UA75866C2 - Respiratory syncytial virus replication inhibitors - Google Patents
Respiratory syncytial virus replication inhibitors Download PDFInfo
- Publication number
- UA75866C2 UA75866C2 UA2002010361A UA2002010361A UA75866C2 UA 75866 C2 UA75866 C2 UA 75866C2 UA 2002010361 A UA2002010361 A UA 2002010361A UA 2002010361 A UA2002010361 A UA 2002010361A UA 75866 C2 UA75866 C2 UA 75866C2
- Authority
- UA
- Ukraine
- Prior art keywords
- formula
- hydrogen
- piperidinyl
- сно
- intermediate compound
- Prior art date
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- 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
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- 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
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
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- 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
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- 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
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- 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
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 76
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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
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
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Classifications
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- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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 |
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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 (hr) |
| EP (2) | EP1196410B1 (hr) |
| JP (1) | JP2003503403A (hr) |
| KR (1) | KR100731273B1 (hr) |
| CN (1) | CN1171887C (hr) |
| AR (1) | AR024495A1 (hr) |
| AT (2) | ATE259796T1 (hr) |
| AU (1) | AU774829B2 (hr) |
| BG (1) | BG65373B1 (hr) |
| BR (1) | BR0011997A (hr) |
| CA (1) | CA2376785A1 (hr) |
| CZ (1) | CZ20014573A3 (hr) |
| DE (2) | DE60008382T2 (hr) |
| DK (1) | DK1196410T3 (hr) |
| EA (1) | EA004746B1 (hr) |
| EE (1) | EE04592B1 (hr) |
| ES (2) | ES2215670T3 (hr) |
| HK (1) | HK1045998B (hr) |
| HR (2) | HRP20010934A2 (hr) |
| HU (1) | HUP0201789A3 (hr) |
| IL (2) | IL147328A0 (hr) |
| MX (1) | MXPA02000117A (hr) |
| MY (1) | MY129810A (hr) |
| NO (1) | NO321599B1 (hr) |
| NZ (1) | NZ515392A (hr) |
| PL (1) | PL200694B1 (hr) |
| PT (1) | PT1196410E (hr) |
| SI (1) | SI1196410T1 (hr) |
| SK (1) | SK18952001A3 (hr) |
| TR (2) | TR200500707T2 (hr) |
| TW (1) | TWI267513B (hr) |
| UA (1) | UA75866C2 (hr) |
| WO (1) | WO2001000615A1 (hr) |
| ZA (1) | ZA200110473B (hr) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6495580B1 (en) | 1998-01-29 | 2002-12-17 | Viropharma Incorporated | Compounds, compositions and methods for treating or preventing pneumovirus infection and associated diseases |
| US20040010004A1 (en) | 2000-01-17 | 2004-01-15 | Naoki Tsuchiya | Benzimidazole derivatives |
| WO2000003997A1 (fr) | 1998-07-15 | 2000-01-27 | Teijin Limited | Derives de thiobenzimidazole |
| DK1249450T3 (da) * | 2000-01-17 | 2008-02-11 | Teijin Pharma Ltd | Benzimidazolderivater som human chymase-inhibitorer |
| 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 |
| DE60112330T2 (de) | 2000-12-15 | 2006-04-13 | Glaxo Group Ltd., Greenford | Pyrazolopyridinderivate |
| US6919352B2 (en) | 2000-12-15 | 2005-07-19 | Smithkline Beecham Corporation | Pyrazolopyridinyl pyridine and pyrimidine therapeutic compounds |
| US6774134B2 (en) | 2000-12-20 | 2004-08-10 | Bristol-Myers Squibb Company | Heterocyclic substituted 2-methyl-benzimidazole antiviral agents |
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