ZA200005153B - Novel crystalline forms of an antiviral benzimidazole compound. - Google Patents
Novel crystalline forms of an antiviral benzimidazole compound. Download PDFInfo
- Publication number
- ZA200005153B ZA200005153B ZA200005153A ZA200005153A ZA200005153B ZA 200005153 B ZA200005153 B ZA 200005153B ZA 200005153 A ZA200005153 A ZA 200005153A ZA 200005153 A ZA200005153 A ZA 200005153A ZA 200005153 B ZA200005153 B ZA 200005153B
- Authority
- ZA
- South Africa
- Prior art keywords
- benzimidazole
- isopropylamino
- dichloro
- ribofuranosyl
- ray powder
- Prior art date
Links
- 230000000840 anti-viral effect Effects 0.000 title claims description 5
- -1 benzimidazole compound Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 90
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 61
- 239000012453 solvate Substances 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 16
- 229910052802 copper Inorganic materials 0.000 claims description 16
- 239000010949 copper Substances 0.000 claims description 16
- 229910002804 graphite Inorganic materials 0.000 claims description 16
- 239000010439 graphite Substances 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 208000036142 Viral infection Diseases 0.000 claims description 5
- 230000009385 viral infection Effects 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 3
- 238000013160 medical therapy Methods 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 2
- 150000003839 salts Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 5
- 239000003937 drug carrier Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000003826 tablet Substances 0.000 description 26
- KJFBVJALEQWJBS-XUXIUFHCSA-N maribavir Chemical compound CC(C)NC1=NC2=CC(Cl)=C(Cl)C=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O KJFBVJALEQWJBS-XUXIUFHCSA-N 0.000 description 25
- 239000004615 ingredient Substances 0.000 description 24
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- 238000010438 heat treatment Methods 0.000 description 18
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 13
- 238000009472 formulation Methods 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 238000002441 X-ray diffraction Methods 0.000 description 10
- 239000008213 purified water Substances 0.000 description 10
- 239000002775 capsule Substances 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 235000019359 magnesium stearate Nutrition 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 238000011321 prophylaxis Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 6
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000012512 characterization method Methods 0.000 description 6
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- 239000008108 microcrystalline cellulose Substances 0.000 description 6
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- 239000000706 filtrate Substances 0.000 description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-DCSYEGIMSA-N Beta-Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-DCSYEGIMSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
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- 230000002265 prevention Effects 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000001509 sodium citrate Substances 0.000 description 3
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 230000003612 virological effect Effects 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 206010011831 Cytomegalovirus infection Diseases 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 241000711557 Hepacivirus Species 0.000 description 2
- 241000700721 Hepatitis B virus Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 208000002672 hepatitis B Diseases 0.000 description 2
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
- 229960002216 methylparaben Drugs 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229940100692 oral suspension Drugs 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229940068968 polysorbate 80 Drugs 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
- 239000004299 sodium benzoate Substances 0.000 description 2
- 235000010234 sodium benzoate Nutrition 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 230000004584 weight gain Effects 0.000 description 2
- 235000019786 weight gain Nutrition 0.000 description 2
- 238000005550 wet granulation Methods 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010019973 Herpes virus infection Diseases 0.000 description 1
- 208000029433 Herpesviridae infectious disease Diseases 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
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- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000007910 chewable tablet Substances 0.000 description 1
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- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
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- 238000007906 compression Methods 0.000 description 1
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- 238000007796 conventional method Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
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- 230000002939 deleterious effect Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000007919 dispersible tablet Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
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- 239000006186 oral dosage form Substances 0.000 description 1
- 229940100688 oral solution Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
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- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
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- 230000000699 topical effect Effects 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/052—Imidazole radicals
-
- 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
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- 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
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/7056—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing five-membered rings with nitrogen as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9807354.7A GB9807354D0 (en) | 1998-04-07 | 1998-04-07 | Antiviral compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200005153B true ZA200005153B (en) | 2001-09-26 |
Family
ID=10829932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200005153A ZA200005153B (en) | 1998-04-07 | 2000-09-26 | Novel crystalline forms of an antiviral benzimidazole compound. |
Country Status (28)
| Country | Link |
|---|---|
| US (9) | US6469160B1 (de) |
| EP (1) | EP1071693B1 (de) |
| JP (1) | JP2002510703A (de) |
| KR (1) | KR20010074472A (de) |
| CN (1) | CN1303390A (de) |
| AP (1) | AP2000001947A0 (de) |
| AT (1) | ATE261452T1 (de) |
| AU (1) | AU752877B2 (de) |
| BR (1) | BR9909474A (de) |
| CA (1) | CA2327494C (de) |
| DE (1) | DE69915461T2 (de) |
| EA (1) | EA002970B1 (de) |
| EE (1) | EE04120B1 (de) |
| ES (1) | ES2216503T3 (de) |
| GB (1) | GB9807354D0 (de) |
| HR (1) | HRP20000669A2 (de) |
| HU (1) | HUP0101669A3 (de) |
| ID (1) | ID27109A (de) |
| IL (1) | IL138697A0 (de) |
| IS (1) | IS5640A (de) |
| NO (1) | NO20005005L (de) |
| NZ (1) | NZ507173A (de) |
| PL (1) | PL343397A1 (de) |
| SK (1) | SK14832000A3 (de) |
| TR (1) | TR200002860T2 (de) |
| WO (1) | WO1999051618A1 (de) |
| YU (1) | YU60900A (de) |
| ZA (1) | ZA200005153B (de) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9807354D0 (en) * | 1998-04-07 | 1998-06-03 | Glaxo Group Ltd | Antiviral compound |
| GB9807355D0 (en) | 1998-04-07 | 1998-06-03 | Glaxo Group Ltd | Antiviral compound |
| GB0008939D0 (en) * | 2000-04-11 | 2000-05-31 | Glaxo Group Ltd | Process for preparing substituted benzimidazole compounds |
| EA007120B8 (ru) | 2002-05-16 | 2012-03-30 | Тиботек Фармасьютикалз Лтд. | Псевдополиморфные формы ингибитора вич-протеазы |
| ES2370829T3 (es) * | 2004-06-02 | 2011-12-23 | Sandoz Ag | Producto intermedio de meropenem en forma cristalina. |
| EP1910393A2 (de) * | 2005-07-05 | 2008-04-16 | Hetero Drugs Limited | Neues verfahren zur herstellung von didanosin unter verwendung neuer zwischenprodukte |
| US9198862B2 (en) * | 2005-07-22 | 2015-12-01 | Rubicon Research Private Limited | Dispersible tablet composition |
| CN101287706A (zh) * | 2005-09-21 | 2008-10-15 | 尼科梅德有限责任公司 | 作为组蛋白脱乙酰基酶抑制剂的磺酰基吡咯盐酸盐 |
| NZ567357A (en) * | 2005-10-31 | 2011-05-27 | Janssen Pharmaceutica Nv | Novel processes for the preparation of piperazinyl and diazapanyl benzamide derivatives |
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| GB9807355D0 (en) | 1998-04-07 | 1998-06-03 | Glaxo Group Ltd | Antiviral compound |
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1998
- 1998-04-07 GB GBGB9807354.7A patent/GB9807354D0/en not_active Ceased
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1999
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- 1999-04-01 KR KR1020007011089A patent/KR20010074472A/ko not_active Application Discontinuation
- 1999-04-01 CA CA2327494A patent/CA2327494C/en not_active Expired - Lifetime
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- 1999-04-01 CN CN99806894A patent/CN1303390A/zh active Pending
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- 1999-04-01 HU HU0101669A patent/HUP0101669A3/hu unknown
- 1999-04-01 JP JP2000542339A patent/JP2002510703A/ja active Pending
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- 1999-04-01 PL PL99343397A patent/PL343397A1/xx unknown
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- 2000-09-26 ZA ZA200005153A patent/ZA200005153B/en unknown
- 2000-10-04 NO NO20005005A patent/NO20005005L/no not_active Application Discontinuation
- 2000-10-09 HR HR20000669A patent/HRP20000669A2/hr not_active Application Discontinuation
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- 2001-10-29 US US10/007,272 patent/US7297683B2/en not_active Expired - Fee Related
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- 2007-10-25 US US11/924,204 patent/US7714123B2/en not_active Expired - Fee Related
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