Substituted pyrroloanthracenes and -diones

• US 5,411,960 A
• Filed: 12/09/1993
• Issued: 05/02/1995
• Est. Priority Date: 12/09/1993
• Status: Expired due to Fees

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Ladouceur, Gaetan, Aune, Thomas M., Schwenner, Eckhard, Kabbe, Hans-Joachim
• Primary Examiner(s): Lee, Mary C.
• Assistant Examiner(s): McKane, Joseph K.
• Application Number:
  US08/164,495
• Time in Patent Office: 509 Days
• Field of Search: 548/418, 548/419, 546/113, 546/139, 546/201, 546/208, 544/105, 514/230.5, 514/300, 514/307, 514/410, 514/323, 556/407
• US Class Current: 514/230.5
• CPC Class Codes: A61P 37/00 Drugs for immunological or allergic disorders
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07D 209/76 with oxygen atoms in positions 1 and 3
• CPC Class Codes: C07D 209/94 containing carbocyclic rings other than six-membered
• CPC Class Codes: C07D 401/06 linked by a carbon chain containing only aliphatic carbon atoms
• CPC Class Codes: C07D 471/04 Ortho-condensed systems
• CPC Class Codes: C07D 487/04 Ortho-condensed systems
• CPC Class Codes: C07F 7/0812 comprising a heterocyclic ring

Abstract

Substituted pyrroloanthracenes are prepared by reacting either furanoanthracenes or N-unsubstituted pyrroloanthracenes with appropriately substituted alkylamines. The compounds can be employed as active ingredients in medicaments, in particular as immunomodulators.

Claims

1. A substituted pyrroloanthracene or -dione of the general formula (I) ##STR47## in which A and D are identical or different and represent hydrogen, hydroxyl, halogen, cyano, carboxyl, nitro, trifluoromethyl or trifluoromethoxy, or represent straight-chain or branched alkyl or alkoxy in each case having up to 8 carbon atoms,

R¹ and R² are identical or different and represent hydrogen, halogen, cyano, formyl, phenyl or hydroxyl, or represent straight-chain or branched alkoxy having up to 8 carbon atoms, or represent straight-chain or branched alkyl or alkenyl in each case having up to 8 carbon atoms, each of which is optionally substituted up to 2 times by identical or different hydroxyl, nitro, phenyl or halogen, by straight-chain or branched alkoxy having up to 6 carbon atoms or by a group of the formula --NR³ R⁴,

in which

R³ and R⁴ are identical or different and denote hydrogen, straight-chain or branched alkyl having up to 6 carbon atoms or phenyl,

E and L together form a heterocyclic radical of the formula ##STR48## in which R⁵ and R⁶ are identical or different and denote hydrogen, halogen, phenyl or straight-chain or branched alkyl having up to 8 carbon atoms, which is optionally substituted by carboxyl or by straight-chain or branched alkoxycarbonyl having up to 6 carbon atoms,

R⁷, R⁸, R⁹ and R¹⁰ are identical or different and denote hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms, or

R⁷ and R⁸ and/or R⁹ and R¹⁰ in each case together form the radical of the formula =O,

T denotes straight-chain or branched alkyl having up to 4 carbon atoms,

V denotes a radical of the formula ##STR49## in which a denotes a number 1 or 2,

R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ are identical or different and denote benzyl or aryl having 6 to 10 carbon atoms, each of which is optionally substituted up to 3 times by identical or different halogen, hydroxyl, nitro, cyano, trifluoromethyl or trifluoromethoxy or by straight-chain or branched alkyl or alkoxy in each case having up to 8 carbon atoms,

and its salts.

2. A substituted pyrroloanthracene or -dione as claimed in claim 1

in which

A and D are identical or different and represent hydrogen, hydroxyl, fluorine, chlorine, bromine, carboxyl, nitro, trifluoromethyl, trifluoromethoxy or

represent straight-chain or branched alkyl or alkoxy in each case having up to 6 carbon atoms,

R¹ and R² are identical or different and represent hydrogen, fluorine, chlorine, bromine, cyano, formyl, phenyl or hydroxyl, or represent straight-chain or branched alkoxy having up to 6 carbon atoms, or represent straight-chain or branched alkyl or alkenyl in each case having up to 6 carbon atoms, each of which is optionally substituted up to 2 times by identical or different hydroxyl, nitro, phenyl, fluorine, chlorine or bromine, by straight-chain or branched alkoxy having up to 4 carbon atoms or by a group of the formula --NR³ R⁴,

in which

R³ and R⁴ are identical or different and denote hydrogen, straight-chain or branched alkyl having up to 4 carbon atoms or phenyl,

E and L together form a heterocyclic radical of the formula ##STR50## in which R⁵ and R⁶ are identical or different and denote hydrogen, fluorine, chlorine, bromine, phenyl or straight-chain or branched alkyl having up to 6 carbon atoms, which is optionally substituted by carboxyl or by straight-chain or branched alkoxycarbonyl having up to 4 carbon atoms,

R⁷, R⁸, R⁹ and R¹⁰ are identical or different and denote hydrogen or straight-chain or branched alkyl having up to 4 carbon atoms, or

R⁷ and R⁸ and/or R⁹ and R¹⁰ in each case together form the radical of the formula =O,

T denotes straight-chain or branched alkyl having up to 4 carbon atoms,

V denotes a radical of the formula ##STR51## in which a denotes a number 1 or 2,

R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ are identical or different and denote benzyl or phenyl, each of which is optionally substituted up to 3 times by identical or different fluorine, chlorine, bromine, hydroxyl, nitro, cyano, trifluoromethyl or trifluoromethoxy or by straight-chain or branched alkyl or alkoxy in each case having up to 6 carbon atoms,

and its salts.

3. A substituted pyrroloanthracene or -dione as claimed in claim 1

in which

A and D are identical or different and represent hydrogen, hydroxyl, fluorine, chlorine, bromine or straight-chain or branched alkyl having up to 4 carbon atoms,

R¹ and R² are identical or different and represent hydrogen, fluorine, chlorine, bromine, cyano, formyl, phenyl or hydroxyl, or represent straight-chain or branched alkoxy having up to 4 carbon atoms, or represent straight-chain or branched alkyl or alkenyl in each case having up to 4 carbon atoms, each of which is optionally substituted up to 2 times by identical or different hydroxyl, nitro, phenyl, fluorine, chlorine or bromine, by straight-chain or branched alkoxy having up to 3 carbon atoms or by amino or aminomethyl,

E and L together form a heterocyclic radical of the formula ##STR52## in which R⁵ and R⁶ are identical or different and denote hydrogen, fluorine, chlorine, bromine, phenyl or straight-chain or branched alkyl having up to 4 carbon atoms, which is optionally substituted by carboxyl or by straight-chain or branched alkoxycarbonyl having up to 3 carbon atoms,

R⁷, R⁸, R⁹ and R¹⁰ are identical or different and denote hydrogen or straight-chain or branched alkyl having up to 3 carbon atoms, or

R⁷ and R⁸ and/or R⁹ and R¹⁰ in each case together form the radical of the formula =O,

T denotes straight-chain or branched alkyl having up to 4 carbon atoms

V denotes a radical of the formula ##STR53## in which a denotes a number 1 or 2,

R¹¹, R¹², R¹³, R¹⁴, R¹⁵ and R¹⁶ are identical or different and denote benzyl or phenyl, each of which is optionally substituted up to 3 times by identical or different fluorine, chlorine, bromine, hydroxyl, nitro, cyano, trifluoromethyl or trifluoromethoxy or by straight-chain or branched alkyl or alkoxy in each case having up to 4 carbon atoms,

and its salts.

4. A pharmaceutical composition comprising a compound according to claim 1 and an auxiliary or excipient.

5. A method of treating arthritis which comprises administering a compound according to claim 1, to a host in need thereof.