Discovery and SAR of novel [1,6]Naphthyridines as potent inhibitors of spleen tyrosine kinase (SYK)
The discovery of novel 5,7-disubstituted[1,6]naphthyridines as potent inhibitors of Spleen Tyrosine Kinase (SYK) is discussed. The SAR reveals the necessity for a 7-aryl group with preference towards para substitution and that this in combination with 5-aminoalkylamino substituents further improved...
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| Published in | Bioorganic & medicinal chemistry letters Vol. 13; no. 8; pp. 1415 - 1418 |
|---|---|
| Main Authors | , , , , , , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Oxford
Elsevier Ltd
17.04.2003
Elsevier |
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| Abstract | The discovery of novel 5,7-disubstituted[1,6]naphthyridines as potent inhibitors of Spleen Tyrosine Kinase (SYK) is discussed. The SAR reveals the necessity for a 7-aryl group with preference towards
para substitution and that this in combination with 5-aminoalkylamino substituents further improved the potency of the compounds. The initial SAR as well as a survey of the other positions is discussed in detail.
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| AbstractList | The discovery of novel 5,7-disubstituted[1,6]naphthyridines as potent inhibitors of Spleen Tyrosine Kinase (SYK) is discussed. The SAR reveals the necessity for a 7-aryl group with preference towards
para substitution and that this in combination with 5-aminoalkylamino substituents further improved the potency of the compounds. The initial SAR as well as a survey of the other positions is discussed in detail.
Graphic The discovery of novel 5,7-disubstituted[1,6]naphthyridines as potent inhibitors of Spleen Tyrosine Kinase (SYK) is discussed. The SAR reveals the necessity for a 7-aryl group with preference towards para substitution and that this in combination with 5-aminoalkylamino substituents further improved the potency of the compounds. The initial SAR as well as a survey of the other positions is discussed in detail. |
| Author | Prokopowicz, Anthony S Winters, Michael P Jakes, Scott Cywin, Charles L Morwick, Tina M Soll, Richard M Hrapchak, Matt McNeil, Daniel W Goldberg, Daniel R Player, Mark R Kashem, Mohammed Rinker, James Zhao, Bao-Ping Gao, Amy Magolda, Ronald L DesJarlais, Renee L Bobko, Mark A |
| Author_xml | – sequence: 1 givenname: Charles L surname: Cywin fullname: Cywin, Charles L email: ccywin@rdg.boehringer-ingelheim.com organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 2 givenname: Bao-Ping surname: Zhao fullname: Zhao, Bao-Ping organization: 3-Dimensional Pharmaeuticals, Inc., 665 Stockton Drive, Suite 104, Exton, PA 19341, USA – sequence: 3 givenname: Daniel W surname: McNeil fullname: McNeil, Daniel W organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 4 givenname: Matt surname: Hrapchak fullname: Hrapchak, Matt organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 5 givenname: Anthony S surname: Prokopowicz fullname: Prokopowicz, Anthony S organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 6 givenname: Daniel R surname: Goldberg fullname: Goldberg, Daniel R organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 7 givenname: Tina M surname: Morwick fullname: Morwick, Tina M organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 8 givenname: Amy surname: Gao fullname: Gao, Amy organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 9 givenname: Scott surname: Jakes fullname: Jakes, Scott organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 10 givenname: Mohammed surname: Kashem fullname: Kashem, Mohammed organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 11 givenname: Ronald L surname: Magolda fullname: Magolda, Ronald L organization: Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT 06801-0368, USA – sequence: 12 givenname: Richard M surname: Soll fullname: Soll, Richard M organization: 3-Dimensional Pharmaeuticals, Inc., 665 Stockton Drive, Suite 104, Exton, PA 19341, USA – sequence: 13 givenname: Mark R surname: Player fullname: Player, Mark R organization: 3-Dimensional Pharmaeuticals, Inc., 665 Stockton Drive, Suite 104, Exton, PA 19341, USA – sequence: 14 givenname: Mark A surname: Bobko fullname: Bobko, Mark A organization: 3-Dimensional Pharmaeuticals, Inc., 665 Stockton Drive, Suite 104, Exton, PA 19341, USA – sequence: 15 givenname: James surname: Rinker fullname: Rinker, James organization: 3-Dimensional Pharmaeuticals, Inc., 665 Stockton Drive, Suite 104, Exton, PA 19341, USA – sequence: 16 givenname: Renee L surname: DesJarlais fullname: DesJarlais, Renee L organization: 3-Dimensional Pharmaeuticals, Inc., 665 Stockton Drive, Suite 104, Exton, PA 19341, USA – sequence: 17 givenname: Michael P surname: Winters fullname: Winters, Michael P organization: 3-Dimensional Pharmaeuticals, Inc., 665 Stockton Drive, Suite 104, Exton, PA 19341, USA |
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| Cites_doi | 10.1084/jem.184.1.71 10.1055/s-2000-6254 10.1016/S0021-9258(18)43936-1 10.1128/MCB.15.8.4149 10.1016/S0167-5699(99)01574-1 10.1016/S0161-5890(02)00068-8 10.1128/MCB.15.3.1582 |
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| Keywords | Phosphorylation Enzyme Nitrogen heterocycle Transferases Enzyme inhibitor In vitro Diamine Signal transduction Structure activity relation Bicyclic compound Naphtyridine derivatives Chemical synthesis Protein-tyrosine kinase Aromatic amine |
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| References | Rivera, Brugge (BIB4) 1995; 15 Oliver, Burg, Wilson, McLaughlin, Geahlen (BIB6) 1994; 269 BIB9 Turner, Schweighoffer, Colucci, Di Santo, Tybulewicz (BIB1) 2000; 21 Siraganian, Zhang, Suzuki, Sada (BIB2) 2001; 38 Brun, Gil, Mestres, Parra (BIB7) 2000 Ames, Dodds (BIB8) 1972 Taylor, Karas, Ram, Green, Seidel-Dugan (BIB3) 1995; 15 Zhang, Berenstein, Evans, Siraganian (BIB5) 1996; 184 BIB10 Ames (10.1016/S0960-894X(03)00163-X_BIB8) 1972 Turner (10.1016/S0960-894X(03)00163-X_BIB1) 2000; 21 Zhang (10.1016/S0960-894X(03)00163-X_BIB5) 1996; 184 Brun (10.1016/S0960-894X(03)00163-X_BIB7) 2000 Oliver (10.1016/S0960-894X(03)00163-X_BIB6) 1994; 269 Taylor (10.1016/S0960-894X(03)00163-X_BIB3) 1995; 15 Siraganian (10.1016/S0960-894X(03)00163-X_BIB2) 2001; 38 Rivera (10.1016/S0960-894X(03)00163-X_BIB4) 1995; 15 |
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| SubjectTerms | Animals Biological and medical sciences Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology Enzyme Precursors - antagonists & inhibitors Humans Inhibitory Concentration 50 Intracellular Signaling Peptides and Proteins Medical sciences Miscellaneous Naphthyridines - chemistry Naphthyridines - pharmacology Pharmacology. Drug treatments Protein-Tyrosine Kinases - antagonists & inhibitors Spleen - enzymology Structure-Activity Relationship Syk Kinase |
| Title | Discovery and SAR of novel [1,6]Naphthyridines as potent inhibitors of spleen tyrosine kinase (SYK) |
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