NO321599B1 - Respiratorisk syncytialvirusreplikasjonsinhibitorer - Google Patents

Respiratorisk syncytialvirusreplikasjonsinhibitorer Download PDF

Info

Publication number: NO321599B1
Authority: NO; Norway
Prior art keywords: formula; piperidinyl; amino; methylbutyl; amine
Prior art date: 1999-06-28

Application number

NO20016370A

Other languages

English (en)

Norwegian (no)

Other versions

NO20016370L (no

NO20016370D0 (no

Inventor

Jean Fernand Armand Lacrampe

Koenraad Jozef Lodewij Andries

Jerome Emile George Guillemont

Marc Gaston Venet

Frans Eduard Janssens

Original Assignee

Janssen Pharmaceutica Nv

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.)

1999-06-28

Filing date

2001-12-27

Publication date

2006-06-06

2001-12-27 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2001-12-27 Publication of NO20016370L publication Critical patent/NO20016370L/no

2001-12-27 Publication of NO20016370D0 publication Critical patent/NO20016370D0/no

2006-06-06 Publication of NO321599B1 publication Critical patent/NO321599B1/no

Links

241000725643 Respiratory syncytial virus Species 0.000 title description 11
239000003112 inhibitor Substances 0.000 title 1
230000029812 viral genome replication Effects 0.000 title 1
239000000203 mixture Substances 0.000 claims description 143
150000001875 compounds Chemical class 0.000 claims description 132
239000002904 solvent Substances 0.000 claims description 124
239000001257 hydrogen Substances 0.000 claims description 48
229910052739 hydrogen Inorganic materials 0.000 claims description 48
238000006243 chemical reaction Methods 0.000 claims description 44
239000012442 inert solvent Substances 0.000 claims description 35
239000002253 acid Substances 0.000 claims description 33
239000002585 base Substances 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 29
150000002431 hydrogen Chemical group 0.000 claims description 28
125000001424 substituent group Chemical group 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 22
238000002360 preparation method Methods 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
239000003638 chemical reducing agent Substances 0.000 claims description 17
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
238000000034 method Methods 0.000 claims description 16
150000001412 amines Chemical group 0.000 claims description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
125000006239 protecting group Chemical group 0.000 claims description 13
239000003814 drug Substances 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 11
125000004076 pyridyl group Chemical group 0.000 claims description 11
238000011282 treatment Methods 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
150000001721 carbon Chemical group 0.000 claims description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
229910021529 ammonia Inorganic materials 0.000 claims description 7
239000003153 chemical reaction reagent Substances 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
238000005576 amination reaction Methods 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
231100000252 nontoxic Toxicity 0.000 claims description 5
230000003000 nontoxic effect Effects 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 4
IZCQDRVQVRENLX-UHFFFAOYSA-N dihydrate;trihydrochloride Chemical compound O.O.Cl.Cl.Cl IZCQDRVQVRENLX-UHFFFAOYSA-N 0.000 claims description 4
235000019253 formic acid Nutrition 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 3
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
239000012458 free base Substances 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
150000004684 trihydrates Chemical class 0.000 claims description 3
150000004683 dihydrates Chemical class 0.000 claims description 2
150000004682 monohydrates Chemical class 0.000 claims description 2
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
230000009466 transformation Effects 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 2
CUGZEDSDRBMZMY-UHFFFAOYSA-N trihydrate;hydrochloride Chemical compound O.O.O.Cl CUGZEDSDRBMZMY-UHFFFAOYSA-N 0.000 claims 2
CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims 1
NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 claims 1
238000000844 transformation Methods 0.000 claims 1
239000000543 intermediate Substances 0.000 description 220
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 82
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 79
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 66
239000000460 chlorine Substances 0.000 description 60
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
235000019441 ethanol Nutrition 0.000 description 50
-1 benzimidazole- and imidazopyridine-substituted piperidine Chemical class 0.000 description 46
239000012074 organic phase Substances 0.000 description 45
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 43
239000000243 solution Substances 0.000 description 43
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
239000003480 eluent Substances 0.000 description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
238000004440 column chromatography Methods 0.000 description 32
239000000741 silica gel Substances 0.000 description 32
229910002027 silica gel Inorganic materials 0.000 description 32
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
239000003054 catalyst Substances 0.000 description 26
239000002244 precipitate Substances 0.000 description 26
235000019439 ethyl acetate Nutrition 0.000 description 25
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
150000003254 radicals Chemical class 0.000 description 21
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 19
125000005843 halogen group Chemical group 0.000 description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 15
230000000840 anti-viral effect Effects 0.000 description 14
239000000706 filtrate Substances 0.000 description 14
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
229910000104 sodium hydride Inorganic materials 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
235000011114 ammonium hydroxide Nutrition 0.000 description 11
239000012312 sodium hydride Substances 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
125000004432 carbon atom Chemical group C* 0.000 description 10
229910052801 chlorine Inorganic materials 0.000 description 10
238000000746 purification Methods 0.000 description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
235000015320 potassium carbonate Nutrition 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
150000007513 acids Chemical class 0.000 description 8
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 8
239000003245 coal Substances 0.000 description 8
229940079593 drug Drugs 0.000 description 8
208000015181 infectious disease Diseases 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
229930195734 saturated hydrocarbon Natural products 0.000 description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
206010061603 Respiratory syncytial virus infection Diseases 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
231100000135 cytotoxicity Toxicity 0.000 description 7
230000003013 cytotoxicity Effects 0.000 description 7
239000012071 phase Substances 0.000 description 7
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
241000700605 Viruses Species 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
235000011181 potassium carbonates Nutrition 0.000 description 6
239000000725 suspension Substances 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
208000036142 Viral infection Diseases 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
239000002480 mineral oil Substances 0.000 description 5
235000010446 mineral oil Nutrition 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
239000007787 solid Substances 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
230000009385 viral infection Effects 0.000 description 5
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 4
241000711920 Human orthopneumovirus Species 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
239000007868 Raney catalyst Substances 0.000 description 4
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
229910000564 Raney nickel Inorganic materials 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
108010037444 diisopropylglutathione ester Proteins 0.000 description 4
125000004356 hydroxy functional group Chemical group O* 0.000 description 4
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
239000000843 powder Substances 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
125000006545 (C1-C9) alkyl group Chemical group 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000002835 absorbance Methods 0.000 description 3
238000003556 assay Methods 0.000 description 3
235000019400 benzoyl peroxide Nutrition 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
239000002775 capsule Substances 0.000 description 3
229950005499 carbon tetrachloride Drugs 0.000 description 3
238000010511 deprotection reaction Methods 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000004811 liquid chromatography Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
230000001590 oxidative effect Effects 0.000 description 3
150000002978 peroxides Chemical class 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 3
239000012453 solvate Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 description 2
OMIVCRYZSXDGAB-UHFFFAOYSA-N 1,4-butanediyl Chemical group [CH2]CC[CH2] OMIVCRYZSXDGAB-UHFFFAOYSA-N 0.000 description 2
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
XZXFPXRTQDBCKK-UHFFFAOYSA-N 2-methyl-5,6,7,8-tetrahydroquinolin-8-ol Chemical compound C1CCC(O)C2=NC(C)=CC=C21 XZXFPXRTQDBCKK-UHFFFAOYSA-N 0.000 description 2
SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
ANQHLLHMDDFZJO-UHFFFAOYSA-N 3-methoxy-2-methyl-5,6,7,8-tetrahydroquinoline Chemical compound C1CCCC2=C1C=C(OC)C(C)=N2 ANQHLLHMDDFZJO-UHFFFAOYSA-N 0.000 description 2
YQDGQEKUTLYWJU-UHFFFAOYSA-N 5,6,7,8-tetrahydroquinoline Chemical compound C1=CC=C2CCCCC2=N1 YQDGQEKUTLYWJU-UHFFFAOYSA-N 0.000 description 2
241000711895 Bovine orthopneumovirus Species 0.000 description 2
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
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239000012895 dilution Substances 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000009826 distribution Methods 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
241001493065 dsRNA viruses Species 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002085 enols Chemical class 0.000 description 1
ZJMSHBADPFAJSM-UHFFFAOYSA-N ethyl 2,3-dimethylquinoxaline-5-carboxylate Chemical compound CC1=C(C)N=C2C(C(=O)OCC)=CC=CC2=N1 ZJMSHBADPFAJSM-UHFFFAOYSA-N 0.000 description 1
MBLHOOLYFFEWSQ-UHFFFAOYSA-N ethyl 4-[[1-(6,7-dihydro-5h-cyclopenta[b]pyridin-7-yl)benzimidazol-2-yl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC1=NC2=CC=CC=C2N1C1C2=NC=CC=C2CC1 MBLHOOLYFFEWSQ-UHFFFAOYSA-N 0.000 description 1
LKKAWMNEPUOSKW-UHFFFAOYSA-N ethyl 4-isothiocyanatopiperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(N=C=S)CC1 LKKAWMNEPUOSKW-UHFFFAOYSA-N 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000013100 final test Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
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150000002334 glycols Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000009931 harmful effect Effects 0.000 description 1
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 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical class C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
150000005232 imidazopyridines Chemical class 0.000 description 1
229960001438 immunostimulant agent Drugs 0.000 description 1
239000003022 immunostimulating agent Substances 0.000 description 1
230000003308 immunostimulating effect Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
229940031551 inactivated vaccine Drugs 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229960001388 interferon-beta Drugs 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
XJTQJERLRPWUGL-UHFFFAOYSA-N iodomethylbenzene Chemical compound ICC1=CC=CC=C1 XJTQJERLRPWUGL-UHFFFAOYSA-N 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
231100000516 lung damage Toxicity 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
UODUKZSHCSAPBU-UHFFFAOYSA-N n-[1-(2-aminoethyl)piperidin-4-yl]-1-(quinolin-4-ylmethyl)benzimidazol-2-amine Chemical compound C1CN(CCN)CCC1NC1=NC2=CC=CC=C2N1CC1=CC=NC2=CC=CC=C12 UODUKZSHCSAPBU-UHFFFAOYSA-N 0.000 description 1
201000009240 nasopharyngitis Diseases 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940127073 nucleoside analogue Drugs 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229960000402 palivizumab Drugs 0.000 description 1
239000003961 penetration enhancing agent Substances 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
NCAIGTHBQTXTLR-UHFFFAOYSA-N phentermine hydrochloride Chemical compound [Cl-].CC(C)([NH3+])CC1=CC=CC=C1 NCAIGTHBQTXTLR-UHFFFAOYSA-N 0.000 description 1
238000000053 physical method Methods 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
239000004033 plastic Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
239000001294 propane Substances 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
SDRHNFVNECLICR-UHFFFAOYSA-N pyridin-2-amine tetrahydrochloride Chemical compound Cl.Cl.Cl.Cl.NC1=CC=CC=N1 SDRHNFVNECLICR-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
RZIPENSSTUBRAA-UHFFFAOYSA-N quinolin-6-ylmethanamine Chemical compound N1=CC=CC2=CC(CN)=CC=C21 RZIPENSSTUBRAA-UHFFFAOYSA-N 0.000 description 1
WPYJKGWLDJECQD-UHFFFAOYSA-N quinoline-2-carbaldehyde Chemical compound C1=CC=CC2=NC(C=O)=CC=C21 WPYJKGWLDJECQD-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
229960000329 ribavirin Drugs 0.000 description 1
HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 1
238000012216 screening Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
229960005137 succinic acid Drugs 0.000 description 1
235000000346 sugar Nutrition 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
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
231100000211 teratogenicity Toxicity 0.000 description 1
OSDUDPQWLGJWGL-UHFFFAOYSA-N tert-butyl 4-(1h-benzimidazol-2-ylamino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=NC2=CC=CC=C2N1 OSDUDPQWLGJWGL-UHFFFAOYSA-N 0.000 description 1
XQYZAZWHJNGKPK-UHFFFAOYSA-N tert-butyl n-[1-[4-[[1-(2-bromo-5,6,7,8-tetrahydroquinolin-8-yl)benzimidazol-2-yl]amino]piperidin-1-yl]-3-methylbutan-2-yl]carbamate Chemical compound C1CN(CC(C(C)C)NC(=O)OC(C)(C)C)CCC1NC1=NC2=CC=CC=C2N1C1C2=NC(Br)=CC=C2CCC1 XQYZAZWHJNGKPK-UHFFFAOYSA-N 0.000 description 1
MKCXQUIBDSPYFO-UHFFFAOYSA-N tert-butyl-(1-hydroxy-3-methylbutan-2-yl)carbamic acid Chemical compound CC(C)C(CO)N(C(O)=O)C(C)(C)C MKCXQUIBDSPYFO-UHFFFAOYSA-N 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
150000004685 tetrahydrates Chemical class 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- 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
- A61P31/14—Antivirals for RNA 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Virology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NO20016370A 1999-06-28 2001-12-27 Respiratorisk syncytialvirusreplikasjonsinhibitorer NO321599B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP99202089		1999-06-28
PCT/EP2000/005677 WO2001000615A1 (en)	1999-06-28	2000-06-20	Respiratory syncytial virus replication inhibitors

Publications (3)

Publication Number	Publication Date
NO20016370L NO20016370L (no)	2001-12-27
NO20016370D0 NO20016370D0 (no)	2001-12-27
NO321599B1 true NO321599B1 (no)	2006-06-06

Family

ID=8240374

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20016370A NO321599B1 (no)	1999-06-28	2001-12-27	Respiratorisk syncytialvirusreplikasjonsinhibitorer

Country Status (34)

Country	Link
US (2)	US7071192B1 (de)
EP (2)	EP1400519B1 (de)
JP (1)	JP2003503403A (de)
KR (1)	KR100731273B1 (de)
CN (1)	CN1171887C (de)
AR (1)	AR024495A1 (de)
AT (2)	ATE259796T1 (de)
AU (1)	AU774829B2 (de)
BG (1)	BG65373B1 (de)
BR (1)	BR0011997A (de)
CA (1)	CA2376785A1 (de)
CZ (1)	CZ20014573A3 (de)
DE (2)	DE60008382T2 (de)
DK (1)	DK1196410T3 (de)
EA (1)	EA004746B1 (de)
EE (1)	EE04592B1 (de)
ES (2)	ES2215670T3 (de)
HK (1)	HK1045998B (de)
HR (2)	HRP20010934A2 (de)
HU (1)	HUP0201789A3 (de)
IL (2)	IL147328A0 (de)
MX (1)	MXPA02000117A (de)
MY (1)	MY129810A (de)
NO (1)	NO321599B1 (de)
NZ (1)	NZ515392A (de)
PL (1)	PL200694B1 (de)
PT (1)	PT1196410E (de)
SI (1)	SI1196410T1 (de)
SK (1)	SK18952001A3 (de)
TR (2)	TR200103805T2 (de)
TW (1)	TWI267513B (de)
UA (1)	UA75866C2 (de)
WO (1)	WO2001000615A1 (de)
ZA (1)	ZA200110473B (de)

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RU2263674C2 (ru) *	2000-01-17	2005-11-10	Тейдзин Лимитед	Бензимидазольное производное, ингибитор человеческой химазы, терапевтический агент и фармацевтическая композиция на его основе
US6489338B2 (en)	2000-06-13	2002-12-03	Bristol-Myers Squibb Company	Imidazopyridine and imidazopyrimidine antiviral agents
PE20020506A1 (es)	2000-08-22	2002-07-09	Glaxo Group Ltd	Derivados de pirazol fusionados como inhibidores de la proteina cinasa
US6506738B1 (en)	2000-09-27	2003-01-14	Bristol-Myers Squibb Company	Benzimidazolone antiviral agents
ATE301653T1 (de)	2000-12-15	2005-08-15	Glaxo Group Ltd	Pyrazolopyridine
WO2002048148A2 (en)	2000-12-15	2002-06-20	Glaxo Group Limited	Pyrazolopyridine derivatives
US6774134B2 (en)	2000-12-20	2004-08-10	Bristol-Myers Squibb Company	Heterocyclic substituted 2-methyl-benzimidazole antiviral agents
JP2004529119A (ja)	2001-03-08	2004-09-24	スミスクラインビーチャムコーポレーション	ピラゾロピリジン誘導体
WO2002078700A1 (en)	2001-03-30	2002-10-10	Smithkline Beecham Corporation	Pyralopyridines, process for their preparation and use as therapteutic compounds
US7141569B2 (en)	2001-04-10	2006-11-28	Smithkline Beecham Corporation	Antiviral pyrazolopyridine compounds
ATE296826T1 (de)	2001-04-27	2005-06-15	Smithkline Beecham Corp	Pyrazolo(1,5)pyridinderivate
US7030150B2 (en)	2001-05-11	2006-04-18	Trimeris, Inc.	Benzimidazole compounds and antiviral uses thereof
JP2005500315A (ja)	2001-06-21	2005-01-06	スミスクラインビーチャムコーポレーション	ヘルペスウイルス感染の予防および治療用イミダゾ［１，２−ａ］ピリジン誘導体
EP1432712B1 (de)	2001-10-05	2006-05-17	SmithKline Beecham Corporation	Imidazopyridinderivate zur verwendung bei der behandlung von herpes-vireninfektion
US6919331B2 (en)	2001-12-10	2005-07-19	Bristol-Myers Squibb Company	Substituted 2-methyl-benzimidazole respiratory syncytial virus antiviral agents
WO2003050120A1 (en)	2001-12-11	2003-06-19	Smithkline Beecham Corporation	Pyrazolo-pyridine derivatives as antiherpes agents
US7244847B2 (en) *	2002-02-06	2007-07-17	Isis Pharmaceuticals, Inc.	Benzimidazole compounds
WO2004014316A2 (en)	2002-08-09	2004-02-19	Viropharma Incorporated	Compounds, compositions and methods for treating or preventing pneumovirus infection and associated diseases
CA2495245A1 (en)	2002-08-09	2004-02-19	Viropharma Incorporated	Compounds, compositions and methods for treating or preventing pneumovirus infection and associated diseases
JP2006504728A (ja)	2002-10-03	2006-02-09	スミスクラインビーチャムコーポレーション	ピラソロピリジン誘導体系治療用化合物
US7323567B2 (en)	2003-10-30	2008-01-29	Boehringer Ingelheim (Canada) Ltd.	RSV polymerase inhibitors
CN1914196B (zh) *	2003-12-18	2012-01-25	泰博特克药品有限公司	作为呼吸道合胞病毒复制抑制剂的5-或6-取代的苯并咪唑衍生物
US7355051B2 (en) *	2003-12-18	2008-04-08	Tibotec Pharmaceuticals	Piperdine-amino-benzimidazole derivatives as inhibitors of respiratory syncytial virus replication
RU2332414C2 (ru) *	2003-12-18	2008-08-27	Тиботек Фармасьютикалз Лтд.	Производные аминобензимидазолов в качестве ингибиторов репликации респираторного синцитиального вируса
CN1894236B (zh) *	2003-12-18	2011-08-17	泰博特克药品有限公司	作为呼吸道合胞病毒复制抑制剂的氨基-苯并咪唑类衍生物
AR046959A1 (es) *	2003-12-18	2006-01-04	Tibotec Pharm Ltd	Morfolinilo que contiene bencimidazoles como inhibidores de la replicacion del virus sincitial respiratorio
NZ547796A (en) *	2003-12-18	2009-04-30	Tibotec Pharm Ltd	Aminobenzimidazoles and benzimidazoles as inhibitors of respiratory syncytial virus replication
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2000
- 2000-06-20 EP EP03102464A patent/EP1400519B1/de not_active Expired - Lifetime
- 2000-06-20 ES ES00936899T patent/ES2215670T3/es not_active Expired - Lifetime
- 2000-06-20 EA EA200200086A patent/EA004746B1/ru not_active IP Right Cessation
- 2000-06-20 DE DE60008382T patent/DE60008382T2/de not_active Expired - Fee Related
- 2000-06-20 DE DE60033859T patent/DE60033859T2/de not_active Expired - Fee Related
- 2000-06-20 AT AT00936899T patent/ATE259796T1/de not_active IP Right Cessation
- 2000-06-20 SI SI200030358T patent/SI1196410T1/xx unknown
- 2000-06-20 TR TR2001/03805T patent/TR200103805T2/xx unknown
- 2000-06-20 CA CA002376785A patent/CA2376785A1/en not_active Abandoned
- 2000-06-20 BR BR0011997-0A patent/BR0011997A/pt not_active Application Discontinuation
- 2000-06-20 PL PL352385A patent/PL200694B1/pl not_active IP Right Cessation
- 2000-06-20 NZ NZ515392A patent/NZ515392A/xx unknown
- 2000-06-20 EP EP00936899A patent/EP1196410B1/de not_active Expired - Lifetime
- 2000-06-20 CZ CZ20014573A patent/CZ20014573A3/cs unknown
- 2000-06-20 CN CNB008095302A patent/CN1171887C/zh not_active Expired - Fee Related
- 2000-06-20 MX MXPA02000117A patent/MXPA02000117A/es active IP Right Grant
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- 2000-06-20 AT AT03102464T patent/ATE356121T1/de not_active IP Right Cessation
- 2000-06-20 KR KR1020017015284A patent/KR100731273B1/ko not_active IP Right Cessation
- 2000-06-20 ES ES03102464T patent/ES2283716T3/es not_active Expired - Lifetime
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- 2000-06-20 AU AU52222/00A patent/AU774829B2/en not_active Ceased
- 2000-06-20 JP JP2001507023A patent/JP2003503403A/ja not_active Withdrawn
- 2000-06-20 TR TR2005/00707T patent/TR200500707T2/xx unknown
- 2000-06-20 UA UA2002010361A patent/UA75866C2/uk unknown
- 2000-06-20 DK DK00936899T patent/DK1196410T3/da active
- 2000-06-20 WO PCT/EP2000/005677 patent/WO2001000615A1/en active Application Filing
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2001
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- 2001-12-27 NO NO20016370A patent/NO321599B1/no unknown
2002
- 2002-01-08 BG BG106288A patent/BG65373B1/bg unknown
- 2002-10-21 HK HK02107623.8A patent/HK1045998B/zh not_active IP Right Cessation
2005
- 2005-10-11 US US11/247,392 patent/US7407969B2/en not_active Expired - Fee Related
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Also Published As

Publication number	Publication date
ATE356121T1 (de)	2007-03-15
BR0011997A (pt)	2002-03-05
ATE259796T1 (de)	2004-03-15
HRP20080390A2 (en)	2008-12-31
EP1400519A1 (de)	2004-03-24
KR100731273B1 (ko)	2007-06-21
AU774829B2 (en)	2004-07-08
KR20020000815A (ko)	2002-01-05
ES2283716T3 (es)	2007-11-01
UA75866C2 (en)	2006-06-15
PL200694B1 (pl)	2009-01-30
EE200100694A (et)	2003-02-17
TR200103805T2 (tr)	2002-06-21
DK1196410T3 (da)	2004-06-28
AU5222200A (en)	2001-01-31
TR200500707T2 (tr)	2005-04-21
US7071192B1 (en)	2006-07-04
CN1358182A (zh)	2002-07-10
WO2001000615A1 (en)	2001-01-04
HUP0201789A3 (en)	2003-12-29
MY129810A (en)	2007-05-31
HUP0201789A2 (hu)	2002-11-28
US7407969B2 (en)	2008-08-05
US20060058309A1 (en)	2006-03-16
CZ20014573A3 (cs)	2002-05-15
AR024495A1 (es)	2002-10-02
EE04592B1 (et)	2006-02-15
NO20016370L (no)	2001-12-27
TWI267513B (en)	2006-12-01
NZ515392A (en)	2004-03-26
DE60008382T2 (de)	2004-12-02
EP1196410B1 (de)	2004-02-18
HK1045998A1 (en)	2002-12-20
PL352385A1 (en)	2003-08-25
SI1196410T1 (en)	2004-08-31
DE60008382D1 (en)	2004-03-25
BG106288A (en)	2002-10-31
CN1171887C (zh)	2004-10-20
JP2003503403A (ja)	2003-01-28
NO20016370D0 (no)	2001-12-27
MXPA02000117A (es)	2002-07-02
CA2376785A1 (en)	2001-01-04
DE60033859T2 (de)	2007-11-08
ES2215670T3 (es)	2004-10-16
DE60033859D1 (de)	2007-04-19
EA200200086A1 (ru)	2002-06-27
EP1196410A1 (de)	2002-04-17
EP1400519B1 (de)	2007-03-07
ZA200110473B (en)	2003-03-20
HK1045998B (zh)	2005-06-03
BG65373B1 (bg)	2008-04-30
SK18952001A3 (sk)	2002-11-06
IL147328A (en)	2007-06-03
WO2001000615A8 (en)	2002-01-10
HRP20010934A2 (en)	2003-06-30
IL147328A0 (en)	2002-08-14
EA004746B1 (ru)	2004-08-26
PT1196410E (pt)	2004-07-30

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US10501445B2 (en)	2019-12-10	Quinoxalinones and dihydroquinoxalinones as respiratory syncytial virus antiviral agents
MXPA02000112A (es)	2002-07-02	Inhibidores de la replicacion del virus sincitial respiratorio.