KR20080106525A - 유기 화합물 - Google Patents
유기 화합물 Download PDFInfo
- Publication number
- KR20080106525A KR20080106525A KR1020087020597A KR20087020597A KR20080106525A KR 20080106525 A KR20080106525 A KR 20080106525A KR 1020087020597 A KR1020087020597 A KR 1020087020597A KR 20087020597 A KR20087020597 A KR 20087020597A KR 20080106525 A KR20080106525 A KR 20080106525A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- alkyl
- thia
- aza
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
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- 150000002894 organic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 132
- 239000000203 mixture Substances 0.000 claims abstract description 104
- 241001465754 Metazoa Species 0.000 claims abstract description 67
- 238000000034 method Methods 0.000 claims abstract description 53
- 208000002193 Pain Diseases 0.000 claims abstract description 52
- 230000036407 pain Effects 0.000 claims abstract description 49
- 238000011282 treatment Methods 0.000 claims abstract description 47
- 206010003246 arthritis Diseases 0.000 claims abstract description 38
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 36
- 238000002360 preparation method Methods 0.000 claims abstract description 31
- 230000004054 inflammatory process Effects 0.000 claims abstract description 22
- 206010061218 Inflammation Diseases 0.000 claims abstract description 20
- -1 amino, amino Chemical group 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 48
- 241000282412 Homo Species 0.000 claims description 28
- 150000002148 esters Chemical class 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- 239000002671 adjuvant Substances 0.000 claims description 12
- 239000000969 carrier Substances 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 10
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 7
- 239000006186 oral dosage form Substances 0.000 claims description 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- UXNUAPAXTLFKIZ-UHFFFAOYSA-N 2-(2,7-dichloro-4-methoxythieno[3,2-c][1]benzazepin-10-ylidene)acetic acid Chemical compound COC1=NC2=CC(Cl)=CC=C2C(=CC(O)=O)C2=C1C=C(Cl)S2 UXNUAPAXTLFKIZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 239000002552 dosage form Substances 0.000 claims description 5
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 2
- FJDXAGHBGFNZRJ-UHFFFAOYSA-N 2-(2,7-dichloro-4-ethoxythieno[3,2-c][1]benzazepin-10-ylidene)acetic acid Chemical compound CCOC1=NC2=CC(Cl)=CC=C2C(=CC(O)=O)C2=C1C=C(Cl)S2 FJDXAGHBGFNZRJ-UHFFFAOYSA-N 0.000 claims description 2
- WBLRAUZCGTWGTP-UHFFFAOYSA-N 2-(2,7-dichloro-4-oxo-5h-thieno[3,2-c][1]benzazepin-10-ylidene)acetic acid Chemical compound O=C1NC2=CC(Cl)=CC=C2C(=CC(=O)O)C2=C1C=C(Cl)S2 WBLRAUZCGTWGTP-UHFFFAOYSA-N 0.000 claims description 2
- ASEWOQKMDZAFII-UHFFFAOYSA-N 2-(2,7-difluoro-4-methoxythieno[3,2-c][1]benzazepin-10-ylidene)acetic acid Chemical compound COC1=NC2=CC(F)=CC=C2C(=CC(O)=O)C2=C1C=C(F)S2 ASEWOQKMDZAFII-UHFFFAOYSA-N 0.000 claims description 2
- VQROHRUWTICCSC-UHFFFAOYSA-N 2-(2,7-difluoro-4-oxo-5h-thieno[3,2-c][1]benzazepin-10-ylidene)acetic acid Chemical compound O=C1NC2=CC(F)=CC=C2C(=CC(=O)O)C2=C1C=C(F)S2 VQROHRUWTICCSC-UHFFFAOYSA-N 0.000 claims description 2
- OXERCZMJFFKEGU-UHFFFAOYSA-N 2-(2-chloro-4-ethoxy-7-fluorothieno[3,2-c][1]benzazepin-10-ylidene)acetic acid Chemical compound CCOC1=NC2=CC(F)=CC=C2C(=CC(O)=O)C2=C1C=C(Cl)S2 OXERCZMJFFKEGU-UHFFFAOYSA-N 0.000 claims description 2
- YQPVGONBHYUGEJ-UHFFFAOYSA-N 2-(2-chloro-4-ethoxythieno[3,2-c][1]benzazepin-10-ylidene)acetic acid Chemical compound CCOC1=NC2=CC=CC=C2C(=CC(O)=O)C2=C1C=C(Cl)S2 YQPVGONBHYUGEJ-UHFFFAOYSA-N 0.000 claims description 2
- UHQGCNJXTQOKLU-UHFFFAOYSA-N 2-(2-chloro-4-methoxythieno[3,2-c][1]benzazepin-10-ylidene)acetic acid Chemical compound COC1=NC2=CC=CC=C2C(=CC(O)=O)C2=C1C=C(Cl)S2 UHQGCNJXTQOKLU-UHFFFAOYSA-N 0.000 claims description 2
- WTLOBSBAQGENTG-UHFFFAOYSA-N 2-(2-chloro-4-oxo-5h-thieno[3,2-c][1]benzazepin-10-ylidene)acetic acid Chemical compound O=C1NC2=CC=CC=C2C(=CC(=O)O)C2=C1C=C(Cl)S2 WTLOBSBAQGENTG-UHFFFAOYSA-N 0.000 claims description 2
- HIOVITYFVAJSEY-UHFFFAOYSA-N 2-(2-chloro-7-fluoro-4-methoxythieno[3,2-c][1]benzazepin-10-ylidene)acetic acid Chemical compound COC1=NC2=CC(F)=CC=C2C(=CC(O)=O)C2=C1C=C(Cl)S2 HIOVITYFVAJSEY-UHFFFAOYSA-N 0.000 claims description 2
- MJCDEPQEBDVZLR-UHFFFAOYSA-N 2-(2-chloro-7-fluoro-4-oxo-5h-thieno[3,2-c][1]benzazepin-10-ylidene)acetic acid Chemical compound O=C1NC2=CC(F)=CC=C2C(=CC(=O)O)C2=C1C=C(Cl)S2 MJCDEPQEBDVZLR-UHFFFAOYSA-N 0.000 claims description 2
- VUHGDQUSRVEKSR-UHFFFAOYSA-N 2-(4-ethoxy-2,7-difluorothieno[3,2-c][1]benzazepin-10-ylidene)acetic acid Chemical compound CCOC1=NC2=CC(F)=CC=C2C(=CC(O)=O)C2=C1C=C(F)S2 VUHGDQUSRVEKSR-UHFFFAOYSA-N 0.000 claims description 2
- YBHBZMCZDWWULG-UHFFFAOYSA-N 2-(7-chloro-4-ethoxythieno[3,2-c][1]benzazepin-10-ylidene)acetic acid Chemical compound CCOC1=NC2=CC(Cl)=CC=C2C(=CC(O)=O)C2=C1C=CS2 YBHBZMCZDWWULG-UHFFFAOYSA-N 0.000 claims description 2
- LALRPSSMPWOSMI-UHFFFAOYSA-N 2-(7-chloro-4-methoxythieno[3,2-c][1]benzazepin-10-ylidene)acetic acid Chemical compound COC1=NC2=CC(Cl)=CC=C2C(=CC(O)=O)C2=C1C=CS2 LALRPSSMPWOSMI-UHFFFAOYSA-N 0.000 claims description 2
- UYENDJRGLPJPMO-UHFFFAOYSA-N 2-(7-chloro-4-oxo-5h-thieno[3,2-c][1]benzazepin-10-ylidene)acetic acid Chemical compound O=C1NC2=CC(Cl)=CC=C2C(=CC(=O)O)C2=C1C=CS2 UYENDJRGLPJPMO-UHFFFAOYSA-N 0.000 claims description 2
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 230000001754 anti-pyretic effect Effects 0.000 claims 1
- 239000002221 antipyretic Substances 0.000 claims 1
- 239000006211 transdermal dosage form Substances 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 38
- 201000010099 disease Diseases 0.000 abstract description 36
- 208000038016 acute inflammation Diseases 0.000 abstract description 8
- 230000006022 acute inflammation Effects 0.000 abstract description 8
- 239000000575 pesticide Substances 0.000 description 68
- 241000282472 Canis lupus familiaris Species 0.000 description 53
- 239000004480 active ingredient Substances 0.000 description 49
- 229940126062 Compound A Drugs 0.000 description 42
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 42
- 235000002639 sodium chloride Nutrition 0.000 description 28
- 239000003826 tablet Substances 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 230000000694 effects Effects 0.000 description 23
- 210000001503 joint Anatomy 0.000 description 23
- 206010042674 Swelling Diseases 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- 230000008961 swelling Effects 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 201000008482 osteoarthritis Diseases 0.000 description 19
- 239000000725 suspension Substances 0.000 description 19
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 17
- 229960001259 diclofenac Drugs 0.000 description 16
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
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- 239000002904 solvent Substances 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 241000283086 Equidae Species 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 208000009386 Experimental Arthritis Diseases 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000454 talc Substances 0.000 description 12
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 11
- 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 11
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- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 10
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
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- 235000019359 magnesium stearate Nutrition 0.000 description 9
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 9
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- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
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- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06003702 | 2006-02-23 | ||
| EP06003702.5 | 2006-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20080106525A true KR20080106525A (ko) | 2008-12-08 |
Family
ID=36282923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020087020597A Withdrawn KR20080106525A (ko) | 2006-02-23 | 2007-02-21 | 유기 화합물 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US8258128B2 (enExample) |
| EP (1) | EP1989209B1 (enExample) |
| JP (1) | JP5135233B2 (enExample) |
| KR (1) | KR20080106525A (enExample) |
| CN (1) | CN101389633B (enExample) |
| AR (1) | AR059597A1 (enExample) |
| AU (1) | AU2007218166B9 (enExample) |
| BR (1) | BRPI0708251A2 (enExample) |
| CA (1) | CA2640488C (enExample) |
| ES (1) | ES2540089T3 (enExample) |
| IL (1) | IL192928A0 (enExample) |
| MX (1) | MX2008010834A (enExample) |
| NO (1) | NO20083558L (enExample) |
| NZ (1) | NZ569551A (enExample) |
| RU (1) | RU2430921C2 (enExample) |
| TW (1) | TW200808810A (enExample) |
| WO (1) | WO2007096150A2 (enExample) |
| ZA (1) | ZA200805331B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200808810A (en) | 2006-02-23 | 2008-02-16 | Novartis Ag | Organic compounds |
| IT1391792B1 (it) * | 2008-11-21 | 2012-01-27 | Forem Pharma S R L | Composizione per un integratore naturale alimentare, particolarmente per favorire la fisiologica funzionalita' delle cartilagini. |
| CN105727249A (zh) * | 2016-03-24 | 2016-07-06 | 河南牧业经济学院 | 治疗猫、犬关节病症的外用膏剂及其制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2128029B1 (enExample) * | 1971-03-01 | 1974-08-02 | Roussel Uclaf | |
| BE791902A (fr) | 1971-11-26 | 1973-05-24 | Wander Ag Dr A | Nouveaux derives de la thieno (3,2-c) (1)benzazepine, leur preparation et leur application comme medicaments |
| DE2918778A1 (de) * | 1979-05-10 | 1980-11-20 | Basf Ag | 6-substituierte 11-alkylen-morphantridine |
| DE2918832A1 (de) * | 1979-05-10 | 1980-11-20 | Basf Ag | 5,6-dihydro-11-alkylen-morphantridin- 6-one |
| HU195800B (en) * | 1983-10-13 | 1988-07-28 | Sandoz Ltd | Process for producing 4h-benzo/4,5/cylopenta/1,2-b/ thiofene derivatives and pharmaceutical compositions containing them |
| DE3524744A1 (de) * | 1985-07-11 | 1987-01-15 | Basf Ag | 4-substituierte 10-cyanmethylen-thieno (4,3-e)-benzo-azepine |
| JP2766266B2 (ja) * | 1988-06-20 | 1998-06-18 | 協和醗酵工業株式会社 | ピリジン誘導体およびその中間体 |
| SE9901530D0 (sv) | 1999-04-28 | 1999-04-28 | Astra Pharma Prod | Novel compounds |
| SE9901901D0 (sv) | 1999-05-26 | 1999-05-26 | Astra Ab | Compounds |
| TW200808810A (en) | 2006-02-23 | 2008-02-16 | Novartis Ag | Organic compounds |
-
2007
- 2007-02-16 TW TW096106330A patent/TW200808810A/zh unknown
- 2007-02-21 US US12/224,734 patent/US8258128B2/en not_active Expired - Fee Related
- 2007-02-21 BR BRPI0708251-7A patent/BRPI0708251A2/pt not_active IP Right Cessation
- 2007-02-21 NZ NZ569551A patent/NZ569551A/en not_active IP Right Cessation
- 2007-02-21 EP EP07722883.1A patent/EP1989209B1/en not_active Not-in-force
- 2007-02-21 AU AU2007218166A patent/AU2007218166B9/en not_active Ceased
- 2007-02-21 MX MX2008010834A patent/MX2008010834A/es active IP Right Grant
- 2007-02-21 KR KR1020087020597A patent/KR20080106525A/ko not_active Withdrawn
- 2007-02-21 CA CA2640488A patent/CA2640488C/en not_active Expired - Fee Related
- 2007-02-21 WO PCT/EP2007/001507 patent/WO2007096150A2/en not_active Ceased
- 2007-02-21 RU RU2008137533/04A patent/RU2430921C2/ru not_active IP Right Cessation
- 2007-02-21 JP JP2008555694A patent/JP5135233B2/ja not_active Expired - Fee Related
- 2007-02-21 AR ARP070100731A patent/AR059597A1/es not_active Application Discontinuation
- 2007-02-21 ES ES07722883.1T patent/ES2540089T3/es active Active
- 2007-02-21 CN CN2007800064548A patent/CN101389633B/zh not_active Expired - Fee Related
-
2008
- 2008-06-19 ZA ZA200805331A patent/ZA200805331B/xx unknown
- 2008-07-21 IL IL192928A patent/IL192928A0/en unknown
- 2008-08-15 NO NO20083558A patent/NO20083558L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO20083558L (no) | 2008-09-10 |
| ES2540089T3 (es) | 2015-07-08 |
| WO2007096150A2 (en) | 2007-08-30 |
| CN101389633B (zh) | 2011-08-24 |
| CA2640488A1 (en) | 2007-08-30 |
| CN101389633A (zh) | 2009-03-18 |
| EP1989209B1 (en) | 2015-03-25 |
| US20090131408A1 (en) | 2009-05-21 |
| BRPI0708251A2 (pt) | 2011-05-24 |
| US8258128B2 (en) | 2012-09-04 |
| AU2007218166B9 (en) | 2011-02-10 |
| RU2008137533A (ru) | 2010-03-27 |
| IL192928A0 (en) | 2009-02-11 |
| RU2430921C2 (ru) | 2011-10-10 |
| CA2640488C (en) | 2016-04-26 |
| MX2008010834A (es) | 2008-11-14 |
| AR059597A1 (es) | 2008-04-16 |
| AU2007218166A1 (en) | 2007-08-30 |
| JP5135233B2 (ja) | 2013-02-06 |
| NZ569551A (en) | 2011-06-30 |
| AU2007218166B2 (en) | 2010-11-18 |
| TW200808810A (en) | 2008-02-16 |
| JP2009527518A (ja) | 2009-07-30 |
| ZA200805331B (en) | 2009-10-28 |
| WO2007096150A3 (en) | 2007-10-25 |
| EP1989209A2 (en) | 2008-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20080822 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |