ZA200207545B - 4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxamides as antiviral agents. - Google Patents
4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxamides as antiviral agents. Download PDFInfo
- Publication number
- ZA200207545B ZA200207545B ZA200207545A ZA200207545A ZA200207545B ZA 200207545 B ZA200207545 B ZA 200207545B ZA 200207545 A ZA200207545 A ZA 200207545A ZA 200207545 A ZA200207545 A ZA 200207545A ZA 200207545 B ZA200207545 B ZA 200207545B
- Authority
- ZA
- South Africa
- Prior art keywords
- het
- optionally substituted
- aryl
- composition
- substance
- Prior art date
Links
- 239000003443 antiviral agent Substances 0.000 title description 5
- PKMFXPIZWVLGFQ-UHFFFAOYSA-N 4-oxo-1h-1,8-naphthyridine-3-carboxamide Chemical class C1=CC=C2C(=O)C(C(=O)N)=CNC2=N1 PKMFXPIZWVLGFQ-UHFFFAOYSA-N 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 125000001424 substituent group Chemical group 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 44
- 125000005843 halogen group Chemical group 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 34
- -1 cyano, phenyl Chemical group 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 241000124008 Mammalia Species 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 208000036142 Viral infection Diseases 0.000 claims description 12
- 230000009385 viral infection Effects 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- 125000002837 carbocyclic group Chemical group 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Chemical group 0.000 claims description 8
- 241000701085 Human alphaherpesvirus 3 Species 0.000 claims description 7
- 241000701024 Human betaherpesvirus 5 Species 0.000 claims description 7
- 241000701044 Human gammaherpesvirus 4 Species 0.000 claims description 7
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 7
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 241000282414 Homo sapiens Species 0.000 claims description 6
- 241000700588 Human alphaherpesvirus 1 Species 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- 150000001413 amino acids Chemical class 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 6
- 229910052744 lithium Chemical group 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 150000002923 oximes Chemical class 0.000 claims description 6
- 239000011591 potassium Chemical group 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 claims description 5
- 208000029433 Herpesviridae infectious disease Diseases 0.000 claims description 5
- 238000001727 in vivo Methods 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 206010019972 Herpes viral infections Diseases 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000000338 in vitro Methods 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 34
- 230000037396 body weight Effects 0.000 claims 8
- DUDCRNHOLUWPDX-UHFFFAOYSA-N 1,8-naphthyridine-3-carboxamide Chemical compound N1=CC=CC2=CC(C(=O)N)=CN=C21 DUDCRNHOLUWPDX-UHFFFAOYSA-N 0.000 claims 4
- 241001465754 Metazoa Species 0.000 claims 4
- 244000144972 livestock Species 0.000 claims 4
- 108020005202 Viral DNA Proteins 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- AARABBUHQBUCKL-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-1,7-dimethyl-4-oxo-1,8-naphthyridine-3-carboxamide Chemical compound O=C1C=2C=C(C#CCO)C(C)=NC=2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 AARABBUHQBUCKL-UHFFFAOYSA-N 0.000 claims 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- LBESUOBUJYGYIG-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-methyl-4,7-dioxo-8h-1,8-naphthyridine-3-carboxamide Chemical compound O=C1C=2C=CC(=O)NC=2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 LBESUOBUJYGYIG-UHFFFAOYSA-N 0.000 claims 1
- MAHKJZPTWJIXDE-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-7-methoxy-1-methyl-4-oxo-1,8-naphthyridine-3-carboxamide Chemical compound O=C1C=2C=C(C#CCO)C(OC)=NC=2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 MAHKJZPTWJIXDE-UHFFFAOYSA-N 0.000 claims 1
- AWOARZTZSKIEAW-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(3-hydroxypropyl)-7-methoxy-1-methyl-4-oxo-1,8-naphthyridine-3-carboxamide Chemical compound O=C1C=2C=C(CCCO)C(OC)=NC=2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 AWOARZTZSKIEAW-UHFFFAOYSA-N 0.000 claims 1
- GFSWQNIEKORBOY-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-iodo-7-methoxy-1-methyl-4-oxo-1,8-naphthyridine-3-carboxamide Chemical compound O=C1C=2C=C(I)C(OC)=NC=2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 GFSWQNIEKORBOY-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 description 7
- 241001529453 unidentified herpesvirus Species 0.000 description 4
- 230000003612 virological effect Effects 0.000 description 4
- 230000000840 anti-viral effect Effects 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 108010014303 DNA-directed DNA polymerase Proteins 0.000 description 2
- 201000005866 Exanthema Subitum Diseases 0.000 description 2
- 241000701074 Human alphaherpesvirus 2 Species 0.000 description 2
- 241000701041 Human betaherpesvirus 7 Species 0.000 description 2
- 241001502974 Human gammaherpesvirus 8 Species 0.000 description 2
- 241000701027 Human herpesvirus 6 Species 0.000 description 2
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 2
- 206010061598 Immunodeficiency Diseases 0.000 description 2
- 206010025323 Lymphomas Diseases 0.000 description 2
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 description 2
- 208000036485 Roseola Diseases 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 231100000676 disease causative agent Toxicity 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000005058 1,8-naphthyridines Chemical class 0.000 description 1
- IJAVOENDLHVSER-UHFFFAOYSA-N 4-oxo-1h-cinnoline-3-carboxamide Chemical class C1=CC=CC2=C(O)C(C(=O)N)=NN=C21 IJAVOENDLHVSER-UHFFFAOYSA-N 0.000 description 1
- CVAWACBLSANHSQ-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxamide Chemical class C1=CC=CC2=C(O)C(C(=O)N)=CN=C21 CVAWACBLSANHSQ-UHFFFAOYSA-N 0.000 description 1
- 208000011691 Burkitt lymphomas Diseases 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 201000006082 Chickenpox Diseases 0.000 description 1
- 208000032170 Congenital Abnormalities Diseases 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 102000053602 DNA Human genes 0.000 description 1
- 241000450599 DNA viruses Species 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 208000007514 Herpes zoster Diseases 0.000 description 1
- 208000017604 Hodgkin disease Diseases 0.000 description 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 208000034578 Multiple myelomas Diseases 0.000 description 1
- 208000002454 Nasopharyngeal Carcinoma Diseases 0.000 description 1
- 206010061306 Nasopharyngeal cancer Diseases 0.000 description 1
- 208000037581 Persistent Infection Diseases 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 206010038910 Retinitis Diseases 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 241000700584 Simplexvirus Species 0.000 description 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 1
- 206010046980 Varicella Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000007698 birth defect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 208000010643 digestive system disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 208000018685 gastrointestinal system disease Diseases 0.000 description 1
- 210000004392 genitalia Anatomy 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 201000006747 infectious mononucleosis Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 201000011216 nasopharynx carcinoma Diseases 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 102000003390 tumor necrosis factor Human genes 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19097900P | 2000-03-21 | 2000-03-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200207545B true ZA200207545B (en) | 2003-12-19 |
Family
ID=22703594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200207545A ZA200207545B (en) | 2000-03-21 | 2002-09-19 | 4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxamides as antiviral agents. |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US6451811B2 (fr) |
| EP (1) | EP1265895A1 (fr) |
| JP (1) | JP2003529601A (fr) |
| KR (1) | KR20020093849A (fr) |
| CN (1) | CN1416430A (fr) |
| AR (1) | AR030194A1 (fr) |
| AU (1) | AU2001243240A1 (fr) |
| BR (1) | BR0108803A (fr) |
| CA (1) | CA2400057A1 (fr) |
| HK (1) | HK1054235A1 (fr) |
| MX (1) | MXPA02009249A (fr) |
| NZ (1) | NZ521522A (fr) |
| WO (1) | WO2001074816A1 (fr) |
| ZA (1) | ZA200207545B (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2150544B1 (fr) * | 2007-03-19 | 2016-01-13 | Takeda Pharmaceutical Company Limited | Inhibiteurs de mapk/erk kinase |
| US20110166123A1 (en) * | 2008-01-07 | 2011-07-07 | Aardea Biosciences, Inc. | Novel compositions and methods of use |
| EP2855479B1 (fr) | 2012-04-05 | 2016-03-30 | Boehringer Ingelheim International GmbH | Dérivés 1,8-naphthyridin-2(1h)-one comme inhibiteurs de cytomégalovirus |
| US9315499B2 (en) | 2012-04-05 | 2016-04-19 | Boehringer Ingelheim International Gmbh | Cytomegalovirus inhibitor compounds |
| AU2017362347B2 (en) | 2016-11-17 | 2020-09-03 | The Gillette Company Llc | Skin engaging member comprising ethylene vinyl acetate and a fragrance |
| WO2020053654A1 (fr) | 2018-09-12 | 2020-03-19 | Novartis Ag | Composés antiviraux de pyridopyrazinedione |
| KR20220070005A (ko) | 2019-09-26 | 2022-05-27 | 노파르티스 아게 | 항바이러스성 피라졸로피리디논 화합물 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4568649A (en) | 1983-02-22 | 1986-02-04 | Immunex Corporation | Immediate ligand detection assay |
| US4559157A (en) | 1983-04-21 | 1985-12-17 | Creative Products Resource Associates, Ltd. | Cosmetic applicator useful for skin moisturizing |
| LU84979A1 (fr) | 1983-08-30 | 1985-04-24 | Oreal | Composition cosmetique ou pharmaceutique sous forme aqueuse ou anhydre dont la phase grasse contient un polyether oligomere et polyethers oligomeres nouveaux |
| GB8513639D0 (en) | 1985-05-30 | 1985-07-03 | Ici America Inc | Cinnoline compounds |
| GB8702288D0 (en) | 1987-02-02 | 1987-03-11 | Erba Farmitalia | Cinnoline-carboxamides |
| US4820508A (en) | 1987-06-23 | 1989-04-11 | Neutrogena Corporation | Skin protective composition |
| US4992478A (en) | 1988-04-04 | 1991-02-12 | Warner-Lambert Company | Antiinflammatory skin moisturizing composition and method of preparing same |
| US4938949A (en) | 1988-09-12 | 1990-07-03 | University Of New York | Treatment of damaged bone marrow and dosage units therefor |
| US4959363A (en) * | 1989-06-23 | 1990-09-25 | Sterling Drug Inc. | Quinolonecarboxamide compounds, their preparation and use as antivirals. |
| MX9800921A (es) | 1995-08-02 | 1998-05-31 | Chirotech Technology Ltd | Quinolonas y su uso terapeutico. |
| WO1997004779A1 (fr) | 1995-08-02 | 1997-02-13 | Chiroscience Limited | Quinolones et leur utilisation therapeutique |
| JP2002505660A (ja) | 1996-09-10 | 2002-02-19 | ファルマシア・アンド・アップジョン・カンパニー | 抗ウィルス剤としての８―ヒドロキシ―７―置換キノリン |
| HUP0001054A3 (en) | 1997-08-06 | 2001-01-29 | Daiichi Asubio Pharma Co Ltd | 1-aryl-1,8-naphthyridin-4-one derivative as type iv phosphodiesterase inhibitor |
| US6093732A (en) * | 1997-12-22 | 2000-07-25 | Pharmacia & Upjohn Company | 4-hydroxyquinoline-3-carboxamides and hydrazides as antiviral agents |
| US6331548B1 (en) | 1998-01-29 | 2001-12-18 | Suntory Limited | 1-cycloalkyl-1,8-naphthyridin-4-one derivative as type IV phosphodiesterase inhibitor |
-
2001
- 2001-03-15 KR KR1020027012468A patent/KR20020093849A/ko not_active Application Discontinuation
- 2001-03-15 CN CN01806209A patent/CN1416430A/zh active Pending
- 2001-03-15 MX MXPA02009249A patent/MXPA02009249A/es active IP Right Grant
- 2001-03-15 CA CA002400057A patent/CA2400057A1/fr not_active Abandoned
- 2001-03-15 WO PCT/US2001/005808 patent/WO2001074816A1/fr not_active Application Discontinuation
- 2001-03-15 BR BR0108803-3A patent/BR0108803A/pt not_active IP Right Cessation
- 2001-03-15 AU AU2001243240A patent/AU2001243240A1/en not_active Abandoned
- 2001-03-15 EP EP01916183A patent/EP1265895A1/fr not_active Withdrawn
- 2001-03-15 JP JP2001572506A patent/JP2003529601A/ja active Pending
- 2001-03-15 US US09/808,757 patent/US6451811B2/en not_active Expired - Fee Related
- 2001-03-15 NZ NZ521522A patent/NZ521522A/en unknown
- 2001-03-20 AR ARP010101301A patent/AR030194A1/es not_active Application Discontinuation
-
2002
- 2002-05-20 US US10/151,439 patent/US6693114B2/en not_active Expired - Fee Related
- 2002-09-19 ZA ZA200207545A patent/ZA200207545B/en unknown
-
2003
- 2003-09-11 HK HK03106506.1A patent/HK1054235A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US6451811B2 (en) | 2002-09-17 |
| MXPA02009249A (es) | 2003-03-12 |
| JP2003529601A (ja) | 2003-10-07 |
| US20020177604A1 (en) | 2002-11-28 |
| AR030194A1 (es) | 2003-08-13 |
| KR20020093849A (ko) | 2002-12-16 |
| US20020019413A1 (en) | 2002-02-14 |
| HK1054235A1 (zh) | 2003-11-21 |
| AU2001243240A1 (en) | 2001-10-15 |
| US6693114B2 (en) | 2004-02-17 |
| WO2001074816A1 (fr) | 2001-10-11 |
| CN1416430A (zh) | 2003-05-07 |
| NZ521522A (en) | 2004-08-27 |
| CA2400057A1 (fr) | 2001-10-11 |
| BR0108803A (pt) | 2002-11-05 |
| EP1265895A1 (fr) | 2002-12-18 |
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