CA2561564A1 - Pgd2 receptor antagonists for the treatment of inflammatory diseases - Google Patents
Pgd2 receptor antagonists for the treatment of inflammatory diseases Download PDFInfo
- Publication number
- CA2561564A1 CA2561564A1 CA002561564A CA2561564A CA2561564A1 CA 2561564 A1 CA2561564 A1 CA 2561564A1 CA 002561564 A CA002561564 A CA 002561564A CA 2561564 A CA2561564 A CA 2561564A CA 2561564 A1 CA2561564 A1 CA 2561564A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- substituted
- phenyl
- haloalkyl
- optionally substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 208000027866 inflammatory disease Diseases 0.000 title claims abstract description 17
- 108050000258 Prostaglandin D receptors Proteins 0.000 title abstract description 41
- 102000009389 Prostaglandin D receptors Human genes 0.000 title description 40
- 239000002464 receptor antagonist Substances 0.000 title 1
- 229940044551 receptor antagonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 231
- -1 -C(O)OR o Chemical group 0.000 claims description 728
- 238000000034 method Methods 0.000 claims description 231
- 125000000217 alkyl group Chemical group 0.000 claims description 198
- 125000001188 haloalkyl group Chemical group 0.000 claims description 165
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 137
- 229910052739 hydrogen Inorganic materials 0.000 claims description 129
- 125000003118 aryl group Chemical group 0.000 claims description 105
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 103
- 125000001072 heteroaryl group Chemical group 0.000 claims description 81
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 75
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 65
- 229940080818 propionamide Drugs 0.000 claims description 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
- 229910052799 carbon Inorganic materials 0.000 claims description 51
- 125000001424 substituent group Chemical group 0.000 claims description 51
- 150000004820 halides Chemical class 0.000 claims description 47
- 125000002757 morpholinyl group Chemical group 0.000 claims description 47
- 229910052736 halogen Inorganic materials 0.000 claims description 45
- 150000002367 halogens Chemical class 0.000 claims description 45
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims description 44
- 229910052757 nitrogen Inorganic materials 0.000 claims description 41
- 150000001721 carbon Chemical group 0.000 claims description 39
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 38
- 150000001412 amines Chemical group 0.000 claims description 37
- 125000002947 alkylene group Chemical group 0.000 claims description 35
- 125000002950 monocyclic group Chemical group 0.000 claims description 35
- 125000003386 piperidinyl group Chemical group 0.000 claims description 33
- 125000004193 piperazinyl group Chemical group 0.000 claims description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 125000002883 imidazolyl group Chemical group 0.000 claims description 26
- 150000002431 hydrogen Chemical group 0.000 claims description 25
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims description 23
- 125000005265 dialkylamine group Chemical group 0.000 claims description 22
- 125000003003 spiro group Chemical group 0.000 claims description 22
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 20
- 150000003973 alkyl amines Chemical group 0.000 claims description 17
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 125000002541 furyl group Chemical group 0.000 claims description 16
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 16
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 16
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 16
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 16
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
- 125000001544 thienyl group Chemical group 0.000 claims description 15
- 125000001425 triazolyl group Chemical group 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000006413 ring segment Chemical group 0.000 claims description 14
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 230000002829 reductive effect Effects 0.000 claims description 13
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 13
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims description 12
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 12
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000002971 oxazolyl group Chemical group 0.000 claims description 11
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 10
- 150000001408 amides Chemical group 0.000 claims description 10
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000000532 dioxanyl group Chemical group 0.000 claims description 10
- 125000005411 dithiolanyl group Chemical group S1SC(CC1)* 0.000 claims description 10
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 10
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 9
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 9
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 9
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- 208000006673 asthma Diseases 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 230000003213 activating effect Effects 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 239000012279 sodium borohydride Substances 0.000 claims description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 5
- 150000001805 chlorine compounds Chemical group 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 208000024891 symptom Diseases 0.000 claims description 5
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 4
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
- 201000009961 allergic asthma Diseases 0.000 claims description 4
- 201000010105 allergic rhinitis Diseases 0.000 claims description 4
- 230000002862 amidating effect Effects 0.000 claims description 4
- 125000006242 amine protecting group Chemical group 0.000 claims description 4
- 201000008937 atopic dermatitis Diseases 0.000 claims description 4
- 150000003857 carboxamides Chemical class 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- GVZYNAKETPFKJX-IPBJYNAHSA-N n-[(2r,4s)-1-[4-(1-acetylpiperidin-4-yl)benzoyl]-2-methyl-3,4-dihydro-2h-quinolin-4-yl]-n-phenylpropanamide Chemical compound N1([C@H](C)C[C@@H](C2=CC=CC=C21)N(C(=O)CC)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1CCN(C(C)=O)CC1 GVZYNAKETPFKJX-IPBJYNAHSA-N 0.000 claims description 4
- GVZYNAKETPFKJX-GTYOFVGBSA-N n-[(2s,4r)-1-[4-(1-acetylpiperidin-4-yl)benzoyl]-2-methyl-3,4-dihydro-2h-quinolin-4-yl]-n-phenylpropanamide Chemical compound N1([C@@H](C)C[C@H](C2=CC=CC=C21)N(C(=O)CC)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1C1CCN(C(C)=O)CC1 GVZYNAKETPFKJX-GTYOFVGBSA-N 0.000 claims description 4
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 4
- FDOTXFNLSLBDTN-SSOJOUAXSA-N 2-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCC(N)=O)=CC=1)C)C1=CC=C(Cl)C=C1 FDOTXFNLSLBDTN-SSOJOUAXSA-N 0.000 claims description 3
- 125000006241 alcohol protecting group Chemical group 0.000 claims description 3
- 230000009435 amidation Effects 0.000 claims description 3
- 238000007112 amidation reaction Methods 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000006244 carboxylic acid protecting group Chemical group 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- MYNJXBPKZIIXFQ-SEODVWCLSA-N (e)-4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]-2-methylbut-2-enoic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OC\C=C(/C)C(O)=O)=CC=1)C)C1=CC=C(Cl)C=C1 MYNJXBPKZIIXFQ-SEODVWCLSA-N 0.000 claims description 2
- IKFWMKOHWYZDQL-TVLSLMGLSA-N (e)-4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]but-2-enoic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OC\C=C\C(O)=O)=CC=1)C)C1=CC=C(Cl)C=C1 IKFWMKOHWYZDQL-TVLSLMGLSA-N 0.000 claims description 2
- YOFFHWXQNYMXFJ-WTYVLRPYSA-N 2-[1-[[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]methyl]cyclopropyl]acetic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCC2(CC(O)=O)CC2)=CC=1)C)C1=CC=C(Cl)C=C1 YOFFHWXQNYMXFJ-WTYVLRPYSA-N 0.000 claims description 2
- BQJGVHWVXZKZEY-UZTOHYMASA-N 2-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]-n,n-dimethylacetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCC(=O)N(C)C)=CC=1)C)C1=CC=C(Cl)C=C1 BQJGVHWVXZKZEY-UZTOHYMASA-N 0.000 claims description 2
- QIPRXZAQYIVAPZ-HFJWLAOPSA-N 2-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]-n-methylacetamide Chemical compound C1=CC(OCC(=O)NC)=CC=C1C(=O)N1C2=CC=CC=C2[C@H](N(C(C)=O)C=2C=CC(Cl)=CC=2)C[C@@H]1C QIPRXZAQYIVAPZ-HFJWLAOPSA-N 0.000 claims description 2
- GEDURGDVMGWBKJ-SSOJOUAXSA-N 2-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]acetic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCC(O)=O)=CC=1)C)C1=CC=C(Cl)C=C1 GEDURGDVMGWBKJ-SSOJOUAXSA-N 0.000 claims description 2
- QYSLCJRJTURRSH-CQDCDSLLSA-N 2-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]butanoic acid Chemical compound C1=CC(OC(CC)C(O)=O)=CC=C1C(=O)N1C2=CC=CC=C2[C@H](N(C(C)=O)C=2C=CC(Cl)=CC=2)C[C@@H]1C QYSLCJRJTURRSH-CQDCDSLLSA-N 0.000 claims description 2
- NJANRWXDQGTOQC-KCWXNJEJSA-N 2-[4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenyl]piperazin-1-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(=CC=1)N1CCN(CC(N)=O)CC1)C)C1=CC=C(Cl)C=C1 NJANRWXDQGTOQC-KCWXNJEJSA-N 0.000 claims description 2
- DDUFMGXTZYMTAG-KCWXNJEJSA-N 2-[4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenyl]piperazin-1-yl]acetic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(=CC=1)N1CCN(CC(O)=O)CC1)C)C1=CC=C(Cl)C=C1 DDUFMGXTZYMTAG-KCWXNJEJSA-N 0.000 claims description 2
- MHKWOVKKERULHT-UZTOHYMASA-N 3-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]-2,2-dimethylpropanoic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCC(C)(C)C(O)=O)=CC=1)C)C1=CC=C(Cl)C=C1 MHKWOVKKERULHT-UZTOHYMASA-N 0.000 claims description 2
- IBTYRMFHNAPPFG-HFJWLAOPSA-N 3-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]propanoic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCC(O)=O)=CC=1)C)C1=CC=C(Cl)C=C1 IBTYRMFHNAPPFG-HFJWLAOPSA-N 0.000 claims description 2
- YZWCZPGTCFVCGQ-HFJWLAOPSA-N 3-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenyl]prop-2-enoic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(C=CC(O)=O)=CC=1)C)C1=CC=C(Cl)C=C1 YZWCZPGTCFVCGQ-HFJWLAOPSA-N 0.000 claims description 2
- NNVFFZXAXQPCAQ-HFJWLAOPSA-N 3-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenyl]propanoic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(CCC(O)=O)=CC=1)C)C1=CC=C(Cl)C=C1 NNVFFZXAXQPCAQ-HFJWLAOPSA-N 0.000 claims description 2
- SAQMCTQCHVYQHD-MRDQGFSESA-N 3-[5-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]benzotriazol-1-yl]propanoic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=C2N=NN(CCC(O)=O)C2=CC=1)C)C1=CC=C(Cl)C=C1 SAQMCTQCHVYQHD-MRDQGFSESA-N 0.000 claims description 2
- UWDWHDGTRODOLF-UZTOHYMASA-N 4-[3-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]butanoic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=C(OCCCC(O)=O)C=CC=1)C)C1=CC=C(Cl)C=C1 UWDWHDGTRODOLF-UZTOHYMASA-N 0.000 claims description 2
- WWHXNUCBACSWGB-WTYVLRPYSA-N 4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]-2,2-dimethylbutanoic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCC(C)(C)C(O)=O)=CC=1)C)C1=CC=C(Cl)C=C1 WWHXNUCBACSWGB-WTYVLRPYSA-N 0.000 claims description 2
- JRBCECRZQLWQGZ-WTYVLRPYSA-N 4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]-n-methylsulfonylbutanamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCCC(=O)NS(C)(=O)=O)=CC=1)C)C1=CC=C(Cl)C=C1 JRBCECRZQLWQGZ-WTYVLRPYSA-N 0.000 claims description 2
- BXHFEROUHXMLBU-UZTOHYMASA-N 4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]butanamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCCC(N)=O)=CC=1)C)C1=CC=C(Cl)C=C1 BXHFEROUHXMLBU-UZTOHYMASA-N 0.000 claims description 2
- QUOVKFJXUZYQCH-UZTOHYMASA-N 4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]butanoic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCCC(O)=O)=CC=1)C)C1=CC=C(Cl)C=C1 QUOVKFJXUZYQCH-UZTOHYMASA-N 0.000 claims description 2
- JGGATBKKJVQSMZ-UZTOHYMASA-N 4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenyl]but-3-ynoic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(=CC=1)C#CCC(O)=O)C)C1=CC=C(Cl)C=C1 JGGATBKKJVQSMZ-UZTOHYMASA-N 0.000 claims description 2
- 208000019693 Lung disease Diseases 0.000 claims description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical group C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Chemical group C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 2
- OCWIPLFUGDWWBH-KCWXNJEJSA-N ethyl 4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]butanoate Chemical compound C1=CC(OCCCC(=O)OCC)=CC=C1C(=O)N1C2=CC=CC=C2[C@H](N(C(C)=O)C=2C=CC(Cl)=CC=2)C[C@@H]1C OCWIPLFUGDWWBH-KCWXNJEJSA-N 0.000 claims description 2
- OYXNDYGVPQTLSX-WKRVVKTRSA-N ethyl 4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1OC1=CC=C(C(=O)N2C3=CC=CC=C3[C@H](N(C(C)=O)C=3C=CC(Cl)=CC=3)C[C@@H]2C)C=C1 OYXNDYGVPQTLSX-WKRVVKTRSA-N 0.000 claims description 2
- PVNIOTAOKRSNFJ-WKRVVKTRSA-N ethyl 4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenyl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C=CC(=CC=2)C(=O)N2C3=CC=CC=C3[C@H](N(C(C)=O)C=3C=CC(Cl)=CC=3)C[C@@H]2C)=C1 PVNIOTAOKRSNFJ-WKRVVKTRSA-N 0.000 claims description 2
- MIQKAQDXRJFRIF-WKRVVKTRSA-N ethyl 4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1C1=CC=C(C(=O)N2C3=CC=CC=C3[C@H](N(C(C)=O)C=3C=CC(Cl)=CC=3)C[C@@H]2C)C=C1 MIQKAQDXRJFRIF-WKRVVKTRSA-N 0.000 claims description 2
- YQYPROOPLJUFPI-MRDQGFSESA-N n-(4-chlorophenyl)-n-[(2s,4r)-1-(3-ethyl-4-fluorobenzoyl)-2-methyl-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound C1=C(F)C(CC)=CC(C(=O)N2C3=CC=CC=C3[C@H](N(C(C)=O)C=3C=CC(Cl)=CC=3)C[C@@H]2C)=C1 YQYPROOPLJUFPI-MRDQGFSESA-N 0.000 claims description 2
- GAMRYPOQGWDVEW-XDBZFTIUSA-N n-(4-chlorophenyl)-n-[(2s,4r)-1-[1-(2-hydroxyethyl)-2-methylbenzimidazole-5-carbonyl]-2-methyl-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=C2N=C(C)N(CCO)C2=CC=1)C)C1=CC=C(Cl)C=C1 GAMRYPOQGWDVEW-XDBZFTIUSA-N 0.000 claims description 2
- NBTUCIVMPQYTGB-KCWXNJEJSA-N n-(4-chlorophenyl)-n-[(2s,4r)-1-[4-(2-imidazol-1-ylethoxy)benzoyl]-2-methyl-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCN2C=NC=C2)=CC=1)C)C1=CC=C(Cl)C=C1 NBTUCIVMPQYTGB-KCWXNJEJSA-N 0.000 claims description 2
- XKMACZHGKKQFJI-SMSORMJASA-N n-(4-chlorophenyl)-n-[(2s,4r)-1-[4-(4-ethylpiperazin-1-yl)benzoyl]-2-methyl-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound C1CN(CC)CCN1C1=CC=C(C(=O)N2C3=CC=CC=C3[C@H](N(C(C)=O)C=3C=CC(Cl)=CC=3)C[C@@H]2C)C=C1 XKMACZHGKKQFJI-SMSORMJASA-N 0.000 claims description 2
- ZBRYOATWAXJEAE-KCWXNJEJSA-N n-(4-chlorophenyl)-n-[(2s,4r)-1-[4-(4-hydroxy-4-methylpentoxy)benzoyl]-2-methyl-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCCC(C)(C)O)=CC=1)C)C1=CC=C(Cl)C=C1 ZBRYOATWAXJEAE-KCWXNJEJSA-N 0.000 claims description 2
- DBHMVQQKHLKMQS-JPQMRUPTSA-N n-(4-chlorophenyl)-n-[(2s,4r)-1-[4-[(1-ethylpiperidin-4-yl)methoxy]benzoyl]-2-methyl-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound C1CN(CC)CCC1COC1=CC=C(C(=O)N2C3=CC=CC=C3[C@H](N(C(C)=O)C=3C=CC(Cl)=CC=3)C[C@@H]2C)C=C1 DBHMVQQKHLKMQS-JPQMRUPTSA-N 0.000 claims description 2
- JOJXYNVETNDWAE-XRHLQHRESA-N n-(4-chlorophenyl)-n-[(2s,4r)-2-methyl-1-(1-propan-2-ylbenzotriazole-5-carbonyl)-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@H](C)N(C2=CC=CC=C21)C(=O)C=1C=C2N=NN(C2=CC=1)C(C)C)C1=CC=C(Cl)C=C1 JOJXYNVETNDWAE-XRHLQHRESA-N 0.000 claims description 2
- OBFHBOMTGQMMMP-HMILPKGGSA-N n-(4-chlorophenyl)-n-[(2s,4r)-2-methyl-1-(1-propan-2-ylindazole-5-carbonyl)-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@H](C)N(C2=CC=CC=C21)C(=O)C=1C=C2C=NN(C2=CC=1)C(C)C)C1=CC=C(Cl)C=C1 OBFHBOMTGQMMMP-HMILPKGGSA-N 0.000 claims description 2
- GVEOBLPWWROVPY-AVRWGWEMSA-N n-(4-chlorophenyl)-n-[(2s,4r)-2-methyl-1-(4-methyl-2,3-dihydro-1,4-benzoxazine-6-carbonyl)-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=C2N(C)CCOC2=CC=1)C)C1=CC=C(Cl)C=C1 GVEOBLPWWROVPY-AVRWGWEMSA-N 0.000 claims description 2
- FQIAUPBNQYRZAS-HFJWLAOPSA-N n-(4-chlorophenyl)-n-[(2s,4r)-2-methyl-1-(4-methyl-2,3-dihydro-1,4-benzoxazine-7-carbonyl)-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=C2OCCN(C)C2=CC=1)C)C1=CC=C(Cl)C=C1 FQIAUPBNQYRZAS-HFJWLAOPSA-N 0.000 claims description 2
- DPZKMOKBMZFFQP-WTYVLRPYSA-N n-(4-chlorophenyl)-n-[(2s,4r)-2-methyl-1-(4-morpholin-4-ylbenzoyl)-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(=CC=1)N1CCOCC1)C)C1=CC=C(Cl)C=C1 DPZKMOKBMZFFQP-WTYVLRPYSA-N 0.000 claims description 2
- QSSUMUXXQGCLKR-WTYVLRPYSA-N n-(4-chlorophenyl)-n-[(2s,4r)-2-methyl-1-(4-pyrrolidin-1-ylbenzoyl)-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(=CC=1)N1CCCC1)C)C1=CC=C(Cl)C=C1 QSSUMUXXQGCLKR-WTYVLRPYSA-N 0.000 claims description 2
- YJOKNNZIJPFKLM-AFMDSPMNSA-N n-(4-chlorophenyl)-n-[(2s,4r)-2-methyl-1-(6-morpholin-4-ylpyridine-3-carbonyl)-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=NC(=CC=1)N1CCOCC1)C)C1=CC=C(Cl)C=C1 YJOKNNZIJPFKLM-AFMDSPMNSA-N 0.000 claims description 2
- DEQIPTYPRGZPAE-SMSORMJASA-N n-(4-chlorophenyl)-n-[(2s,4r)-2-methyl-1-[4-(2-morpholin-4-ylethoxy)benzoyl]-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCN2CCOCC2)=CC=1)C)C1=CC=C(Cl)C=C1 DEQIPTYPRGZPAE-SMSORMJASA-N 0.000 claims description 2
- LFOQCXCVJPTIBC-GTYOFVGBSA-N n-(4-chlorophenyl)-n-[(2s,4r)-2-methyl-1-[4-(3-morpholin-4-ylprop-1-ynyl)benzoyl]-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(=CC=1)C#CCN1CCOCC1)C)C1=CC=C(Cl)C=C1 LFOQCXCVJPTIBC-GTYOFVGBSA-N 0.000 claims description 2
- TWLBIXOEHJNUPU-GTYOFVGBSA-N n-(4-chlorophenyl)-n-[(2s,4r)-2-methyl-1-[4-(3-morpholin-4-ylpropoxy)benzoyl]-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCCN2CCOCC2)=CC=1)C)C1=CC=C(Cl)C=C1 TWLBIXOEHJNUPU-GTYOFVGBSA-N 0.000 claims description 2
- ORLGTFOCUKNUPI-GTYOFVGBSA-N n-(4-chlorophenyl)-n-[(2s,4r)-2-methyl-1-[4-(3-pyrrolidin-1-ylpropoxy)benzoyl]-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCCN2CCCC2)=CC=1)C)C1=CC=C(Cl)C=C1 ORLGTFOCUKNUPI-GTYOFVGBSA-N 0.000 claims description 2
- JOPNUWHFQLIZQB-GTYOFVGBSA-N n-(4-chlorophenyl)-n-[(2s,4r)-2-methyl-1-[4-(4-oxo-4-pyrrolidin-1-ylbutoxy)benzoyl]-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCCC(=O)N2CCCC2)=CC=1)C)C1=CC=C(Cl)C=C1 JOPNUWHFQLIZQB-GTYOFVGBSA-N 0.000 claims description 2
- NVLZBCXEXAVWKZ-AFJIDDCJSA-N n-(4-chlorophenyl)-n-[(2s,4r)-2-methyl-1-[4-(4-oxopentoxy)benzoyl]-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCCC(C)=O)=CC=1)C)C1=CC=C(Cl)C=C1 NVLZBCXEXAVWKZ-AFJIDDCJSA-N 0.000 claims description 2
- MLIROKNSRPDFFE-URAOTHONSA-N n-(4-chlorophenyl)-n-[(2s,4r)-2-methyl-1-[4-(pyridin-4-ylmethoxy)benzoyl]-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCC=2C=CN=CC=2)=CC=1)C)C1=CC=C(Cl)C=C1 MLIROKNSRPDFFE-URAOTHONSA-N 0.000 claims description 2
- FDGWTCHRXDHEQQ-KCWXNJEJSA-N n-(4-chlorophenyl)-n-[(2s,4r)-2-methyl-1-[4-[2-(2-oxopyrrolidin-1-yl)ethoxy]benzoyl]-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCN2C(CCC2)=O)=CC=1)C)C1=CC=C(Cl)C=C1 FDGWTCHRXDHEQQ-KCWXNJEJSA-N 0.000 claims description 2
- QNYRCEHOWBOKCU-WTYVLRPYSA-N n-(4-chlorophenyl)-n-[(2s,4r)-2-methyl-1-[4-[3-(1,2,4-oxadiazol-5-yl)propoxy]benzoyl]-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCCC=2ON=CN=2)=CC=1)C)C1=CC=C(Cl)C=C1 QNYRCEHOWBOKCU-WTYVLRPYSA-N 0.000 claims description 2
- DVMOLUSGVLUMSS-UZTOHYMASA-N n-(4-chlorophenyl)-n-[(2s,4r)-2-methyl-1-[4-[3-(2h-tetrazol-5-yl)propoxy]benzoyl]-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCCC2=NNN=N2)=CC=1)C)C1=CC=C(Cl)C=C1 DVMOLUSGVLUMSS-UZTOHYMASA-N 0.000 claims description 2
- BTWPTPJDCHKDFT-UZTOHYMASA-N n-(4-chlorophenyl)-n-[(2s,4r)-2-methyl-1-[4-[3-(trifluoromethylsulfonylamino)propoxy]benzoyl]-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCCNS(=O)(=O)C(F)(F)F)=CC=1)C)C1=CC=C(Cl)C=C1 BTWPTPJDCHKDFT-UZTOHYMASA-N 0.000 claims description 2
- AFAMKVNLVFKPFJ-DFHRPNOPSA-N n-[(2r,4s)-2-methyl-1-(4-morpholin-4-ylbenzoyl)-3,4-dihydro-2h-quinolin-4-yl]-n-phenylpropanamide Chemical compound N1([C@H](C)C[C@@H](C2=CC=CC=C21)N(C(=O)CC)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1N1CCOCC1 AFAMKVNLVFKPFJ-DFHRPNOPSA-N 0.000 claims description 2
- JBHNSBWUCPQXTI-GAJHUEQPSA-N n-[(2s,4r)-1-(1,3-benzodioxole-5-carbonyl)-2-methyl-3,4-dihydro-2h-quinolin-4-yl]-n-phenylacetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=C2OCOC2=CC=1)C)C1=CC=CC=C1 JBHNSBWUCPQXTI-GAJHUEQPSA-N 0.000 claims description 2
- NYSSDSIPSIOQJT-QMHKHESXSA-N n-[(2s,4r)-1-(1,3-benzothiazole-2-carbonyl)-2-methyl-3,4-dihydro-2h-quinolin-4-yl]-n-(4-chlorophenyl)acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1SC2=CC=CC=C2N=1)C)C1=CC=C(Cl)C=C1 NYSSDSIPSIOQJT-QMHKHESXSA-N 0.000 claims description 2
- WNFVAOPXTRPJRO-UPCLLVRISA-N n-[(2s,4r)-1-(1h-benzimidazole-2-carbonyl)-2-methyl-3,4-dihydro-2h-quinolin-4-yl]-n-(4-chlorophenyl)acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1NC2=CC=CC=C2N=1)C)C1=CC=C(Cl)C=C1 WNFVAOPXTRPJRO-UPCLLVRISA-N 0.000 claims description 2
- FMIGRDUONXPRRE-JCOAXYOVSA-N n-[(2s,4r)-1-[4-(1-acetylpiperidin-4-yl)benzoyl]-2-methyl-3,4-dihydro-2h-quinolin-4-yl]-n-(4-chlorophenyl)acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(=CC=1)C1CCN(CC1)C(C)=O)C)C1=CC=C(Cl)C=C1 FMIGRDUONXPRRE-JCOAXYOVSA-N 0.000 claims description 2
- MJGYDGCOWLLVOY-JCOAXYOVSA-N n-[(2s,4r)-1-[4-(1-acetylpiperidin-4-yl)oxybenzoyl]-2-methyl-3,4-dihydro-2h-quinolin-4-yl]-n-(4-chlorophenyl)acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OC2CCN(CC2)C(C)=O)=CC=1)C)C1=CC=C(Cl)C=C1 MJGYDGCOWLLVOY-JCOAXYOVSA-N 0.000 claims description 2
- CCYPFNSRUWCIKN-UZTOHYMASA-N n-[(2s,4r)-1-[4-(3-aminopropoxy)benzoyl]-2-methyl-3,4-dihydro-2h-quinolin-4-yl]-n-(4-chlorophenyl)acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCCN)=CC=1)C)C1=CC=C(Cl)C=C1 CCYPFNSRUWCIKN-UZTOHYMASA-N 0.000 claims description 2
- LMQJKGGQNBQEHJ-URAOTHONSA-N n-[(2s,4r)-1-[4-(4-acetylpiperazin-1-yl)benzoyl]-2-methyl-3,4-dihydro-2h-quinolin-4-yl]-n-(4-chlorophenyl)acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(=CC=1)N1CCN(CC1)C(C)=O)C)C1=CC=C(Cl)C=C1 LMQJKGGQNBQEHJ-URAOTHONSA-N 0.000 claims description 2
- FCOUPZCZSXOACF-AVRWGWEMSA-N n-[(2s,4r)-2-methyl-1-(3-methyl-1-benzofuran-2-carbonyl)-3,4-dihydro-2h-quinolin-4-yl]-n-phenylacetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C1=C(C2=CC=CC=C2O1)C)C)C1=CC=CC=C1 FCOUPZCZSXOACF-AVRWGWEMSA-N 0.000 claims description 2
- AFAMKVNLVFKPFJ-RBISFHTESA-N n-[(2s,4r)-2-methyl-1-(4-morpholin-4-ylbenzoyl)-3,4-dihydro-2h-quinolin-4-yl]-n-phenylpropanamide Chemical compound N1([C@@H](C)C[C@H](C2=CC=CC=C21)N(C(=O)CC)C=1C=CC=CC=1)C(=O)C(C=C1)=CC=C1N1CCOCC1 AFAMKVNLVFKPFJ-RBISFHTESA-N 0.000 claims description 2
- 230000000414 obstructive effect Effects 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 17
- 150000001413 amino acids Chemical class 0.000 claims 5
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- SOQFZXMZMHODLD-UHFFFAOYSA-N 1,2,5-thiadiazolidine Chemical compound C1CNSN1 SOQFZXMZMHODLD-UHFFFAOYSA-N 0.000 claims 1
- DGHGGOVGSHVFRP-HFJWLAOPSA-N 3-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]propanamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCC(N)=O)=CC=1)C)C1=CC=C(Cl)C=C1 DGHGGOVGSHVFRP-HFJWLAOPSA-N 0.000 claims 1
- KIIZKTUGCNEFSQ-WTYVLRPYSA-N 4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]-2,2-dimethylbutanamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCC(C)(C)C(N)=O)=CC=1)C)C1=CC=C(Cl)C=C1 KIIZKTUGCNEFSQ-WTYVLRPYSA-N 0.000 claims 1
- NNLOAUIUNCBHDH-KCWXNJEJSA-N 4-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]-n-ethylbutanamide Chemical compound C1=CC(OCCCC(=O)NCC)=CC=C1C(=O)N1C2=CC=CC=C2[C@H](N(C(C)=O)C=2C=CC(Cl)=CC=2)C[C@@H]1C NNLOAUIUNCBHDH-KCWXNJEJSA-N 0.000 claims 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- GXVAJPCOFBWJAM-WTYVLRPYSA-N n-(4-chlorophenyl)-n-[(2s,4r)-1-[4-(3-cyanopropoxy)benzoyl]-2-methyl-3,4-dihydro-2h-quinolin-4-yl]acetamide Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(OCCCC#N)=CC=1)C)C1=CC=C(Cl)C=C1 GXVAJPCOFBWJAM-WTYVLRPYSA-N 0.000 claims 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
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- 238000002054 transplantation Methods 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 1
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
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Classifications
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- C07D215/02—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
- 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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- A61K31/47—Quinolines; Isoquinolines
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—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
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Endocrinology (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Transplantation (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Vascular Medicine (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US56041004P | 2004-04-07 | 2004-04-07 | |
US60/560,410 | 2004-04-07 | ||
PCT/US2005/011643 WO2005100321A1 (en) | 2004-04-07 | 2005-04-07 | Pgd2 receptor antagonists for the treatment of inflammatory diseases |
Publications (1)
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CA2561564A1 true CA2561564A1 (en) | 2005-10-27 |
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Family Applications (1)
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CA002561564A Abandoned CA2561564A1 (en) | 2004-04-07 | 2005-04-07 | Pgd2 receptor antagonists for the treatment of inflammatory diseases |
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EP (1) | EP1740547A1 (no) |
JP (1) | JP2007532555A (no) |
KR (1) | KR20070002085A (no) |
CN (1) | CN101018770A (no) |
AR (1) | AR048528A1 (no) |
AU (1) | AU2005233125A1 (no) |
BR (1) | BRPI0509668A (no) |
CA (1) | CA2561564A1 (no) |
CL (1) | CL2008000069A1 (no) |
CR (1) | CR8659A (no) |
EC (1) | ECSP066977A (no) |
IL (1) | IL178328A0 (no) |
MA (1) | MA28566B1 (no) |
MX (1) | MXPA06011540A (no) |
NO (1) | NO20065107L (no) |
RU (1) | RU2006138603A (no) |
TN (1) | TNSN06320A1 (no) |
TW (1) | TW200538127A (no) |
UA (1) | UA84749C2 (no) |
WO (1) | WO2005100321A1 (no) |
ZA (1) | ZA200608955B (no) |
Families Citing this family (29)
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MX2007010215A (es) | 2005-02-24 | 2007-11-07 | Millennium Pharm Inc | Antagonistas del receptor pgd2 para el tratamiento de enfermedades inflamatorias. |
EP1717235A3 (en) * | 2005-04-29 | 2007-02-28 | Bioprojet | Phenoxypropylpiperidines and -pyrrolidines and their use as histamine H3-receptor ligands |
EP1917255A2 (en) | 2005-07-29 | 2008-05-07 | F. Hoffmann-Roche AG | Indol-3-yl-carbonyl-piperidin and piperazin derivatives |
PL2037967T3 (pl) | 2006-06-16 | 2017-07-31 | The Trustees Of The University Of Pennsylvania | Antagoniści receptora prostaglandyny D2 w leczeniu łysienia androgenowego |
BRPI0719122A2 (pt) | 2006-08-24 | 2013-12-10 | Novartis Ag | Compostos orgânicos |
EP2060563A4 (en) | 2006-09-08 | 2010-12-22 | Dainippon Sumitomo Pharma Co | CYCLIC AMINOALKYLCARBOXAMIDE DERIVATIVE |
CA2662574A1 (en) | 2006-09-22 | 2008-03-27 | Novartis Ag | Heterocyclic organic compounds |
EA200900820A1 (ru) | 2006-12-20 | 2010-02-26 | Новартис Аг | 2-замещенные 5-членные гетероциклы в качестве ингибиторов стеароил-соа-десатуразы (ссд) |
EP2199283A1 (en) | 2007-09-27 | 2010-06-23 | Kowa Company, Ltd. | Prophylactic and/or therapeutic agent for anemia, comprising tetrahydroquinoline compound as active ingredient |
DK2229358T3 (da) | 2007-12-14 | 2011-07-04 | Pulmagen Therapeutics Asthma Ltd | Indoler og deres terapeutiske anvendelse |
JP2011102241A (ja) * | 2008-03-04 | 2011-05-26 | Dainippon Sumitomo Pharma Co Ltd | 新規1−アミノカルボニルピペリジン誘導体 |
KR101660059B1 (ko) | 2008-08-22 | 2016-09-26 | 박스알타 인코퍼레이티드 | 중합체 벤질 카르보네이트-유도체 |
JP2011256110A (ja) * | 2008-09-30 | 2011-12-22 | Takeda Chem Ind Ltd | ヘキサヒドロピロロキノリンの製造法 |
JP5572154B2 (ja) | 2009-03-31 | 2014-08-13 | 興和株式会社 | テトラヒドロキノリン化合物を有効成分とする貧血の予防及び/又は治療剤 |
GB0919431D0 (en) | 2009-11-05 | 2009-12-23 | Glaxosmithkline Llc | Novel compounds |
EP2496945B1 (en) | 2009-11-05 | 2015-04-01 | GlaxoSmithKline LLC | Novel process |
KR101920090B1 (ko) | 2010-07-05 | 2018-11-19 | 이도르시아 파마슈티컬스 리미티드 | 1-페닐-치환된 헤테로시클릴 유도체 및 프로스타글란딘 d2 수용체 조절자로서 이의 용도 |
EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
ES2613644T3 (es) | 2011-06-17 | 2017-05-25 | Merck Sharp & Dohme Corp. | Tetrahidroquinolinas condensadas con cicloalquilo como moduladores del receptor CRTH2 |
KR20140113667A (ko) | 2011-12-16 | 2014-09-24 | 아토픽스 테라퓨릭스 리미티드 | 호산구성 식도염의 치료를 위한 crth2 길항제 및 양성자 펌프 저해제의 조합 |
AR089360A1 (es) | 2011-12-21 | 2014-08-20 | Actelion Pharmaceuticals Ltd | Derivados de heterociclilo y su uso como moduladores del receptor d₂ de prostaglandina |
JP6127135B2 (ja) | 2012-07-05 | 2017-05-10 | アクテリオン ファーマシューティカルズ リミテッドActelion Pharmaceuticals Ltd | 1−フェニル置換ヘテロシクリル誘導体及びプロスタグランジンd2受容体調節剤としてのそれらの使用 |
EP3256121B1 (en) | 2015-02-13 | 2024-08-07 | INSERM - Institut National de la Santé et de la Recherche Médicale | Ptgdr-1 and/or ptgdr-2 antagonists for preventing and/or treating systemic lupus erythematosus |
US20200078351A1 (en) | 2015-07-30 | 2020-03-12 | The Trustees Of The University Of Pennsylvania | Single nucleotide polymorphic alleles of human dp-2 gene for detection of susceptibility to hair growth inhibition by pgd2 |
JOP20190105A1 (ar) * | 2016-11-16 | 2019-05-09 | Lundbeck La Jolla Research Center Inc | مثبطات أحادي أسيل جليسرول ليباز (magl) |
RS65621B1 (sr) | 2018-04-18 | 2024-07-31 | Constellation Pharmaceuticals Inc | Modulatori enzima koji modifikuju metil, sastavi i njihova upotreba |
WO2019226491A1 (en) | 2018-05-21 | 2019-11-28 | Constellation Pharmaceuticals, Inc. | Modulators of methyl modifying enzymes, compositions and uses thereof |
CN113201316B (zh) * | 2021-04-25 | 2022-08-26 | 西南石油大学 | 温度/CO2/pH多重响应性乳化剂和乳状液及其应用 |
CN116425623B (zh) * | 2023-04-10 | 2024-02-13 | 大连凯飞化学股份有限公司 | 一锅法合成3,5-二氯-4-甲基苯甲酸的方法 |
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AU745129B2 (en) * | 1998-03-31 | 2002-03-14 | Shionogi & Co., Ltd. | Process for producing 5-hydroxybenzo(b)thiophene-3- carboxylic acid derivatives |
CZ20032900A3 (cs) * | 2001-04-30 | 2004-06-16 | Pfizer Products Inc. | Sloučeniny vhodné jako meziprodukty |
JP2003321471A (ja) * | 2002-04-30 | 2003-11-11 | Fuji Photo Film Co Ltd | ラクタム化合物及びその製造方法 |
US20040053842A1 (en) * | 2002-07-02 | 2004-03-18 | Pfizer Inc. | Methods of treatment with CETP inhibitors and antihypertensive agents |
BR0315041A (pt) * | 2002-10-04 | 2005-08-16 | Millennium Pharm Inc | Métodos para inibir crth2 em um indivìduo que necessita inibição de crth2; composto; e composição farmacêutica |
EP1556356B1 (en) * | 2002-10-21 | 2006-05-31 | Warner-Lambert Company LLC | Tetrahydroquinoline derivatives as crth2 antagonists |
AU2003289207A1 (en) * | 2002-12-06 | 2004-06-30 | Kyowa Hakko Kogyo Co., Ltd. | Anti-inflammatory agent |
EP1435356A1 (en) * | 2003-01-06 | 2004-07-07 | Warner-Lambert Company LLC | Quinoline derivatives as CRTH2 antagonists |
-
2005
- 2005-04-07 JP JP2007507467A patent/JP2007532555A/ja active Pending
- 2005-04-07 WO PCT/US2005/011643 patent/WO2005100321A1/en active Application Filing
- 2005-04-07 EP EP05733968A patent/EP1740547A1/en not_active Withdrawn
- 2005-04-07 KR KR1020067023323A patent/KR20070002085A/ko not_active Application Discontinuation
- 2005-04-07 TW TW094111008A patent/TW200538127A/zh unknown
- 2005-04-07 UA UAA200611678A patent/UA84749C2/ru unknown
- 2005-04-07 AR ARP050101369A patent/AR048528A1/es unknown
- 2005-04-07 AU AU2005233125A patent/AU2005233125A1/en not_active Withdrawn
- 2005-04-07 CA CA002561564A patent/CA2561564A1/en not_active Abandoned
- 2005-04-07 CN CNA200580018590XA patent/CN101018770A/zh active Pending
- 2005-04-07 RU RU2006138603/04A patent/RU2006138603A/ru not_active Application Discontinuation
- 2005-04-07 MX MXPA06011540A patent/MXPA06011540A/es not_active Application Discontinuation
- 2005-04-07 BR BRPI0509668-5A patent/BRPI0509668A/pt not_active IP Right Cessation
-
2006
- 2006-09-27 IL IL178328A patent/IL178328A0/en unknown
- 2006-09-27 CR CR8659A patent/CR8659A/es not_active Application Discontinuation
- 2006-10-06 TN TNP2006000320A patent/TNSN06320A1/en unknown
- 2006-10-27 ZA ZA200608955A patent/ZA200608955B/xx unknown
- 2006-11-02 MA MA29430A patent/MA28566B1/fr unknown
- 2006-11-06 NO NO20065107A patent/NO20065107L/no not_active Application Discontinuation
- 2006-11-08 EC EC2006006977A patent/ECSP066977A/es unknown
-
2008
- 2008-01-10 CL CL200800069A patent/CL2008000069A1/es unknown
Also Published As
Publication number | Publication date |
---|---|
JP2007532555A (ja) | 2007-11-15 |
ZA200608955B (en) | 2009-05-27 |
IL178328A0 (en) | 2007-02-11 |
CR8659A (es) | 2007-06-08 |
CN101018770A (zh) | 2007-08-15 |
RU2006138603A (ru) | 2008-05-20 |
MA28566B1 (fr) | 2007-05-02 |
UA84749C2 (ru) | 2008-11-25 |
AU2005233125A1 (en) | 2005-10-27 |
TW200538127A (en) | 2005-12-01 |
CL2008000069A1 (es) | 2008-05-16 |
EP1740547A1 (en) | 2007-01-10 |
TNSN06320A1 (en) | 2008-02-22 |
AR048528A1 (es) | 2006-05-03 |
BRPI0509668A (pt) | 2007-10-09 |
ECSP066977A (es) | 2006-12-29 |
WO2005100321A1 (en) | 2005-10-27 |
KR20070002085A (ko) | 2007-01-04 |
NO20065107L (no) | 2006-12-01 |
MXPA06011540A (es) | 2007-01-26 |
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