MXPA06011540A - Antagonistas del receptor de pgd2 para el tratamiento de enfermedades inflamatorias. - Google Patents

Info

Publication number

MXPA06011540A

MXPA06011540A MXPA06011540A MXPA06011540A MXPA06011540A MX PA06011540 A MXPA06011540 A MX PA06011540A MX PA06011540 A MXPA06011540 A MX PA06011540A MX PA06011540 A MXPA06011540 A MX PA06011540A MX PA06011540 A MXPA06011540 A MX PA06011540A

Authority

MX

Mexico

Prior art keywords

methyl

substituted

phenyl

haloalkyl

group

Prior art date

2004-04-07

Links

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• 208000027866 inflammatory disease Diseases 0.000 title claims abstract description 18
• 108050000258 Prostaglandin D receptors Proteins 0.000 title abstract description 44
• 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 229
• -1 haioalkyl Chemical group 0.000 claims description 788
• 229910052739 hydrogen Inorganic materials 0.000 claims description 308
• 238000000034 method Methods 0.000 claims description 208
• 125000001188 haloalkyl group Chemical group 0.000 claims description 164
• 125000000217 alkyl group Chemical group 0.000 claims description 154
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 118
• 125000003118 aryl group Chemical group 0.000 claims description 111
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 106
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 86
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 84
• 125000001072 heteroaryl group Chemical group 0.000 claims description 77
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 76
• 239000002253 acid Substances 0.000 claims description 69
• 229910052757 nitrogen Inorganic materials 0.000 claims description 67
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 65
• 229910052799 carbon Inorganic materials 0.000 claims description 62
• 125000001424 substituent group Chemical group 0.000 claims description 55
• 150000001721 carbon Chemical group 0.000 claims description 52
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 51
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 50
• 229910052736 halogen Inorganic materials 0.000 claims description 46
• 150000002367 halogens Chemical class 0.000 claims description 46
• 150000004820 halides Chemical class 0.000 claims description 45
• 125000002757 morpholinyl group Chemical group 0.000 claims description 39
• 239000001257 hydrogen Substances 0.000 claims description 38
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 38
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 38
• 125000002947 alkylene group Chemical group 0.000 claims description 36
• 150000001412 amines Chemical group 0.000 claims description 34
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 32
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
• 125000003386 piperidinyl group Chemical group 0.000 claims description 31
• 125000004193 piperazinyl group Chemical group 0.000 claims description 29
• 125000004432 carbon atom Chemical group C* 0.000 claims description 28
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
• 125000002950 monocyclic group Chemical group 0.000 claims description 27
• 150000003839 salts Chemical class 0.000 claims description 27
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 26
• 125000002883 imidazolyl group Chemical group 0.000 claims description 26
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
• 125000003545 alkoxy group Chemical group 0.000 claims description 25
• 150000002431 hydrogen Chemical group 0.000 claims description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims description 24
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 24
• 125000004494 ethyl ester group Chemical group 0.000 claims description 22
• 125000001984 thiazolidinyl group Chemical group 0.000 claims description 22
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 21
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 21
• 229910052717 sulfur Inorganic materials 0.000 claims description 21
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 21
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 20
• 229940080818 propionamide Drugs 0.000 claims description 18
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 17
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 17
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 17
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 17
• 150000003973 alkyl amines Chemical group 0.000 claims description 16
• 125000002541 furyl group Chemical group 0.000 claims description 16
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 16
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• 125000005265 dialkylamine group Chemical group 0.000 claims description 15
• 125000000160 oxazolidinyl group Chemical group 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 125000002837 carbocyclic group Chemical group 0.000 claims description 14
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 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
• 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
• 125000005843 halogen group Chemical group 0.000 claims description 13
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 13
• 125000004076 pyridyl group Chemical group 0.000 claims description 13
• 125000001544 thienyl group Chemical group 0.000 claims description 13
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 13
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 12
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 12
• 150000001408 amides Chemical group 0.000 claims description 12
• 125000005879 dioxolanyl group Chemical group 0.000 claims description 12
• 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 12
• 230000002829 reductive effect Effects 0.000 claims description 12
• 125000003003 spiro group Chemical group 0.000 claims description 12
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 12
• 150000004702 methyl esters Chemical class 0.000 claims description 11
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 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
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
• 125000002971 oxazolyl group Chemical group 0.000 claims description 10
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 9
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 8
• KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 8
• RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical class [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
• 239000007858 starting material Substances 0.000 claims description 8
• 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 8
• 208000006673 asthma Diseases 0.000 claims description 7
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
• 125000000335 thiazolyl group Chemical group 0.000 claims description 7
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
• FDKJHRJHQDBERC-UHFFFAOYSA-N CCC(N(C(CC1C)C2=CC=CC=C2N1C(C1=CC=C(C(CCCC2)N2C(O)=O)C=C1)=O)C1=CC=CC=C1)=O Chemical compound CCC(N(C(CC1C)C2=CC=CC=C2N1C(C1=CC=C(C(CCCC2)N2C(O)=O)C=C1)=O)C1=CC=CC=C1)=O FDKJHRJHQDBERC-UHFFFAOYSA-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
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 239000011737 fluorine Substances 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 208000024891 symptom Diseases 0.000 claims description 5
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• 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
• 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
• 230000009435 amidation Effects 0.000 claims description 4
• 238000007112 amidation reaction Methods 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
• 150000001805 chlorine compounds Chemical group 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 150000007517 lewis acids Chemical class 0.000 claims description 4
• 239000012279 sodium borohydride Substances 0.000 claims description 4
• 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
• RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims description 4
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• 125000006241 alcohol protecting group Chemical group 0.000 claims description 3
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical group C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 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
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
• 235000019260 propionic acid Nutrition 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
• BLMLUNANEFKSJK-UHFFFAOYSA-N 2-[1-[4-(2-hydroxy-2-methylpropoxy)benzoyl]-2-methyl-3,4-dihydro-2H-quinolin-4-yl]-N-phenylpropanamide Chemical compound OC(COC1=CC=C(C(=O)N2C(CC(C3=CC=CC=C23)C(C(=O)NC2=CC=CC=C2)C)C)C=C1)(C)C BLMLUNANEFKSJK-UHFFFAOYSA-N 0.000 claims description 2
• BDBZVFLJUKFYFI-UHFFFAOYSA-N 2-[2-methyl-1-[4-(2H-tetrazol-5-ylmethoxy)benzoyl]-3,4-dihydro-2H-quinolin-4-yl]acetamide Chemical compound CC1N(C2=CC=CC=C2C(C1)CC(=O)N)C(C1=CC=C(C=C1)OCC1=NN=NN1)=O BDBZVFLJUKFYFI-UHFFFAOYSA-N 0.000 claims description 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 2
• IQQSVZYRBJIDFJ-UHFFFAOYSA-N CC1N(C(C(C=C2)=CC=C2OCCN2CCOCC2)=O)C2=CC=CC=C2C(CC(N)=O)C1 Chemical compound CC1N(C(C(C=C2)=CC=C2OCCN2CCOCC2)=O)C2=CC=CC=C2C(CC(N)=O)C1 IQQSVZYRBJIDFJ-UHFFFAOYSA-N 0.000 claims description 2
• 230000002862 amidating effect Effects 0.000 claims description 2
• 150000007942 carboxylates Chemical class 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
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 2
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
• 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
• 239000007825 activation reagent Substances 0.000 claims 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
• 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims 1
• OTHZWPCEPMAICA-UHFFFAOYSA-N 2-[1-[4-(4-acetylpiperazin-1-yl)benzoyl]-2-methyl-3,4-dihydro-2H-quinolin-4-yl]-N-(4-chlorophenyl)acetamide Chemical compound C(C)(=O)N1CCN(CC1)C1=CC=C(C(=O)N2C(CC(C3=CC=CC=C23)CC(=O)NC2=CC=C(C=C2)Cl)C)C=C1 OTHZWPCEPMAICA-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• FVRKCGXUPLTUAI-UHFFFAOYSA-N CC1N(C(C(C=C2)=CC=C2OCC2=CC=NC=C2)=O)C2=CC=CC=C2C(CC(N)=O)C1 Chemical compound CC1N(C(C(C=C2)=CC=C2OCC2=CC=NC=C2)=O)C2=CC=CC=C2C(CC(N)=O)C1 FVRKCGXUPLTUAI-UHFFFAOYSA-N 0.000 claims 1
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
• 241000790917 Dioxys <bee> Species 0.000 claims 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
• 125000005505 thiomorpholino group Chemical group 0.000 claims 1
• 230000002401 inhibitory effect Effects 0.000 abstract description 2
• 102000003688 G-Protein-Coupled Receptors Human genes 0.000 abstract 1
• 108090000045 G-Protein-Coupled Receptors Proteins 0.000 abstract 1
• 102100024218 Prostaglandin D2 receptor 2 Human genes 0.000 abstract 1
• 239000002975 chemoattractant Substances 0.000 abstract 1
• 238000005481 NMR spectroscopy Methods 0.000 description 172
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 154
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 128
• OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 109
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 101
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 86
• 239000012346 acetyl chloride Substances 0.000 description 86
• 239000000203 mixture Substances 0.000 description 86
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 84
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 59
• RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 56
• 238000006243 chemical reaction Methods 0.000 description 53
• 235000019439 ethyl acetate Nutrition 0.000 description 52
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
• 239000000243 solution Substances 0.000 description 41
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 34
• 235000019441 ethanol Nutrition 0.000 description 31
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
• 229910001868 water Inorganic materials 0.000 description 28
• 239000000741 silica gel Substances 0.000 description 26
• 229910002027 silica gel Inorganic materials 0.000 description 26
• 238000003756 stirring Methods 0.000 description 26
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