JPH0137374B2 - - Google Patents

Info

Publication number: JPH0137374B2
Authority: JP; Japan
Prior art keywords: salicylic acid; compound; rats; formula; reference example
Prior art date: 1977-11-28
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

Application number

JP30437287A

Other languages

English (en)

Japanese (ja)

Other versions

JPS63159316A (ja

Inventor

Boetsuchaa Barii

Reimondo Uookaa Uiriamu

Ueruzurei Howaitohausu Maikuru

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

ARUKYUSARU Inc Pty Ltd

Original Assignee

ARUKYUSARU Inc Pty Ltd

Priority date (The priority date 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 date listed.)

1977-11-28

Filing date

1987-12-01

Publication date

1989-08-07

1987-12-01 Application filed by ARUKYUSARU Inc Pty Ltd filed Critical ARUKYUSARU Inc Pty Ltd

1988-07-02 Publication of JPS63159316A publication Critical patent/JPS63159316A/ja

1989-08-07 Publication of JPH0137374B2 publication Critical patent/JPH0137374B2/ja

Status Granted legal-status Critical Current

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)

JP30437287A 1977-11-28 1987-12-01 中性銅結合体を含む抗炎症組成物 Granted JPS63159316A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
AUPD258477		1977-11-28
AU5533		1978-08-16
AU2584		1990-10-02

Publications (2)

Publication Number	Publication Date
JPS63159316A JPS63159316A (ja)	1988-07-02
JPH0137374B2 true JPH0137374B2 (fr)	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 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
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

Publication	Publication Date	Title
JPS6331473B2 (fr)	1988-06-23
US4933330A (en)	1990-06-12	Benzoic acid derivatives and use thereof
US4287190A (en)	1981-09-01	Complexes of bivalent copper
JP3831431B2 (ja)	2006-10-11	Ｌ−カルニチン塩および化粧用および皮膚病処置用医薬組成物
JPH02295987A (ja)	1990-12-06	アゼラスチンの塩、その製法、これを含有する喘息予防、抗アレルギー、抗ヒスタミン、消炎及び細胞保護作用を有する薬剤及びその製法
JPH0827081A (ja)	1996-01-30	Ｌ−カルニチン塩および化粧用および皮膚病処置用医薬組成物
EP2768797A1 (fr)	2014-08-27	Nouvelles curcumines modifiées et leurs utilisations
EP0473655B1 (fr)	1997-01-15	Sels metalliques divalents d'indomethacine
JPH059424B2 (fr)	1993-02-04
EP0399051A1 (fr)	1990-11-28	Agent anti-inflammatoire polyvalent
JPS6341474A (ja)	1988-02-22	抗炎症剤
CA1173852A (fr)	1984-09-04	Acides 2-amino-3-(halobenzoyl)-methylpheylacetiques; leurs esters et leurs sels
JPH04217676A (ja)	1992-08-07	カルボン酸誘導体
HU226686B1 (en)	2009-06-29	Semisolid pharmaceutical formulation containing dexketoprofen trometamol
HU194877B (en)	1988-03-28	Process for producing morpholinoethyl-ester-diniflumate of nifluminic acid and pharmaceutical composition containing them
EP0492747B1 (fr)	1996-03-20	Préparation pharmaceutique pour application topique
JP2003512425A (ja)	2003-04-02	６−メトキシ−２−ナフチル酢酸プロドラッグ
JPS63159316A (ja)	1988-07-02	中性銅結合体を含む抗炎症組成物
US4539206A (en)	1985-09-03	Topical compositions containing copper (II) complexes of 3,5-dioxo-pyrazolidine derivatives and methods of combatting inflammation with them
EP0498011B1 (fr)	1995-04-26	Sels de l'acide 2-(2,6-dichloroanilino)-phénylacétique procédé pour leur préparation et leur application comme préparation pharmaceutique pour utilisation topique
CY1324A (en)	1986-06-27	Antibacterial compositions containing chlorhexidine
DE2706841A1 (de)	1977-09-01	Arzneipraeparat fuer die orale verabreichung und verfahren zur herstellung des wirkstoffs
US4440786A (en)	1984-04-03	Compounds with antiinflammatory and analgesic activity, process for the preparation thereof and pharmaceutical compositio ns therefrom
JPH02196791A (ja)	1990-08-03	システイン酸亜鉛、その製造方法並びに医薬及び化粧品への用途
JPS58183653A (ja)	1983-10-26	２―アミノ―６―ビフェニル酢酸とそれからなる筋弛緩剤