NZ529221A - Phthalazinones with PDE-inhibiting properties for treatment of airway disorders and other inflammatory conditions - Google Patents
Phthalazinones with PDE-inhibiting properties for treatment of airway disorders and other inflammatory conditionsInfo
- Publication number
- NZ529221A NZ529221A NZ529221A NZ52922102A NZ529221A NZ 529221 A NZ529221 A NZ 529221A NZ 529221 A NZ529221 A NZ 529221A NZ 52922102 A NZ52922102 A NZ 52922102A NZ 529221 A NZ529221 A NZ 529221A
- Authority
- NZ
- New Zealand
- Prior art keywords
- salt
- phenyl
- solvate
- hydrate
- methoxy
- Prior art date
Links
- 238000011282 treatment Methods 0.000 title claims description 17
- 230000002401 inhibitory effect Effects 0.000 title claims description 8
- 230000004968 inflammatory condition Effects 0.000 title 1
- -1 6-methyl-3-trifluoromethyl-pyridin-2-yl Chemical group 0.000 claims abstract description 114
- 150000001875 compounds Chemical class 0.000 claims abstract description 104
- 150000003839 salts Chemical class 0.000 claims abstract description 89
- 239000012453 solvate Substances 0.000 claims abstract description 48
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- 239000000460 chlorine Chemical group 0.000 claims abstract description 19
- 229910052801 chlorine Chemical group 0.000 claims abstract description 19
- 239000005711 Benzoic acid Substances 0.000 claims abstract description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 14
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 239000011737 fluorine Substances 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims abstract description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims abstract description 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
- 229960004365 benzoic acid Drugs 0.000 claims description 15
- 101100407335 Dictyostelium discoideum pde7 gene Proteins 0.000 claims description 11
- 150000004677 hydrates Chemical class 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- 150000003254 radicals Chemical group 0.000 claims description 10
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 claims description 9
- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 claims description 9
- 230000005764 inhibitory process Effects 0.000 claims description 9
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 claims description 5
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims description 5
- 208000017520 skin disease Diseases 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
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- HZXQJGPDTRZCNX-CVEARBPZSA-N (4ar,8as)-4-(3-chloro-4-methoxyphenyl)-2-cyclopentyl-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1C1CCCC1 HZXQJGPDTRZCNX-CVEARBPZSA-N 0.000 claims description 2
- HCNFONHPDDMXQF-SJORKVTESA-N C1=C(Br)C(OC)=CC=C1C1=NN(C=2C=CC(=CC=2)C(O)=O)C(=O)[C@@H]2[C@H]1CC=CC2 Chemical compound C1=C(Br)C(OC)=CC=C1C1=NN(C=2C=CC(=CC=2)C(O)=O)C(=O)[C@@H]2[C@H]1CC=CC2 HCNFONHPDDMXQF-SJORKVTESA-N 0.000 claims description 2
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- OVMYZTUABUPBOL-YADHBBJMSA-N (4ar,8as)-4-(3-chloro-4-methoxyphenyl)-2-[1-(pyridin-4-ylmethyl)piperidin-4-yl]-4a,5,8,8a-tetrahydrophthalazin-1-one Chemical compound C1=C(Cl)C(OC)=CC=C1C([C@@H]1CC=CC[C@@H]1C1=O)=NN1C1CCN(CC=2C=CN=CC=2)CC1 OVMYZTUABUPBOL-YADHBBJMSA-N 0.000 claims 1
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- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
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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
- C07D401/14—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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—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
- 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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- C—CHEMISTRY; METALLURGY
- 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
- C07D405/02—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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- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms 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
- C07D417/02—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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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01110228 | 2001-04-25 | ||
| PCT/EP2002/004438 WO2002085906A2 (en) | 2001-04-25 | 2002-04-23 | Phthalazinones derivatives useful as pde4/7 inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ529221A true NZ529221A (en) | 2005-04-29 |
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Family Applications (1)
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| NZ529221A NZ529221A (en) | 2001-04-25 | 2002-04-23 | Phthalazinones with PDE-inhibiting properties for treatment of airway disorders and other inflammatory conditions |
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| CN (1) | CN1503792A (enExample) |
| AU (1) | AU2002317733B2 (enExample) |
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| BR (1) | BR0209149A (enExample) |
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| CZ (1) | CZ299347B6 (enExample) |
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| SK (1) | SK14342003A3 (enExample) |
| WO (1) | WO2002085906A2 (enExample) |
| ZA (1) | ZA200308930B (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20030636B1 (en) | 2001-02-15 | 2012-05-31 | Nycomed Gmbh | Phthalayinone-piperidino-derivatives as pde4 inhibitors |
| PL363544A1 (en) * | 2001-04-25 | 2004-11-29 | Altana Pharma Ag | Piperazino-derivatives and their use as pde4 inhibitor |
| WO2004018457A1 (en) * | 2002-08-10 | 2004-03-04 | Altana Pharma Ag | Pyrrolidinedione substituted piperidine-phthalazones as pde4 inhibitors |
| AU2003255376A1 (en) * | 2002-08-10 | 2004-03-11 | Altana Pharma Ag | Piperidine-derivatives as pde4 inhibitors |
| JP2005538138A (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リダジノン誘導体 |
| AU2003260371A1 (en) * | 2002-08-10 | 2004-03-11 | Altana Pharma Ag | Piperidine-n-oxide-derivatives |
| EP1716133B1 (en) * | 2004-02-04 | 2008-03-26 | Nycomed GmbH | 2-(piperidin-4-yl)-4,5-dihydro-2h-pyridazin-3-one derivatives as pde4 inhibitors |
| WO2005075437A1 (en) * | 2004-02-04 | 2005-08-18 | Altana Pharma Ag | Pyridazinone derivatives and their use as pde4 inhibitors |
| MXPA06014699A (es) * | 2004-07-05 | 2007-03-26 | Astellas Pharma Inc | Derivados de pirazolo-piridina. |
| 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 |
| ES2308916B1 (es) | 2007-03-22 | 2009-10-29 | Consejo Superior De Investigaciones Cientificas | Compuesto inhibidor dual de las enzimas pde7 y/o pde4, composiciones farmaceuticas y sus aplicaciones. |
| CN101917992A (zh) | 2007-03-27 | 2010-12-15 | 奥默罗斯公司 | 用于治疗运动障碍的pde7抑制剂的用途 |
| US8637528B2 (en) | 2007-03-27 | 2014-01-28 | Omeros Corporation | Use of PDE7 inhibitors for the treatment of movement disorders |
| CN103463086B (zh) | 2007-05-16 | 2015-10-21 | 塔科达有限责任公司 | 作为pde4抑制剂的吡唑啉酮衍生物 |
| 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. |
| ES2392488T3 (es) | 2008-11-20 | 2012-12-11 | Genentech, Inc. | Compuestos inhibidores de PI3K de tipo pirazolopiridina y sus procedimientos de uso |
| EP4275752A3 (en) | 2010-11-08 | 2024-02-21 | Omeros Corporation | Treatment of addiction and impulse-control disorders using pde7 inhibitors |
| US9220715B2 (en) | 2010-11-08 | 2015-12-29 | Omeros Corporation | Treatment of addiction and impulse-control disorders using PDE7 inhibitors |
| CA2826183C (en) | 2011-02-07 | 2019-05-14 | Scipharm Sarl | Novel composition for the treatment of cystic fibrosis |
| US20140112945A1 (en) | 2011-06-17 | 2014-04-24 | 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 |
| CN102964340B (zh) * | 2012-12-12 | 2015-10-07 | 中国药科大学 | 一类治疗阿尔茨海默病的选择性多巴胺d1受体激动剂 |
| EP2968323A4 (en) | 2013-03-13 | 2016-12-14 | Flatley Discovery Lab | PYRIDAZINONE COMPOUNDS AND METHODS FOR THE TREATMENT OF CYSTIC FIBROSIS |
| CN112876460B (zh) * | 2021-02-05 | 2022-05-31 | 山西大学 | 7-二乙胺基-3-乙酰基香豆素衍生物及其合成方法和应用 |
| CN119768172A (zh) | 2022-08-18 | 2025-04-04 | 米托迪治愈有限责任公司 | 具有磷酸二酯酶-7抑制活性的治疗剂在治疗和预防与慢性疲劳、衰竭和/或劳累不耐受有关的疾病中的用途 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993007146A1 (en) * | 1991-10-09 | 1993-04-15 | Syntex (U.S.A.) Inc. | Benzo and pyrido pyridazinone and pyridazinthione compounds with pde iv inhibiting activity |
| US5716954A (en) | 1991-10-09 | 1998-02-10 | Syntex U.S.A. Inc. | Benzopyridazinone and pyridopyridazinone compounds |
| ATE234270T1 (de) * | 1992-12-02 | 2003-03-15 | Pfizer | Cathecoldiether als selektive pde iv hemmungsmittel |
| DE19533975A1 (de) | 1995-09-14 | 1997-03-20 | Merck Patent Gmbh | Arylalkyl-diazinone |
| KR20000070150A (ko) * | 1997-01-15 | 2000-11-25 | 빅 굴덴 롬베르크 케미쉐 파브릭 게엠베하 | 프탈라지논 |
| WO1999031071A1 (en) | 1997-12-15 | 1999-06-24 | Byk Gulden Lomberg Chemische Fabrik Gmbh | New phthalazinones |
| DE69821530T2 (de) | 1997-12-15 | 2004-12-23 | Altana Pharma Ag | Dihydrobenzifurane |
| 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 |
| CA2388119A1 (en) | 1999-10-25 | 2001-05-03 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Tetrahydrothiopy ranphthalazinone derivatives as pde4 inhibitors |
| US6756371B1 (en) | 1999-10-25 | 2004-06-29 | Altana Pharma Ag | Phthalazinone derivatives as PDE4 inhibitors |
| BR0111440A (pt) | 2000-06-05 | 2003-06-03 | Altana Pharma Ag | Compostos eficazes como agonistas do (beta)2-adrenorreceptor bem como inibidores de pde4 |
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2002
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- 2002-04-23 EP EP02747291A patent/EP1385848A2/en not_active Withdrawn
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- 2002-04-23 NZ NZ529221A patent/NZ529221A/en unknown
- 2002-04-23 KR KR10-2003-7013937A patent/KR20040008162A/ko not_active Withdrawn
- 2002-04-23 SK SK1434-2003A patent/SK14342003A3/sk not_active Application Discontinuation
- 2002-04-23 CZ CZ20033206A patent/CZ299347B6/cs not_active IP Right Cessation
- 2002-04-23 HU HU0303998A patent/HUP0303998A3/hu unknown
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- 2002-04-23 IL IL15790802A patent/IL157908A0/xx unknown
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- 2003-10-27 BG BG108294A patent/BG108294A/bg unknown
- 2003-11-17 ZA ZA200308930A patent/ZA200308930B/en unknown
Also Published As
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| US7186710B2 (en) | 2007-03-06 |
| HUP0303998A3 (en) | 2007-03-28 |
| CZ299347B6 (cs) | 2008-06-25 |
| NO20034773D0 (no) | 2003-10-24 |
| SK14342003A3 (sk) | 2004-05-04 |
| CZ20033206A3 (cs) | 2004-02-18 |
| AU2002317733B2 (en) | 2007-12-13 |
| PL363312A1 (en) | 2004-11-15 |
| MXPA03009583A (es) | 2004-02-12 |
| NO20034773L (no) | 2003-12-10 |
| ZA200308930B (en) | 2004-06-09 |
| EE200300514A (et) | 2004-02-16 |
| BR0209149A (pt) | 2004-07-13 |
| US20040127707A1 (en) | 2004-07-01 |
| CA2445233A1 (en) | 2002-10-31 |
| EP1385848A2 (en) | 2004-02-04 |
| HUP0303998A2 (hu) | 2004-05-28 |
| BG108294A (bg) | 2004-09-30 |
| IL157908A0 (en) | 2004-03-28 |
| EA200301100A1 (ru) | 2004-06-24 |
| WO2002085906A2 (en) | 2002-10-31 |
| JP2004526789A (ja) | 2004-09-02 |
| HRP20030868A2 (en) | 2005-08-31 |
| WO2002085906A3 (en) | 2002-12-19 |
| CN1503792A (zh) | 2004-06-09 |
| KR20040008162A (ko) | 2004-01-28 |
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