JP2005516046A5

JP2005516046A5 -

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Publication number: JP2005516046A5
Authority: JP; Japan
Prior art keywords: compound; fluoro; group; chloro; pyrimidinamine
Prior art date: 2003-01-31
Legal status : Granted

Application number

JP2003563490A

Other languages

English (en)

Japanese (ja)

Other versions

JP4658477B2 (ja

JP2005516046A (ja

Filing date

2003-01-31

Publication date

2010-09-30

2003-01-31 Application filed filed Critical

2003-01-31 Priority claimed from PCT/US2003/003022 external-priority patent/WO2003063794A2/en

2005-06-02 Publication of JP2005516046A publication Critical patent/JP2005516046A/ja

2010-09-30 Publication of JP2005516046A5 publication Critical patent/JP2005516046A5/ja

2011-03-23 Application granted granted Critical

2011-03-23 Publication of JP4658477B2 publication Critical patent/JP4658477B2/ja

2023-01-31 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

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-1 tri-substituted phenyl Chemical group 0.000 claims description 316
150000001875 compounds Chemical class 0.000 claims description 310
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 102
238000006243 chemical reaction Methods 0.000 claims description 84
229940002612 prodrug Drugs 0.000 claims description 84
239000000651 prodrug Substances 0.000 claims description 84
YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical class NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims description 83
230000019491 signal transduction Effects 0.000 claims description 82
229910052739 hydrogen Inorganic materials 0.000 claims description 77
239000001257 hydrogen Substances 0.000 claims description 73
238000000034 method Methods 0.000 claims description 70
108010073816 IgE Receptors Proteins 0.000 claims description 66
102000009438 IgE Receptors Human genes 0.000 claims description 66
210000004027 cell Anatomy 0.000 claims description 66
150000003839 salts Chemical class 0.000 claims description 65
102000000551 Syk Kinase Human genes 0.000 claims description 63
108010016672 Syk Kinase Proteins 0.000 claims description 63
239000000203 mixture Substances 0.000 claims description 63
125000001424 substituent group Chemical group 0.000 claims description 63
125000001072 heteroaryl group Chemical group 0.000 claims description 53
125000003118 aryl group Chemical group 0.000 claims description 48
239000012453 solvate Substances 0.000 claims description 45
150000001412 amines Chemical class 0.000 claims description 44
TVKGTSHBQZEFEE-UHFFFAOYSA-N 3-[[5-fluoro-2-(3-hydroxyanilino)pyrimidin-4-yl]amino]phenol Chemical compound OC1=CC=CC(NC=2N=C(NC=3C=C(O)C=CC=3)C(F)=CN=2)=C1 TVKGTSHBQZEFEE-UHFFFAOYSA-N 0.000 claims description 43
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 42
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 41
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 39
150000001204 N-oxides Chemical class 0.000 claims description 39
102000009109 Fc receptors Human genes 0.000 claims description 38
108010087819 Fc receptors Proteins 0.000 claims description 38
201000010099 disease Diseases 0.000 claims description 37
210000003630 histaminocyte Anatomy 0.000 claims description 33
125000000217 alkyl group Chemical group 0.000 claims description 32
150000004677 hydrates Chemical class 0.000 claims description 31
210000003651 basophil Anatomy 0.000 claims description 30
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 29
OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 29
150000002431 hydrogen Chemical class 0.000 claims description 28
125000006239 protecting group Chemical group 0.000 claims description 27
239000003814 drug Substances 0.000 claims description 26
238000000338 in vitro Methods 0.000 claims description 26
229910052799 carbon Inorganic materials 0.000 claims description 25
238000004519 manufacturing process Methods 0.000 claims description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 21
125000005842 heteroatom Chemical group 0.000 claims description 21
230000002401 inhibitory effect Effects 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 20
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 19
125000003710 aryl alkyl group Chemical group 0.000 claims description 19
150000002367 halogens Chemical class 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
229910052757 nitrogen Inorganic materials 0.000 claims description 17
206010020751 Hypersensitivity Diseases 0.000 claims description 16
150000002148 esters Chemical class 0.000 claims description 15
125000005843 halogen group Chemical group 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 15
208000006673 asthma Diseases 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 13
210000003979 eosinophil Anatomy 0.000 claims description 13
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 13
TZHVYWAFFGEGHM-UHFFFAOYSA-N methyl 5-[(2-chloro-5-fluoropyrimidin-4-yl)amino]-2-methoxybenzoate Chemical compound C1=C(OC)C(C(=O)OC)=CC(NC=2C(=CN=C(Cl)N=2)F)=C1 TZHVYWAFFGEGHM-UHFFFAOYSA-N 0.000 claims description 13
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 12
241001465754 Metazoa Species 0.000 claims description 12
125000004429 atom Chemical group 0.000 claims description 12
125000004122 cyclic group Chemical group 0.000 claims description 12
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
210000000440 neutrophil Anatomy 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 11
125000004438 haloalkoxy group Chemical group 0.000 claims description 11
239000000546 pharmaceutical excipient Substances 0.000 claims description 11
108010073807 IgG Receptors Proteins 0.000 claims description 10
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical class NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 10
210000001519 tissue Anatomy 0.000 claims description 10
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 9
241000282414 Homo sapiens Species 0.000 claims description 9
125000004404 heteroalkyl group Chemical group 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
125000000172 C5-C10 aryl group Chemical group 0.000 claims description 8
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 8
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 8
125000002757 morpholinyl group Chemical group 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000004193 piperazinyl group Chemical group 0.000 claims description 8
125000003386 piperidinyl group Chemical group 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 8
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
208000026935 allergic disease Diseases 0.000 claims description 7
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 7
206010061218 Inflammation Diseases 0.000 claims description 6
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
230000004054 inflammatory process Effects 0.000 claims description 6
208000010125 myocardial infarction Diseases 0.000 claims description 6
YCHAOQCQTCZKIA-UHFFFAOYSA-N 2,2-difluoro-4h-1,4-benzoxazin-3-one Chemical compound C1=CC=C2NC(=O)C(F)(F)OC2=C1 YCHAOQCQTCZKIA-UHFFFAOYSA-N 0.000 claims description 5
206010012438 Dermatitis atopic Diseases 0.000 claims description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
201000008937 atopic dermatitis Diseases 0.000 claims description 5
239000012634 fragment Substances 0.000 claims description 5
125000004043 oxo group Chemical group O=* 0.000 claims description 5
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 4
LJRUKUQEIHJTEL-UHFFFAOYSA-N 2,2-dimethyl-4h-1,4-benzoxazin-3-one Chemical compound C1=CC=C2NC(=O)C(C)(C)OC2=C1 LJRUKUQEIHJTEL-UHFFFAOYSA-N 0.000 claims description 4
RUPMYJYSOQCMBT-UHFFFAOYSA-N 2-n,4-n-bis(3-chlorophenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound N1=C(NC=2C=C(Cl)C=CC=2)C(F)=CN=C1NC1=CC=CC(Cl)=C1 RUPMYJYSOQCMBT-UHFFFAOYSA-N 0.000 claims description 4
RLHKNJYBMPFYGX-UHFFFAOYSA-N 3-[(2-chloro-5-fluoropyrimidin-4-yl)amino]phenol Chemical compound OC1=CC=CC(NC=2C(=CN=C(Cl)N=2)F)=C1 RLHKNJYBMPFYGX-UHFFFAOYSA-N 0.000 claims description 4
206010039710 Scleroderma Diseases 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
208000002551 irritable bowel syndrome Diseases 0.000 claims description 4
150000003233 pyrroles Chemical class 0.000 claims description 4
ONDPXXBSJNCOSA-UHFFFAOYSA-N tert-butyl n-[[5-[(2-chloro-5-fluoropyrimidin-4-yl)amino]-2-methoxycyclohexa-2,4-dien-1-ylidene]methyl]-n-propan-2-ylcarbamate Chemical compound C1C(=CN(C(C)C)C(=O)OC(C)(C)C)C(OC)=CC=C1NC1=NC(Cl)=NC=C1F ONDPXXBSJNCOSA-UHFFFAOYSA-N 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
CFHJEIDAGOQZSR-UHFFFAOYSA-N 4-[(2-chloro-5-fluoropyrimidin-4-yl)amino]-2,3-dimethylphenol Chemical compound CC1=C(O)C=CC(NC=2C(=CN=C(Cl)N=2)F)=C1C CFHJEIDAGOQZSR-UHFFFAOYSA-N 0.000 claims description 3
MOFAHEYAIBXIFZ-UHFFFAOYSA-N 5-fluoro-2-n,4-n-bis(3-methoxyphenyl)pyrimidine-2,4-diamine Chemical compound COC1=CC=CC(NC=2N=C(NC=3C=C(OC)C=CC=3)C(F)=CN=2)=C1 MOFAHEYAIBXIFZ-UHFFFAOYSA-N 0.000 claims description 3
206010016654 Fibrosis Diseases 0.000 claims description 3
208000002260 Keloid Diseases 0.000 claims description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
208000019695 Migraine disease Diseases 0.000 claims description 3
206010063837 Reperfusion injury Diseases 0.000 claims description 3
206010047163 Vasospasm Diseases 0.000 claims description 3
206010052428 Wound Diseases 0.000 claims description 3
208000027418 Wounds and injury Diseases 0.000 claims description 3
208000003455 anaphylaxis Diseases 0.000 claims description 3
230000006378 damage Effects 0.000 claims description 3
230000004761 fibrosis Effects 0.000 claims description 3
230000002757 inflammatory effect Effects 0.000 claims description 3
210000001117 keloid Anatomy 0.000 claims description 3
208000005069 pulmonary fibrosis Diseases 0.000 claims description 3
125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 2
125000006664 (C1-C3) perfluoroalkyl group Chemical group 0.000 claims description 2
125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 2
KSDCXJYIHUDQLT-UHFFFAOYSA-N 2-chloro-5-fluoro-n-[3-(trifluoromethoxy)phenyl]pyrimidin-4-amine Chemical compound FC1=CN=C(Cl)N=C1NC1=CC=CC(OC(F)(F)F)=C1 KSDCXJYIHUDQLT-UHFFFAOYSA-N 0.000 claims description 2
ZFUMNLUXIRJNID-UHFFFAOYSA-N 2-chloro-n-(4-chloro-3-methoxyphenyl)-5-fluoropyrimidin-4-amine Chemical compound C1=C(Cl)C(OC)=CC(NC=2C(=CN=C(Cl)N=2)F)=C1 ZFUMNLUXIRJNID-UHFFFAOYSA-N 0.000 claims description 2
CTIJRVCLQVLJMD-UHFFFAOYSA-N 2-chloro-n-[3-chloro-4-(trifluoromethoxy)phenyl]-5-fluoropyrimidin-4-amine Chemical compound FC1=CN=C(Cl)N=C1NC1=CC=C(OC(F)(F)F)C(Cl)=C1 CTIJRVCLQVLJMD-UHFFFAOYSA-N 0.000 claims description 2
RKCSEXIHMPENAW-UHFFFAOYSA-N 2-n,4-n-bis(2,4-dimethylphenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound CC1=CC(C)=CC=C1NC1=NC=C(F)C(NC=2C(=CC(C)=CC=2)C)=N1 RKCSEXIHMPENAW-UHFFFAOYSA-N 0.000 claims description 2
XCTIXWOSNPWXFO-UHFFFAOYSA-N 2-n,4-n-bis(2,5-dimethylphenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound CC1=CC=C(C)C(NC=2N=C(NC=3C(=CC=C(C)C=3)C)C(F)=CN=2)=C1 XCTIXWOSNPWXFO-UHFFFAOYSA-N 0.000 claims description 2
ATWJGWADQOMRDI-UHFFFAOYSA-N 2-n,4-n-bis(3,4-dimethylphenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound C1=C(C)C(C)=CC=C1NC1=NC=C(F)C(NC=2C=C(C)C(C)=CC=2)=N1 ATWJGWADQOMRDI-UHFFFAOYSA-N 0.000 claims description 2
JMFBVEWGVFCOKD-UHFFFAOYSA-N 2-n,4-n-bis(3-bromophenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound N1=C(NC=2C=C(Br)C=CC=2)C(F)=CN=C1NC1=CC=CC(Br)=C1 JMFBVEWGVFCOKD-UHFFFAOYSA-N 0.000 claims description 2
ARYRWGCJHFZYEP-UHFFFAOYSA-N 2-n,4-n-bis(3-chloro-4-methoxyphenyl)-5-fluoropyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC=C(F)C(NC=2C=C(Cl)C(OC)=CC=2)=N1 ARYRWGCJHFZYEP-UHFFFAOYSA-N 0.000 claims description 2
VBCQTAKBOBAXOU-UHFFFAOYSA-N 5-[(2-chloro-5-fluoropyrimidin-4-yl)amino]-2-methoxy-n-methylbenzamide Chemical compound C1=C(OC)C(C(=O)NC)=CC(NC=2C(=CN=C(Cl)N=2)F)=C1 VBCQTAKBOBAXOU-UHFFFAOYSA-N 0.000 claims description 2
208000019399 Colonic disease Diseases 0.000 claims description 2
208000004262 Food Hypersensitivity Diseases 0.000 claims description 2
229910019142 PO4 Inorganic materials 0.000 claims description 2
229920001774 Perfluoroether Polymers 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
125000002877 alkyl aryl group Chemical group 0.000 claims description 2
125000004103 aminoalkyl group Chemical group 0.000 claims description 2
125000004104 aryloxy group Chemical group 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
239000000539 dimer Substances 0.000 claims description 2
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 2
125000004428 fluoroalkoxy group Chemical group 0.000 claims description 2
125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
235000020932 food allergy Nutrition 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
230000001965 increasing effect Effects 0.000 claims description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
206010027599 migraine Diseases 0.000 claims description 2
230000011234 negative regulation of signal transduction Effects 0.000 claims description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
239000010452 phosphate Substances 0.000 claims description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 2
208000032544 Cicatrix Diseases 0.000 claims 2
102000009490 IgG Receptors Human genes 0.000 claims 2
231100000241 scar Toxicity 0.000 claims 2
230000037387 scars Effects 0.000 claims 2
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
AJKPUNIYEMWTIL-UHFFFAOYSA-N 2-[5-[[4-[(2,2-difluoro-3-oxo-4H-1,4-benzoxazin-6-yl)amino]-5-fluoropyrimidin-2-yl]amino]-2-methylcyclohexa-1,5-dien-1-yl]oxy-N-methylacetamide Chemical compound CNC(=O)COC1=C(C)CCC(Nc2ncc(F)c(Nc3ccc4OC(F)(F)C(=O)Nc4c3)n2)=C1 AJKPUNIYEMWTIL-UHFFFAOYSA-N 0.000 claims 1
HKJOLNFQZYWWPY-UHFFFAOYSA-N 2-chloro-5-fluoro-n-(3-phenylmethoxyphenyl)pyrimidin-4-amine Chemical compound FC1=CN=C(Cl)N=C1NC1=CC=CC(OCC=2C=CC=CC=2)=C1 HKJOLNFQZYWWPY-UHFFFAOYSA-N 0.000 claims 1
FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims 1
PVTXJGJDOHYFOX-UHFFFAOYSA-N 2h-1,4-benzoxazine Chemical compound C1=CC=C2N=CCOC2=C1 PVTXJGJDOHYFOX-UHFFFAOYSA-N 0.000 claims 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical group N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
206010002198 Anaphylactic reaction Diseases 0.000 claims 1
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
ZXSVSCZBXNJNJL-UHFFFAOYSA-N C1C(=CO)C(OC)=CC=C1NC1=NC(Cl)=NC=C1F Chemical compound C1C(=CO)C(OC)=CC=C1NC1=NC(Cl)=NC=C1F ZXSVSCZBXNJNJL-UHFFFAOYSA-N 0.000 claims 1
206010010741 Conjunctivitis Diseases 0.000 claims 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
125000005605 benzo group Chemical group 0.000 claims 1
125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims 1
125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 1
125000000168 pyrrolyl group Chemical group 0.000 claims 1
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238000010187 selection method Methods 0.000 claims 1
238000001356 surgical procedure Methods 0.000 claims 1
238000005481 NMR spectroscopy Methods 0.000 description 248
230000015572 biosynthetic process Effects 0.000 description 221
WHPFEQUEHBULBW-UHFFFAOYSA-N 2,4-dichloro-5-fluoropyrimidine Chemical compound FC1=CN=C(Cl)N=C1Cl WHPFEQUEHBULBW-UHFFFAOYSA-N 0.000 description 159
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 135
230000014759 maintenance of location Effects 0.000 description 107
ASRXSKWXNLKLKX-UHFFFAOYSA-N 2-chloro-n-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-fluoropyrimidin-4-amine Chemical compound FC1=CN=C(Cl)N=C1NC1=CC=C(OCCO2)C2=C1 ASRXSKWXNLKLKX-UHFFFAOYSA-N 0.000 description 58
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 50
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 50
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 46
238000003786 synthesis reaction Methods 0.000 description 45
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 40
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239000007787 solid Substances 0.000 description 38
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PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 28
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125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000002750 tryptase inhibitor Substances 0.000 description 1
108010063876 tyrosyl-1,2,3,4-tetrahydro-3-isoquinolinecarbonyl-phenylalanyl-phenylalanine Proteins 0.000 description 1
ZXYAAVBXHKCJJB-UHFFFAOYSA-N uracil-5-carboxylic acid Chemical compound OC(=O)C1=CNC(=O)NC1=O ZXYAAVBXHKCJJB-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
230000025033 vasoconstriction Effects 0.000 description 1
239000005526 vasoconstrictor agent Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
210000001048 venom Anatomy 0.000 description 1
239000002435 venom Substances 0.000 description 1
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238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

JP2003563490A 2002-02-01 2003-01-31 ２，４−ピリミジンジアミン化合物とその用途 Expired - Lifetime JP4658477B2 (ja)