NO320703B1 - Nye ribose-substituerte aromatiske amider, fremgangsmate for deres fremstilling og farmasoytisk preparat inneholdende disse. - Google Patents

Nye ribose-substituerte aromatiske amider, fremgangsmate for deres fremstilling og farmasoytisk preparat inneholdende disse. Download PDF

Info

Publication number: NO320703B1
Authority: NO; Norway
Prior art keywords: methyl; denotes; formula; compounds; radical
Prior art date: 1999-04-19

Application number

NO20015058A

Other languages

English (en)

Norwegian (no)

Other versions

NO20015058L (no

NO20015058D0 (no

Inventor

Michel Klich

Branislav Musicki

Jacques Demassey

Original Assignee

Aventis Pharma Sa

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.)

1999-04-19

Filing date

2001-10-18

Publication date

2006-01-16

2001-10-18 Application filed by Aventis Pharma Sa filed Critical Aventis Pharma Sa

2001-10-18 Publication of NO20015058D0 publication Critical patent/NO20015058D0/no

2001-12-17 Publication of NO20015058L publication Critical patent/NO20015058L/no

2006-01-16 Publication of NO320703B1 publication Critical patent/NO320703B1/no

Links

238000000034 method Methods 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title description 21
150000008430 aromatic amides Chemical class 0.000 title description 2
239000008194 pharmaceutical composition Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 61
-1 alkyl radical Chemical class 0.000 claims description 34
125000004432 carbon atom Chemical group C* 0.000 claims description 21
125000005843 halogen group Chemical group 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
150000003254 radicals Chemical class 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000000825 pharmaceutical preparation Substances 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
BQOWUDKEXDCGQS-UHFFFAOYSA-N [CH]1CCCC1 Chemical compound [CH]1CCCC1 BQOWUDKEXDCGQS-UHFFFAOYSA-N 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 177
239000000047 product Substances 0.000 description 139
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 97
239000000203 mixture Substances 0.000 description 92
239000000243 solution Substances 0.000 description 69
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 50
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
239000011541 reaction mixture Substances 0.000 description 43
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 26
238000003756 stirring Methods 0.000 description 26
239000000377 silicon dioxide Substances 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
238000001914 filtration Methods 0.000 description 22
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
238000001035 drying Methods 0.000 description 21
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
238000000605 extraction Methods 0.000 description 17
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 15
239000007864 aqueous solution Substances 0.000 description 14
238000004587 chromatography analysis Methods 0.000 description 14
238000001704 evaporation Methods 0.000 description 14
230000008020 evaporation Effects 0.000 description 14
239000012074 organic phase Substances 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
238000005406 washing Methods 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
235000019441 ethanol Nutrition 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
239000001488 sodium phosphate Substances 0.000 description 7
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
229910000403 monosodium phosphate Inorganic materials 0.000 description 6
235000019799 monosodium phosphate Nutrition 0.000 description 6
238000000926 separation method Methods 0.000 description 6
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 6
229910000162 sodium phosphate Inorganic materials 0.000 description 6
239000002904 solvent Substances 0.000 description 6
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 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
239000008346 aqueous phase Substances 0.000 description 5
125000004122 cyclic group Chemical group 0.000 description 5
238000010790 dilution Methods 0.000 description 5
239000012895 dilution Substances 0.000 description 5
GFHFNPNDTKMWNE-UHFFFAOYSA-N prop-2-ynoxycarbamic acid Chemical compound OC(=O)NOCC#C GFHFNPNDTKMWNE-UHFFFAOYSA-N 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
235000011008 sodium phosphates Nutrition 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 5
125000004518 1,2,5-thiadiazol-3-yl group Chemical group S1N=C(C=N1)* 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
238000010908 decantation Methods 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
239000001632 sodium acetate Substances 0.000 description 4
235000017281 sodium acetate Nutrition 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
QJIHWLIDFLBEKN-UHFFFAOYSA-N 4,7-dihydroxy-8-methyl-3-phenyldiazenylchromen-2-one Chemical compound O=C1OC=2C(C)=C(O)C=CC=2C(O)=C1N=NC1=CC=CC=C1 QJIHWLIDFLBEKN-UHFFFAOYSA-N 0.000 description 3
206010002383 Angina Pectoris Diseases 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 3
229910000397 disodium phosphate Inorganic materials 0.000 description 3
235000019800 disodium phosphate Nutrition 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
BXXWFOGWXLJPPA-UHFFFAOYSA-N 2,3-dibromobutane Chemical compound CC(Br)C(C)Br BXXWFOGWXLJPPA-UHFFFAOYSA-N 0.000 description 2
KSNGPGUKUNMQPA-UHFFFAOYSA-N 4-benzhydryloxy-7-hydroxy-8-methylchromen-2-one Chemical compound C=1C(=O)OC=2C(C)=C(O)C=CC=2C=1OC(C=1C=CC=CC=1)C1=CC=CC=C1 KSNGPGUKUNMQPA-UHFFFAOYSA-N 0.000 description 2
229960000549 4-dimethylaminophenol Drugs 0.000 description 2
XHOHPTVAJZESEZ-UHFFFAOYSA-N 4-hydroxy-8-methyl-7-(oxan-2-yl)chromen-2-one Chemical compound C1=CC=2C(O)=CC(=O)OC=2C(C)=C1C1CCCCO1 XHOHPTVAJZESEZ-UHFFFAOYSA-N 0.000 description 2
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
241000295644 Staphylococcaceae Species 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
229910000024 caesium carbonate Inorganic materials 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
ZNOSXPWPYGLEFO-UHFFFAOYSA-N chloroform cyanide Chemical compound ClC(Cl)Cl.[C-]#N ZNOSXPWPYGLEFO-UHFFFAOYSA-N 0.000 description 2
239000013078 crystal Substances 0.000 description 2
JHFINHOBWIGQHJ-UHFFFAOYSA-N cyclopropylcarbamic acid Chemical compound OC(=O)NC1CC1 JHFINHOBWIGQHJ-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000012678 infectious agent Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 2
229910001486 lithium perchlorate Inorganic materials 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
PNNRZXFUPQQZSO-UHFFFAOYSA-N pyran Chemical compound [CH]1OC=CC=C1 PNNRZXFUPQQZSO-UHFFFAOYSA-N 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
229940095064 tartrate Drugs 0.000 description 2
238000002604 ultrasonography Methods 0.000 description 2
JHZJVBXDHGYVLJ-CUWOBHIPSA-N (3r,4s,5r)-5-methoxy-6,6-dimethyloxane-2,3,4-triol Chemical compound CO[C@@H]1[C@@H](O)[C@@H](O)C(O)OC1(C)C JHZJVBXDHGYVLJ-CUWOBHIPSA-N 0.000 description 1
WHXSMMKQMYFTQS-BJUDXGSMSA-N (6Li)Lithium Chemical compound [6Li] WHXSMMKQMYFTQS-BJUDXGSMSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 1
XBRTWUIFHFTUKK-UHFFFAOYSA-N 2-(pyridin-2-ylmethoxy)acetic acid Chemical compound OC(=O)COCC1=CC=CC=N1 XBRTWUIFHFTUKK-UHFFFAOYSA-N 0.000 description 1
VIRWKAJWTKAIMA-UHFFFAOYSA-N 2-chloroethyl acetate Chemical compound CC(=O)OCCCl VIRWKAJWTKAIMA-UHFFFAOYSA-N 0.000 description 1
YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
NOGDCTMYKWGZPZ-UHFFFAOYSA-N 2-methoxyiminopropanoic acid Chemical compound CON=C(C)C(O)=O NOGDCTMYKWGZPZ-UHFFFAOYSA-N 0.000 description 1
DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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239000008365 aqueous carrier Substances 0.000 description 1
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239000012298 atmosphere Substances 0.000 description 1
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230000003115 biocidal effect Effects 0.000 description 1
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239000012267 brine Substances 0.000 description 1
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238000001816 cooling Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
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KBLZFQBDODEHJH-UHFFFAOYSA-N dibutylalumane Chemical compound C(CCC)[AlH]CCCC KBLZFQBDODEHJH-UHFFFAOYSA-N 0.000 description 1
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150000002367 halogens Chemical class 0.000 description 1
239000003906 humectant Substances 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
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230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
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239000011630 iodine Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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239000008101 lactose Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
230000003211 malignant effect Effects 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000017066 negative regulation of growth Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
CEFBXYRCGUITCZ-UHFFFAOYSA-N o-prop-2-ynylhydroxylamine;hydrochloride Chemical compound Cl.NOCC#C CEFBXYRCGUITCZ-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
GPTFURBXHJWNHR-UHFFFAOYSA-N protopine Chemical compound C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
230000001698 pyrogenic effect Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
201000009890 sinusitis Diseases 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/075—Benzo[b]pyran-2-ones
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
- 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
- A61P31/04—Antibacterial agents
- 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
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biochemistry (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Virology (AREA)
Bioinformatics & Cheminformatics (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Pulmonology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

NO20015058A 1999-04-19 2001-10-18 Nye ribose-substituerte aromatiske amider, fremgangsmate for deres fremstilling og farmasoytisk preparat inneholdende disse. NO320703B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9904866A FR2792320B1 (fr)	1999-04-19	1999-04-19	Nouveaux amides aromatiques substitues par un ribose, leur procede de preparation et leur application comme medicaments
PCT/FR2000/000999 WO2000063222A2 (fr)	1999-04-19	2000-04-18	Nouveaux amides aromatiques substitues par un ribose, leur procede de preparation et leur application comme medicaments

Publications (3)

Publication Number	Publication Date
NO20015058D0 NO20015058D0 (no)	2001-10-18
NO20015058L NO20015058L (no)	2001-12-17
NO320703B1 true NO320703B1 (no)	2006-01-16

Family

ID=9544554

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20015058A NO320703B1 (no)	1999-04-19	2001-10-18	Nye ribose-substituerte aromatiske amider, fremgangsmate for deres fremstilling og farmasoytisk preparat inneholdende disse.

Country Status (24)

Country	Link
US (1)	US6579902B1 (de)
EP (1)	EP1173455A2 (de)
JP (1)	JP2002542253A (de)
KR (1)	KR100693258B1 (de)
CN (1)	CN1213055C (de)
AP (1)	AP2001002312A0 (de)
AU (1)	AU769514B2 (de)
CA (1)	CA2363945A1 (de)
CZ (1)	CZ20013708A3 (de)
EA (1)	EA004304B1 (de)
FR (1)	FR2792320B1 (de)
HK (1)	HK1046690B (de)
HU (1)	HUP0200778A3 (de)
ID (1)	ID30562A (de)
IL (1)	IL146018A0 (de)
NO (1)	NO320703B1 (de)
NZ (1)	NZ515108A (de)
PL (1)	PL354192A1 (de)
SK (1)	SK14842001A3 (de)
TR (1)	TR200103009T2 (de)
UA (1)	UA72919C2 (de)
WO (1)	WO2000063222A2 (de)
YU (1)	YU80301A (de)
ZA (1)	ZA200108627B (de)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2844273B1 (fr) *	2002-09-05	2008-04-04	Aventis Pharma Sa	Nouveaux composes heterocycliques, procede et intermediaires de preparation et utilisation comme medicament, notamment comme inhibiteurs de beta-lactamases et anti-bacteriens.
US7439253B2 (en) *	2002-12-06	2008-10-21	Novexel	Heterocyclic compounds, their preparation and their use as medicaments, in particular as antibacterials and beta-lactamase inhibitors
KR100649357B1 (ko) *	2004-05-04	2006-11-24	제일약품주식회사	항염증 활성을 갖는 크로멘-2-온 모핵 히드록사민 산유도체, 이의 제조방법 및 이를 포함하는 염증 질환의치료를 위한 조성물
US7622451B2 (en) *	2004-11-03	2009-11-24	University Of Kansas	Novobiocin analogues as neuroprotective agents and in the treatment of autoimmune disorders
AU2005301957B2 (en) *	2004-11-03	2012-02-23	Department Of Health And Human Services	Novobiocin analogues as anticancer agents
US9120774B2 (en)	2004-11-03	2015-09-01	University Of Kansas	Novobiocin analogues having modified sugar moieties
US8212011B2 (en) *	2004-11-03	2012-07-03	University Of Kansas	Novobiocin analogues
US8212012B2 (en) *	2004-11-03	2012-07-03	University Of Kansas	Novobiocin analogues having modified sugar moieties
US7960353B2 (en) *	2007-05-10	2011-06-14	University Of Kansas	Novobiocin analogues as neuroprotective agents and in the treatment of autoimmune disorders
WO2010014617A1 (en) *	2008-07-28	2010-02-04	University Of Kansas	Heat shock protein 90 inhibitor dosing methods
US20110082098A1 (en) *	2009-09-30	2011-04-07	University Of Kansas	Novobiocin analogues and treatment of polycystic kidney disease
MX2025007723A (es)	2018-05-14	2025-08-01	Reata Pharmaceuticals Inc	Biarilamidas con grupos de azucar modificados para el tratamiento de enfermedades asociadas con la trayectoria de la proteina de choque de calor

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3652536A (en) *	1969-06-02	1972-03-28	Upjohn Co	Novenamine compounds and derivatives
US3890297A (en) *	1973-03-29	1975-06-17	Upjohn Co	Process for n-acylating novenamine

1999
- 1999-04-19 FR FR9904866A patent/FR2792320B1/fr not_active Expired - Fee Related
2000
- 2000-04-18 NZ NZ515108A patent/NZ515108A/xx unknown
- 2000-04-18 AU AU41256/00A patent/AU769514B2/en not_active Ceased
- 2000-04-18 EP EP00920823A patent/EP1173455A2/de not_active Withdrawn
- 2000-04-18 ID IDW00200102505A patent/ID30562A/id unknown
- 2000-04-18 AP APAP/P/2001/002312A patent/AP2001002312A0/en unknown
- 2000-04-18 HU HU0200778A patent/HUP0200778A3/hu unknown
- 2000-04-18 YU YU80301A patent/YU80301A/sh unknown
- 2000-04-18 JP JP2000612312A patent/JP2002542253A/ja active Pending
- 2000-04-18 US US09/980,728 patent/US6579902B1/en not_active Expired - Fee Related
- 2000-04-18 WO PCT/FR2000/000999 patent/WO2000063222A2/fr not_active Ceased
- 2000-04-18 TR TR2001/03009T patent/TR200103009T2/xx unknown
- 2000-04-18 CA CA002363945A patent/CA2363945A1/fr not_active Abandoned
- 2000-04-18 UA UA2001117895A patent/UA72919C2/uk unknown
- 2000-04-18 HK HK02108190.9A patent/HK1046690B/zh not_active IP Right Cessation
- 2000-04-18 IL IL14601800A patent/IL146018A0/xx unknown
- 2000-04-18 SK SK1484-2001A patent/SK14842001A3/sk unknown
- 2000-04-18 CZ CZ20013708A patent/CZ20013708A3/cs unknown
- 2000-04-18 CN CNB008091900A patent/CN1213055C/zh not_active Expired - Fee Related
- 2000-04-18 EA EA200101100A patent/EA004304B1/ru not_active IP Right Cessation
- 2000-04-18 PL PL00354192A patent/PL354192A1/xx not_active Application Discontinuation
- 2000-04-18 KR KR1020017013340A patent/KR100693258B1/ko not_active Expired - Fee Related
2001
- 2001-10-18 NO NO20015058A patent/NO320703B1/no unknown
- 2001-10-19 ZA ZA200108627A patent/ZA200108627B/en unknown

Also Published As

Publication number	Publication date
EA200101100A1 (ru)	2002-04-25
SK14842001A3 (sk)	2003-05-02
HK1046690B (zh)	2006-03-10
WO2000063222A2 (fr)	2000-10-26
YU80301A (sh)	2005-07-19
UA72919C2 (uk)	2005-05-16
JP2002542253A (ja)	2002-12-10
FR2792320A1 (fr)	2000-10-20
CZ20013708A3 (cs)	2002-04-17
WO2000063222A3 (fr)	2001-05-31
NO20015058L (no)	2001-12-17
ZA200108627B (en)	2002-10-21
AU769514B2 (en)	2004-01-29
HUP0200778A3 (en)	2003-03-28
CN1213055C (zh)	2005-08-03
KR100693258B1 (ko)	2007-03-13
PL354192A1 (en)	2003-12-29
FR2792320B1 (fr)	2003-05-09
IL146018A0 (en)	2002-07-25
CA2363945A1 (fr)	2000-10-26
ID30562A (id)	2001-12-20
CN1357001A (zh)	2002-07-03
TR200103009T2 (tr)	2002-05-21
US6579902B1 (en)	2003-06-17
EA004304B1 (ru)	2004-02-26
KR20020008155A (ko)	2002-01-29
NZ515108A (en)	2004-01-30
HK1046690A1 (en)	2003-01-24
AU4125600A (en)	2000-11-02
AP2001002312A0 (en)	2001-12-31
EP1173455A2 (de)	2002-01-23
HUP0200778A2 (hu)	2002-07-29
NO20015058D0 (no)	2001-10-18

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