SK12102002A3 - 4-oxo-1,4-dihydro-3-cinolínkarboxamidy ako antivírusové látky - Google Patents

4-oxo-1,4-dihydro-3-cinolínkarboxamidy ako antivírusové látky Download PDF

Info

Publication number: SK12102002A3
Authority: SK; Slovakia
Prior art keywords: oxo; dihydro; methyl; chlorobenzyl; cinnolinecarboxamide
Prior art date: 2000-03-21

Application number

SK1210-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Valerie A. Vaillancourt

Scott D. Larsen

Sajiv K. Nair

Original Assignee

Pharmacia & Upjohn Company

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.)

2000-03-21

Filing date

2001-03-15

Publication date

2003-03-04

2001-03-15 Application filed by Pharmacia & Upjohn Company filed Critical Pharmacia & Upjohn Company

2003-03-04 Publication of SK12102002A3 publication Critical patent/SK12102002A3/sk

Links

IJAVOENDLHVSER-UHFFFAOYSA-N 4-oxo-1h-cinnoline-3-carboxamide Chemical class C1=CC=CC2=C(O)C(C(=O)N)=NN=C21 IJAVOENDLHVSER-UHFFFAOYSA-N 0.000 title claims description 9
239000003443 antiviral agent Substances 0.000 title description 6
150000003839 salts Chemical class 0.000 claims abstract description 21
230000002265 prevention Effects 0.000 claims abstract description 4
-1 bicyclic carbocyclic radical Chemical class 0.000 claims description 289
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 205
239000000460 chlorine Substances 0.000 claims description 80
125000000623 heterocyclic group Chemical group 0.000 claims description 52
125000003118 aryl group Chemical group 0.000 claims description 47
125000001424 substituent group Chemical group 0.000 claims description 39
125000000217 alkyl group Chemical group 0.000 claims description 38
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
238000002360 preparation method Methods 0.000 claims description 34
239000000203 mixture Substances 0.000 claims description 33
238000000034 method Methods 0.000 claims description 26
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
229910052736 halogen Inorganic materials 0.000 claims description 23
150000002367 halogens Chemical class 0.000 claims description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
239000011734 sodium Substances 0.000 claims description 14
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 11
241000701024 Human betaherpesvirus 5 Species 0.000 claims description 10
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 10
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 9
229920006395 saturated elastomer Polymers 0.000 claims description 9
241000124008 Mammalia Species 0.000 claims description 8
208000036142 Viral infection Diseases 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
230000009385 viral infection Effects 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
206010019972 Herpes viral infections Diseases 0.000 claims description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
229910052744 lithium Chemical group 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
229910052708 sodium Inorganic materials 0.000 claims description 6
239000011593 sulfur Chemical group 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
241000282414 Homo sapiens Species 0.000 claims description 5
241000701044 Human gammaherpesvirus 4 Species 0.000 claims description 5
241001465754 Metazoa Species 0.000 claims description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 5
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
UTMWGKILIFRFBR-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-iodo-1-methyl-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(I)=CC=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 UTMWGKILIFRFBR-UHFFFAOYSA-N 0.000 claims description 5
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
239000011591 potassium Chemical group 0.000 claims description 5
229910052700 potassium Inorganic materials 0.000 claims description 5
208000007514 Herpes zoster Diseases 0.000 claims description 4
150000001413 amino acids Chemical class 0.000 claims description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
238000001727 in vivo Methods 0.000 claims description 4
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
150000002923 oximes Chemical class 0.000 claims description 4
ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 4
FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 claims description 3
IUPIYIPBNCJDBK-UHFFFAOYSA-N 8-[3-(carbamoylamino)-3-methylbutyl]-n-[(4-chlorophenyl)methyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(CCC(C)(C)NC(N)=O)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 IUPIYIPBNCJDBK-UHFFFAOYSA-N 0.000 claims description 3
102000016928 DNA-directed DNA polymerase Human genes 0.000 claims description 3
241000700584 Simplexvirus Species 0.000 claims description 3
108020005202 Viral DNA Proteins 0.000 claims description 3
241000700605 Viruses Species 0.000 claims description 3
230000037396 body weight Effects 0.000 claims description 3
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
238000000338 in vitro Methods 0.000 claims description 3
208000015181 infectious disease Diseases 0.000 claims description 3
CDRSBPYJKRZQAY-UHFFFAOYSA-N methyl morpholine-4-carboxylate Chemical compound COC(=O)N1CCOCC1 CDRSBPYJKRZQAY-UHFFFAOYSA-N 0.000 claims description 3
LWFDHNMMJRMOQR-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3,3-dicyclopropyl-3-hydroxyprop-1-ynyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CC(O)(C3CC3)C3CC3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 LWFDHNMMJRMOQR-UHFFFAOYSA-N 0.000 claims description 3
IQNHHZFHQNLZFV-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(dimethylamino)prop-1-ynyl]-1-methyl-6-(oxan-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound C=1C(C(C(C(=O)NCC=2C=CC(Cl)=CC=2)=NN2C)=O)=C2C(C#CCN(C)C)=CC=1CC1CCOCC1 IQNHHZFHQNLZFV-UHFFFAOYSA-N 0.000 claims description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
229920002554 vinyl polymer Polymers 0.000 claims description 3
125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
FFBMTJGWCQFAET-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-methyl-6-(morpholin-4-ylmethyl)-8-(oxan-4-ylamino)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(NC3CCOCC3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 FFBMTJGWCQFAET-UHFFFAOYSA-N 0.000 claims description 2
WACKJXWKGISGMV-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-1-methyl-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(C#CCO)=CC=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 WACKJXWKGISGMV-UHFFFAOYSA-N 0.000 claims description 2
IGGBOIMQUDGDFQ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(4-hydroxybut-1-ynyl)-1-methyl-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(C#CCCO)=CC=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 IGGBOIMQUDGDFQ-UHFFFAOYSA-N 0.000 claims description 2
BDCBBWFHVXEOEM-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-hydroxy-3-phenylprop-1-ynyl)-1-methyl-6-(oxan-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CC3CCOCC3)=CC(C#CC(O)C=3C=CC=CC=3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 BDCBBWFHVXEOEM-UHFFFAOYSA-N 0.000 claims description 2
VHRCBXTZDHWSDC-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(4-hydroxybut-1-ynyl)-1-methyl-6-(oxan-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CC3CCOCC3)=CC(C#CCCO)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 VHRCBXTZDHWSDC-UHFFFAOYSA-N 0.000 claims description 2
LJDJMZNPIKBNLC-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[(3-cyanophenyl)methylamino]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(NCC=3C=C(C=CC=3)C#N)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 LJDJMZNPIKBNLC-UHFFFAOYSA-N 0.000 claims description 2
HVSQSBRLGFTPJH-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[(3-hydroxypiperidin-1-yl)methyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(CN3CC(O)CCC3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 HVSQSBRLGFTPJH-UHFFFAOYSA-N 0.000 claims description 2
KBMZTGBJUCLVQB-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[(4-hydroxypiperidin-1-yl)methyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(CN3CCC(O)CC3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 KBMZTGBJUCLVQB-UHFFFAOYSA-N 0.000 claims description 2
OHCSCAFVUDNQCQ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(dimethylamino)propyl]-1-methyl-6-(oxan-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound C=1C(C(C(C(=O)NCC=2C=CC(Cl)=CC=2)=NN2C)=O)=C2C(CCCN(C)C)=CC=1CC1CCOCC1 OHCSCAFVUDNQCQ-UHFFFAOYSA-N 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 7
SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims 2
125000003545 alkoxy group Chemical group 0.000 claims 2
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
KOWOAQOWCBLGSN-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-[(4-chlorophenyl)sulfinylmethyl]-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1CNC(=O)C(C(C1=CC(CN2CCOCC2)=CC=C11)=O)=NN1CS(=O)C1=CC=C(Cl)C=C1 KOWOAQOWCBLGSN-UHFFFAOYSA-N 0.000 claims 2
RQUFUKYFBUYAKP-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-methyl-6-(oxan-4-ylmethyl)-4-oxo-8-(2-phenylethynyl)cinnoline-3-carboxamide Chemical compound O=C1C2=CC(CC3CCOCC3)=CC(C#CC=3C=CC=CC=3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 RQUFUKYFBUYAKP-UHFFFAOYSA-N 0.000 claims 2
NDBMDZWPOMWAJO-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(1,1-dioxo-1,4-thiazinan-4-yl)prop-1-ynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCN3CCS(=O)(=O)CC3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 NDBMDZWPOMWAJO-UHFFFAOYSA-N 0.000 claims 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
CVAWACBLSANHSQ-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxamide Chemical compound C1=CC=CC2=C(O)C(C(=O)N)=CN=C21 CVAWACBLSANHSQ-UHFFFAOYSA-N 0.000 claims 1
XTTZBGVSJSCQQZ-UHFFFAOYSA-N 8-[(1-acetylpiperidin-4-yl)amino]-n-[(4-chlorophenyl)methyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound C1CN(C(=O)C)CCC1NC1=CC(CN2CCOCC2)=CC(C2=O)=C1N(C)N=C2C(=O)NCC1=CC=C(Cl)C=C1 XTTZBGVSJSCQQZ-UHFFFAOYSA-N 0.000 claims 1
FAXGYPWIXVQXPT-UHFFFAOYSA-N 8-[3-(carbamoylamino)-3-methylbut-1-ynyl]-n-[(4-chlorophenyl)methyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CC(C)(C)NC(N)=O)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 FAXGYPWIXVQXPT-UHFFFAOYSA-N 0.000 claims 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 claims 1
HWVBLJDVOIKCCO-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-(3-methylsulfanylpropyl)-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC=C2N(CCCSC)N=C1C(=O)NCC1=CC=C(Cl)C=C1 HWVBLJDVOIKCCO-UHFFFAOYSA-N 0.000 claims 1
NGFJCAKCMZRCEV-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-(methylsulfanylmethyl)-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC=C2N(CSC)N=C1C(=O)NCC1=CC=C(Cl)C=C1 NGFJCAKCMZRCEV-UHFFFAOYSA-N 0.000 claims 1
LHYKDCJOHNJEFP-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxo-8-(thiomorpholin-4-ylmethyl)cinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(CN3CCSCC3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 LHYKDCJOHNJEFP-UHFFFAOYSA-N 0.000 claims 1
QITJVJKKCWVALM-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-methyl-6-(morpholin-4-ylmethyl)-8-[(3-nitrophenyl)methylamino]-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(NCC=3C=C(C=CC=3)[N+]([O-])=O)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 QITJVJKKCWVALM-UHFFFAOYSA-N 0.000 claims 1
JNFRDNVROKEDSI-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(3-hydroxypropyl)-1-methyl-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CCCO)=CC=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 JNFRDNVROKEDSI-UHFFFAOYSA-N 0.000 claims 1
ATXHYNPFBGCDQN-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(2-cyclopropylethyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(CCC3CC3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 ATXHYNPFBGCDQN-UHFFFAOYSA-N 0.000 claims 1
UEWGZGQKIXOLPF-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3,3-dicyclopropyl-3-hydroxypropyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(CCC(O)(C3CC3)C3CC3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 UEWGZGQKIXOLPF-UHFFFAOYSA-N 0.000 claims 1
RPBKFQSUWFIROK-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-hydroxy-3-methylbutyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(CCC(C)(C)O)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 RPBKFQSUWFIROK-UHFFFAOYSA-N 0.000 claims 1
WAMOGUUOMNZPIV-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-hydroxy-3-phenylpropyl)-1-methyl-6-(oxan-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CC3CCOCC3)=CC(CCC(O)C=3C=CC=CC=3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 WAMOGUUOMNZPIV-UHFFFAOYSA-N 0.000 claims 1
YASDWJVMKZKIBV-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-imidazol-1-ylprop-1-ynyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCN3C=NC=C3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 YASDWJVMKZKIBV-UHFFFAOYSA-N 0.000 claims 1
HWUFLSKPCHQAAO-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(4-hydroxybutyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(CCCCO)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 HWUFLSKPCHQAAO-UHFFFAOYSA-N 0.000 claims 1
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MCDCOAVDSYHTBT-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(2-cyclopropylethynyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CC3CC3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 MCDCOAVDSYHTBT-UHFFFAOYSA-N 0.000 description 1
IKEKPIOAPNUBFO-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-imidazol-1-ylpropyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(CCCN3C=NC=C3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 IKEKPIOAPNUBFO-UHFFFAOYSA-N 0.000 description 1
QCOQJQMLEWWQHK-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(4-hydroxybutyl)-1-methyl-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC=CC(CCCCO)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 QCOQJQMLEWWQHK-UHFFFAOYSA-N 0.000 description 1
NKFFMRPBXLHYHY-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(4-hydroxybutyl)-1-methyl-6-(oxan-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CC3CCOCC3)=CC(CCCCO)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 NKFFMRPBXLHYHY-UHFFFAOYSA-N 0.000 description 1
ZMBYSUXHLBMJQL-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(hydroxymethyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(CO)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 ZMBYSUXHLBMJQL-UHFFFAOYSA-N 0.000 description 1
SJZXJLIBQCRCQS-KRWDZBQOSA-N n-[(4-chlorophenyl)methyl]-8-[(3s)-3-hydroxybut-1-ynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound C=1C(C(C(C(=O)NCC=2C=CC(Cl)=CC=2)=NN2C)=O)=C2C(C#C[C@@H](O)C)=CC=1CN1CCOCC1 SJZXJLIBQCRCQS-KRWDZBQOSA-N 0.000 description 1
AIAZXAVEVBLIAQ-KRWDZBQOSA-N n-[(4-chlorophenyl)methyl]-8-[(3s)-3-hydroxybutyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound C=1C(C(C(C(=O)NCC=2C=CC(Cl)=CC=2)=NN2C)=O)=C2C(CC[C@@H](O)C)=CC=1CN1CCOCC1 AIAZXAVEVBLIAQ-KRWDZBQOSA-N 0.000 description 1
DCMFWMPJGDVNEW-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[2-(1-hydroxycyclohexyl)ethynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CC3(O)CCCCC3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 DCMFWMPJGDVNEW-UHFFFAOYSA-N 0.000 description 1
YJMNLPRMBFMFDL-UHFFFAOYSA-N n-diazo-2-methylbenzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)N=[N+]=[N-] YJMNLPRMBFMFDL-UHFFFAOYSA-N 0.000 description 1
201000011216 nasopharynx carcinoma Diseases 0.000 description 1
230000001613 neoplastic effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000007935 oral tablet Substances 0.000 description 1
239000007968 orange flavor Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000006072 paste Substances 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960003742 phenol Drugs 0.000 description 1
239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000002243 precursor Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
230000008569 process Effects 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
238000012289 standard assay Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
229940086735 succinate Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
229940098465 tincture Drugs 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 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
QTKHQYWRGFZFHG-UHFFFAOYSA-N trioctylsilicon Chemical compound CCCCCCCC[Si](CCCCCCCC)CCCCCCCC QTKHQYWRGFZFHG-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
102000003390 tumor necrosis factor Human genes 0.000 description 1
241000701447 unidentified baculovirus Species 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000009637 wintergreen oil Substances 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/28—Cinnolines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Virology (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Oncology (AREA)
Engineering & Computer Science (AREA)
Communicable Diseases (AREA)
Bioinformatics & Cheminformatics (AREA)
Biotechnology (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SK1210-2002A 2000-03-21 2001-03-15 4-oxo-1,4-dihydro-3-cinolínkarboxamidy ako antivírusové látky SK12102002A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US19129100P	2000-03-21	2000-03-21
PCT/US2001/005811 WO2001070706A2 (en)	2000-03-21	2001-03-15	4-oxo-1,4-dihydro-3-cinnolinecarboxamides as antiviral agents

Publications (1)

Publication Number	Publication Date
SK12102002A3 true SK12102002A3 (sk)	2003-03-04

Family

ID=22704885

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1210-2002A SK12102002A3 (sk)	2000-03-21	2001-03-15	4-oxo-1,4-dihydro-3-cinolínkarboxamidy ako antivírusové látky

Country Status (28)

Country	Link
US (1)	US6624160B2 (xx)
EP (1)	EP1265873B1 (xx)
JP (1)	JP2003528087A (xx)
KR (1)	KR20020081479A (xx)
CN (1)	CN1406228A (xx)
AR (1)	AR027978A1 (xx)
AT (1)	ATE252086T1 (xx)
AU (1)	AU2001247224A1 (xx)
BR (1)	BR0109487A (xx)
CA (1)	CA2400000A1 (xx)
CZ (1)	CZ20023141A3 (xx)
DE (1)	DE60100999T2 (xx)
DK (1)	DK1265873T3 (xx)
EA (1)	EA200201002A1 (xx)
EE (1)	EE200200541A (xx)
ES (1)	ES2208581T3 (xx)
HK (1)	HK1052694A1 (xx)
HU (1)	HUP0300326A3 (xx)
IL (1)	IL151787A0 (xx)
MX (1)	MXPA02009251A (xx)
NO (1)	NO20024502L (xx)
NZ (1)	NZ521524A (xx)
PL (1)	PL357443A1 (xx)
PT (1)	PT1265873E (xx)
SI (1)	SI1265873T1 (xx)
SK (1)	SK12102002A3 (xx)
WO (1)	WO2001070706A2 (xx)
ZA (1)	ZA200207540B (xx)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PE20011349A1 (es) *	2000-06-16	2002-01-19	Upjohn Co	1-aril-4-oxo-1,4-dihidro-3-quinolincarboxamidas como agentes antivirales
JP6237779B2 (ja) *	2012-11-03	2017-11-29	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	サイトメガロウイルスの阻害薬
US11072610B2 (en)	2018-09-12	2021-07-27	Novartis Ag	Antiviral pyridopyrazinedione compounds
CN120842223A (zh)	2019-09-26	2025-10-28	诺华股份有限公司	抗病毒吡唑并吡啶酮化合物

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8513639D0 (en)	1985-05-30	1985-07-03	Ici America Inc	Cinnoline compounds
GB8702288D0 (en)	1987-02-02	1987-03-11	Erba Farmitalia	Cinnoline-carboxamides
JPH11510156A (ja)	1995-08-02	1999-09-07	カイロサイエンス・リミテッド	キノロン類およびその医療上の使用
ES2193252T3 (es)	1995-08-02	2003-11-01	Darwin Discovery Ltd	Quinolonas y su uso terapeutico.
ES2248923T3 (es)	1997-12-22	2006-03-16	PHARMACIA & UPJOHN COMPANY LLC	4-hydroxiquinolin-3-carboxamidas y hidrazidas como agentes antivirales.
EP0978516A4 (en)	1998-01-29	2001-01-10	Suntory Ltd	1-CYCLOALKYL-1,8-NAPHTHYRIDINE-4-ONE DERIVATIVES HAVING PHOSPHODIESTERASE IV INHIBITING ACTIVITY

2001
- 2001-03-15 CN CN01805756A patent/CN1406228A/zh active Pending
- 2001-03-15 DE DE60100999T patent/DE60100999T2/de not_active Expired - Fee Related
- 2001-03-15 MX MXPA02009251A patent/MXPA02009251A/es active IP Right Grant
- 2001-03-15 EA EA200201002A patent/EA200201002A1/ru unknown
- 2001-03-15 DK DK01920138T patent/DK1265873T3/da active
- 2001-03-15 SK SK1210-2002A patent/SK12102002A3/sk unknown
- 2001-03-15 SI SI200130046T patent/SI1265873T1/xx unknown
- 2001-03-15 KR KR1020027012466A patent/KR20020081479A/ko not_active Withdrawn
- 2001-03-15 ES ES01920138T patent/ES2208581T3/es not_active Expired - Lifetime
- 2001-03-15 NZ NZ521524A patent/NZ521524A/en unknown
- 2001-03-15 EP EP01920138A patent/EP1265873B1/en not_active Expired - Lifetime
- 2001-03-15 WO PCT/US2001/005811 patent/WO2001070706A2/en not_active Ceased
- 2001-03-15 BR BR0109487-4A patent/BR0109487A/pt not_active IP Right Cessation
- 2001-03-15 IL IL15178701A patent/IL151787A0/xx unknown
- 2001-03-15 CA CA002400000A patent/CA2400000A1/en not_active Abandoned
- 2001-03-15 CZ CZ20023141A patent/CZ20023141A3/cs unknown
- 2001-03-15 HU HU0300326A patent/HUP0300326A3/hu unknown
- 2001-03-15 PL PL01357443A patent/PL357443A1/xx not_active Application Discontinuation
- 2001-03-15 AT AT01920138T patent/ATE252086T1/de not_active IP Right Cessation
- 2001-03-15 PT PT01920138T patent/PT1265873E/pt unknown
- 2001-03-15 EE EEP200200541A patent/EE200200541A/xx unknown
- 2001-03-15 AU AU2001247224A patent/AU2001247224A1/en not_active Abandoned
- 2001-03-15 JP JP2001568916A patent/JP2003528087A/ja active Pending
- 2001-03-15 US US09/808,836 patent/US6624160B2/en not_active Expired - Fee Related
- 2001-03-15 HK HK03104900.8A patent/HK1052694A1/zh unknown
- 2001-03-20 AR ARP010101303A patent/AR027978A1/es unknown
2002
- 2002-09-19 ZA ZA200207540A patent/ZA200207540B/en unknown
- 2002-09-20 NO NO20024502A patent/NO20024502L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
HK1052694A1 (zh)	2003-09-26
CA2400000A1 (en)	2001-09-27
EP1265873B1 (en)	2003-10-15
HUP0300326A3 (en)	2003-09-29
AR027978A1 (es)	2003-04-23
DE60100999D1 (en)	2003-11-20
PL357443A1 (en)	2004-07-26
SI1265873T1 (en)	2004-02-29
US20020045619A1 (en)	2002-04-18
JP2003528087A (ja)	2003-09-24
ATE252086T1 (de)	2003-11-15
EP1265873A2 (en)	2002-12-18
ZA200207540B (en)	2003-12-19
CN1406228A (zh)	2003-03-26
CZ20023141A3 (cs)	2003-02-12
MXPA02009251A (es)	2004-04-05
DE60100999T2 (de)	2004-09-02
WO2001070706A2 (en)	2001-09-27
US6624160B2 (en)	2003-09-23
NO20024502D0 (no)	2002-09-20
WO2001070706A3 (en)	2002-05-10
AU2001247224A1 (en)	2001-10-03
KR20020081479A (ko)	2002-10-26
PT1265873E (pt)	2004-03-31
DK1265873T3 (da)	2004-02-16
NZ521524A (en)	2004-04-30
HUP0300326A2 (hu)	2003-07-28
ES2208581T3 (es)	2004-06-16
NO20024502L (no)	2002-11-20
EE200200541A (et)	2004-04-15
EA200201002A1 (ru)	2003-02-27
BR0109487A (pt)	2003-06-10
IL151787A0 (en)	2003-04-10

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