TW200529838A

TW200529838A - Novel compounds

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Info

Publication number: TW200529838A
Authority: TW; Taiwan
Prior art keywords: amino; ethyl; methyl; phenyl; alkyl
Prior art date: 2004-02-10

Application number

TW094103740A

Other languages

English (en)

Chinese (zh)

Inventor

Jorgen Gustafsson

Karolina Lawitz

Antonios Nikitidis

Tesfaledet Mussie

Laurent David

Original Assignee

Astrazeneca Ab

Priority date

2004-02-10

Filing date

2005-02-04

Publication date

2005-09-16

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=31885281&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=TW200529838(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2005-02-04 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2005-09-16 Publication of TW200529838A publication Critical patent/TW200529838A/zh

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150000001875 compounds Chemical class 0.000 title claims abstract description 120
238000000034 method Methods 0.000 claims abstract description 22
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 claims abstract 2
102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 claims abstract 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 798
-1 CrCs alkane Oxy Chemical group 0.000 claims description 471
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 353
125000000217 alkyl group Chemical group 0.000 claims description 263
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 194
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 176
150000003839 salts Chemical class 0.000 claims description 109
150000001412 amines Chemical class 0.000 claims description 107
229910052757 nitrogen Inorganic materials 0.000 claims description 107
239000001301 oxygen Substances 0.000 claims description 106
229910052760 oxygen Inorganic materials 0.000 claims description 106
125000003277 amino group Chemical group 0.000 claims description 104
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 101
125000003545 alkoxy group Chemical group 0.000 claims description 100
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 98
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 88
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 88
239000001257 hydrogen Substances 0.000 claims description 88
229910052739 hydrogen Inorganic materials 0.000 claims description 88
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 87
229910052717 sulfur Inorganic materials 0.000 claims description 86
239000011593 sulfur Substances 0.000 claims description 85
BLTDCIWCFCUQCB-UHFFFAOYSA-N quionoline-3-carboxamide Natural products C1=CC=CC2=CC(C(=O)N)=CN=C21 BLTDCIWCFCUQCB-UHFFFAOYSA-N 0.000 claims description 80
229920006395 saturated elastomer Polymers 0.000 claims description 72
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 66
125000005842 heteroatom Chemical group 0.000 claims description 60
125000004093 cyano group Chemical group *C#N 0.000 claims description 57
125000006317 cyclopropyl amino group Chemical group 0.000 claims description 54
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 48
125000000623 heterocyclic group Chemical group 0.000 claims description 45
125000004433 nitrogen atom Chemical group N* 0.000 claims description 44
229910052736 halogen Inorganic materials 0.000 claims description 43
150000002367 halogens Chemical class 0.000 claims description 43
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 41
125000002950 monocyclic group Chemical group 0.000 claims description 38
125000001424 substituent group Chemical group 0.000 claims description 37
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 36
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 35
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 35
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 33
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 30
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 28
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 28
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 28
150000002431 hydrogen Chemical class 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 21
125000000753 cycloalkyl group Chemical group 0.000 claims description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
125000000304 alkynyl group Chemical group 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 16
239000007789 gas Substances 0.000 claims description 16
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 15
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 14
150000001540 azides Chemical class 0.000 claims description 14
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 12
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 12
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
201000010099 disease Diseases 0.000 claims description 12
125000003342 alkenyl group Chemical group 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 11
KPRVDOZCMGSORQ-UHFFFAOYSA-N quinoline-3-carboximidamide Chemical compound C1=CC=CC2=CC(C(=N)N)=CN=C21 KPRVDOZCMGSORQ-UHFFFAOYSA-N 0.000 claims description 11
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
150000003254 radicals Chemical class 0.000 claims description 10
239000012453 solvate Substances 0.000 claims description 10
125000004429 atom Chemical group 0.000 claims description 9
MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 7
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 7
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 7
229910052731 fluorine Chemical group 0.000 claims description 7
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 7
FVGUUJNEJJPLCS-UHFFFAOYSA-N pyridine-3-carboximidamide Chemical compound NC(=N)C1=CC=CN=C1 FVGUUJNEJJPLCS-UHFFFAOYSA-N 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 7
238000006467 substitution reaction Methods 0.000 claims description 7
229940124530 sulfonamide Drugs 0.000 claims description 7
238000011282 treatment Methods 0.000 claims description 7
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 6
206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 5
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims description 5
241001674048 Phthiraptera Species 0.000 claims description 5
150000001335 aliphatic alkanes Chemical group 0.000 claims description 5
SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 5
208000006673 asthma Diseases 0.000 claims description 5
125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 5
125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
206010028980 Neoplasm Diseases 0.000 claims description 4
206010052779 Transplant rejections Diseases 0.000 claims description 4
239000002671 adjuvant Substances 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
230000001363 autoimmune Effects 0.000 claims description 4
201000011510 cancer Diseases 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
206010012601 diabetes mellitus Diseases 0.000 claims description 4
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
235000013336 milk Nutrition 0.000 claims description 4
239000008267 milk Substances 0.000 claims description 4
210000004080 milk Anatomy 0.000 claims description 4
125000003226 pyrazolyl group Chemical group 0.000 claims description 4
239000004575 stone Substances 0.000 claims description 4
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 4
238000002054 transplantation Methods 0.000 claims description 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
208000011231 Crohn disease Diseases 0.000 claims description 3
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 3
208000024799 Thyroid disease Diseases 0.000 claims description 3
UGUUDTWORXNLAK-UHFFFAOYSA-N azidoalcohol Chemical compound ON=[N+]=[N-] UGUUDTWORXNLAK-UHFFFAOYSA-N 0.000 claims description 3
150000003857 carboxamides Chemical class 0.000 claims description 3
125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 3
230000000694 effects Effects 0.000 claims description 3
208000032839 leukemia Diseases 0.000 claims description 3
238000002844 melting Methods 0.000 claims description 3
229960000948 quinine Drugs 0.000 claims description 3
DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 claims description 3
206010039083 rhinitis Diseases 0.000 claims description 3
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
ZKDLEKHCSYEICO-UHFFFAOYSA-N 6,7-dimethoxyquinoline-3-carboxamide Chemical compound NC(=O)C1=CN=C2C=C(OC)C(OC)=CC2=C1 ZKDLEKHCSYEICO-UHFFFAOYSA-N 0.000 claims description 2
NLVPUORRLFNMCP-UHFFFAOYSA-N 6-methoxyquinoline-3-carboxamide Chemical compound N1=CC(C(N)=O)=CC2=CC(OC)=CC=C21 NLVPUORRLFNMCP-UHFFFAOYSA-N 0.000 claims description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 claims description 2
101100007769 Arabidopsis thaliana CRB gene Proteins 0.000 claims description 2
101100007773 Arabidopsis thaliana CRD gene Proteins 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
PNDKCRDVVKJPKG-WHERJAGFSA-N cenicriviroc Chemical compound C1=CC(OCCOCCCC)=CC=C1C1=CC=C(N(CC(C)C)CCC\C(=C/2)C(=O)NC=3C=CC(=CC=3)[S@@](=O)CC=3N(C=NC=3)CCC)C\2=C1 PNDKCRDVVKJPKG-WHERJAGFSA-N 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
RNIVAQHBBCJXJL-UHFFFAOYSA-N ethyl acetate;2,2,2-trifluoroacetic acid Chemical compound CCOC(C)=O.OC(=O)C(F)(F)F RNIVAQHBBCJXJL-UHFFFAOYSA-N 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
206010025135 lupus erythematosus Diseases 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000006308 propyl amino group Chemical group 0.000 claims description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
RQCNHUCCQJMSRG-UHFFFAOYSA-N tert-butyl piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1 RQCNHUCCQJMSRG-UHFFFAOYSA-N 0.000 claims description 2
NZKFFGZDNRWTTP-UHFFFAOYSA-N azidocyanamide Chemical compound [N-]=[N+]=NNC#N NZKFFGZDNRWTTP-UHFFFAOYSA-N 0.000 claims 3
125000003396 thiol group Chemical group [H]S* 0.000 claims 3
OQEBBZSWEGYTPG-UHFFFAOYSA-N 3-aminobutanoic acid Chemical compound CC(N)CC(O)=O OQEBBZSWEGYTPG-UHFFFAOYSA-N 0.000 claims 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 claims 2
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Chemical compound OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
ZTQNUTNKGQGWCM-UHFFFAOYSA-N 2-methoxyquinoline Chemical compound C1=CC=CC2=NC(OC)=CC=C21 ZTQNUTNKGQGWCM-UHFFFAOYSA-N 0.000 claims 1
KPOYTMZDCUXJBP-UHFFFAOYSA-N 3-cyclohexylpropan-1-amine Chemical compound NCCCC1CCCCC1 KPOYTMZDCUXJBP-UHFFFAOYSA-N 0.000 claims 1
VDJRDEXMDYOFNI-UHFFFAOYSA-N 4-[2-ethyl-3-[(2-hydroxypropylamino)methyl]anilino]-6,7-dimethoxyquinoline-3-carboxamide Chemical compound CCC1=C(CNCC(C)O)C=CC=C1NC1=C(C(N)=O)C=NC2=CC(OC)=C(OC)C=C12 VDJRDEXMDYOFNI-UHFFFAOYSA-N 0.000 claims 1
UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 claims 1
FYSOQIKOUXQYSU-UHFFFAOYSA-N 6-methoxypyridine-2-carboxamide Chemical compound COC1=CC=CC(C(N)=O)=N1 FYSOQIKOUXQYSU-UHFFFAOYSA-N 0.000 claims 1
CYSPWCARDHRYJX-UHFFFAOYSA-N 9h-fluoren-1-amine Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2N CYSPWCARDHRYJX-UHFFFAOYSA-N 0.000 claims 1
208000024827 Alzheimer disease Diseases 0.000 claims 1
241000196240 Characeae Species 0.000 claims 1
201000004624 Dermatitis Diseases 0.000 claims 1
HDMBHAKIUYWIRO-UHFFFAOYSA-N FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.COC1=NC2=CC=CC=C2C=C1C(=O)N Chemical compound FC(C(=O)O)(F)F.FC(C(=O)O)(F)F.COC1=NC2=CC=CC=C2C=C1C(=O)N HDMBHAKIUYWIRO-UHFFFAOYSA-N 0.000 claims 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
241000162682 Heterogen Species 0.000 claims 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
241001529936 Murinae Species 0.000 claims 1
235000010627 Phaseolus vulgaris Nutrition 0.000 claims 1
244000046052 Phaseolus vulgaris Species 0.000 claims 1
208000034189 Sclerosis Diseases 0.000 claims 1
208000002474 Tinea Diseases 0.000 claims 1
241000893966 Trichophyton verrucosum Species 0.000 claims 1
208000025865 Ulcer Diseases 0.000 claims 1
150000001345 alkine derivatives Chemical class 0.000 claims 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
229910052921 ammonium sulfate Inorganic materials 0.000 claims 1
239000001166 ammonium sulphate Substances 0.000 claims 1
BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims 1
229960001230 asparagine Drugs 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 claims 1
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
230000000747 cardiac effect Effects 0.000 claims 1
210000000078 claw Anatomy 0.000 claims 1
206010009887 colitis Diseases 0.000 claims 1
QWJNFFYFEKXZBF-UHFFFAOYSA-N cyanocyanamide Chemical compound N#CNC#N QWJNFFYFEKXZBF-UHFFFAOYSA-N 0.000 claims 1
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 claims 1
CVBMAZKKCSYWQR-WCGOZPBSSA-N deserpidine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=CC=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 CVBMAZKKCSYWQR-WCGOZPBSSA-N 0.000 claims 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
229940069417 doxy Drugs 0.000 claims 1
125000003700 epoxy group Chemical group 0.000 claims 1
GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
150000007857 hydrazones Chemical class 0.000 claims 1
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 1
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
125000005641 methacryl group Chemical group 0.000 claims 1
SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims 1
HKKDKUMUWRTAIA-UHFFFAOYSA-N nitridooxidocarbon(.) Chemical compound [O]C#N HKKDKUMUWRTAIA-UHFFFAOYSA-N 0.000 claims 1
OCPJZGYXJQLRCO-UHFFFAOYSA-N phosphanyl 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)OP OCPJZGYXJQLRCO-UHFFFAOYSA-N 0.000 claims 1
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
KFUSANSHCADHNJ-UHFFFAOYSA-N pyridine-3-carbohydrazide Chemical compound NNC(=O)C1=CC=CN=C1 KFUSANSHCADHNJ-UHFFFAOYSA-N 0.000 claims 1
SCGWSBWVMLOTLY-UHFFFAOYSA-N quinoline-3-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=CC2=CC(C(=O)N)=CN=C21 SCGWSBWVMLOTLY-UHFFFAOYSA-N 0.000 claims 1
230000001568 sexual effect Effects 0.000 claims 1
239000002689 soil Substances 0.000 claims 1
229940116269 uric acid Drugs 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 9
229940043355 kinase inhibitor Drugs 0.000 abstract description 2
239000003757 phosphotransferase inhibitor Substances 0.000 abstract description 2
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 234
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
239000000203 mixture Substances 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
108010019421 Janus Kinase 3 Proteins 0.000 description 23
102000006500 Janus Kinase 3 Human genes 0.000 description 23
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
239000000843 powder Substances 0.000 description 17
239000011541 reaction mixture Substances 0.000 description 14
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 13
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