JP2017524734A5

JP2017524734A5 -

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Publication number: JP2017524734A5
Authority: JP; Japan
Prior art keywords: amino; methyl; carbonyl; thienyl; pyrimidin
Prior art date: 2015-06-30
Legal status : Granted

Application number

JP2017521031A

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English (en)

Japanese (ja)

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JP6603712B2 (ja

JP2017524734A (ja

Filing date

2015-06-30

Publication date

2019-07-11

2015-06-30 Application filed filed Critical

2015-06-30 Priority claimed from PCT/US2015/038712 external-priority patent/WO2016004136A1/en

2017-08-31 Publication of JP2017524734A publication Critical patent/JP2017524734A/ja

2019-07-11 Publication of JP2017524734A5 publication Critical patent/JP2017524734A5/ja

2019-11-06 Application granted granted Critical

2019-11-06 Publication of JP6603712B2 publication Critical patent/JP6603712B2/ja

Status Active legal-status Critical Current

2035-06-30 Anticipated expiration legal-status Critical

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125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 388
FIYXUOWXHWJDAM-UHFFFAOYSA-N methyl sulfamate Chemical compound COS(N)(=O)=O FIYXUOWXHWJDAM-UHFFFAOYSA-N 0.000 claims description 372
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 264
-1 phenolyl Chemical group 0.000 claims description 243
229910052739 hydrogen Inorganic materials 0.000 claims description 166
239000001257 hydrogen Substances 0.000 claims description 166
150000002431 hydrogen Chemical class 0.000 claims description 96
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 96
125000000623 heterocyclic group Chemical group 0.000 claims description 94
150000001875 compounds Chemical class 0.000 claims description 85
229910052736 halogen Inorganic materials 0.000 claims description 79
125000002723 alicyclic group Chemical group 0.000 claims description 78
150000002367 halogens Chemical class 0.000 claims description 72
150000003839 salts Chemical class 0.000 claims description 72
125000003118 aryl group Chemical group 0.000 claims description 67
125000001544 thienyl group Chemical group 0.000 claims description 65
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 61
125000000217 alkyl group Chemical group 0.000 claims description 58
229910052799 carbon Inorganic materials 0.000 claims description 56
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 54
125000001931 aliphatic group Chemical group 0.000 claims description 52
125000004093 cyano group Chemical group *C#N 0.000 claims description 52
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
125000001072 heteroaryl group Chemical group 0.000 claims description 47
229910052757 nitrogen Inorganic materials 0.000 claims description 46
125000005842 heteroatom Chemical group 0.000 claims description 44
125000004122 cyclic group Chemical group 0.000 claims description 36
229910052760 oxygen Inorganic materials 0.000 claims description 36
206010028980 Neoplasm Diseases 0.000 claims description 28
201000011510 cancer Diseases 0.000 claims description 28
125000001153 fluoro group Chemical group F* 0.000 claims description 27
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 26
229910052717 sulfur Inorganic materials 0.000 claims description 23
150000001721 carbon Chemical group 0.000 claims description 22
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 22
125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims description 21
125000002947 alkylene group Chemical group 0.000 claims description 20
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 17
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 15
125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 14
125000002619 bicyclic group Chemical group 0.000 claims description 14
125000004428 fluoroalkoxy group Chemical group 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
239000008194 pharmaceutical composition Substances 0.000 claims description 12
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
239000003937 drug carrier Substances 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
125000006168 tricyclic group Chemical group 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 4
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
125000005647 linker group Chemical group 0.000 claims description 3
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 2
125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 2
PTHALMFXGRKILO-VCNAKFCDSA-N CNS(=O)(=O)O[C@@H]1C[C@H]([C@@H]([C@H]1O)O)NC2=NC=NC=C2C(=O)C3=CC(=C(S3)Cl)[C@H](C4=CC(=CC=C4)Cl)N Chemical compound CNS(=O)(=O)O[C@@H]1C[C@H]([C@@H]([C@H]1O)O)NC2=NC=NC=C2C(=O)C3=CC(=C(S3)Cl)[C@H](C4=CC(=CC=C4)Cl)N PTHALMFXGRKILO-VCNAKFCDSA-N 0.000 claims description 2
XRXCWWJFOODSNK-FZGRFCFCSA-N CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@@H](C1=NC(=CC=C1)Br)N)Cl)O)O)(=O)=O Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@@H](C1=NC(=CC=C1)Br)N)Cl)O)O)(=O)=O XRXCWWJFOODSNK-FZGRFCFCSA-N 0.000 claims description 2
IWXXRQFYMGYNOO-CLODTNMZSA-N CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1NCCC2=CC=C(C=C12)Br)C)O)O)(=O)=O Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1NCCC2=CC=C(C=C12)Br)C)O)O)(=O)=O IWXXRQFYMGYNOO-CLODTNMZSA-N 0.000 claims description 2
UXZHVDNHVNCQLZ-AJYQEWAOSA-N CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1NCCC2=CC=C(C=C12)Br)Cl)O)O)(=O)=O Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1NCCC2=CC=C(C=C12)Br)Cl)O)O)(=O)=O UXZHVDNHVNCQLZ-AJYQEWAOSA-N 0.000 claims description 2
MQVDZABZBXFHHO-AJYQEWAOSA-N CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1NCCC2=CC=C(C=C12)Cl)Cl)O)O)(=O)=O Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1NCCC2=CC=C(C=C12)Cl)Cl)O)O)(=O)=O MQVDZABZBXFHHO-AJYQEWAOSA-N 0.000 claims description 2
HINDPSUFSNQHRC-PGEXYDAJSA-N CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1OCCC2=CC=CC=C12)C)O)O)(=O)=O Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1OCCC2=CC=CC=C12)C)O)O)(=O)=O HINDPSUFSNQHRC-PGEXYDAJSA-N 0.000 claims description 2
DSKZVKRFEIHHGI-IJLGJDIWSA-N CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C1)[C@@](C)(C1=CC(=CC=C1)Br)N)O)O)(=O)=O Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C1)[C@@](C)(C1=CC(=CC=C1)Br)N)O)O)(=O)=O DSKZVKRFEIHHGI-IJLGJDIWSA-N 0.000 claims description 2
CBGXIBOZYAGHHY-OMEJVGOCSA-N CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C1)[C@H]1SCCC2=CC=C(C=C12)Cl)O)O)(=O)=O Chemical compound CNS(O[C@H]1[C@@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C1)[C@H]1SCCC2=CC=C(C=C12)Cl)O)O)(=O)=O CBGXIBOZYAGHHY-OMEJVGOCSA-N 0.000 claims description 2
IFRKRXRXWVYNIN-CAMXOCNWSA-N CNS(O[C@H]1[C@H](C[C@H](C1)N(C)C1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1OCCC2=CC=C(C=C12)Cl)CO)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)N(C)C1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1OCCC2=CC=C(C=C12)Cl)CO)O)(=O)=O IFRKRXRXWVYNIN-CAMXOCNWSA-N 0.000 claims description 2
OLOOXVUFQSTSNV-YCMMZOLNSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1OC=C(C1)[C@@](C)(C1=CC=CC=C1)O)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1OC=C(C1)[C@@](C)(C1=CC=CC=C1)O)O)(=O)=O OLOOXVUFQSTSNV-YCMMZOLNSA-N 0.000 claims description 2
KTKGZTQVZCCTLM-YZGWKJHDSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)CC1=CC(=CC=C1)Br)C)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)CC1=CC(=CC=C1)Br)C)O)(=O)=O KTKGZTQVZCCTLM-YZGWKJHDSA-N 0.000 claims description 2
BNUFJWRSWGSVOA-SNLNFDIBSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@@H](C)C1=CC(=CC=C1)Cl)C)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@@H](C)C1=CC(=CC=C1)Cl)C)O)(=O)=O BNUFJWRSWGSVOA-SNLNFDIBSA-N 0.000 claims description 2
MKBGHSMAZIEPIJ-DDESSGNOSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@@H]1OCCC=2C1=NC(=CC2)Cl)Cl)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@@H]1OCCC=2C1=NC(=CC2)Cl)Cl)O)(=O)=O MKBGHSMAZIEPIJ-DDESSGNOSA-N 0.000 claims description 2
CJBPBAPVIFJCBX-ACGMZIBCSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@@H]1OCCC=2C=NC(=CC21)Cl)Cl)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@@H]1OCCC=2C=NC(=CC21)Cl)Cl)O)(=O)=O CJBPBAPVIFJCBX-ACGMZIBCSA-N 0.000 claims description 2
NMUGEJYAXYGYES-GGVLSIRXSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@@H]1OCCN2C1=NC1=C2C=CC=C1)C)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@@H]1OCCN2C1=NC1=C2C=CC=C1)C)O)(=O)=O NMUGEJYAXYGYES-GGVLSIRXSA-N 0.000 claims description 2
HGSNEVLUMYKUMX-FTOGJNOLSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H](C(C)C)O)Cl)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H](C(C)C)O)Cl)O)(=O)=O HGSNEVLUMYKUMX-FTOGJNOLSA-N 0.000 claims description 2
HAOVXFRLZHNJDI-MINVPOHDSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H](C1=C(C=CC=C1)OC)O)Cl)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H](C1=C(C=CC=C1)OC)O)Cl)O)(=O)=O HAOVXFRLZHNJDI-MINVPOHDSA-N 0.000 claims description 2
WQWAEEPEZKMUMZ-GRGSLBFTSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H](CC1=CC=CC=C1)O)Cl)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H](CC1=CC=CC=C1)O)Cl)O)(=O)=O WQWAEEPEZKMUMZ-GRGSLBFTSA-N 0.000 claims description 2
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BKKGIDWBHUIVLT-JUOFYSQLSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1OCCC2=C1C=C(O2)Cl)C)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1OCCC2=C1C=C(O2)Cl)C)O)(=O)=O BKKGIDWBHUIVLT-JUOFYSQLSA-N 0.000 claims description 2
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VAJKCCLUOXDBHE-MXKZQLQBSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1OCCC2=CC=C(C=C12)C#C)C)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1OCCC2=CC=C(C=C12)C#C)C)O)(=O)=O VAJKCCLUOXDBHE-MXKZQLQBSA-N 0.000 claims description 2
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MKBGHSMAZIEPIJ-KCCDOTDQSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1OCCC=2C1=NC(=CC2)Cl)Cl)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1OCCC=2C1=NC(=CC2)Cl)Cl)O)(=O)=O MKBGHSMAZIEPIJ-KCCDOTDQSA-N 0.000 claims description 2
IJNZZXBFVPBCDT-CNPFDHCBSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1OCCC=2C1=NC=CC2)Cl)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1OCCC=2C1=NC=CC2)Cl)O)(=O)=O IJNZZXBFVPBCDT-CNPFDHCBSA-N 0.000 claims description 2
GIVZITISGYSQFZ-KBHIOQAXSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1OCCC=2C=NC(=CC21)Cl)C)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1OCCC=2C=NC(=CC21)Cl)C)O)(=O)=O GIVZITISGYSQFZ-KBHIOQAXSA-N 0.000 claims description 2
CJBPBAPVIFJCBX-NPZTYHQZSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1OCCC=2C=NC(=CC21)Cl)Cl)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1OCCC=2C=NC(=CC21)Cl)Cl)O)(=O)=O CJBPBAPVIFJCBX-NPZTYHQZSA-N 0.000 claims description 2
NMUGEJYAXYGYES-DINKTKQASA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1OCCN2C1=NC1=C2C=CC=C1)C)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1OCCN2C1=NC1=C2C=CC=C1)C)O)(=O)=O NMUGEJYAXYGYES-DINKTKQASA-N 0.000 claims description 2
LXFUMNSSXUDXGD-LRYKZCBQSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(N1)[C@H]1OCCC2=CC=C(C=C12)Cl)C)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(N1)[C@H]1OCCC2=CC=C(C=C12)Cl)C)O)(=O)=O LXFUMNSSXUDXGD-LRYKZCBQSA-N 0.000 claims description 2
ZEIZDXQCWLAPCV-SYKKWBAMSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=CC1)[C@@](C)(O)C1=CC(=CC=C1)Cl)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=CC1)[C@@](C)(O)C1=CC(=CC=C1)Cl)O)(=O)=O ZEIZDXQCWLAPCV-SYKKWBAMSA-N 0.000 claims description 2
BLANVFDOXJFELE-QHCFZIRBSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=CC1)[C@H]1OCCCC2=C1C=C(C=C2)Cl)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=CC1)[C@H]1OCCCC2=C1C=C(C=C2)Cl)O)(=O)=O BLANVFDOXJFELE-QHCFZIRBSA-N 0.000 claims description 2
PETVHEJERNEZFN-QNDJGXFYSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C1)CN1C[C@H](CCC1)C)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C1)CN1C[C@H](CCC1)C)O)(=O)=O PETVHEJERNEZFN-QNDJGXFYSA-N 0.000 claims description 2
CKSWVCMMOHMWHB-YCMMZOLNSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C1)[C@@](C)(C1=CC(=CC=C1)Cl)N)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C1)[C@@](C)(C1=CC(=CC=C1)Cl)N)O)(=O)=O CKSWVCMMOHMWHB-YCMMZOLNSA-N 0.000 claims description 2
BQVRNPPJYVGAIR-CXEBNRJLSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C1)[C@H]1OCCCC2=C1C=C(C=C2)Cl)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C1)[C@H]1OCCCC2=C1C=C(C=C2)Cl)O)(=O)=O BQVRNPPJYVGAIR-CXEBNRJLSA-N 0.000 claims description 2
HAKVACNLCRORIT-AFPVUDKHSA-N CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C1)[C@]1(OCCC1)C1=CC(=CC=C1)Cl)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C1)[C@]1(OCCC1)C1=CC(=CC=C1)Cl)O)(=O)=O HAKVACNLCRORIT-AFPVUDKHSA-N 0.000 claims description 2
GLMLYFJADOJXDP-CORBCRPWSA-N CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@@H]1OCCC2=CC=C(C=C12)Cl)C)F)O)(=O)=O Chemical compound CNS(O[C@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@@H]1OCCC2=CC=C(C=C12)Cl)C)F)O)(=O)=O GLMLYFJADOJXDP-CORBCRPWSA-N 0.000 claims description 2
241000238366 Cephalopoda Species 0.000 claims description 2
241001024304 Mino Species 0.000 claims description 2
DXEVQOXEXCQXPP-SJFSSXKUSA-N [(1R,2R,3R,4R)-3-fluoro-2-hydroxy-4-[[5-[4-[(3-iodophenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC1=CC(=CC=C1)I)F)O)(=O)=O DXEVQOXEXCQXPP-SJFSSXKUSA-N 0.000 claims description 2
BBKUCLXGFAGUSW-YCEFEEMOSA-N [(1R,2R,3R,4R)-4-[[5-(4-benzyl-5-chlorothiophene-2-carbonyl)pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CC1=CC=CC=C1)Cl)F)O)(=O)=O BBKUCLXGFAGUSW-YCEFEEMOSA-N 0.000 claims description 2
PNSSVEDETBRSFU-QDADHNENSA-N [(1R,2R,3R,4R)-4-[[5-[4-[(1S)-7-chloro-3,4-dihydro-1H-isochromen-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@@H]2C[C@H](COS(N)(=O)=O)[C@@H](O)[C@@H]2F)N=CN=C1)[C@H]1OCCC2=CC=C(Cl)C=C12 PNSSVEDETBRSFU-QDADHNENSA-N 0.000 claims description 2
GBLXROQNHOBQLL-ZQYQINFJSA-N [(1R,2R,3R,4R)-4-[[5-[4-[(3-bromophenyl)methyl]-5-methylfuran-2-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1OC(=C(C=1)CC1=CC(=CC=C1)Br)C)F)O)(=O)=O GBLXROQNHOBQLL-ZQYQINFJSA-N 0.000 claims description 2
SLWMYANJWPBDSJ-SJFSSXKUSA-N [(1R,2R,3R,4R)-4-[[5-[4-[(3-bromophenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC1=CC(=CC=C1)Br)F)O)(=O)=O SLWMYANJWPBDSJ-SJFSSXKUSA-N 0.000 claims description 2
SRDLCQZMYSOIKY-ZQYQINFJSA-N [(1R,2R,3R,4R)-4-[[5-[4-[(3-chlorophenyl)methyl]-5-methylfuran-2-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1OC(=C(C=1)CC1=CC(=CC=C1)Cl)C)F)O)(=O)=O SRDLCQZMYSOIKY-ZQYQINFJSA-N 0.000 claims description 2
JUHZTXCHJQMMQU-XWYOBAOASA-N [(1R,2R,3R,4R)-4-[[5-[5-[(3-chlorophenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-3-fluoro-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=CC=1)CC1=CC(=CC=C1)Cl)F)O)(=O)=O JUHZTXCHJQMMQU-XWYOBAOASA-N 0.000 claims description 2
GMWFKCZAZBSPSL-XAMZUMDUSA-N [(1R,2R,3S,4R)-2,3-dihydroxy-4-[[5-(5-phenylfuran-2-carbonyl)pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1OC(=CC=1)C1=CC=CC=C1)O)O)(=O)=O GMWFKCZAZBSPSL-XAMZUMDUSA-N 0.000 claims description 2
QEEDRTSRNRXVJB-MTMYUEJZSA-N [(1R,2R,3S,4R)-2,3-dihydroxy-4-[[5-[5-(2-hydroxypropan-2-yl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=CC=1)C(C)(C)O)O)O)(=O)=O QEEDRTSRNRXVJB-MTMYUEJZSA-N 0.000 claims description 2
OLUZHLGPXCAXQN-JTYAGIKBSA-N [(1R,2R,3S,4R)-4-[[2-chloro-5-(5-phenylfuran-2-carbonyl)pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@H]([C@@H](C1)NC1=NC(=NC=C1C(=O)C=1OC(=CC=1)C1=CC=CC=C1)Cl)O)O)(=O)=O OLUZHLGPXCAXQN-JTYAGIKBSA-N 0.000 claims description 2
BNUNUBSDPLCMIP-QTRJSKNGSA-N [(1R,2R,3S,4R)-4-[[5-(5-benzylfuran-2-carbonyl)pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1OC(=CC=1)CC1=CC=CC=C1)O)O)(=O)=O BNUNUBSDPLCMIP-QTRJSKNGSA-N 0.000 claims description 2
HQEWNFAQYBRCGY-QTRJSKNGSA-N [(1R,2R,3S,4R)-4-[[5-(5-benzylthiophene-2-carbonyl)pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=CC=1)CC1=CC=CC=C1)O)O)(=O)=O HQEWNFAQYBRCGY-QTRJSKNGSA-N 0.000 claims description 2
PKZKPEKAHPGUEO-BDRLQPNQSA-N [(1R,2R,3S,4R)-4-[[5-[4-[(1R)-1-amino-1-(3-bromophenyl)ethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@@](C)(C1=CC(=CC=C1)Br)N)O)O)(=O)=O PKZKPEKAHPGUEO-BDRLQPNQSA-N 0.000 claims description 2
JLQDZPJVRKFRSZ-BDRLQPNQSA-N [(1R,2R,3S,4R)-4-[[5-[4-[(1R)-1-amino-1-(3-chlorophenyl)ethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@@](C)(C1=CC(=CC=C1)Cl)N)O)O)(=O)=O JLQDZPJVRKFRSZ-BDRLQPNQSA-N 0.000 claims description 2
SYNSFWGFGVXRTK-XGVSIZRLSA-N [(1R,2R,3S,4R)-4-[[5-[4-[(1R)-7-bromo-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-chlorothiophene-2-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H]1NCCC2=CC=C(C=C12)Br)Cl)O)O)(=O)=O SYNSFWGFGVXRTK-XGVSIZRLSA-N 0.000 claims description 2
MQHUHCVBLCFGHN-KQARLDPYSA-N [(1R,2R,3S,4R)-4-[[5-[4-[(1R)-7-bromo-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@@H]2C[C@H](COS(N)(=O)=O)[C@@H](O)[C@H]2O)N=CN=C1)[C@@H]1NCCC2=C1C=C(Br)C=C2 MQHUHCVBLCFGHN-KQARLDPYSA-N 0.000 claims description 2
PKZKPEKAHPGUEO-LKHNGIBQSA-N [(1R,2R,3S,4R)-4-[[5-[4-[(1S)-1-amino-1-(3-bromophenyl)ethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@](C)(C1=CC(=CC=C1)Br)N)O)O)(=O)=O PKZKPEKAHPGUEO-LKHNGIBQSA-N 0.000 claims description 2
YFQYNSYXAPNHAL-WGYMDGOUSA-N [(1R,2R,3S,4R)-4-[[5-[4-[(3-bromophenyl)methyl]-5-chlorothiophene-2-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CC1=CC(=CC=C1)Br)Cl)O)O)(=O)=O YFQYNSYXAPNHAL-WGYMDGOUSA-N 0.000 claims description 2
IXDGYECSUOUIBG-JZURDYQRSA-N [(1R,2R,3S,4R)-4-[[5-[4-[(3-bromophenyl)methyl]-5-methyl-1,3-thiazole-2-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(N=1)CC1=CC(=CC=C1)Br)C)O)O)(=O)=O IXDGYECSUOUIBG-JZURDYQRSA-N 0.000 claims description 2
BNXIRSFXIMMSFU-QTRJSKNGSA-N [(1R,2R,3S,4R)-4-[[5-[4-[(3-bromophenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC1=CC(=CC=C1)Br)O)O)(=O)=O BNXIRSFXIMMSFU-QTRJSKNGSA-N 0.000 claims description 2
BLPBXLARXXOQHU-JZURDYQRSA-N [(1R,2R,3S,4R)-4-[[5-[4-[(3-chlorophenyl)methyl]-5-methyl-1,3-thiazole-2-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(N=1)CC1=CC(=CC=C1)Cl)C)O)O)(=O)=O BLPBXLARXXOQHU-JZURDYQRSA-N 0.000 claims description 2
XNPUBXPMRDMMNN-MSUGDQAASA-N [(1R,2R,3S,4R)-4-[[5-[4-[(R)-amino-(3-chlorophenyl)methyl]-5-chlorothiophene-2-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H](C1=CC(=CC=C1)Cl)N)Cl)O)O)(=O)=O XNPUBXPMRDMMNN-MSUGDQAASA-N 0.000 claims description 2
XNPUBXPMRDMMNN-FIABAKSMSA-N [(1R,2R,3S,4R)-4-[[5-[4-[(S)-amino-(3-chlorophenyl)methyl]-5-chlorothiophene-2-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@H](C1=CC(=CC=C1)Cl)N)Cl)O)O)(=O)=O XNPUBXPMRDMMNN-FIABAKSMSA-N 0.000 claims description 2
ZRXJRPCREKSXLD-JGZGQIEPSA-N [(1R,2R,3S,4R)-4-[[5-[5-(2-chlorophenyl)furan-2-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1OC(=CC=1)C1=C(C=CC=C1)Cl)O)O)(=O)=O ZRXJRPCREKSXLD-JGZGQIEPSA-N 0.000 claims description 2
OQCXIJHNFPRKGM-QKCSRTOESA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-(2-hydroxypropan-2-yl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)C(C)(C)O)O)(=O)=O OQCXIJHNFPRKGM-QKCSRTOESA-N 0.000 claims description 2
KSWJWCOPHNDJIQ-GGPKGHCWSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-(2-phenylethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CCC1=CC=CC=C1)O)(=O)=O KSWJWCOPHNDJIQ-GGPKGHCWSA-N 0.000 claims description 2
PDKIBWNJLCSCDU-WZRBSPASSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-(hydroxymethyl)furan-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1OC=C(C=1)CO)O)(=O)=O PDKIBWNJLCSCDU-WZRBSPASSA-N 0.000 claims description 2
LHRSDZIFNCMQCE-WZRBSPASSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-(hydroxymethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CO)O)(=O)=O LHRSDZIFNCMQCE-WZRBSPASSA-N 0.000 claims description 2
BFQCCPHMYLXFNT-FMKPAKJESA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-(imidazol-1-ylmethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CN1C=NC=C1)O)(=O)=O BFQCCPHMYLXFNT-FMKPAKJESA-N 0.000 claims description 2
GYUDWVNFJHVGBS-OPYAIIAOSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-(indol-1-ylmethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CN1C=CC2=CC=CC=C12)O)(=O)=O GYUDWVNFJHVGBS-OPYAIIAOSA-N 0.000 claims description 2
SQFDXJWOWULRJS-BZPMIXESSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-(methoxymethyl)furan-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1OC=C(C=1)COC)O)(=O)=O SQFDXJWOWULRJS-BZPMIXESSA-N 0.000 claims description 2
OIQNLHOWKQGOTO-BZPMIXESSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-(methoxymethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)COC)O)(=O)=O OIQNLHOWKQGOTO-BZPMIXESSA-N 0.000 claims description 2
HRJLEENWYWQALR-MDZRGWNJSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-(phenoxymethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)COC1=CC=CC=C1)O)(=O)=O HRJLEENWYWQALR-MDZRGWNJSA-N 0.000 claims description 2
QJRYTABJLBDESL-KHNCNGADSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[(1R)-1,2,3,4-tetrahydroisoquinolin-1-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound NS(=O)(=O)OC[C@H]1C[C@H](C[C@@H]1O)NC1=C(C=NC=N1)C(=O)C1=CC(=CS1)[C@@H]1NCCC2=C1C=CC=C2 QJRYTABJLBDESL-KHNCNGADSA-N 0.000 claims description 2
PGLPTWVTFUOZPC-ODZKNYGOSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[(1R)-1-phenylethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@H](C)C1=CC=CC=C1)O)(=O)=O PGLPTWVTFUOZPC-ODZKNYGOSA-N 0.000 claims description 2
PYNAADLPSUPCCX-CNQXDYACSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[(1S)-1-hydroxy-1-phenylethyl]furan-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1OC=C(C=1)[C@](C)(C1=CC=CC=C1)O)O)(=O)=O PYNAADLPSUPCCX-CNQXDYACSA-N 0.000 claims description 2
ONSHCFBAZOPFNF-NUJGCVRESA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[(2-methoxyphenoxy)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)COC1=C(C=CC=C1)OC)O)(=O)=O ONSHCFBAZOPFNF-NUJGCVRESA-N 0.000 claims description 2
CKJOVLGQHAQQSD-LMMKCTJWSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[(2-methylphenoxy)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)COC1=C(C=CC=C1)C)O)(=O)=O CKJOVLGQHAQQSD-LMMKCTJWSA-N 0.000 claims description 2
MKVJUCAAQKNKKU-OPYAIIAOSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[(2-propan-2-ylphenoxy)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)COC1=C(C=CC=C1)C(C)C)O)(=O)=O MKVJUCAAQKNKKU-OPYAIIAOSA-N 0.000 claims description 2
HEBRTCZXGPWQHK-IJQAFXTHSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[(2S)-2-phenyloxolan-2-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@@]1(OCCC1)C1=CC=CC=C1)O)(=O)=O HEBRTCZXGPWQHK-IJQAFXTHSA-N 0.000 claims description 2
RCQSNQIUSRZIBG-SUMDDJOVSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[(3-iodophenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC1=CC(=CC=C1)I)O)(=O)=O RCQSNQIUSRZIBG-SUMDDJOVSA-N 0.000 claims description 2
NZLGJGFPLZBGNV-MDZRGWNJSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[(3-methylphenyl)methyl]-1,3-thiazole-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(N=1)CC1=CC(=CC=C1)C)O)(=O)=O NZLGJGFPLZBGNV-MDZRGWNJSA-N 0.000 claims description 2
HCMUBBHTSFDSRP-GGPKGHCWSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[(3-methylphenyl)methyl]furan-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1OC=C(C=1)CC1=CC(=CC=C1)C)O)(=O)=O HCMUBBHTSFDSRP-GGPKGHCWSA-N 0.000 claims description 2
BJSPVARPZQVHCZ-GGPKGHCWSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[(3-methylphenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC1=CC(=CC=C1)C)O)(=O)=O BJSPVARPZQVHCZ-GGPKGHCWSA-N 0.000 claims description 2
DWOOEBPHAWRNBJ-HLIPFELVSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[(3-methylsulfanylphenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC1=CC(=CC=C1)SC)O)(=O)=O DWOOEBPHAWRNBJ-HLIPFELVSA-N 0.000 claims description 2
UDXOYUIYAOBYAP-UNEWFSDZSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[(4-iodopyrazol-1-yl)methyl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CN1N=CC(=C1)I)C)O)(=O)=O UDXOYUIYAOBYAP-UNEWFSDZSA-N 0.000 claims description 2
RGRRIOQTLCPHRN-VIZSFHNOSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[(4-phenylpiperazin-1-yl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CN1CCN(CC1)C1=CC=CC=C1)O)(=O)=O RGRRIOQTLCPHRN-VIZSFHNOSA-N 0.000 claims description 2
JFXWKSXMOTUAKA-RKVPGOIHSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[(5-methylfuran-2-yl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC=1OC(=CC=1)C)O)(=O)=O JFXWKSXMOTUAKA-RKVPGOIHSA-N 0.000 claims description 2
HBGUJKMFODJKJN-PWHSHALESA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[(6-methoxy-2,3-dihydroindol-1-yl)methyl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CN1CCC2=CC=C(C=C12)OC)C)O)(=O)=O HBGUJKMFODJKJN-PWHSHALESA-N 0.000 claims description 2
PUVXZQDCUWJXOS-GGPKGHCWSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[2-(2-methoxyphenyl)ethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CCC1=C(C=CC=C1)OC)O)(=O)=O PUVXZQDCUWJXOS-GGPKGHCWSA-N 0.000 claims description 2
ZLPVMENFIYEEOD-XPKDYRNWSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[[4-(trifluoromethyl)pyrazol-1-yl]methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CN1N=CC(=C1)C(F)(F)F)O)(=O)=O ZLPVMENFIYEEOD-XPKDYRNWSA-N 0.000 claims description 2
HODSSCWCAFSFMI-UHOFOFEASA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[[5-(trifluoromethyl)furan-2-yl]methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C1)CC=1OC(=CC1)C(F)(F)F)O)(=O)=O HODSSCWCAFSFMI-UHOFOFEASA-N 0.000 claims description 2
XTDQJHXCIBDWJU-BLIXFSHQSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[[6-(trifluoromethyl)indol-1-yl]methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CN1C=CC2=CC=C(C=C12)C(F)(F)F)O)(=O)=O XTDQJHXCIBDWJU-BLIXFSHQSA-N 0.000 claims description 2
KVJQGJIIDBARNY-WZRBSPASSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[5-(2-hydroxypropan-2-yl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=CC=1)C(C)(C)O)O)(=O)=O KVJQGJIIDBARNY-WZRBSPASSA-N 0.000 claims description 2
VSOHAUTWFIIXRU-BREBYQMCSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[5-(hydroxymethyl)furan-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1OC(=CC=1)CO)O)(=O)=O VSOHAUTWFIIXRU-BREBYQMCSA-N 0.000 claims description 2
LEKZKECGNGEWBQ-GYSYKLTISA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[5-(methoxymethyl)furan-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1OC(=CC=1)COC)O)(=O)=O LEKZKECGNGEWBQ-GYSYKLTISA-N 0.000 claims description 2
NZGAASGWUYDBAN-INMHGKMJSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[5-methyl-4-(pyrazol-1-ylmethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CN1N=CC=C1)C)O)(=O)=O NZGAASGWUYDBAN-INMHGKMJSA-N 0.000 claims description 2
CRVLZGMZPZEGKG-SBHAEUEKSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[5-methyl-4-[(3-methylphenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CC1=CC(=CC=C1)C)C)O)(=O)=O CRVLZGMZPZEGKG-SBHAEUEKSA-N 0.000 claims description 2
UJMRJDNSVSWCFO-NUJGCVRESA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[5-methyl-4-[(4-methylpyrazol-1-yl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CN1N=CC(=C1)C)C)O)(=O)=O UJMRJDNSVSWCFO-NUJGCVRESA-N 0.000 claims description 2
QVVJEFJGRNRGMU-XQYFXQGPSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[5-methyl-4-[(4S)-2-(trifluoromethyl)-6,7-dihydro-4H-pyrano[3,4-d][1,3]thiazol-4-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H]1OCCC2=C1N=C(S2)C(F)(F)F)C)O)(=O)=O QVVJEFJGRNRGMU-XQYFXQGPSA-N 0.000 claims description 2
JQBLGKYKWGHVSY-CJOHGPIESA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[5-methyl-4-[(8S)-2-(trifluoromethyl)-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H]1OCCN2C1=NC(=C2)C(F)(F)F)C)O)(=O)=O JQBLGKYKWGHVSY-CJOHGPIESA-N 0.000 claims description 2
MECVDOYAMFZUJV-YMPLYOIOSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[5-methyl-4-[(8S)-2-(trifluoromethyl)-6,8-dihydro-5H-pyrano[3,4-b]pyridin-8-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H]1OCCC=2C1=NC(=CC=2)C(F)(F)F)C)O)(=O)=O MECVDOYAMFZUJV-YMPLYOIOSA-N 0.000 claims description 2
NGJUJYVPUZXTHI-FJFUSWKQSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[5-methyl-4-[(8S)-2-methyl-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H]1OCCN2C1=NC(=C2)C)C)O)(=O)=O NGJUJYVPUZXTHI-FJFUSWKQSA-N 0.000 claims description 2
JDLVNLYJIJSEJK-FJFUSWKQSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[5-methyl-4-[(8S)-3-methyl-6,8-dihydro-5H-imidazo[2,1-c][1,4]oxazin-8-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H]1OCCN2C1=NC=C2C)C)O)(=O)=O JDLVNLYJIJSEJK-FJFUSWKQSA-N 0.000 claims description 2
JHCNFTALYWRNLE-QOOVHSOYSA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[5-methyl-4-[(R)-[3-(trifluoromethyl)phenyl]sulfinyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[S@](=O)C1=CC(=CC=C1)C(F)(F)F)C)O)(=O)=O JHCNFTALYWRNLE-QOOVHSOYSA-N 0.000 claims description 2
CXZVYQZESKGQJG-OYRHQHFDSA-N [(1R,2S,4R)-4-[[5-(4,5-dibenzylfuran-2-carbonyl)pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1OC(=C(C=1)CC1=CC=CC=C1)CC1=CC=CC=C1)O)(=O)=O CXZVYQZESKGQJG-OYRHQHFDSA-N 0.000 claims description 2
VVAATQOKCQZITB-OYRHQHFDSA-N [(1R,2S,4R)-4-[[5-(4,5-dibenzylthiophene-2-carbonyl)pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CC1=CC=CC=C1)CC1=CC=CC=C1)O)(=O)=O VVAATQOKCQZITB-OYRHQHFDSA-N 0.000 claims description 2
DLCWAGWRPPFZMP-BREBYQMCSA-N [(1R,2S,4R)-4-[[5-(4-acetyl-5-chlorothiophene-2-carbonyl)pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)C(C)=O)Cl)O)(=O)=O DLCWAGWRPPFZMP-BREBYQMCSA-N 0.000 claims description 2
DVRGJYPOUNPDBF-BZPMIXESSA-N [(1R,2S,4R)-4-[[5-(4-acetylfuran-2-carbonyl)pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1OC=C(C=1)C(C)=O)O)(=O)=O DVRGJYPOUNPDBF-BZPMIXESSA-N 0.000 claims description 2
YJYSEDLYNWJECJ-QKCSRTOESA-N [(1R,2S,4R)-4-[[5-(4-acetylthiophene-2-carbonyl)pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)C(C)=O)O)(=O)=O YJYSEDLYNWJECJ-QKCSRTOESA-N 0.000 claims description 2
JDUOHLXIAXEAQX-CPUCHLNUSA-N [(1R,2S,4R)-4-[[5-(4-benzoyl-5-chlorothiophene-2-carbonyl)pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)C(C1=CC=CC=C1)=O)Cl)O)(=O)=O JDUOHLXIAXEAQX-CPUCHLNUSA-N 0.000 claims description 2
LFAHBAQSIFIHRN-KYJSFNMBSA-N [(1R,2S,4R)-4-[[5-(4-benzoylfuran-2-carbonyl)pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1OC=C(C=1)C(C1=CC=CC=C1)=O)O)(=O)=O LFAHBAQSIFIHRN-KYJSFNMBSA-N 0.000 claims description 2
WYLMPZNGCIDRFA-NUJGCVRESA-N [(1R,2S,4R)-4-[[5-(4-benzyl-5-chlorothiophene-2-carbonyl)pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CC1=CC=CC=C1)Cl)O)(=O)=O WYLMPZNGCIDRFA-NUJGCVRESA-N 0.000 claims description 2
SLIBWKOMCZPUMX-LMMKCTJWSA-N [(1R,2S,4R)-4-[[5-(4-benzylthiophene-2-carbonyl)pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC1=CC=CC=C1)O)(=O)=O SLIBWKOMCZPUMX-LMMKCTJWSA-N 0.000 claims description 2
ODGIAWFGPURSET-MDZRGWNJSA-N [(1R,2S,4R)-4-[[5-(5-benzylfuran-2-carbonyl)pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1OC(=CC=1)CC1=CC=CC=C1)O)(=O)=O ODGIAWFGPURSET-MDZRGWNJSA-N 0.000 claims description 2
VVUYPQBRIXDANM-SBHAEUEKSA-N [(1R,2S,4R)-4-[[5-[4-(1,3-dihydroisoindol-2-ylmethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CN1CC2=CC=CC=C2C1)O)(=O)=O VVUYPQBRIXDANM-SBHAEUEKSA-N 0.000 claims description 2
CBCHFKDVPCARER-INMHGKMJSA-N [(1R,2S,4R)-4-[[5-[4-(2,5-dihydrofuran-3-ylmethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC=1COCC=1)O)(=O)=O CBCHFKDVPCARER-INMHGKMJSA-N 0.000 claims description 2
QMHYWFKLDYGOEO-INMHGKMJSA-N [(1R,2S,4R)-4-[[5-[4-(2,5-dihydropyrrol-1-ylmethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CN1CC=CC1)O)(=O)=O QMHYWFKLDYGOEO-INMHGKMJSA-N 0.000 claims description 2
KGPPEEBKRZGYEW-SJBKTWHCSA-N [(1R,2S,4R)-4-[[5-[4-(3,4-dihydro-1H-isoquinolin-2-ylmethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CN1CC2=CC=CC=C2CC1)O)(=O)=O KGPPEEBKRZGYEW-SJBKTWHCSA-N 0.000 claims description 2
UTHBOQJWVWIXPA-NUJGCVRESA-N [(1R,2S,4R)-4-[[5-[4-(3,6-dihydro-2H-pyran-4-ylmethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC=1CCOCC=1)O)(=O)=O UTHBOQJWVWIXPA-NUJGCVRESA-N 0.000 claims description 2
IMVFMGZNKZPZDJ-NUJGCVRESA-N [(1R,2S,4R)-4-[[5-[4-(3,6-dihydro-2H-pyridin-1-ylmethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CN1CCC=CC1)O)(=O)=O IMVFMGZNKZPZDJ-NUJGCVRESA-N 0.000 claims description 2
ZKNCPKKLGZTVRC-NUJGCVRESA-N [(1R,2S,4R)-4-[[5-[4-(3,6-dihydro-2H-thiopyran-4-ylmethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC=1CCSCC=1)O)(=O)=O ZKNCPKKLGZTVRC-NUJGCVRESA-N 0.000 claims description 2
IQTJYBBWJRXYAD-SIIHOXLZSA-N [(1R,2S,4R)-4-[[5-[4-(3-chlorophenyl)sulfanyl-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)SC1=CC(=CC=C1)Cl)C)O)(=O)=O IQTJYBBWJRXYAD-SIIHOXLZSA-N 0.000 claims description 2
MUYQPWDJPSORDP-LBTNJELSSA-N [(1R,2S,4R)-4-[[5-[4-(benzenesulfonyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)S(=O)(=O)C1=CC=CC=C1)O)(=O)=O MUYQPWDJPSORDP-LBTNJELSSA-N 0.000 claims description 2
YRABUCYXBUUZKT-QINHECLXSA-N [(1R,2S,4R)-4-[[5-[4-(benzimidazol-1-ylmethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CN1C=NC2=C1C=CC=C2)O)(=O)=O YRABUCYXBUUZKT-QINHECLXSA-N 0.000 claims description 2
PKTZIYNAAIIHCH-LMMKCTJWSA-N [(1R,2S,4R)-4-[[5-[4-(cyclohexen-1-ylmethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC1=CCCCC1)O)(=O)=O PKTZIYNAAIIHCH-LMMKCTJWSA-N 0.000 claims description 2
PPIPRXSHFCYMMD-LMMKCTJWSA-N [(1R,2S,4R)-4-[[5-[4-(cyclohexylmethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound NS(=O)(=O)OC[C@H]1C[C@H](C[C@@H]1O)NC1=C(C=NC=N1)C(=O)C1=CC(CC2CCCCC2)=CS1 PPIPRXSHFCYMMD-LMMKCTJWSA-N 0.000 claims description 2
MBGLHNZZDMBCOK-ITNDPZETSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-1-(3-chlorophenyl)ethyl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@H](C)C1=CC(=CC=C1)Cl)C)O)(=O)=O MBGLHNZZDMBCOK-ITNDPZETSA-N 0.000 claims description 2
VTYUOMASBKDZEV-RWDRWCIPSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound NS(=O)(=O)OC[C@H]1C[C@H](C[C@@H]1O)NC1=C(C=NC=N1)C(=O)C1=CC(=CS1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 VTYUOMASBKDZEV-RWDRWCIPSA-N 0.000 claims description 2
QIOFTKBACCGQKK-UUIWEUTOSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydronaphthalen-1-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@@H]1CCCC2=CC=C(C=C12)Cl)O)(=O)=O QIOFTKBACCGQKK-UUIWEUTOSA-N 0.000 claims description 2
HBPZJIULHFGCQT-FNOAWNLGSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-3,4-dihydro-1H-isochromen-1-yl]-5-(difluoromethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound NS(=O)(=O)OC[C@H]1C[C@H](C[C@@H]1O)NC1=C(C=NC=N1)C(=O)C1=CC([C@@H]2OCCC3=CC=C(Cl)C=C23)=C(S1)C(F)F HBPZJIULHFGCQT-FNOAWNLGSA-N 0.000 claims description 2
WVFGWEZLNGGUQY-LRUMHDBSSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-3,4-dihydro-1H-isochromen-1-yl]-5-(hydroxymethyl)thiophene-2-carbonyl]pyrimidin-4-yl]-methylamino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)N(C)C1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H]1OCCC2=CC=C(C=C12)Cl)CO)O)(=O)=O WVFGWEZLNGGUQY-LRUMHDBSSA-N 0.000 claims description 2
YKFKIVBEJIVWGY-NBHJVPQVSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-3,4-dihydro-1H-isochromen-1-yl]-5-methyl-1,3-thiazole-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(N=1)[C@@H]1OCCC2=CC=C(C=C12)Cl)C)O)(=O)=O YKFKIVBEJIVWGY-NBHJVPQVSA-N 0.000 claims description 2
FCJKGSGGZZOGSE-XAVKYBOGSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-3,4-dihydro-1H-isochromen-1-yl]-5-methylfuran-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1OC(=C(C=1)[C@@H]1OCCC2=CC=C(C=C12)Cl)C)O)(=O)=O FCJKGSGGZZOGSE-XAVKYBOGSA-N 0.000 claims description 2
XSEXBSTXKYGUFQ-CPMLIZHXSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-3,4-dihydro-1H-pyrano[4,3-c]pyridin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H]1OCCC=2C=NC(=CC=21)Cl)C)O)(=O)=O XSEXBSTXKYGUFQ-CPMLIZHXSA-N 0.000 claims description 2
FBEUALYMBOBMCX-GZEIAWQZSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-4,4-difluoro-1,3-dihydroisochromen-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H]1OCC(C2=CC=C(C=C12)Cl)(F)F)C)O)(=O)=O FBEUALYMBOBMCX-GZEIAWQZSA-N 0.000 claims description 2
OUFVDTMLORSLTH-UYDHNTGBSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-4,4-difluoro-1,3-dihydroisochromen-1-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@@H]1OCC(C2=CC=C(C=C12)Cl)(F)F)O)(=O)=O OUFVDTMLORSLTH-UYDHNTGBSA-N 0.000 claims description 2
UTWAPAOTHMWXFN-JXZKETHXSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-cyclopropyl-3,4-dihydro-1H-isochromen-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H]1OCCC2=CC=C(C=C12)C1CC1)C)O)(=O)=O UTWAPAOTHMWXFN-JXZKETHXSA-N 0.000 claims description 2
IFRKOWVBYQAKQA-UESCSWIMSA-N [(1R,2S,4R)-4-[[5-[4-[(1S)-1-(3-bromophenyl)-1-hydroxyethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@@](C)(O)C1=CC(=CC=C1)Br)O)(=O)=O IFRKOWVBYQAKQA-UESCSWIMSA-N 0.000 claims description 2
SNOFVVQJCNZQNM-WEGMGINNSA-N [(1R,2S,4R)-4-[[5-[4-[(1S)-1-(3-chlorophenyl)-1-hydroxyethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@@](C)(O)C1=CC(=CC=C1)Cl)O)(=O)=O SNOFVVQJCNZQNM-WEGMGINNSA-N 0.000 claims description 2
MCVBNJJPKVQNHA-UESCSWIMSA-N [(1R,2S,4R)-4-[[5-[4-[(1S)-1-(3-chlorophenyl)-1-hydroxyethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@@](C)(O)C1=CC(=CC=C1)Cl)O)(=O)=O MCVBNJJPKVQNHA-UESCSWIMSA-N 0.000 claims description 2
MBGLHNZZDMBCOK-SFUJROHXSA-N [(1R,2S,4R)-4-[[5-[4-[(1S)-1-(3-chlorophenyl)ethyl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H](C)C1=CC(=CC=C1)Cl)C)O)(=O)=O MBGLHNZZDMBCOK-SFUJROHXSA-N 0.000 claims description 2
VGYQRRZWURTPID-FSPMTTQMSA-N [(1R,2S,4R)-4-[[5-[4-[(1S)-1-(3-chlorophenyl)ethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@@H](C)C1=CC(=CC=C1)Cl)O)(=O)=O VGYQRRZWURTPID-FSPMTTQMSA-N 0.000 claims description 2
VTCKDSBOHFVHJP-IZUJZYSFSA-N [(1R,2S,4R)-4-[[5-[4-[(1S)-6-chloro-2-methyl-1,3-dihydroisoindol-1-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@H]1N(CC2=CC=C(C=C12)Cl)C)O)(=O)=O VTCKDSBOHFVHJP-IZUJZYSFSA-N 0.000 claims description 2
RSYHHQRWJJELHO-DZVNEVJTSA-N [(1R,2S,4R)-4-[[5-[4-[(1S)-7-chloro-3,4-dihydro-1H-isochromen-1-yl]-5-(difluoromethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@H]1OCCC2=CC=C(C=C12)Cl)C(F)F)O)(=O)=O RSYHHQRWJJELHO-DZVNEVJTSA-N 0.000 claims description 2
XFDHRQZNMLGPOV-XFIWCOJDSA-N [(1R,2S,4R)-4-[[5-[4-[(1S)-7-chloro-4,4-difluoro-1,3-dihydroisochromen-1-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C1)[C@H]1OCC(C2=CC=C(C=C12)Cl)(F)F)O)(=O)=O XFDHRQZNMLGPOV-XFIWCOJDSA-N 0.000 claims description 2
ZBPSHNLJFNEXCC-CPUCHLNUSA-N [(1R,2S,4R)-4-[[5-[4-[(2,3-dichlorophenoxy)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)COC1=C(C(=CC=C1)Cl)Cl)O)(=O)=O ZBPSHNLJFNEXCC-CPUCHLNUSA-N 0.000 claims description 2
DAXMSUIKQXIZQY-RKVPGOIHSA-N [(1R,2S,4R)-4-[[5-[4-[(2-bromophenoxy)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)COC1=C(C=CC=C1)Br)O)(=O)=O DAXMSUIKQXIZQY-RKVPGOIHSA-N 0.000 claims description 2
KEMPAPGBCNOJKB-RKVPGOIHSA-N [(1R,2S,4R)-4-[[5-[4-[(2-chlorophenoxy)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)COC1=C(C=CC=C1)Cl)O)(=O)=O KEMPAPGBCNOJKB-RKVPGOIHSA-N 0.000 claims description 2
ZSJNAILODQKGMV-MDZRGWNJSA-N [(1R,2S,4R)-4-[[5-[4-[(2-chlorophenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC1=C(C=CC=C1)Cl)O)(=O)=O ZSJNAILODQKGMV-MDZRGWNJSA-N 0.000 claims description 2
ZYUPXKSMRBOJOE-RKVPGOIHSA-N [(1R,2S,4R)-4-[[5-[4-[(2-chlorophenyl)sulfanylmethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CSC1=C(C=CC=C1)Cl)O)(=O)=O ZYUPXKSMRBOJOE-RKVPGOIHSA-N 0.000 claims description 2
ITMGYZNWNDLCRU-LMMKCTJWSA-N [(1R,2S,4R)-4-[[5-[4-[(2-cyanophenoxy)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)COC1=C(C=CC=C1)C#N)O)(=O)=O ITMGYZNWNDLCRU-LMMKCTJWSA-N 0.000 claims description 2
BHNQUOBVWVACHM-LMMKCTJWSA-N [(1R,2S,4R)-4-[[5-[4-[(2-ethoxyphenoxy)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)COC1=C(C=CC=C1)OCC)O)(=O)=O BHNQUOBVWVACHM-LMMKCTJWSA-N 0.000 claims description 2
UGGUYVNRWLIAHX-GGPKGHCWSA-N [(1R,2S,4R)-4-[[5-[4-[(2-ethylphenoxy)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)COC1=C(C=CC=C1)CC)O)(=O)=O UGGUYVNRWLIAHX-GGPKGHCWSA-N 0.000 claims description 2
JTIXRQWIKCEJNY-BKRBWDDHSA-N [(1R,2S,4R)-4-[[5-[4-[(2R)-2-(3-chlorophenyl)oxolan-2-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@]1(OCCC1)C1=CC(=CC=C1)Cl)O)(=O)=O JTIXRQWIKCEJNY-BKRBWDDHSA-N 0.000 claims description 2
DBFYZJSPJAHRQD-AFPVUDKHSA-N [(1R,2S,4R)-4-[[5-[4-[(2R)-2-(3-chlorophenyl)pyrrolidin-2-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@]1(NCCC1)C1=CC(=CC=C1)Cl)O)(=O)=O DBFYZJSPJAHRQD-AFPVUDKHSA-N 0.000 claims description 2
RLFUEKJWOLYUTD-WOPBBPBGSA-N [(1R,2S,4R)-4-[[5-[4-[(2S)-2-(3-chlorophenyl)pyrrolidin-2-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound NS(=O)(=O)OC[C@H]1C[C@H](C[C@@H]1O)NC1=C(C=NC=N1)C(=O)C1=CC(=CS1)[C@]1(CCCN1)C1=CC(Cl)=CC=C1 RLFUEKJWOLYUTD-WOPBBPBGSA-N 0.000 claims description 2
KTTYKRWRJGCSDG-IJQAFXTHSA-N [(1R,2S,4R)-4-[[5-[4-[(2S)-2-(cyclohexen-1-yl)oxolan-2-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@@]1(OCCC1)C1=CCCCC1)O)(=O)=O KTTYKRWRJGCSDG-IJQAFXTHSA-N 0.000 claims description 2
VYSOBZAIKOWLRC-IJQAFXTHSA-N [(1R,2S,4R)-4-[[5-[4-[(2S)-2-cyclohexyloxolan-2-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@@]1(OCCC1)C1CCCCC1)O)(=O)=O VYSOBZAIKOWLRC-IJQAFXTHSA-N 0.000 claims description 2
ZNPBWWKJFQSBCL-GHBLSXJESA-N [(1R,2S,4R)-4-[[5-[4-[(2S)-2-cyclopropyloxolan-2-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@@]1(OCCC1)C1CC1)O)(=O)=O ZNPBWWKJFQSBCL-GHBLSXJESA-N 0.000 claims description 2
QOPWODSTOVGDQG-INMHGKMJSA-N [(1R,2S,4R)-4-[[5-[4-[(3,3-difluoropiperidin-1-yl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CN1CC(CCC1)(F)F)O)(=O)=O QOPWODSTOVGDQG-INMHGKMJSA-N 0.000 claims description 2
KLJODDHXXWNDAB-FMKPAKJESA-N [(1R,2S,4R)-4-[[5-[4-[(3,3-difluoropyrrolidin-1-yl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CN1CC(CC1)(F)F)O)(=O)=O KLJODDHXXWNDAB-FMKPAKJESA-N 0.000 claims description 2
YCJGBXRYRPAMMH-KYJSFNMBSA-N [(1R,2S,4R)-4-[[5-[4-[(3-bromophenyl)methyl]-5-chlorothiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CC1=CC(=CC=C1)Br)Cl)O)(=O)=O YCJGBXRYRPAMMH-KYJSFNMBSA-N 0.000 claims description 2
JUVWGUHJFQQESY-SUMDDJOVSA-N [(1R,2S,4R)-4-[[5-[4-[(3-bromophenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC1=CC(=CC=C1)Br)O)(=O)=O JUVWGUHJFQQESY-SUMDDJOVSA-N 0.000 claims description 2
FIONUXZGEKJEPC-RKVPGOIHSA-N [(1R,2S,4R)-4-[[5-[4-[(3-chloro-2-fluorophenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC1=C(C(=CC=C1)Cl)F)O)(=O)=O FIONUXZGEKJEPC-RKVPGOIHSA-N 0.000 claims description 2
DZCBYXGJYDVIDX-CLCXKQKWSA-N [(1R,2S,4R)-4-[[5-[4-[(3-chloro-4-fluorophenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC1=CC(=C(C=C1)F)Cl)O)(=O)=O DZCBYXGJYDVIDX-CLCXKQKWSA-N 0.000 claims description 2
YELKFSFFYGTJTC-MDYRTPRTSA-N [(1R,2S,4R)-4-[[5-[4-[(3-chloro-N-methylanilino)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CN(C)C1=CC(=CC=C1)Cl)O)(=O)=O YELKFSFFYGTJTC-MDYRTPRTSA-N 0.000 claims description 2
KUYIHJUXNCLATR-OGWOLHLISA-N [(1R,2S,4R)-4-[[5-[4-[(3-chlorophenoxy)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)COC1=CC(=CC=C1)Cl)O)(=O)=O KUYIHJUXNCLATR-OGWOLHLISA-N 0.000 claims description 2
RWRVEOALLIOZIG-SUMDDJOVSA-N [(1R,2S,4R)-4-[[5-[4-[(3-chlorophenyl)methyl]-5-(hydroxymethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CC1=CC(=CC=C1)Cl)CO)O)(=O)=O RWRVEOALLIOZIG-SUMDDJOVSA-N 0.000 claims description 2
RKYUNAWBXFFPTG-POAQFYNOSA-N [(1R,2S,4R)-4-[[5-[4-[(3-chlorophenyl)methyl]-5-(methoxymethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CC1=CC(=CC=C1)Cl)COC)O)(=O)=O RKYUNAWBXFFPTG-POAQFYNOSA-N 0.000 claims description 2
ZJEUCXUPKVDSFI-CMCXCUNFSA-N [(1R,2S,4R)-4-[[5-[4-[(3-chlorophenyl)methyl]-5-[(2R)-oxolan-2-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CC1=CC(=CC=C1)Cl)[C@@H]1OCCC1)O)(=O)=O ZJEUCXUPKVDSFI-CMCXCUNFSA-N 0.000 claims description 2
GQTICLWVXLXMJY-QFUCXCTJSA-N [(1R,2S,4R)-4-[[5-[4-[(3-chlorophenyl)methyl]-5-[(dimethylamino)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CC1=CC(=CC=C1)Cl)CN(C)C)O)(=O)=O GQTICLWVXLXMJY-QFUCXCTJSA-N 0.000 claims description 2
FVAVFBLBMADQCZ-SUMDDJOVSA-N [(1R,2S,4R)-4-[[5-[4-[(3-chlorophenyl)methyl]-5-cyanothiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl nitrate Chemical compound C1[C@H](C[C@@H]([C@H]1CO[N+](=O)[O-])O)NC2=NC=NC=C2C(=O)C3=CC(=C(S3)C#N)CC4=CC(=CC=C4)Cl FVAVFBLBMADQCZ-SUMDDJOVSA-N 0.000 claims description 2
LKKKGQLTWJCMMZ-KYJSFNMBSA-N [(1R,2S,4R)-4-[[5-[4-[(3-chlorophenyl)methyl]-5-fluorothiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CC1=CC(=CC=C1)Cl)F)O)(=O)=O LKKKGQLTWJCMMZ-KYJSFNMBSA-N 0.000 claims description 2
XRLLACNICXPGBE-OGWOLHLISA-N [(1R,2S,4R)-4-[[5-[4-[(3-chlorophenyl)methyl]-5-methyl-1,3-thiazole-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(N=1)CC1=CC(=CC=C1)Cl)C)O)(=O)=O XRLLACNICXPGBE-OGWOLHLISA-N 0.000 claims description 2
MTKDHLHKUOHZHT-POAQFYNOSA-N [(1R,2S,4R)-4-[[5-[4-[(3-chlorophenyl)methyl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CC1=CC(=CC=C1)Cl)C)O)(=O)=O MTKDHLHKUOHZHT-POAQFYNOSA-N 0.000 claims description 2
NHIORDYEPSGBLW-SUMDDJOVSA-N [(1R,2S,4R)-4-[[5-[4-[(3-chlorophenyl)methyl]furan-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1OC=C(C=1)CC1=CC(=CC=C1)Cl)O)(=O)=O NHIORDYEPSGBLW-SUMDDJOVSA-N 0.000 claims description 2
PKHLGIWBWMPLAR-SUMDDJOVSA-N [(1R,2S,4R)-4-[[5-[4-[(3-chlorophenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound NS(=O)(=O)OC[C@H]1C[C@H](C[C@@H]1O)NC1=C(C=NC=N1)C(=O)C1=CC(CC2=CC(Cl)=CC=C2)=CS1 PKHLGIWBWMPLAR-SUMDDJOVSA-N 0.000 claims description 2
BWLRDFPKOPCILB-GGPKGHCWSA-N [(1R,2S,4R)-4-[[5-[4-[(3-cyanophenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC1=CC(=CC=C1)C#N)O)(=O)=O BWLRDFPKOPCILB-GGPKGHCWSA-N 0.000 claims description 2
BQHFQVPHOBHVMM-SJBKTWHCSA-N [(1R,2S,4R)-4-[[5-[4-[(3-ethylphenyl)methyl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CC1=CC(=CC=C1)CC)C)O)(=O)=O BQHFQVPHOBHVMM-SJBKTWHCSA-N 0.000 claims description 2
OECMFGDDJGDNDC-SBHAEUEKSA-N [(1R,2S,4R)-4-[[5-[4-[(3-ethynylphenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC1=CC(=CC=C1)C#C)O)(=O)=O OECMFGDDJGDNDC-SBHAEUEKSA-N 0.000 claims description 2
RYRHXRFUWYWRQM-SUMDDJOVSA-N [(1R,2S,4R)-4-[[5-[4-[(3-fluorophenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC1=CC(=CC=C1)F)O)(=O)=O RYRHXRFUWYWRQM-SUMDDJOVSA-N 0.000 claims description 2
QAOSFMJBBULVBX-OGWOLHLISA-N [(1R,2S,4R)-4-[[5-[4-[(4-bromo-2-cyanopyrrol-1-yl)methyl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CN1C(=CC(=C1)Br)C#N)C)O)(=O)=O QAOSFMJBBULVBX-OGWOLHLISA-N 0.000 claims description 2
JVCPEKYZGTUULH-NFAWXSAZSA-N [(1R,2S,4R)-4-[[5-[4-[(4-bromoimidazol-1-yl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CN1C=NC(=C1)Br)O)(=O)=O JVCPEKYZGTUULH-NFAWXSAZSA-N 0.000 claims description 2
SWDAOPXHKAVHCY-OGWOLHLISA-N [(1R,2S,4R)-4-[[5-[4-[(4-chlorophenoxy)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)COC1=CC=C(C=C1)Cl)O)(=O)=O SWDAOPXHKAVHCY-OGWOLHLISA-N 0.000 claims description 2
VBRQPCMQHHXYBK-SUMDDJOVSA-N [(1R,2S,4R)-4-[[5-[4-[(4-chlorophenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC1=CC=C(C=C1)Cl)O)(=O)=O VBRQPCMQHHXYBK-SUMDDJOVSA-N 0.000 claims description 2
HFBUTQMGEDUOMH-HMUFGYNFSA-N [(1R,2S,4R)-4-[[5-[4-[(4S)-2-chloro-6,7-dihydro-4H-furo[3,2-c]pyran-4-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@H]1OCCC2=C1C=C(O2)Cl)C)O)(=O)=O HFBUTQMGEDUOMH-HMUFGYNFSA-N 0.000 claims description 2
YVMNVRKUVOGRGA-JUXOCIIHSA-N [(1R,2S,4R)-4-[[5-[4-[(5-chloro-2,3-dihydroindol-1-yl)methyl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CN1CCC2=CC(=CC=C12)Cl)C)O)(=O)=O YVMNVRKUVOGRGA-JUXOCIIHSA-N 0.000 claims description 2
IBQWEQBXMOROGO-IOASZLSFSA-N [(1R,2S,4R)-4-[[5-[4-[(5-chlorofuran-2-yl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC=1OC(=CC=1)Cl)O)(=O)=O IBQWEQBXMOROGO-IOASZLSFSA-N 0.000 claims description 2
GDFMILXLOPAOFQ-XPKDYRNWSA-N [(1R,2S,4R)-4-[[5-[4-[(6-bromopyridin-2-yl)methyl]-5-chlorothiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CC1=NC(=CC=C1)Br)Cl)O)(=O)=O GDFMILXLOPAOFQ-XPKDYRNWSA-N 0.000 claims description 2
JUTUEXSNECQXLT-UNEWFSDZSA-N [(1R,2S,4R)-4-[[5-[4-[(6-bromopyridin-2-yl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC1=NC(=CC=C1)Br)O)(=O)=O JUTUEXSNECQXLT-UNEWFSDZSA-N 0.000 claims description 2
BFZLVZXQSQMJGT-BLIXFSHQSA-N [(1R,2S,4R)-4-[[5-[4-[(6-chloroindol-1-yl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CN1C=CC2=CC=C(C=C12)Cl)O)(=O)=O BFZLVZXQSQMJGT-BLIXFSHQSA-N 0.000 claims description 2
ZSUJQYSDUZSCIU-UNEWFSDZSA-N [(1R,2S,4R)-4-[[5-[4-[(6-chloropyridin-2-yl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC1=NC(=CC=C1)Cl)O)(=O)=O ZSUJQYSDUZSCIU-UNEWFSDZSA-N 0.000 claims description 2
ZWRQSXVDUWJJSO-VIZSFHNOSA-N [(1R,2S,4R)-4-[[5-[4-[(6-cyano-2,3-dihydroindol-1-yl)methyl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CN1CCC2=CC=C(C=C12)C#N)C)O)(=O)=O ZWRQSXVDUWJJSO-VIZSFHNOSA-N 0.000 claims description 2
OFZPPRAYUFDNNN-KNKQGSTJSA-N [(1R,2S,4R)-4-[[5-[4-[(6-cyanoindol-1-yl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CN1C=CC2=CC=C(C=C12)C#N)O)(=O)=O OFZPPRAYUFDNNN-KNKQGSTJSA-N 0.000 claims description 2
LEUYBCMYOKGGMF-HMUFGYNFSA-N [(1R,2S,4R)-4-[[5-[4-[(8R)-2-chloro-5,5-difluoro-6,8-dihydropyrano[3,4-b]pyridin-8-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@H]1OCC(C=2C1=NC(=CC=2)Cl)(F)F)C)O)(=O)=O LEUYBCMYOKGGMF-HMUFGYNFSA-N 0.000 claims description 2
MGCDXIHUANFHBI-XHKDOFFWSA-N [(1R,2S,4R)-4-[[5-[4-[(8S)-2-chloro-5,5-difluoro-6,8-dihydropyrano[3,4-b]pyridin-8-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C1)[C@@H]1OCC(C=2C1=NC(=CC2)Cl)(F)F)C)O)(=O)=O MGCDXIHUANFHBI-XHKDOFFWSA-N 0.000 claims description 2
QGKYPQQBUWTDAI-YMPLYOIOSA-N [(1R,2S,4R)-4-[[5-[4-[(8S)-2-chloro-6,8-dihydro-5H-pyrano[3,4-b]pyridin-8-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H]1OCCC=2C1=NC(=CC=2)Cl)C)O)(=O)=O QGKYPQQBUWTDAI-YMPLYOIOSA-N 0.000 claims description 2
PYBGUBQZSLGJII-FXMYGGSYSA-N [(1R,2S,4R)-4-[[5-[4-[(R)-(3-bromophenyl)-hydroxymethyl]-5-chlorothiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@H](O)C1=CC(=CC=C1)Br)Cl)O)(=O)=O PYBGUBQZSLGJII-FXMYGGSYSA-N 0.000 claims description 2
WPJUZILRUHDPDD-LPZXAVJZSA-N [(1R,2S,4R)-4-[[5-[4-[(R)-(3-bromophenyl)-methoxymethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@H](OC)C1=CC(=CC=C1)Br)O)(=O)=O WPJUZILRUHDPDD-LPZXAVJZSA-N 0.000 claims description 2
DOWYIWAYBWYUNF-BWZSVYRMSA-N [(1R,2S,4R)-4-[[5-[4-[(R)-(3-chlorophenyl)-(methylamino)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@H](NC)C1=CC(=CC=C1)Cl)O)(=O)=O DOWYIWAYBWYUNF-BWZSVYRMSA-N 0.000 claims description 2
PLMYHNPIXAICML-IXWMLOJYSA-N [(1R,2S,4R)-4-[[5-[4-[(R)-(3-chlorophenyl)-hydroxymethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@H](O)C1=CC(=CC=C1)Cl)O)(=O)=O PLMYHNPIXAICML-IXWMLOJYSA-N 0.000 claims description 2
UGHVATHEDRQGPP-HXFILWEYSA-N [(1R,2S,4R)-4-[[5-[4-[(R)-(6-chloropyridin-2-yl)-hydroxymethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@@H](O)C1=NC(=CC=C1)Cl)O)(=O)=O UGHVATHEDRQGPP-HXFILWEYSA-N 0.000 claims description 2
RQYBHYVLXAGXKU-GEBXKSAFSA-N [(1R,2S,4R)-4-[[5-[4-[(S)-(3-chlorophenyl)-hydroxymethyl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H](O)C1=CC(=CC=C1)Cl)C)O)(=O)=O RQYBHYVLXAGXKU-GEBXKSAFSA-N 0.000 claims description 2
PLMYHNPIXAICML-GNYRAKODSA-N [(1R,2S,4R)-4-[[5-[4-[(S)-(3-chlorophenyl)-hydroxymethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@@H](O)C1=CC(=CC=C1)Cl)O)(=O)=O PLMYHNPIXAICML-GNYRAKODSA-N 0.000 claims description 2
IDCCHNQTMWOXRG-GTUAPLQHSA-N [(1R,2S,4R)-4-[[5-[4-[(S)-(5-bromo-2-fluorophenyl)-hydroxymethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)[C@@H](O)C1=C(C=CC(=C1)Br)F)O)(=O)=O IDCCHNQTMWOXRG-GTUAPLQHSA-N 0.000 claims description 2
MBSFJWCQFLDUEF-TWILYEHCSA-N [(1R,2S,4R)-4-[[5-[4-[(S)-amino-(3-bromophenyl)methyl]-5-chlorothiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl] N-methylsulfamate Chemical compound CNS(O[C@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@H](C1=CC(=CC=C1)Br)N)Cl)O)(=O)=O MBSFJWCQFLDUEF-TWILYEHCSA-N 0.000 claims description 2
DYZDKXOZOSPTDD-ZTNFWEORSA-N [(1R,2S,4R)-4-[[5-[4-[1-(3-bromophenyl)ethenyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound NS(=O)(=O)OC[C@H]1C[C@H](C[C@@H]1O)NC1=C(C=NC=N1)C(=O)C1=CC(=CS1)C(=C)C1=CC(Br)=CC=C1 DYZDKXOZOSPTDD-ZTNFWEORSA-N 0.000 claims description 2
LGSUEQNCZUPUOK-BLIXFSHQSA-N [(1R,2S,4R)-4-[[5-[4-[1-(3-chlorophenyl)ethenyl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)C(=C)C1=CC(Cl)=CC=C1 LGSUEQNCZUPUOK-BLIXFSHQSA-N 0.000 claims description 2
DECWMDULWYABTJ-POAQFYNOSA-N [(1R,2S,4R)-4-[[5-[4-[2-(3-chlorophenyl)ethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CCC1=CC(=CC=C1)Cl)O)(=O)=O DECWMDULWYABTJ-POAQFYNOSA-N 0.000 claims description 2
UHRRNAGZFGUZLI-POAQFYNOSA-N [(1R,2S,4R)-4-[[5-[4-[2-(4-chlorophenyl)ethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CCC1=CC=C(C=C1)Cl)O)(=O)=O UHRRNAGZFGUZLI-POAQFYNOSA-N 0.000 claims description 2
LPXTVLJYWZGIHW-MDZRGWNJSA-N [(1R,2S,4R)-4-[[5-[4-[[3-(difluoromethoxy)phenyl]methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC=C(C=1)CC1=CC(=CC=C1)OC(F)F)O)(=O)=O LPXTVLJYWZGIHW-MDZRGWNJSA-N 0.000 claims description 2
RYQCWSKWELMGGB-AICUMBRKSA-N [(1R,2S,4R)-4-[[5-[4-chloro-5-[(S)-(3-chlorophenyl)-hydroxymethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)Cl)[C@@H](O)C1=CC(=CC=C1)Cl)O)(=O)=O RYQCWSKWELMGGB-AICUMBRKSA-N 0.000 claims description 2
WZCRAFZQFCFIAO-CPUCHLNUSA-N [(1R,2S,4R)-4-[[5-[5-(benzenesulfonyl)furan-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound NS(=O)(=O)OC[C@H]1C[C@H](C[C@@H]1O)NC1=C(C=NC=N1)C(=O)C1=CC=C(O1)S(=O)(=O)C1=CC=CC=C1 WZCRAFZQFCFIAO-CPUCHLNUSA-N 0.000 claims description 2
KTMQQYVVMDVGJX-MHFQSKMRSA-N [(1R,2S,4R)-4-[[5-[5-[(1S)-1-(3-chlorophenyl)-1-hydroxyethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=CC=1)[C@@](C)(O)C1=CC(=CC=C1)Cl)O)(=O)=O KTMQQYVVMDVGJX-MHFQSKMRSA-N 0.000 claims description 2
ZHYGWRCVOBRNRJ-OGWOLHLISA-N [(1R,2S,4R)-4-[[5-[5-[(3-bromophenyl)methyl]furan-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1OC(=CC=1)CC1=CC(=CC=C1)Br)O)(=O)=O ZHYGWRCVOBRNRJ-OGWOLHLISA-N 0.000 claims description 2
YXFVNSGKNHRZFG-MDYRTPRTSA-N [(1R,2S,4R)-4-[[5-[5-[(3-chlorophenyl)methyl]-3-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=CC=1C)CC1=CC(=CC=C1)Cl)O)(=O)=O YXFVNSGKNHRZFG-MDYRTPRTSA-N 0.000 claims description 2
CYPIVBBVTCJUCJ-SUMDDJOVSA-N [(1R,2S,4R)-4-[[5-[5-[(3-chlorophenyl)methyl]-4-(hydroxymethyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CO)CC1=CC(=CC=C1)Cl)O)(=O)=O CYPIVBBVTCJUCJ-SUMDDJOVSA-N 0.000 claims description 2
DHVKOHGSUUTLRI-OGWOLHLISA-N [(1R,2S,4R)-4-[[5-[5-[(3-chlorophenyl)methyl]furan-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1OC(=CC=1)CC1=CC(=CC=C1)Cl)O)(=O)=O DHVKOHGSUUTLRI-OGWOLHLISA-N 0.000 claims description 2
FJGPEIBYFVSCMP-KYJSFNMBSA-N [(1R,2S,4R)-4-[[5-[5-bromo-4-[(3-chlorophenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CC1=CC(=CC=C1)Cl)Br)O)(=O)=O FJGPEIBYFVSCMP-KYJSFNMBSA-N 0.000 claims description 2
CXCOXBJNPIBWCZ-MRRJBJDNSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-(3-chlorobenzoyl)thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)C(C1=CC(=CC=C1)Cl)=O)Cl)O)(=O)=O CXCOXBJNPIBWCZ-MRRJBJDNSA-N 0.000 claims description 2
RFIMYJOQGDUOOB-KFNAQCHYSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-(3-chlorophenyl)sulfanylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)SC1=CC(=CC=C1)Cl)Cl)O)(=O)=O RFIMYJOQGDUOOB-KFNAQCHYSA-N 0.000 claims description 2
FDCWDAAJOSNMLX-KFNAQCHYSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-(3-chlorophenyl)sulfonylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)S(=O)(=O)C1=CC(=CC=C1)Cl)Cl)O)(=O)=O FDCWDAAJOSNMLX-KFNAQCHYSA-N 0.000 claims description 2
YAWDSHKHEHIRQH-CMCRGWCASA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-[(1R)-1,2,3,4-tetrahydroisoquinolin-1-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H]1NCCC2=CC=CC=C12)Cl)O)(=O)=O YAWDSHKHEHIRQH-CMCRGWCASA-N 0.000 claims description 2
CUEYYOLYYXXSHZ-TWINXVHLSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-[(1R)-1-hydroxy-2-methylpropyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H](C(C)C)O)Cl)O)(=O)=O CUEYYOLYYXXSHZ-TWINXVHLSA-N 0.000 claims description 2
DWCNQIRCXGLDPY-GMCOAPQTSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-[(1R)-6,7-difluoro-3,4-dihydro-1H-isochromen-1-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H]1OCCC2=CC(=C(C=C12)F)F)Cl)O)(=O)=O DWCNQIRCXGLDPY-GMCOAPQTSA-N 0.000 claims description 2
HMDXRNRDVFHLCW-YQWZRLNBSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-[(2S)-2-(3-chlorophenyl)oxetan-2-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@]1(OCC1)C1=CC(=CC=C1)Cl)Cl)O)(=O)=O HMDXRNRDVFHLCW-YQWZRLNBSA-N 0.000 claims description 2
XKTWBXUBNVQZSI-KYJSFNMBSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-[(3-chlorophenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)CC1=CC(=CC=C1)Cl)Cl)O)(=O)=O XKTWBXUBNVQZSI-KYJSFNMBSA-N 0.000 claims description 2
DJFQMCPCLJTHGS-AWUHREGDSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-[(8R)-2-chloro-5,6,7,8-tetrahydro-1,7-naphthyridin-8-yl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound NS(=O)(=O)OC[C@H]1C[C@H](C[C@@H]1O)NC1=C(C=NC=N1)C(=O)C1=CC([C@H]2NCCC3=CC=C(Cl)N=C23)=C(Cl)S1 DJFQMCPCLJTHGS-AWUHREGDSA-N 0.000 claims description 2
DUZCODAUIBYPJZ-VKBSWHTMSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-[(R)-(2,5-dichlorophenyl)-hydroxymethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@H](O)C1=C(C=CC(=C1)Cl)Cl)Cl)O)(=O)=O DUZCODAUIBYPJZ-VKBSWHTMSA-N 0.000 claims description 2
PTAIIFOFJSVIKP-PVZIHDEHSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-[(R)-(3-chloro-2-fluorophenyl)-hydroxymethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@H](O)C1=C(C(=CC=C1)Cl)F)Cl)O)(=O)=O PTAIIFOFJSVIKP-PVZIHDEHSA-N 0.000 claims description 2
IFYMJHRGRCXERW-LHBCVHRWSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-[(R)-(3-chlorophenyl)-methoxymethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@H](OC)C1=CC(=CC=C1)Cl)Cl)O)(=O)=O IFYMJHRGRCXERW-LHBCVHRWSA-N 0.000 claims description 2
UVZUXZGZUSFCBC-RSLSGTJTSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-[(R)-(3-chlorophenyl)sulfinyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[S@](=O)C1=CC(=CC=C1)Cl)Cl)O)(=O)=O UVZUXZGZUSFCBC-RSLSGTJTSA-N 0.000 claims description 2
LZIPLCNHVPKVNN-VKBSWHTMSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-[(R)-(5-chloro-2-fluorophenyl)-hydroxymethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@H](O)C1=C(C=CC(=C1)Cl)F)Cl)O)(=O)=O LZIPLCNHVPKVNN-VKBSWHTMSA-N 0.000 claims description 2
AHSKXROZHQQOKM-ACVTZJDJSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-[(R)-(5-chloro-2-methoxyphenyl)-hydroxymethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@H](O)C1=C(C=CC(=C1)Cl)OC)Cl)O)(=O)=O AHSKXROZHQQOKM-ACVTZJDJSA-N 0.000 claims description 2
FCJOCKJTQMFVFK-XNWVLMOPSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-[(R)-hydroxy(phenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H](C1=CC=CC=C1)O)Cl)O)(=O)=O FCJOCKJTQMFVFK-XNWVLMOPSA-N 0.000 claims description 2
NWTBDUXJYKLQBB-VKCQTPNSSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-[(R)-hydroxy-(2-methoxyphenyl)methyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H](C1=C(C=CC=C1)OC)O)Cl)O)(=O)=O NWTBDUXJYKLQBB-VKCQTPNSSA-N 0.000 claims description 2
BBYOXNCLCQHRHN-JWUMNEAUSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-[(S)-(2-chlorophenyl)-hydroxymethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound NS(=O)(=O)OC[C@H]1C[C@H](C[C@@H]1O)NC1=C(C=NC=N1)C(=O)C1=CC([C@@H](O)C2=C(Cl)C=CC=C2)=C(Cl)S1 BBYOXNCLCQHRHN-JWUMNEAUSA-N 0.000 claims description 2
SCHCQZKKFVETHG-AICUMBRKSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-[(S)-(3-chlorophenyl)-hydroxymethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H](O)C1=CC(=CC=C1)Cl)Cl)O)(=O)=O SCHCQZKKFVETHG-AICUMBRKSA-N 0.000 claims description 2
LZIPLCNHVPKVNN-SKCMXINMSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-[(S)-(5-chloro-2-fluorophenyl)-hydroxymethyl]thiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H](O)C1=C(C=CC(=C1)Cl)F)Cl)O)(=O)=O LZIPLCNHVPKVNN-SKCMXINMSA-N 0.000 claims description 2
YBVKIBPTCVVUAF-KFNAQCHYSA-N [(1R,2S,4R)-4-[[5-[5-chloro-4-[3-(trifluoromethyl)phenyl]sulfanylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)SC1=CC(=CC=C1)C(F)(F)F)Cl)O)(=O)=O YBVKIBPTCVVUAF-KFNAQCHYSA-N 0.000 claims description 2
BWVAPYMGTURTRL-JOBXFLEFSA-N [(1S,2R,4R)-4-[[5-[4-[(1R)-7-chloro-3,4-dihydro-1H-isochromen-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-(sulfamoyloxymethyl)cyclopentyl] (2S)-2-amino-3-methylbutanoate Chemical compound CC(C)[C@H](N)C(=O)O[C@H]1C[C@@H](C[C@@H]1COS(N)(=O)=O)NC1=C(C=NC=N1)C(=O)C1=CC([C@@H]2OCCC3=CC=C(Cl)C=C23)=C(C)S1 BWVAPYMGTURTRL-JOBXFLEFSA-N 0.000 claims description 2
YEZGREPNRLHQKV-BGUZSTBHSA-N [(1S,2R,4R)-4-[[5-[4-[(1R)-7-chloro-3,4-dihydro-1H-isochromen-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-(sulfamoyloxymethyl)cyclopentyl] (2S)-2-aminopropanoate Chemical compound C[C@H](N)C(=O)O[C@H]1C[C@@H](C[C@@H]1COS(N)(=O)=O)NC1=C(C=NC=N1)C(=O)C1=CC([C@@H]2OCCC3=CC=C(Cl)C=C23)=C(C)S1 YEZGREPNRLHQKV-BGUZSTBHSA-N 0.000 claims description 2
IYZLLFKNNVQDCJ-GKYRRTSGSA-N [(1S,2R,4R)-4-[[5-[4-[(1R)-7-chloro-3,4-dihydro-1H-isochromen-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-(sulfamoyloxymethyl)cyclopentyl] (2S,3S)-2-amino-3-methylpentanoate Chemical compound N[C@H](C(=O)O[C@@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H]1OCCC2=CC=C(C=C12)Cl)C)COS(N)(=O)=O)[C@H](CC)C IYZLLFKNNVQDCJ-GKYRRTSGSA-N 0.000 claims description 2
INSMFTXOHYQJPQ-DMNYXMHZSA-N [(1S,2R,4R)-4-[[5-[4-[(1R)-7-chloro-3,4-dihydro-1H-isochromen-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-(sulfamoyloxymethyl)cyclopentyl] 2-(4-phosphonooxyphenyl)acetate Chemical compound P(=O)(O)(O)OC1=CC=C(C=C1)CC(=O)O[C@@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H]1OCCC2=CC=C(C=C12)Cl)C)COS(N)(=O)=O INSMFTXOHYQJPQ-DMNYXMHZSA-N 0.000 claims description 2
GNUQWMBXYBLHPC-FTLYEJOLSA-N [(1S,2R,4R)-4-[[5-[4-[(1R)-7-chloro-3,4-dihydro-1H-isochromen-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-(sulfamoyloxymethyl)cyclopentyl] 2-aminoacetate Chemical compound NCC(=O)O[C@@H]1[C@H](C[C@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H]1OCCC2=CC=C(C=C12)Cl)C)COS(N)(=O)=O GNUQWMBXYBLHPC-FTLYEJOLSA-N 0.000 claims description 2
DJJYECLYEHWJCB-XULWSPPVSA-N [(1S,2R,4R)-4-[[5-[4-[(1R)-7-chloro-3,4-dihydro-1H-isochromen-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-(sulfamoyloxymethyl)cyclopentyl] 3-(phosphonooxymethyl)benzoate Chemical compound P(=O)(O)(O)OCC=1C=C(C(=O)O[C@@H]2[C@H](C[C@H](C2)NC2=NC=NC=C2C(=O)C=2SC(=C(C=2)[C@@H]2OCCC3=CC=C(C=C23)Cl)C)COS(N)(=O)=O)C=CC=1 DJJYECLYEHWJCB-XULWSPPVSA-N 0.000 claims description 2
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 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
UPCMYAKQHGEZMM-HHBFSAGISA-N tert-butyl (1R)-7-chloro-1-[5-[4-[[(1R,3S,4R)-3-hydroxy-4-(sulfamoyloxymethyl)cyclopentyl]amino]pyrimidine-5-carbonyl]thiophen-3-yl]-3,4-dihydro-1H-isoquinoline-2-carboxylate Chemical compound ClC1=CC=C2CCN([C@H](C2=C1)C1=CSC(=C1)C(=O)C=1C(=NC=NC=1)N[C@H]1C[C@@H]([C@H](C1)COS(N)(=O)=O)O)C(=O)OC(C)(C)C UPCMYAKQHGEZMM-HHBFSAGISA-N 0.000 claims description 2
UPCMYAKQHGEZMM-DXYSKUAASA-N tert-butyl (1S)-7-chloro-1-[5-[4-[[(1R,3S,4R)-3-hydroxy-4-(sulfamoyloxymethyl)cyclopentyl]amino]pyrimidine-5-carbonyl]thiophen-3-yl]-3,4-dihydro-1H-isoquinoline-2-carboxylate Chemical compound ClC1=CC=C2CCN([C@@H](C2=C1)C1=CSC(=C1)C(=O)C=1C(=NC=NC=1)N[C@H]1C[C@@H]([C@H](C1)COS(N)(=O)=O)O)C(=O)OC(C)(C)C UPCMYAKQHGEZMM-DXYSKUAASA-N 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
238000000634 powder X-ray diffraction Methods 0.000 claims 5
125000001041 indolyl group Chemical group 0.000 claims 2
IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 claims 2
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
101150065749 Churc1 gene Proteins 0.000 claims 1
102100038239 Protein Churchill Human genes 0.000 claims 1
LLDFGMCXKWXLOA-GQUFLPFZSA-N [(1R,2R,3S,4R)-4-[[5-[4-[(S)-amino-(6-bromopyridin-2-yl)methyl]-5-chlorothiophene-2-carbonyl]pyrimidin-4-yl]amino]-2,3-dihydroxycyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H]([C@H]([C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H](C1=NC(=CC=C1)Br)N)Cl)O)O)(=O)=O LLDFGMCXKWXLOA-GQUFLPFZSA-N 0.000 claims 1
235000014113 dietary fatty acids Nutrition 0.000 claims 1
229940079593 drug Drugs 0.000 claims 1
229930195729 fatty acid Natural products 0.000 claims 1
239000000194 fatty acid Substances 0.000 claims 1
150000004665 fatty acids Chemical class 0.000 claims 1
239000000126 substance Substances 0.000 description 52
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
230000005588 protonation Effects 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
125000002837 carbocyclic group Chemical group 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
239000000651 prodrug Substances 0.000 description 2
229940002612 prodrug Drugs 0.000 description 2
208000024172 Cardiovascular disease Diseases 0.000 description 1
102100029469 WD repeat and HMG-box DNA-binding protein 1 Human genes 0.000 description 1
101710097421 WD repeat and HMG-box DNA-binding protein 1 Proteins 0.000 description 1
ASDLZGAVSYCXHI-NLFPWZOASA-N [(1R,2S,4R)-2-hydroxy-4-[[5-[4-[(8S)-2-methoxy-6,8-dihydro-5H-pyrano[3,4-b]pyridin-8-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]cyclopentyl]methyl sulfamate Chemical compound S(N)(OC[C@@H]1[C@H](C[C@@H](C1)NC1=NC=NC=C1C(=O)C=1SC(=C(C=1)[C@@H]1OCCC=2C1=NC(=CC=2)OC)C)O)(=O)=O ASDLZGAVSYCXHI-NLFPWZOASA-N 0.000 description 1
229910021386 carbon form Inorganic materials 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
125000003003 spiro group Chemical group 0.000 description 1

JP2017521031A 2014-07-01 2015-06-30 Ｓｕｍｏ活性化酵素の阻害薬として有用なヘテロアリール化合物 Active JP6603712B2 (ja)