DE2734808C2 - Arzneimittel zur Behandlung von Polyarthritis - Google Patents
Arzneimittel zur Behandlung von PolyarthritisInfo
- Publication number
- DE2734808C2 DE2734808C2 DE2734808A DE2734808A DE2734808C2 DE 2734808 C2 DE2734808 C2 DE 2734808C2 DE 2734808 A DE2734808 A DE 2734808A DE 2734808 A DE2734808 A DE 2734808A DE 2734808 C2 DE2734808 C2 DE 2734808C2
- Authority
- DE
- Germany
- Prior art keywords
- gold
- chloride
- bis
- solution
- triethylphosphine
- 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
- 239000003814 drug Substances 0.000 title claims description 17
- 206010036030 Polyarthritis Diseases 0.000 title claims description 6
- 206010003246 arthritis Diseases 0.000 title claims description 6
- 208000030428 polyarticular arthritis Diseases 0.000 title claims description 6
- 229940079593 drug Drugs 0.000 title description 11
- -1 tetrafluoroborate ion Chemical group 0.000 claims description 14
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 5
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical group OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 208000009386 Experimental Arthritis Diseases 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 210000002966 serum Anatomy 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 239000010931 gold Substances 0.000 description 4
- CLEUDPVZNLAYBR-UHFFFAOYSA-K gold(3+);triethylphosphane;trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Au+3].CCP(CC)CC.CCP(CC)CC CLEUDPVZNLAYBR-UHFFFAOYSA-K 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- SYBBXLKWGHAVHP-UHFFFAOYSA-M chlorogold;triethylphosphane Chemical compound [Cl-].[Au+].CCP(CC)CC SYBBXLKWGHAVHP-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 150000002344 gold compounds Chemical class 0.000 description 3
- 210000000548 hind-foot Anatomy 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 description 3
- 229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- KIUMMUBSPKGMOY-UHFFFAOYSA-N 3,3'-Dithiobis(6-nitrobenzoic acid) Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(SSC=2C=C(C(=CC=2)[N+]([O-])=O)C(O)=O)=C1 KIUMMUBSPKGMOY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 229910003771 Gold(I) chloride Inorganic materials 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000004791 biological behavior Effects 0.000 description 2
- DCVQRCZEVHAMBN-UHFFFAOYSA-M chlorogold;diethyl(phenyl)phosphane Chemical compound [Au]Cl.CCP(CC)C1=CC=CC=C1 DCVQRCZEVHAMBN-UHFFFAOYSA-M 0.000 description 2
- LVTCZSBUROAWTE-UHFFFAOYSA-N diethyl(phenyl)phosphane Chemical compound CCP(CC)C1=CC=CC=C1 LVTCZSBUROAWTE-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 210000002683 foot Anatomy 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 229940015045 gold sodium thiomalate Drugs 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229940126601 medicinal product Drugs 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- AGHLUVOCTHWMJV-UHFFFAOYSA-J sodium;gold(3+);2-sulfanylbutanedioate Chemical compound [Na+].[Au+3].[O-]C(=O)CC(S)C([O-])=O.[O-]C(=O)CC(S)C([O-])=O AGHLUVOCTHWMJV-UHFFFAOYSA-J 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 229960004793 sucrose Drugs 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 2
- YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 2
- 230000004584 weight gain Effects 0.000 description 2
- 235000019786 weight gain Nutrition 0.000 description 2
- RBWNDBNSJFCLBZ-UHFFFAOYSA-N 7-methyl-5,6,7,8-tetrahydro-3h-[1]benzothiolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CNC(=S)C2=C1SC1=C2CCC(C)C1 RBWNDBNSJFCLBZ-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 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 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 102000018721 Macroglobulins Human genes 0.000 description 1
- 108010091934 Macroglobulins Proteins 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 230000002917 arthritic effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- CADCHRBXMXCBFL-UHFFFAOYSA-M chlorogold trimethyl phosphite Chemical compound [Au]Cl.COP(OC)OC CADCHRBXMXCBFL-UHFFFAOYSA-M 0.000 description 1
- OORRRESLKIYRIS-UHFFFAOYSA-M chlorogold;trimethylphosphane Chemical compound [Au]Cl.CP(C)C.CP(C)C OORRRESLKIYRIS-UHFFFAOYSA-M 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 208000018631 connective tissue disease Diseases 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 150000002343 gold Chemical class 0.000 description 1
- FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 description 1
- ZBKIUFWVEIBQRT-UHFFFAOYSA-N gold(1+) Chemical class [Au+] ZBKIUFWVEIBQRT-UHFFFAOYSA-N 0.000 description 1
- PMCMJPXEJUKOAO-UHFFFAOYSA-M gold(1+);bromide Chemical compound [Au]Br PMCMJPXEJUKOAO-UHFFFAOYSA-M 0.000 description 1
- BVRRHCPRDPAYFI-UHFFFAOYSA-M gold(1+);trimethylphosphane;chloride Chemical compound [Au]Cl.CP(C)C BVRRHCPRDPAYFI-UHFFFAOYSA-M 0.000 description 1
- IFPWCRBNZXUWGC-UHFFFAOYSA-M gold(1+);triphenylphosphane;chloride Chemical compound [Cl-].[Au+].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 IFPWCRBNZXUWGC-UHFFFAOYSA-M 0.000 description 1
- 230000035931 haemagglutination Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000012907 medicinal substance Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910001494 silver tetrafluoroborate Inorganic materials 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 229940098466 sublingual tablet Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- XYYVDQWGDNRQDA-UHFFFAOYSA-K trichlorogold;trihydrate;hydrochloride Chemical compound O.O.O.Cl.Cl[Au](Cl)Cl XYYVDQWGDNRQDA-UHFFFAOYSA-K 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
-
- 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
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/710,506 US4057630A (en) | 1976-08-02 | 1976-08-02 | Antiarthritic compositions comprising bis-coordinated gold(1+) salts and methods of producing antiarthritic activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2734808A1 DE2734808A1 (de) | 1978-02-09 |
| DE2734808C2 true DE2734808C2 (de) | 1987-01-15 |
Family
ID=24854326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2734808A Expired DE2734808C2 (de) | 1976-08-02 | 1977-08-02 | Arzneimittel zur Behandlung von Polyarthritis |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4057630A (show.php) |
| JP (1) | JPS5318737A (show.php) |
| AU (1) | AU510060B2 (show.php) |
| BE (1) | BE857354A (show.php) |
| DE (1) | DE2734808C2 (show.php) |
| FR (1) | FR2360312A1 (show.php) |
| GB (1) | GB1589588A (show.php) |
| IE (1) | IE45326B1 (show.php) |
| IL (1) | IL52612A (show.php) |
| NL (1) | NL7708478A (show.php) |
| ZA (1) | ZA774629B (show.php) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4764509A (en) * | 1986-02-21 | 1988-08-16 | Smithkline Beckman Corporation | Pharmaceutical compositions containing di-gold phosphine |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3676554A (en) * | 1970-10-30 | 1972-07-11 | Smith Kline French Lab | Anti-arthritic compositions comprising phosphine or phosphite gold halide complexes and methods of producing anti-arthritic activity |
| US3718680A (en) * | 1971-06-07 | 1973-02-27 | Smith Kline French Lab | Phosphine or phosphite gold complexes of thioethanol and derivatives thereof |
| US3887707A (en) * | 1973-07-23 | 1975-06-03 | Smithkline Corp | Anti-arthritic compositions comprising an S-phosphine or phosphite gold thio-cyanate and methods of producing anti-arthritic activity |
-
1976
- 1976-08-02 US US05/710,506 patent/US4057630A/en not_active Expired - Lifetime
-
1977
- 1977-07-22 GB GB30793/77A patent/GB1589588A/en not_active Expired
- 1977-07-26 FR FR7722908A patent/FR2360312A1/fr active Granted
- 1977-07-27 JP JP9089477A patent/JPS5318737A/ja active Pending
- 1977-07-27 IL IL52612A patent/IL52612A/xx unknown
- 1977-07-29 IE IE1593/77A patent/IE45326B1/en unknown
- 1977-07-29 AU AU27472/77A patent/AU510060B2/en not_active Expired
- 1977-08-01 BE BE179802A patent/BE857354A/xx not_active IP Right Cessation
- 1977-08-01 ZA ZA00774629A patent/ZA774629B/xx unknown
- 1977-08-01 NL NL7708478A patent/NL7708478A/xx not_active Application Discontinuation
- 1977-08-02 DE DE2734808A patent/DE2734808C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ZA774629B (en) | 1978-06-28 |
| GB1589588A (en) | 1981-05-13 |
| FR2360312B1 (show.php) | 1981-06-19 |
| AU510060B2 (en) | 1980-06-05 |
| FR2360312A1 (fr) | 1978-03-03 |
| IE45326L (en) | 1978-02-02 |
| JPS5318737A (en) | 1978-02-21 |
| BE857354A (fr) | 1978-02-01 |
| NL7708478A (nl) | 1978-02-06 |
| DE2734808A1 (de) | 1978-02-09 |
| IE45326B1 (en) | 1982-07-28 |
| IL52612A (en) | 1980-09-16 |
| AU2747277A (en) | 1979-02-01 |
| IL52612A0 (en) | 1977-10-31 |
| US4057630A (en) | 1977-11-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2607620A1 (de) | Olefinische derivate von aminosaeuren, sowie verfahren zu deren herstellung | |
| CH638513A5 (de) | Verfahren zur herstellung neuer 4-amino-4-arylcyclohexanonketale. | |
| DE3709621A1 (de) | Therapeutisches mittel | |
| CH635818A5 (de) | 4-aminocyclohexanole, deren acylate und saeureadditionssalze und diese enthaltende arzneimittel. | |
| DD235450B1 (de) | Verfahren zur herstellung neuer 1-(2-hydroxyaryl)-alkan-1-on-oxime | |
| DE2607592A1 (de) | Acetylenderivate von aminosaeuren sowie verfahren zu deren herstellung | |
| EP0192056B1 (de) | Verfahren zur Herstellung von Labdan-Derivaten und ihre Verwendung als Arzneimittel | |
| DE2549783B2 (de) | Triglyceride mit entzündungshemmender Wirkung | |
| US5202313A (en) | Bilobalide derivatives, their applications and formulations containing them | |
| EP0004680A2 (de) | Nonatetraensäure-Derivat und pharmazeutische Kompositionen | |
| DE68915269T2 (de) | Polyvalentes entzündungshemmendes mittel. | |
| CH615409A5 (show.php) | ||
| DE2434919C2 (de) | Phosphin- und Phosphit-Goldkomplexe von Thiobenzoesäure und substituierten Thiophenolen und ihre Verwendung | |
| DE2734808C2 (de) | Arzneimittel zur Behandlung von Polyarthritis | |
| DE3730277C2 (de) | Salz einer Organogermaniumverbindung und dessen Verwendung | |
| DE69023045T2 (de) | Carboxamidderivate. | |
| DE2437146C2 (de) | Phosphin-Gold-Chelate und ihre Verwendung | |
| DE2756866C2 (de) | N-Oleoyl-Derivate von Phosphatidyläthanolaminen, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2748291B2 (de) | Substituierte 13-Benzodioxan-4one und Verfahren zu ihrer Herstellung sowie Verwendung dieser Verbindungen bei der Bekämpfung von Entzündungen | |
| DE69509091T2 (de) | Salze von 2-[(2,6-dichlorophenyl)amin]phenylacetoxyessigsäure mit organischen basischen kationen | |
| DE2437147C2 (de) | Phosphin- und Phosphit-Goldkomplexe und ihre Verwendung | |
| US3870792A (en) | Certain dihydrophthalizines for treating hemorrhage and thrombosis | |
| EP0313935A2 (de) | Enolether von 6-Chlor-4-hydroxy-2-methyl-N-(2-pyridyl)-2H-thieno(2,3-e)-1,2-thiazin-3-carbonsäureamid-1,1-dioxid, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung | |
| DE69018741T2 (de) | Konjugierte gamma-Hydroxybutenolid-Derivate und sie als aktiver Wirkstoff enthaltende Mittel gegen Magengeschwüre. | |
| DE2061181C3 (de) | Antiarthritisch wirkendes Arzneimittel auf der Basis einer Goldverbindung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |