SK101697A3 - Novel coumarin quinolone carboxylic acids and processes for the preparation thereof - Google Patents
Novel coumarin quinolone carboxylic acids and processes for the preparation thereof Download PDFInfo
- Publication number
- SK101697A3 SK101697A3 SK1016-97A SK101697A SK101697A3 SK 101697 A3 SK101697 A3 SK 101697A3 SK 101697 A SK101697 A SK 101697A SK 101697 A3 SK101697 A3 SK 101697A3
- Authority
- SK
- Slovakia
- Prior art keywords
- nhch
- formula
- compound
- chnh
- benzopyrano
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- AEEFWKGWOPFEDT-UHFFFAOYSA-N chromen-2-one 2-oxo-1H-quinoline-3-carboxylic acid Chemical class C1=CC=C2OC(=O)C=CC2=C1.C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 AEEFWKGWOPFEDT-UHFFFAOYSA-N 0.000 title abstract 3
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229960000956 coumarin Drugs 0.000 claims abstract description 3
- 235000001671 coumarin Nutrition 0.000 claims abstract description 3
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 150000001735 carboxylic acids Chemical class 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 6
- 230000000259 anti-tumor effect Effects 0.000 claims description 3
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 1
- 230000000845 anti-microbial effect Effects 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 230000031018 biological processes and functions Effects 0.000 abstract 1
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 abstract 1
- 238000004458 analytical method Methods 0.000 description 15
- 239000002253 acid Substances 0.000 description 12
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 230000035484 reaction time Effects 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 230000012010 growth Effects 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 8
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 241000588724 Escherichia coli Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 210000002950 fibroblast Anatomy 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 244000063299 Bacillus subtilis Species 0.000 description 2
- 235000014469 Bacillus subtilis Nutrition 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 2
- 206010008342 Cervix carcinoma Diseases 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 206010023825 Laryngeal cancer Diseases 0.000 description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 201000010881 cervical cancer Diseases 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- ONJZRBLUIQDRLI-UHFFFAOYSA-N chromen-2-one propanedioic acid Chemical class OC(=O)CC(O)=O.C1=CC=C2OC(=O)C=CC2=C1 ONJZRBLUIQDRLI-UHFFFAOYSA-N 0.000 description 2
- -1 coumarin malonate ester Chemical class 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- OQYNXVQXCSVEPP-UHFFFAOYSA-N ethyl 3-hydroxy-4,7-dioxo-2,6-dihydropyrano[2,3-g]quinoline-3-carboxylate Chemical compound C1=CC(=O)NC2=C1C=C1OCC(C(=O)OCC)(O)C(=O)C1=C2 OQYNXVQXCSVEPP-UHFFFAOYSA-N 0.000 description 2
- FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 206010023841 laryngeal neoplasm Diseases 0.000 description 2
- 201000004962 larynx cancer Diseases 0.000 description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000001968 nicotinic acid Nutrition 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 201000002528 pancreatic cancer Diseases 0.000 description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MBHJMTNAZYLKTB-UHFFFAOYSA-N 2H-pyrano[2,3-g]quinoline-3-carboxylic acid Chemical compound O1CC(=CC=2C1=CC=1C(=NC=CC=1)C=2)C(=O)O MBHJMTNAZYLKTB-UHFFFAOYSA-N 0.000 description 1
- SERVTOXIOYSDQO-UHFFFAOYSA-N 2h-chromen-2-ol Chemical compound C1=CC=C2C=CC(O)OC2=C1 SERVTOXIOYSDQO-UHFFFAOYSA-N 0.000 description 1
- GIDXFXZGPLMGCH-UHFFFAOYSA-N 4,5-dioxo-1h-chromeno[4,3-b]pyridine-3-carboxylic acid Chemical compound C12=CC=CC=C2OC(=O)C2=C1NC=C(C(=O)O)C2=O GIDXFXZGPLMGCH-UHFFFAOYSA-N 0.000 description 1
- MOZYQMRRCLGEIX-UHFFFAOYSA-N 7-fluoro-1,5-dioxo-4h-chromeno[3,4-b]pyridine-2-carboxylic acid Chemical compound C1=CC(F)=C2OC(=O)C(NC=C(C3=O)C(=O)O)=C3C2=C1 MOZYQMRRCLGEIX-UHFFFAOYSA-N 0.000 description 1
- 241000194103 Bacillus pumilus Species 0.000 description 1
- 240000001817 Cereus hexagonus Species 0.000 description 1
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241000943303 Enterococcus faecalis ATCC 29212 Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000515012 Micrococcus flavus Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241001148137 Salmonella enterica subsp. enterica serovar Panama Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 1
- 238000007922 dissolution test Methods 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- ZQVMCLBNBIBRGM-UHFFFAOYSA-N ethyl 1,5-dioxo-4h-chromeno[3,4-b]pyridine-2-carboxylate Chemical compound C1=CC=C2OC(=O)C(NC=C(C3=O)C(=O)OCC)=C3C2=C1 ZQVMCLBNBIBRGM-UHFFFAOYSA-N 0.000 description 1
- MNLARMGWWCGCLU-UHFFFAOYSA-N ethyl 7-fluoro-1,5-dioxo-4h-chromeno[3,4-b]pyridine-2-carboxylate Chemical compound C1=CC(F)=C2OC(=O)C(NC=C(C3=O)C(=O)OCC)=C3C2=C1 MNLARMGWWCGCLU-UHFFFAOYSA-N 0.000 description 1
- KNAPZAUWFKJYGM-UHFFFAOYSA-N ethyl 9-nitro-1,5-dioxo-4h-chromeno[3,4-b]pyridine-2-carboxylate Chemical compound [O-][N+](=O)C1=CC=C2OC(=O)C(NC=C(C3=O)C(=O)OCC)=C3C2=C1 KNAPZAUWFKJYGM-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000005918 in vitro anti-tumor Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-M nicotinate Chemical compound [O-]C(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-M 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 description 1
- 229960001180 norfloxacin Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HR960352A HRP960352A2 (en) | 1996-07-26 | 1996-07-26 | Novel coumarin quinoline carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK101697A3 true SK101697A3 (en) | 1998-05-06 |
Family
ID=10946437
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1016-97A SK101697A3 (en) | 1996-07-26 | 1997-07-24 | Novel coumarin quinolone carboxylic acids and processes for the preparation thereof |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5908933A (zh) |
| EP (1) | EP0820998B1 (zh) |
| JP (1) | JPH1087668A (zh) |
| CN (1) | CN1075500C (zh) |
| AT (1) | ATE205211T1 (zh) |
| BG (1) | BG63085B1 (zh) |
| CA (1) | CA2210448A1 (zh) |
| CZ (1) | CZ238297A3 (zh) |
| DE (1) | DE69706487T2 (zh) |
| ES (1) | ES2163694T3 (zh) |
| HR (1) | HRP960352A2 (zh) |
| HU (1) | HUP9701298A3 (zh) |
| PL (1) | PL321308A1 (zh) |
| PT (1) | PT820998E (zh) |
| RU (1) | RU2166504C2 (zh) |
| SI (1) | SI9700197B (zh) |
| SK (1) | SK101697A3 (zh) |
| UA (1) | UA45383C2 (zh) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP960308A2 (en) * | 1996-07-02 | 1998-08-31 | Ljerka Poljak | New coumarine derivatives, process for the preparation thereof and their use |
| PL349348A1 (en) * | 1999-01-13 | 2002-07-15 | Millennium Pharmaceuticals | Functionalized heterocycles as chemokine receptor modulators |
| DE60203029T2 (de) * | 2001-06-28 | 2006-02-23 | Dainippon Ink And Chemicals, Inc. | Benzopyran Derivate und diese enthaltende antiallergische Mittel |
| FR2827864B1 (fr) * | 2001-07-25 | 2005-09-16 | Servier Lab | Nouveaux derives de benzo[b]pyrano[3,2-h]acridin-7-one, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US8058427B2 (en) * | 2008-06-12 | 2011-11-15 | National Health Research Institutes | Coumarin compounds and their use for treating cancer |
| CN105218531B (zh) * | 2015-10-14 | 2018-03-16 | 西南大学 | 香豆素喹诺酮杂合体或其可药用盐及其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4060619A (en) * | 1976-01-14 | 1977-11-29 | Ayerst Mckenna And Harrison Ltd. | 1,4-Dihydro-4-oxo-benzothiopyrano (4,3-b)pyridine-2-carboxylates and derivatives |
| US4198511A (en) * | 1979-03-21 | 1980-04-15 | Warner-Lambert Company | 1,5-Dihydro-1,5-dioxo-N-1H-tetrazol-5-yl-4H-[1]benzopyrano[3,4-b]pyridine-3-carboxamides and process thereof |
| US4210758A (en) * | 1979-03-21 | 1980-07-01 | Warner-Lambert Company | 1,5-Dihydro-1,5-dioxo-N-1H-tetrazol-5-yl-4H-[1]benzopyrano[3,4-b]pyridine-2-carboxamides |
| GB9306062D0 (en) * | 1993-03-24 | 1993-05-12 | Lilly Industries Ltd | Pharmaceutical compounds |
| US5688810A (en) * | 1994-12-22 | 1997-11-18 | Ligand Pharmaceuticals Incorporated | Steroid receptor modulator compounds and methods |
-
1996
- 1996-07-26 HR HR960352A patent/HRP960352A2/hr not_active Application Discontinuation
-
1997
- 1997-07-18 US US08/897,057 patent/US5908933A/en not_active Expired - Fee Related
- 1997-07-23 SI SI9700197A patent/SI9700197B/sl unknown
- 1997-07-24 PT PT97112743T patent/PT820998E/pt unknown
- 1997-07-24 EP EP97112743A patent/EP0820998B1/en not_active Expired - Lifetime
- 1997-07-24 SK SK1016-97A patent/SK101697A3/sk unknown
- 1997-07-24 AT AT97112743T patent/ATE205211T1/de not_active IP Right Cessation
- 1997-07-24 JP JP9198505A patent/JPH1087668A/ja active Pending
- 1997-07-24 ES ES97112743T patent/ES2163694T3/es not_active Expired - Lifetime
- 1997-07-24 PL PL97321308A patent/PL321308A1/xx unknown
- 1997-07-24 DE DE69706487T patent/DE69706487T2/de not_active Expired - Fee Related
- 1997-07-24 CA CA002210448A patent/CA2210448A1/en not_active Abandoned
- 1997-07-25 HU HU9701298A patent/HUP9701298A3/hu unknown
- 1997-07-25 RU RU97113254/04A patent/RU2166504C2/ru active
- 1997-07-25 UA UA97073970A patent/UA45383C2/uk unknown
- 1997-07-25 BG BG101796A patent/BG63085B1/bg unknown
- 1997-07-25 CN CN97117456A patent/CN1075500C/zh not_active Expired - Fee Related
- 1997-07-25 CZ CZ972382A patent/CZ238297A3/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SI9700197A (sl) | 1998-02-28 |
| RU2166504C2 (ru) | 2001-05-10 |
| SI9700197B (sl) | 2002-02-28 |
| PT820998E (pt) | 2002-02-28 |
| HUP9701298A2 (hu) | 1999-06-28 |
| CZ238297A3 (cs) | 1998-03-18 |
| JPH1087668A (ja) | 1998-04-07 |
| CN1176252A (zh) | 1998-03-18 |
| UA45383C2 (uk) | 2002-04-15 |
| HRP960352A2 (en) | 1998-08-31 |
| HUP9701298A3 (en) | 1999-07-28 |
| CN1075500C (zh) | 2001-11-28 |
| EP0820998A3 (en) | 1998-04-29 |
| ES2163694T3 (es) | 2002-02-01 |
| ATE205211T1 (de) | 2001-09-15 |
| EP0820998A2 (en) | 1998-01-28 |
| EP0820998B1 (en) | 2001-09-05 |
| BG63085B1 (bg) | 2001-03-30 |
| CA2210448A1 (en) | 1998-01-26 |
| US5908933A (en) | 1999-06-01 |
| HU9701298D0 (en) | 1997-09-29 |
| DE69706487D1 (de) | 2001-10-11 |
| BG101796A (en) | 1998-10-30 |
| PL321308A1 (en) | 1998-02-02 |
| DE69706487T2 (de) | 2002-05-08 |
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