MX2008014771A - Derivados de piperidina como inhibidores del virus del papiloma humano. - Google Patents
Derivados de piperidina como inhibidores del virus del papiloma humano.Info
- Publication number
- MX2008014771A MX2008014771A MX2008014771A MX2008014771A MX2008014771A MX 2008014771 A MX2008014771 A MX 2008014771A MX 2008014771 A MX2008014771 A MX 2008014771A MX 2008014771 A MX2008014771 A MX 2008014771A MX 2008014771 A MX2008014771 A MX 2008014771A
- Authority
- MX
- Mexico
- Prior art keywords
- phenyl
- group
- piperidin
- methoxy
- methyl
- Prior art date
Links
- 241000701806 Human papillomavirus Species 0.000 title description 20
- 239000003112 inhibitor Substances 0.000 title description 2
- 150000003053 piperidines Chemical class 0.000 title 1
- -1 monoalkylamino Chemical group 0.000 claims abstract description 251
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 126
- 239000002253 acid Substances 0.000 claims abstract description 105
- 125000003118 aryl group Chemical group 0.000 claims abstract description 105
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 74
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 56
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 42
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 41
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 32
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 32
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 27
- 239000000651 prodrug Substances 0.000 claims abstract description 16
- 229940002612 prodrug Drugs 0.000 claims abstract description 16
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 147
- 150000001875 compounds Chemical class 0.000 claims description 140
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 82
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 73
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 67
- 125000005843 halogen group Chemical group 0.000 claims description 55
- 150000002148 esters Chemical class 0.000 claims description 40
- 239000005711 Benzoic acid Substances 0.000 claims description 37
- 125000002252 acyl group Chemical group 0.000 claims description 34
- 239000000543 intermediate Substances 0.000 claims description 34
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 26
- 150000001408 amides Chemical class 0.000 claims description 25
- 229920006395 saturated elastomer Polymers 0.000 claims description 21
- 241001631646 Papillomaviridae Species 0.000 claims description 18
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 18
- 150000002430 hydrocarbons Chemical class 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
- 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 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- 201000010153 skin papilloma Diseases 0.000 claims description 15
- 206010059313 Anogenital warts Diseases 0.000 claims description 14
- 208000015181 infectious disease Diseases 0.000 claims description 13
- 208000000260 Warts Diseases 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 208000000907 Condylomata Acuminata Diseases 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- 208000025009 anogenital human papillomavirus infection Diseases 0.000 claims description 8
- 201000004201 anogenital venereal wart Diseases 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 230000003902 lesion Effects 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 6
- 201000009030 Carcinoma Diseases 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 239000000460 chlorine Substances 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
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 5
- 208000009458 Carcinoma in Situ Diseases 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 238000010511 deprotection reaction Methods 0.000 claims description 5
- 230000009841 epithelial lesion Effects 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000005541 phosphonamide group Chemical group 0.000 claims description 5
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- 150000003456 sulfonamides Chemical class 0.000 claims description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 5
- 150000003536 tetrazoles Chemical class 0.000 claims description 5
- 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 4
- 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 4
- 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 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 206010023849 Laryngeal papilloma Diseases 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 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 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
- 230000006378 damage Effects 0.000 claims description 4
- 201000000089 larynx squamous papilloma Diseases 0.000 claims description 4
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 4
- 208000001307 recurrent respiratory papillomatosis Diseases 0.000 claims description 4
- WNISLBYEVMQVLV-UHFFFAOYSA-N 1-(2-piperidin-1-ylphenyl)-1-[4-(trifluoromethoxy)phenyl]hydrazine Chemical compound C=1C=CC=C(N2CCCCC2)C=1N(N)C1=CC=C(OC(F)(F)F)C=C1 WNISLBYEVMQVLV-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
- NJRSWQNSLCCJOU-UHFFFAOYSA-N 1-(4-phenylsulfanylphenyl)-1-(2-piperidin-1-ylphenyl)hydrazine Chemical compound C=1C=CC=C(N2CCCCC2)C=1N(N)C(C=C1)=CC=C1SC1=CC=CC=C1 NJRSWQNSLCCJOU-UHFFFAOYSA-N 0.000 claims description 3
- 241000934136 Verruca Species 0.000 claims description 3
- 206010006060 bowenoid papulosis Diseases 0.000 claims description 3
- 201000004196 common wart Diseases 0.000 claims description 3
- 210000000795 conjunctiva Anatomy 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 201000004303 plantar wart Diseases 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
- 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 2
- 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 2
- LXSMJKPMYLVBPZ-UHFFFAOYSA-N 1-(4-cyclohexyloxyphenyl)-1-(2-piperidin-1-ylphenyl)hydrazine Chemical compound C=1C=CC=C(N2CCCCC2)C=1N(N)C(C=C1)=CC=C1OC1CCCCC1 LXSMJKPMYLVBPZ-UHFFFAOYSA-N 0.000 claims description 2
- WNGWESJEDNIPAQ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-1-(2-methyl-6-piperidin-1-ylphenyl)hydrazine Chemical compound C1=CC(OC)=CC=C1N(N)C1=C(C)C=CC=C1N1CCCCC1 WNGWESJEDNIPAQ-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- NSFDPVLRZBOVSJ-UHFFFAOYSA-N 1-[4-(4-methoxyphenyl)-3-methylphenyl]-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=C1C NSFDPVLRZBOVSJ-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 229940095102 methyl benzoate Drugs 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 6
- JXHYCCGOZUGBFD-UHFFFAOYSA-N benzoic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=CC=C1 JXHYCCGOZUGBFD-UHFFFAOYSA-N 0.000 claims 3
- BJPJHHCPEWXOGB-UHFFFAOYSA-N 1-[4-(4-chlorophenoxy)phenyl]-1-(2-piperidin-1-ylphenyl)hydrazine Chemical compound C=1C=CC=C(N2CCCCC2)C=1N(N)C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 BJPJHHCPEWXOGB-UHFFFAOYSA-N 0.000 claims 1
- RWFXDZIZBGXSNL-UHFFFAOYSA-N 2-methoxybenzoic acid;hydrochloride Chemical compound Cl.COC1=CC=CC=C1C(O)=O RWFXDZIZBGXSNL-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 230000001012 protector Effects 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract description 3
- 150000002367 halogens Chemical class 0.000 abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 239000001301 oxygen Substances 0.000 abstract description 3
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 229940124686 HPV inhibitor Drugs 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 239000000047 product Substances 0.000 description 297
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 156
- 238000004128 high performance liquid chromatography Methods 0.000 description 146
- 238000004949 mass spectrometry Methods 0.000 description 144
- 238000005481 NMR spectroscopy Methods 0.000 description 137
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 92
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 86
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 73
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- 230000002829 reductive effect Effects 0.000 description 64
- 239000000243 solution Substances 0.000 description 61
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- 239000000758 substrate Substances 0.000 description 48
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 46
- 238000002360 preparation method Methods 0.000 description 43
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 41
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 25
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- 238000004587 chromatography analysis Methods 0.000 description 23
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- 235000010288 sodium nitrite Nutrition 0.000 description 23
- 238000000921 elemental analysis Methods 0.000 description 21
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 21
- 239000012280 lithium aluminium hydride Substances 0.000 description 21
- NTIGNJOEVBTPJJ-UHFFFAOYSA-N 3,3-dibromopentane Chemical compound CCC(Br)(Br)CC NTIGNJOEVBTPJJ-UHFFFAOYSA-N 0.000 description 20
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 15
- KKHJTSPUUIRIOP-UHFFFAOYSA-J tetrachlorostannane;hydrate Chemical compound O.Cl[Sn](Cl)(Cl)Cl KKHJTSPUUIRIOP-UHFFFAOYSA-J 0.000 description 15
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
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- BOLQPGRSJMIKMA-UHFFFAOYSA-N n-(4-benzylphenyl)-2-piperidin-1-ylaniline Chemical compound C=1C=C(NC=2C(=CC=CC=2)N2CCCCC2)C=CC=1CC1=CC=CC=C1 BOLQPGRSJMIKMA-UHFFFAOYSA-N 0.000 description 1
- UPPLMUAPDBEEFM-UHFFFAOYSA-N n-(4-bromo-3-methylphenyl)-2-methyl-6-nitroaniline Chemical compound C1=C(Br)C(C)=CC(NC=2C(=CC=CC=2C)[N+]([O-])=O)=C1 UPPLMUAPDBEEFM-UHFFFAOYSA-N 0.000 description 1
- LJVBGRFALKNDJE-UHFFFAOYSA-N n-(4-bromophenyl)-2-methyl-6-nitroaniline Chemical compound CC1=CC=CC([N+]([O-])=O)=C1NC1=CC=C(Br)C=C1 LJVBGRFALKNDJE-UHFFFAOYSA-N 0.000 description 1
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- GMFUKKONFZISMI-UHFFFAOYSA-N n-(4-bromophenyl)-2-nitroaniline Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(Br)C=C1 GMFUKKONFZISMI-UHFFFAOYSA-N 0.000 description 1
- CFYFXICTZBIGCM-UHFFFAOYSA-N n-(4-bromophenyl)-2-piperidin-1-ylaniline Chemical compound C1=CC(Br)=CC=C1NC1=CC=CC=C1N1CCCCC1 CFYFXICTZBIGCM-UHFFFAOYSA-N 0.000 description 1
- XCCAWJIMKYHDSC-UHFFFAOYSA-N n-(4-cyclohexyloxyphenyl)-2-nitroaniline Chemical compound [O-][N+](=O)C1=CC=CC=C1NC(C=C1)=CC=C1OC1CCCCC1 XCCAWJIMKYHDSC-UHFFFAOYSA-N 0.000 description 1
- WYXDSPMRWCZSRJ-UHFFFAOYSA-N n-(4-cyclohexyloxyphenyl)-2-piperidin-1-ylaniline Chemical compound C1CCCCC1OC(C=C1)=CC=C1NC1=CC=CC=C1N1CCCCC1 WYXDSPMRWCZSRJ-UHFFFAOYSA-N 0.000 description 1
- CWRPCBMKIREHDB-UHFFFAOYSA-N n-(4-cyclohexylphenyl)-2-nitroaniline Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=C(C2CCCCC2)C=C1 CWRPCBMKIREHDB-UHFFFAOYSA-N 0.000 description 1
- IGRCXXAANLZZNB-UHFFFAOYSA-N n-(4-cyclohexylphenyl)-2-piperidin-1-ylaniline Chemical compound C1CCCCC1C(C=C1)=CC=C1NC1=CC=CC=C1N1CCCCC1 IGRCXXAANLZZNB-UHFFFAOYSA-N 0.000 description 1
- AHAWXQYYEQGQER-UHFFFAOYSA-N n-(4-methoxyphenyl)-2-methyl-6-nitroaniline Chemical compound C1=CC(OC)=CC=C1NC1=C(C)C=CC=C1[N+]([O-])=O AHAWXQYYEQGQER-UHFFFAOYSA-N 0.000 description 1
- JLIRPISIPQMEDU-UHFFFAOYSA-N n-(4-methoxyphenyl)-2-nitroaniline Chemical compound C1=CC(OC)=CC=C1NC1=CC=CC=C1[N+]([O-])=O JLIRPISIPQMEDU-UHFFFAOYSA-N 0.000 description 1
- CNSRDKAUPIRUDA-UHFFFAOYSA-N n-(4-methoxyphenyl)-2-piperidin-1-ylaniline Chemical compound C1=CC(OC)=CC=C1NC1=CC=CC=C1N1CCCCC1 CNSRDKAUPIRUDA-UHFFFAOYSA-N 0.000 description 1
- MZZAKYDRNCNQHW-UHFFFAOYSA-N n-(4-phenoxyphenyl)-2-piperidin-1-ylaniline Chemical compound C1CCCCN1C1=CC=CC=C1NC(C=C1)=CC=C1OC1=CC=CC=C1 MZZAKYDRNCNQHW-UHFFFAOYSA-N 0.000 description 1
- LYHGOLBDUDPJEV-UHFFFAOYSA-N n-(4-phenylmethoxyphenyl)-2-piperidin-1-ylaniline Chemical compound C=1C=CC=CC=1COC(C=C1)=CC=C1NC1=CC=CC=C1N1CCCCC1 LYHGOLBDUDPJEV-UHFFFAOYSA-N 0.000 description 1
- NJFFGHDUIISOHY-UHFFFAOYSA-N n-(4-phenylsulfanylphenyl)-2-piperidin-1-ylaniline Chemical compound C1CCCCN1C1=CC=CC=C1NC(C=C1)=CC=C1SC1=CC=CC=C1 NJFFGHDUIISOHY-UHFFFAOYSA-N 0.000 description 1
- UADTVQKLPGDTNL-UHFFFAOYSA-N n-[(3-methoxyphenyl)methyl]-2-piperidin-1-ylaniline Chemical compound COC1=CC=CC(CNC=2C(=CC=CC=2)N2CCCCC2)=C1 UADTVQKLPGDTNL-UHFFFAOYSA-N 0.000 description 1
- QDEQSRMGTXMRFW-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-2-piperidin-1-ylaniline Chemical compound C1=CC(OC)=CC=C1CNC1=CC=CC=C1N1CCCCC1 QDEQSRMGTXMRFW-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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000005305 organ development Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 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
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000005633 phthalidyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229940068585 podofilox Drugs 0.000 description 1
- 229940068582 podophyllin Drugs 0.000 description 1
- YJGVMLPVUAXIQN-XVVDYKMHSA-N podophyllotoxin Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-XVVDYKMHSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035755 proliferation Effects 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
- 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
- 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
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 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
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 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
- 230000009466 transformation Effects 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
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 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
- 230000010415 tropism Effects 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 244000052613 viral pathogen Species 0.000 description 1
- 210000002845 virion 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)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 (1)
| Publication Number | Publication Date |
|---|---|
| MX2008014771A true MX2008014771A (es) | 2008-11-28 |
Family
ID=37575135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2008014771A MX2008014771A (es) | 2006-05-19 | 2007-05-18 | Derivados de piperidina como inhibidores del virus del papiloma humano. |
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 (14)
| 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 |
| CN108530310B (zh) * | 2017-03-02 | 2025-01-28 | 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 |
| EP3999493B1 (en) | 2019-07-19 | 2023-12-20 | Abivax | Aryl-n-aryl derivatives for treating a rna virus infection |
| 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 |
| CZ301802B6 (cs) * | 1999-03-19 | 2010-06-30 | Vertex Pharmaceuticals Incorporated | Deriváty mocoviny jako inhibitory IMPDH a farmaceutické prostredky s jejich obsahem |
| CA2526506A1 (en) * | 2003-06-09 | 2004-12-16 | Boehringer Ingelheim International Gmbh | Inhibitors of papilloma virus |
-
2006
- 2006-05-19 FR FR0604496A patent/FR2901273B1/fr not_active Expired - Fee Related
-
2007
- 2007-05-18 JP JP2009511485A patent/JP5399237B2/ja not_active Expired - Fee Related
- 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 PT PT77292878T patent/PT2024350E/pt unknown
- 2007-05-18 US US12/300,998 patent/US8207373B2/en not_active Expired - Fee Related
- 2007-05-18 ES ES07729287.8T patent/ES2436772T3/es active Active
- 2007-05-18 AR ARP070102162A patent/AR061027A1/es not_active Application Discontinuation
- 2007-05-18 CN CN2007800218616A patent/CN101466693B/zh not_active Expired - Fee Related
- 2007-05-18 BR BRPI0711208-4A patent/BRPI0711208A2/pt not_active IP Right Cessation
- 2007-05-18 DK DK07729287.8T patent/DK2024350T3/da active
- 2007-05-18 WO PCT/EP2007/054843 patent/WO2007135106A1/fr not_active Ceased
- 2007-05-18 CA CA2652469A patent/CA2652469C/fr not_active Expired - Fee Related
-
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 |
|---|---|
| DK2024350T3 (da) | 2013-12-09 |
| FR2901273B1 (fr) | 2010-12-24 |
| CA2652469C (fr) | 2016-05-03 |
| EP2024350B1 (fr) | 2013-09-18 |
| US8207373B2 (en) | 2012-06-26 |
| US20170079968A1 (en) | 2017-03-23 |
| JP5399237B2 (ja) | 2014-01-29 |
| US9974779B2 (en) | 2018-05-22 |
| US20180021318A9 (en) | 2018-01-25 |
| US20090209586A1 (en) | 2009-08-20 |
| US20120220633A1 (en) | 2012-08-30 |
| US9452991B2 (en) | 2016-09-27 |
| WO2007135106A1 (fr) | 2007-11-29 |
| JP2009537595A (ja) | 2009-10-29 |
| BRPI0711208A2 (pt) | 2011-03-22 |
| CN101466693B (zh) | 2012-12-12 |
| PT2024350E (pt) | 2013-12-11 |
| EP2024350A1 (fr) | 2009-02-18 |
| ES2436772T3 (es) | 2014-01-07 |
| CA2652469A1 (fr) | 2007-11-29 |
| AR061027A1 (es) | 2008-07-30 |
| FR2901273A1 (fr) | 2007-11-23 |
| CN101466693A (zh) | 2009-06-24 |
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