CA1148086A - .beta.-GLUCURONIDASE ACTIVITY AND/OR PH-DEPENDENT PHARMACEUTICALS AND THEIR METHODS OF PRODUCTION AND USE FOR SELECTIVE TREATMENT OF DISEASES - Google Patents
.beta.-GLUCURONIDASE ACTIVITY AND/OR PH-DEPENDENT PHARMACEUTICALS AND THEIR METHODS OF PRODUCTION AND USE FOR SELECTIVE TREATMENT OF DISEASESInfo
- Publication number
- CA1148086A CA1148086A CA000337483A CA337483A CA1148086A CA 1148086 A CA1148086 A CA 1148086A CA 000337483 A CA000337483 A CA 000337483A CA 337483 A CA337483 A CA 337483A CA 1148086 A CA1148086 A CA 1148086A
- Authority
- CA
- Canada
- Prior art keywords
- glucuronic acid
- tumor
- glucuronide
- acid
- beta
- 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
- 230000000694 effects Effects 0.000 title abstract description 76
- 238000000034 method Methods 0.000 title abstract description 68
- 238000011282 treatment Methods 0.000 title abstract description 30
- 239000003814 drug Substances 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 4
- 201000010099 disease Diseases 0.000 title description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 3
- 229930182480 glucuronide Natural products 0.000 claims abstract description 107
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 76
- 210000004881 tumor cell Anatomy 0.000 claims abstract description 40
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 claims abstract description 39
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 claims abstract description 39
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 claims abstract description 39
- 230000002588 toxic effect Effects 0.000 claims abstract description 27
- 231100000331 toxic Toxicity 0.000 claims abstract description 26
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- 239000002253 acid Substances 0.000 claims abstract description 18
- 150000002825 nitriles Chemical class 0.000 claims abstract description 12
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims abstract description 11
- 235000019345 sodium thiosulphate Nutrition 0.000 claims abstract description 11
- 208000029039 cyanide poisoning Diseases 0.000 claims abstract description 7
- NNICRUQPODTGRU-UHFFFAOYSA-N mandelonitrile Chemical compound N#CC(O)C1=CC=CC=C1 NNICRUQPODTGRU-UHFFFAOYSA-N 0.000 claims description 64
- -1 glucuronide compound Chemical class 0.000 claims description 30
- 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 claims description 12
- 239000008103 glucose Substances 0.000 claims description 11
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 9
- 230000000259 anti-tumor effect Effects 0.000 claims description 7
- 239000000864 hyperglycemic agent Substances 0.000 claims description 5
- 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 claims description 4
- 229930091371 Fructose Natural products 0.000 claims description 4
- 239000005715 Fructose Substances 0.000 claims description 4
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 4
- 102000051325 Glucagon Human genes 0.000 claims description 4
- 108060003199 Glucagon Proteins 0.000 claims description 4
- 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 claims description 4
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 4
- 229930182830 galactose Natural products 0.000 claims description 4
- MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 claims description 4
- 229960004666 glucagon Drugs 0.000 claims description 4
- 239000008101 lactose Substances 0.000 claims description 4
- 239000011736 potassium bicarbonate Substances 0.000 claims description 4
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 4
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 4
- 239000000729 antidote Substances 0.000 claims description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 3
- 239000001508 potassium citrate Substances 0.000 claims 3
- 229960002635 potassium citrate Drugs 0.000 claims 3
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 claims 3
- 235000011082 potassium citrates Nutrition 0.000 claims 3
- 239000001509 sodium citrate Substances 0.000 claims 3
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims 3
- 235000011083 sodium citrates Nutrition 0.000 claims 3
- 150000008134 glucuronides Chemical class 0.000 abstract description 93
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 abstract description 44
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 abstract description 44
- 150000001875 compounds Chemical class 0.000 abstract description 44
- 229940097043 glucuronic acid Drugs 0.000 abstract description 43
- 210000004027 cell Anatomy 0.000 abstract description 30
- 210000002700 urine Anatomy 0.000 abstract description 27
- 230000008569 process Effects 0.000 abstract description 25
- 238000009535 clinical urine test Methods 0.000 abstract description 5
- 238000003745 diagnosis Methods 0.000 abstract description 4
- 230000001580 bacterial effect Effects 0.000 abstract description 3
- 238000011065 in-situ storage Methods 0.000 abstract description 2
- 238000001959 radiotherapy Methods 0.000 abstract description 2
- 230000002779 inactivation Effects 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 38
- 201000011510 cancer Diseases 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 15
- 210000001519 tissue Anatomy 0.000 description 15
- 238000012360 testing method Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 12
- 229910001863 barium hydroxide Inorganic materials 0.000 description 12
- 230000021962 pH elevation Effects 0.000 description 12
- 241000894006 Bacteria Species 0.000 description 11
- 230000001965 increasing effect Effects 0.000 description 11
- 231100000419 toxicity Toxicity 0.000 description 11
- 230000001988 toxicity Effects 0.000 description 11
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 10
- 206010020843 Hyperthermia Diseases 0.000 description 10
- 230000036031 hyperthermia Effects 0.000 description 10
- 230000002285 radioactive effect Effects 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 229940001474 sodium thiosulfate Drugs 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- 159000000009 barium salts Chemical class 0.000 description 8
- 238000001990 intravenous administration Methods 0.000 description 8
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 229940032330 sulfuric acid Drugs 0.000 description 8
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 7
- 241000283973 Oryctolagus cuniculus Species 0.000 description 7
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- 229940046892 lead acetate Drugs 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- XLSLFPQAPYONPW-WHUHBCJBSA-N (2s,3s,4s,5r,6r)-6-[(r)-cyano(phenyl)methoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O[C@@H](C#N)C1=CC=CC=C1 XLSLFPQAPYONPW-WHUHBCJBSA-N 0.000 description 5
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-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/34—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving hydrolase
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/5005—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
- G01N33/5091—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing the pathological state of an organism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2123/00—Preparations for testing in vivo
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q2334/00—O-linked chromogens for determinations of hydrolase enzymes, e.g. glycosidases, phosphatases, esterases
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
- G01N2333/90—Enzymes; Proenzymes
- G01N2333/914—Hydrolases (3)
- G01N2333/924—Hydrolases (3) acting on glycosyl compounds (3.2)
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Immunology (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Genetics & Genomics (AREA)
- Physics & Mathematics (AREA)
- Urology & Nephrology (AREA)
- Microbiology (AREA)
- Biomedical Technology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Analytical Chemistry (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Physiology (AREA)
- Cell Biology (AREA)
- General Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Food Science & Technology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pathology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US951,270 | 1978-10-13 | ||
| US951,269 | 1978-10-13 | ||
| US05/951,270 US4424348A (en) | 1978-10-13 | 1978-10-13 | Methods of manufacture of nitrile-containing glucuronic acid conjugates |
| US05/951,269 US4584368A (en) | 1978-10-13 | 1978-10-13 | β-Glucuronidase activity and/or pH-dependent pharmaceuticals and thier methods of production |
| US11,619 | 1979-02-12 | ||
| US06/011,619 US4327074A (en) | 1978-10-13 | 1979-02-12 | Method for diagnosis and selective treatment of infections of bacteria having β-glucuronidase activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1148086A true CA1148086A (en) | 1983-06-14 |
Family
ID=27359461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000337483A Expired CA1148086A (en) | 1978-10-13 | 1979-10-12 | .beta.-GLUCURONIDASE ACTIVITY AND/OR PH-DEPENDENT PHARMACEUTICALS AND THEIR METHODS OF PRODUCTION AND USE FOR SELECTIVE TREATMENT OF DISEASES |
Country Status (12)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4490523A (en) * | 1981-11-10 | 1984-12-25 | Ely J. Rubin | Mandelonitrile triacetyl glucuronate and process for preparing same |
| AU594855B2 (en) * | 1988-01-15 | 1990-03-15 | Baker Norton Pharmaceuticals, Inc. | Glucuronic acid derivatives of opioid antagonists |
| DE59610819D1 (de) * | 1995-03-30 | 2003-12-18 | Werner Kreutz | Arzneistoffe zur selektiven bekämpfung von tumorgewebe |
| WO2014138722A1 (en) * | 2013-03-08 | 2014-09-12 | Cognate3 Llc | Process for the preparation of a non-corrosive base solution and methods of using same |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB788855A (en) * | 1953-06-30 | 1958-01-08 | Ernst Theodore Krebs | Improvements in or relating to mandelo-nitrile-glucuronosides and method of making the same |
| US2985664A (en) * | 1957-05-29 | 1961-05-23 | Ernst T Krebs | Hexuronic acid derivatives |
| US3758455A (en) * | 1970-05-14 | 1973-09-11 | Chugai Pharmaceutical Co Ltd | Reof mycophenolic acid glucuronide and the process for the preparation the |
| DE2212014A1 (de) * | 1971-04-21 | 1972-10-26 | Deutsche Akademie der Wissenschaf ten zu Berlin, χ 1199 Berlin | Verfahren zur fermentativen Spaltung von Transportformen von Chemotherapeutika, insbesondere Cancerostatica |
| USRE29465E (en) * | 1972-08-14 | 1977-11-01 | Eli Lilly And Company | Psoriasis treatment with mycophenolic acid |
| US3880995A (en) * | 1973-05-14 | 1975-04-29 | Lilly Co Eli | Treatment of arthritis with mycophenolic acid and derivatives |
| US3959253A (en) * | 1973-07-02 | 1976-05-25 | Merck & Co., Inc. | β-D-glucosyluronic acid derivatives |
| JPS5325534A (en) * | 1976-08-24 | 1978-03-09 | Rikagaku Kenkyusho | Mandelic acid glucosides and their anti-cancerous preparations |
-
1979
- 1979-09-24 AU AU51120/79A patent/AU534068B2/en not_active Ceased
- 1979-09-28 IL IL58352A patent/IL58352A/xx unknown
- 1979-10-02 JP JP50180979A patent/JPS55500837A/ja active Pending
- 1979-10-02 WO PCT/US1979/000809 patent/WO1980000791A1/en unknown
- 1979-10-02 DE DE792953223T patent/DE2953223T1/de active Granted
- 1979-10-02 GB GB8015763A patent/GB2055044B/en not_active Expired
- 1979-10-02 NL NL7920107A patent/NL7920107A/nl unknown
- 1979-10-02 CH CH4668/80A patent/CH652724A5/de not_active IP Right Cessation
- 1979-10-10 FR FR7925183A patent/FR2440374B1/fr not_active Expired
- 1979-10-11 IT IT50529/79A patent/IT1164730B/it active
- 1979-10-12 CA CA000337483A patent/CA1148086A/en not_active Expired
-
1980
- 1980-04-30 FR FR8009746A patent/FR2449284A1/fr not_active Withdrawn
- 1980-06-12 SE SE8004369A patent/SE461983B/sv not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IT1164730B (it) | 1987-04-15 |
| CH652724A5 (de) | 1985-11-29 |
| FR2449284A1 (fr) | 1980-09-12 |
| AU534068B2 (en) | 1984-01-05 |
| SE8004369L (sv) | 1980-06-12 |
| AU5112079A (en) | 1981-04-16 |
| JPS55500837A (enrdf_load_stackoverflow) | 1980-10-23 |
| FR2440374A1 (fr) | 1980-05-30 |
| GB2055044A (en) | 1981-02-25 |
| DE2953223T1 (de) | 1980-11-27 |
| WO1980000791A1 (en) | 1980-05-01 |
| FR2440374B1 (fr) | 1986-03-21 |
| NL7920107A (nl) | 1980-08-29 |
| IL58352A (en) | 1985-11-29 |
| GB2055044B (en) | 1983-04-20 |
| DE2953223C2 (enrdf_load_stackoverflow) | 1989-05-18 |
| IT7950529A0 (it) | 1979-10-11 |
| SE461983B (sv) | 1990-04-23 |
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| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20000614 |