CA2648813A1

CA2648813A1 - Organic compounds

Organic compounds Download PDF

Info

Publication number: CA2648813A1
Authority: CA; Canada
Prior art keywords: optionally substituted; amino; alkyl; purin; membered heterocyclic
Prior art date: 2006-04-21
Legal status : Abandoned

Application number

CA002648813A

Other languages

English (en)

French (fr)

Inventor

Robin Alec Fairhurst

Roger John Taylor

Current Assignee

Novartis AG

Original Assignee

Individual

Priority date

2006-04-21

Filing date

2007-04-19

Publication date

2007-11-01

2007-04-19 Application filed by Individual filed Critical Individual

2007-11-01 Publication of CA2648813A1 publication Critical patent/CA2648813A1/en

Status Abandoned legal-status Critical Current

Links

150000002894 organic compounds Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 357
150000003839 salts Chemical class 0.000 claims abstract description 31
239000003814 drug Substances 0.000 claims abstract description 13
-1 substituted Chemical class 0.000 claims description 71
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 62
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 61
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 59
229910052757 nitrogen Inorganic materials 0.000 claims description 50
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 47
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 46
229910052760 oxygen Inorganic materials 0.000 claims description 46
239000001301 oxygen Chemical group 0.000 claims description 46
125000005842 heteroatom Chemical group 0.000 claims description 45
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 44
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 43
239000005864 Sulphur Chemical group 0.000 claims description 43
125000005843 halogen group Chemical group 0.000 claims description 39
239000003795 chemical substances by application Substances 0.000 claims description 34
229910052739 hydrogen Inorganic materials 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 30
230000002757 inflammatory effect Effects 0.000 claims description 18
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 13
208000027866 inflammatory disease Diseases 0.000 claims description 10
230000004913 activation Effects 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
125000004043 oxo group Chemical group O=* 0.000 claims description 8
230000000694 effects Effects 0.000 claims description 7
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
230000029663 wound healing Effects 0.000 claims description 6
206010061218 Inflammation Diseases 0.000 claims description 5
206010063837 Reperfusion injury Diseases 0.000 claims description 5
230000004054 inflammatory process Effects 0.000 claims description 5
208000011580 syndromic disease Diseases 0.000 claims description 5
102000007471 Adenosine A2A receptor Human genes 0.000 claims description 4
108010085277 Adenosine A2A receptor Proteins 0.000 claims description 4
208000028867 ischemia Diseases 0.000 claims description 4
230000001404 mediated effect Effects 0.000 claims description 4
230000009467 reduction Effects 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
201000000057 Coronary Stenosis Diseases 0.000 claims description 3
206010011089 Coronary artery stenosis Diseases 0.000 claims description 3
201000003883 Cystic fibrosis Diseases 0.000 claims description 3
208000007342 Diabetic Nephropathies Diseases 0.000 claims description 3
229940123038 Integrin antagonist Drugs 0.000 claims description 3
229940124158 Protease/peptidase inhibitor Drugs 0.000 claims description 3
238000011360 adjunctive therapy Methods 0.000 claims description 3
238000002399 angioplasty Methods 0.000 claims description 3
210000000424 bronchial epithelial cell Anatomy 0.000 claims description 3
208000033679 diabetic kidney disease Diseases 0.000 claims description 3
230000002526 effect on cardiovascular system Effects 0.000 claims description 3
239000012216 imaging agent Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
210000000056 organ Anatomy 0.000 claims description 3
244000052769 pathogen Species 0.000 claims description 3
239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 3
230000001737 promoting effect Effects 0.000 claims description 3
208000005069 pulmonary fibrosis Diseases 0.000 claims description 3
208000002815 pulmonary hypertension Diseases 0.000 claims description 3
230000002285 radioactive effect Effects 0.000 claims description 3
208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
208000016192 Demyelinating disease Diseases 0.000 claims description 2
201000009267 bronchiectasis Diseases 0.000 claims description 2
238000003384 imaging method Methods 0.000 claims description 2
239000004090 neuroprotective agent Substances 0.000 claims description 2
125000000041 C6-C10 aryl group Chemical group 0.000 claims 10
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 9
125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 2
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 25
235000013350 formula milk Nutrition 0.000 description 147
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 133
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 120
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 115
238000006243 chemical reaction Methods 0.000 description 111
238000000034 method Methods 0.000 description 99
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 84
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
229940080818 propionamide Drugs 0.000 description 78
239000011541 reaction mixture Substances 0.000 description 65
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 61
239000002904 solvent Substances 0.000 description 59
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 58
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 57
239000000203 mixture Substances 0.000 description 54
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 54
239000000243 solution Substances 0.000 description 54
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 49
229910052786 argon Inorganic materials 0.000 description 42
238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 42
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 40
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
239000000543 intermediate Substances 0.000 description 36
239000003960 organic solvent Substances 0.000 description 35
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 34
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 32
239000012298 atmosphere Substances 0.000 description 30
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
239000002585 base Substances 0.000 description 28
238000000746 purification Methods 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 27
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
238000004440 column chromatography Methods 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
230000002441 reversible effect Effects 0.000 description 21
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 20
208000006673 asthma Diseases 0.000 description 19
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 19
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 18
235000009518 sodium iodide Nutrition 0.000 description 18
150000001412 amines Chemical class 0.000 description 17
OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
239000003054 catalyst Substances 0.000 description 15
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 15
229910052799 carbon Inorganic materials 0.000 description 14
230000008569 process Effects 0.000 description 14
239000000047 product Substances 0.000 description 14
239000000377 silicon dioxide Substances 0.000 description 13
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
229940093499 ethyl acetate Drugs 0.000 description 12
235000019439 ethyl acetate Nutrition 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 11
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 11
238000003818 flash chromatography Methods 0.000 description 11
239000012948 isocyanate Substances 0.000 description 11
150000002513 isocyanates Chemical class 0.000 description 11
229910052943 magnesium sulfate Inorganic materials 0.000 description 11
235000019341 magnesium sulphate Nutrition 0.000 description 11
230000002829 reductive effect Effects 0.000 description 11
CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 10
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
239000012267 brine Substances 0.000 description 10
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 10
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
125000001309 chloro group Chemical group Cl* 0.000 description 9
TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
MASVPNZBPHOQNL-TYJFDUFHSA-N n-[(1s,2r,3s,4r)-4-[2-chloro-6-(2,2-diphenylethylamino)purin-9-yl]-2,3-dihydroxycyclopentyl]propanamide Chemical compound O[C@@H]1[C@H](O)[C@@H](NC(=O)CC)C[C@H]1N1C2=NC(Cl)=NC(NCC(C=3C=CC=CC=3)C=3C=CC=CC=3)=C2N=C1 MASVPNZBPHOQNL-TYJFDUFHSA-N 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 8
208000027771 Obstructive airways disease Diseases 0.000 description 8
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
201000010099 disease Diseases 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
229940047889 isobutyramide Drugs 0.000 description 8
229910000489 osmium tetroxide Inorganic materials 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
239000005557 antagonist Substances 0.000 description 7
125000004432 carbon atom Chemical group C* 0.000 description 7
125000000623 heterocyclic group Chemical group 0.000 description 7
150000002431 hydrogen Chemical class 0.000 description 7
YMYJWRNXFNUREO-TXDVJWISSA-N n-[(1s,2r,3s,4r)-4-[6-(2,2-diphenylethylamino)-2-[[(2s)-1-hydroxy-3-phenylpropan-2-yl]amino]purin-9-yl]-2,3-dihydroxycyclopentyl]propanamide Chemical compound O[C@@H]1[C@H](O)[C@@H](NC(=O)CC)C[C@H]1N1C2=NC(N[C@H](CO)CC=3C=CC=CC=3)=NC(NCC(C=3C=CC=CC=3)C=3C=CC=CC=3)=C2N=C1 YMYJWRNXFNUREO-TXDVJWISSA-N 0.000 description 7
239000012285 osmium tetroxide Substances 0.000 description 7
125000003386 piperidinyl group Chemical group 0.000 description 7
125000004076 pyridyl group Chemical group 0.000 description 7
NRWPBTLQVZIEGO-UHFFFAOYSA-N 2-(1-propan-2-ylimidazol-4-yl)ethanamine Chemical compound CC(C)N1C=NC(CCN)=C1 NRWPBTLQVZIEGO-UHFFFAOYSA-N 0.000 description 6
239000002126 C01EB10 - Adenosine Substances 0.000 description 6
101150041968 CDC13 gene Proteins 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
229960005305 adenosine Drugs 0.000 description 6
230000003110 anti-inflammatory effect Effects 0.000 description 6
230000003182 bronchodilatating effect Effects 0.000 description 6
239000004202 carbamide Substances 0.000 description 6
150000001721 carbon Chemical group 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
238000009472 formulation Methods 0.000 description 6
230000005445 isotope effect Effects 0.000 description 6
OOXMNSGDGNQMNC-AICRDVKUSA-N n-[(1s,2r,3s,4r)-4-[2-chloro-6-(2,2-diphenylethylamino)purin-9-yl]-2,3-dihydroxycyclopentyl]cyclobutanecarboxamide Chemical compound N1=C(Cl)N=C2N([C@@H]3C[C@@H]([C@H]([C@H]3O)O)NC(=O)C3CCC3)C=NC2=C1NCC(C=1C=CC=CC=1)C1=CC=CC=C1 OOXMNSGDGNQMNC-AICRDVKUSA-N 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
NGXSWUFDCSEIOO-SCSAIBSYSA-N (3r)-pyrrolidin-3-amine Chemical compound N[C@@H]1CCNC1 NGXSWUFDCSEIOO-SCSAIBSYSA-N 0.000 description 5
DKCWQRKXTQSULZ-UHFFFAOYSA-N 1h-imidazole;urea Chemical compound NC(N)=O.C1=CNC=N1 DKCWQRKXTQSULZ-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
235000013877 carbamide Nutrition 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
229940043279 diisopropylamine Drugs 0.000 description 5
210000003979 eosinophil Anatomy 0.000 description 5
125000004494 ethyl ester group Chemical group 0.000 description 5
125000002883 imidazolyl group Chemical group 0.000 description 5
229960004592 isopropanol Drugs 0.000 description 5
BNGCBNFCYFRFLY-FSNRGTNLSA-N n-[(1s,2r,3s,4r)-4-[2-[(3r)-3-aminopyrrolidin-1-yl]-6-(2,2-diphenylethylamino)purin-9-yl]-2,3-dihydroxycyclopentyl]propanamide Chemical compound O[C@@H]1[C@H](O)[C@@H](NC(=O)CC)C[C@H]1N1C2=NC(N3C[C@H](N)CC3)=NC(NCC(C=3C=CC=CC=3)C=3C=CC=CC=3)=C2N=C1 BNGCBNFCYFRFLY-FSNRGTNLSA-N 0.000 description 5
MIVFLRKONVQVSU-DRABBMOASA-N n-[(1s,2r,3s,4r)-4-[2-chloro-6-(pentan-3-ylamino)purin-9-yl]-2,3-dihydroxycyclopentyl]propanamide Chemical compound C1=NC=2C(NC(CC)CC)=NC(Cl)=NC=2N1[C@@H]1C[C@H](NC(=O)CC)[C@@H](O)[C@H]1O MIVFLRKONVQVSU-DRABBMOASA-N 0.000 description 5
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 5
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
230000005855 radiation Effects 0.000 description 5
102000005962 receptors Human genes 0.000 description 5
108020003175 receptors Proteins 0.000 description 5
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
206010027654 Allergic conditions Diseases 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
229940124623 antihistamine drug Drugs 0.000 description 4
239000000739 antihistaminic agent Substances 0.000 description 4
230000001363 autoimmune Effects 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
230000001684 chronic effect Effects 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
229940079593 drug Drugs 0.000 description 4
229940088679 drug related substance Drugs 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
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