ZA200502692B - PGD2 receptor antagonists for the treatment of inflammatory diseases - Google Patents
PGD2 receptor antagonists for the treatment of inflammatory diseases Download PDFInfo
- Publication number
- ZA200502692B ZA200502692B ZA200502692A ZA200502692A ZA200502692B ZA 200502692 B ZA200502692 B ZA 200502692B ZA 200502692 A ZA200502692 A ZA 200502692A ZA 200502692 A ZA200502692 A ZA 200502692A ZA 200502692 B ZA200502692 B ZA 200502692B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenyl
- methyl
- tetrahydro
- group
- quinolinyl
- Prior art date
Links
- 108050000258 Prostaglandin D receptors Proteins 0.000 title claims description 46
- 208000027866 inflammatory disease Diseases 0.000 title claims description 8
- 102000009389 Prostaglandin D receptors Human genes 0.000 title claims description 6
- 239000002464 receptor antagonist Substances 0.000 title description 2
- 229940044551 receptor antagonist Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 92
- -1 cycloaliphatic group Chemical group 0.000 claims description 78
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 230000002401 inhibitory effect Effects 0.000 claims description 27
- 125000001931 aliphatic group Chemical group 0.000 claims description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
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- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
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- TVDYOGKGVPLVES-UHFFFAOYSA-N n-[1-(3-chlorobenzoyl)-2-methyl-3,4-dihydro-2h-quinolin-4-yl]-n-phenylacetamide Chemical compound C12=CC=CC=C2N(C(=O)C=2C=C(Cl)C=CC=2)C(C)CC1N(C(C)=O)C1=CC=CC=C1 TVDYOGKGVPLVES-UHFFFAOYSA-N 0.000 claims description 3
- 125000005893 naphthalimidyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
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- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 2
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- LFQVRKSJUGBYIP-UHFFFAOYSA-N 5-[4-(n-acetylanilino)-2-methyl-3,4-dihydro-2h-quinolin-1-yl]-4-oxopentanoic acid Chemical compound C12=CC=CC=C2N(CC(=O)CCC(O)=O)C(C)CC1N(C(C)=O)C1=CC=CC=C1 LFQVRKSJUGBYIP-UHFFFAOYSA-N 0.000 claims description 2
- 208000019693 Lung disease Diseases 0.000 claims description 2
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- CHQKTCNLPLKHGS-UHFFFAOYSA-N n-[1-(4-fluorobenzoyl)-2-methyl-3,4-dihydro-2h-quinolin-4-yl]-n-phenylbutanamide Chemical compound C=1C=CC=CC=1N(C(=O)CCC)C(C1=CC=CC=C11)CC(C)N1C(=O)C1=CC=C(F)C=C1 CHQKTCNLPLKHGS-UHFFFAOYSA-N 0.000 description 1
- ZOOFIOUKBSCSCU-UHFFFAOYSA-N n-[1-(4-fluorobenzoyl)-2-methyl-6-nitro-3,4-dihydro-2h-quinolin-4-yl]-n-phenylacetamide Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(C(=O)C=2C=CC(F)=CC=2)C(C)CC1N(C(C)=O)C1=CC=CC=C1 ZOOFIOUKBSCSCU-UHFFFAOYSA-N 0.000 description 1
- WFIFILNFPGGECZ-UHFFFAOYSA-N n-[1-(4-methoxybenzoyl)-2-methyl-3,4-dihydro-2h-quinolin-4-yl]-n-(3-phenylphenyl)acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)N1C2=CC=CC=C2C(N(C(C)=O)C=2C=C(C=CC=2)C=2C=CC=CC=2)CC1C WFIFILNFPGGECZ-UHFFFAOYSA-N 0.000 description 1
- RVOSQGSTJXRWIC-UHFFFAOYSA-N n-[1-(4-methoxybenzoyl)-2-methyl-3,4-dihydro-2h-quinolin-4-yl]-n-phenylfuran-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C(=O)N1C2=CC=CC=C2C(N(C(=O)C=2OC=CC=2)C=2C=CC=CC=2)CC1C RVOSQGSTJXRWIC-UHFFFAOYSA-N 0.000 description 1
- FJUIADLFVDKJAP-UHFFFAOYSA-N n-[1-(4-tert-butylbenzoyl)-2-methyl-3,4-dihydro-2h-quinolin-4-yl]-n-phenylacetamide Chemical compound C12=CC=CC=C2N(C(=O)C=2C=CC(=CC=2)C(C)(C)C)C(C)CC1N(C(C)=O)C1=CC=CC=C1 FJUIADLFVDKJAP-UHFFFAOYSA-N 0.000 description 1
- KNWDGZUFTMYBGN-UHFFFAOYSA-N n-[1-(cyclopropanecarbonyl)-2-methyl-3,4-dihydro-2h-quinolin-4-yl]-n-phenylcyclopropanecarboxamide Chemical compound C12=CC=CC=C2N(C(=O)C2CC2)C(C)CC1N(C=1C=CC=CC=1)C(=O)C1CC1 KNWDGZUFTMYBGN-UHFFFAOYSA-N 0.000 description 1
- MYKQEFFQJACTID-UHFFFAOYSA-N n-[1-(furan-2-carbonyl)-2-methyl-3,4-dihydro-2h-quinolin-4-yl]-n-phenylfuran-2-carboxamide Chemical compound C12=CC=CC=C2N(C(=O)C=2OC=CC=2)C(C)CC1N(C=1C=CC=CC=1)C(=O)C1=CC=CO1 MYKQEFFQJACTID-UHFFFAOYSA-N 0.000 description 1
- NZUKXTSTQIFSJP-UHFFFAOYSA-N n-[2-methyl-1-(2-methylpropanoyl)-3,4-dihydro-2h-quinolin-4-yl]-n-phenylacetamide Chemical compound C12=CC=CC=C2N(C(=O)C(C)C)C(C)CC1N(C(C)=O)C1=CC=CC=C1 NZUKXTSTQIFSJP-UHFFFAOYSA-N 0.000 description 1
- NXMWWXCBFBLNAO-UHFFFAOYSA-N n-[2-methyl-1-(3-phenylpropanoyl)-3,4-dihydro-2h-quinolin-4-yl]-n,3-diphenylpropanamide Chemical compound C12=CC=CC=C2N(C(=O)CCC=2C=CC=CC=2)C(C)CC1N(C=1C=CC=CC=1)C(=O)CCC1=CC=CC=C1 NXMWWXCBFBLNAO-UHFFFAOYSA-N 0.000 description 1
- NVESFBXAWNNACP-UHFFFAOYSA-N n-[2-methyl-1-(4-nitrobenzoyl)-3,4-dihydro-2h-quinolin-4-yl]-n-phenyloctanamide Chemical compound C=1C=CC=CC=1N(C(=O)CCCCCCC)C(C1=CC=CC=C11)CC(C)N1C(=O)C1=CC=C([N+]([O-])=O)C=C1 NVESFBXAWNNACP-UHFFFAOYSA-N 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 125000005545 phthalimidyl group Chemical group 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 208000005987 polymyositis Diseases 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229940127293 prostanoid Drugs 0.000 description 1
- 150000003814 prostanoids Chemical class 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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US (2) | US7211672B2 (fr) |
EP (1) | EP1556047A4 (fr) |
JP (2) | JP2006508077A (fr) |
KR (1) | KR20050055747A (fr) |
CN (1) | CN100363348C (fr) |
AU (1) | AU2003277285B2 (fr) |
BR (1) | BR0315041A (fr) |
CA (1) | CA2500582A1 (fr) |
EA (1) | EA011385B1 (fr) |
MX (1) | MXPA05003456A (fr) |
NO (1) | NO20051566L (fr) |
PL (1) | PL376156A1 (fr) |
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-
2003
- 2003-10-03 MX MXPA05003456A patent/MXPA05003456A/es active IP Right Grant
- 2003-10-03 WO PCT/US2003/031542 patent/WO2004032848A2/fr active Application Filing
- 2003-10-03 US US10/678,872 patent/US7211672B2/en not_active Expired - Lifetime
- 2003-10-03 CA CA002500582A patent/CA2500582A1/fr not_active Abandoned
- 2003-10-03 CN CNB2003801047950A patent/CN100363348C/zh not_active Expired - Fee Related
- 2003-10-03 JP JP2004543358A patent/JP2006508077A/ja active Pending
- 2003-10-03 AU AU2003277285A patent/AU2003277285B2/en not_active Ceased
- 2003-10-03 KR KR1020057005853A patent/KR20050055747A/ko not_active Application Discontinuation
- 2003-10-03 EA EA200500536A patent/EA011385B1/ru not_active IP Right Cessation
- 2003-10-03 EP EP03808144A patent/EP1556047A4/fr not_active Withdrawn
- 2003-10-03 PL PL03376156A patent/PL376156A1/xx not_active Application Discontinuation
- 2003-10-03 BR BR0315041-0A patent/BR0315041A/pt not_active IP Right Cessation
-
2005
- 2005-03-23 NO NO20051566A patent/NO20051566L/no not_active Application Discontinuation
- 2005-04-04 ZA ZA200502692A patent/ZA200502692B/en unknown
- 2005-12-05 JP JP2005351372A patent/JP2006124396A/ja active Pending
- 2005-12-20 US US11/312,960 patent/US20060106061A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
JP2006124396A (ja) | 2006-05-18 |
CA2500582A1 (fr) | 2004-04-22 |
CN1720047A (zh) | 2006-01-11 |
CN100363348C (zh) | 2008-01-23 |
US20060106061A1 (en) | 2006-05-18 |
JP2006508077A (ja) | 2006-03-09 |
BR0315041A (pt) | 2005-08-16 |
MXPA05003456A (es) | 2005-07-05 |
PL376156A1 (en) | 2005-12-27 |
EA200500536A1 (ru) | 2005-10-27 |
EA011385B1 (ru) | 2009-02-27 |
AU2003277285B2 (en) | 2007-12-13 |
NO20051566L (no) | 2005-06-15 |
WO2004032848A2 (fr) | 2004-04-22 |
KR20050055747A (ko) | 2005-06-13 |
EP1556047A4 (fr) | 2009-09-30 |
AU2003277285A1 (en) | 2004-05-04 |
US20040082609A1 (en) | 2004-04-29 |
WO2004032848A3 (fr) | 2004-07-15 |
US7211672B2 (en) | 2007-05-01 |
EP1556047A2 (fr) | 2005-07-27 |
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