JP4342304B2 - チアゾリルアミドの局所適用 - Google Patents
チアゾリルアミドの局所適用 Download PDFInfo
- Publication number
- JP4342304B2 JP4342304B2 JP2003506904A JP2003506904A JP4342304B2 JP 4342304 B2 JP4342304 B2 JP 4342304B2 JP 2003506904 A JP2003506904 A JP 2003506904A JP 2003506904 A JP2003506904 A JP 2003506904A JP 4342304 B2 JP4342304 B2 JP 4342304B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- mono
- halo
- het
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000000699 topical effect Effects 0.000 title claims description 22
- 239000000203 mixture Substances 0.000 claims abstract description 60
- -1 3,4-methylenedioxyphenyl Chemical group 0.000 claims abstract description 56
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 52
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 33
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 33
- 238000011282 treatment Methods 0.000 claims abstract description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 238000009472 formulation Methods 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 16
- 239000000725 suspension Substances 0.000 claims description 14
- 239000000499 gel Substances 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000002674 ointment Substances 0.000 claims description 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 239000006071 cream Substances 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 239000007921 spray Substances 0.000 claims description 4
- 239000000839 emulsion Substances 0.000 claims description 3
- 239000006260 foam Substances 0.000 claims description 3
- 239000006210 lotion Substances 0.000 claims description 2
- 239000006072 paste Substances 0.000 claims description 2
- DEFLNOSTNCSZRB-IDTAVKCVSA-N 9-[(2r,3r,4r,5r)-3,4-dimethoxy-5-(methoxymethyl)oxolan-2-yl]-n-methoxypurin-6-amine Chemical compound CO[C@@H]1[C@H](OC)[C@@H](COC)O[C@H]1N1C2=NC=NC(NOC)=C2N=C1 DEFLNOSTNCSZRB-IDTAVKCVSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940098458 powder spray Drugs 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 abstract description 27
- 125000005843 halogen group Chemical group 0.000 abstract description 18
- 125000003118 aryl group Chemical group 0.000 abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 abstract description 15
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 14
- 125000002252 acyl group Chemical group 0.000 abstract description 13
- 229920006395 saturated elastomer Polymers 0.000 abstract description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 12
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 8
- 125000002950 monocyclic group Chemical group 0.000 abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 7
- 125000004414 alkyl thio group Chemical group 0.000 abstract description 6
- IVZKZONQVYTCKC-UHFFFAOYSA-N bay 57-1293 Chemical compound N=1C(C)=C(S(N)(=O)=O)SC=1N(C)C(=O)CC(C=C1)=CC=C1C1=CC=CC=N1 IVZKZONQVYTCKC-UHFFFAOYSA-N 0.000 abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 abstract description 6
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 abstract description 5
- HJCUTNIGJHJGCF-UHFFFAOYSA-N 9,10-dihydroacridine Chemical compound C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 abstract description 4
- 241000700588 Human alphaherpesvirus 1 Species 0.000 abstract description 4
- 241000699670 Mus sp. Species 0.000 abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 abstract description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 abstract description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003889 eye drop Substances 0.000 abstract description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract description 3
- 229940068196 placebo Drugs 0.000 abstract description 3
- 239000000902 placebo Substances 0.000 abstract description 3
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 abstract description 2
- 229960004150 aciclovir Drugs 0.000 abstract description 2
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 4
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 abstract 4
- 125000001188 haloalkyl group Chemical group 0.000 abstract 4
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 abstract 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 abstract 3
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 2
- 125000005332 alkyl sulfoxy group Chemical group 0.000 abstract 2
- 125000002619 bicyclic group Chemical group 0.000 abstract 2
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 2
- 125000005389 trialkylsiloxy group Chemical group 0.000 abstract 2
- SZXURXLGTQZFES-UHFFFAOYSA-N 2-phenyl-n-(5-sulfamoyl-1,3-thiazol-2-yl)acetamide Chemical class S1C(S(=O)(=O)N)=CN=C1NC(=O)CC1=CC=CC=C1 SZXURXLGTQZFES-UHFFFAOYSA-N 0.000 abstract 1
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 235000001014 amino acid Nutrition 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 229940012356 eye drops Drugs 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 230000010534 mechanism of action Effects 0.000 abstract 1
- 150000007979 thiazole derivatives Chemical class 0.000 abstract 1
- 239000012873 virucide Substances 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 65
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
- 229910052736 halogen Inorganic materials 0.000 description 35
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 32
- 239000004480 active ingredient Substances 0.000 description 28
- 150000002367 halogens Chemical class 0.000 description 26
- 241001465754 Metazoa Species 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 208000015181 infectious disease Diseases 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- 239000002202 Polyethylene glycol Substances 0.000 description 19
- 125000004432 carbon atom Chemical group C* 0.000 description 19
- 229920001223 polyethylene glycol Polymers 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 230000001575 pathological effect Effects 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 8
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 125000001153 fluoro group Chemical group F* 0.000 description 8
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 7
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 6
- LVLDBZCFWNSVLJ-UHFFFAOYSA-N 4-methyl-2-(methylamino)-1,3-thiazole-5-sulfonamide Chemical compound CNC1=NC(C)=C(S(N)(=O)=O)S1 LVLDBZCFWNSVLJ-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000001186 cumulative effect Effects 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 208000007514 Herpes zoster Diseases 0.000 description 5
- 229920001030 Polyethylene Glycol 4000 Polymers 0.000 description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 description 5
- 235000008206 alpha-amino acids Nutrition 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 210000001508 eye Anatomy 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 description 4
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
- 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 4
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000701074 Human alphaherpesvirus 2 Species 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000004043 oxo group Chemical group O=* 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000009885 systemic effect Effects 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
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- HSOKOZJRZALFLQ-UHFFFAOYSA-N 2-[4-(2-fluorophenyl)phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C1=CC=CC=C1F HSOKOZJRZALFLQ-UHFFFAOYSA-N 0.000 description 3
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical group O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 3
- 0 Cc1c(*)nc(N(*)C(C(*)(*)*)=O)[s]1 Chemical compound Cc1c(*)nc(N(*)C(C(*)(*)*)=O)[s]1 0.000 description 3
- 208000009889 Herpes Simplex Diseases 0.000 description 3
- 206010019973 Herpes virus infection Diseases 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- QRZAKQDHEVVFRX-UHFFFAOYSA-N biphenyl-4-ylacetic acid Chemical class C1=CC(CC(=O)O)=CC=C1C1=CC=CC=C1 QRZAKQDHEVVFRX-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 210000005252 bulbus oculi Anatomy 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 229940107931 zovirax Drugs 0.000 description 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 2
- SCZNXLWKYFICFV-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-b]diazepine Chemical compound C1CCCNN2CCCC=C21 SCZNXLWKYFICFV-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- 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
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- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
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- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
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- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dermatology (AREA)
- Ophthalmology & Optometry (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Oncology (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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| DE10129714A DE10129714A1 (de) | 2001-06-22 | 2001-06-22 | Topische Anwendung von Thiazolylamiden |
| PCT/EP2002/006327 WO2003000259A1 (de) | 2001-06-22 | 2002-06-10 | Topische anwendung von thiazolylamiden |
Publications (3)
| Publication Number | Publication Date |
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| JP2004534818A JP2004534818A (ja) | 2004-11-18 |
| JP2004534818A5 JP2004534818A5 (https=) | 2006-01-05 |
| JP4342304B2 true JP4342304B2 (ja) | 2009-10-14 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2003506904A Expired - Lifetime JP4342304B2 (ja) | 2001-06-22 | 2002-06-10 | チアゾリルアミドの局所適用 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7883713B2 (https=) |
| EP (2) | EP1629842B1 (https=) |
| JP (1) | JP4342304B2 (https=) |
| KR (1) | KR100899491B1 (https=) |
| CN (1) | CN1535149B (https=) |
| AT (2) | ATE320253T1 (https=) |
| AU (1) | AU2002345023B2 (https=) |
| BR (1) | BRPI0210601B8 (https=) |
| CA (1) | CA2451552C (https=) |
| DE (3) | DE10129714A1 (https=) |
| DK (2) | DK1629842T3 (https=) |
| ES (2) | ES2341778T3 (https=) |
| IL (1) | IL159258A0 (https=) |
| MX (1) | MXPA03011518A (https=) |
| PL (1) | PL208927B1 (https=) |
| PT (2) | PT1401435E (https=) |
| WO (1) | WO2003000259A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10129715A1 (de) * | 2001-06-22 | 2003-01-02 | Bayer Ag | Thiazolylamide |
| DE102005014248A1 (de) * | 2005-03-30 | 2006-10-05 | Aicuris Gmbh & Co. Kg | Pharmazeutische Zubereitung von N-[5-(Aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamid |
| CN103269593A (zh) * | 2010-11-01 | 2013-08-28 | 罗马克实验室有限公司 | 烷基亚磺酰基取代的噻唑化物化合物 |
| EP2573086A1 (en) * | 2011-09-26 | 2013-03-27 | AiCuris GmbH & Co. KG | N-[5-(Aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide mesylate monohydrate |
| EP2573085A1 (en) | 2011-09-26 | 2013-03-27 | AiCuris GmbH & Co. KG | N-[5-(aminosulfonyl)-4methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl] acetamide mesylate monohydrate having a specific particle size distribution range and a specific surface area range |
| JP6918823B2 (ja) | 2016-04-06 | 2021-08-11 | イノベーティブ モレキュールズ ゲーエムベーハーＩｎｎｏｖａｔｉｖｅ Ｍｏｌｅｃｕｌｅｓ Ｇｍｂｈ | 抗ウイルス剤として有用なアミノチアゾール誘導体 |
| LT3544976T (lt) | 2016-11-28 | 2021-08-10 | Aicuris Gmbh & Co. Kg | N-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-n-metil-2-[4-(2-piridinil)-fenil]-acetamido laisvos bazės hemihidratas, jo gamybos būdai ir panaudojimai |
| AR110251A1 (es) | 2016-11-28 | 2019-03-13 | Aicuris Anti Infective Cures Gmbh | Una sal maleato de la base libre de n-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-n-metil-2-[4-(2-piridinil)-fenil]-acetamida, formulaciones farmacéuticas, métodos de fabricación y usos de la misma |
| AR110250A1 (es) * | 2016-11-28 | 2019-03-13 | Aicuris Anti Infective Cures Gmbh | Formulación tópica que comprende n-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-n-metil-2-[4-(2-piridinil)-fenil]-acetamida |
| WO2019068817A1 (en) | 2017-10-05 | 2019-04-11 | Innovative Molecules Gmbh | SUBSTITUTED THIAZOLEAN ENANTIOMERS AS ANTIVIRAL COMPOUNDS |
| EP3925595A1 (en) * | 2020-06-17 | 2021-12-22 | AiCuris GmbH & Co. KG | Ophthalmic formulation comprising n-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-n-methyl-2-[4-(2-pyridinyl)phenyl] acetamide hemihydrate |
| CA3168721A1 (en) * | 2020-03-26 | 2021-09-30 | Jessica Redmer | Ophthalmic formulation comprising n-[5-(aminosulfonyl)-4-methyl-1,3- thiazol-2-yl]-n-methyl-2-[4-(2-pyridinyl)phenyl]acetamide hemihydrate |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CA984848A (en) | 1970-01-16 | 1976-03-02 | Kurt H. Pilgram | Herbicides |
| US3658830A (en) * | 1970-01-16 | 1972-04-25 | Shell Oil Co | 5-(substituted mercapto sulfiny sulfonyl or sulfamoyl) |
| US3717651A (en) * | 1970-04-20 | 1973-02-20 | Shell Oil Co | Thiazoles |
| US3847588A (en) * | 1970-04-20 | 1974-11-12 | Shell Oil Co | Thiazoles herbicidal |
| GB2080682B (en) * | 1980-07-30 | 1984-03-28 | Ciba Geigy Ag | Antiherpetically active lipstick |
| US4556560A (en) * | 1983-01-24 | 1985-12-03 | The Procter & Gamble Company | Methods for the treatment and prophylaxis of diaper rash and diaper dermatitis |
| DE3319282A1 (de) * | 1983-05-27 | 1984-11-29 | Gödecke AG, 1000 Berlin | Verwendung von adenosin bei der behandlung von herpes |
| ES2186811T3 (es) | 1995-12-29 | 2003-05-16 | Boehringer Ingelheim Pharma | Derivados de feniltiazol con propiedades anti-virus herpes. |
| GB2311069A (en) | 1996-03-14 | 1997-09-17 | Merck & Co Inc | Primase isolated from human cytomegalovirus (HCMV) |
| US5705344A (en) | 1996-03-14 | 1998-01-06 | Tularik, Inc. | High-throughput screening assay for inhibitors of nucleic acid helicases |
| GB2311068A (en) | 1996-03-14 | 1997-09-17 | Merck & Co Inc | Helicase isolated from human cytomegalovirus (HCMV) |
| CA2223032A1 (en) | 1997-02-21 | 1998-08-21 | Smithkline Beecham Corporation | Use of hsv-1 ul-15 and vp5 in identifying anti-viral agents |
| DE19802437A1 (de) | 1998-01-23 | 1999-07-29 | Bayer Ag | Verwendung von substituierten Sulfonamiden als anitvirale Mittel und neue Stoffe |
| AU3289299A (en) | 1998-02-19 | 1999-09-06 | Tularik Inc. | Antiviral agents |
| NZ507032A (en) | 1998-03-19 | 2003-06-30 | Pharmacia & Upjohn | 1,3,4-thiadiazoles useful for the treatment of herpes and cytomegalovirus infections |
| WO2000053591A1 (de) * | 1999-03-08 | 2000-09-14 | Bayer Aktiengesellschaft | Thiazolylharnstoff-derivate und ihre verwendung als antivirale mittel |
| DOP2000000109A (es) * | 1999-12-23 | 2002-08-30 | Gerald Kleymann | Derivados de tiazolilamida |
| EP1319185A1 (en) * | 2000-06-15 | 2003-06-18 | Bayer Aktiengesellschaft | Method for identifying compounds with anti-herpes activity |
| DE10129716A1 (de) | 2001-06-22 | 2003-01-02 | Bayer Ag | Kombinationspräparate zur Herpes-Behandlung |
| DE10131128A1 (de) | 2001-06-28 | 2003-01-16 | Bayer Ag | Sekundäre Sulfonamide |
| WO2004078163A2 (en) | 2003-02-28 | 2004-09-16 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| DE102005014248A1 (de) * | 2005-03-30 | 2006-10-05 | Aicuris Gmbh & Co. Kg | Pharmazeutische Zubereitung von N-[5-(Aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamid |
-
2001
- 2001-06-22 DE DE10129714A patent/DE10129714A1/de not_active Withdrawn
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2002
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- 2002-06-10 US US10/481,680 patent/US7883713B2/en not_active Expired - Lifetime
- 2002-06-10 WO PCT/EP2002/006327 patent/WO2003000259A1/de not_active Ceased
- 2002-06-10 AU AU2002345023A patent/AU2002345023B2/en not_active Expired
- 2002-06-10 JP JP2003506904A patent/JP4342304B2/ja not_active Expired - Lifetime
- 2002-06-10 ES ES05024999T patent/ES2341778T3/es not_active Expired - Lifetime
- 2002-06-10 BR BRPI0210601A patent/BRPI0210601B8/pt not_active IP Right Cessation
- 2002-06-10 CN CN028125304A patent/CN1535149B/zh not_active Expired - Lifetime
- 2002-06-10 PL PL364378A patent/PL208927B1/pl unknown
- 2002-06-10 AT AT02743172T patent/ATE320253T1/de active
- 2002-06-10 PT PT02743172T patent/PT1401435E/pt unknown
- 2002-06-10 EP EP05024999A patent/EP1629842B1/de not_active Expired - Lifetime
- 2002-06-10 PT PT05024999T patent/PT1629842E/pt unknown
- 2002-06-10 ES ES02743172T patent/ES2260449T3/es not_active Expired - Lifetime
- 2002-06-10 DK DK05024999.4T patent/DK1629842T3/da active
- 2002-06-10 EP EP02743172A patent/EP1401435B1/de not_active Expired - Lifetime
- 2002-06-10 KR KR1020037016645A patent/KR100899491B1/ko not_active Expired - Fee Related
- 2002-06-10 DE DE50206084T patent/DE50206084D1/de not_active Expired - Lifetime
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