IP Library Granted Patent US 6,841,702
Granted Patent B2
US 6,841,702 · App. 10/239,074 · Granted Jan 11, 2005

Highly selective inhibitors of the urokinase plasminogen activator

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 6,841,702
App. No.
10/239,074
Granted
Jan 11, 2005
Kind
B2
Abstract

The invention relates to novel selective inhibitors of the urokinase plasminogen activator (uPA, EC 3.4.21.31), of the arylguanidine type.

Claims (24)

1. A compound of the formula (I)

Ar is an aromatic or heteroaromatic ring system,

X 1 is a radical of the formula (IIa), (IIb) or (IIc):

R 1 is H, an unsubstituted or substituted alkyl, alkenyl, alkynyl, aryl or/and heteroaryl radical,

R 2 is halogen, C(R 3 ) 3 , C 2 (R 3 ) 5 , OC(R 3 ) 3 or OC 2 (R 3 ) 5 ,

R 3 is in each case independently H or halogen,

R 4 and R 5 are H or an unsubstituted or substituted alkyl, alkenyl or alkynyl radical, where at least one of the radicals R 4 and R 5 contain a hydrogen bond donor group, where the hydrogen bond donor group provides a hydrogen atom or/and an electron pair for a hydrogen bond,

R 6 and R 7 are H or an unsubstituted or substituted alkyl, alkenyl or alkynyl radical, where at least one of the radicals R 6 and R 7 contains a hydrogen bond donor group, where the hydrogen bond donor group provides a hydrogen atom or/and an electron pair for a hydrogen bond and where R 4 or R 5 may be bridged with R 6 or R 7 ,

R 8 is H or an unsubstituted or substituted alkyl, alkenyl, alkynyl, aryl or heteroaryl radical or —SO 2 —R 9 , where R 8 may or may not be bridged with R 6 or R 7 ,

R 9 is H or an unsubstituted or substituted alkyl, alkenyl, alkynyl, aryl or heteroaryl radical,

X 2 is a hydrogen bond acceptor group, which is NH, NR 10 , O or S,

R 10 is an unsubstituted or substituted alkyl, alkenyl or alkynyl radical, and

m is an integer from 0 to 4,

 or salts of said compounds.

2. The compound of claim 1 , wherein Ar is a benzene ring.

3. The compound of claim 2 , wherein the substituents —CHX 1 R 1 and —NHCH 2 NHCH 2 NH 2

are arranged on the benzene ring in para position in relation to one another.

4. The compound of claim 1 , wherein for R 4 , R 5 , R 6 and R 7 , the hydrogen bond donor groups are selected from OH, OR 1 , NH 2 , NHR 1 , N(R 1 ) 2 , SH and SR 1 .

5. The compound of claim 1 , wherein the hydrogen bond donor group is contained in a group selected from —CH 2 OH, —CH 2 CH 2 OH, —CO 2 H, —CO 2 R 1 , CONH 2 , —CONHR 1 , —CON(R 11 ) 2 , —COSH, —COSR 1 , —CSOH, —COSR 1 , —COR 1 and —CSR 1 .

6. The compound of claim 1 , wherein for X 2 the hydrogen bond acceptor groups are selected from O and NH.

7. The compound of claim 1 , wherein R 8 and R 9 are selected from the group comprising of unsubstituted or substituted aryl radicals, unsubstituted or substituted tertiary alkyl radicals and cycloalkyl radicals.

8. The compound of claim 1 , wherein said compound is in the form of tablets, coated tablets, capsules, pellets, suppositories, solutions or transdermal systems.

9. The compound of claim 1 , wherein R 8 and R 9 are selected from the group consisting of phenyl and substituted phenyl radicals, unsubstituted or substituted tertiary alkyl radicals and bicycloalkyl radicals.

10. The compound of claim 1 , wherein R 8 and R 9 are selected from the group consisting of phenyl and substituted phenyl radicals, unsubstituted or substituted tertiary alkyl radicals and an adamantyl radical.

Assignments (4)
RE-RECORD TO CORRECT PROPERTY NUMBER ON A DOCUMENT PREVIOUSLY RECORDED AT REEL 022127, FRAME 0451. (ASSIGNMENT OF ASSIGNOR'S INTEREST) Recorded Apr 20, 2009
From: WILEX AG
To: WILEX AG
Reel/Frame 022575/0312 →
CHANGE OF ADDRESS WITH TRANSLATION Recorded Jan 16, 2009
From: WILEX AG
To: WILEX AG
Reel/Frame 022127/0451 →
CHANGE OF NAME Recorded Jan 22, 2007
From: WILEX BIOTECHNOLOGY GMBH
To: WILEX AG
Reel/Frame 018787/0054 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 20, 2002
From: BODE, WOLFRAM; MORODER, LUIS; HUBER, ROBERT; JACOB, UWE; ARROYO DE PRADA, NURIA; WILHELM, OLAF; STUERZEBECHER, JOERG; MAGDOLEN, VIKTOR; SPERL, STEFAN
To: WILEX BIOTECHNOLOGY GMBH; MAX-PLANCK-GESSELLSCHAFT ZUR FORDERUNG DER WISSENSCHAFTEN EV
Reel/Frame 013439/0140 →