CS246051B2 - Cis-platinum-diaminodichloride's stable concentrated solution production method - Google Patents
Cis-platinum-diaminodichloride's stable concentrated solution production method Download PDFInfo
- Publication number
- CS246051B2 CS246051B2 CS812390A CS239081A CS246051B2 CS 246051 B2 CS246051 B2 CS 246051B2 CS 812390 A CS812390 A CS 812390A CS 239081 A CS239081 A CS 239081A CS 246051 B2 CS246051 B2 CS 246051B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- solution
- cisplatin
- platinum
- polyethylene glycol
- cis
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 49
- 239000000203 mixture Substances 0.000 claims abstract description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 16
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 13
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 231100000252 nontoxic Toxicity 0.000 claims abstract description 6
- 230000003000 nontoxic effect Effects 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 229960004316 cisplatin Drugs 0.000 abstract description 55
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 abstract description 52
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 138
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 57
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 57
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 56
- 229910052697 platinum Inorganic materials 0.000 description 30
- 239000011780 sodium chloride Substances 0.000 description 30
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 26
- BSJGASKRWFKGMV-UHFFFAOYSA-L ammonia dichloroplatinum(2+) Chemical compound N.N.Cl[Pt+2]Cl BSJGASKRWFKGMV-UHFFFAOYSA-L 0.000 description 24
- 238000004809 thin layer chromatography Methods 0.000 description 24
- 239000008213 purified water Substances 0.000 description 23
- 239000004480 active ingredient Substances 0.000 description 13
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 12
- 229930195725 Mannitol Natural products 0.000 description 12
- 239000000594 mannitol Substances 0.000 description 12
- 235000010355 mannitol Nutrition 0.000 description 12
- 239000013543 active substance Substances 0.000 description 10
- 229910052782 aluminium Inorganic materials 0.000 description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 206010028980 Neoplasm Diseases 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 7
- 239000004809 Teflon Substances 0.000 description 7
- 229920006362 Teflon® Polymers 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000011888 foil Substances 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 239000001110 calcium chloride Substances 0.000 description 6
- 229910001628 calcium chloride Inorganic materials 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000008227 sterile water for injection Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- -1 cis-platinum (II) diamine Chemical class 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000008223 sterile water Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229940000406 drug candidate Drugs 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910001504 inorganic chloride Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002547 new drug Substances 0.000 description 2
- 229940057847 polyethylene glycol 600 Drugs 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- XKRXLNHFIINMAM-UHFFFAOYSA-N [Pt+5] Chemical compound [Pt+5] XKRXLNHFIINMAM-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- SVRSEHNKNVARQT-UHFFFAOYSA-N azane;cobalt;thiocyanic acid Chemical compound [NH4+].[Co].[S-]C#N SVRSEHNKNVARQT-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- OTEYRJLGZKIQQD-UHFFFAOYSA-N bis(2,2,3,3,4,4,5,5-octafluoropentyl) benzene-1,2-dicarboxylate Chemical compound FC(F)C(F)(F)C(F)(F)C(F)(F)COC(=O)C1=CC=CC=C1C(=O)OCC(F)(F)C(F)(F)C(F)(F)C(F)F OTEYRJLGZKIQQD-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000012470 diluted sample Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 239000008215 water for injection Substances 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
-
- 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
- A61K33/243—Platinum; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13537380A | 1980-03-31 | 1980-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS246051B2 true CS246051B2 (en) | 1986-10-16 |
Family
ID=22467813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS812390A CS246051B2 (en) | 1980-03-31 | 1981-03-31 | Cis-platinum-diaminodichloride's stable concentrated solution production method |
Country Status (30)
| Country | Link |
|---|---|
| JP (1) | JPS56152415A (en)) |
| KR (1) | KR860000841B1 (en)) |
| AR (1) | AR225500A1 (en)) |
| AT (1) | AT370996B (en)) |
| AU (1) | AU541056B2 (en)) |
| BE (1) | BE888209A (en)) |
| CA (1) | CA1162479A (en)) |
| CH (1) | CH647481A5 (en)) |
| CS (1) | CS246051B2 (en)) |
| DD (1) | DD157762A5 (en)) |
| DE (1) | DE3112272A1 (en)) |
| DK (1) | DK158564C (en)) |
| ES (1) | ES8206545A1 (en)) |
| FI (1) | FI70670C (en)) |
| FR (1) | FR2480605A1 (en)) |
| GB (1) | GB2074028B (en)) |
| GR (1) | GR72769B (en)) |
| HU (1) | HU183379B (en)) |
| IE (1) | IE51070B1 (en)) |
| IL (1) | IL62517A (en)) |
| IT (1) | IT1170838B (en)) |
| LU (1) | LU83270A1 (en)) |
| NL (1) | NL8101531A (en)) |
| NO (1) | NO156675C (en)) |
| NZ (1) | NZ196519A (en)) |
| PH (1) | PH17152A (en)) |
| PT (1) | PT72774B (en)) |
| SE (1) | SE455045B (en)) |
| SU (1) | SU1056893A3 (en)) |
| ZA (1) | ZA812084B (en)) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1153974B (it) * | 1982-09-23 | 1987-01-21 | Erba Farmitalia | Composizioni farmacologiche a base di cisplatino e metodo per il loro ottenimento |
| NL8303657A (nl) * | 1983-10-24 | 1985-05-17 | Pharmachemie Bv | Voor injectie geschikte, stabiele, waterige, zoutzuur bevattende oplossing van cisplatine, alsmede werkwijze ter bereiding daarvan. |
| FI895340A7 (fi) * | 1988-11-14 | 1990-05-15 | Bristol Myers Squibb Co | Hypertoninen cisplatin-liuos |
| AU714992B2 (en) * | 1996-08-23 | 2000-01-13 | Alza Corporation | Liposomes containing a cisplatin compound |
| AUPQ641100A0 (en) | 2000-03-23 | 2000-04-15 | Australia Nuclear Science & Technology Organisation | Methods of synthesis and use of radiolabelled platinum chemotherapeutic ag ents |
| JP4445304B2 (ja) | 2004-03-26 | 2010-04-07 | オンキヨー株式会社 | スイッチングアンプ |
| US8852566B2 (en) * | 2009-03-26 | 2014-10-07 | Warsaw Orthopedic, Inc. | Compositions and methods for preferential distribution of active agents to injury sites |
| KR102832060B1 (ko) | 2018-03-29 | 2025-07-10 | 프로젝트 파마슈틱스 게엠베하 | 액체 약학적 제형 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4177263A (en) * | 1972-02-28 | 1979-12-04 | Research Corporation | Anti-animal tumor method |
| SE445172B (sv) * | 1978-05-30 | 1986-06-09 | Bristol Myers Co | Stabil, steril vattenlosning av cisplatin i enhetsdoseringsform |
-
1981
- 1981-03-06 CA CA000372499A patent/CA1162479A/en not_active Expired
- 1981-03-06 AU AU68166/81A patent/AU541056B2/en not_active Ceased
- 1981-03-17 NZ NZ196519A patent/NZ196519A/xx unknown
- 1981-03-24 IT IT48090/81A patent/IT1170838B/it active
- 1981-03-24 FR FR8105848A patent/FR2480605A1/fr active Granted
- 1981-03-25 CH CH2023/81A patent/CH647481A5/fr not_active IP Right Cessation
- 1981-03-26 GR GR64497A patent/GR72769B/el unknown
- 1981-03-26 FI FI810934A patent/FI70670C/fi not_active IP Right Cessation
- 1981-03-27 DE DE19813112272 patent/DE3112272A1/de active Granted
- 1981-03-27 PH PH25435A patent/PH17152A/en unknown
- 1981-03-27 ZA ZA00812084A patent/ZA812084B/xx unknown
- 1981-03-27 SE SE8101990A patent/SE455045B/sv not_active IP Right Cessation
- 1981-03-27 NL NL8101531A patent/NL8101531A/nl not_active Application Discontinuation
- 1981-03-28 KR KR1019810001029A patent/KR860000841B1/ko not_active Expired
- 1981-03-30 IL IL62517A patent/IL62517A/xx unknown
- 1981-03-30 JP JP4569081A patent/JPS56152415A/ja active Granted
- 1981-03-30 HU HU81811A patent/HU183379B/hu not_active IP Right Cessation
- 1981-03-30 IE IE715/81A patent/IE51070B1/en not_active IP Right Cessation
- 1981-03-30 PT PT72774A patent/PT72774B/pt not_active IP Right Cessation
- 1981-03-30 DK DK144281A patent/DK158564C/da not_active IP Right Cessation
- 1981-03-30 SU SU813265697A patent/SU1056893A3/ru active
- 1981-03-30 ES ES500869A patent/ES8206545A1/es not_active Expired
- 1981-03-30 NO NO811081A patent/NO156675C/no unknown
- 1981-03-30 GB GB8109926A patent/GB2074028B/en not_active Expired
- 1981-03-30 AR AR284799A patent/AR225500A1/es active
- 1981-03-31 AT AT0150481A patent/AT370996B/de not_active IP Right Cessation
- 1981-03-31 CS CS812390A patent/CS246051B2/cs unknown
- 1981-03-31 LU LU83270A patent/LU83270A1/fr unknown
- 1981-03-31 BE BE0/204323A patent/BE888209A/fr not_active IP Right Cessation
- 1981-03-31 DD DD81228776A patent/DD157762A5/de not_active IP Right Cessation
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