JPH0137374B2 - - Google Patents
Info
- Publication number
- JPH0137374B2 JPH0137374B2 JP30437287A JP30437287A JPH0137374B2 JP H0137374 B2 JPH0137374 B2 JP H0137374B2 JP 30437287 A JP30437287 A JP 30437287A JP 30437287 A JP30437287 A JP 30437287A JP H0137374 B2 JPH0137374 B2 JP H0137374B2
- Authority
- JP
- Japan
- Prior art keywords
- salicylic acid
- compound
- rats
- formula
- reference example
- 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.)
- Expired
Links
- 239000010949 copper Substances 0.000 claims description 43
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 38
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 20
- 229960004889 salicylic acid Drugs 0.000 claims description 20
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 18
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 229910052802 copper Inorganic materials 0.000 claims description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 9
- 230000007935 neutral effect Effects 0.000 claims description 5
- 230000000699 topical effect Effects 0.000 claims description 5
- 239000000499 gel Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000008365 aqueous carrier Substances 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 239000006071 cream Substances 0.000 claims description 2
- 239000006210 lotion Substances 0.000 claims description 2
- 239000002674 ointment Substances 0.000 claims description 2
- 239000006072 paste Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 32
- 241000700159 Rattus Species 0.000 description 29
- 238000000034 method Methods 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 12
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 210000002700 urine Anatomy 0.000 description 7
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 208000027866 inflammatory disease Diseases 0.000 description 6
- 206010061218 Inflammation Diseases 0.000 description 5
- 230000004054 inflammatory process Effects 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 102100038736 Histone H3.3C Human genes 0.000 description 3
- 101001031505 Homo sapiens Histone H3.3C Proteins 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229940033631 carrageenan sodium Drugs 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229960005219 gentisic acid Drugs 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 2
- GYCKQBWUSACYIF-UHFFFAOYSA-N Ethyl salicylate Chemical compound CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 2
- -1 butaryl Chemical compound 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000001879 copper Chemical class 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- CMRVDFLZXRTMTH-UHFFFAOYSA-L copper;2-carboxyphenolate Chemical compound [Cu+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O CMRVDFLZXRTMTH-UHFFFAOYSA-L 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 229940005667 ethyl salicylate Drugs 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- ONJSZLXSECQROL-UHFFFAOYSA-N salicyluric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1O ONJSZLXSECQROL-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OOMWDVDTDKNMCP-UHFFFAOYSA-N 2-[(2-chloropyrimidin-4-yl)amino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=NC(Cl)=N1 OOMWDVDTDKNMCP-UHFFFAOYSA-N 0.000 description 1
- JRXBMCCODQDYEB-UHFFFAOYSA-N 2-[[2-(2-carboxyanilino)pyrimidin-4-yl]amino]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=NC(NC=2C(=CC=CC=2)C(O)=O)=N1 JRXBMCCODQDYEB-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- PGVGABNEHRDPOH-UHFFFAOYSA-N 3-[[2-(2-carboxyanilino)pyrimidin-4-yl]amino]phthalic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=NC=CC(NC=2C(=C(C(O)=O)C=CC=2)C(O)=O)=N1 PGVGABNEHRDPOH-UHFFFAOYSA-N 0.000 description 1
- WYJMUCMGRPIHBX-UHFFFAOYSA-N 4-[[2-(2-carboxyanilino)pyrimidin-4-yl]amino]benzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(C(=O)O)=CC=C1NC1=CC=NC(NC=2C(=CC=CC=2)C(O)=O)=N1 WYJMUCMGRPIHBX-UHFFFAOYSA-N 0.000 description 1
- 239000005750 Copper hydroxide Substances 0.000 description 1
- 102100039875 Histone H3-7 Human genes 0.000 description 1
- 101001035307 Homo sapiens Histone H3-7 Proteins 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- AVGKWJXJXQLDSC-UHFFFAOYSA-N copper;2-hydroxybenzoic acid Chemical compound [Cu].OC(=O)C1=CC=CC=C1O AVGKWJXJXQLDSC-UHFFFAOYSA-N 0.000 description 1
- 229940075144 cylate Drugs 0.000 description 1
- AAERDHZMCAAHJJ-UHFFFAOYSA-N decanoic acid 2-hydroxybenzoic acid Chemical compound C(CCCCCCCCC)(=O)O.C(C=1C(O)=CC=CC1)(=O)O AAERDHZMCAAHJJ-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000004685 tetrahydrates Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPD258477 | 1977-11-28 | ||
| AU2584 | 1977-11-28 | ||
| AU5533 | 1978-08-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63159316A JPS63159316A (ja) | 1988-07-02 |
| JPH0137374B2 true JPH0137374B2 (enrdf_load_stackoverflow) | 1989-08-07 |
Family
ID=3767285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30437287A Granted JPS63159316A (ja) | 1977-11-28 | 1987-12-01 | 中性銅結合体を含む抗炎症組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63159316A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JO3429B1 (ar) * | 2001-08-13 | 2019-10-20 | Janssen Pharmaceutica Nv | مشتقات برميدينات مثبطة فيروس الايدز |
-
1987
- 1987-12-01 JP JP30437287A patent/JPS63159316A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63159316A (ja) | 1988-07-02 |
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