NO318897B1 - 3-substituerte-4-arylquinolin-2-on-derivater som kaliumkanal modulatorer,anvendelse derav og farmasoytiske preparater inneholdende disse, - Google Patents

3-substituerte-4-arylquinolin-2-on-derivater som kaliumkanal modulatorer,anvendelse derav og farmasoytiske preparater inneholdende disse, Download PDF

Info

Publication number: NO318897B1
Authority: NO; Norway
Prior art keywords: trifluoromethyl; chloro; quinolinone; hydroxyphenyl; methoxyphenyl
Prior art date: 1998-12-04

Application number

NO20012739A

Other languages

English (en)

Norwegian (no)

Other versions

NO20012739L (no

NO20012739D0 (no

Inventor

John E Starrett

Piyasena Hewawasam

Original Assignee

Bristol Myers Squibb Co

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.)

1998-12-04

Filing date

2001-06-01

Publication date

2005-05-18

2001-06-01 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

2001-06-01 Publication of NO20012739L publication Critical patent/NO20012739L/no

2001-06-01 Publication of NO20012739D0 publication Critical patent/NO20012739D0/no

2005-05-18 Publication of NO318897B1 publication Critical patent/NO318897B1/no

Links

102000004257 Potassium Channel Human genes 0.000 title claims description 10
108020001213 potassium channel Proteins 0.000 title claims description 10
239000008194 pharmaceutical composition Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 134
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 71
229910052739 hydrogen Inorganic materials 0.000 claims description 24
-1 methoxy, amino Chemical group 0.000 claims description 23
239000011575 calcium Substances 0.000 claims description 19
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
239000000460 chlorine Substances 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
208000035475 disorder Diseases 0.000 claims description 14
229910052791 calcium Inorganic materials 0.000 claims description 13
231100000252 nontoxic Toxicity 0.000 claims description 13
230000003000 nontoxic effect Effects 0.000 claims description 13
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 13
229930185107 quinolinone Natural products 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
239000000825 pharmaceutical preparation Substances 0.000 claims description 10
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
201000001880 Sexual dysfunction Diseases 0.000 claims description 8
208000006011 Stroke Diseases 0.000 claims description 8
208000028867 ischemia Diseases 0.000 claims description 8
231100000872 sexual dysfunction Toxicity 0.000 claims description 8
208000030886 Traumatic Brain injury Diseases 0.000 claims description 7
230000009529 traumatic brain injury Effects 0.000 claims description 7
206010010904 Convulsion Diseases 0.000 claims description 6
208000019695 Migraine disease Diseases 0.000 claims description 6
206010046543 Urinary incontinence Diseases 0.000 claims description 6
208000006673 asthma Diseases 0.000 claims description 6
230000036461 convulsion Effects 0.000 claims description 6
208000002551 irritable bowel syndrome Diseases 0.000 claims description 6
206010027599 migraine Diseases 0.000 claims description 6
208000020431 spinal cord injury Diseases 0.000 claims description 6
QESHSZWKJULSAR-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-3-(2-hydroxyethyl)-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C12=CC(C(F)(F)F)=CC=C2NC(=O)C(CCO)=C1C1=CC(Cl)=CC=C1O QESHSZWKJULSAR-UHFFFAOYSA-N 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 5
206010015037 epilepsy Diseases 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
208000010228 Erectile Dysfunction Diseases 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
201000001881 impotence Diseases 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
ASNIIFWROCXGTM-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-3-(3-hydroxyprop-1-enyl)-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C12=CC(C(F)(F)F)=CC=C2NC(=O)C(C=CCO)=C1C1=CC(Cl)=CC=C1O ASNIIFWROCXGTM-UHFFFAOYSA-N 0.000 claims description 3
XNJYCAFGCFALEG-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-3-(3-hydroxypropyl)-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C12=CC(C(F)(F)F)=CC=C2NC(=O)C(CCCO)=C1C1=CC(Cl)=CC=C1O XNJYCAFGCFALEG-UHFFFAOYSA-N 0.000 claims description 3
QUKGHUWTRXCPOA-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-3-(4-hydroxyphenyl)-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C1=CC(O)=CC=C1C(C(NC1=CC=C(C=C11)C(F)(F)F)=O)=C1C1=CC(Cl)=CC=C1O QUKGHUWTRXCPOA-UHFFFAOYSA-N 0.000 claims description 3
FJXQSZCNFZVKCJ-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-3-(hydroxymethyl)-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C12=CC(C(F)(F)F)=CC=C2NC(=O)C(CO)=C1C1=CC(Cl)=CC=C1O FJXQSZCNFZVKCJ-UHFFFAOYSA-N 0.000 claims description 3
GIOMDNTVTJLPLS-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-3-[(4-hydroxyphenyl)methyl]-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C1=CC(O)=CC=C1CC(C(NC1=CC=C(C=C11)C(F)(F)F)=O)=C1C1=CC(Cl)=CC=C1O GIOMDNTVTJLPLS-UHFFFAOYSA-N 0.000 claims description 3
YNMNYKRICDZMSI-UHFFFAOYSA-N 4-(5-chloro-2-methoxyphenyl)-2-oxo-6-(trifluoromethyl)-1h-quinoline-3-carbaldehyde Chemical compound COC1=CC=C(Cl)C=C1C1=C(C=O)C(=O)NC2=CC=C(C(F)(F)F)C=C12 YNMNYKRICDZMSI-UHFFFAOYSA-N 0.000 claims description 3
HDBWMDUCFAXJCN-UHFFFAOYSA-N 4-(5-chloro-2-methoxyphenyl)-3-(2-hydroxyethyl)-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound COC1=CC=C(Cl)C=C1C1=C(CCO)C(=O)NC2=CC=C(C(F)(F)F)C=C12 HDBWMDUCFAXJCN-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
VXOZJABAXSOTPK-UHFFFAOYSA-N 3-(4-aminophenyl)-4-(5-chloro-2-hydroxyphenyl)-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C1=CC(N)=CC=C1C(C(NC1=CC=C(C=C11)C(F)(F)F)=O)=C1C1=CC(Cl)=CC=C1O VXOZJABAXSOTPK-UHFFFAOYSA-N 0.000 claims description 2
APGYLPLLMKZDJD-UHFFFAOYSA-N 3-(4-aminophenyl)-4-(5-chloro-2-methoxyphenyl)-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound COC1=CC=C(Cl)C=C1C(C1=CC(=CC=C1NC1=O)C(F)(F)F)=C1C1=CC=C(N)C=C1 APGYLPLLMKZDJD-UHFFFAOYSA-N 0.000 claims description 2
KFVVZDPRVILCDH-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-3-(2,4-dihydroxyphenyl)-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound OC1=CC(O)=CC=C1C(C(NC1=CC=C(C=C11)C(F)(F)F)=O)=C1C1=CC(Cl)=CC=C1O KFVVZDPRVILCDH-UHFFFAOYSA-N 0.000 claims description 2
MSBPRTWSQRWHMJ-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-3-(2-hydroxy-2-methylpropyl)-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C12=CC(C(F)(F)F)=CC=C2NC(=O)C(CC(C)(O)C)=C1C1=CC(Cl)=CC=C1O MSBPRTWSQRWHMJ-UHFFFAOYSA-N 0.000 claims description 2
OGHULWHSOGUBAH-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-3-(hydroxyiminomethyl)-6-(trifluoromethyl)-1H-quinolin-2-one Chemical compound C12=CC(C(F)(F)F)=CC=C2NC(=O)C(C=NO)=C1C1=CC(Cl)=CC=C1O OGHULWHSOGUBAH-UHFFFAOYSA-N 0.000 claims description 2
KPARSOZCXRNLDV-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-3-[2-(4-hydroxyphenyl)ethyl]-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C1=CC(O)=CC=C1CCC(C(NC1=CC=C(C=C11)C(F)(F)F)=O)=C1C1=CC(Cl)=CC=C1O KPARSOZCXRNLDV-UHFFFAOYSA-N 0.000 claims description 2
ABBYLWIDZCVZRN-UHFFFAOYSA-N 4-(5-chloro-2-hydroxyphenyl)-3-methyl-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound C12=CC(C(F)(F)F)=CC=C2NC(=O)C(C)=C1C1=CC(Cl)=CC=C1O ABBYLWIDZCVZRN-UHFFFAOYSA-N 0.000 claims description 2
QHYGEIJARKCCDK-UHFFFAOYSA-N 4-(5-chloro-2-methoxyphenyl)-3-(hydroxymethyl)-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound COC1=CC=C(Cl)C=C1C1=C(CO)C(=O)NC2=CC=C(C(F)(F)F)C=C12 QHYGEIJARKCCDK-UHFFFAOYSA-N 0.000 claims description 2
FWKLJIPHEFZMCA-UHFFFAOYSA-N COC1=CC=C(Cl)C=C1C1=C(C=NO)C(=O)NC2=CC=C(C(F)(F)F)C=C12 Chemical compound COC1=CC=C(Cl)C=C1C1=C(C=NO)C(=O)NC2=CC=C(C(F)(F)F)C=C12 FWKLJIPHEFZMCA-UHFFFAOYSA-N 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
BBQDEVQRIHLJJD-UHFFFAOYSA-N 4-(5-chloro-2-methoxyphenyl)-3-(3-hydroxyprop-1-enyl)-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound COC1=CC=C(Cl)C=C1C1=C(C=CCO)C(=O)NC2=CC=C(C(F)(F)F)C=C12 BBQDEVQRIHLJJD-UHFFFAOYSA-N 0.000 claims 2
PAIVOEWXSFIYQU-UHFFFAOYSA-N 4-(5-chloro-2-methoxyphenyl)-3-(3-hydroxypropyl)-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound COC1=CC=C(Cl)C=C1C1=C(CCCO)C(=O)NC2=CC=C(C(F)(F)F)C=C12 PAIVOEWXSFIYQU-UHFFFAOYSA-N 0.000 claims 2
ABBHQUPRQDHLMK-UHFFFAOYSA-N 4-(5-chloro-2-methoxyphenyl)-3-(4-nitrophenyl)-6-(trifluoromethyl)-1h-quinolin-2-one Chemical compound COC1=CC=C(Cl)C=C1C(C1=CC(=CC=C1NC1=O)C(F)(F)F)=C1C1=CC=C([N+]([O-])=O)C=C1 ABBHQUPRQDHLMK-UHFFFAOYSA-N 0.000 claims 1
NLHJLSVBUYNORV-UHFFFAOYSA-N 4-(5-chloro-2-methoxyphenyl)-3-(hydroxymethyl)-7-(trifluoromethyl)-1h-quinolin-2-one Chemical compound COC1=CC=C(Cl)C=C1C1=C(CO)C(=O)NC2=CC(C(F)(F)F)=CC=C12 NLHJLSVBUYNORV-UHFFFAOYSA-N 0.000 claims 1
102000005702 Calcium-Activated Potassium Channels Human genes 0.000 claims 1
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150000002431 hydrogen Chemical class 0.000 claims 1
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125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims 1
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Classifications

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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
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- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3

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NO20012739A 1998-12-04 2001-06-01 3-substituerte-4-arylquinolin-2-on-derivater som kaliumkanal modulatorer,anvendelse derav og farmasoytiske preparater inneholdende disse, NO318897B1 (no)

Applications Claiming Priority (2)

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US11107998P	1998-12-04	1998-12-04
PCT/US1999/028428 WO2000034244A1 (en)	1998-12-04	1999-12-01	3-substituted-4-arylquinolin-2-one derivatives as potassium channel modulators

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NO20012739L NO20012739L (no)	2001-06-01
NO20012739D0 NO20012739D0 (no)	2001-06-01
NO318897B1 true NO318897B1 (no)	2005-05-18

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US (1)	US6184231B1 (es)
EP (1)	EP1133474B1 (es)
JP (1)	JP2002531549A (es)
KR (1)	KR100641254B1 (es)
CN (1)	CN1129582C (es)
AR (1)	AR021867A1 (es)
AT (1)	ATE354569T1 (es)
AU (1)	AU755202B2 (es)
BR (1)	BR9915744A (es)
CO (1)	CO5150159A1 (es)
CZ (1)	CZ20011965A3 (es)
DE (1)	DE69935245T2 (es)
DK (1)	DK1133474T3 (es)
ES (1)	ES2281975T3 (es)
HU (1)	HUP0201613A3 (es)
ID (1)	ID28959A (es)
IL (1)	IL142457A (es)
MY (1)	MY115935A (es)
NO (1)	NO318897B1 (es)
NZ (1)	NZ510987A (es)
PE (1)	PE20001327A1 (es)
PL (1)	PL196955B1 (es)
PT (1)	PT1133474E (es)
RU (1)	RU2240998C2 (es)
TR (1)	TR200101339T2 (es)
TW (1)	TW495504B (es)
WO (1)	WO2000034244A1 (es)
ZA (1)	ZA200104455B (es)

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US5565472A (en)	1992-12-21	1996-10-15	Pfizer Inc.	4-aryl-3-(heteroarylureido)-1,2-dihydro-2-oxo-quinoline derivatives as antihypercholesterolemic and antiatherosclerotic agents
US5565483A (en) *	1995-06-07	1996-10-15	Bristol-Myers Squibb Company	3-substituted oxindole derivatives as potassium channel modulators
TW504504B (en)	1996-11-26	2002-10-01	Bristol Myers Squibb Co	4-aryl-3-hydroxyquinolin-2-one derivatives as ion channel modulators
EP1011677A4 (en) *	1997-08-28	2002-03-20	Bristol Myers Squibb Co	4-ARYL-3-AMINOQUINOLEIN-2-ONE DERIVATIVES AS POTASSIUM CHANNEL MODULATORS

1999
- 1999-12-01 CZ CZ20011965A patent/CZ20011965A3/cs unknown
- 1999-12-01 HU HU0201613A patent/HUP0201613A3/hu unknown
- 1999-12-01 DK DK99960636T patent/DK1133474T3/da active
- 1999-12-01 RU RU2001115714/04A patent/RU2240998C2/ru not_active IP Right Cessation
- 1999-12-01 AU AU17491/00A patent/AU755202B2/en not_active Ceased
- 1999-12-01 ID IDW00200101184A patent/ID28959A/id unknown
- 1999-12-01 JP JP2000586692A patent/JP2002531549A/ja active Pending
- 1999-12-01 BR BR9915744-6A patent/BR9915744A/pt not_active Application Discontinuation
- 1999-12-01 PT PT99960636T patent/PT1133474E/pt unknown
- 1999-12-01 DE DE69935245T patent/DE69935245T2/de not_active Expired - Lifetime
- 1999-12-01 WO PCT/US1999/028428 patent/WO2000034244A1/en not_active Ceased
- 1999-12-01 TR TR2001/01339T patent/TR200101339T2/xx unknown
- 1999-12-01 CN CN99813902A patent/CN1129582C/zh not_active Expired - Fee Related
- 1999-12-01 US US09/452,523 patent/US6184231B1/en not_active Expired - Fee Related
- 1999-12-01 PL PL348039A patent/PL196955B1/pl not_active IP Right Cessation
- 1999-12-01 KR KR1020017006938A patent/KR100641254B1/ko not_active Expired - Fee Related
- 1999-12-01 AT AT99960636T patent/ATE354569T1/de not_active IP Right Cessation
- 1999-12-01 EP EP99960636A patent/EP1133474B1/en not_active Expired - Lifetime
- 1999-12-01 CO CO99075316A patent/CO5150159A1/es unknown
- 1999-12-01 NZ NZ510987A patent/NZ510987A/xx not_active IP Right Cessation
- 1999-12-01 ES ES99960636T patent/ES2281975T3/es not_active Expired - Lifetime
- 1999-12-02 TW TW088121090A patent/TW495504B/zh not_active IP Right Cessation
- 1999-12-02 AR ARP990106137A patent/AR021867A1/es active IP Right Grant
- 1999-12-03 PE PE1999001208A patent/PE20001327A1/es not_active Application Discontinuation
- 1999-12-03 MY MYPI99005251A patent/MY115935A/en unknown
2001
- 2001-04-04 IL IL142457A patent/IL142457A/en not_active IP Right Cessation
- 2001-05-30 ZA ZA200104455A patent/ZA200104455B/en unknown
- 2001-06-01 NO NO20012739A patent/NO318897B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
KR20010087409A (ko)	2001-09-15
HUP0201613A3 (en)	2003-03-28
RU2240998C2 (ru)	2004-11-27
DE69935245T2 (de)	2007-10-31
KR100641254B1 (ko)	2006-11-02
PL196955B1 (pl)	2008-02-29
HUP0201613A2 (en)	2002-09-28
PT1133474E (pt)	2007-04-30
DE69935245D1 (de)	2007-04-05
EP1133474B1 (en)	2007-02-21
DK1133474T3 (da)	2007-04-10
CN1129582C (zh)	2003-12-03
AR021867A1 (es)	2002-08-07
ZA200104455B (en)	2002-05-30
NO20012739L (no)	2001-06-01
EP1133474A4 (en)	2005-02-16
AU755202B2 (en)	2002-12-05
ATE354569T1 (de)	2007-03-15
US6184231B1 (en)	2001-02-06
WO2000034244A1 (en)	2000-06-15
CO5150159A1 (es)	2002-04-29
ID28959A (id)	2001-07-19
PL348039A1 (en)	2002-05-06
ES2281975T3 (es)	2007-10-01
NZ510987A (en)	2004-02-27
CZ20011965A3 (cs)	2001-09-12
TW495504B (en)	2002-07-21
TR200101339T2 (tr)	2002-02-21
BR9915744A (pt)	2001-08-21
MY115935A (en)	2003-09-30
AU1749100A (en)	2000-06-26
EP1133474A1 (en)	2001-09-19
JP2002531549A (ja)	2002-09-24
IL142457A (en)	2006-10-31
NO20012739D0 (no)	2001-06-01
PE20001327A1 (es)	2001-02-01
CN1329599A (zh)	2002-01-02

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NO318897B1 (no)	2005-05-18	3-substituerte-4-arylquinolin-2-on-derivater som kaliumkanal modulatorer,anvendelse derav og farmasoytiske preparater inneholdende disse,
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JP2001511767A (ja)	2001-08-14	糖尿病薬
US5972961A (en)	1999-10-26	4-aryl-3-aminoquinoline-2-one derivatives as potassium channel modulators
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JP2006510742A (ja)	2006-03-30	高眼圧治療用眼科組成物
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JP2007504233A (ja)	2007-03-01	高眼圧の治療のための眼科用組成物
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US7145013B2 (en)	2006-12-05	3-thia-4-arylquinolin-2-one derivatives
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