SK19199A3 - Bicyclic pyrimidine derivatives and their use as anti-coagulants - Google Patents

Bicyclic pyrimidine derivatives and their use as anti-coagulants Download PDF

Info

Publication number: SK19199A3
Authority: SK; Slovakia
Prior art keywords: group; alkyl; optionally substituted; nitro; cyanophenoxy
Prior art date: 1996-08-16

Application number

SK191-99A

Other languages

English (en)

Slovak (sk)

Inventor

Michael M Morrissey

Brad Buckman

Raju Mohan

Original Assignee

Schering Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-08-16

Filing date

1997-08-14

Publication date

1999-07-12

1997-08-14 Application filed by Schering Ag filed Critical Schering Ag

1999-07-12 Publication of SK19199A3 publication Critical patent/SK19199A3/sk

Links

-1 Bicyclic pyrimidine derivatives Chemical class 0.000 title claims abstract description 483
239000003146 anticoagulant agent Substances 0.000 title abstract description 6
229940127219 anticoagulant drug Drugs 0.000 title abstract description 6
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title abstract description 6
150000001875 compounds Chemical class 0.000 claims abstract description 383
238000000034 method Methods 0.000 claims abstract description 37
201000010099 disease Diseases 0.000 claims abstract description 19
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 19
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
230000001732 thrombotic effect Effects 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims description 214
125000003710 aryl alkyl group Chemical group 0.000 claims description 89
229910052736 halogen Inorganic materials 0.000 claims description 88
150000002367 halogens Chemical class 0.000 claims description 88
125000003118 aryl group Chemical group 0.000 claims description 78
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 71
125000001188 haloalkyl group Chemical group 0.000 claims description 54
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
125000004438 haloalkoxy group Chemical group 0.000 claims description 48
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
125000001424 substituent group Chemical group 0.000 claims description 46
229910052739 hydrogen Inorganic materials 0.000 claims description 41
239000001257 hydrogen Substances 0.000 claims description 41
150000003839 salts Chemical class 0.000 claims description 41
125000004663 dialkyl amino group Chemical group 0.000 claims description 40
125000003545 alkoxy group Chemical group 0.000 claims description 39
150000002431 hydrogen Chemical class 0.000 claims description 31
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 27
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 26
125000005843 halogen group Chemical group 0.000 claims description 22
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 20
125000002947 alkylene group Chemical group 0.000 claims description 16
125000000753 cycloalkyl group Chemical group 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 10
125000000623 heterocyclic group Chemical group 0.000 claims description 9
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125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 8
150000007945 N-acyl ureas Chemical group 0.000 claims description 7
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ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
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PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 claims description 5
125000002636 imidazolinyl group Chemical group 0.000 claims description 4
150000001412 amines Chemical group 0.000 claims description 3
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CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
LWYDJQMTSWRNSM-UHFFFAOYSA-N ethyl 2-(5-cyano-2-ethoxyphenoxy)-6-[3-(dimethylcarbamoyl)-5-(trifluoromethyl)phenoxy]-1-methoxy-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound C(C)OC1=C(OC2N(C(=C(C(=N2)C(=O)OCC)[N+](=O)[O-])OC2=CC(=CC(=C2)C(F)(F)F)C(=O)N(C)C)OC)C=C(C=C1)C#N LWYDJQMTSWRNSM-UHFFFAOYSA-N 0.000 description 1
RZZQMLJTNXTQHL-UHFFFAOYSA-N ethyl 2-(5-cyano-2-methoxyphenoxy)-6-[3-(dimethylcarbamoyl)-5-methylphenoxy]-1-methoxy-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound COC1=C(OC2N(C(=C(C(=N2)C(=O)OCC)[N+](=O)[O-])OC2=CC(=CC(=C2)C)C(=O)N(C)C)OC)C=C(C=C1)C#N RZZQMLJTNXTQHL-UHFFFAOYSA-N 0.000 description 1
JHFRNGSASKNSBH-UHFFFAOYSA-N ethyl 2-(5-cyano-2-methylphenoxy)-6-(3-ethoxycarbonyl-5-methylphenoxy)-1-methoxy-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CC1=C(OC2N(C(=C(C(=N2)C(=O)OCC)[N+](=O)[O-])OC2=CC(=CC(=C2)C(=O)OCC)C)OC)C=C(C=C1)C#N JHFRNGSASKNSBH-UHFFFAOYSA-N 0.000 description 1
JONCLKKMMMUSQP-UHFFFAOYSA-N ethyl 2-(5-cyano-2-phenoxyphenoxy)-6-[3-(dimethylcarbamoyl)-5-methoxyphenoxy]-1-methoxy-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound O(C1=CC=CC=C1)C1=C(OC2N(C(=C(C(=N2)C(=O)OCC)[N+](=O)[O-])OC2=CC(=CC(=C2)OC)C(=O)N(C)C)OC)C=C(C=C1)C#N JONCLKKMMMUSQP-UHFFFAOYSA-N 0.000 description 1
XFROIJVJPWXQKG-UHFFFAOYSA-N ethyl 2-(5-cyano-2-phenylmethoxycarbonylphenoxy)-6-[3-(3-ethoxy-3-oxopropyl)-5-(1,2,3,4-tetrahydropyrimidin-2-yl)phenoxy]-1-methoxy-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound C(C1=CC=CC=C1)OC(=O)C1=C(OC2N(C(=C(C(=N2)C(=O)OCC)[N+](=O)[O-])OC2=CC(=CC(=C2)CCC(=O)OCC)C2NC=CCN2)OC)C=C(C=C1)C#N XFROIJVJPWXQKG-UHFFFAOYSA-N 0.000 description 1
ORWLZNWRKVUFNP-UHFFFAOYSA-N ethyl 2-(5-cyano-2-phenylmethoxyphenoxy)-6-[3-(diethylcarbamoyl)phenoxy]-1-methoxy-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound C(C1=CC=CC=C1)OC1=C(OC2N(C(=C(C(=N2)C(=O)OCC)[N+](=O)[O-])OC2=CC(=CC=C2)C(=O)N(CC)CC)OC)C=C(C=C1)C#N ORWLZNWRKVUFNP-UHFFFAOYSA-N 0.000 description 1
GBSJGFKKCOGANL-UHFFFAOYSA-N ethyl 2-[1-amino-2-(5-cyano-2-ethoxyphenoxy)-6-[3-(dimethylcarbamoyl)-5-(trifluoromethyl)phenoxy]-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound C(C)OC1=C(OC2N(C(=C(C(=N2)CC(=O)OCC)[N+](=O)[O-])OC2=CC(=CC(=C2)C(F)(F)F)C(=O)N(C)C)N)C=C(C=C1)C#N GBSJGFKKCOGANL-UHFFFAOYSA-N 0.000 description 1
KJUBETBWWDQZHD-UHFFFAOYSA-N ethyl 2-[1-amino-2-(5-cyano-2-methoxyphenoxy)-6-[3-(dimethylcarbamoyl)-5-methylphenoxy]-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound COC1=C(OC2N(C(=C(C(=N2)CC(=O)OCC)[N+](=O)[O-])OC2=CC(=CC(=C2)C)C(=O)N(C)C)N)C=C(C=C1)C#N KJUBETBWWDQZHD-UHFFFAOYSA-N 0.000 description 1
ADWJNRYLINNIJY-UHFFFAOYSA-N ethyl 2-[1-amino-2-(5-cyano-2-nitrophenoxy)-6-[3-[2-(dimethylamino)-2-oxoethyl]-5-(1H-imidazol-2-yl)phenoxy]-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound [N+](=O)([O-])C1=C(OC2N(C(=C(C(=N2)CC(=O)OCC)[N+](=O)[O-])OC2=CC(=CC(=C2)CC(=O)N(C)C)C=2NC=CN=2)N)C=C(C=C1)C#N ADWJNRYLINNIJY-UHFFFAOYSA-N 0.000 description 1
CTYPENHXPRFZFD-UHFFFAOYSA-N ethyl 2-[1-amino-2-(5-cyano-2-phenoxyphenoxy)-6-[3-(dimethylcarbamoyl)-5-methoxyphenoxy]-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound O(C1=CC=CC=C1)C1=C(OC2N(C(=C(C(=N2)CC(=O)OCC)[N+](=O)[O-])OC2=CC(=CC(=C2)OC)C(=O)N(C)C)N)C=C(C=C1)C#N CTYPENHXPRFZFD-UHFFFAOYSA-N 0.000 description 1
XDHZZEZYPKAENO-UHFFFAOYSA-N ethyl 2-[1-amino-2-(5-cyano-2-phenylmethoxyphenoxy)-6-[3-(diethylcarbamoyl)phenoxy]-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound C(C1=CC=CC=C1)OC1=C(OC2N(C(=C(C(=N2)CC(=O)OCC)[N+](=O)[O-])OC2=CC(=CC=C2)C(=O)N(CC)CC)N)C=C(C=C1)C#N XDHZZEZYPKAENO-UHFFFAOYSA-N 0.000 description 1
KOTAOLBHIMTNST-UHFFFAOYSA-N ethyl 2-[1-amino-6-(2-carbamoyl-5-cyanophenoxy)-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)C(=O)N)N KOTAOLBHIMTNST-UHFFFAOYSA-N 0.000 description 1
QJWVMMVSGQWJNG-UHFFFAOYSA-N ethyl 2-[1-amino-6-(2-chloro-5-cyanophenoxy)-2-methylsulfanyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CSC1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)Cl)N QJWVMMVSGQWJNG-UHFFFAOYSA-N 0.000 description 1
TZUFTGXRALJEIN-UHFFFAOYSA-N ethyl 2-[1-amino-6-(2-chloro-5-cyanophenoxy)-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)Cl)N TZUFTGXRALJEIN-UHFFFAOYSA-N 0.000 description 1
LNFCXAMQTHXMLQ-UHFFFAOYSA-N ethyl 2-[1-amino-6-(3-bromo-5-cyanophenoxy)-2-methylsulfanyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CSC1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C#N)Br)N LNFCXAMQTHXMLQ-UHFFFAOYSA-N 0.000 description 1
VLKQLVCWQFFFOE-UHFFFAOYSA-N ethyl 2-[1-amino-6-(3-bromo-5-cyanophenoxy)-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C#N)Br)N VLKQLVCWQFFFOE-UHFFFAOYSA-N 0.000 description 1
VBOVNNQSEOCGIE-UHFFFAOYSA-N ethyl 2-[1-amino-6-(3-carbamoyl-4-cyanophenoxy)-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=C(C=C1)C#N)C(=O)N)N VBOVNNQSEOCGIE-UHFFFAOYSA-N 0.000 description 1
JTJBVIWZMALBRH-UHFFFAOYSA-N ethyl 2-[1-amino-6-(3-cyano-5-ethoxyphenoxy)-2-methylsulfanyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CSC1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C#N)OCC)N JTJBVIWZMALBRH-UHFFFAOYSA-N 0.000 description 1
FWORAPSBKIWHOP-UHFFFAOYSA-N ethyl 2-[1-amino-6-(3-cyano-5-ethoxyphenoxy)-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C#N)OCC)N FWORAPSBKIWHOP-UHFFFAOYSA-N 0.000 description 1
QJCLWCHHCIIABG-UHFFFAOYSA-N ethyl 2-[1-amino-6-(3-cyano-5-methoxyphenoxy)-2-methylsulfanyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CSC1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C#N)OC)N QJCLWCHHCIIABG-UHFFFAOYSA-N 0.000 description 1
CVEVCXOETBBSBD-UHFFFAOYSA-N ethyl 2-[1-amino-6-(3-cyano-5-methoxyphenoxy)-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C#N)OC)N CVEVCXOETBBSBD-UHFFFAOYSA-N 0.000 description 1
ZXNGHFNILVUIFP-UHFFFAOYSA-N ethyl 2-[1-amino-6-(3-cyano-5-phenoxyphenoxy)-2-methylsulfanyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CSC1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C#N)OC1=CC=CC=C1)N ZXNGHFNILVUIFP-UHFFFAOYSA-N 0.000 description 1
MGLDULRFZWOISZ-UHFFFAOYSA-N ethyl 2-[1-amino-6-(3-cyano-5-phenoxyphenoxy)-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C#N)OC1=CC=CC=C1)N MGLDULRFZWOISZ-UHFFFAOYSA-N 0.000 description 1
BGVHBUFQWSKJGC-UHFFFAOYSA-N ethyl 2-[1-amino-6-(4-cyano-3-methylphenoxy)-2-methylsulfanyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CSC1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=C(C=C1)C#N)C)N BGVHBUFQWSKJGC-UHFFFAOYSA-N 0.000 description 1
NKILBQAQJNHUEK-UHFFFAOYSA-N ethyl 2-[1-amino-6-(4-cyano-3-methylphenoxy)-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=C(C=C1)C#N)C)N NKILBQAQJNHUEK-UHFFFAOYSA-N 0.000 description 1
NSSBTFSBNCLKAV-UHFFFAOYSA-N ethyl 2-[1-amino-6-(4-cyano-3-nitrophenoxy)-2-methylsulfanyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CSC1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=C(C=C1)C#N)[N+](=O)[O-])N NSSBTFSBNCLKAV-UHFFFAOYSA-N 0.000 description 1
VETPBSOQYBSXMS-UHFFFAOYSA-N ethyl 2-[1-amino-6-(4-cyano-3-nitrophenoxy)-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=C(C=C1)C#N)[N+](=O)[O-])N VETPBSOQYBSXMS-UHFFFAOYSA-N 0.000 description 1
CWULIZPWUKLJFV-UHFFFAOYSA-N ethyl 2-[1-amino-6-(5-cyano-2-ethoxyphenoxy)-2-methylsulfanyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CSC1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)OCC)N CWULIZPWUKLJFV-UHFFFAOYSA-N 0.000 description 1
MVXJRBWCJGPDLJ-UHFFFAOYSA-N ethyl 2-[1-amino-6-(5-cyano-2-ethoxyphenoxy)-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)OCC)N MVXJRBWCJGPDLJ-UHFFFAOYSA-N 0.000 description 1
UHZIDHHPHYHFTP-UHFFFAOYSA-N ethyl 2-[1-amino-6-(5-cyano-2-methoxyphenoxy)-2-methylsulfanyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CSC1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)OC)N UHZIDHHPHYHFTP-UHFFFAOYSA-N 0.000 description 1
VTISPCPUGIDOSR-UHFFFAOYSA-N ethyl 2-[1-amino-6-(5-cyano-2-methoxyphenoxy)-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)OC)N VTISPCPUGIDOSR-UHFFFAOYSA-N 0.000 description 1
RGXCOMLAZOEXLZ-UHFFFAOYSA-N ethyl 2-[1-amino-6-(5-cyano-2-nitrophenoxy)-2-methylsulfanyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CSC1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)[N+](=O)[O-])N RGXCOMLAZOEXLZ-UHFFFAOYSA-N 0.000 description 1
BAIMTGQATXRGAI-UHFFFAOYSA-N ethyl 2-[1-amino-6-(5-cyano-2-nitrophenoxy)-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)[N+](=O)[O-])N BAIMTGQATXRGAI-UHFFFAOYSA-N 0.000 description 1
CIOKURURUAZXLO-UHFFFAOYSA-N ethyl 2-[1-amino-6-(5-cyano-2-phenoxyphenoxy)-2-methylsulfanyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CSC1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)OC1=CC=CC=C1)N CIOKURURUAZXLO-UHFFFAOYSA-N 0.000 description 1
KROJHBHFQNPDIQ-UHFFFAOYSA-N ethyl 2-[1-amino-6-(5-cyano-2-phenoxyphenoxy)-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)OC1=CC=CC=C1)N KROJHBHFQNPDIQ-UHFFFAOYSA-N 0.000 description 1
DZJKIJPKGDQNKZ-UHFFFAOYSA-N ethyl 2-[1-amino-6-[3-(4,5-dihydro-1H-imidazol-2-yl)-5-(dimethylamino)phenoxy]-2-methylsulfanyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CSC1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)N(C)C)C=1NCCN=1)N DZJKIJPKGDQNKZ-UHFFFAOYSA-N 0.000 description 1
IRNTUMRFPRXZMP-UHFFFAOYSA-N ethyl 2-[1-amino-6-[3-(4,5-dihydro-1H-imidazol-2-yl)-5-(dimethylamino)phenoxy]-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)N(C)C)C=1NCCN=1)N IRNTUMRFPRXZMP-UHFFFAOYSA-N 0.000 description 1
RWPCWVPHOPFBTF-UHFFFAOYSA-N ethyl 2-[1-amino-6-[3-(dimethylcarbamoyl)-5-(trifluoromethyl)phenoxy]-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C(F)(F)F)C(=O)N(C)C)N RWPCWVPHOPFBTF-UHFFFAOYSA-N 0.000 description 1
YQHGFTVLVTVZOD-UHFFFAOYSA-N ethyl 2-[1-amino-6-[3-(dimethylcarbamoyl)-5-methoxyphenoxy]-2-methylsulfanyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CSC1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)OC)C(=O)N(C)C)N YQHGFTVLVTVZOD-UHFFFAOYSA-N 0.000 description 1
JUJUYINAJAUOKT-UHFFFAOYSA-N ethyl 2-[1-amino-6-[3-(dimethylcarbamoyl)-5-methoxyphenoxy]-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)OC)C(=O)N(C)C)N JUJUYINAJAUOKT-UHFFFAOYSA-N 0.000 description 1
OTMIWWGNIZIVHP-UHFFFAOYSA-N ethyl 2-[1-amino-6-[3-(dimethylcarbamoyl)-5-methylphenoxy]-2-methylsulfanyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CSC1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C)C(=O)N(C)C)N OTMIWWGNIZIVHP-UHFFFAOYSA-N 0.000 description 1
XFCIBGKDSNTLSQ-UHFFFAOYSA-N ethyl 2-[1-amino-6-[3-(dimethylcarbamoyl)-5-methylphenoxy]-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C)C(=O)N(C)C)N XFCIBGKDSNTLSQ-UHFFFAOYSA-N 0.000 description 1
ZKQSEZASSTZBJW-UHFFFAOYSA-N ethyl 2-[1-amino-6-[3-[2-(dimethylamino)-2-oxoethyl]-5-(1H-imidazol-2-yl)phenoxy]-2-methylsulfanyl-5-nitro-2H-pyrimidin-4-yl]acetate Chemical compound CSC1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)CC(=O)N(C)C)C=1NC=CN=1)N ZKQSEZASSTZBJW-UHFFFAOYSA-N 0.000 description 1
LQEYNKALJNEOOQ-UHFFFAOYSA-N ethyl 2-[6-(5-cyano-2-phenylmethoxyphenoxy)-2-methylsulfanyl-5-nitropyrimidin-4-yl]oxyacetate Chemical compound CCOC(=O)COC1=NC(SC)=NC(OC=2C(=CC=C(C=2)C#N)OCC=2C=CC=CC=2)=C1[N+]([O-])=O LQEYNKALJNEOOQ-UHFFFAOYSA-N 0.000 description 1
ZFSCDGZHJFMJKM-UHFFFAOYSA-N ethyl 2-[[2-(5-cyano-2-phenylmethoxyphenoxy)-6-[3-(dimethylcarbamoyl)phenoxy]-5-nitropyrimidin-4-yl]amino]acetate Chemical compound N=1C(OC=2C=C(C=CC=2)C(=O)N(C)C)=C([N+]([O-])=O)C(NCC(=O)OCC)=NC=1OC1=CC(C#N)=CC=C1OCC1=CC=CC=C1 ZFSCDGZHJFMJKM-UHFFFAOYSA-N 0.000 description 1
CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
JISYABDVWYARMX-UHFFFAOYSA-N ethyl 3-[3-(6-chloro-2-methylsulfanyl-5-nitropyrimidin-4-yl)oxy-5-(1,2,3,4-tetrahydropyrimidin-2-yl)phenyl]propanoate Chemical compound C=1C(C2NC=CCN2)=CC(CCC(=O)OCC)=CC=1OC1=NC(SC)=NC(Cl)=C1[N+]([O-])=O JISYABDVWYARMX-UHFFFAOYSA-N 0.000 description 1
WJOHJLHTCVNEHA-UHFFFAOYSA-N ethyl 3-[3-[[3-amino-6-(2-ethoxy-2-oxoethyl)-2-methylsulfanyl-5-nitro-2H-pyrimidin-4-yl]oxy]-5-(1,2,3,4-tetrahydropyrimidin-2-yl)phenyl]propanoate Chemical compound CSC1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)CCC(=O)OCC)C1NC=CCN1)N WJOHJLHTCVNEHA-UHFFFAOYSA-N 0.000 description 1
FVBDPCSCJNFJNN-UHFFFAOYSA-N ethyl 3-[3-[[3-amino-6-(2-ethoxy-2-oxoethyl)-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]oxy]-5-(1,2,3,4-tetrahydropyrimidin-2-yl)phenyl]propanoate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)CCC(=O)OCC)C1NC=CCN1)N FVBDPCSCJNFJNN-UHFFFAOYSA-N 0.000 description 1
DJDWCHKVNADAJF-UHFFFAOYSA-N ethyl 3-[3-pyrimidin-4-yloxy-5-(1,2,3,4-tetrahydropyrimidin-2-yl)phenyl]propanoate Chemical compound C=1C(C2NC=CCN2)=CC(CCC(=O)OCC)=CC=1OC1=CC=NC=N1 DJDWCHKVNADAJF-UHFFFAOYSA-N 0.000 description 1
GMCBLPMBKQVEKZ-UHFFFAOYSA-N ethyl 3-[[2-(5-carbamimidoyl-2-methylphenoxy)-6-oxo-5h-pyrimido[4,5-b][1,4]oxazin-4-yl]oxy]-5-methylbenzoate Chemical compound CCOC(=O)C1=CC(C)=CC(OC=2C=3NC(=O)COC=3N=C(OC=3C(=CC=C(C=3)C(N)=N)C)N=2)=C1 GMCBLPMBKQVEKZ-UHFFFAOYSA-N 0.000 description 1
HIEOTFMRECIFMB-UHFFFAOYSA-N ethyl 3-[[2-(5-carbamimidoyl-2-methylphenoxy)-6-oxo-7,8-dihydro-5h-pteridin-4-yl]oxy]-5-methylbenzoate Chemical compound CCOC(=O)C1=CC(C)=CC(OC=2C=3NC(=O)CNC=3N=C(OC=3C(=CC=C(C=3)C(N)=N)C)N=2)=C1 HIEOTFMRECIFMB-UHFFFAOYSA-N 0.000 description 1
IJYLHVHDELXAJG-UHFFFAOYSA-N ethyl 3-[[2-(5-carbamimidoyl-2-phenoxyphenoxy)-1-methyl-6-oxo-7-(4-sulfonylcyclohexa-1,5-dien-1-yl)-5,7-dihydropteridin-4-yl]oxy]-5-methylbenzoate Chemical compound O(C1=CC=CC=C1)C1=C(OC=2N(C3=NC(C(NC3=C(N=2)OC2=CC(=CC(=C2)C(=O)OCC)C)=O)C2=CCC(C=C2)=S(=O)=O)C)C=C(C=C1)C(N)=N IJYLHVHDELXAJG-UHFFFAOYSA-N 0.000 description 1
FSLAYYCSDPZGNL-UHFFFAOYSA-N ethyl 3-[[2-(5-cyano-2-methylphenoxy)-6-oxo-7,8-dihydro-5h-pteridin-4-yl]oxy]-5-methylbenzoate Chemical compound CCOC(=O)C1=CC(C)=CC(OC=2N=C(OC=3C(=CC=C(C=3)C#N)C)NC3=NCC(=O)NC3=2)=C1 FSLAYYCSDPZGNL-UHFFFAOYSA-N 0.000 description 1
ODOHZPHURXRGEP-UHFFFAOYSA-N ethyl 3-[[2-(5-cyano-2-phenoxyphenoxy)-1-methyl-6-oxo-7-(4-sulfonylcyclohexa-1,5-dien-1-yl)-5,7-dihydropteridin-4-yl]oxy]-5-methylbenzoate Chemical compound CCOC(=O)C1=CC(C)=CC(OC=2N=C(OC=3C(=CC=C(C=3)C#N)OC=3C=CC=CC=3)N(C)C3=NC(C(=O)NC3=2)C=2C=CC(CC=2)=S(=O)=O)=C1 ODOHZPHURXRGEP-UHFFFAOYSA-N 0.000 description 1
KLWMDROMXQPVFY-UHFFFAOYSA-N ethyl 3-[[3-amino-6-(2-ethoxy-2-oxoethyl)-2-methylsulfanyl-5-nitro-2H-pyrimidin-4-yl]oxy]-5-methylbenzoate Chemical compound CSC1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C(=O)OCC)C)N KLWMDROMXQPVFY-UHFFFAOYSA-N 0.000 description 1
ZEZAERZYVLAESF-UHFFFAOYSA-N ethyl 3-[[3-amino-6-(2-ethoxy-2-oxoethyl)-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]oxy]-5-methylbenzoate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C(=O)OCC)C)N ZEZAERZYVLAESF-UHFFFAOYSA-N 0.000 description 1
BKHFRPRHHNSGQF-UHFFFAOYSA-N ethyl 3-[[7-benzyl-2-(5-carbamimidoyl-2-phenoxyphenoxy)-6-oxo-5h-pyrimido[4,5-b][1,4]oxazin-4-yl]oxy]-5-methylbenzoate Chemical compound CCOC(=O)C1=CC(C)=CC(OC=2C=3NC(=O)C(CC=4C=CC=CC=4)OC=3N=C(OC=3C(=CC=C(C=3)C(N)=N)OC=3C=CC=CC=3)N=2)=C1 BKHFRPRHHNSGQF-UHFFFAOYSA-N 0.000 description 1
IDPUCLYIULTPLR-UHFFFAOYSA-N ethyl 6-(2-carbamoyl-5-cyanophenoxy)-1-methoxy-2-[3-(1-methyl-4,5-dihydroimidazol-2-yl)phenoxy]-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CN1C(=NCC1)C=1C=C(OC2N(C(=C(C(=N2)C(=O)OCC)[N+](=O)[O-])OC2=C(C=CC(=C2)C#N)C(=O)N)OC)C=CC=1 IDPUCLYIULTPLR-UHFFFAOYSA-N 0.000 description 1
SOIRIOIUATXPIV-UHFFFAOYSA-N ethyl 6-(2-carbamoyl-5-cyanophenoxy)-1-methoxy-2-methylsulfanyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CSC1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)C(=O)N)OC SOIRIOIUATXPIV-UHFFFAOYSA-N 0.000 description 1
REDIOBQATWMJCS-UHFFFAOYSA-N ethyl 6-(2-carbamoyl-5-cyanophenoxy)-1-methoxy-2-methylsulfonyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)C(=O)N)OC REDIOBQATWMJCS-UHFFFAOYSA-N 0.000 description 1
KTAIPPJQZSXLST-UHFFFAOYSA-N ethyl 6-(2-chloro-5-cyanophenoxy)-1-methoxy-2-methylsulfanyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CSC1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)Cl)OC KTAIPPJQZSXLST-UHFFFAOYSA-N 0.000 description 1
GNPLHVRMFKOQRO-UHFFFAOYSA-N ethyl 6-(2-chloro-5-cyanophenoxy)-1-methoxy-2-methylsulfonyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)Cl)OC GNPLHVRMFKOQRO-UHFFFAOYSA-N 0.000 description 1
UHDHQQMNQNHNDD-UHFFFAOYSA-N ethyl 6-(3-bromo-5-cyanophenoxy)-1-methoxy-2-methylsulfanyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CSC1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C#N)Br)OC UHDHQQMNQNHNDD-UHFFFAOYSA-N 0.000 description 1
KKEWMGSGNYHNBX-UHFFFAOYSA-N ethyl 6-(3-bromo-5-cyanophenoxy)-1-methoxy-2-methylsulfonyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C#N)Br)OC KKEWMGSGNYHNBX-UHFFFAOYSA-N 0.000 description 1
GZDJSUFTNHVOLL-UHFFFAOYSA-N ethyl 6-(3-bromo-5-cyanophenoxy)-2-[3-(dimethylcarbamoyl)phenoxy]-1-methoxy-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CN(C(=O)C=1C=C(OC2N(C(=C(C(=N2)C(=O)OCC)[N+](=O)[O-])OC2=CC(=CC(=C2)C#N)Br)OC)C=CC=1)C GZDJSUFTNHVOLL-UHFFFAOYSA-N 0.000 description 1
TXXUEAYLWQRBJK-UHFFFAOYSA-N ethyl 6-(3-carbamoyl-4-cyanophenoxy)-1-methoxy-2-[3-(1-methyl-4,5-dihydroimidazol-2-yl)phenoxy]-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CN1C(=NCC1)C=1C=C(OC2N(C(=C(C(=N2)C(=O)OCC)[N+](=O)[O-])OC2=CC(=C(C=C2)C#N)C(=O)N)OC)C=CC=1 TXXUEAYLWQRBJK-UHFFFAOYSA-N 0.000 description 1
NUFQTOJWEGAIOG-UHFFFAOYSA-N ethyl 6-(3-carbamoyl-4-cyanophenoxy)-1-methoxy-2-methylsulfanyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CSC1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=C(C=C1)C#N)C(=O)N)OC NUFQTOJWEGAIOG-UHFFFAOYSA-N 0.000 description 1
DARRJKQSKFPVGX-UHFFFAOYSA-N ethyl 6-(3-carbamoyl-4-cyanophenoxy)-1-methoxy-2-methylsulfonyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=C(C=C1)C#N)C(=O)N)OC DARRJKQSKFPVGX-UHFFFAOYSA-N 0.000 description 1
MOWWMFPJLFBZIO-UHFFFAOYSA-N ethyl 6-(3-cyano-5-ethoxyphenoxy)-1-methoxy-2-methylsulfanyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CSC1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C#N)OCC)OC MOWWMFPJLFBZIO-UHFFFAOYSA-N 0.000 description 1
SNMCMRPQSWUCOY-UHFFFAOYSA-N ethyl 6-(3-cyano-5-ethoxyphenoxy)-1-methoxy-2-methylsulfonyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C#N)OCC)OC SNMCMRPQSWUCOY-UHFFFAOYSA-N 0.000 description 1
NSKUEVUZRBZFCP-UHFFFAOYSA-N ethyl 6-(3-cyano-5-methoxyphenoxy)-1-methoxy-2-methylsulfanyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CSC1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C#N)OC)OC NSKUEVUZRBZFCP-UHFFFAOYSA-N 0.000 description 1
VORAAWOIHGWFPO-UHFFFAOYSA-N ethyl 6-(3-cyano-5-methoxyphenoxy)-1-methoxy-2-methylsulfonyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C#N)OC)OC VORAAWOIHGWFPO-UHFFFAOYSA-N 0.000 description 1
PVSRTVOPKRWBAG-UHFFFAOYSA-N ethyl 6-(3-cyano-5-phenoxyphenoxy)-1-methoxy-2-methylsulfanyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CSC1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C#N)OC1=CC=CC=C1)OC PVSRTVOPKRWBAG-UHFFFAOYSA-N 0.000 description 1
JOQOBKYZMVOULJ-UHFFFAOYSA-N ethyl 6-(3-cyano-5-phenoxyphenoxy)-1-methoxy-2-methylsulfonyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C#N)OC1=CC=CC=C1)OC JOQOBKYZMVOULJ-UHFFFAOYSA-N 0.000 description 1
GWHORYAYKYULOM-UHFFFAOYSA-N ethyl 6-(3-ethoxycarbonyl-5-methylphenoxy)-1-methoxy-2-methylsulfanyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CSC1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C(=O)OCC)C)OC GWHORYAYKYULOM-UHFFFAOYSA-N 0.000 description 1
SGLSKJDULNOWMT-UHFFFAOYSA-N ethyl 6-(4-cyano-3-methylphenoxy)-1-methoxy-2-methylsulfanyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CSC1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=C(C=C1)C#N)C)OC SGLSKJDULNOWMT-UHFFFAOYSA-N 0.000 description 1
OPOWOHOZRSSRLQ-UHFFFAOYSA-N ethyl 6-(4-cyano-3-methylphenoxy)-1-methoxy-2-methylsulfonyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=C(C=C1)C#N)C)OC OPOWOHOZRSSRLQ-UHFFFAOYSA-N 0.000 description 1
IZOFZCYFPRKGPR-UHFFFAOYSA-N ethyl 6-(4-cyano-3-methylphenoxy)-2-[3-(dimethylamino)phenoxy]-1-methoxy-5-nitro-2h-pyrimidine-4-carboxylate Chemical compound CON1C(OC=2C=C(C)C(C#N)=CC=2)=C([N+]([O-])=O)C(C(=O)OCC)=NC1OC1=CC=CC(N(C)C)=C1 IZOFZCYFPRKGPR-UHFFFAOYSA-N 0.000 description 1
VOUVOSOZNRLGCC-UHFFFAOYSA-N ethyl 6-(4-cyano-3-nitrophenoxy)-1-methoxy-2-[3-[(2-methylpropan-2-yl)oxycarbonyl]phenoxy]-5-nitro-2h-pyrimidine-4-carboxylate Chemical compound CON1C(OC=2C=C(C(C#N)=CC=2)[N+]([O-])=O)=C([N+]([O-])=O)C(C(=O)OCC)=NC1OC1=CC=CC(C(=O)OC(C)(C)C)=C1 VOUVOSOZNRLGCC-UHFFFAOYSA-N 0.000 description 1
SLKYDQTVLKHYCE-UHFFFAOYSA-N ethyl 6-(4-cyano-3-nitrophenoxy)-1-methoxy-2-methylsulfanyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CSC1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=C(C=C1)C#N)[N+](=O)[O-])OC SLKYDQTVLKHYCE-UHFFFAOYSA-N 0.000 description 1
VUYVLAZVIJCSFC-UHFFFAOYSA-N ethyl 6-(4-cyano-3-nitrophenoxy)-1-methoxy-2-methylsulfonyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=C(C=C1)C#N)[N+](=O)[O-])OC VUYVLAZVIJCSFC-UHFFFAOYSA-N 0.000 description 1
PDQSZPPXQLQVFB-UHFFFAOYSA-N ethyl 6-(5-cyano-2-ethoxyphenoxy)-1-methoxy-2-methylsulfanyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CSC1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)OCC)OC PDQSZPPXQLQVFB-UHFFFAOYSA-N 0.000 description 1
LTFNJUMWDPIZFL-UHFFFAOYSA-N ethyl 6-(5-cyano-2-ethoxyphenoxy)-1-methoxy-2-methylsulfonyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)OCC)OC LTFNJUMWDPIZFL-UHFFFAOYSA-N 0.000 description 1
NCVXPRMPUZGCJZ-UHFFFAOYSA-N ethyl 6-(5-cyano-2-methoxyphenoxy)-1-methoxy-2-methylsulfanyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CSC1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)OC)OC NCVXPRMPUZGCJZ-UHFFFAOYSA-N 0.000 description 1
KBKQGESHFMUEOX-UHFFFAOYSA-N ethyl 6-(5-cyano-2-methoxyphenoxy)-1-methoxy-2-methylsulfonyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)OC)OC KBKQGESHFMUEOX-UHFFFAOYSA-N 0.000 description 1
BZBHWULEUZNONR-UHFFFAOYSA-N ethyl 6-(5-cyano-2-methylphenoxy)-1-methoxy-2-[3-(1-methylimidazol-2-yl)phenoxy]-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CN1C(=NC=C1)C=1C=C(OC2N(C(=C(C(=N2)C(=O)OCC)[N+](=O)[O-])OC2=C(C=CC(=C2)C#N)C)OC)C=CC=1 BZBHWULEUZNONR-UHFFFAOYSA-N 0.000 description 1
IIUNDPOCOCIABZ-UHFFFAOYSA-N ethyl 6-(5-cyano-2-methylphenoxy)-2-(4-ethoxycarbonylphenoxy)-1-methoxy-5-nitro-2h-pyrimidine-4-carboxylate Chemical compound CON1C(OC=2C(=CC=C(C=2)C#N)C)=C([N+]([O-])=O)C(C(=O)OCC)=NC1OC1=CC=C(C(=O)OCC)C=C1 IIUNDPOCOCIABZ-UHFFFAOYSA-N 0.000 description 1
KBWINMMXBKYMTG-UHFFFAOYSA-N ethyl 6-(5-cyano-2-nitrophenoxy)-1-methoxy-2-methylsulfanyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CSC1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)[N+](=O)[O-])OC KBWINMMXBKYMTG-UHFFFAOYSA-N 0.000 description 1
SZGZEHQPOMEDGF-UHFFFAOYSA-N ethyl 6-(5-cyano-2-nitrophenoxy)-1-methoxy-2-methylsulfonyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)[N+](=O)[O-])OC SZGZEHQPOMEDGF-UHFFFAOYSA-N 0.000 description 1
ZXPHUXBHHGBBNP-UHFFFAOYSA-N ethyl 6-(5-cyano-2-phenoxyphenoxy)-1-methoxy-2-methylsulfanyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CSC1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)OC1=CC=CC=C1)OC ZXPHUXBHHGBBNP-UHFFFAOYSA-N 0.000 description 1
KDCIDLSDAAYQCP-UHFFFAOYSA-N ethyl 6-(5-cyano-2-phenylmethoxyphenoxy)-2-[3-(dimethylcarbamoyl)phenoxy]-1-methoxy-5-nitro-2h-pyrimidine-4-carboxylate Chemical compound CON1C(OC=2C(=CC=C(C=2)C#N)OCC=2C=CC=CC=2)=C([N+]([O-])=O)C(C(=O)OCC)=NC1OC1=CC=CC(C(=O)N(C)C)=C1 KDCIDLSDAAYQCP-UHFFFAOYSA-N 0.000 description 1
GBWMDYOVVFHLHX-UHFFFAOYSA-N ethyl 6-[3-(4,5-dihydro-1H-imidazol-2-yl)-5-(dimethylamino)phenoxy]-1-methoxy-2-methylsulfanyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CSC1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)N(C)C)C=1NCCN=1)OC GBWMDYOVVFHLHX-UHFFFAOYSA-N 0.000 description 1
LHWPRSRYUWCKEF-UHFFFAOYSA-N ethyl 6-[3-(diethylcarbamoyl)phenoxy]-1-methoxy-2-methylsulfanyl-5-nitro-2h-pyrimidine-4-carboxylate Chemical compound CCOC(=O)C1=NC(SC)N(OC)C(OC=2C=C(C=CC=2)C(=O)N(CC)CC)=C1[N+]([O-])=O LHWPRSRYUWCKEF-UHFFFAOYSA-N 0.000 description 1
ZSJVZRYJWJBMGN-UHFFFAOYSA-N ethyl 6-[3-(diethylcarbamoyl)phenoxy]-1-methoxy-2-methylsulfonyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=CC=C1)C(=O)N(CC)CC)OC ZSJVZRYJWJBMGN-UHFFFAOYSA-N 0.000 description 1
CHPWXNHEMLLTNE-UHFFFAOYSA-N ethyl 6-[3-(dimethylcarbamoyl)-5-(trifluoromethyl)phenoxy]-1-methoxy-2-methylsulfanyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CSC1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C(F)(F)F)C(=O)N(C)C)OC CHPWXNHEMLLTNE-UHFFFAOYSA-N 0.000 description 1
RNMYVHCCWSFGFL-UHFFFAOYSA-N ethyl 6-[3-(dimethylcarbamoyl)-5-(trifluoromethyl)phenoxy]-1-methoxy-2-methylsulfonyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C(F)(F)F)C(=O)N(C)C)OC RNMYVHCCWSFGFL-UHFFFAOYSA-N 0.000 description 1
LGRAHMCCENZQJH-UHFFFAOYSA-N ethyl 6-[3-(dimethylcarbamoyl)-5-methoxyphenoxy]-1-methoxy-2-methylsulfanyl-5-nitro-2h-pyrimidine-4-carboxylate Chemical compound CCOC(=O)C1=NC(SC)N(OC)C(OC=2C=C(C=C(OC)C=2)C(=O)N(C)C)=C1[N+]([O-])=O LGRAHMCCENZQJH-UHFFFAOYSA-N 0.000 description 1
BFSZVFGVERVDLM-UHFFFAOYSA-N ethyl 6-[3-(dimethylcarbamoyl)-5-methylphenoxy]-1-methoxy-2-methylsulfanyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CSC1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C)C(=O)N(C)C)OC BFSZVFGVERVDLM-UHFFFAOYSA-N 0.000 description 1
UZBTZEHXEZSQSR-UHFFFAOYSA-N ethyl 6-[3-(dimethylcarbamoyl)-5-methylphenoxy]-1-methoxy-2-methylsulfonyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=CC(=C1)C)C(=O)N(C)C)OC UZBTZEHXEZSQSR-UHFFFAOYSA-N 0.000 description 1
HIHRYJGAXMASJZ-UHFFFAOYSA-N ethyl 6-[4-cyano-3-[(2-methylpropan-2-yl)oxycarbonyl]phenoxy]-1-methoxy-2-[3-(1-methyl-4,5-dihydroimidazol-2-yl)phenoxy]-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CN1C(=NCC1)C=1C=C(OC2N(C(=C(C(=N2)C(=O)OCC)[N+](=O)[O-])OC2=CC(=C(C=C2)C#N)C(=O)OC(C)(C)C)OC)C=CC=1 HIHRYJGAXMASJZ-UHFFFAOYSA-N 0.000 description 1
TXBCJZCCZWJTGL-UHFFFAOYSA-N ethyl 6-[4-cyano-3-[(2-methylpropan-2-yl)oxycarbonyl]phenoxy]-1-methoxy-2-methylsulfanyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CSC1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=C(C=C1)C#N)C(=O)OC(C)(C)C)OC TXBCJZCCZWJTGL-UHFFFAOYSA-N 0.000 description 1
XMLAKBGRIILLRQ-UHFFFAOYSA-N ethyl 6-[4-cyano-3-[(2-methylpropan-2-yl)oxycarbonyl]phenoxy]-1-methoxy-2-methylsulfonyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=CC(=C(C=C1)C#N)C(=O)OC(C)(C)C)OC XMLAKBGRIILLRQ-UHFFFAOYSA-N 0.000 description 1
GGMDAHXWMXBCBI-UHFFFAOYSA-N ethyl 6-[5-cyano-2-[(2-methylpropan-2-yl)oxycarbonyl]phenoxy]-1-methoxy-2-methylsulfanyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CSC1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)C(=O)OC(C)(C)C)OC GGMDAHXWMXBCBI-UHFFFAOYSA-N 0.000 description 1
ZKQJEVRZWBOYBD-UHFFFAOYSA-N ethyl 6-[5-cyano-2-[(2-methylpropan-2-yl)oxycarbonyl]phenoxy]-1-methoxy-2-methylsulfonyl-5-nitro-2H-pyrimidine-4-carboxylate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)C(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)C(=O)OC(C)(C)C)OC ZKQJEVRZWBOYBD-UHFFFAOYSA-N 0.000 description 1
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125000000547 substituted alkyl group Chemical group 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
OCYLEXQKQARPEX-UHFFFAOYSA-N tert-butyl 2-(6-amino-2-methylsulfanyl-5-nitropyrimidin-4-yl)oxy-4-cyanobenzoate Chemical compound CSC1=NC(N)=C([N+]([O-])=O)C(OC=2C(=CC=C(C=2)C#N)C(=O)OC(C)(C)C)=N1 OCYLEXQKQARPEX-UHFFFAOYSA-N 0.000 description 1
CREYESKXNCWEBJ-UHFFFAOYSA-N tert-butyl 2-(6-amino-2-methylsulfonyl-5-nitropyrimidin-4-yl)oxy-4-cyanobenzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C(C#N)C=C1OC1=NC(S(C)(=O)=O)=NC(N)=C1[N+]([O-])=O CREYESKXNCWEBJ-UHFFFAOYSA-N 0.000 description 1
PUNXECKNORJTGX-UHFFFAOYSA-N tert-butyl 2-(6-chloro-2-methylsulfanyl-5-nitropyrimidin-4-yl)oxy-4-cyanobenzoate Chemical compound CSC1=NC(Cl)=C([N+]([O-])=O)C(OC=2C(=CC=C(C=2)C#N)C(=O)OC(C)(C)C)=N1 PUNXECKNORJTGX-UHFFFAOYSA-N 0.000 description 1
FBSHHCWWRMETPG-UHFFFAOYSA-N tert-butyl 2-[[3-amino-6-(2-ethoxy-2-oxoethyl)-2-methylsulfanyl-5-nitro-2H-pyrimidin-4-yl]oxy]-4-cyanobenzoate Chemical compound CSC1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)C(=O)OC(C)(C)C)N FBSHHCWWRMETPG-UHFFFAOYSA-N 0.000 description 1
ZXQIYMUZPQYITB-UHFFFAOYSA-N tert-butyl 2-[[3-amino-6-(2-ethoxy-2-oxoethyl)-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]oxy]-4-cyanobenzoate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=C(C=CC(=C1)C#N)C(=O)OC(C)(C)C)N ZXQIYMUZPQYITB-UHFFFAOYSA-N 0.000 description 1
ZVSVCVJPZZSBGN-UHFFFAOYSA-N tert-butyl 2-carbamimidoyl-5-[[2-[3-(1-methyl-4,5-dihydroimidazol-2-yl)phenoxy]-6-oxo-5h-pyrimido[4,5-b][1,4]oxazin-4-yl]oxy]benzoate Chemical compound CN1CCN=C1C1=CC=CC(OC=2N=C3OCC(=O)NC3=C(OC=3C=C(C(C(N)=N)=CC=3)C(=O)OC(C)(C)C)N=2)=C1 ZVSVCVJPZZSBGN-UHFFFAOYSA-N 0.000 description 1
DIJWONFLXQFWEU-UHFFFAOYSA-N tert-butyl 2-carbamimidoyl-5-[[2-[3-(diaminomethylideneamino)phenoxy]-6-oxo-7,8-dihydro-5h-pteridin-4-yl]oxy]benzoate Chemical compound C1=C(C(N)=N)C(C(=O)OC(C)(C)C)=CC(OC=2N=C(OC=3C=C(NC(N)=N)C=CC=3)NC3=NCC(=O)NC3=2)=C1 DIJWONFLXQFWEU-UHFFFAOYSA-N 0.000 description 1
IVTAFSAFHXSULY-UHFFFAOYSA-N tert-butyl 2-carbamimidoyl-5-[[2-[3-(diaminomethylideneamino)phenoxy]-7-(1-hydroxyethyl)-6-oxo-7,8-dihydro-5h-pteridin-4-yl]oxy]benzoate Chemical compound N=1C(OC=2C=C(C(C(N)=N)=CC=2)C(=O)OC(C)(C)C)=C2NC(=O)C(C(O)C)N=C2NC=1OC1=CC=CC(NC(N)=N)=C1 IVTAFSAFHXSULY-UHFFFAOYSA-N 0.000 description 1
YENDEEIDYVKCQH-UHFFFAOYSA-N tert-butyl 2-cyano-5-[[2-[3-(1-methyl-4,5-dihydroimidazol-2-yl)phenoxy]-6-oxo-5h-pyrimido[4,5-b][1,4]oxazin-4-yl]oxy]benzoate Chemical compound CN1CCN=C1C1=CC=CC(OC=2N=C3OCC(=O)NC3=C(OC=3C=C(C(C#N)=CC=3)C(=O)OC(C)(C)C)N=2)=C1 YENDEEIDYVKCQH-UHFFFAOYSA-N 0.000 description 1
FKWRMKGKFKWDGT-UHFFFAOYSA-N tert-butyl 2-cyano-5-[[2-[3-(diaminomethylideneamino)phenoxy]-6-oxo-7,8-dihydro-5h-pteridin-4-yl]oxy]benzoate Chemical compound C1=C(C#N)C(C(=O)OC(C)(C)C)=CC(OC=2C=3NC(=O)CNC=3N=C(OC=3C=C(C=CC=3)N=C(N)N)N=2)=C1 FKWRMKGKFKWDGT-UHFFFAOYSA-N 0.000 description 1
NZLCGNUVFSFYMR-UHFFFAOYSA-N tert-butyl 2-cyano-5-[[2-[3-(diaminomethylideneamino)phenoxy]-7-(1-hydroxyethyl)-6-oxo-7,8-dihydro-5h-pteridin-4-yl]oxy]benzoate Chemical compound N=1C(OC=2C=C(C(C#N)=CC=2)C(=O)OC(C)(C)C)=C2NC(=O)C(C(O)C)NC2=NC=1OC1=CC=CC(N=C(N)N)=C1 NZLCGNUVFSFYMR-UHFFFAOYSA-N 0.000 description 1
DGYICROZCWXWQC-UHFFFAOYSA-N tert-butyl 3-[[4-(3-amino-4-carbamimidoylphenoxy)-6-oxo-7,8-dihydro-5h-pteridin-2-yl]oxy]benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=CC(OC=2NC3=NCC(=O)NC3=C(OC=3C=C(N)C(C(N)=N)=CC=3)N=2)=C1 DGYICROZCWXWQC-UHFFFAOYSA-N 0.000 description 1
VJRYYKRHJLBWPG-UHFFFAOYSA-N tert-butyl 4-carbamimidoyl-2-[[2-[3-(diaminomethylideneamino)phenoxy]-6-oxo-7,8-dihydro-5h-pteridin-4-yl]oxy]benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C(C(N)=N)C=C1OC(N=C(OC=1C=C(NC(N)=N)C=CC=1)N1)=C2C1=NCC(=O)N2 VJRYYKRHJLBWPG-UHFFFAOYSA-N 0.000 description 1
YKQCXAZKXNNDRO-UHFFFAOYSA-N tert-butyl 4-carbamimidoyl-2-[[2-[3-(diaminomethylideneamino)phenoxy]-7-(hydroxymethyl)-6-oxo-7,8-dihydro-5h-pteridin-4-yl]oxy]benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C(C(N)=N)C=C1OC1=NC(OC=2C=C(C=CC=2)N=C(N)N)=NC2=C1NC(=O)C(CO)N2 YKQCXAZKXNNDRO-UHFFFAOYSA-N 0.000 description 1
SACURHHMLKNQOB-UHFFFAOYSA-N tert-butyl 4-cyano-2-[[2-[3-(diaminomethylideneamino)phenoxy]-6-oxo-7,8-dihydro-5h-pteridin-4-yl]oxy]benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C(C#N)C=C1OC1=NC(OC=2C=C(C=CC=2)N=C(N)N)=NC2=C1NC(=O)CN2 SACURHHMLKNQOB-UHFFFAOYSA-N 0.000 description 1
NHRXGSCLAPOIHN-UHFFFAOYSA-N tert-butyl 4-cyano-2-[[2-[3-(diaminomethylideneamino)phenoxy]-7-(hydroxymethyl)-6-oxo-7,8-dihydro-5h-pteridin-4-yl]oxy]benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=C(C#N)C=C1OC1=NC(OC=2C=C(C=CC=2)N=C(N)N)=NC2=C1NC(=O)C(CO)N2 NHRXGSCLAPOIHN-UHFFFAOYSA-N 0.000 description 1
LCWQYNFIFBNXKX-UHFFFAOYSA-N tert-butyl 5-(6-amino-2-methylsulfanyl-5-nitropyrimidin-4-yl)oxy-2-cyanobenzoate Chemical compound CSC1=NC(N)=C([N+]([O-])=O)C(OC=2C=C(C(C#N)=CC=2)C(=O)OC(C)(C)C)=N1 LCWQYNFIFBNXKX-UHFFFAOYSA-N 0.000 description 1
KPNCIVLNMWPCMM-UHFFFAOYSA-N tert-butyl 5-[6-amino-2-[3-(diaminomethylideneamino)phenoxy]-5-nitropyrimidin-4-yl]oxy-2-cyanobenzoate Chemical compound C1=C(C#N)C(C(=O)OC(C)(C)C)=CC(OC=2C(=C(N)N=C(OC=3C=C(NC(N)=N)C=CC=3)N=2)[N+]([O-])=O)=C1 KPNCIVLNMWPCMM-UHFFFAOYSA-N 0.000 description 1
OYUJYLQDVOCLCO-UHFFFAOYSA-N tert-butyl 5-[[3-amino-6-(2-ethoxy-2-oxoethyl)-2-methylsulfanyl-5-nitro-2H-pyrimidin-4-yl]oxy]-2-cyanobenzoate Chemical compound CSC1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=C(C=C1)C#N)C(=O)OC(C)(C)C)N OYUJYLQDVOCLCO-UHFFFAOYSA-N 0.000 description 1
QGYORISOTRUOSV-UHFFFAOYSA-N tert-butyl 5-[[3-amino-6-(2-ethoxy-2-oxoethyl)-2-methylsulfonyl-5-nitro-2H-pyrimidin-4-yl]oxy]-2-cyanobenzoate Chemical compound CS(=O)(=O)C1N(C(=C(C(=N1)CC(=O)OCC)[N+](=O)[O-])OC1=CC(=C(C=C1)C#N)C(=O)OC(C)(C)C)N QGYORISOTRUOSV-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
229960004559 theobromine Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
239000003868 thrombin inhibitor Substances 0.000 description 1
230000000451 tissue damage Effects 0.000 description 1
231100000827 tissue damage Toxicity 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
201000010875 transient cerebral ischemia Diseases 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
229940117013 triethanolamine oleate Drugs 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
108010036927 trypsin-like serine protease Proteins 0.000 description 1
230000002792 vascular Effects 0.000 description 1
230000003966 vascular damage Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/02—Heterocyclic compounds containing pteridine ring systems with an oxygen atom directly attached in position 4
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Hematology (AREA)
Diabetes (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

SK191-99A 1996-08-16 1997-08-14 Bicyclic pyrimidine derivatives and their use as anti-coagulants SK19199A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US08/699,372 US5693641A (en)	1996-08-16	1996-08-16	Bicyclic pyrimidine derivatives and their use as anti-coagulants
PCT/EP1997/004444 WO1998007723A1 (fr)	1996-08-16	1997-08-14	Derives de la pyrimidine bicyclique et leur utilisation comme anti-coagulants

Publications (1)

Publication Number	Publication Date
SK19199A3 true SK19199A3 (en)	1999-07-12

Family

ID=24809035

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK191-99A SK19199A3 (en)	1996-08-16	1997-08-14	Bicyclic pyrimidine derivatives and their use as anti-coagulants

Country Status (21)

Country	Link
US (3)	US5693641A (fr)
EP (1)	EP0922045B1 (fr)
JP (1)	JP2000516241A (fr)
KR (1)	KR20000068173A (fr)
CN (1)	CN1112363C (fr)
AT (1)	ATE237617T1 (fr)
AU (1)	AU724413B2 (fr)
CA (1)	CA2261908A1 (fr)
CZ (1)	CZ297323B6 (fr)
DE (1)	DE69721008T2 (fr)
DK (1)	DK0922045T3 (fr)
ES (1)	ES2195163T3 (fr)
IL (1)	IL128062A0 (fr)
NO (1)	NO990708L (fr)
NZ (1)	NZ333774A (fr)
PL (1)	PL331634A1 (fr)
PT (1)	PT922045E (fr)
RU (1)	RU2198884C2 (fr)
SK (1)	SK19199A3 (fr)
UA (1)	UA59370C2 (fr)
WO (1)	WO1998007723A1 (fr)

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DE4213919A1 (de) *	1992-04-28	1993-11-04	Thomae Gmbh Dr K	Cyclische iminoderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
AU675981B2 (en) *	1992-12-02	1997-02-27	Bristol-Myers Squibb Company	Guanidinyl-substituted heterocyclic thrombin inhibitors
CA2151044A1 (fr) *	1992-12-15	1994-06-23	Terence K. Brunck	Nouveaux inhibiteurs pour le facteur xa
US5332822A (en) *	1992-12-24	1994-07-26	Bristol-Myers Squibb Company	Heteroaromatic and thioheteroaromatic substituted sulfonamide thrombin inhibitors
ATE181334T1 (de) *	1993-02-12	1999-07-15	Corvas Int Inc	Inhibitoren gegen thrombose
IL115420A0 (en) *	1994-09-26	1995-12-31	Zeneca Ltd	Aminoheterocyclic derivatives

1996
- 1996-08-16 US US08/699,372 patent/US5693641A/en not_active Expired - Fee Related
1997
- 1997-06-17 US US08/877,231 patent/US5846972A/en not_active Expired - Fee Related
- 1997-06-17 US US08/877,318 patent/US5846970A/en not_active Expired - Fee Related
- 1997-08-14 PT PT97937584T patent/PT922045E/pt unknown
- 1997-08-14 EP EP97937584A patent/EP0922045B1/fr not_active Expired - Lifetime
- 1997-08-14 CZ CZ0050199A patent/CZ297323B6/cs not_active IP Right Cessation
- 1997-08-14 AT AT97937584T patent/ATE237617T1/de not_active IP Right Cessation
- 1997-08-14 KR KR1019997001281A patent/KR20000068173A/ko not_active Ceased
- 1997-08-14 CA CA002261908A patent/CA2261908A1/fr not_active Abandoned
- 1997-08-14 SK SK191-99A patent/SK19199A3/sk unknown
- 1997-08-14 ES ES97937584T patent/ES2195163T3/es not_active Expired - Lifetime
- 1997-08-14 DK DK97937584T patent/DK0922045T3/da active
- 1997-08-14 IL IL12806297A patent/IL128062A0/xx unknown
- 1997-08-14 AU AU40156/97A patent/AU724413B2/en not_active Ceased
- 1997-08-14 CN CN97197218A patent/CN1112363C/zh not_active Expired - Fee Related
- 1997-08-14 NZ NZ333774A patent/NZ333774A/xx unknown
- 1997-08-14 RU RU99105117/04A patent/RU2198884C2/ru not_active IP Right Cessation
- 1997-08-14 UA UA99031392A patent/UA59370C2/uk unknown
- 1997-08-14 PL PL97331634A patent/PL331634A1/xx unknown
- 1997-08-14 DE DE69721008T patent/DE69721008T2/de not_active Expired - Fee Related
- 1997-08-14 WO PCT/EP1997/004444 patent/WO1998007723A1/fr not_active Ceased
- 1997-08-14 JP JP10510376A patent/JP2000516241A/ja not_active Ceased
1999
- 1999-02-15 NO NO990708A patent/NO990708L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
CZ297323B6 (cs)	2006-11-15
PL331634A1 (en)	1999-08-02
RU2198884C2 (ru)	2003-02-20
ES2195163T3 (es)	2003-12-01
KR20000068173A (ko)	2000-11-25
PT922045E (pt)	2003-07-31
CZ50199A3 (cs)	1999-06-16
AU4015697A (en)	1998-03-06
US5846970A (en)	1998-12-08
DE69721008T2 (de)	2003-12-24
UA59370C2 (uk)	2003-09-15
DK0922045T3 (da)	2003-06-30
HK1020058A1 (en)	2000-03-10
US5846972A (en)	1998-12-08
NO990708D0 (no)	1999-02-15
NZ333774A (en)	2000-08-25
EP0922045B1 (fr)	2003-04-16
EP0922045A1 (fr)	1999-06-16
IL128062A0 (en)	1999-11-30
DE69721008D1 (de)	2003-05-22
CN1227553A (zh)	1999-09-01
CN1112363C (zh)	2003-06-25
NO990708L (no)	1999-04-15
ATE237617T1 (de)	2003-05-15
WO1998007723A1 (fr)	1998-02-26
US5693641A (en)	1997-12-02
JP2000516241A (ja)	2000-12-05
CA2261908A1 (fr)	1998-02-26
AU724413B2 (en)	2000-09-21

Publication	Publication Date	Title
SK19199A3 (en)	1999-07-12	Bicyclic pyrimidine derivatives and their use as anti-coagulants
SK19399A3 (en)	1999-08-06	Purine derivatives and their use as anti-coagulants
AU760370B2 (en)	2003-05-15	Aryl and heterocyclyl substituted pyrimidine derivatives as anti-coagulants
SK46499A3 (en)	2000-04-10	Thio acid derived monocyclic n-heterocyclics as anticoagulants
SK29599A3 (en)	1999-08-06	Benzamidine derivatives substituted by cyclic amino acid or cyclic hydroxy acid derivatives and their use as anti-coagulants
SK283306B6 (sk)	2003-05-02	Benzamidínové deriváty substituované aminokyselinovými alebo hydroxykyselinovými derivátmi, farmaceutický prostriedok obsahujúci tieto deriváty a ich použitie