WO1998004521B1 - Potassium channel inhibitors - Google Patents
Potassium channel inhibitorsInfo
- Publication number
- WO1998004521B1 WO1998004521B1 PCT/US1997/012559 US9712559W WO9804521B1 WO 1998004521 B1 WO1998004521 B1 WO 1998004521B1 US 9712559 W US9712559 W US 9712559W WO 9804521 B1 WO9804521 B1 WO 9804521B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- optionally substituted
- alkyl
- methyl
- group
- carbocycloalkyl
- Prior art date
Links
- 230000002401 inhibitory effect Effects 0.000 title claims abstract 3
- 102000004257 potassium channel family Human genes 0.000 title claims abstract 3
- 108020001213 potassium channel family Proteins 0.000 title claims abstract 3
- 239000003112 inhibitor Substances 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 8
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 7
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 6
- 239000001257 hydrogen Substances 0.000 claims abstract 6
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims abstract 6
- 150000001875 compounds Chemical class 0.000 claims abstract 5
- 239000000651 prodrug Substances 0.000 claims abstract 5
- 229940002612 prodrugs Drugs 0.000 claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 239000011780 sodium chloride Substances 0.000 claims abstract 5
- 150000002500 ions Chemical class 0.000 claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- -1 β-naphthyl Chemical group 0.000 claims 1
- 206010007521 Cardiac arrhythmias Diseases 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 235000019256 formaldehyde Nutrition 0.000 abstract 1
- 230000002062 proliferating Effects 0.000 abstract 1
Abstract
Compounds of general formula (I) wherein R1 is H, alkyl or is selected from the group consisting of an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted heterocyclyl and an optionally substituted carbocycloalkyl; R2 is selected from the group consisting of alkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted heterocyclyl and an optionally substituted carbocycloalkyl; R3 is hydrogen or methyl; R4 is hydrogen or methyl; X1 is C=O, C=S, or SO¿2; X?2 is C=O or SO¿2; Y?1 is O, (CH¿2?)p, CH2O, HC=CH or NH; wherein p is 0, 1 or 2; Y?2¿ is O, (CH¿2?)q, HC=CH or NH; wherein q is 0 or 1; Z is H, OR?5 or NR6R7¿; wherein R5 is H, (CH¿2)m-R?8; or C(O)-(CH¿2)m-R?8; m = 1 to 5; R?8 is N(R9)¿2, N(R9)3L or CO2R9; wherein each R9 is independently selected from H or alkyl; and L is a counter ion; R6 is H or alkyl; R7 is H, alkyl or CO¿2R?10; wherein R10 is alkyl; or pharmaceutically acceptable salts or prodrugs thereof are useful as potassium channel inhibitors and useful for the treatment of cardiac arrhythmias and cell proliferative disorders.
Claims
AMENDED CLAIMS
[received by the International Bureau on 9 February 1998 (09.02.98); original claims 1 and 5 amended; remaining claims unchanged (3 pages)]
1. A compound having potassium channel inhibitory activity of the formula:
wherein, R1 is H, alkyl or is selected from the group consisting of an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted heterocyclyl and an optionally substituted carbocycloalkyl;
R2 is selected from the group consisting of alkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted heterocyclyl and an optionally substituted carbocycloalkyl;
R3 is hydrogen or methyl;
R4 is hydrogen or methyl;
X1 is C=0, C=S, or S02;
X2 is C=0 or S02; Y1 is O, (CH2)p, CH20, HC=CH or NH; wherein p is 0, 1 or 2;
Y2 is O, (CH2)q, HC=CH or NH; wherein q is 0 or 1;
Z is H, OR5 or NR6R7; wherein R5 is H, (CH2)m-R8; or C(0)-(CH2)m-R8; m = 1 to 5; R8 is N(R9)2, N(R9)3L or C02R9; wherein each R9 is independently selected from H or alkyl; and L is a counter ion;
R6 is H or alkyl;
R7 is H, alkyl or C02R10; wherein R10 is alkyl; or a pharmaceutically acceptable salt or prodrug thereof with the proviso that when Z is H, then X1 and X2 cannot both be C=0 while Y1 is (CH2)p with p=0, while Y2 is (CH2)q with q=0, and while R1 and R2 are both methyl.
R1 is H or an optionally substituted aryl selected from the group of phenyl and β-naphthyl;
R2 is selected from the group of an optionally substituted phenyl, an optionally substituted heterocyclyl, an optionally substituted heteroaryl and an optionally substituted carbocycloalkyl; m is 0 or 1;
X is O or S ; and
Y is selected from one of (CHJ-,, (CHjO), and (NH).; where p is 0, 1 or 2; q is O or 1, and r is O or 1; or a pharmaceutically acceptable salt or prodrug thereof.
4. A compound according to claim 3 having the formula:
wherein R1, R2 and p have the same meanings recited in claim 3; or a pharmaceutically acceptable salt or prodrug thereof.
5. A pharmaceutical composition comprising a compound of the following formula:
wherein, R1 is H, alkyl or is selected from the group consisting of an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted heterocyclyl and an optionally substituted carbocycloalkyl;
R2 is selected from the group consisting of alkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted heterocyclyl and an optionally substituted carbocycloalkyl; R3 is hydrogen or methyl; R4 is hydrogen or methyl; X1 is C=0, C=S, or S02; X2 is C=0 or S02;
Y1 is O, (CH2)p, CH20, HC=CH orNH; wherein p is 0, 1 or 2; Y2 is O, (CH2)q, HC=CH or NH; wherein q is 0 or 1; Z is H, OR5 or NR6R7; wherein R5 is H, (CH2)m-R8; or C(0)-(CH2)m-R8; m = l to 5;
R8 is N(R N(R9)3L or C02R9; wherein each R9 is independently selected from H or alkyl; and L is a counter ion; R6 is H or alkyl;
R7 is H, alkyl or C02R10; wherein R10 is alkyl; or a pharmaceutically acceptable salt or prodrug thereof; and a pharmaceutically acceptable diluent or carrier with the proviso that when Z is H, then X1 and X2 cannot both be C=0 while Y1 is (CH2)p with p=0, while Y2 is (CH2)q with q=0, and while R1 and R2 are both methyl. 6. A pharmaceutical composition comprising a compound of the following formula:
wherein,
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU38035/97A AU734711B2 (en) | 1996-07-26 | 1997-07-23 | Potassium channel inhibitors |
EP97934996A EP0923543B1 (en) | 1996-07-26 | 1997-07-23 | Potassium channel inhibitors |
HU0003250A HUP0003250A3 (en) | 1996-07-26 | 1997-07-23 | Potassium channel inhibitor indane derivatives and pharmaceutical compositions containing the same |
IL12820597A IL128205A (en) | 1996-07-26 | 1997-07-23 | Indane derivatives and pharmaceutical compositions containing the same |
CA002261814A CA2261814A1 (en) | 1996-07-26 | 1997-07-23 | Potassium channel inhibitors |
AT97934996T ATE250571T1 (en) | 1996-07-26 | 1997-07-23 | POTASSIUM CHANNEL BLOCKERS |
JP50888498A JP2002513385A (en) | 1996-07-26 | 1997-07-23 | Potassium channel inhibitor |
DE69725153T DE69725153T2 (en) | 1996-07-26 | 1997-07-23 | POTASSIUM CHANNEL BLOCKER |
BR9710587-2A BR9710587A (en) | 1996-07-26 | 1997-07-23 | Potassium channel inhibitors |
HK99105493A HK1020334A1 (en) | 1996-07-26 | 1999-11-26 | Potassium channel inhibitors |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US2254796P | 1996-07-26 | 1996-07-26 | |
US08/893,160 US6083986A (en) | 1996-07-26 | 1997-07-15 | Potassium channel inhibitors |
US60/022,547 | 1997-07-15 | ||
US08/893,160 | 1997-07-15 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1998004521A1 WO1998004521A1 (en) | 1998-02-05 |
WO1998004521B1 true WO1998004521B1 (en) | 1998-03-26 |
Family
ID=26696048
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1997/012559 WO1998004521A1 (en) | 1996-07-26 | 1997-07-23 | Potassium channel inhibitors |
Country Status (13)
Country | Link |
---|---|
US (1) | US6083986A (en) |
EP (1) | EP0923543B1 (en) |
JP (1) | JP2002513385A (en) |
KR (1) | KR20000029605A (en) |
AT (1) | ATE250571T1 (en) |
AU (1) | AU734711B2 (en) |
BR (1) | BR9710587A (en) |
CA (1) | CA2261814A1 (en) |
DE (1) | DE69725153T2 (en) |
HK (1) | HK1020334A1 (en) |
HU (1) | HUP0003250A3 (en) |
IL (1) | IL128205A (en) |
WO (1) | WO1998004521A1 (en) |
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1997
- 1997-07-15 US US08/893,160 patent/US6083986A/en not_active Expired - Lifetime
- 1997-07-23 EP EP97934996A patent/EP0923543B1/en not_active Expired - Lifetime
- 1997-07-23 AT AT97934996T patent/ATE250571T1/en not_active IP Right Cessation
- 1997-07-23 BR BR9710587-2A patent/BR9710587A/en not_active Application Discontinuation
- 1997-07-23 DE DE69725153T patent/DE69725153T2/en not_active Expired - Fee Related
- 1997-07-23 KR KR1019997000669A patent/KR20000029605A/en active IP Right Grant
- 1997-07-23 JP JP50888498A patent/JP2002513385A/en not_active Ceased
- 1997-07-23 HU HU0003250A patent/HUP0003250A3/en unknown
- 1997-07-23 AU AU38035/97A patent/AU734711B2/en not_active Ceased
- 1997-07-23 CA CA002261814A patent/CA2261814A1/en not_active Abandoned
- 1997-07-23 IL IL12820597A patent/IL128205A/en not_active IP Right Cessation
- 1997-07-23 WO PCT/US1997/012559 patent/WO1998004521A1/en active IP Right Grant
-
1999
- 1999-11-26 HK HK99105493A patent/HK1020334A1/en not_active IP Right Cessation
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