ES2514471T3 - Compuestos de pirimidin-amida como inhibidores de PGDS - Google Patents

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Publication number

ES2514471T3

ES2514471T3 ES06816247.8T ES06816247T ES2514471T3 ES 2514471 T3 ES2514471 T3 ES 2514471T3 ES 06816247 T ES06816247 T ES 06816247T ES 2514471 T3 ES2514471 T3 ES 2514471T3

Authority

ES

Spain

Prior art keywords

phenyl

pyrimidine

carboxylic acid

fluoro

benzylamide

Prior art date

2005-10-04

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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• 102100029100 Hematopoietic prostaglandin D synthase Human genes 0.000 title description 32
• 101710145576 Prostaglandin-H2 D-isomerase Proteins 0.000 title description 12
• 239000003112 inhibitor Substances 0.000 title description 8
• FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical class NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 title description 3
• -1 oxodiazolyl Chemical group 0.000 claims abstract description 306
• 150000001875 compounds Chemical class 0.000 claims abstract description 106
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 78
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 73
• 125000003118 aryl group Chemical group 0.000 claims abstract description 59
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 58
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 56
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 55
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 55
• 150000002367 halogens Chemical group 0.000 claims abstract description 53
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 36
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 34
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 33
• 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 24
• 239000001257 hydrogen Substances 0.000 claims abstract description 24
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
• 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 19
• 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 19
• 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 19
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 19
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 16
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 12
• 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 11
• 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 11
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
• 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 10
• 125000002632 imidazolidinyl group Chemical group 0.000 claims abstract description 10
• 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 10
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract description 10
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 8
• 125000002252 acyl group Chemical group 0.000 claims abstract description 8
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 8
• 125000003435 aroyl group Chemical group 0.000 claims abstract description 7
• 125000004104 aryloxy group Chemical group 0.000 claims abstract description 7
• 125000005553 heteroaryloxy group Chemical group 0.000 claims abstract description 7
• 125000001544 thienyl group Chemical group 0.000 claims abstract description 7
• 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims abstract description 6
• 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims abstract description 6
• 125000002541 furyl group Chemical group 0.000 claims abstract description 6
• 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 6
• 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 6
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 5
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
• 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 5
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract description 3
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 3
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 3
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract description 3
• 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims abstract description 3
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims abstract description 3
• 229910052757 nitrogen Inorganic materials 0.000 claims description 81
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 75
• DYPNEVXAPRDVCM-UHFFFAOYSA-N 2-(3-fluorophenyl)pyrimidine-5-carboxylic acid Chemical compound N1=CC(C(=O)O)=CN=C1C1=CC=CC(F)=C1 DYPNEVXAPRDVCM-UHFFFAOYSA-N 0.000 claims description 64
• 150000001204 N-oxides Chemical class 0.000 claims description 56
• 150000003839 salts Chemical class 0.000 claims description 56
• BOAIYSRFGWBZCF-UHFFFAOYSA-N 2-phenylpyrimidine-5-carboxylic acid Chemical compound N1=CC(C(=O)O)=CN=C1C1=CC=CC=C1 BOAIYSRFGWBZCF-UHFFFAOYSA-N 0.000 claims description 52
• 239000002253 acid Substances 0.000 claims description 51
• 239000012453 solvate Substances 0.000 claims description 45
• 229910052717 sulfur Chemical group 0.000 claims description 43
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 40
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 34
• 229910052760 oxygen Inorganic materials 0.000 claims description 22
• 239000001301 oxygen Substances 0.000 claims description 22
• LZMNSJCIRQSESL-UHFFFAOYSA-N 2-(3-fluorophenyl)-4-methylpyrimidine-5-carboxylic acid Chemical compound C1=C(C(O)=O)C(C)=NC(C=2C=C(F)C=CC=2)=N1 LZMNSJCIRQSESL-UHFFFAOYSA-N 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 10
• 201000010105 allergic rhinitis Diseases 0.000 claims description 10
• 208000006673 asthma Diseases 0.000 claims description 10
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• FMVLDCBNRZZNPH-UHFFFAOYSA-N 3-(aminomethyl)-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(CN)=C1 FMVLDCBNRZZNPH-UHFFFAOYSA-N 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 208000010668 atopic eczema Diseases 0.000 claims description 7
• HBERNPIFDLWOKM-UHFFFAOYSA-N 1-(3-fluorophenyl)-2H-pyrimidine-5-carboxylic acid Chemical compound FC=1C=C(C=CC=1)N1CN=CC(=C1)C(=O)O HBERNPIFDLWOKM-UHFFFAOYSA-N 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 201000009961 allergic asthma Diseases 0.000 claims description 6
• 230000000172 allergic effect Effects 0.000 claims description 6
• 150000001408 amides Chemical class 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 208000027866 inflammatory disease Diseases 0.000 claims description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• 239000011593 sulfur Chemical group 0.000 claims description 6
• BDZAKJITXGLLPO-UHFFFAOYSA-N 4-methyl-2-[(2-phenylpyrimidine-5-carbonyl)amino]-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(O)=O)=C(C)N=C1NC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1 BDZAKJITXGLLPO-UHFFFAOYSA-N 0.000 claims description 5
• 125000002947 alkylene group Chemical group 0.000 claims description 5
• AFIQCJGNOINCFJ-UHFFFAOYSA-N 2-(2-fluorophenyl)-n-phenylpyrimidine-5-carboxamide Chemical compound FC1=CC=CC=C1C1=NC=C(C(=O)NC=2C=CC=CC=2)C=N1 AFIQCJGNOINCFJ-UHFFFAOYSA-N 0.000 claims description 4
• LNRLXJGRGPYMFQ-UHFFFAOYSA-N 2-phenyl-n-[1-(pyridin-3-ylmethyl)piperidin-4-yl]pyrimidine-5-carboxamide Chemical compound C=1N=C(C=2C=CC=CC=2)N=CC=1C(=O)NC(CC1)CCN1CC1=CC=CN=C1 LNRLXJGRGPYMFQ-UHFFFAOYSA-N 0.000 claims description 4
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
• 150000002148 esters Chemical class 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 claims description 3
• DGWRARJZGOMGGO-UHFFFAOYSA-N 2-(3,5-difluorophenyl)pyrimidine-5-carboxylic acid Chemical compound N1=CC(C(=O)O)=CN=C1C1=CC(F)=CC(F)=C1 DGWRARJZGOMGGO-UHFFFAOYSA-N 0.000 claims description 3
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
• JSFAAXVTHOLLEY-UHFFFAOYSA-N 2-phenyl-n-[(4-sulfamoylphenyl)methyl]pyrimidine-5-carboxamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC(=O)C1=CN=C(C=2C=CC=CC=2)N=C1 JSFAAXVTHOLLEY-UHFFFAOYSA-N 0.000 claims description 3
• GSCPDZHWVNUUFI-UHFFFAOYSA-N 3-aminobenzamide Chemical compound NC(=O)C1=CC=CC(N)=C1 GSCPDZHWVNUUFI-UHFFFAOYSA-N 0.000 claims description 3
• OYAHSBDYBOBAAQ-UHFFFAOYSA-N 3-phenyl-1,2,4-thiadiazol-5-amine Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=N1 OYAHSBDYBOBAAQ-UHFFFAOYSA-N 0.000 claims description 3
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
• 239000003814 drug Substances 0.000 claims description 3
• POAYTBQJGDPYTN-UHFFFAOYSA-N ethyl 4-methyl-2-[(2-phenylpyrimidine-5-carbonyl)amino]-1,3-thiazole-5-carboxylate Chemical compound CC1=C(C(=O)OCC)SC(NC(=O)C=2C=NC(=NC=2)C=2C=CC=CC=2)=N1 POAYTBQJGDPYTN-UHFFFAOYSA-N 0.000 claims description 3
• IPBPLHNLRKRLPJ-UHFFFAOYSA-N oxan-4-ylmethanamine Chemical compound NCC1CCOCC1 IPBPLHNLRKRLPJ-UHFFFAOYSA-N 0.000 claims description 3
• RFJHMCHPQLPJGP-UHFFFAOYSA-N 2-[2-(2-amino-1,3-thiazol-4-yl)ethyl]isoindole-1,3-dione Chemical compound S1C(N)=NC(CCN2C(C3=CC=CC=C3C2=O)=O)=C1 RFJHMCHPQLPJGP-UHFFFAOYSA-N 0.000 claims description 2
• BVYAHOVQMVDNOK-UHFFFAOYSA-N 3-(aminomethyl)-N-[5-(dimethylamino)pentyl]benzenesulfonamide Chemical compound CN(C)CCCCCNS(=O)(=O)C1=CC=CC(=C1)CN BVYAHOVQMVDNOK-UHFFFAOYSA-N 0.000 claims description 2
• CPHOJIBLTOHWSX-UHFFFAOYSA-N 3-(aminomethyl)-n-cyclopropylbenzenesulfonamide Chemical compound NCC1=CC=CC(S(=O)(=O)NC2CC2)=C1 CPHOJIBLTOHWSX-UHFFFAOYSA-N 0.000 claims description 2
• CDYQTLSHJJSYEO-UHFFFAOYSA-N 3-amino-2-phenylbenzenesulfonamide Chemical compound NC1=CC=CC(S(N)(=O)=O)=C1C1=CC=CC=C1 CDYQTLSHJJSYEO-UHFFFAOYSA-N 0.000 claims description 2
• PBGDGOWGZQNAHJ-UHFFFAOYSA-N 4-(aminomethyl)piperidine-1-carboximidamide Chemical compound NCC1CCN(C(N)=N)CC1 PBGDGOWGZQNAHJ-UHFFFAOYSA-N 0.000 claims description 2
• IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 claims description 2
• ZEOLVKFNZWLHOF-UHFFFAOYSA-N 5-(aminomethyl)-N-methylpyridine-3-sulfonamide Chemical compound CNS(=O)(=O)C1=CN=CC(CN)=C1 ZEOLVKFNZWLHOF-UHFFFAOYSA-N 0.000 claims description 2
• IQHJEXHUYLAQEI-UHFFFAOYSA-N 5-(aminomethyl)-N-propan-2-ylpyridine-3-sulfonamide Chemical compound CC(C)NS(=O)(=O)C1=CN=CC(CN)=C1 IQHJEXHUYLAQEI-UHFFFAOYSA-N 0.000 claims description 2
• YJIDKQVYACIBPR-UHFFFAOYSA-N 5-(aminomethyl)-n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=C(CN)C=N1 YJIDKQVYACIBPR-UHFFFAOYSA-N 0.000 claims description 2
• MPJDOPQJSUAXCW-UHFFFAOYSA-N C1(=CC=CC=C1)C1=NC=C(C=N1)C(=O)NC=1C=C2C(=CNC2=CC=1)C(=O)O Chemical compound C1(=CC=CC=C1)C1=NC=C(C=N1)C(=O)NC=1C=C2C(=CNC2=CC=1)C(=O)O MPJDOPQJSUAXCW-UHFFFAOYSA-N 0.000 claims description 2
• ZDILNFSMQGXSOH-UHFFFAOYSA-N C1=CC(=CC(=C1)F)C2(NC=C(C=N2)C(=O)O)C3=CC(=CC=C3)F Chemical compound C1=CC(=CC(=C1)F)C2(NC=C(C=N2)C(=O)O)C3=CC(=CC=C3)F ZDILNFSMQGXSOH-UHFFFAOYSA-N 0.000 claims description 2
• NZPWXEOETDVLQD-UHFFFAOYSA-N C1N=CC(=CN1C2=CC=CC=C2F)C(=O)O Chemical compound C1N=CC(=CN1C2=CC=CC=C2F)C(=O)O NZPWXEOETDVLQD-UHFFFAOYSA-N 0.000 claims description 2
• LGFWWMDPVOPXBB-UHFFFAOYSA-N N-[[3-(aminomethyl)phenyl]methyl]propane-2-sulfonamide Chemical compound CC(C)S(=O)(=O)NCC1=CC=CC(CN)=C1 LGFWWMDPVOPXBB-UHFFFAOYSA-N 0.000 claims description 2
• AHVQYHFYQWKUKB-UHFFFAOYSA-N oxan-4-amine Chemical compound NC1CCOCC1 AHVQYHFYQWKUKB-UHFFFAOYSA-N 0.000 claims description 2
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 2
• IIVUJUOJERNGQX-UHFFFAOYSA-N pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=CN=C1 IIVUJUOJERNGQX-UHFFFAOYSA-N 0.000 claims description 2
• LBPIQDBVEKSDQZ-UHFFFAOYSA-N (1-methylsulfonylpiperidin-3-yl)methanamine Chemical compound CS(=O)(=O)N1CCCC(CN)C1 LBPIQDBVEKSDQZ-UHFFFAOYSA-N 0.000 claims 1
• XLDWJOJGHKMPOR-UHFFFAOYSA-N (4-morpholin-4-ylsulfonylphenyl)methanamine Chemical compound C1=CC(CN)=CC=C1S(=O)(=O)N1CCOCC1 XLDWJOJGHKMPOR-UHFFFAOYSA-N 0.000 claims 1
• RBIZQDIIVYJNRS-UHFFFAOYSA-N 1,3-benzothiazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2SC=NC2=C1 RBIZQDIIVYJNRS-UHFFFAOYSA-N 0.000 claims 1
• FSBIAEYLUOBHLG-UHFFFAOYSA-N 2-phenylpyrimidine-5-carboxamide Chemical compound N1=CC(C(=O)N)=CN=C1C1=CC=CC=C1 FSBIAEYLUOBHLG-UHFFFAOYSA-N 0.000 claims 1
• JRFULQLOOJLLNB-UHFFFAOYSA-N 2-pyrrolidin-1-ylsulfonylethanamine Chemical compound NCCS(=O)(=O)N1CCCC1 JRFULQLOOJLLNB-UHFFFAOYSA-N 0.000 claims 1
• RBVLCPTWSFUIDQ-UHFFFAOYSA-N 3-(aminomethyl)-N-[3-(2-methylpiperidin-1-yl)propyl]benzenesulfonamide Chemical compound CC1CCCCN1CCCNS(=O)(=O)C1=CC=CC(CN)=C1 RBVLCPTWSFUIDQ-UHFFFAOYSA-N 0.000 claims 1
• XSKLMWLTOSBDGW-UHFFFAOYSA-N 4-(aminomethyl)-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(CN)C=C1 XSKLMWLTOSBDGW-UHFFFAOYSA-N 0.000 claims 1
• VCZJVXLWQTXSPQ-UHFFFAOYSA-N 4-methyl-1,3-oxazol-2-amine Chemical compound CC1=COC(N)=N1 VCZJVXLWQTXSPQ-UHFFFAOYSA-N 0.000 claims 1
• TVJZAWYJTWZWAT-UHFFFAOYSA-N C1=CC=C(C=C1)C2=NSC(=N2)C3=NC(=NC=C3C(=O)O)C4=CC(=CC=C4)F Chemical compound C1=CC=C(C=C1)C2=NSC(=N2)C3=NC(=NC=C3C(=O)O)C4=CC(=CC=C4)F TVJZAWYJTWZWAT-UHFFFAOYSA-N 0.000 claims 1
• VKNYMDAMAVQARZ-UHFFFAOYSA-N CC1=NC(C2=CC(F)=CC=C2)=NC=C1C(O)=O.CNS(C1=NC=CC(CN)=C1)(=O)=O Chemical compound CC1=NC(C2=CC(F)=CC=C2)=NC=C1C(O)=O.CNS(C1=NC=CC(CN)=C1)(=O)=O VKNYMDAMAVQARZ-UHFFFAOYSA-N 0.000 claims 1
• PEHXALGTCBNCNK-UHFFFAOYSA-N CCN(CC)CCNS(C1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O Chemical compound CCN(CC)CCNS(C1=CC=CC(CN)=C1)(=O)=O.OC(C1=CN=C(C2=CC(F)=CC=C2)N=C1)=O PEHXALGTCBNCNK-UHFFFAOYSA-N 0.000 claims 1
• UZRNPFZMHRPGPI-UHFFFAOYSA-N NCCC(C=C1)=CC=C1S(N)(=O)=O.OC(C1=CN=C(C2=CC=CC=C2)N=C1)=O Chemical compound NCCC(C=C1)=CC=C1S(N)(=O)=O.OC(C1=CN=C(C2=CC=CC=C2)N=C1)=O UZRNPFZMHRPGPI-UHFFFAOYSA-N 0.000 claims 1
• GUBUOCQAHBYPIC-UHFFFAOYSA-N [4-(thiadiazol-5-yl)phenyl]methanamine Chemical compound C1=CC(CN)=CC=C1C1=CN=NS1 GUBUOCQAHBYPIC-UHFFFAOYSA-N 0.000 claims 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• CNMSPXXOHMCNDX-UHFFFAOYSA-N n-methylpyridine-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC=N1 CNMSPXXOHMCNDX-UHFFFAOYSA-N 0.000 claims 1
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims 1
• 238000000034 method Methods 0.000 description 122
• 238000001819 mass spectrum Methods 0.000 description 111
• 239000000203 mixture Substances 0.000 description 106
• 239000007787 solid Substances 0.000 description 95
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
• 238000005160 1H NMR spectroscopy Methods 0.000 description 79
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 70
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 65
• 239000000243 solution Substances 0.000 description 63
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 54
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 54
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 46
• 235000019439 ethyl acetate Nutrition 0.000 description 41
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
• 125000006413 ring segment Chemical group 0.000 description 32
• CFHZGJYPGQCCJN-UHFFFAOYSA-N 2,1-benzothiazol-5-amine Chemical compound C1=C(N)C=CC2=NSC=C21 CFHZGJYPGQCCJN-UHFFFAOYSA-N 0.000 description 31
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
• 150000001412 amines Chemical class 0.000 description 31
• 125000004434 sulfur atom Chemical group 0.000 description 30
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 28
• 125000004432 carbon atom Chemical group C* 0.000 description 28
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 26
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
• 125000004429 atom Chemical group 0.000 description 25
• BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 description 23
• RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 22
• 239000000843 powder Substances 0.000 description 21
• 101000988802 Homo sapiens Hematopoietic prostaglandin D synthase Proteins 0.000 description 20
• 238000006243 chemical reaction Methods 0.000 description 20
• BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 description 20
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 19
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
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