ZA200308931B - Piperazino-derivatives and their use as PDE4 inhibitor. - Google Patents
Piperazino-derivatives and their use as PDE4 inhibitor. Download PDFInfo
- Publication number
- ZA200308931B ZA200308931B ZA200308931A ZA200308931A ZA200308931B ZA 200308931 B ZA200308931 B ZA 200308931B ZA 200308931 A ZA200308931 A ZA 200308931A ZA 200308931 A ZA200308931 A ZA 200308931A ZA 200308931 B ZA200308931 B ZA 200308931B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- tetrahydro
- compounds
- alkyl
- phthalazin
- Prior art date
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- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title description 5
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 116
- -1 phenylprop-1-en-3-yl Chemical group 0.000 claims description 87
- 150000003839 salts Chemical class 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 23
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000003003 spiro group Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 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 1
- 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 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- 235000013350 formula milk Nutrition 0.000 description 41
- 239000013067 intermediate product Substances 0.000 description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- 239000003814 drug 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
- 239000002253 acid Substances 0.000 description 12
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- 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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- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 4
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000000172 allergic effect Effects 0.000 description 4
- KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 description 4
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 4
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- YJRGRZJKGMBHIB-UHFFFAOYSA-N n,n-dimethyl-3-piperazin-1-ylpropan-1-amine Chemical compound CN(C)CCCN1CCNCC1 YJRGRZJKGMBHIB-UHFFFAOYSA-N 0.000 description 4
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- PCNFLKVWBDNNOW-UHFFFAOYSA-N 4-hydrazinylbenzoic acid Chemical compound NNC1=CC=C(C(O)=O)C=C1 PCNFLKVWBDNNOW-UHFFFAOYSA-N 0.000 description 3
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- Urology & Nephrology (AREA)
- Gynecology & Obstetrics (AREA)
- Ophthalmology & Optometry (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP01110227 | 2001-04-25 |
Publications (1)
Publication Number | Publication Date |
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ZA200308931B true ZA200308931B (en) | 2004-06-09 |
Family
ID=8177248
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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ZA200308931A ZA200308931B (en) | 2001-04-25 | 2003-11-17 | Piperazino-derivatives and their use as PDE4 inhibitor. |
Country Status (22)
Country | Link |
---|---|
US (1) | US7022696B2 (bg) |
EP (1) | EP1385838A1 (bg) |
JP (2) | JP4021329B2 (bg) |
KR (1) | KR20030089723A (bg) |
CN (1) | CN1505624A (bg) |
AU (1) | AU2002315311B2 (bg) |
BG (1) | BG108187A (bg) |
BR (1) | BR0209076A (bg) |
CA (1) | CA2445236A1 (bg) |
CZ (1) | CZ20033205A3 (bg) |
EA (1) | EA200301101A1 (bg) |
EE (1) | EE200300513A (bg) |
HR (1) | HRP20030869A2 (bg) |
HU (1) | HUP0303469A3 (bg) |
IL (1) | IL157870A0 (bg) |
MX (1) | MXPA03009806A (bg) |
NO (1) | NO20034804L (bg) |
NZ (1) | NZ529363A (bg) |
PL (1) | PL363544A1 (bg) |
SK (1) | SK14352003A3 (bg) |
WO (1) | WO2002085885A1 (bg) |
ZA (1) | ZA200308931B (bg) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NZ527424A (en) | 2001-02-15 | 2005-02-25 | Altana Pharma Ag | Phthalayinone-piperidino-derivatives as PDE4 inhibitors |
ATE466014T1 (de) * | 2001-12-28 | 2010-05-15 | Acadia Pharm Inc | Spiroazacyclische verbindungen als monoaminrezeptormodulatoren |
EP1542987A1 (en) * | 2002-08-10 | 2005-06-22 | ALTANA Pharma AG | Piperidine-n-oxide-derivatives |
CA2494650A1 (en) * | 2002-08-10 | 2004-03-04 | Altana Pharma Ag | Pyridazinone-derivatives as pde4 inhibitors |
AU2003260376A1 (en) * | 2002-08-10 | 2004-03-11 | Altana Pharma Ag | Piperidine-pyridazones and phthalazones as pde4 inhibitors |
WO2005075456A1 (en) * | 2004-02-04 | 2005-08-18 | Altana Pharma Ag | 2-(piperidin-4-yl) -4, 5-dihydro-2h-pyridazin-3-one derivatives as pde4 inhibitors |
EP1716123A1 (en) * | 2004-02-04 | 2006-11-02 | Altana Pharma AG | Pyridazinone derivatives and their use as pde4 inhibitors |
AU2006240730A1 (en) * | 2005-04-21 | 2006-11-02 | Nippon Shinyaku Co., Ltd. | Phthalazinone derivative and pharmaceutical comprising the same |
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 |
US20150119399A1 (en) | 2012-01-10 | 2015-04-30 | President And Fellows Of Harvard College | Beta-cell replication promoting compounds and methods of their use |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6419077A (en) * | 1987-07-13 | 1989-01-23 | Yamanouchi Pharma Co Ltd | Thiazolidine derivative |
ES2135416T3 (es) | 1991-10-09 | 1999-11-01 | Syntex Inc | Compuestos de piridopiridazinonas y piridazintionas con actividad inhibidora de la pde iv. |
US5716954A (en) | 1991-10-09 | 1998-02-10 | Syntex U.S.A. Inc. | Benzopyridazinone and pyridopyridazinone compounds |
AU673569B2 (en) | 1992-12-02 | 1996-11-14 | Pfizer Inc. | Catechol diethers as selective PDE-IV inhibitors |
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 |
AU735934B2 (en) | 1997-01-15 | 2001-07-19 | Altana Pharma Ag | Phthalazinones |
WO1999031071A1 (en) * | 1997-12-15 | 1999-06-24 | Byk Gulden Lomberg Chemische Fabrik Gmbh | New phthalazinones |
AU753576B2 (en) | 1997-12-15 | 2002-10-24 | Altana Pharma Ag | Dihydrobenzofurans |
EP0934933A1 (en) | 1998-02-06 | 1999-08-11 | Byk Gulden Lomberg Chemische Fabrik GmbH | Phthalazinones |
AU3328499A (en) | 1998-03-14 | 1999-10-11 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Phthalazinone pde iii/iv inhibitors |
AU7654200A (en) * | 1999-09-14 | 2001-04-17 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Phthalazinone derivatives as pd3/4 inhibitors |
PL354979A1 (en) | 1999-10-25 | 2004-03-22 | Altana Pharma Ag | Tetrahydrothiopy ranphthalazinone derivatives as pde4 inhibitors |
CA2388121A1 (en) * | 1999-10-25 | 2001-05-03 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Phthalazinone derivatives as pde 4 inhibitors |
SK17052002A3 (sk) | 2000-06-05 | 2003-12-02 | Altana Pharma Ag | Pyridazinónové zlúčeniny, farmaceutický prostriedok s ich obsahom a ich použitie |
CN1503792A (zh) * | 2001-04-25 | 2004-06-09 | ��̹��ҽҩ��˾ | 新的酞嗪酮 |
-
2002
- 2002-04-24 NZ NZ529363A patent/NZ529363A/en unknown
- 2002-04-24 MX MXPA03009806A patent/MXPA03009806A/es active IP Right Grant
- 2002-04-24 IL IL15787002A patent/IL157870A0/xx unknown
- 2002-04-24 BR BR0209076-7A patent/BR0209076A/pt not_active Application Discontinuation
- 2002-04-24 SK SK1435-2003A patent/SK14352003A3/sk not_active Application Discontinuation
- 2002-04-24 US US10/475,656 patent/US7022696B2/en not_active Expired - Fee Related
- 2002-04-24 HU HU0303469A patent/HUP0303469A3/hu unknown
- 2002-04-24 CZ CZ20033205A patent/CZ20033205A3/cs unknown
- 2002-04-24 WO PCT/EP2002/004494 patent/WO2002085885A1/en active IP Right Grant
- 2002-04-24 EE EEP200300513A patent/EE200300513A/xx unknown
- 2002-04-24 CA CA002445236A patent/CA2445236A1/en not_active Abandoned
- 2002-04-24 EP EP02740498A patent/EP1385838A1/en not_active Withdrawn
- 2002-04-24 AU AU2002315311A patent/AU2002315311B2/en not_active Ceased
- 2002-04-24 EA EA200301101A patent/EA200301101A1/ru unknown
- 2002-04-24 KR KR10-2003-7013849A patent/KR20030089723A/ko not_active Application Discontinuation
- 2002-04-24 CN CNA028087720A patent/CN1505624A/zh active Pending
- 2002-04-24 JP JP2002583412A patent/JP4021329B2/ja not_active Expired - Fee Related
- 2002-04-24 PL PL02363544A patent/PL363544A1/xx not_active Application Discontinuation
- 2002-09-23 BG BG108187A patent/BG108187A/bg unknown
-
2003
- 2003-10-24 HR HR20030869A patent/HRP20030869A2/hr not_active Application Discontinuation
- 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 |
---|---|
MXPA03009806A (es) | 2004-01-29 |
SK14352003A3 (sk) | 2004-04-06 |
EP1385838A1 (en) | 2004-02-04 |
NO20034804D0 (no) | 2003-10-27 |
NO20034804L (no) | 2003-12-29 |
US7022696B2 (en) | 2006-04-04 |
NZ529363A (en) | 2005-08-26 |
IL157870A0 (en) | 2004-03-28 |
HUP0303469A2 (hu) | 2004-03-01 |
HUP0303469A3 (en) | 2004-04-28 |
WO2002085885A1 (en) | 2002-10-31 |
JP4021329B2 (ja) | 2007-12-12 |
CZ20033205A3 (en) | 2004-03-17 |
BG108187A (bg) | 2004-09-30 |
HRP20030869A2 (en) | 2005-08-31 |
CN1505624A (zh) | 2004-06-16 |
PL363544A1 (en) | 2004-11-29 |
KR20030089723A (ko) | 2003-11-22 |
US20040132721A1 (en) | 2004-07-08 |
CA2445236A1 (en) | 2002-10-31 |
JP2004526785A (ja) | 2004-09-02 |
EE200300513A (et) | 2004-02-16 |
BR0209076A (pt) | 2004-08-10 |
JP2006096766A (ja) | 2006-04-13 |
EA200301101A1 (ru) | 2004-04-29 |
AU2002315311B2 (en) | 2007-12-06 |
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