OA10707A - Terapeutic compounds. - Google Patents

Terapeutic compounds. Download PDF

Info

Publication number: OA10707A
Authority: OA; OAPI
Prior art keywords: alkyl; mmol; benzimidazole; beta; formula
Prior art date: 1996-01-05

Application number

OA9800098A

Other languages

English (en)

Inventor

Stanley Chamberlain

George Walter Koszalka

Jeffrey H Tidwell

Nanine Van Draanen

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.)

1996-01-05

Filing date

1998-06-30

Publication date

2001-05-09

1998-06-30 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2001-05-09 Publication of OA10707A publication Critical patent/OA10707A/en

Links

150000001875 compounds Chemical class 0.000 title claims description 96
238000011282 treatment Methods 0.000 claims abstract description 19
230000009385 viral infection Effects 0.000 claims abstract description 8
238000011321 prophylaxis Methods 0.000 claims abstract description 7
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims description 53
229910052739 hydrogen Inorganic materials 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 31
125000005843 halogen group Chemical group 0.000 claims description 26
-1 azido, hydroxy Chemical group 0.000 claims description 24
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
150000002431 hydrogen Chemical group 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 7
125000001072 heteroaryl group Chemical group 0.000 claims description 7
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 6
208000036142 Viral infection Diseases 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
101100240523 Caenorhabditis elegans nhr-19 gene Proteins 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000001627 3 membered heterocyclic group Chemical group 0.000 claims description 2
125000001963 4 membered heterocyclic group Chemical group 0.000 claims description 2
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
238000002560 therapeutic procedure Methods 0.000 claims description 2
125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
125000000392 cycloalkenyl group Chemical group 0.000 claims 1
125000000548 ribosyl group Chemical group C1([C@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 1
241001529453 unidentified herpesvirus Species 0.000 abstract description 4
238000013160 medical therapy Methods 0.000 abstract description 3
229940058303 antinematodal benzimidazole derivative Drugs 0.000 abstract 2
125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 abstract 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 143
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
239000000203 mixture Substances 0.000 description 65
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 59
239000000243 solution Substances 0.000 description 56
238000000034 method Methods 0.000 description 54
239000007787 solid Substances 0.000 description 52
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 49
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
239000000047 product Substances 0.000 description 39
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
238000009472 formulation Methods 0.000 description 38
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 35
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 22
239000003795 chemical substances by application Substances 0.000 description 22
235000019439 ethyl acetate Nutrition 0.000 description 22
239000002904 solvent Substances 0.000 description 20
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208000015181 infectious disease Diseases 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
235000017550 sodium carbonate Nutrition 0.000 description 17
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UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 13
150000002148 esters Chemical class 0.000 description 13
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 12
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 11
150000001718 carbodiimides Chemical class 0.000 description 11
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 10
201000010099 disease Diseases 0.000 description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
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VHBFEIBMZHEWSX-UHFFFAOYSA-N 2-isothiocyanatopropane Chemical compound CC(C)N=C=S VHBFEIBMZHEWSX-UHFFFAOYSA-N 0.000 description 9
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
150000003839 salts Chemical class 0.000 description 9
FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 9
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 8
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 8
229920000036 polyvinylpyrrolidone Polymers 0.000 description 8
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239000000725 suspension Substances 0.000 description 8
241000701044 Human gammaherpesvirus 4 Species 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 7
239000000499 gel Substances 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
239000000843 powder Substances 0.000 description 7
238000000746 purification Methods 0.000 description 7
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
241000282414 Homo sapiens Species 0.000 description 6
241000701085 Human alphaherpesvirus 3 Species 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000008186 active pharmaceutical agent Substances 0.000 description 6
239000002775 capsule Substances 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
125000001309 chloro group Chemical group Cl* 0.000 description 6
239000003814 drug Substances 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
239000000463 material Substances 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 5
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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 5
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
125000001246 bromo group Chemical group Br* 0.000 description 5
239000008101 lactose Substances 0.000 description 5
239000010410 layer Substances 0.000 description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
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239000011734 sodium Substances 0.000 description 5
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ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 5
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PYMYPHUHKUWMLA-LMVFSUKVSA-N aldehydo-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 4
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229960001179 penciclovir Drugs 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
RESQXSFWYYDQBW-UHFFFAOYSA-N phenoxycarbothioyl hypochlorite Chemical compound ClOC(=S)OC1=CC=CC=C1 RESQXSFWYYDQBW-UHFFFAOYSA-N 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
230000036470 plasma concentration Effects 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
230000035935 pregnancy Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
239000008213 purified water Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
206010037844 rash Diseases 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
230000007017 scission Effects 0.000 description 1
231100000046 skin rash Toxicity 0.000 description 1
239000002002 slurry Substances 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
229940032147 starch Drugs 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid group Chemical group C(CCC(=O)O)(=O)O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
150000003444 succinic acids Chemical class 0.000 description 1
125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 1
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
GMRIOAVKKGNMMV-UHFFFAOYSA-N tetrabutylazanium;azide Chemical compound [N-]=[N+]=[N-].CCCC[N+](CCCC)(CCCC)CCCC GMRIOAVKKGNMMV-UHFFFAOYSA-N 0.000 description 1
QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229940093257 valacyclovir Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical class CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
244000052613 viral pathogen Species 0.000 description 1
230000008673 vomiting Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008215 water for injection Substances 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
- 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

Landscapes

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

OA9800098A 1996-01-05 1998-06-30 Terapeutic compounds. OA10707A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB9600143.3A GB9600143D0 (en)	1996-01-05	1996-01-05	Therapeutic compounds

Publications (1)

Publication Number	Publication Date
OA10707A true OA10707A (en)	2001-05-09

Family

ID=10786611

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9800098A OA10707A (en)	1996-01-05	1998-06-30	Terapeutic compounds.

Country Status (21)

Country	Link
US (2)	US6204249B1 (is)
EP (1)	EP0876389A1 (is)
JP (1)	JP2000515119A (is)
KR (1)	KR19990077041A (is)
CN (1)	CN1214049A (is)
AP (1)	AP9801286A0 (is)
AU (1)	AU729541B2 (is)
BR (1)	BR9612413A (is)
CA (1)	CA2241993A1 (is)
CZ (1)	CZ212698A3 (is)
EA (1)	EA001770B1 (is)
GB (1)	GB9600143D0 (is)
HU (1)	HUP9904301A3 (is)
IS (1)	IS4789A (is)
MX (1)	MX9805441A (is)
NO (1)	NO983090L (is)
NZ (1)	NZ324380A (is)
OA (1)	OA10707A (is)
PL (1)	PL327732A1 (is)
TR (1)	TR199801289T2 (is)
WO (1)	WO1997025337A1 (is)

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* Cited by examiner, † Cited by third party
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DE69624827T2 (de) *	1995-08-18	2003-09-04	The Regents Of The University Of Michigan, Ann Arbor	5'-substitutierte-ribofuranosyl benzimidazolen als antivirale.
GB9600143D0 (en) *	1996-01-05	1996-03-06	Wellcome Found	Therapeutic compounds
CA2280761A1 (en) *	1997-02-13	1998-08-20	Stanley Dawes Chamberlain	Benzimidazole derivatives
EP0963371B1 (en)	1997-02-25	2003-05-02	THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES	Substituted benzimidazoles as non-nucleoside inhibitors of reverse transcriptase
NZ502882A (en)	1997-07-30	2002-02-01	Glaxo Group Ltd	Lyxofuranosyl benzimidazoles as antiviral agents
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
WO2005063788A1 (ja) *	2003-12-26	2005-07-14	Kissei Pharmaceutical Co., Ltd.	ベンズイミダゾール誘導体及びその医薬用途
CA2707641A1 (en) *	2007-10-05	2009-04-09	Api Corporation	Process for producing ribofuranose derivatives
US12043644B2 (en) *	2020-06-23	2024-07-23	Biometrix Technology Inc	Benzimidazole derivatives, preparation method thereof and use thereof as anti-cancer agent or anti-virus agent comprising the same
PL4475844T3 (pl) *	2022-10-12	2025-11-12	Takeda Pharmaceutical Company Limited	Sposób otrzymywania maribawiru
WO2024103979A1 (zh) *	2022-11-17	2024-05-23	北京凯因科技股份有限公司	一种抑制疱疹病毒的化合物
CN119119151A (zh) *	2024-09-04	2024-12-13	斯坦德药典标准物质研发(湖北)有限公司	一种马立巴韦的制备方法

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DE130030C (is)
US3399987A (en)	1965-08-02	1968-09-03	United States Borax Chem	2-alkylaminobenzimidazoles as herbicides
CH443777A (de)	1965-08-06	1968-02-15	Agripat Sa	Verfahren zum Schützen textiler Keratinfasern vor Insektenfrass und Mittel zur Durchführung dieses Verfahrens
US3655901A (en)	1970-07-30	1972-04-11	Merck & Co Inc	Method of inhibiting the formation of phenylethanalamine-n-methyl transferase with 2-aminobenzimidazoles
US4002623A (en)	1974-08-07	1977-01-11	Pfizer Inc.	Anti-inflammatory 1-[3-(dialkylamino)propyl]-2-acylaminobenzimidazoles and 2-acylamino-3-[3-(dialkylamino)-propyl]imidazo[4,5-b]pyridines
FR2551442B1 (fr)	1983-09-05	1987-04-30	Centre Nat Rech Scient	Nouveaux derives furaniques, leur preparation et leur application
EP0304624A3 (de)	1987-07-29	1989-03-22	F. Hoffmann-La Roche Ag	Benzimidazol-2-yl-pyridiniumverbindungen
IT1226100B (it)	1988-07-07	1990-12-10	Dompe Farmaceutici Spa	Derivati benzimidazolici farmacologicamente attivi.
SE9003151D0 (sv)	1990-10-02	1990-10-02	Medivir Ab	Nucleoside derivatives
US5248672A (en)	1990-11-01	1993-09-28	The Regents Of The University Of Michigan	Polysubstituted benzimidazole nucleosides as antiviral agents
WO1992018517A1 (en)	1991-04-17	1992-10-29	Yale University	Method of treating or preventing hepatitis b virus
ZA923640B (en)	1991-05-21	1993-02-24	Iaf Biochem Int	Processes for the diastereoselective synthesis of nucleosides
GB9205071D0 (en)	1992-03-09	1992-04-22	Wellcome Found	Therapeutic nucleosides
WO1994008456A1 (en) *	1992-10-21	1994-04-28	The Regents Of The University Of Michigan	Polysubstituted benzimidazoles as antiviral agents
GB9226879D0 (en)	1992-12-23	1993-02-17	Iaf Biochem Int	Anti-viral compounds
US5399580A (en)	1993-03-08	1995-03-21	Burroughs Wellcome Co.	Therapeutic nucleosides-uses
GB9413724D0 (en)	1994-07-07	1994-08-24	Wellcome Found	Therapeutic nucleosides
DE69624827T2 (de)	1995-08-18	2003-09-04	The Regents Of The University Of Michigan, Ann Arbor	5'-substitutierte-ribofuranosyl benzimidazolen als antivirale.
GB9600143D0 (en) *	1996-01-05	1996-03-06	Wellcome Found	Therapeutic compounds
US5995610A (en) *	1997-05-06	1999-11-30	Telefonaktiebolaget Lm Ericsson	Cooperative call processing across public and private intelligent networks

1996
- 1996-01-05 GB GBGB9600143.3A patent/GB9600143D0/en active Pending
- 1996-12-19 BR BR9612413A patent/BR9612413A/pt not_active Application Discontinuation
- 1996-12-19 PL PL96327732A patent/PL327732A1/xx unknown
- 1996-12-19 KR KR1019980705174A patent/KR19990077041A/ko not_active Withdrawn
- 1996-12-19 AP APAP/P/1998/001286A patent/AP9801286A0/en unknown
- 1996-12-19 JP JP09524940A patent/JP2000515119A/ja not_active Abandoned
- 1996-12-19 TR TR1998/01289T patent/TR199801289T2/xx unknown
- 1996-12-19 EA EA199800526A patent/EA001770B1/ru not_active IP Right Cessation
- 1996-12-19 CZ CZ982126A patent/CZ212698A3/cs unknown
- 1996-12-19 WO PCT/GB1996/003151 patent/WO1997025337A1/en not_active Ceased
- 1996-12-19 HU HU9904301A patent/HUP9904301A3/hu unknown
- 1996-12-19 CN CN96180163A patent/CN1214049A/zh active Pending
- 1996-12-19 US US09/101,103 patent/US6204249B1/en not_active Expired - Lifetime
- 1996-12-19 CA CA002241993A patent/CA2241993A1/en not_active Abandoned
- 1996-12-19 EP EP96942504A patent/EP0876389A1/en not_active Withdrawn
- 1996-12-19 NZ NZ324380A patent/NZ324380A/xx unknown
- 1996-12-19 AU AU11640/97A patent/AU729541B2/en not_active Ceased
1998
- 1998-06-30 OA OA9800098A patent/OA10707A/en unknown
- 1998-06-30 IS IS4789A patent/IS4789A/is unknown
- 1998-07-03 NO NO983090A patent/NO983090L/no not_active Application Discontinuation
- 1998-07-03 MX MX9805441A patent/MX9805441A/es not_active IP Right Cessation
2000
- 2000-11-14 US US09/712,739 patent/US6617315B1/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
PL327732A1 (en)	1998-12-21
WO1997025337A1 (en)	1997-07-17
AU1164097A (en)	1997-08-01
EA199800526A1 (ru)	1999-04-29
KR19990077041A (ko)	1999-10-25
NO983090L (no)	1998-09-01
CA2241993A1 (en)	1997-07-17
AU729541B2 (en)	2001-02-01
JP2000515119A (ja)	2000-11-14
HUP9904301A2 (hu)	2000-05-28
EA001770B1 (ru)	2001-08-27
CN1214049A (zh)	1999-04-14
BR9612413A (pt)	1999-07-13
EP0876389A1 (en)	1998-11-11
MX9805441A (es)	1998-11-30
CZ212698A3 (cs)	1998-12-16
AP9801286A0 (en)	1998-09-30
HUP9904301A3 (en)	2001-07-30
NO983090D0 (no)	1998-07-03
IS4789A (is)	1998-06-30
US6617315B1 (en)	2003-09-09
TR199801289T2 (en)	1998-10-21
US6204249B1 (en)	2001-03-20
GB9600143D0 (en)	1996-03-06
NZ324380A (en)	2000-01-28

Publication	Publication Date	Title
AP736A (en)	1999-03-09	Benzimidazole derivatives and their use in medical therapy particularly for the treatment of virus infections.
AP1262A (en)	2004-03-16	Benzimidazole derivatives.
OA10707A (en)	2001-05-09	Terapeutic compounds.
EP0970100B1 (en)	2003-11-12	Benzimidazole derivatives
CA2193665C (en)	2005-11-01	Benzimidazole derivatives for the treatment and prophylaxis of virus infections
ITOH et al.	1983	Studies on the Chemical Synthesis of Potential Antimetabolites. XXXIV. Apparent Discrepancy among Reported Proton Nuclear Magnetic Resonance Spectra of 3-Deazaadenosine Is Actually a Reflection of a Difference in Molecular Species
HK1003711B (en)	2000-11-24	Therapeutic compounds
CZ448299A3 (cs)	2000-07-12	Benzimidazolové deriváty, způsob jejich výroby, farmaceutický prostředek obsahující tyto deriváty a použití těchto derivátů