JP5399237B2 - ヒトパピローマウイルス阻害剤としてのピペリジン誘導体 - Google Patents
ヒトパピローマウイルス阻害剤としてのピペリジン誘導体 Download PDFInfo
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- JP5399237B2 JP5399237B2 JP2009511485A JP2009511485A JP5399237B2 JP 5399237 B2 JP5399237 B2 JP 5399237B2 JP 2009511485 A JP2009511485 A JP 2009511485A JP 2009511485 A JP2009511485 A JP 2009511485A JP 5399237 B2 JP5399237 B2 JP 5399237B2
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- Prior art keywords
- phenyl
- group
- methoxy
- piperidin
- alkyl
- Prior art date
- Legal status (The legal status 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 status listed.)
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- 241000701806 Human papillomavirus Species 0.000 title description 22
- 239000003112 inhibitor Substances 0.000 title 1
- 150000003053 piperidines Chemical class 0.000 title 1
- -1 monoalkylamino Chemical group 0.000 claims description 242
- 150000001875 compounds Chemical class 0.000 claims description 153
- 238000000034 method Methods 0.000 claims description 152
- 125000000217 alkyl group Chemical group 0.000 claims description 121
- 125000003118 aryl group Chemical group 0.000 claims description 99
- 239000002253 acid Substances 0.000 claims description 82
- 125000001188 haloalkyl group Chemical group 0.000 claims description 76
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 66
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 65
- 125000003545 alkoxy group Chemical group 0.000 claims description 58
- 125000005843 halogen group Chemical group 0.000 claims description 58
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 43
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 41
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 125000002252 acyl group Chemical group 0.000 claims description 36
- 150000002148 esters Chemical class 0.000 claims description 34
- 125000004414 alkyl thio group Chemical group 0.000 claims description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 150000001408 amides Chemical class 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 201000010153 skin papilloma Diseases 0.000 claims description 26
- 241001631646 Papillomaviridae Species 0.000 claims description 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 17
- 208000000260 Warts Diseases 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 14
- 208000015181 infectious disease Diseases 0.000 claims description 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 12
- 239000000651 prodrug Chemical group 0.000 claims description 12
- 229940002612 prodrug Drugs 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
- 230000003902 lesion Effects 0.000 claims description 10
- 230000002265 prevention Effects 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000004185 ester group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
- 201000009030 Carcinoma Diseases 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 230000009841 epithelial lesion Effects 0.000 claims description 5
- 210000000867 larynx Anatomy 0.000 claims description 5
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- 150000003456 sulfonamides Chemical class 0.000 claims description 5
- 150000003536 tetrazoles Chemical class 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 206010068322 Oral papilloma Diseases 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 208000020082 intraepithelial neoplasia Diseases 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- LVSQBGJIBYJFBC-UHFFFAOYSA-N 1-(2-methyl-6-piperidin-1-ylphenyl)-1-[4-(trifluoromethoxy)phenyl]hydrazine Chemical compound C=1C=C(OC(F)(F)F)C=CC=1N(N)C=1C(C)=CC=CC=1N1CCCCC1 LVSQBGJIBYJFBC-UHFFFAOYSA-N 0.000 claims description 3
- SHDANUMTEWFBAB-UHFFFAOYSA-N 1-(3-phenoxyphenyl)-1-(2-piperidin-1-ylphenyl)hydrazine Chemical compound C=1C=CC=C(N2CCCCC2)C=1N(N)C(C=1)=CC=CC=1OC1=CC=CC=C1 SHDANUMTEWFBAB-UHFFFAOYSA-N 0.000 claims description 3
- GWPXAKGQGKGEHP-UHFFFAOYSA-N 1-(4-benzylphenyl)-1-(2-methyl-6-piperidin-1-ylphenyl)hydrazine Chemical compound C=1C=C(CC=2C=CC=CC=2)C=CC=1N(N)C=1C(C)=CC=CC=1N1CCCCC1 GWPXAKGQGKGEHP-UHFFFAOYSA-N 0.000 claims description 3
- YOMXWXKPUPXJBY-UHFFFAOYSA-N 1-(4-bromophenyl)-1-(2-piperidin-1-ylphenyl)hydrazine Chemical compound C=1C=CC=C(N2CCCCC2)C=1N(N)C1=CC=C(Br)C=C1 YOMXWXKPUPXJBY-UHFFFAOYSA-N 0.000 claims description 3
- JEDKEMQGKRGHPJ-UHFFFAOYSA-N 1-(4-cyclohexylphenyl)-1-(2-piperidin-1-ylphenyl)hydrazine Chemical compound C=1C=CC=C(N2CCCCC2)C=1N(N)C(C=C1)=CC=C1C1CCCCC1 JEDKEMQGKRGHPJ-UHFFFAOYSA-N 0.000 claims description 3
- PMBRUDGDSOPIEK-UHFFFAOYSA-N 1-(4-phenoxyphenyl)-1-(2-piperidin-1-ylphenyl)hydrazine Chemical compound C=1C=CC=C(N2CCCCC2)C=1N(N)C(C=C1)=CC=C1OC1=CC=CC=C1 PMBRUDGDSOPIEK-UHFFFAOYSA-N 0.000 claims description 3
- FEIZXUUGZOGGFR-UHFFFAOYSA-N 1-(4-phenylmethoxyphenyl)-1-(2-piperidin-1-ylphenyl)hydrazine Chemical compound C=1C=CC=C(N2CCCCC2)C=1N(N)C(C=C1)=CC=C1OCC1=CC=CC=C1 FEIZXUUGZOGGFR-UHFFFAOYSA-N 0.000 claims description 3
- NQBOOFUWYNHREX-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-1-(2-piperidin-1-ylphenyl)hydrazine Chemical compound C1=CC(OC)=CC=C1CN(N)C1=CC=CC=C1N1CCCCC1 NQBOOFUWYNHREX-UHFFFAOYSA-N 0.000 claims description 3
- ANYQCYYCRWNJPR-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)ethyl]-1-(2-piperidin-1-ylphenyl)hydrazine Chemical compound C1=CC(OC)=CC=C1CCN(N)C1=CC=CC=C1N1CCCCC1 ANYQCYYCRWNJPR-UHFFFAOYSA-N 0.000 claims description 3
- DCEPMVQCVPQNRZ-UHFFFAOYSA-N 1-[4-(4-fluorophenoxy)phenyl]-1-(2-methyl-6-piperidin-1-ylphenyl)hydrazine Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1N(N)C=1C(C)=CC=CC=1N1CCCCC1 DCEPMVQCVPQNRZ-UHFFFAOYSA-N 0.000 claims description 3
- ULYFJTBXDKSXHF-UHFFFAOYSA-N 1-[4-(4-fluorophenoxy)phenyl]-1-(2-piperidin-1-ylphenyl)hydrazine Chemical compound C=1C=CC=C(N2CCCCC2)C=1N(N)C(C=C1)=CC=C1OC1=CC=C(F)C=C1 ULYFJTBXDKSXHF-UHFFFAOYSA-N 0.000 claims description 3
- IBEJMYIPZYIAHO-UHFFFAOYSA-N 1-[4-(4-methoxyphenyl)phenyl]-1-(2-methyl-6-piperidin-1-ylphenyl)hydrazine Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N(N)C=2C(=CC=CC=2C)N2CCCCC2)C=C1 IBEJMYIPZYIAHO-UHFFFAOYSA-N 0.000 claims description 3
- OGLULPSAYFPEIQ-UHFFFAOYSA-N 1-[4-(4-methoxyphenyl)phenyl]-1-(2-piperidin-1-ylphenyl)hydrazine Chemical compound C1=CC(OC)=CC=C1C1=CC=C(N(N)C=2C(=CC=CC=2)N2CCCCC2)C=C1 OGLULPSAYFPEIQ-UHFFFAOYSA-N 0.000 claims description 3
- RKRHISHCYGTUMP-UHFFFAOYSA-N 1-[4-[4-(2-methyl-1,3-dithian-2-yl)phenyl]phenyl]-1-(2-methyl-6-piperidin-1-ylphenyl)hydrazine Chemical compound C=1C=C(C=2C=CC(=CC=2)C2(C)SCCCS2)C=CC=1N(N)C=1C(C)=CC=CC=1N1CCCCC1 RKRHISHCYGTUMP-UHFFFAOYSA-N 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- UZEZODGYGGMGSV-UHFFFAOYSA-N [4-(n-amino-2-piperidin-1-ylanilino)phenyl]-phenylmethanone Chemical compound C=1C=CC=C(N2CCCCC2)C=1N(N)C(C=C1)=CC=C1C(=O)C1=CC=CC=C1 UZEZODGYGGMGSV-UHFFFAOYSA-N 0.000 claims description 3
- JXHYCCGOZUGBFD-UHFFFAOYSA-N benzoic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=CC=C1 JXHYCCGOZUGBFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- UYKIMJVFSRBMFM-UHFFFAOYSA-N 1-(4-methoxyphenyl)-1-(2-piperidin-1-ylphenyl)hydrazine Chemical compound C1=CC(OC)=CC=C1N(N)C1=CC=CC=C1N1CCCCC1 UYKIMJVFSRBMFM-UHFFFAOYSA-N 0.000 claims description 2
- QZDASZPENQHNDU-UHFFFAOYSA-N 1-[(3-methoxyphenyl)methyl]-1-(2-piperidin-1-ylphenyl)hydrazine Chemical compound COC1=CC=CC(CN(N)C=2C(=CC=CC=2)N2CCCCC2)=C1 QZDASZPENQHNDU-UHFFFAOYSA-N 0.000 claims description 2
- 210000003464 cuspid Anatomy 0.000 claims description 2
- 208000037824 growth disorder Diseases 0.000 claims description 2
- 208000003154 papilloma Diseases 0.000 claims description 2
- 208000029211 papillomatosis Diseases 0.000 claims description 2
- 230000000306 recurrent effect Effects 0.000 claims description 2
- 230000000241 respiratory effect Effects 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 12
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 238000006467 substitution reaction Methods 0.000 claims 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
- MLIIKBWHZWPLEF-UHFFFAOYSA-N 1-(4-benzylphenyl)-1-(2-piperidin-1-ylphenyl)hydrazine Chemical compound C=1C=CC=C(N2CCCCC2)C=1N(N)C(C=C1)=CC=C1CC1=CC=CC=C1 MLIIKBWHZWPLEF-UHFFFAOYSA-N 0.000 claims 1
- QYCCSFVNPUAAGW-SJDTYFKWSA-N 2-methoxy-4-[(e)-3-[2-(4-methoxyphenyl)-2-(2-methyl-6-piperidin-1-ylphenyl)hydrazinyl]-3-oxoprop-1-enyl]benzoic acid;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1N(C=1C(=CC=CC=1C)N1CCCCC1)NC(=O)\C=C\C1=CC=C(C(O)=O)C(OC)=C1 QYCCSFVNPUAAGW-SJDTYFKWSA-N 0.000 claims 1
- GIHPVEIBSGCDFI-UHFFFAOYSA-N 4-[2-[2-(4-benzylphenyl)-2-(2-piperidin-1-ylphenyl)hydrazinyl]-2-oxoethyl]-5-bromo-2-methoxybenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OC)=CC(CC(=O)NN(C=2C=CC(CC=3C=CC=CC=3)=CC=2)C=2C(=CC=CC=2)N2CCCCC2)=C1Br GIHPVEIBSGCDFI-UHFFFAOYSA-N 0.000 claims 1
- MQXWIFOUTDAODG-UHFFFAOYSA-N 4-[2-[2-[4-(3-acetylphenyl)phenyl]-2-(2-piperidin-1-ylphenyl)hydrazinyl]-2-oxoethyl]-5-chloro-2-methoxybenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OC)=CC(CC(=O)NN(C=2C=CC(=CC=2)C=2C=C(C=CC=2)C(C)=O)C=2C(=CC=CC=2)N2CCCCC2)=C1Cl MQXWIFOUTDAODG-UHFFFAOYSA-N 0.000 claims 1
- JHVHAYVFPLNMSK-UHFFFAOYSA-N 4-[2-[2-[4-(4-acetylphenyl)phenyl]-2-(2-methyl-6-piperidin-1-ylphenyl)hydrazinyl]-2-oxoethyl]-5-bromo-2-methoxybenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OC)=CC(CC(=O)NN(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(C)=O)C=2C(=CC=CC=2C)N2CCCCC2)=C1Br JHVHAYVFPLNMSK-UHFFFAOYSA-N 0.000 claims 1
- HDZUJKKVJOIICW-UHFFFAOYSA-N 4-[2-[2-[4-(4-acetylphenyl)phenyl]-2-(2-piperidin-1-ylphenyl)hydrazinyl]-2-oxoethyl]-5-chloro-2-methoxybenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OC)=CC(CC(=O)NN(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(C)=O)C=2C(=CC=CC=2)N2CCCCC2)=C1Cl HDZUJKKVJOIICW-UHFFFAOYSA-N 0.000 claims 1
- QJEWWPSYKNRFEA-UHFFFAOYSA-N 4-[2-[2-[4-(benzenesulfinyl)phenyl]-2-(2-piperidin-1-ylphenyl)hydrazinyl]-2-oxoethyl]-5-bromo-2-methoxybenzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OC)=CC(CC(=O)NN(C=2C=CC(=CC=2)S(=O)C=2C=CC=CC=2)C=2C(=CC=CC=2)N2CCCCC2)=C1Br QJEWWPSYKNRFEA-UHFFFAOYSA-N 0.000 claims 1
- LVSMCAMJSUPGLS-UHFFFAOYSA-N 5-bromo-2-methoxy-4-[2-[2-(2-methyl-6-piperidin-1-ylphenyl)-2-[4-(trifluoromethoxy)phenyl]hydrazinyl]-2-oxoethyl]benzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OC)=CC(CC(=O)NN(C=2C=CC(OC(F)(F)F)=CC=2)C=2C(=CC=CC=2C)N2CCCCC2)=C1Br LVSMCAMJSUPGLS-UHFFFAOYSA-N 0.000 claims 1
- BHMLBYCRWIIQBL-UHFFFAOYSA-N 5-bromo-2-methoxy-4-[2-[2-(4-methoxyphenyl)-2-(2-methyl-6-piperidin-1-ylphenyl)hydrazinyl]-2-oxoethyl]benzoic acid Chemical compound C1=CC(OC)=CC=C1N(C=1C(=CC=CC=1C)N1CCCCC1)NC(=O)CC1=CC(OC)=C(C(O)=O)C=C1Br BHMLBYCRWIIQBL-UHFFFAOYSA-N 0.000 claims 1
- VWXFUUPZQQUKEL-UHFFFAOYSA-N 5-bromo-2-methoxy-4-[2-[2-(4-methoxyphenyl)-2-(2-methyl-6-piperidin-1-ylphenyl)hydrazinyl]-2-oxoethyl]benzoic acid;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1N(C=1C(=CC=CC=1C)N1CCCCC1)NC(=O)CC1=CC(OC)=C(C(O)=O)C=C1Br VWXFUUPZQQUKEL-UHFFFAOYSA-N 0.000 claims 1
- MZSPKVOLOHHPGH-UHFFFAOYSA-N 5-bromo-2-methoxy-4-[2-[2-(4-methoxyphenyl)-2-(2-piperidin-1-ylphenyl)hydrazinyl]-2-oxoethyl]benzoic acid;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1N(C=1C(=CC=CC=1)N1CCCCC1)NC(=O)CC1=CC(OC)=C(C(O)=O)C=C1Br MZSPKVOLOHHPGH-UHFFFAOYSA-N 0.000 claims 1
- MTYNNXGHHIATQD-UHFFFAOYSA-N 5-bromo-2-methoxy-4-[2-[2-[(3-methoxyphenyl)methyl]-2-(2-piperidin-1-ylphenyl)hydrazinyl]-2-oxoethyl]benzoic acid;hydrochloride Chemical compound Cl.COC1=CC=CC(CN(NC(=O)CC=2C(=CC(=C(OC)C=2)C(O)=O)Br)C=2C(=CC=CC=2)N2CCCCC2)=C1 MTYNNXGHHIATQD-UHFFFAOYSA-N 0.000 claims 1
- NZRZZTZSNFCQGR-UHFFFAOYSA-N 5-bromo-2-methoxy-4-[2-[2-[(4-methoxyphenyl)methyl]-2-(2-piperidin-1-ylphenyl)hydrazinyl]-2-oxoethyl]benzoic acid;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CN(C=1C(=CC=CC=1)N1CCCCC1)NC(=O)CC1=CC(OC)=C(C(O)=O)C=C1Br NZRZZTZSNFCQGR-UHFFFAOYSA-N 0.000 claims 1
- AGUVLTRJAJOBEJ-UHFFFAOYSA-N 5-bromo-2-methoxy-4-[2-[2-[4-(4-methoxyphenyl)phenyl]-2-(2-methyl-6-piperidin-1-ylphenyl)hydrazinyl]-2-oxoethyl]benzoic acid;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1=CC=C(N(NC(=O)CC=2C(=CC(=C(OC)C=2)C(O)=O)Br)C=2C(=CC=CC=2C)N2CCCCC2)C=C1 AGUVLTRJAJOBEJ-UHFFFAOYSA-N 0.000 claims 1
- XQIUNGMMRUICCU-UHFFFAOYSA-N 5-bromo-2-methoxy-4-[2-[2-[4-(4-methoxyphenyl)phenyl]-2-(2-piperidin-1-ylphenyl)hydrazinyl]-2-oxoethyl]benzoic acid;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1=CC=C(N(NC(=O)CC=2C(=CC(=C(OC)C=2)C(O)=O)Br)C=2C(=CC=CC=2)N2CCCCC2)C=C1 XQIUNGMMRUICCU-UHFFFAOYSA-N 0.000 claims 1
- CVHLEOGXAWVGSK-UHFFFAOYSA-N 5-bromo-2-methoxy-4-[2-oxo-2-[2-(2-piperidin-1-ylphenyl)-2-[4-(trifluoromethoxy)phenyl]hydrazinyl]ethyl]benzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OC)=CC(CC(=O)NN(C=2C=CC(OC(F)(F)F)=CC=2)C=2C(=CC=CC=2)N2CCCCC2)=C1Br CVHLEOGXAWVGSK-UHFFFAOYSA-N 0.000 claims 1
- ARLNBJKPBVJQOS-UHFFFAOYSA-N 5-bromo-2-methoxy-4-[2-oxo-2-[2-(3-phenoxyphenyl)-2-(2-piperidin-1-ylphenyl)hydrazinyl]ethyl]benzoic acid hydrochloride Chemical compound Cl.BrC=1C(=CC(=C(C(=O)O)C1)OC)CC(=O)NN(C1=C(C=CC=C1)N1CCCCC1)C1=CC(=CC=C1)OC1=CC=CC=C1 ARLNBJKPBVJQOS-UHFFFAOYSA-N 0.000 claims 1
- BALMGZGOTKYTNM-UHFFFAOYSA-N 5-bromo-2-methoxy-4-[2-oxo-2-[2-(4-phenoxyphenyl)-2-(2-piperidin-1-ylphenyl)hydrazinyl]ethyl]benzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OC)=CC(CC(=O)NN(C=2C=CC(OC=3C=CC=CC=3)=CC=2)C=2C(=CC=CC=2)N2CCCCC2)=C1Br BALMGZGOTKYTNM-UHFFFAOYSA-N 0.000 claims 1
- ZHKKUNRVYFVHGR-UHFFFAOYSA-N 5-bromo-2-methoxy-4-[2-oxo-2-[2-(4-phenylmethoxyphenyl)-2-(2-piperidin-1-ylphenyl)hydrazinyl]ethyl]benzoic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(OC)=CC(CC(=O)NN(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)C=2C(=CC=CC=2)N2CCCCC2)=C1Br ZHKKUNRVYFVHGR-UHFFFAOYSA-N 0.000 claims 1
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- PRUCYNIICGAELI-UHFFFAOYSA-N n-[4-(4-fluorophenoxy)phenyl]-2-methyl-6-nitroaniline Chemical compound CC1=CC=CC([N+]([O-])=O)=C1NC(C=C1)=CC=C1OC1=CC=C(F)C=C1 PRUCYNIICGAELI-UHFFFAOYSA-N 0.000 description 1
- LWIJZAOBUPWGRC-UHFFFAOYSA-N n-[4-(4-fluorophenoxy)phenyl]-2-methyl-6-piperidin-1-ylaniline Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1NC=1C(C)=CC=CC=1N1CCCCC1 LWIJZAOBUPWGRC-UHFFFAOYSA-N 0.000 description 1
- CMVZNINJTVALHA-UHFFFAOYSA-N n-[4-(4-fluorophenoxy)phenyl]-2-nitroaniline Chemical compound [O-][N+](=O)C1=CC=CC=C1NC(C=C1)=CC=C1OC1=CC=C(F)C=C1 CMVZNINJTVALHA-UHFFFAOYSA-N 0.000 description 1
- PEZYSHSSQRUDJG-UHFFFAOYSA-N n-[4-(4-fluorophenoxy)phenyl]-2-piperidin-1-ylaniline Chemical compound C1=CC(F)=CC=C1OC(C=C1)=CC=C1NC1=CC=CC=C1N1CCCCC1 PEZYSHSSQRUDJG-UHFFFAOYSA-N 0.000 description 1
- DZLPOJCGXXXLLH-UHFFFAOYSA-N n-[4-(4-methoxyphenyl)-3-methylphenyl]-2-methyl-6-piperidin-1-ylaniline Chemical compound C1=CC(OC)=CC=C1C(C(=C1)C)=CC=C1NC1=C(C)C=CC=C1N1CCCCC1 DZLPOJCGXXXLLH-UHFFFAOYSA-N 0.000 description 1
- MCRHCJGYRXSHEP-UHFFFAOYSA-N n-[4-(4-methoxyphenyl)phenyl]-2-methyl-6-piperidin-1-ylaniline Chemical compound C1=CC(OC)=CC=C1C(C=C1)=CC=C1NC1=C(C)C=CC=C1N1CCCCC1 MCRHCJGYRXSHEP-UHFFFAOYSA-N 0.000 description 1
- IAGQQSXQAOPMEA-UHFFFAOYSA-N n-[4-(4-methoxyphenyl)phenyl]-2-piperidin-1-ylaniline Chemical compound C1=CC(OC)=CC=C1C(C=C1)=CC=C1NC1=CC=CC=C1N1CCCCC1 IAGQQSXQAOPMEA-UHFFFAOYSA-N 0.000 description 1
- KMJZFJMFHOPFPJ-UHFFFAOYSA-N n-phenylpiperidin-1-amine Chemical compound C1CCCCN1NC1=CC=CC=C1 KMJZFJMFHOPFPJ-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 210000003928 nasal cavity Anatomy 0.000 description 1
- 230000009826 neoplastic cell growth Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000005305 organ development Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 238000005897 peptide coupling reaction Methods 0.000 description 1
- NCZQECUWKXITOE-UHFFFAOYSA-N phenyl-[4-(2-piperidin-1-ylanilino)phenyl]methanone Chemical compound C=1C=C(NC=2C(=CC=CC=2)N2CCCCC2)C=CC=1C(=O)C1=CC=CC=C1 NCZQECUWKXITOE-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 1
- 125000005633 phthalidyl group Chemical group 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- NCNISYUOWMIOPI-UHFFFAOYSA-N propane-1,1-dithiol Chemical compound CCC(S)S NCNISYUOWMIOPI-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000022532 regulation of transcription, DNA-dependent Effects 0.000 description 1
- 230000004390 regulation of viral genome replication Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 231100000444 skin lesion Toxicity 0.000 description 1
- 206010040882 skin lesion Diseases 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- NFEGNISFSSLEGU-UHFFFAOYSA-N tert-butyl 2-diethoxyphosphorylacetate Chemical compound CCOP(=O)(OCC)CC(=O)OC(C)(C)C NFEGNISFSSLEGU-UHFFFAOYSA-N 0.000 description 1
- DUDQEUATMXJHPB-UHFFFAOYSA-N tert-butyl n-amino-n-(2-methyl-6-nitrophenyl)carbamate Chemical compound CC1=CC=CC([N+]([O-])=O)=C1N(N)C(=O)OC(C)(C)C DUDQEUATMXJHPB-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 230000006648 viral gene expression Effects 0.000 description 1
- 230000004095 viral genome expression Effects 0.000 description 1
- 244000052613 viral pathogen Species 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
- 210000003905 vulva Anatomy 0.000 description 1
Classifications
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/12—Keratolytics, e.g. wart or anti-corn preparations
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Dermatology (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0604496 | 2006-05-19 | ||
| FR0604496A FR2901273B1 (fr) | 2006-05-19 | 2006-05-19 | Inhibiteurs du virus du papillome humain et les compositions pharmaceutiques les contenant |
| PCT/EP2007/054843 WO2007135106A1 (fr) | 2006-05-19 | 2007-05-18 | Derives de piperidine comme inhibiteurs du virus du papillome humain |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009537595A JP2009537595A (ja) | 2009-10-29 |
| JP2009537595A5 JP2009537595A5 (enExample) | 2012-06-07 |
| JP5399237B2 true JP5399237B2 (ja) | 2014-01-29 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009511485A Expired - Fee Related JP5399237B2 (ja) | 2006-05-19 | 2007-05-18 | ヒトパピローマウイルス阻害剤としてのピペリジン誘導体 |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US8207373B2 (enExample) |
| EP (1) | EP2024350B1 (enExample) |
| JP (1) | JP5399237B2 (enExample) |
| CN (1) | CN101466693B (enExample) |
| AR (1) | AR061027A1 (enExample) |
| BR (1) | BRPI0711208A2 (enExample) |
| CA (1) | CA2652469C (enExample) |
| DK (1) | DK2024350T3 (enExample) |
| ES (1) | ES2436772T3 (enExample) |
| FR (1) | FR2901273B1 (enExample) |
| MX (1) | MX2008014771A (enExample) |
| PT (1) | PT2024350E (enExample) |
| WO (1) | WO2007135106A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2923825B1 (fr) * | 2007-11-20 | 2013-05-03 | Anaconda Pharma | Nouveaux inhibiteurs du virus du papillome humain et les compositions pharmaceutiques les contenant. |
| FR2990134B1 (fr) * | 2012-05-07 | 2014-11-21 | Anaconda Pharma | Composition pharmaceutique d'un inhibiteur du virus du papillome |
| FR3000490B1 (fr) * | 2012-12-27 | 2015-03-13 | Anaconda Pharma | Procede de synthese d'une hydrazine utile dans le traitement du virus du papillome |
| ES2796276T3 (es) * | 2015-02-05 | 2020-11-26 | Ab Science | Compuestos con actividad antitumoral |
| WO2017009751A1 (en) | 2015-07-15 | 2017-01-19 | Pfizer Inc. | Pyrimidine derivatives |
| CN105582083A (zh) * | 2015-09-08 | 2016-05-18 | 石友爱 | 一种治疗鲍温样丘疹病的中药 |
| WO2018157843A1 (zh) * | 2017-03-02 | 2018-09-07 | 中国科学院上海药物研究所 | 2-(取代苯杂基)芳香甲酸类fto抑制剂，其制备方法及其应用 |
| CN109748903B (zh) * | 2017-11-01 | 2021-08-10 | 北京协和制药二厂 | 吡法齐明的制备方法 |
| EP3594206A1 (en) | 2018-07-09 | 2020-01-15 | Abivax | Phenyl-n-quinoline derivatives for treating a rna virus infection |
| EP3594205A1 (en) * | 2018-07-09 | 2020-01-15 | Abivax | Phenyl-n-aryl derivatives for treating a rna virus infection |
| JP2020127293A (ja) * | 2019-02-05 | 2020-08-20 | ファナック株式会社 | ロータコアの製造装置及びロータコアの製造方法、並びにロータ構造 |
| CN110041223B (zh) * | 2019-06-03 | 2021-10-22 | 西北师范大学 | 以肼类化合物为原料氧化合成偶氮类化合物的方法 |
| CN114276273B (zh) * | 2021-12-29 | 2024-06-21 | 维思普新材料（苏州）有限公司 | 一种基于四苯基肼类衍生物的有机电致发光材料及其电子器件 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4292429A (en) * | 1978-03-08 | 1981-09-29 | Ciba-Geigy Corporation | Imidazole urea and amido compounds |
| EE200100492A (et) * | 1999-03-19 | 2002-12-16 | Vertex Pharmaceuticals Incorporated | Ensüümi IMPDH inhibiitorid |
| JP4550811B2 (ja) * | 2003-06-09 | 2010-09-22 | 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 | パピローマウイルスのインヒビター |
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2006
- 2006-05-19 FR FR0604496A patent/FR2901273B1/fr not_active Expired - Fee Related
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2007
- 2007-05-18 JP JP2009511485A patent/JP5399237B2/ja not_active Expired - Fee Related
- 2007-05-18 AR ARP070102162A patent/AR061027A1/es not_active Application Discontinuation
- 2007-05-18 ES ES07729287.8T patent/ES2436772T3/es active Active
- 2007-05-18 WO PCT/EP2007/054843 patent/WO2007135106A1/fr not_active Ceased
- 2007-05-18 PT PT77292878T patent/PT2024350E/pt unknown
- 2007-05-18 BR BRPI0711208-4A patent/BRPI0711208A2/pt not_active IP Right Cessation
- 2007-05-18 EP EP07729287.8A patent/EP2024350B1/fr not_active Not-in-force
- 2007-05-18 MX MX2008014771A patent/MX2008014771A/es active IP Right Grant
- 2007-05-18 US US12/300,998 patent/US8207373B2/en not_active Expired - Fee Related
- 2007-05-18 CN CN2007800218616A patent/CN101466693B/zh not_active Expired - Fee Related
- 2007-05-18 CA CA2652469A patent/CA2652469C/fr not_active Expired - Fee Related
- 2007-05-18 DK DK07729287.8T patent/DK2024350T3/da active
-
2012
- 2012-05-08 US US13/466,530 patent/US9452991B2/en active Active
-
2016
- 2016-09-26 US US15/276,208 patent/US9974779B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20170079968A1 (en) | 2017-03-23 |
| US9452991B2 (en) | 2016-09-27 |
| EP2024350B1 (fr) | 2013-09-18 |
| MX2008014771A (es) | 2008-11-28 |
| AR061027A1 (es) | 2008-07-30 |
| WO2007135106A1 (fr) | 2007-11-29 |
| CA2652469A1 (fr) | 2007-11-29 |
| CA2652469C (fr) | 2016-05-03 |
| US20090209586A1 (en) | 2009-08-20 |
| US8207373B2 (en) | 2012-06-26 |
| JP2009537595A (ja) | 2009-10-29 |
| US20120220633A1 (en) | 2012-08-30 |
| FR2901273A1 (fr) | 2007-11-23 |
| EP2024350A1 (fr) | 2009-02-18 |
| US20180021318A9 (en) | 2018-01-25 |
| US9974779B2 (en) | 2018-05-22 |
| CN101466693A (zh) | 2009-06-24 |
| CN101466693B (zh) | 2012-12-12 |
| DK2024350T3 (da) | 2013-12-09 |
| BRPI0711208A2 (pt) | 2011-03-22 |
| ES2436772T3 (es) | 2014-01-07 |
| FR2901273B1 (fr) | 2010-12-24 |
| PT2024350E (pt) | 2013-12-11 |
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