SK5782003A3 - 3,4-Dihydroisoquinoline and isoquinoline compounds, pharmaceutical composition comprising the same and their use - Google Patents

3,4-Dihydroisoquinoline and isoquinoline compounds, pharmaceutical composition comprising the same and their use Download PDF

Info

Publication number: SK5782003A3
Authority: SK; Slovakia
Prior art keywords: chloro; dihydroisoquinoline; hydrogen; phenyl; found
Prior art date: 2000-11-14

Application number

SK578-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Steffen Weinbrenner

Beate Schmidt

Gerhard Grundler

Josef Stadlwieser

Armin Hatzelmann

Wolfram Steinhilber

Daniela Bundschuh

Hans-Peter Kley

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.)

2000-11-14

Filing date

2001-11-08

Publication date

2003-10-07

2001-11-08 Application filed by Altana Pharma Ag filed Critical Altana Pharma Ag

2003-10-07 Publication of SK5782003A3 publication Critical patent/SK5782003A3/sk

Links

NKSZCPBUWGZONP-UHFFFAOYSA-N 3,4-dihydroisoquinoline Chemical compound C1=CC=C2C=NCCC2=C1 NKSZCPBUWGZONP-UHFFFAOYSA-N 0.000 title claims abstract description 19
239000008194 pharmaceutical composition Substances 0.000 title claims description 9
125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
-1 nitro, amino, carboxyl Chemical group 0.000 claims description 215
229910052739 hydrogen Inorganic materials 0.000 claims description 73
239000001257 hydrogen Substances 0.000 claims description 73
150000001875 compounds Chemical class 0.000 claims description 70
150000002431 hydrogen Chemical class 0.000 claims description 58
150000003839 salts Chemical class 0.000 claims description 41
125000001153 fluoro group Chemical group F* 0.000 claims description 33
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
125000001309 chloro group Chemical group Cl* 0.000 claims description 29
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 28
125000004093 cyano group Chemical group *C#N 0.000 claims description 27
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 21
125000001246 bromo group Chemical group Br* 0.000 claims description 16
239000003814 drug Substances 0.000 claims description 15
229910052731 fluorine Inorganic materials 0.000 claims description 15
239000011737 fluorine Substances 0.000 claims description 15
150000002537 isoquinolines Chemical class 0.000 claims description 15
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 13
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
239000000460 chlorine Substances 0.000 claims description 10
125000001624 naphthyl group Chemical group 0.000 claims description 10
229930192474 thiophene Natural products 0.000 claims description 10
201000010099 disease Diseases 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
125000000842 isoxazolyl group Chemical group 0.000 claims description 9
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 9
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 8
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 8
125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 8
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
230000005764 inhibitory process Effects 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
208000018569 Respiratory Tract disease Diseases 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 3
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125000004799 bromophenyl group Chemical group 0.000 claims 1
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229910052740 iodine Inorganic materials 0.000 abstract description 2
229940123304 Phosphodiesterase 7 inhibitor Drugs 0.000 abstract 1
239000002606 phosphodiesterase VII inhibitor Substances 0.000 abstract 1
238000004128 high performance liquid chromatography Methods 0.000 description 238
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 38
238000005481 NMR spectroscopy Methods 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
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238000000034 method Methods 0.000 description 16
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CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 12
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
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238000002821 scintillation proximity assay Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
230000010933 acylation Effects 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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101100441092 Danio rerio crlf3 gene Proteins 0.000 description 3
241000238631 Hexapoda Species 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
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101000909851 Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) cAMP/cGMP dual specificity phosphodiesterase Rv0805 Proteins 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000003556 assay Methods 0.000 description 3
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229940098773 bovine serum albumin Drugs 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 3
230000006806 disease prevention Effects 0.000 description 3
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JVCYUMGWRUUOCN-UHFFFAOYSA-N n-[4-(7-chloro-3,4-dihydroisoquinolin-1-yl)-2-methoxyphenyl]-4-(trifluoromethoxy)benzenesulfonamide Chemical compound COC1=CC(C=2C3=CC(Cl)=CC=C3CCN=2)=CC=C1NS(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 JVCYUMGWRUUOCN-UHFFFAOYSA-N 0.000 description 3
239000002674 ointment Substances 0.000 description 3
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DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
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239000007858 starting material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 2
HRZIQUKKHKMNMF-UHFFFAOYSA-N 2-chloro-4-fluoro-n-[4-[6-(trifluoromethyl)-3,4-dihydroisoquinolin-1-yl]phenyl]benzenesulfonamide Chemical compound ClC1=CC(F)=CC=C1S(=O)(=O)NC1=CC=C(C=2C3=CC=C(C=C3CCN=2)C(F)(F)F)C=C1 HRZIQUKKHKMNMF-UHFFFAOYSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
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- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
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- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

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SK578-2003A 2000-11-14 2001-11-08 3,4-Dihydroisoquinoline and isoquinoline compounds, pharmaceutical composition comprising the same and their use SK5782003A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP00124774		2000-11-14
DE10103547		2001-01-26
PCT/EP2001/012918 WO2002040450A1 (en)	2000-11-14	2001-11-08	(dihydro)isoquinoline derivatives as phosphodiesterase inhibitors

Publications (1)

Publication Number	Publication Date
SK5782003A3 true SK5782003A3 (en)	2003-10-07

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ID=26008337

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SK578-2003A SK5782003A3 (en)	2000-11-14	2001-11-08	3,4-Dihydroisoquinoline and isoquinoline compounds, pharmaceutical composition comprising the same and their use

Country Status (16)

Country	Link
US (1)	US6818651B2 (cs)
EP (1)	EP1337515A1 (cs)
JP (1)	JP2004513938A (cs)
KR (1)	KR20030045184A (cs)
CN (1)	CN1474812A (cs)
AU (2)	AU2002229541B2 (cs)
BR (1)	BR0115318A (cs)
CA (1)	CA2428527A1 (cs)
CZ (1)	CZ20031334A3 (cs)
HU (1)	HUP0400011A3 (cs)
IL (1)	IL155067A0 (cs)
MX (1)	MXPA03004262A (cs)
NZ (1)	NZ525147A (cs)
PL (1)	PL361144A1 (cs)
SK (1)	SK5782003A3 (cs)
WO (1)	WO2002040450A1 (cs)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2004044235A1 (en) *	2002-11-13	2004-05-27	Bayer Healthcare Ag	DIAGNOSTICS AND THERAPEUTICS FOR DISEASES ASSOCIATED WITH HUMAN PHOSPHODIESTERASE 7A1 (PDE7a1)
JP2006219374A (ja)	2003-06-13	2006-08-24	Daiichi Asubio Pharma Co Ltd	Ｐｄｅ７阻害作用を有するイミダゾトリアジノン誘導体
JP2006219373A (ja)	2003-06-13	2006-08-24	Daiichi Asubio Pharma Co Ltd	Ｐｄｅ７阻害作用を有するピリジニルピラゾロピリミジノン誘導体
WO2006004040A1 (ja)	2004-07-01	2006-01-12	Daiichi Asubio Pharma Co., Ltd.	Ｐｄｅ７阻害作用を有するチエノピラゾール誘導体
EP2275095A3 (en)	2005-08-26	2011-08-17	Braincells, Inc.	Neurogenesis by muscarinic receptor modulation
EP2258358A3 (en)	2005-08-26	2011-09-07	Braincells, Inc.	Neurogenesis with acetylcholinesterase inhibitor
EP1940389A2 (en)	2005-10-21	2008-07-09	Braincells, Inc.	Modulation of neurogenesis by pde inhibition
AU2006308889A1 (en)	2005-10-31	2007-05-10	Braincells, Inc.	GABA receptor mediated modulation of neurogenesis
WO2007067946A2 (en) *	2005-12-07	2007-06-14	The Regents Of The University Of California	Diagnosis and treatment of chronic lymphocytic leukemia (cll)
US20100216734A1 (en)	2006-03-08	2010-08-26	Braincells, Inc.	Modulation of neurogenesis by nootropic agents
DE102006012544A1 (de)	2006-03-18	2007-09-27	Sanofi-Aventis	Substituierte 1-Amino 4-phenyl-dihydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament
JP2009536667A (ja)	2006-05-09	2009-10-15	ブレインセルス，インコーポレイティド	５ｈｔ受容体介在性の神経新生
EP2382975A3 (en)	2006-05-09	2012-02-29	Braincells, Inc.	Neurogenesis by modulating angiotensin
AU2007292848A1 (en) *	2006-09-08	2008-03-13	Braincells, Inc.	Combinations containing a 4-acylaminopyridine derivative
US20100184806A1 (en)	2006-09-19	2010-07-22	Braincells, Inc.	Modulation of neurogenesis by ppar agents
JP5580192B2 (ja) *	2007-03-27	2014-08-27	オメロスコーポレーション	運動障害の処置のためのｐｄｅ７インヒビターの使用
US8637528B2 (en)	2007-03-27	2014-01-28	Omeros Corporation	Use of PDE7 inhibitors for the treatment of movement disorders
WO2010099217A1 (en)	2009-02-25	2010-09-02	Braincells, Inc.	Modulation of neurogenesis using d-cycloserine combinations
CZ302637B6 (cs) *	2010-01-05	2011-08-10	Zentiva, K. S	Zpusob prípravy 6,7-dimethoxy-1-[2-(4-trifluormethylfenyl)ethyl]-3,4-dihydroisochinolinu
US9220715B2 (en)	2010-11-08	2015-12-29	Omeros Corporation	Treatment of addiction and impulse-control disorders using PDE7 inhibitors
CN106038567A (zh)	2010-11-08	2016-10-26	奥默罗斯公司	使用pde7抑制剂治疗成瘾和冲动控制障碍
WO2013106547A1 (en)	2012-01-10	2013-07-18	President And Fellows Of Harvard College	Beta-cell replication promoting compounds and methods of their use
US20260048059A1 (en)	2022-08-18	2026-02-19	Klaus Wirth	Use of substituted benzoxazole and benzofuran compounds for the treatment and prevention of diseases associated with chronic fatigue, exhaustion and/or exertional intoleranc

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4863870A (en)	1988-03-10	1989-09-05	Bio-Affinity Systems, Inc.	Method of thioacylation peptide sequencing with alcoholysis of thiazolinones
GB9027055D0 (en)	1990-12-13	1991-02-06	Sandoz Ltd	Organic compounds
GB9222253D0 (en)	1992-10-23	1992-12-09	Celltech Ltd	Chemical compounds
GB9322828D0 (en)	1993-11-05	1993-12-22	Sandoz Ltd	Organic compounds
WO1998021207A1 (de)	1996-11-12	1998-05-22	Byk Gulden Lomberg Chemische Fabrik Gmbh	(2,3-dihydrobenzofuranyl)-thiazole als phosphodiesterasehemmer
ES2193539T3 (es)	1997-06-03	2003-11-01	Altana Pharma Ag	Benzonaftiridinas.
AU2790999A (en) *	1998-03-03	1999-09-20	Merck & Co., Inc.	Fused piperidine substituted arylsulfonamides as beta3-agonists

2001
- 2001-11-08 CZ CZ20031334A patent/CZ20031334A3/cs unknown
- 2001-11-08 MX MXPA03004262A patent/MXPA03004262A/es unknown
- 2001-11-08 BR BR0115318-8A patent/BR0115318A/pt not_active IP Right Cessation
- 2001-11-08 JP JP2002542778A patent/JP2004513938A/ja not_active Ceased
- 2001-11-08 EP EP01990399A patent/EP1337515A1/en not_active Withdrawn
- 2001-11-08 HU HU0400011A patent/HUP0400011A3/hu unknown
- 2001-11-08 CN CNA018187641A patent/CN1474812A/zh active Pending
- 2001-11-08 KR KR10-2003-7006381A patent/KR20030045184A/ko not_active Withdrawn
- 2001-11-08 US US10/381,461 patent/US6818651B2/en not_active Expired - Fee Related
- 2001-11-08 IL IL15506701A patent/IL155067A0/xx unknown
- 2001-11-08 NZ NZ525147A patent/NZ525147A/en unknown
- 2001-11-08 WO PCT/EP2001/012918 patent/WO2002040450A1/en not_active Ceased
- 2001-11-08 AU AU2002229541A patent/AU2002229541B2/en not_active Ceased
- 2001-11-08 AU AU2954102A patent/AU2954102A/xx active Pending
- 2001-11-08 PL PL01361144A patent/PL361144A1/xx unknown
- 2001-11-08 SK SK578-2003A patent/SK5782003A3/sk unknown
- 2001-11-08 CA CA002428527A patent/CA2428527A1/en not_active Abandoned

Also Published As

Publication number	Publication date
MXPA03004262A (es)	2003-09-22
WO2002040450A1 (en)	2002-05-23
JP2004513938A (ja)	2004-05-13
HUP0400011A3 (en)	2008-03-28
CA2428527A1 (en)	2002-05-23
NZ525147A (en)	2004-10-29
CZ20031334A3 (cs)	2003-09-17
HUP0400011A2 (hu)	2004-05-28
AU2002229541B2 (en)	2007-01-18
AU2954102A (en)	2002-05-27
PL361144A1 (en)	2004-09-20
KR20030045184A (ko)	2003-06-09
IL155067A0 (en)	2003-10-31
US20040044212A1 (en)	2004-03-04
US6818651B2 (en)	2004-11-16
EP1337515A1 (en)	2003-08-27
BR0115318A (pt)	2004-02-03
CN1474812A (zh)	2004-02-11

Publication	Publication Date	Title
SK5782003A3 (en)	2003-10-07	3,4-Dihydroisoquinoline and isoquinoline compounds, pharmaceutical composition comprising the same and their use
AU596611B2 (en)	1990-05-10	New quinazoline derivatives and a process for their production
ES2236701T3 (es)	2005-07-16	Compuestos de aril- y heteroaril-quinazolina que inhiben la actividad tirosina quinasa del receptor csf-1r.
JP3081172B2 (ja)	2000-08-28	含窒素複素環化合物
AU2002229541A1 (en)	2002-08-01	(dihydro)isoquinoline derivatives as phosphodiesterase inhibitors
JP4234344B2 (ja)	2009-03-04	スルホンアミド含有複素環化合物
CN101622234B (zh)	2013-08-07	适于治疗炎性或变应性病症的二环有机化合物
CN101103033B (zh)	2010-08-04	作为pde2抑制剂的三唑并酞嗪
EP0318225B1 (en)	1994-03-16	6-Aryl aminomethyl quinoline derivatives and their use as anti-tumour agents
NZ231588A (en)	1992-03-26	Quinazoline-4-one derivatives, medicaments
AU3966493A (en)	1993-11-08	Antiproliferative quinazolines
EP0459730A2 (en)	1991-12-04	Anti-tumour compounds
JP2005502662A (ja)	2005-01-27	ホスホジエステラーゼ阻害剤としての１−アルキルまたは１−シクロアルキルトリアゾロ［４，３−ａ］キナゾリン−５−オン類
EP3968991B1 (en)	2024-07-31	Protein kinase inhibitors and uses thereof for the treatment of diseases and conditions
US11447501B2 (en)	2022-09-20	Biphenyl-containing diarylpyrimido compounds, pharmaceutically-acceptable salts thereof, composition and preparation thereof
WO2010066111A1 (zh)	2010-06-17	一类含有嘧啶酮苯基的化合物、其药物组合物及其制备方法和用途
AU8545091A (en)	1992-04-15	Antiproliferative substituted naphthalene compounds
WO2006127379A2 (en)	2006-11-30	Par2-modulating compounds and their use
US11174255B2 (en)	2021-11-16	Pyrido[2,3-d]pyrimidin-7-ones and related compounds as inhibitors of protein kinases
EP0365763A1 (en)	1990-05-02	Antiproliferative cyclic compounds
Costi et al.	2000	Structure-activity relationship studies on potential non-nucleoside DABO-like inhibitors of HIV-1 reverse transcriptase
WO2002040449A1 (en)	2002-05-23	Dihydroisoquinolines as novel phosphodiesterase inhibitors
Jyothsna et al.	2024	Pyrazole-quinazoline hybrids as potent antimicrobial and anthelmintic activity: design, synthesis, characterization
JPH0227345B2 (cs)	1990-06-15
ZA200302759B (en)	2004-04-23	(Dihydro)isoquinoline derivatives as phosphodiesterase inhibitors.