UA75866C2 - Respiratory syncytial virus replication inhibitors - Google Patents

Respiratory syncytial virus replication inhibitors Download PDF

Info

Publication number: UA75866C2
Authority: UA; Ukraine
Prior art keywords: formula; hydrogen; piperidinyl; сно; intermediate compound
Prior art date: 1999-06-28

Application number

UA2002010361A

Other languages

English (en)

Ukrainian (uk)

Inventor

Jean Fernand Arman Lacrampe

Jerome Emil Georges Guillemont

Koenraad Jozef Ludovik Andries

Original Assignee

Janssen Pharmaceutica Nv

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-06-28

Filing date

2000-06-20

Publication date

2006-06-15

2000-06-20 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2006-06-15 Publication of UA75866C2 publication Critical patent/UA75866C2/uk

Links

241000725643 Respiratory syncytial virus Species 0.000 title abstract description 6
239000003112 inhibitor Substances 0.000 title 1
230000029812 viral genome replication Effects 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 398
239000000203 mixture Substances 0.000 claims abstract description 145
-1 C(=O) Chemical group 0.000 claims abstract description 119
239000001257 hydrogen Substances 0.000 claims abstract description 68
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 68
125000001424 substituent group Chemical group 0.000 claims abstract description 43
150000003839 salts Chemical class 0.000 claims abstract description 30
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
239000003814 drug Substances 0.000 claims abstract description 19
125000003118 aryl group Chemical group 0.000 claims abstract description 18
125000002618 bicyclic heterocycle group Chemical group 0.000 claims abstract description 18
150000001412 amines Chemical class 0.000 claims abstract description 17
239000002184 metal Chemical class 0.000 claims abstract description 13
229910052751 metal Inorganic materials 0.000 claims abstract description 13
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
229940002612 prodrug Drugs 0.000 claims abstract description 12
239000000651 prodrug Substances 0.000 claims abstract description 12
125000004076 pyridyl group Chemical group 0.000 claims abstract description 11
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 10
125000003386 piperidinyl group Chemical group 0.000 claims abstract description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 4
125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 3
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 2
239000002904 solvent Substances 0.000 claims description 130
238000006243 chemical reaction Methods 0.000 claims description 78
125000000217 alkyl group Chemical group 0.000 claims description 52
150000002431 hydrogen Chemical class 0.000 claims description 44
239000012442 inert solvent Substances 0.000 claims description 42
239000002253 acid Substances 0.000 claims description 34
239000002585 base Substances 0.000 claims description 32
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 30
238000000034 method Methods 0.000 claims description 26
238000010511 deprotection reaction Methods 0.000 claims description 24
229910052799 carbon Inorganic materials 0.000 claims description 21
239000003638 chemical reducing agent Substances 0.000 claims description 21
125000006239 protecting group Chemical group 0.000 claims description 17
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
230000000840 anti-viral effect Effects 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 14
229940079593 drug Drugs 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
CVQPQLRQAKXFFF-UHFFFAOYSA-N trihydrate;trihydrochloride Chemical compound O.O.O.Cl.Cl.Cl CVQPQLRQAKXFFF-UHFFFAOYSA-N 0.000 claims description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
239000003937 drug carrier Substances 0.000 claims description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
229910021529 ammonia Inorganic materials 0.000 claims description 7
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
208000036142 Viral infection Diseases 0.000 claims description 6
IZCQDRVQVRENLX-UHFFFAOYSA-N dihydrate;trihydrochloride Chemical compound O.O.Cl.Cl.Cl IZCQDRVQVRENLX-UHFFFAOYSA-N 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
230000009385 viral infection Effects 0.000 claims description 6
230000002378 acidificating effect Effects 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 5
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
231100000252 nontoxic Toxicity 0.000 claims description 5
230000003000 nontoxic effect Effects 0.000 claims description 5
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 4
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
235000019253 formic acid Nutrition 0.000 claims description 4
UUBJKHVFGWGJKX-UHFFFAOYSA-N hydrate tetrahydrochloride Chemical compound O.Cl.Cl.Cl.Cl UUBJKHVFGWGJKX-UHFFFAOYSA-N 0.000 claims description 4
230000002265 prevention Effects 0.000 claims description 4
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 3
125000004104 aryloxy group Chemical group 0.000 claims description 3
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
JKXCZYCVHPKTPK-UHFFFAOYSA-N hydrate;trihydrochloride Chemical compound O.Cl.Cl.Cl JKXCZYCVHPKTPK-UHFFFAOYSA-N 0.000 claims description 3
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
125000004590 pyridopyridyl group Chemical group N1=C(C=CC2=C1C=CC=N2)* 0.000 claims description 3
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
XMJIFRFCKXEIRF-UHFFFAOYSA-N O.O.O.O.Cl.Cl.Cl Chemical compound O.O.O.O.Cl.Cl.Cl XMJIFRFCKXEIRF-UHFFFAOYSA-N 0.000 claims description 2
125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000003373 pyrazinyl group Chemical group 0.000 claims description 2
VGKODZCNDHJSOX-UHFFFAOYSA-N trihydrate;tetrahydrochloride Chemical compound O.O.O.Cl.Cl.Cl.Cl VGKODZCNDHJSOX-UHFFFAOYSA-N 0.000 claims description 2
238000005576 amination reaction Methods 0.000 claims 10
125000001475 halogen functional group Chemical group 0.000 claims 4
238000011084 recovery Methods 0.000 claims 3
101100123850 Caenorhabditis elegans her-1 gene Proteins 0.000 claims 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 claims 1
241001206439 Motya Species 0.000 claims 1
206010061603 Respiratory syncytial virus infection Diseases 0.000 claims 1
238000010306 acid treatment Methods 0.000 claims 1
150000008043 acidic salts Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
150000004682 monohydrates Chemical class 0.000 claims 1
208000030925 respiratory syncytial virus infectious disease Diseases 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
238000011426 transformation method Methods 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 18
229910052717 sulfur Inorganic materials 0.000 abstract description 7
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 2
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
150000001204 N-oxides Chemical class 0.000 abstract 1
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 abstract 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
239000000543 intermediate Substances 0.000 description 292
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 102
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 76
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 75
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
239000012044 organic layer Substances 0.000 description 46
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 45
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
239000000243 solution Substances 0.000 description 40
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
239000003480 eluent Substances 0.000 description 33
239000000741 silica gel Substances 0.000 description 32
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238000004440 column chromatography Methods 0.000 description 31
239000003054 catalyst Substances 0.000 description 29
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150000003254 radicals Chemical class 0.000 description 25
239000002244 precipitate Substances 0.000 description 24
125000005843 halogen group Chemical group 0.000 description 21
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
239000000706 filtrate Substances 0.000 description 14
208000015181 infectious disease Diseases 0.000 description 14
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000006722 reduction reaction Methods 0.000 description 12
239000012312 sodium hydride Substances 0.000 description 12
229910000104 sodium hydride Inorganic materials 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
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241000700605 Viruses Species 0.000 description 9
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ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
229910052763 palladium Inorganic materials 0.000 description 6
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235000011181 potassium carbonates Nutrition 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000012279 sodium borohydride Substances 0.000 description 6
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
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239000007868 Raney catalyst Substances 0.000 description 4
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229910000564 Raney nickel Inorganic materials 0.000 description 4
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229910052794 bromium Inorganic materials 0.000 description 4
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IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
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238000006268 reductive amination reaction Methods 0.000 description 3
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150000002576 ketones Chemical class 0.000 description 1
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OSDUDPQWLGJWGL-UHFFFAOYSA-N tert-butyl 4-(1h-benzimidazol-2-ylamino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=NC2=CC=CC=C2N1 OSDUDPQWLGJWGL-UHFFFAOYSA-N 0.000 description 1
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KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
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GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- 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
- 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
- A61P31/14—Antivirals for RNA viruses
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Oncology (AREA)
Virology (AREA)
Communicable Diseases (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Molecular Biology (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Micro-Organisms Or Cultivation Processes Thereof (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

UA2002010361A 1999-06-28 2000-06-20 Respiratory syncytial virus replication inhibitors UA75866C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP99202089		1999-06-28
PCT/EP2000/005677 WO2001000615A1 (en)	1999-06-28	2000-06-20	Respiratory syncytial virus replication inhibitors

Publications (1)

Publication Number	Publication Date
UA75866C2 true UA75866C2 (en)	2006-06-15

Family

ID=8240374

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA2002010361A UA75866C2 (en)	1999-06-28	2000-06-20	Respiratory syncytial virus replication inhibitors

Country Status (34)

Country	Link
US (2)	US7071192B1 (no)
EP (2)	EP1196410B1 (no)
JP (1)	JP2003503403A (no)
KR (1)	KR100731273B1 (no)
CN (1)	CN1171887C (no)
AR (1)	AR024495A1 (no)
AT (2)	ATE259796T1 (no)
AU (1)	AU774829B2 (no)
BG (1)	BG65373B1 (no)
BR (1)	BR0011997A (no)
CA (1)	CA2376785A1 (no)
CZ (1)	CZ20014573A3 (no)
DE (2)	DE60033859T2 (no)
DK (1)	DK1196410T3 (no)
EA (1)	EA004746B1 (no)
EE (1)	EE04592B1 (no)
ES (2)	ES2283716T3 (no)
HK (1)	HK1045998B (no)
HR (2)	HRP20010934A2 (no)
HU (1)	HUP0201789A3 (no)
IL (2)	IL147328A0 (no)
MX (1)	MXPA02000117A (no)
MY (1)	MY129810A (no)
NO (1)	NO321599B1 (no)
NZ (1)	NZ515392A (no)
PL (1)	PL200694B1 (no)
PT (1)	PT1196410E (no)
SI (1)	SI1196410T1 (no)
SK (1)	SK18952001A3 (no)
TR (2)	TR200500707T2 (no)
TW (1)	TWI267513B (no)
UA (1)	UA75866C2 (no)
WO (1)	WO2001000615A1 (no)
ZA (1)	ZA200110473B (no)

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US20040010004A1 (en)	2000-01-17	2004-01-15	Naoki Tsuchiya	Benzimidazole derivatives
BR9912098A (pt)	1998-07-15	2001-09-25	Teijin Ltd	Derivado de tiobenzimidazol, composição farmacêutica, e, agente preventivo e/ou terapêutico
RU2263674C2 (ru) *	2000-01-17	2005-11-10	Тейдзин Лимитед	Бензимидазольное производное, ингибитор человеческой химазы, терапевтический агент и фармацевтическая композиция на его основе
US6489338B2 (en)	2000-06-13	2002-12-03	Bristol-Myers Squibb Company	Imidazopyridine and imidazopyrimidine antiviral agents
US6506738B1 (en)	2000-09-27	2003-01-14	Bristol-Myers Squibb Company	Benzimidazolone antiviral agents
US6919352B2 (en)	2000-12-15	2005-07-19	Smithkline Beecham Corporation	Pyrazolopyridinyl pyridine and pyrimidine therapeutic compounds
DE60112330T2 (de)	2000-12-15	2006-04-13	Glaxo Group Ltd., Greenford	Pyrazolopyridinderivate
US6774134B2 (en)	2000-12-20	2004-08-10	Bristol-Myers Squibb Company	Heterocyclic substituted 2-methyl-benzimidazole antiviral agents
US7153855B2 (en)	2001-03-08	2006-12-26	Smithkline Beecham Corporation	Pyrazolopyridinyl pyrimidine therapeutic compounds
US7034030B2 (en)	2001-03-30	2006-04-25	Smithkline Beecham Corporation	Pyralopyridines, process for their preparation and use as therapeutic compounds
WO2002083672A1 (en)	2001-04-10	2002-10-24	Smithkline Beecham Corporation	Antiviral pyrazolopyridine compounds
ES2242028T3 (es)	2001-04-27	2005-11-01	Smithkline Beecham Corporation	Derivados de pirazolo(1,5-a)piridina.
US7030150B2 (en) *	2001-05-11	2006-04-18	Trimeris, Inc.	Benzimidazole compounds and antiviral uses thereof
CN1518550A (zh)	2001-06-21	2004-08-04	ʷ��˿��ȳ�ķ��޹�˾	用于预防和治疗疱疹病毒感染的咪唑并[1,2-a]吡啶衍生物
JP2005508955A (ja) *	2001-10-05	2005-04-07	スミスクラインビーチャムコーポレーション	ヘルペスウイルス感染の治療で使用されるためのイミダゾ−ピリジン誘導体
US6919331B2 (en)	2001-12-10	2005-07-19	Bristol-Myers Squibb Company	Substituted 2-methyl-benzimidazole respiratory syncytial virus antiviral agents
WO2003050120A1 (en)	2001-12-11	2003-06-19	Smithkline Beecham Corporation	Pyrazolo-pyridine derivatives as antiherpes agents
US7244847B2 (en) *	2002-02-06	2007-07-17	Isis Pharmaceuticals, Inc.	Benzimidazole compounds
EP1539691A2 (en)	2002-08-09	2005-06-15	Viropharma Incorporated	Compounds, compositions and methods for treating or preventing pneumovirus infection and associated diseases
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2000
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Publication number	Publication date
HK1045998A1 (en)	2002-12-20
HRP20080390A2 (en)	2008-12-31
US7407969B2 (en)	2008-08-05
PL352385A1 (en)	2003-08-25
US20060058309A1 (en)	2006-03-16
HK1045998B (zh)	2005-06-03
DE60008382D1 (en)	2004-03-25
SI1196410T1 (en)	2004-08-31
DE60008382T2 (de)	2004-12-02
TR200103805T2 (tr)	2002-06-21
NO321599B1 (no)	2006-06-06
IL147328A0 (en)	2002-08-14
AU774829B2 (en)	2004-07-08
MXPA02000117A (es)	2002-07-02
MY129810A (en)	2007-05-31
EP1400519B1 (en)	2007-03-07
HUP0201789A2 (hu)	2002-11-28
NO20016370D0 (no)	2001-12-27
DE60033859T2 (de)	2007-11-08
ATE259796T1 (de)	2004-03-15
BG106288A (en)	2002-10-31
JP2003503403A (ja)	2003-01-28
ES2215670T3 (es)	2004-10-16
EA004746B1 (ru)	2004-08-26
CZ20014573A3 (cs)	2002-05-15
ZA200110473B (en)	2003-03-20
BR0011997A (pt)	2002-03-05
EP1400519A1 (en)	2004-03-24
CA2376785A1 (en)	2001-01-04
EA200200086A1 (ru)	2002-06-27
CN1171887C (zh)	2004-10-20
EP1196410B1 (en)	2004-02-18
NZ515392A (en)	2004-03-26
HRP20010934A2 (en)	2003-06-30
KR20020000815A (ko)	2002-01-05
TWI267513B (en)	2006-12-01
EE04592B1 (et)	2006-02-15
US7071192B1 (en)	2006-07-04
DE60033859D1 (de)	2007-04-19
SK18952001A3 (sk)	2002-11-06
TR200500707T2 (tr)	2005-04-21
PL200694B1 (pl)	2009-01-30
KR100731273B1 (ko)	2007-06-21
EP1196410A1 (en)	2002-04-17
ES2283716T3 (es)	2007-11-01
AU5222200A (en)	2001-01-31
AR024495A1 (es)	2002-10-02
ATE356121T1 (de)	2007-03-15
WO2001000615A1 (en)	2001-01-04
DK1196410T3 (da)	2004-06-28
WO2001000615A8 (en)	2002-01-10
CN1358182A (zh)	2002-07-10
NO20016370L (no)	2001-12-27
PT1196410E (pt)	2004-07-30
IL147328A (en)	2007-06-03
EE200100694A (et)	2003-02-17
HUP0201789A3 (en)	2003-12-29
BG65373B1 (bg)	2008-04-30

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