JP2007532555A - 炎症性疾患の処置のためのｐｇｄ２レセプターアンタゴニスト - Google Patents

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Publication number

JP2007532555A

JP2007532555A JP2007507467A JP2007507467A JP2007532555A JP 2007532555 A JP2007532555 A JP 2007532555A JP 2007507467 A JP2007507467 A JP 2007507467A JP 2007507467 A JP2007507467 A JP 2007507467A JP 2007532555 A JP2007532555 A JP 2007532555A

Authority

JP

Japan

Prior art keywords

substituted

methyl

phenyl

group

haloalkyl

Prior art date

2004-04-07

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.)

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• 238000011282 treatment Methods 0.000 title claims abstract description 28
• 208000027866 inflammatory disease Diseases 0.000 title claims abstract description 16
• 108050000258 Prostaglandin D receptors Proteins 0.000 title abstract description 45
• 102000009389 Prostaglandin D receptors Human genes 0.000 title description 43
• 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 267
• 150000003839 salts Chemical class 0.000 claims abstract description 30
• -1 N-substituted nitrogen Chemical class 0.000 claims description 854
• 238000000034 method Methods 0.000 claims description 202
• 125000001188 haloalkyl group Chemical group 0.000 claims description 169
• 125000000217 alkyl group Chemical group 0.000 claims description 153
• 125000003118 aryl group Chemical group 0.000 claims description 129
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 119
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 114
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 101
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 86
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 74
• 125000001072 heteroaryl group Chemical group 0.000 claims description 72
• 229910052736 halogen Inorganic materials 0.000 claims description 66
• 150000002367 halogens Chemical class 0.000 claims description 65
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 64
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 63
• 229910052799 carbon Inorganic materials 0.000 claims description 55
• 238000006243 chemical reaction Methods 0.000 claims description 55
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
• 125000001424 substituent group Chemical group 0.000 claims description 48
• 229910052757 nitrogen Inorganic materials 0.000 claims description 42
• 125000002757 morpholinyl group Chemical group 0.000 claims description 41
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 41
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 39
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 39
• 125000002947 alkylene group Chemical group 0.000 claims description 35
• 150000001412 amines Chemical class 0.000 claims description 35
• 125000002950 monocyclic group Chemical group 0.000 claims description 35
• 229910052717 sulfur Inorganic materials 0.000 claims description 35
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 32
• 125000003386 piperidinyl group Chemical group 0.000 claims description 32
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 31
• 150000001721 carbon Chemical group 0.000 claims description 31
• 125000004432 carbon atom Chemical group C* 0.000 claims description 30
• 150000004820 halides Chemical class 0.000 claims description 30
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 29
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
• 125000004193 piperazinyl group Chemical group 0.000 claims description 27
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
• 125000002883 imidazolyl group Chemical group 0.000 claims description 26
• 125000003545 alkoxy group Chemical group 0.000 claims description 24
• 239000001257 hydrogen Substances 0.000 claims description 24
• 125000003003 spiro group Chemical group 0.000 claims description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims description 23
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 23
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 21
• 125000005265 dialkylamine group Chemical group 0.000 claims description 21
• 125000005843 halogen group Chemical group 0.000 claims description 21
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 21
• 125000000623 heterocyclic group Chemical group 0.000 claims description 20
• 125000000160 oxazolidinyl group Chemical group 0.000 claims description 19
• 125000001984 thiazolidinyl group Chemical group 0.000 claims description 18
• 150000003973 alkyl amines Chemical class 0.000 claims description 17
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 17
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 17
• 125000002837 carbocyclic group Chemical group 0.000 claims description 16
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 16
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
• 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
• 125000002541 furyl group Chemical group 0.000 claims description 15
• 125000004435 hydrogen atom Chemical class [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
• 239000003153 chemical reaction reagent Substances 0.000 claims description 14
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 14
• 125000006413 ring segment Chemical group 0.000 claims description 14
• 125000001425 triazolyl group Chemical group 0.000 claims description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 13
• 125000004076 pyridyl group Chemical group 0.000 claims description 13
• 230000002829 reductive effect Effects 0.000 claims description 13
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 12
• 150000001408 amides Chemical class 0.000 claims description 12
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 12
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 12
• 125000005879 dioxolanyl group Chemical group 0.000 claims description 11
• 125000005411 dithiolanyl group Chemical group S1SC(CC1)* 0.000 claims description 11
• 125000002971 oxazolyl group Chemical group 0.000 claims description 11
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 11
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 10
• 239000002253 acid Substances 0.000 claims description 10
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 10
• 125000000532 dioxanyl group Chemical group 0.000 claims description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 10
• 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
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 8
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 8
• 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 8
• 229940080818 propionamide Drugs 0.000 claims description 8
• 239000007858 starting material Substances 0.000 claims description 8
• 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 8
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
• YXFPJVYIHQCVNG-KDYSTLNUSA-N C(C)OC(COC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C(CC)=O)C1=CC=CC=C1)C)=O Chemical compound C(C)OC(COC1=CC=C(C=C1)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C(CC)=O)C1=CC=CC=C1)C)=O YXFPJVYIHQCVNG-KDYSTLNUSA-N 0.000 claims description 7
• 208000006673 asthma Diseases 0.000 claims description 7
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 7
• 125000000335 thiazolyl 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
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
• 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 6
• 125000000714 pyrimidinyl 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
• VRCDLRHESPRPEF-UQBPGWFLSA-N 2-[4-[(2s,4r)-2-methyl-4-(n-propanoylanilino)-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]acetic acid Chemical compound N1([C@@H](C)C[C@H](C2=CC=CC=C21)N(C(=O)CC)C=1C=CC=CC=1)C(=O)C1=CC=C(OCC(O)=O)C=C1 VRCDLRHESPRPEF-UQBPGWFLSA-N 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
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• NNFUAAFFLNVPAB-PZGXJGMVSA-N n-[(2s,4r)-2-methyl-1-(4-piperidin-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=C1C1CCNCC1 NNFUAAFFLNVPAB-PZGXJGMVSA-N 0.000 claims description 5
• 150000003254 radicals Chemical class 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• MYXKEWUDEMSZSY-AVRWGWEMSA-N 2-[4-[(2s,4r)-4-(n-acetylanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]anilino]acetic acid Chemical compound CC(=O)N([C@@H]1C[C@@H](N(C2=CC=CC=C21)C(=O)C=1C=CC(NCC(O)=O)=CC=1)C)C1=CC=CC=C1 MYXKEWUDEMSZSY-AVRWGWEMSA-N 0.000 claims description 4
• HCVZRMGPJWUBKV-CCLHPLFOSA-N 4-[4-[(2s,4r)-4-(4-chloro-n-propanoylanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]butanoic acid Chemical compound N1([C@@H](C)C[C@H](C2=CC=CC=C21)N(C(=O)CC)C=1C=CC(Cl)=CC=1)C(=O)C1=CC=C(OCCCC(O)=O)C=C1 HCVZRMGPJWUBKV-CCLHPLFOSA-N 0.000 claims description 4
• 206010012438 Dermatitis atopic Diseases 0.000 claims description 4
• 239000002841 Lewis acid Substances 0.000 claims description 4
• SYRGFNHNOBVGDO-AFMDSPMNSA-N N1C(=CC2=CC=CC=C12)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C(CC)=O)C1=CC=CC=C1)C Chemical compound N1C(=CC2=CC=CC=C12)C(=O)N1[C@H](C[C@H](C2=CC=CC=C12)N(C(CC)=O)C1=CC=CC=C1)C SYRGFNHNOBVGDO-AFMDSPMNSA-N 0.000 claims description 4
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
• 230000003213 activating effect Effects 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
• 125000002619 bicyclic group Chemical group 0.000 claims description 4
• 150000003857 carboxamides Chemical class 0.000 claims description 4
• 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 4
• 150000007517 lewis acids Chemical class 0.000 claims description 4
• FRDILXJBSBHTDY-WTYVLRPYSA-N methyl 3-[4-[(2s,4r)-4-(n-acetyl-4-chloroanilino)-2-methyl-3,4-dihydro-2h-quinoline-1-carbonyl]phenoxy]-2,2-dimethylpropanoate Chemical compound C1=CC(OCC(C)(C)C(=O)OC)=CC=C1C(=O)N1C2=CC=CC=C2[C@H](N(C(C)=O)C=2C=CC(Cl)=CC=2)C[C@@H]1C FRDILXJBSBHTDY-WTYVLRPYSA-N 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
• 125000006239 protecting group Chemical group 0.000 claims description 4
• 239000012279 sodium borohydride Substances 0.000 claims description 4
• 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
• 208000024891 symptom Diseases 0.000 claims description 4
• RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims description 4
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 4
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 3
• QDVGFLOWCALOLI-QXNWPYRLSA-N C1CN(CC)CCC1C1=CC=C(C(=O)N2C3=CC=CC=C3[C@H](N(C(=O)CC)C=3C=CC=CC=3)C[C@@H]2C)C=C1 Chemical compound C1CN(CC)CCC1C1=CC=C(C(=O)N2C3=CC=CC=C3[C@H](N(C(=O)CC)C=3C=CC=CC=3)C[C@@H]2C)C=C1 QDVGFLOWCALOLI-QXNWPYRLSA-N 0.000 claims description 3
• AFMDHQZMYZPSBX-KDYSTLNUSA-N CN(C(=O)COC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1)C Chemical compound CN(C(=O)COC1=CC=C(C(=O)N2[C@H](C[C@H](C3=CC=CC=C23)N(C(CC)=O)C2=CC=CC=C2)C)C=C1)C AFMDHQZMYZPSBX-KDYSTLNUSA-N 0.000 claims description 3
• KSLZYDRSRXVRSH-YADARESESA-N S1C2=C(C=C1C(=O)N1[C@H](C[C@H](C3=CC=CC=C13)N(C(CC)=O)C1=CC=CC=C1)C)C=CC=C2 Chemical compound S1C2=C(C=C1C(=O)N1[C@H](C[C@H](C3=CC=CC=C13)N(C(CC)=O)C1=CC=CC=C1)C)C=CC=C2 KSLZYDRSRXVRSH-YADARESESA-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
• 125000006244 carboxylic acid protecting group Chemical group 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
• CQZDRCXDMUWISU-WTYVLRPYSA-N n-(4-chlorophenyl)-n-[(2s,4r)-1-[4-(3-hydroxy-2,2-dimethylpropoxy)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(OCC(C)(C)CO)=CC=1)C)C1=CC=C(Cl)C=C1 CQZDRCXDMUWISU-WTYVLRPYSA-N 0.000 claims description 3
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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
• 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
• 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 description 2
• ZFZKQSJDRMYDRC-AFJIDDCJSA-N C[C@@H](C1)N(C(C(C=C2)=CC=C2C(CC2)=CCN2C(O)=O)=O)C2=CC=CC=C2[C@@H]1N(C(C)=O)C(C=C1)=CC=C1Cl Chemical compound C[C@@H](C1)N(C(C(C=C2)=CC=C2C(CC2)=CCN2C(O)=O)=O)C2=CC=CC=C2[C@@H]1N(C(C)=O)C(C=C1)=CC=C1Cl ZFZKQSJDRMYDRC-AFJIDDCJSA-N 0.000 claims description 2
• 125000002393 azetidinyl group Chemical group 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
• 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 2
• ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-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
• CLGFTNLBVNHWJV-AFJIDDCJSA-N n-(4-chlorophenyl)-n-[(2s,4r)-1-(4-cyclopentyloxybenzoyl)-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(OC2CCCC2)=CC=1)C)C1=CC=C(Cl)C=C1 CLGFTNLBVNHWJV-AFJIDDCJSA-N 0.000 claims description 2
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