KR20010014369A - 유로키나제 억제제 - Google Patents
유로키나제 억제제 Download PDFInfo
- Publication number
- KR20010014369A KR20010014369A KR1019997012528A KR19997012528A KR20010014369A KR 20010014369 A KR20010014369 A KR 20010014369A KR 1019997012528 A KR1019997012528 A KR 1019997012528A KR 19997012528 A KR19997012528 A KR 19997012528A KR 20010014369 A KR20010014369 A KR 20010014369A
- Authority
- KR
- South Korea
- Prior art keywords
- salt
- trifluoroacetate
- mono
- aminoiminomethyl
- naphthalenyl
- Prior art date
Links
- 239000002797 plasminogen activator inhibitor Substances 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 413
- 238000000034 method Methods 0.000 claims abstract description 220
- 239000000203 mixture Substances 0.000 claims abstract description 76
- 108090000435 Urokinase-type plasminogen activator Proteins 0.000 claims abstract description 15
- 102000003990 Urokinase-type plasminogen activator Human genes 0.000 claims abstract description 14
- 229960005356 urokinase Drugs 0.000 claims abstract description 11
- 230000005764 inhibitory process Effects 0.000 claims abstract description 7
- 241000124008 Mammalia Species 0.000 claims abstract description 4
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 487
- -1 2-hydroxyethoxy Chemical group 0.000 claims description 305
- 125000004432 carbon atom Chemical group C* 0.000 claims description 229
- 125000000217 alkyl group Chemical group 0.000 claims description 100
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 82
- 125000002947 alkylene group Chemical group 0.000 claims description 79
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
- 125000003118 aryl group Chemical group 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 53
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 47
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 47
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
- 125000000623 heterocyclic group Chemical group 0.000 claims description 45
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 39
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 32
- HCSHUEPPBIJJCB-UHFFFAOYSA-N carbamic acid;2,2,2-trifluoroacetic acid Chemical compound NC(O)=O.OC(=O)C(F)(F)F HCSHUEPPBIJJCB-UHFFFAOYSA-N 0.000 claims description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- XCJLXFIGEMUOEE-UHFFFAOYSA-N acetamide;2,2,2-trifluoroacetic acid Chemical compound CC(N)=O.OC(=O)C(F)(F)F XCJLXFIGEMUOEE-UHFFFAOYSA-N 0.000 claims description 13
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 13
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 10
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 10
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- XTIHVCQVRXHANI-UHFFFAOYSA-N (7-methoxy-8-prop-2-enoxynaphthalen-2-yl)methylidenehydrazine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(C=NN)=CC2=C(OCC=C)C(OC)=CC=C21 XTIHVCQVRXHANI-UHFFFAOYSA-N 0.000 claims description 5
- ZLKAMNOYAQQCFP-UHFFFAOYSA-N 3-(7-methanehydrazonoyl-2-methoxynaphthalen-1-yl)oxypropan-1-ol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(C=NN)=CC2=C(OCCCO)C(OC)=CC=C21 ZLKAMNOYAQQCFP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- WTTGZGRJCNKTTD-UHFFFAOYSA-N 4-(7-methanehydrazonoyl-2-methoxynaphthalen-1-yl)oxolan-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=C2C=CC(C=NN)=CC2=C1C1COC(=O)C1 WTTGZGRJCNKTTD-UHFFFAOYSA-N 0.000 claims description 5
- 239000007983 Tris buffer Substances 0.000 claims description 5
- WSVATSVJOIPBPQ-UHFFFAOYSA-N [7-methoxy-8-(3-phenylpropoxy)naphthalen-2-yl]methylidenehydrazine;hydrochloride Chemical compound Cl.COC1=CC=C2C=CC(C=NN)=CC2=C1OCCCC1=CC=CC=C1 WSVATSVJOIPBPQ-UHFFFAOYSA-N 0.000 claims description 5
- WKVXOYXBUUHHLG-UHFFFAOYSA-N [8-(3-bromopropoxy)-7-methoxynaphthalen-2-yl]methylidenehydrazine;hydrochloride Chemical compound Cl.C1=CC(C=NN)=CC2=C(OCCCBr)C(OC)=CC=C21 WKVXOYXBUUHHLG-UHFFFAOYSA-N 0.000 claims description 5
- PAAZCQANMCYGAW-UHFFFAOYSA-N acetic acid;2,2,2-trifluoroacetic acid Chemical compound CC(O)=O.OC(=O)C(F)(F)F PAAZCQANMCYGAW-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 5
- ZTDZEZYDHIKFBR-UHFFFAOYSA-N methyl 6-methanehydrazonoyl-4-(methoxycarbonylamino)naphthalene-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C=NN)C=C2C(NC(=O)OC)=CC(C(=O)OC)=CC2=C1 ZTDZEZYDHIKFBR-UHFFFAOYSA-N 0.000 claims description 5
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
- WFQLDQZUUJUXQS-UHFFFAOYSA-N 1-(6-methanehydrazonoylnaphthalen-2-yl)-3-propan-2-ylurea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C=NN)C=CC2=CC(NC(=O)NC(C)C)=CC=C21 WFQLDQZUUJUXQS-UHFFFAOYSA-N 0.000 claims description 4
- HNAWACFBQYQKEC-UHFFFAOYSA-N 1-benzyl-3-(6-methanehydrazonoylnaphthalen-2-yl)urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC2=CC(C=NN)=CC=C2C=C1NC(=O)NCC1=CC=CC=C1 HNAWACFBQYQKEC-UHFFFAOYSA-N 0.000 claims description 4
- DSCIZZBKVVQDOS-UHFFFAOYSA-N 1-cyclohexyl-3-(6-methanehydrazonoylnaphthalen-2-yl)urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC2=CC(C=NN)=CC=C2C=C1NC(=O)NC1CCCCC1 DSCIZZBKVVQDOS-UHFFFAOYSA-N 0.000 claims description 4
- CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical class CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 claims description 4
- RZPQCZFTOKCPBO-UHFFFAOYSA-N 4-(furan-3-yl)-6-methanehydrazonoyl-n-(1h-pyrazol-5-yl)naphthalene-2-carboxamide Chemical compound C12=CC(C=NN)=CC=C2C=C(C(=O)NC=2NN=CC=2)C=C1C=1C=COC=1 RZPQCZFTOKCPBO-UHFFFAOYSA-N 0.000 claims description 4
- UQIYBAFKTUYKRK-UHFFFAOYSA-N 4-(furan-3-yl)-6-methanehydrazonoyl-n-[4-(trifluoromethyl)phenyl]naphthalene-2-carboxamide Chemical compound C12=CC(C=NN)=CC=C2C=C(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)C=C1C=1C=COC=1 UQIYBAFKTUYKRK-UHFFFAOYSA-N 0.000 claims description 4
- KMHIDPUCWONCQT-UHFFFAOYSA-N 4-(furan-3-yl)-6-methanehydrazonoyl-n-phenylnaphthalene-2-carboxamide Chemical compound C12=CC(C=NN)=CC=C2C=C(C(=O)NC=2C=CC=CC=2)C=C1C=1C=COC=1 KMHIDPUCWONCQT-UHFFFAOYSA-N 0.000 claims description 4
- KIJACPZCGISLPN-UHFFFAOYSA-N 4-(furan-3-yl)-6-methanehydrazonoyl-n-pyridin-2-ylnaphthalene-2-carboxamide Chemical compound C12=CC(C=NN)=CC=C2C=C(C(=O)NC=2N=CC=CC=2)C=C1C=1C=COC=1 KIJACPZCGISLPN-UHFFFAOYSA-N 0.000 claims description 4
- BMOMXUZUTIVJML-UHFFFAOYSA-N 4-(furan-3-yl)-6-methanehydrazonoyl-n-pyridin-3-ylnaphthalene-2-carboxamide Chemical compound C12=CC(C=NN)=CC=C2C=C(C(=O)NC=2C=NC=CC=2)C=C1C=1C=COC=1 BMOMXUZUTIVJML-UHFFFAOYSA-N 0.000 claims description 4
- UYBIQUIIJUGJQQ-UHFFFAOYSA-N 4-(furan-3-yl)-6-methanehydrazonoyl-n-pyridin-4-ylnaphthalene-2-carboxamide Chemical compound C12=CC(C=NN)=CC=C2C=C(C(=O)NC=2C=CN=CC=2)C=C1C=1C=COC=1 UYBIQUIIJUGJQQ-UHFFFAOYSA-N 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
- FAUMPMCJSGVOIQ-UHFFFAOYSA-N 5-(6-methanehydrazonoylnaphthalen-2-yl)oxypentanoic acid Chemical compound C1=C(OCCCCC(O)=O)C=CC2=CC(C=NN)=CC=C21 FAUMPMCJSGVOIQ-UHFFFAOYSA-N 0.000 claims description 4
- AOJOIBZOEOTKOK-UHFFFAOYSA-N FC(C(=O)O)(F)F.NN=CC=1C=C2C=CC(=CC2=CC=1)NC(=O)NOCC1=CC=CC=C1 Chemical compound FC(C(=O)O)(F)F.NN=CC=1C=C2C=CC(=CC2=CC=1)NC(=O)NOCC1=CC=CC=C1 AOJOIBZOEOTKOK-UHFFFAOYSA-N 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical class [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- BDDWLYOZNHREES-UHFFFAOYSA-N methyl 3-[(7-methanehydrazonoylnaphthalen-1-yl)amino]-3-oxopropanoate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(C=NN)C=C2C(NC(=O)CC(=O)OC)=CC=CC2=C1 BDDWLYOZNHREES-UHFFFAOYSA-N 0.000 claims description 4
- UHQVFNVYADXFIG-UHFFFAOYSA-N n-(7-methanehydrazonoylnaphthalen-1-yl)-1,3-benzodioxole-5-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C2OCOC2=CC(C(=O)NC2=CC=CC3=CC=C(C=C32)C=NN)=C1 UHQVFNVYADXFIG-UHFFFAOYSA-N 0.000 claims description 4
- XYOHXGZGVSBZFV-UHFFFAOYSA-N n-(7-methanehydrazonoylnaphthalen-1-yl)-1-phenylmethanesulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC(C=NN)=CC=C2C=CC=C1NS(=O)(=O)CC1=CC=CC=C1 XYOHXGZGVSBZFV-UHFFFAOYSA-N 0.000 claims description 4
- MUFGHUSILDXRLR-UHFFFAOYSA-N n-[4-(aminomethyl)phenyl]-6-methanehydrazonoyl-4-(pyrimidin-2-ylamino)naphthalene-2-carboxamide Chemical compound C1=CC(CN)=CC=C1NC(=O)C1=CC(NC=2N=CC=CN=2)=C(C=C(C=NN)C=C2)C2=C1 MUFGHUSILDXRLR-UHFFFAOYSA-N 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- UMSVPCYSAUKCAZ-UHFFFAOYSA-N propane;hydrochloride Chemical compound Cl.CCC UMSVPCYSAUKCAZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- VHHODAGHZBQVSI-UHFFFAOYSA-N (7-methanehydrazonoylnaphthalen-1-yl)urea Chemical compound C1=CC=C(NC(N)=O)C2=CC(C=NN)=CC=C21 VHHODAGHZBQVSI-UHFFFAOYSA-N 0.000 claims description 3
- HEJYQELZHYVLPR-UHFFFAOYSA-N 1-(7-methanehydrazonoylnaphthalen-1-yl)-3-methylurea Chemical compound C1=C(C=NN)C=C2C(NC(=O)NC)=CC=CC2=C1 HEJYQELZHYVLPR-UHFFFAOYSA-N 0.000 claims description 3
- QIVKNOGLWZEDDP-UHFFFAOYSA-N 2-hydroxy-n-(7-methanehydrazonoylnaphthalen-1-yl)acetamide Chemical compound C1=CC=C(NC(=O)CO)C2=CC(C=NN)=CC=C21 QIVKNOGLWZEDDP-UHFFFAOYSA-N 0.000 claims description 3
- AYQPSMIQIORBCR-UHFFFAOYSA-N 3-(6-methanehydrazonoylnaphthalen-2-yl)-1-methyl-1-phenylurea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2C=C(C=NN)C=CC2=CC=1NC(=O)N(C)C1=CC=CC=C1 AYQPSMIQIORBCR-UHFFFAOYSA-N 0.000 claims description 3
- HJTVIWJNQYUICD-UHFFFAOYSA-N 4-[[7-methanehydrazonoyl-1-(pyrimidin-2-ylamino)naphthalen-2-yl]oxymethyl]benzoic acid Chemical compound N=1C=CC=NC=1NC=1C2=CC(C=NN)=CC=C2C=CC=1OCC1=CC=C(C(O)=O)C=C1 HJTVIWJNQYUICD-UHFFFAOYSA-N 0.000 claims description 3
- QCZZIFSYYMYJGO-UHFFFAOYSA-N 6-methanehydrazonoyl-4-(1-methylsulfonylpyrazol-4-yl)-n-phenylnaphthalene-2-carboxamide Chemical compound C1=NN(S(=O)(=O)C)C=C1C1=CC(C(=O)NC=2C=CC=CC=2)=CC2=CC=C(C=NN)C=C12 QCZZIFSYYMYJGO-UHFFFAOYSA-N 0.000 claims description 3
- QEPZBBLDWGNERQ-UHFFFAOYSA-N 6-methanehydrazonoyl-4-(oxolan-3-yl)-n-phenylnaphthalene-2-carboxamide Chemical compound C12=CC(C=NN)=CC=C2C=C(C(=O)NC=2C=CC=CC=2)C=C1C1CCOC1 QEPZBBLDWGNERQ-UHFFFAOYSA-N 0.000 claims description 3
- VWNOTMQDKWOKOV-UHFFFAOYSA-N 6-methanehydrazonoyl-n-phenyl-4-(pyrimidin-2-ylamino)naphthalene-2-carboxamide Chemical compound C12=CC(C=NN)=CC=C2C=C(C(=O)NC=2C=CC=CC=2)C=C1NC1=NC=CC=N1 VWNOTMQDKWOKOV-UHFFFAOYSA-N 0.000 claims description 3
- ZORXQIRZKAIZNR-UHFFFAOYSA-N N-(7-methanehydrazonoylnaphthalen-1-yl)propanamide Chemical compound C1=C(C=NN)C=C2C(NC(=O)CC)=CC=CC2=C1 ZORXQIRZKAIZNR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 3
- LGAMMXOQEBFTJM-UHFFFAOYSA-N n-(7-methanehydrazonoylnaphthalen-1-yl)-2-methoxyacetamide Chemical compound C1=C(C=NN)C=C2C(NC(=O)COC)=CC=CC2=C1 LGAMMXOQEBFTJM-UHFFFAOYSA-N 0.000 claims description 3
- VEGPWFAUVNNGEZ-UHFFFAOYSA-N n-[4-(hydroxymethyl)phenyl]-6-methanehydrazonoyl-4-(pyrimidin-2-ylamino)naphthalene-2-carboxamide Chemical compound C12=CC(C=NN)=CC=C2C=C(C(=O)NC=2C=CC(CO)=CC=2)C=C1NC1=NC=CC=N1 VEGPWFAUVNNGEZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 2
- XPZGCMZNGLIJMH-UHFFFAOYSA-N 2-(6-methanehydrazonoylnaphthalen-2-yl)oxyacetic acid Chemical compound C1=C(OCC(O)=O)C=CC2=CC(C=NN)=CC=C21 XPZGCMZNGLIJMH-UHFFFAOYSA-N 0.000 claims description 2
- ZQEOKSZEICUDMV-UHFFFAOYSA-N 4-(5-ethylsulfanylfuran-3-yl)-6-methanehydrazonoyl-n-phenylnaphthalene-2-carboxamide Chemical compound O1C(SCC)=CC(C=2C3=CC(C=NN)=CC=C3C=C(C=2)C(=O)NC=2C=CC=CC=2)=C1 ZQEOKSZEICUDMV-UHFFFAOYSA-N 0.000 claims description 2
- NPVYQNNGPMZHJS-UHFFFAOYSA-N 4-(5-ethylsulfanyloxolan-3-yl)-6-methanehydrazonoyl-n-phenylnaphthalene-2-carboxamide Chemical compound C1OC(SCC)CC1C1=CC(C(=O)NC=2C=CC=CC=2)=CC2=CC=C(C=NN)C=C12 NPVYQNNGPMZHJS-UHFFFAOYSA-N 0.000 claims description 2
- UVRKTQYXPIILCM-UHFFFAOYSA-N 6-(n'-hydroxycarbamimidoyl)-n-phenyl-4-(pyrimidin-2-ylamino)naphthalene-2-carboxamide Chemical compound C12=CC(C(=NO)N)=CC=C2C=C(C(=O)NC=2C=CC=CC=2)C=C1NC1=NC=CC=N1 UVRKTQYXPIILCM-UHFFFAOYSA-N 0.000 claims description 2
- WAGIJTNCWWGNLK-UHFFFAOYSA-N 6-methanehydrazonoyl-4-(5-methylsulfonylfuran-3-yl)-n-phenylnaphthalene-2-carboxamide Chemical compound O1C(S(=O)(=O)C)=CC(C=2C3=CC(C=NN)=CC=C3C=C(C=2)C(=O)NC=2C=CC=CC=2)=C1 WAGIJTNCWWGNLK-UHFFFAOYSA-N 0.000 claims description 2
- PKDBUFCNUHPYET-UHFFFAOYSA-N 6-methanehydrazonoyl-4-[5-(methoxymethyl)furan-3-yl]-n-phenylnaphthalene-2-carboxamide Chemical compound O1C(COC)=CC(C=2C3=CC(C=NN)=CC=C3C=C(C=2)C(=O)NC=2C=CC=CC=2)=C1 PKDBUFCNUHPYET-UHFFFAOYSA-N 0.000 claims description 2
- KFCJHDWNLRCWAU-UHFFFAOYSA-N 6-methanehydrazonoyl-n-phenyl-4-(5-propylsulfanylfuran-3-yl)naphthalene-2-carboxamide Chemical compound O1C(SCCC)=CC(C=2C3=CC(C=NN)=CC=C3C=C(C=2)C(=O)NC=2C=CC=CC=2)=C1 KFCJHDWNLRCWAU-UHFFFAOYSA-N 0.000 claims description 2
- HIVCWELAPNFYRW-UHFFFAOYSA-N 6-methanehydrazonoyl-n-phenyl-4-(5-propylsulfonylfuran-3-yl)naphthalene-2-carboxamide Chemical compound O1C(S(=O)(=O)CCC)=CC(C=2C3=CC(C=NN)=CC=C3C=C(C=2)C(=O)NC=2C=CC=CC=2)=C1 HIVCWELAPNFYRW-UHFFFAOYSA-N 0.000 claims description 2
- AHFHTUVEHKLUNW-UHFFFAOYSA-N 6-methanehydrazonoyl-n-phenyl-4-pyrrolidin-2-ylnaphthalene-2-carboxamide Chemical compound C12=CC(C=NN)=CC=C2C=C(C(=O)NC=2C=CC=CC=2)C=C1C1CCCN1 AHFHTUVEHKLUNW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- KHKBTFBPMAIWCS-UHFFFAOYSA-N CCCCC(O)=O.OC(=O)C(F)(F)F Chemical compound CCCCC(O)=O.OC(=O)C(F)(F)F KHKBTFBPMAIWCS-UHFFFAOYSA-N 0.000 claims 1
- ICQMZIWOQSJVFD-UHFFFAOYSA-N n-[4-(aminomethyl)phenyl]-6-(n'-hydroxycarbamimidoyl)-4-(pyrimidin-2-ylamino)naphthalene-2-carboxamide Chemical compound C1=CC(CN)=CC=C1NC(=O)C1=CC(NC=2N=CC=CN=2)=C(C=C(C=C2)C(N)=NO)C2=C1 ICQMZIWOQSJVFD-UHFFFAOYSA-N 0.000 claims 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical class CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 abstract description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 380
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- XFTALRAZSCGSKN-UHFFFAOYSA-M sodium;4-ethenylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=C(C=C)C=C1 XFTALRAZSCGSKN-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
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- 238000010254 subcutaneous injection Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
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- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
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- 239000003765 sweetening agent Substances 0.000 description 1
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- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- PQEXLIRUMIRSAL-UHFFFAOYSA-N tert-butyl 4-(2-ethoxy-2-oxoethyl)piperidine-1-carboxylate Chemical compound CCOC(=O)CC1CCN(C(=O)OC(C)(C)C)CC1 PQEXLIRUMIRSAL-UHFFFAOYSA-N 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- WIVYTYZCVWHWSH-UHFFFAOYSA-N tert-butyl n-(4-aminophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(N)C=C1 WIVYTYZCVWHWSH-UHFFFAOYSA-N 0.000 description 1
- OVHQHAKJDSKUMG-UHFFFAOYSA-N tert-butyl n-[4-(aminomethyl)anilino]carbamate Chemical compound CC(C)(C)OC(=O)NNC1=CC=C(CN)C=C1 OVHQHAKJDSKUMG-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000006169 tetracyclic group Chemical group 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- 230000007838 tissue remodeling Effects 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000006168 tricyclic group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000005760 tumorsuppression Effects 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
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- A—HUMAN NECESSITIES
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/18—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to carbon atoms of six-membered aromatic rings
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- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/30—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a six-membered aromatic ring being part of a condensed ring system
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- C07C271/62—Compounds containing any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylcarbamates
- C07C271/66—Y being a hetero atom
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- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/40—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
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- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
- C07C311/13—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings the carbon skeleton containing six-membered aromatic rings
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- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
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- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/56—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
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- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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- C07D209/04—Indoles; Hydrogenated indoles
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/58—Amidines
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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KR101228385B1 (ko) * | 2004-09-21 | 2013-02-04 | 빌렉스 아게 | 페닐알라닌 유도체의 안정한 제형 |
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WO2000005214A2 (en) * | 1998-07-24 | 2000-02-03 | Pfizer Inc. | Isoquinolines as urokinase inhibitors |
US6504031B1 (en) | 1998-08-06 | 2003-01-07 | Milan Bruncko | Naphthamidine urokinase inhibitors |
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AU735144B2 (en) * | 1997-07-23 | 2001-07-05 | Yamanouchi Pharmaceutical Co., Ltd. | Novel hexahydro-1,4-diazepine derivatives or their salts |
-
1998
- 1998-07-23 ZA ZA986594A patent/ZA986594B/xx unknown
- 1998-07-24 PL PL98339429A patent/PL339429A1/xx unknown
- 1998-07-24 BR BR9811099-3A patent/BR9811099A/pt not_active Application Discontinuation
- 1998-07-24 IL IL13336898A patent/IL133368A0/xx unknown
- 1998-07-24 HU HU0100353A patent/HUP0100353A3/hu unknown
- 1998-07-24 CA CA002294300A patent/CA2294300A1/en not_active Abandoned
- 1998-07-24 EP EP98937082A patent/EP1000018A2/en not_active Withdrawn
- 1998-07-24 KR KR1019997012528A patent/KR20010014369A/ko not_active Application Discontinuation
- 1998-07-24 JP JP51012199A patent/JP2002512636A/ja active Pending
- 1998-07-24 CN CN98806826A patent/CN1265645A/zh active Pending
- 1998-07-24 SK SK1748-99A patent/SK174899A3/sk unknown
- 1998-07-24 WO PCT/US1998/015386 patent/WO1999005096A2/en not_active Application Discontinuation
- 1998-07-24 AU AU85874/98A patent/AU8587498A/en not_active Abandoned
- 1998-07-27 AR ARP980103690A patent/AR013372A1/es unknown
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1999
- 1999-12-10 BG BG103981A patent/BG103981A/bg unknown
- 1999-12-30 NO NO996578A patent/NO996578L/no not_active Application Discontinuation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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KR101228385B1 (ko) * | 2004-09-21 | 2013-02-04 | 빌렉스 아게 | 페닐알라닌 유도체의 안정한 제형 |
Also Published As
Publication number | Publication date |
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BG103981A (bg) | 2000-11-30 |
EP1000018A2 (en) | 2000-05-17 |
JP2002512636A (ja) | 2002-04-23 |
NO996578D0 (no) | 1999-12-30 |
ZA986594B (en) | 1999-01-27 |
NO996578L (no) | 2000-01-25 |
HUP0100353A2 (hu) | 2001-05-28 |
AR013372A1 (es) | 2000-12-27 |
WO1999005096A2 (en) | 1999-02-04 |
HUP0100353A3 (en) | 2001-11-28 |
PL339429A1 (en) | 2000-12-18 |
AU8587498A (en) | 1999-02-16 |
SK174899A3 (en) | 2000-06-12 |
IL133368A0 (en) | 2001-04-30 |
CN1265645A (zh) | 2000-09-06 |
CA2294300A1 (en) | 1999-02-04 |
BR9811099A (pt) | 2002-05-14 |
WO1999005096A3 (en) | 1999-06-03 |
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