DE2949733A1 - Silbersalze der phosphanilsaeure, verfahren zu deren herstellung und arzneimittel - Google Patents
Silbersalze der phosphanilsaeure, verfahren zu deren herstellung und arzneimittelInfo
- Publication number
- DE2949733A1 DE2949733A1 DE19792949733 DE2949733A DE2949733A1 DE 2949733 A1 DE2949733 A1 DE 2949733A1 DE 19792949733 DE19792949733 DE 19792949733 DE 2949733 A DE2949733 A DE 2949733A DE 2949733 A1 DE2949733 A1 DE 2949733A1
- Authority
- DE
- Germany
- Prior art keywords
- mixed
- mixture
- organic solvent
- precipitate
- phosphanilic acid
- 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- Withdrawn
Links
- OAOBMEMWHJWPNA-UHFFFAOYSA-N (4-aminophenyl)phosphonic acid Chemical class NC1=CC=C(P(O)(O)=O)C=C1 OAOBMEMWHJWPNA-UHFFFAOYSA-N 0.000 title claims description 28
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical class [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 229940126601 medicinal product Drugs 0.000 title 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 12
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 12
- 239000006071 cream Substances 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 9
- 239000000908 ammonium hydroxide Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 230000000844 anti-bacterial effect Effects 0.000 claims description 8
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000003378 silver Chemical class 0.000 claims description 5
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000007900 aqueous suspension Substances 0.000 claims description 4
- 239000002244 precipitate Substances 0.000 claims description 4
- 230000001580 bacterial effect Effects 0.000 claims description 2
- 230000000774 hypoallergenic effect Effects 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims 1
- 239000003860 topical agent Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 7
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 7
- 229960003600 silver sulfadiazine Drugs 0.000 description 6
- 241000588653 Neisseria Species 0.000 description 5
- 230000003115 biocidal effect Effects 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 3
- 241000193996 Streptococcus pyogenes Species 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 2
- 241000588921 Enterobacteriaceae Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000186359 Mycobacterium Species 0.000 description 2
- 229930193140 Neomycin Natural products 0.000 description 2
- 241000588769 Proteus <enterobacteria> Species 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- 241000607142 Salmonella Species 0.000 description 2
- 241000607768 Shigella Species 0.000 description 2
- 241001312524 Streptococcus viridans Species 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000002054 inoculum Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 229960004927 neomycin Drugs 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229940104230 thymidine Drugs 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000588807 Bordetella Species 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- 150000000703 Cerium Chemical class 0.000 description 1
- 241000186245 Corynebacterium xerosis Species 0.000 description 1
- 206010011509 Crystalluria Diseases 0.000 description 1
- 241000040660 Echinopsis mirabilis Species 0.000 description 1
- 241000588697 Enterobacter cloacae Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000606790 Haemophilus Species 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- 241000228404 Histoplasma capsulatum Species 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
- 241000186781 Listeria Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000588772 Morganella morganii Species 0.000 description 1
- 241000606860 Pasteurella Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000224016 Plasmodium Species 0.000 description 1
- 229920002701 Polyoxyl 40 Stearate Polymers 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 241000588777 Providencia rettgeri Species 0.000 description 1
- 101710132082 Pyrimidine/purine nucleoside phosphorylase Proteins 0.000 description 1
- 206010062237 Renal impairment Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000607715 Serratia marcescens Species 0.000 description 1
- 206010040943 Skin Ulcer Diseases 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 102000013537 Thymidine Phosphorylase Human genes 0.000 description 1
- 241001467018 Typhis Species 0.000 description 1
- 241000607598 Vibrio Species 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- WERKSKAQRVDLDW-ANOHMWSOSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentahydroxyhexyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO WERKSKAQRVDLDW-ANOHMWSOSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000000244 anti-pseudomonal effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- -1 aromatic phosphonic acids Chemical class 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000005977 kidney dysfunction Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 229940099429 polyoxyl 40 stearate Drugs 0.000 description 1
- QMYDVDBERNLWKB-UHFFFAOYSA-N propane-1,2-diol;hydrate Chemical compound O.CC(O)CO QMYDVDBERNLWKB-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 230000003362 replicative effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229940099261 silvadene Drugs 0.000 description 1
- FTHXNDRIJXQDTA-UHFFFAOYSA-N silver tetramer Chemical compound [Ag].[Ag].[Ag].[Ag] FTHXNDRIJXQDTA-UHFFFAOYSA-N 0.000 description 1
- BSWGGJHLVUUXTL-UHFFFAOYSA-N silver zinc Chemical compound [Zn].[Ag] BSWGGJHLVUUXTL-UHFFFAOYSA-N 0.000 description 1
- 231100000019 skin ulcer Toxicity 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229940072172 tetracycline antibiotic Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 230000001549 tubercolostatic effect Effects 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/38—Silver; Compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3834—Aromatic acids (P-C aromatic linkage)
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/968,315 US4177199A (en) | 1978-12-11 | 1978-12-11 | Silver salts of phosphanilic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2949733A1 true DE2949733A1 (de) | 1980-06-19 |
Family
ID=25514056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792949733 Withdrawn DE2949733A1 (de) | 1978-12-11 | 1979-12-11 | Silbersalze der phosphanilsaeure, verfahren zu deren herstellung und arzneimittel |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4177199A (enExample) |
| JP (1) | JPS5585596A (enExample) |
| KR (1) | KR830001662B1 (enExample) |
| AU (1) | AU524960B2 (enExample) |
| CA (1) | CA1192573A (enExample) |
| CH (1) | CH645649A5 (enExample) |
| DE (1) | DE2949733A1 (enExample) |
| DK (1) | DK522979A (enExample) |
| FI (1) | FI67856C (enExample) |
| FR (1) | FR2444045A1 (enExample) |
| GB (1) | GB2036748B (enExample) |
| GR (1) | GR74050B (enExample) |
| IE (1) | IE49230B1 (enExample) |
| IT (1) | IT1164775B (enExample) |
| LU (1) | LU81968A1 (enExample) |
| NL (1) | NL7908886A (enExample) |
| SE (1) | SE444686B (enExample) |
| YU (1) | YU43461B (enExample) |
| ZA (1) | ZA796640B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE1004467A3 (nl) * | 1990-06-18 | 1992-11-24 | Sollie Philippe | Stikstof- en zilverhoudend derivaat. |
| US6555333B1 (en) * | 2002-05-14 | 2003-04-29 | Pml Microbiologicals, Inc. | Broad spectrum fastidious organism culture medium |
| KR20110031496A (ko) | 2008-07-15 | 2011-03-28 | 바스프 코포레이션 | 비세포독성 이산화염소 유체 |
| WO2010009133A2 (en) * | 2008-07-15 | 2010-01-21 | Basf Catalysts Llc | Tooth polishing compositions and methods of tooth polishing without mechanical abrasion |
| US20100196512A1 (en) | 2009-02-04 | 2010-08-05 | Basf Catalyst Llc | Treatment of Non-Oral Biological Tissue with Chlorine Dioxide |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2328358A (en) * | 1941-01-23 | 1943-08-31 | Du Pont | Organic compound and process for preparing the same |
| US3694447A (en) * | 1970-03-10 | 1972-09-26 | Smith Kline French Lab | Complexes of phosphanilic acid and 9-amino-3-nitroacridine |
| GB1346544A (en) * | 1971-06-01 | 1974-02-13 | Univ Washington | Silver allantoinate-containing compositions |
| US3856805A (en) * | 1971-06-16 | 1974-12-24 | Univ Washington | Silver zinc allantoin complex |
-
1978
- 1978-12-11 US US05/968,315 patent/US4177199A/en not_active Expired - Lifetime
-
1979
- 1979-10-10 YU YU2457/79A patent/YU43461B/xx unknown
- 1979-11-06 CA CA000339237A patent/CA1192573A/en not_active Expired
- 1979-12-06 FR FR7929992A patent/FR2444045A1/fr active Granted
- 1979-12-07 DK DK522979A patent/DK522979A/da not_active Application Discontinuation
- 1979-12-07 ZA ZA00796640A patent/ZA796640B/xx unknown
- 1979-12-08 KR KR1019790004339A patent/KR830001662B1/ko not_active Expired
- 1979-12-10 SE SE7910160A patent/SE444686B/sv unknown
- 1979-12-10 JP JP15931479A patent/JPS5585596A/ja active Granted
- 1979-12-10 AU AU53657/79A patent/AU524960B2/en not_active Ceased
- 1979-12-10 LU LU81968A patent/LU81968A1/fr unknown
- 1979-12-10 FI FI793851A patent/FI67856C/fi not_active IP Right Cessation
- 1979-12-10 CH CH1094579A patent/CH645649A5/fr not_active IP Right Cessation
- 1979-12-10 NL NL7908886A patent/NL7908886A/nl not_active Application Discontinuation
- 1979-12-10 IT IT51033/79A patent/IT1164775B/it active
- 1979-12-10 IE IE2381/79A patent/IE49230B1/en unknown
- 1979-12-10 GB GB7942466A patent/GB2036748B/en not_active Expired
- 1979-12-11 DE DE19792949733 patent/DE2949733A1/de not_active Withdrawn
- 1979-12-11 GR GR60721A patent/GR74050B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE7910160L (sv) | 1980-06-12 |
| IE792381L (en) | 1980-06-11 |
| JPS5585596A (en) | 1980-06-27 |
| IT1164775B (it) | 1987-04-15 |
| IE49230B1 (en) | 1985-09-04 |
| KR830001662B1 (ko) | 1983-08-23 |
| JPS6254313B2 (enExample) | 1987-11-13 |
| SE444686B (sv) | 1986-04-28 |
| FI793851A7 (fi) | 1980-06-12 |
| US4177199A (en) | 1979-12-04 |
| FR2444045B1 (enExample) | 1984-09-14 |
| NL7908886A (nl) | 1980-06-13 |
| YU245779A (en) | 1983-02-28 |
| GB2036748A (en) | 1980-07-02 |
| FR2444045A1 (fr) | 1980-07-11 |
| GR74050B (enExample) | 1984-06-06 |
| AU5365779A (en) | 1980-06-19 |
| ZA796640B (en) | 1981-03-25 |
| CH645649A5 (fr) | 1984-10-15 |
| DK522979A (da) | 1980-06-12 |
| IT7951033A0 (it) | 1979-12-10 |
| AU524960B2 (en) | 1982-10-14 |
| YU43461B (en) | 1989-08-31 |
| GB2036748B (en) | 1983-07-20 |
| KR830000906A (ko) | 1983-04-28 |
| FI67856C (fi) | 1985-06-10 |
| LU81968A1 (fr) | 1980-07-01 |
| CA1192573A (en) | 1985-08-27 |
| FI67856B (fi) | 1985-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |