 |
AU2002315311B2 (en) | 2007-12-06 |
WO2002085885A1 (en) | 2002-10-31 |
KR20030089723A (ko) | 2003-11-22 |
US20040132721A1 (en) | 2004-07-08 |
HUP0303469A2 (hu) | 2004-03-01 |
PL363544A1 (pl) | 2004-11-29 |
CZ20033205A3 (en) | 2004-03-17 |
JP2004526785A (ja) | 2004-09-02 |
ZA200308931B (en) | 2004-06-09 |
HUP0303469A3 (en) | 2004-04-28 |
NO20034804L (no) | 2003-12-29 |
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