CA2991684A1

CA2991684A1 - 2-amino-1,3,4-thiadiazine and 2-amino-1,3,4-oxadiazine based antifungal agents

2-amino-1,3,4-thiadiazine and 2-amino-1,3,4-oxadiazine based antifungal agents Download PDF

Info

Publication number: CA2991684A1
Authority: CA; Canada
Prior art keywords: thiadiazin; amine; alkyl; methoxy; group
Prior art date: 2015-07-14
Legal status : Abandoned

Application number

CA2991684A

Other languages

English (en)

French (fr)

Inventor

Graham Edward Morris SIBLEY

Lars Jonas Malmstrom

Johanna Maria LARSSON

Current Assignee

F2G Ltd

Original Assignee

F2G Ltd

Priority date

2015-07-14

Filing date

2016-07-14

Publication date

2017-01-19

2016-07-14 Application filed by F2G Ltd filed Critical F2G Ltd

2017-01-19 Publication of CA2991684A1 publication Critical patent/CA2991684A1/en

Status Abandoned legal-status Critical Current

Links

229940121375 antifungal agent Drugs 0.000 title claims abstract description 40
239000003429 antifungal agent Substances 0.000 title claims abstract description 40
WNLXZSXQMYFYHG-UHFFFAOYSA-N 2h-1,3,4-thiadiazin-2-amine Chemical compound NC1SC=CN=N1 WNLXZSXQMYFYHG-UHFFFAOYSA-N 0.000 title description 2
BNXJHDGIKNKIAI-UHFFFAOYSA-N NC1OC=CN=N1 Chemical compound NC1OC=CN=N1 BNXJHDGIKNKIAI-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 189
150000003839 salts Chemical class 0.000 claims abstract description 33
SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims abstract description 4
239000000203 mixture Substances 0.000 claims description 276
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 119
125000000217 alkyl group Chemical group 0.000 claims description 106
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 94
125000002947 alkylene group Chemical group 0.000 claims description 91
-1 C2-alkynyl Chemical group 0.000 claims description 78
229910052736 halogen Inorganic materials 0.000 claims description 66
150000002367 halogens Chemical class 0.000 claims description 66
125000004450 alkenylene group Chemical group 0.000 claims description 65
125000003118 aryl group Chemical group 0.000 claims description 64
125000003545 alkoxy group Chemical group 0.000 claims description 60
125000000623 heterocyclic group Chemical group 0.000 claims description 49
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 44
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 43
125000001072 heteroaryl group Chemical group 0.000 claims description 37
125000001424 substituent group Chemical group 0.000 claims description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
238000000034 method Methods 0.000 claims description 28
208000031888 Mycoses Diseases 0.000 claims description 25
125000000753 cycloalkyl group Chemical group 0.000 claims description 24
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 22
125000004104 aryloxy group Chemical group 0.000 claims description 21
206010017533 Fungal infection Diseases 0.000 claims description 20
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 20
125000004429 atom Chemical group 0.000 claims description 19
125000004452 carbocyclyl group Chemical group 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 15
229920006395 saturated elastomer Polymers 0.000 claims description 15
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 14
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 13
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 12
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 12
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
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 11
230000002265 prevention Effects 0.000 claims description 11
125000004076 pyridyl group Chemical group 0.000 claims description 11
239000003085 diluting agent Substances 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 10
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
241000233866 Fungi Species 0.000 claims description 8
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 8
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 7
241001465754 Metazoa Species 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
239000000546 pharmaceutical excipient Substances 0.000 claims description 7
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 6
UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims description 5
241000235389 Absidia Species 0.000 claims description 5
241000228212 Aspergillus Species 0.000 claims description 5
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 5
241000223218 Fusarium Species 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
241000222120 Candida <Saccharomycetales> Species 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
SMHVDYQSQJTVHP-UHFFFAOYSA-N 2-[1-(2-amino-2H-1,3,4-thiadiazin-5-yl)ethyl]isoindole-1,3-dione Chemical compound CC(N1C(=O)C2=C(C=CC=C2)C1=O)C1=CSC(N)N=N1 SMHVDYQSQJTVHP-UHFFFAOYSA-N 0.000 claims description 3
SRTIKAOGOADWCA-UHFFFAOYSA-N 2-[2-(2-amino-2H-1,3,4-thiadiazin-5-yl)ethyl]isoindole-1,3-dione Chemical compound NC1SC=C(CCN2C(=O)C3=C(C=CC=C3)C2=O)N=N1 SRTIKAOGOADWCA-UHFFFAOYSA-N 0.000 claims description 3
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 3
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
KHKBMXLDZAETKA-UHFFFAOYSA-N 4-(2-amino-4-methyl-1,3,4-thiadiazin-5-yl)benzonitrile Chemical compound CN1N=C(N)SC=C1C1=CC=C(C=C1)C#N KHKBMXLDZAETKA-UHFFFAOYSA-N 0.000 claims description 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 3
241001337994 Cryptococcus <scale insect> Species 0.000 claims description 3
241000228402 Histoplasma Species 0.000 claims description 3
241000233870 Pneumocystis Species 0.000 claims description 3
241000235527 Rhizopus Species 0.000 claims description 3
241000132889 Scedosporium Species 0.000 claims description 3
241001279361 Stachybotrys Species 0.000 claims description 3
241000223238 Trichophyton Species 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 3
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 claims description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
201000000317 pneumocystosis Diseases 0.000 claims description 3
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
ZNTYLQQGXLCPRL-UHFFFAOYSA-N 2-[4-(2-amino-6H-1,3,4-thiadiazin-5-yl)butoxymethyl]benzonitrile Chemical compound NC1=NN=C(CCCCOCC2=C(C=CC=C2)C#N)CS1 ZNTYLQQGXLCPRL-UHFFFAOYSA-N 0.000 claims description 2
VESOWHQHDOWHJG-UHFFFAOYSA-N 3-[4-(2-amino-6H-1,3,4-thiadiazin-5-yl)butoxymethyl]benzonitrile Chemical compound NC1=NN=C(CCCCOCC2=CC=CC(=C2)C#N)CS1 VESOWHQHDOWHJG-UHFFFAOYSA-N 0.000 claims description 2
RMHFUISZNAHPMP-UHFFFAOYSA-N 4-[4-(2-amino-6H-1,3,4-thiadiazin-5-yl)butoxymethyl]benzonitrile Chemical compound NC=1SCC(=NN=1)CCCCOCC1=CC=C(C#N)C=C1 RMHFUISZNAHPMP-UHFFFAOYSA-N 0.000 claims description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims description 2
KOQAGGFKUMVQIJ-UHFFFAOYSA-N ethyl 3-[3-[4-(2-amino-6H-1,3,4-thiadiazin-5-yl)butoxymethyl]phenyl]propanoate Chemical compound NC=1SCC(=NN=1)CCCCOCC=1C=C(C=CC=1)CCC(=O)OCC KOQAGGFKUMVQIJ-UHFFFAOYSA-N 0.000 claims description 2
BEBPGRTVIULNPK-UHFFFAOYSA-N ethyl 4-(2-amino-4-methyl-1,3,4-thiadiazin-5-yl)benzoate Chemical compound CCOC(=O)C1=CC=C(C=C1)C1=CSC(N)=NN1C BEBPGRTVIULNPK-UHFFFAOYSA-N 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 13
125000006832 (C1-C10) alkylene group Chemical group 0.000 claims 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
229910052760 oxygen Inorganic materials 0.000 claims 2
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
RDDDDVHPCSKUEW-UHFFFAOYSA-N 4-(5-methoxypentyl)-5-methyl-1,3,4-thiadiazin-2-amine Chemical compound COCCCCCN1N=C(N)SC=C1C RDDDDVHPCSKUEW-UHFFFAOYSA-N 0.000 claims 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
AZDTVKWRKDFWNZ-UHFFFAOYSA-N 4-methyl-5-(4-methylphenyl)-1,3,4-thiadiazin-2-amine Chemical compound CN1N=C(N)SC=C1C1=CC=C(C)C=C1 AZDTVKWRKDFWNZ-UHFFFAOYSA-N 0.000 claims 1
AHNSLYZSAYRVJH-UHFFFAOYSA-N 5-(3-methylpentan-3-yl)-6h-1,3,4-thiadiazin-2-amine Chemical compound CCC(C)(CC)C1=NN=C(N)SC1 AHNSLYZSAYRVJH-UHFFFAOYSA-N 0.000 claims 1
OLORLYWWPNUIEU-UHFFFAOYSA-N 5-(4-butoxyphenyl)-4-methyl-1,3,4-thiadiazin-2-amine Chemical compound CCCCOC1=CC=C(C=C1)C1=CSC(N)=NN1C OLORLYWWPNUIEU-UHFFFAOYSA-N 0.000 claims 1
ULEIGFFKUPXHHO-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-methyl-1,3,4-thiadiazin-2-amine Chemical compound CN1N=C(N)SC=C1C1=CC=C(Cl)C=C1 ULEIGFFKUPXHHO-UHFFFAOYSA-N 0.000 claims 1
RQCSJLZQNZUJRX-UHFFFAOYSA-N 5-(4-methoxyphenyl)-4-methyl-1,3,4-thiadiazin-2-amine Chemical compound COC1=CC=C(C=C1)C1=CSC(N)=NN1C RQCSJLZQNZUJRX-UHFFFAOYSA-N 0.000 claims 1
ZVVPYFWHMOBQGC-UHFFFAOYSA-N 5-[(3-nitrophenyl)methyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound NC1=NN=C(CC2=CC(=CC=C2)[N+]([O-])=O)CS1 ZVVPYFWHMOBQGC-UHFFFAOYSA-N 0.000 claims 1
QACFCIXTKDIKNK-UHFFFAOYSA-N 5-[4-(1,3-benzothiazol-2-ylmethoxy)butyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound S1C(=NC2=C1C=CC=C2)COCCCCC1=NN=C(SC1)N QACFCIXTKDIKNK-UHFFFAOYSA-N 0.000 claims 1
TWDOODYILYJIRO-UHFFFAOYSA-N 5-[4-(oxolan-2-ylmethoxy)butyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound NC1=NN=C(CCCCOCC2CCCO2)CS1 TWDOODYILYJIRO-UHFFFAOYSA-N 0.000 claims 1
NDTKGCABXFFFMQ-UHFFFAOYSA-N 5-[4-[(2,3,4-trifluorophenyl)methoxy]butyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound NC1=NN=C(CCCCOCC2=C(F)C(F)=C(F)C=C2)CS1 NDTKGCABXFFFMQ-UHFFFAOYSA-N 0.000 claims 1
BVSDOCDJGVKDKQ-UHFFFAOYSA-N 5-[4-[(2,3-difluorophenyl)methoxy]butyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound FC1=C(C=CC=C1F)COCCCCC1=NN=C(SC1)N BVSDOCDJGVKDKQ-UHFFFAOYSA-N 0.000 claims 1
SSWCRBXOEGFOJO-UHFFFAOYSA-N 5-[4-[(2,4,6-trifluorophenyl)methoxy]butyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound NC1=NN=C(CCCCOCC2=C(F)C=C(F)C=C2F)CS1 SSWCRBXOEGFOJO-UHFFFAOYSA-N 0.000 claims 1
CHMFMMLDISMBAI-UHFFFAOYSA-N 5-[4-[(2,4-dimethylphenyl)methoxy]butyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound CC1=C(C=CC(=C1)C)COCCCCC1=NN=C(SC1)N CHMFMMLDISMBAI-UHFFFAOYSA-N 0.000 claims 1
VZPWQUCMERBBRA-UHFFFAOYSA-N 5-[4-[(2,6-difluoro-4-methoxyphenyl)methoxy]butyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound COC1=CC(F)=C(COCCCCC2=NN=C(N)SC2)C(F)=C1 VZPWQUCMERBBRA-UHFFFAOYSA-N 0.000 claims 1
ZXBIMIPPIQCYKI-UHFFFAOYSA-N 5-[4-[(2,6-difluorophenyl)methoxy]butyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound FC1=C(C(=CC=C1)F)COCCCCC1=NN=C(SC1)N ZXBIMIPPIQCYKI-UHFFFAOYSA-N 0.000 claims 1
DURWYCVRCTXBQP-UHFFFAOYSA-N 5-[4-[(2-bromophenyl)methoxy]butyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound NC1=NN=C(CCCCOCC2=C(Br)C=CC=C2)CS1 DURWYCVRCTXBQP-UHFFFAOYSA-N 0.000 claims 1
AAULMUIGLZVFOL-UHFFFAOYSA-N 5-[4-[(2-chlorophenyl)methoxy]butyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound ClC1=C(C=CC=C1)COCCCCC1=NN=C(SC1)N AAULMUIGLZVFOL-UHFFFAOYSA-N 0.000 claims 1
ZYUTXJRWMJYHPC-UHFFFAOYSA-N 5-[4-[(2-methylcyclopropyl)methoxy]butyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound CC1C(C1)COCCCCC1=NN=C(SC1)N ZYUTXJRWMJYHPC-UHFFFAOYSA-N 0.000 claims 1
PTJPLJWXRBTOJE-UHFFFAOYSA-N 5-[4-[(2-nitrophenyl)methoxy]butyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)COCCCCC1=NN=C(SC1)N PTJPLJWXRBTOJE-UHFFFAOYSA-N 0.000 claims 1
RMCAXRQFPBRSAP-UHFFFAOYSA-N 5-[4-[(3-bromo-5-fluorophenyl)methoxy]butyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound NC1=NN=C(CCCCOCC2=CC(Br)=CC(F)=C2)CS1 RMCAXRQFPBRSAP-UHFFFAOYSA-N 0.000 claims 1
USICDGIKQZCOID-UHFFFAOYSA-N 5-[4-[(3-ethenylphenyl)methoxy]butyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound C(=C)C=1C=C(C=CC=1)COCCCCC1=NN=C(SC1)N USICDGIKQZCOID-UHFFFAOYSA-N 0.000 claims 1
XRLJYTXLOXMPBR-UHFFFAOYSA-N 5-[4-[(3-prop-1-ynylphenyl)methoxy]butyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound C(#CC)C=1C=C(C=CC=1)COCCCCC1=NN=C(SC1)N XRLJYTXLOXMPBR-UHFFFAOYSA-N 0.000 claims 1
VPAVYTGYXXAKEN-UHFFFAOYSA-N 5-[4-[(4-bromo-3-fluorophenyl)methoxy]butyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound NC1=NN=C(CCCCOCC2=CC(F)=C(Br)C=C2)CS1 VPAVYTGYXXAKEN-UHFFFAOYSA-N 0.000 claims 1
XNDNVLGTWFDLHB-UHFFFAOYSA-N 5-[4-[(5-methylthiophen-2-yl)methoxy]butyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound CC1=CC=C(S1)COCCCCC1=NN=C(SC1)N XNDNVLGTWFDLHB-UHFFFAOYSA-N 0.000 claims 1
NFZSHSBTOGSASW-QHHAFSJGSA-N 5-[4-[[3-[(E)-prop-1-enyl]phenyl]methoxy]butyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound C(=C\C)/C=1C=C(C=CC=1)COCCCCC1=NN=C(SC1)N NFZSHSBTOGSASW-QHHAFSJGSA-N 0.000 claims 1
PETGQMNSUKAMKR-UHFFFAOYSA-N 5-[6-(4-bromo-2,6-difluorophenyl)hexyl]-6H-1,3,4-thiadiazin-2-amine Chemical compound BrC1=CC(=C(C(=C1)F)CCCCCCC1=NN=C(SC1)N)F PETGQMNSUKAMKR-UHFFFAOYSA-N 0.000 claims 1
NWOGLJXGTRAFKB-UHFFFAOYSA-N 5-benzyl-6H-1,3,4-thiadiazin-2-amine Chemical compound NC1=NN=C(CC2=CC=CC=C2)CS1 NWOGLJXGTRAFKB-UHFFFAOYSA-N 0.000 claims 1
JLPLBTVKLHWBFC-UHFFFAOYSA-N ClC=1C=C(C=CC=1Cl)C=1N(N=C(SC=1)N)C Chemical compound ClC=1C=C(C=CC=1Cl)C=1N(N=C(SC=1)N)C JLPLBTVKLHWBFC-UHFFFAOYSA-N 0.000 claims 1
NXMFZXBFYBTAHM-UHFFFAOYSA-N NC1=NN=C(CS1)C=CC1=CC=C(O1)[N+]([O-])=O Chemical compound NC1=NN=C(CS1)C=CC1=CC=C(O1)[N+]([O-])=O NXMFZXBFYBTAHM-UHFFFAOYSA-N 0.000 claims 1
PVZZFRPVQXOAHV-UHFFFAOYSA-N O1C(=CC2=C1C=CC=C2)C=1N(N=C(SC=1)N)C Chemical compound O1C(=CC2=C1C=CC=C2)C=1N(N=C(SC=1)N)C PVZZFRPVQXOAHV-UHFFFAOYSA-N 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
239000000243 solution Substances 0.000 description 409
238000006243 chemical reaction Methods 0.000 description 349
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 346
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238000004809 thin layer chromatography Methods 0.000 description 207
238000002360 preparation method Methods 0.000 description 200
239000000047 product Substances 0.000 description 190
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 179
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239000002904 solvent Substances 0.000 description 172
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 164
239000011541 reaction mixture Substances 0.000 description 159
239000007787 solid Substances 0.000 description 143
229940093499 ethyl acetate Drugs 0.000 description 115
235000019439 ethyl acetate Nutrition 0.000 description 115
238000004440 column chromatography Methods 0.000 description 101
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239000007788 liquid Substances 0.000 description 84
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