ZA200005153B - Novel crystalline forms of an antiviral benzimidazole compound. - Google Patents

Novel crystalline forms of an antiviral benzimidazole compound. Download PDF

Info

Publication number: ZA200005153B
Authority: ZA; South Africa
Prior art keywords: benzimidazole; isopropylamino; dichloro; ribofuranosyl; ray powder
Prior art date: 1998-04-07

Application number

ZA200005153A

Other languages

English (en)

Inventor

Barry Howard Carter

Lian-Feng Huang

Stacey Todd Long

Eric Allen Schmitt

Bobby Neal Glover

Robert William Lancaster

Michele Catherine Rizzolio

Barry Riddle Sickles

Original Assignee

Glaxo Group Ltd

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.)

1998-04-07

Filing date

2000-09-26

Publication date

2001-09-26

2000-09-26 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2001-09-26 Publication of ZA200005153B publication Critical patent/ZA200005153B/en

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
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238000012512 characterization method Methods 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
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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
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230000003612 virological effect Effects 0.000 description 3
238000005406 washing Methods 0.000 description 3
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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
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000007910 chewable tablet Substances 0.000 description 1
229940068682 chewable tablet Drugs 0.000 description 1
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
239000007891 compressed tablet Substances 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
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
238000002474 experimental method Methods 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
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235000019322 gelatine Nutrition 0.000 description 1
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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
239000011541 reaction mixture Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
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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239000006068 taste-masking agent Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Molecular Biology (AREA)
Epidemiology (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
Virology (AREA)
Biochemistry (AREA)
Genetics & Genomics (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

ZA200005153A 1998-04-07 2000-09-26 Novel crystalline forms of an antiviral benzimidazole compound. ZA200005153B (en)

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 (id)
EP (1)	EP1071693B1 (id)
JP (1)	JP2002510703A (id)
KR (1)	KR20010074472A (id)
CN (1)	CN1303390A (id)
AP (1)	AP2000001947A0 (id)
AT (1)	ATE261452T1 (id)
AU (1)	AU752877B2 (id)
BR (1)	BR9909474A (id)
CA (1)	CA2327494C (id)
DE (1)	DE69915461T2 (id)
EA (1)	EA002970B1 (id)
EE (1)	EE04120B1 (id)
ES (1)	ES2216503T3 (id)
GB (1)	GB9807354D0 (id)
HR (1)	HRP20000669A2 (id)
HU (1)	HUP0101669A3 (id)
ID (1)	ID27109A (id)
IL (1)	IL138697A0 (id)
IS (1)	IS5640A (id)
NO (1)	NO20005005L (id)
NZ (1)	NZ507173A (id)
PL (1)	PL343397A1 (id)
SK (1)	SK14832000A3 (id)
TR (1)	TR200002860T2 (id)
WO (1)	WO1999051618A1 (id)
YU (1)	YU60900A (id)
ZA (1)	ZA200005153B (id)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
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
BRPI0311176B8 (pt)	2002-05-16	2021-05-25	Janssen Sciences Ireland Uc	pseudopolimorfo na forma de etanolato, seu uso, processo de preparação do mesmo e composição farmacêutica
WO2005118586A1 (en) *	2004-06-02	2005-12-15	Sandoz Ag	Meropenem intermediate in crystalline form
WO2007004230A2 (en) *	2005-07-05	2007-01-11	Hetero Drugs Limited	A novel process for the preparation of didanosine using novel intermediates
US9198862B2 (en) *	2005-07-22	2015-12-01	Rubicon Research Private Limited	Dispersible tablet composition
BRPI0616040A2 (pt) *	2005-09-21	2011-06-07	Nycomed Gmbh	cloridrato de sulfonilpirról como inibidor de histona desacetilases
EP2404911A1 (en) *	2005-10-31	2012-01-11	Janssen Pharmaceutica NV	Novel processes for the preparation of piperazinyl and diazapanyl benzamide derivatives
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1998
- 1998-04-07 GB GBGB9807354.7A patent/GB9807354D0/en not_active Ceased
1999
- 1999-04-01 NZ NZ507173A patent/NZ507173A/en unknown
- 1999-04-01 EP EP99917935A patent/EP1071693B1/en not_active Expired - Lifetime
- 1999-04-01 ES ES99917935T patent/ES2216503T3/es not_active Expired - Lifetime
- 1999-04-01 HR HR20000669A patent/HRP20000669A2/hr not_active Application Discontinuation
- 1999-04-01 SK SK1483-2000A patent/SK14832000A3/sk unknown
- 1999-04-01 YU YU60900A patent/YU60900A/sh unknown
- 1999-04-01 IL IL13869799A patent/IL138697A0/xx unknown
- 1999-04-01 EE EEP200000584A patent/EE04120B1/xx not_active IP Right Cessation
- 1999-04-01 WO PCT/EP1999/002214 patent/WO1999051618A1/en not_active Ceased
- 1999-04-01 KR KR1020007011089A patent/KR20010074472A/ko not_active Withdrawn
- 1999-04-01 EA EA200000911A patent/EA002970B1/ru not_active IP Right Cessation
- 1999-04-01 AU AU36034/99A patent/AU752877B2/en not_active Ceased
- 1999-04-01 PL PL99343397A patent/PL343397A1/xx unknown
- 1999-04-01 CA CA2327494A patent/CA2327494C/en not_active Expired - Lifetime
- 1999-04-01 DE DE69915461T patent/DE69915461T2/de not_active Expired - Lifetime
- 1999-04-01 TR TR2000/02860T patent/TR200002860T2/xx unknown
- 1999-04-01 CN CN99806894A patent/CN1303390A/zh active Pending
- 1999-04-01 JP JP2000542339A patent/JP2002510703A/ja active Pending
- 1999-04-01 US US09/647,962 patent/US6469160B1/en not_active Expired - Lifetime
- 1999-04-01 ID IDW20002036A patent/ID27109A/id unknown
- 1999-04-01 BR BR9909474-6A patent/BR9909474A/pt not_active IP Right Cessation
- 1999-04-01 AP APAP/P/2000/001947A patent/AP2000001947A0/en unknown
- 1999-04-01 AT AT99917935T patent/ATE261452T1/de not_active IP Right Cessation
- 1999-04-01 HU HU0101669A patent/HUP0101669A3/hu unknown
2000
- 2000-09-26 IS IS5640A patent/IS5640A/is unknown
- 2000-09-26 ZA ZA200005153A patent/ZA200005153B/en unknown
- 2000-10-04 NO NO20005005A patent/NO20005005L/no not_active Application Discontinuation
2001
- 2001-10-29 US US10/007,272 patent/US7297683B2/en not_active Expired - Fee Related
2007
- 2007-10-25 US US11/924,204 patent/US7714123B2/en not_active Expired - Fee Related
2010
- 2010-03-26 US US12/732,302 patent/US20100179101A1/en not_active Abandoned
2011
- 2011-01-25 US US13/012,924 patent/US9163052B2/en not_active Expired - Fee Related
2013
- 2013-02-01 US US13/756,612 patent/US20130261294A1/en not_active Abandoned
2015
- 2015-10-12 US US14/880,600 patent/US20160030460A1/en not_active Abandoned
2016
- 2016-09-19 US US15/268,949 patent/US20170002035A1/en not_active Abandoned
2017
- 2017-10-05 US US15/725,785 patent/US20180044366A1/en not_active Abandoned

Also Published As

Publication number	Publication date
SK14832000A3 (sk)	2001-07-10
ATE261452T1 (de)	2004-03-15
EP1071693B1 (en)	2004-03-10
GB9807354D0 (en)	1998-06-03
US20020177703A1 (en)	2002-11-28
US9163052B2 (en)	2015-10-20
NO20005005L (no)	2000-12-06
EA002970B1 (ru)	2002-12-26
IS5640A (is)	2000-09-26
ES2216503T3 (es)	2004-10-16
US7297683B2 (en)	2007-11-20
US6469160B1 (en)	2002-10-22
ID27109A (id)	2001-03-01
US20130261294A1 (en)	2013-10-03
CN1303390A (zh)	2001-07-11
TR200002860T2 (tr)	2000-12-21
EE04120B1 (et)	2003-08-15
EE200000584A (et)	2002-04-15
US20080103186A1 (en)	2008-05-01
EA200000911A1 (ru)	2001-04-23
HUP0101669A2 (hu)	2001-10-28
US20100179101A1 (en)	2010-07-15
NZ507173A (en)	2003-07-25
US20180044366A1 (en)	2018-02-15
NO20005005D0 (no)	2000-10-04
DE69915461T2 (de)	2005-03-03
US7714123B2 (en)	2010-05-11
CA2327494A1 (en)	1999-10-14
DE69915461D1 (de)	2004-04-15
HRP20000669A2 (en)	2001-08-31
KR20010074472A (ko)	2001-08-04
PL343397A1 (en)	2001-08-13
US20170002035A1 (en)	2017-01-05
EP1071693A1 (en)	2001-01-31
HUP0101669A3 (en)	2003-07-28
US20160030460A1 (en)	2016-02-04
IL138697A0 (en)	2001-10-31
JP2002510703A (ja)	2002-04-09
AU3603499A (en)	1999-10-25
WO1999051618A1 (en)	1999-10-14
AU752877B2 (en)	2002-10-03
AP2000001947A0 (en)	2000-12-31
YU60900A (sh)	2003-07-07
CA2327494C (en)	2010-10-26
BR9909474A (pt)	2000-12-19
US20110118203A1 (en)	2011-05-19

Publication	Publication Date	Title
US7714123B2 (en)	2010-05-11	Crystalline forms of an antiviral benzimidazole compound
RS60900B1 (sr)	2020-11-30	Jedinjenja 6-heterociklil-4-morfolin-4-ilpiridin-2-ona korisna za lečenje kancera i dijabetesa
AU753527B2 (en)	2002-10-17	Form VI 5,6-dichloro-2-(isopropylamino)-1-(beta-L- ribofuranosyl)-1H-benzimidazole
MXPA00009734A (en)	2001-09-07	Novel crystalline forms of an antiviral benzimidazole compound
HK1032060B (en)	2003-07-18	Form vi 5,6-dichloro-2-(isopropylamino)-1-beta-l-ribofuranosyl)-1h-benzimidazole
MXPA00009703A (en)	2001-09-07	Form vi 5,6-dichloro-2-(isopropylamino)- 1-(&bgr;-l-ribofuranosyl)-1h-benzimidazole
CZ20003709A3 (cs)	2001-05-16	Nové krystalické formy protivirivé benzimidazolové sloučeniny
CZ20003716A3 (cs)	2001-04-11	Forma VI 5,6-dichlor-2-(isopropylamino)-l-betaL-ribofuranosyl-lH-benzimidazolu