ZA200206590B - Pteridine compounds for the treatment of psoriasis. - Google Patents
Pteridine compounds for the treatment of psoriasis. Download PDFInfo
- Publication number
- ZA200206590B ZA200206590B ZA200206590A ZA200206590A ZA200206590B ZA 200206590 B ZA200206590 B ZA 200206590B ZA 200206590 A ZA200206590 A ZA 200206590A ZA 200206590 A ZA200206590 A ZA 200206590A ZA 200206590 B ZA200206590 B ZA 200206590B
- Authority
- ZA
- South Africa
- Prior art keywords
- thio
- pteridinone
- amino
- hydroxy
- methyl
- Prior art date
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- 125000001042 pteridinyl group Chemical class N1=C(N=CC2=NC=CN=C12)* 0.000 title claims description 5
- 201000004681 Psoriasis Diseases 0.000 title description 2
- -1 2,3-Difluorophenyl Chemical group 0.000 claims description 101
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 98
- 150000001875 compounds Chemical class 0.000 claims description 65
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 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 13
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- CIZZUEUKGNBQPP-UHFFFAOYSA-N ethyl 2-anilino-7-oxo-8-phenylpteridine-6-carboxylate Chemical compound N1=C2N(C=3C=CC=CC=3)C(=O)C(C(=O)OCC)=NC2=CN=C1NC1=CC=CC=C1 CIZZUEUKGNBQPP-UHFFFAOYSA-N 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- OOIPDYWPGUHUJW-UHFFFAOYSA-N 8h-pteridin-7-one Chemical compound C1=NC=NC2=NC(O)=CN=C21 OOIPDYWPGUHUJW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 150000003573 thiols Chemical class 0.000 claims description 3
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
- WAELWVTWUVIVOT-UHFFFAOYSA-N 2-[(2,3-difluorophenyl)methylsulfanyl]-4-(4-hydroxybutylamino)-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(NCCCCO)=NC=1SCC1=CC=CC(F)=C1F WAELWVTWUVIVOT-UHFFFAOYSA-N 0.000 claims description 2
- DRYFUUVSGBBGLL-UHFFFAOYSA-N 2-[(2,3-difluorophenyl)methylsulfanyl]-4-[2-hydroxyethyl(methyl)amino]-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(N(CCO)C)=NC=1SCC1=CC=CC(F)=C1F DRYFUUVSGBBGLL-UHFFFAOYSA-N 0.000 claims description 2
- MPGKKVURGBVKGW-UHFFFAOYSA-N 2-[(3-chloro-2-fluorophenyl)methylsulfanyl]-4-(2-hydroxyethylamino)-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(NCCO)=NC=1SCC1=CC=CC(Cl)=C1F MPGKKVURGBVKGW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
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- 125000006239 protecting group Chemical group 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- QHAIWKDCYWFSRO-SECBINFHSA-N 2-(1,3-benzodioxol-4-ylmethylsulfanyl)-4-[[(2r)-1-hydroxypropan-2-yl]amino]-8h-pteridin-7-one Chemical compound N1C(=O)C=NC2=C1N=C(SCC=1C=3OCOC=3C=CC=1)N=C2N[C@@H](CO)C QHAIWKDCYWFSRO-SECBINFHSA-N 0.000 claims 1
- ALHFTXQQJSWTIT-UHFFFAOYSA-N 2-[(2,3-difluorophenyl)methylsulfanyl]-4-(2-hydroxyethylamino)-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(NCCO)=NC=1SCC1=CC=CC(F)=C1F ALHFTXQQJSWTIT-UHFFFAOYSA-N 0.000 claims 1
- CTTSXKXRFZXVFC-MRVPVSSYSA-N 2-[(2,3-difluorophenyl)methylsulfanyl]-4-[[(2r)-2-hydroxypropyl]amino]-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(NC[C@H](O)C)=NC=1SCC1=CC=CC(F)=C1F CTTSXKXRFZXVFC-MRVPVSSYSA-N 0.000 claims 1
- CTMLHRHDVSWSQE-UHFFFAOYSA-N 2-[(2,3-difluorophenyl)methylsulfanyl]-4-[ethyl(2-hydroxyethyl)amino]-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(N(CCO)CC)=NC=1SCC1=CC=CC(F)=C1F CTMLHRHDVSWSQE-UHFFFAOYSA-N 0.000 claims 1
- WVNDNQWPAYCUBF-UHFFFAOYSA-N 2-[[2-fluoro-3-(trifluoromethyl)phenyl]methylsulfanyl]-4-(2-hydroxyethylamino)-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(NCCO)=NC=1SCC1=CC=CC(C(F)(F)F)=C1F WVNDNQWPAYCUBF-UHFFFAOYSA-N 0.000 claims 1
- OKTVAUNSMLMTBE-UHFFFAOYSA-N 4-(1,3-dihydroxypropan-2-ylamino)-2-(thiophen-2-ylmethylsulfanyl)-8h-pteridin-7-one Chemical compound N=1C=2NC(=O)C=NC=2C(NC(CO)CO)=NC=1SCC1=CC=CS1 OKTVAUNSMLMTBE-UHFFFAOYSA-N 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- DIPUNMJILBEXGC-MNMPKAIFSA-N FC1=C(CSC2=NC=3NC(C=NC3C(=N2)NCCCCCO)=O)C=CC=C1F.FC1=C(CSC2=NC=3NC(C=NC3C(=N2)N[C@H]2[C@@H](CCC2)O)=O)C=CC=C1F Chemical compound FC1=C(CSC2=NC=3NC(C=NC3C(=N2)NCCCCCO)=O)C=CC=C1F.FC1=C(CSC2=NC=3NC(C=NC3C(=N2)N[C@H]2[C@@H](CCC2)O)=O)C=CC=C1F DIPUNMJILBEXGC-MNMPKAIFSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 101150088095 RTM2 gene Proteins 0.000 claims 1
- BEOAYHGWRUBNCB-UHFFFAOYSA-N [Na].O=c1ncc2nccnc2[nH]1 Chemical compound [Na].O=c1ncc2nccnc2[nH]1 BEOAYHGWRUBNCB-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
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GB0004128A GB2359551A (en) | 2000-02-23 | 2000-02-23 | Pharmaceutically active pyrimidine derivatives |
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ZA200206590A ZA200206590B (en) | 2000-02-23 | 2002-08-16 | Pteridine compounds for the treatment of psoriasis. |
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US (2) | US6875868B2 (tr) |
EP (1) | EP1259512B1 (tr) |
JP (1) | JP2003524012A (tr) |
KR (1) | KR100795758B1 (tr) |
CN (1) | CN1190437C (tr) |
AR (1) | AR029805A1 (tr) |
AT (1) | ATE250605T1 (tr) |
AU (1) | AU782509B2 (tr) |
BG (1) | BG107002A (tr) |
BR (1) | BR0108600A (tr) |
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DK (1) | DK1259512T3 (tr) |
EE (1) | EE200200461A (tr) |
ES (1) | ES2206402T3 (tr) |
GB (1) | GB2359551A (tr) |
HK (1) | HK1050899A1 (tr) |
HU (1) | HUP0204399A3 (tr) |
IL (2) | IL151132A0 (tr) |
IS (1) | IS6491A (tr) |
MX (1) | MXPA02008233A (tr) |
NO (1) | NO329898B1 (tr) |
NZ (1) | NZ520355A (tr) |
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PT (1) | PT1259512E (tr) |
RU (1) | RU2002125451A (tr) |
SK (1) | SK12152002A3 (tr) |
TR (1) | TR200302214T4 (tr) |
UA (1) | UA72590C2 (tr) |
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SE9903544D0 (sv) * | 1999-10-01 | 1999-10-01 | Astra Pharma Prod | Novel compounds |
GB2359078A (en) | 2000-02-11 | 2001-08-15 | Astrazeneca Uk Ltd | Pharmaceutically active pyrimidine derivatives |
GB2359081A (en) | 2000-02-11 | 2001-08-15 | Astrazeneca Uk Ltd | Pharmaceutically active thiazolopyrimidines |
GB2359551A (en) * | 2000-02-23 | 2001-08-29 | Astrazeneca Uk Ltd | Pharmaceutically active pyrimidine derivatives |
SE0003828D0 (sv) | 2000-10-20 | 2000-10-20 | Astrazeneca Ab | Novel compounds |
EA007538B1 (ru) | 2000-12-11 | 2006-10-27 | Туларик Инк. | Антагонисты cxcr3 |
SE0101322D0 (sv) * | 2001-04-12 | 2001-04-12 | Astrazeneca Ab | Novel compounds |
US6794379B2 (en) | 2001-06-06 | 2004-09-21 | Tularik Inc. | CXCR3 antagonists |
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GB0221828D0 (en) * | 2002-09-20 | 2002-10-30 | Astrazeneca Ab | Novel compound |
US7067658B2 (en) | 2002-09-30 | 2006-06-27 | Bristol-Myers Squibb Company | Pyridino and pyrimidino pyrazinones |
US6861422B2 (en) | 2003-02-26 | 2005-03-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Dihydropteridinones, processes for preparing them and their use as pharmaceutical compositions |
GB0328243D0 (en) * | 2003-12-05 | 2004-01-07 | Astrazeneca Ab | Methods |
US7375102B2 (en) | 2004-06-28 | 2008-05-20 | Amgen Sf, Llc | Tetrahydroquinazolin-4(3H)-one-related and tetrahydropyrido[2,3-D]pyrimidin-4(3H)-one-related compounds, compositions and methods for their use |
US7271271B2 (en) | 2004-06-28 | 2007-09-18 | Amgen Sf, Llc | Imidazolo-related compounds, compositions and methods for their use |
US7939538B2 (en) | 2004-06-28 | 2011-05-10 | Amgen Inc. | Compounds, compositions and methods for prevention and treatment of inflammatory and immunoregulatory disorders and diseases |
DE102004033670A1 (de) * | 2004-07-09 | 2006-02-02 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Pyridodihydropyrazinone, Verfahren zu Ihrer Herstellung und Ihre Verwendung als Arzneimittel |
US20060074088A1 (en) | 2004-08-14 | 2006-04-06 | Boehringer Ingelheim International Gmbh | Dihydropteridinones for the treatment of cancer diseases |
US7759485B2 (en) | 2004-08-14 | 2010-07-20 | Boehringer Ingelheim International Gmbh | Process for the manufacture of dihydropteridinones |
US20060058311A1 (en) | 2004-08-14 | 2006-03-16 | Boehringer Ingelheim International Gmbh | Combinations for the treatment of diseases involving cell proliferation |
US20060035903A1 (en) | 2004-08-14 | 2006-02-16 | Boehringer Ingelheim International Gmbh | Storage stable perfusion solution for dihydropteridinones |
US7728134B2 (en) * | 2004-08-14 | 2010-06-01 | Boehringer Ingelheim International Gmbh | Hydrates and polymorphs of 4[[(7R)-8-cyclopentyl-7-ethyl-5,6,7,8-tetrahydro-5-methyl-6-oxo-2-pteridinyl]amino]-3-methoxy-N-(1-methyl-4-piperidinyl)-benzamide, process for their manufacture and their use as medicament |
DE102004058337A1 (de) | 2004-12-02 | 2006-06-14 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Verfahren zur Herstellung von annelierten Piperazin-2-on Derivaten |
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