SE451842B - Vattenlosliga 3-formylrifamycin-sv-hydrazoner samt farmaceutiska kompositioner innehallande dessa substanser - Google Patents
Vattenlosliga 3-formylrifamycin-sv-hydrazoner samt farmaceutiska kompositioner innehallande dessa substanserInfo
- Publication number
- SE451842B SE451842B SE8004739A SE8004739A SE451842B SE 451842 B SE451842 B SE 451842B SE 8004739 A SE8004739 A SE 8004739A SE 8004739 A SE8004739 A SE 8004739A SE 451842 B SE451842 B SE 451842B
- Authority
- SE
- Sweden
- Prior art keywords
- water
- represents hydrogen
- formula
- rifamycin
- formylrifamycin
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- BBNQHOMJRFAQBN-UPZFVJMDSA-N 3-formylrifamycin sv Chemical compound OC1=C(C(O)=C2C)C3=C(O)C(C=O)=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O BBNQHOMJRFAQBN-UPZFVJMDSA-N 0.000 title description 7
- 239000000126 substance Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 21
- HJYYPODYNSCCOU-ODRIEIDWSA-N rifamycin SV Chemical class OC1=C(C(O)=C2C)C3=C(O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O HJYYPODYNSCCOU-ODRIEIDWSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 6
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- -1 ethylene, methylethylene Chemical group 0.000 claims description 4
- 238000007911 parenteral administration Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000000844 anti-bacterial effect Effects 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N ethyl ethylene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 229910052708 sodium Chemical group 0.000 claims 1
- 239000011734 sodium Chemical group 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229930189077 Rifamycin Natural products 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229960003292 rifamycin Drugs 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229940109171 rifamycin sv Drugs 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241001342522 Vampyrum spectrum Species 0.000 description 3
- 150000002429 hydrazines Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- WMBUGMHMGTWCSH-UHFFFAOYSA-N 2-hydrazinylethyl dihydrogen phosphate Chemical compound NNCCOP(O)(O)=O WMBUGMHMGTWCSH-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QJWPFBOBVOXAEH-UHFFFAOYSA-N 1-[amino(methyl)amino]butan-2-ol Chemical compound CCC(O)CN(C)N QJWPFBOBVOXAEH-UHFFFAOYSA-N 0.000 description 1
- ZXOGWYNJXRYOEU-UHFFFAOYSA-N 2-[amino(methyl)amino]ethanol Chemical compound CN(N)CCO ZXOGWYNJXRYOEU-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- HJYYPODYNSCCOU-ZDHWWVNNSA-N Rifamycin SV Natural products COC1C=COC2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C)cc(O)c4c3C2=O HJYYPODYNSCCOU-ZDHWWVNNSA-N 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003885 eye ointment Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- BTVYFIMKUHNOBZ-QXMMDKDBSA-N rifamycin s Chemical class O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)\C(C)=C/C=C\C(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C(C)C(OC)\C=C/OC1(C)OC2=C3C1=O BTVYFIMKUHNOBZ-QXMMDKDBSA-N 0.000 description 1
- 229940081192 rifamycins Drugs 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/08—Bridged systems
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7922461 | 1979-06-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8004739L SE8004739L (sv) | 1980-12-29 |
| SE451842B true SE451842B (sv) | 1987-11-02 |
Family
ID=10506154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8004739A SE451842B (sv) | 1979-06-28 | 1980-06-26 | Vattenlosliga 3-formylrifamycin-sv-hydrazoner samt farmaceutiska kompositioner innehallande dessa substanser |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4271155A (it) |
| JP (1) | JPS5618993A (it) |
| KR (1) | KR830002533B1 (it) |
| AR (1) | AR225181A1 (it) |
| AU (1) | AU536524B2 (it) |
| CA (1) | CA1114814A (it) |
| DE (1) | DE3024304A1 (it) |
| DK (1) | DK155742C (it) |
| FR (1) | FR2460304A1 (it) |
| GB (1) | GB2051815B (it) |
| HK (1) | HK23684A (it) |
| IE (1) | IE49930B1 (it) |
| IT (1) | IT1209333B (it) |
| NL (1) | NL8003527A (it) |
| NZ (1) | NZ194144A (it) |
| PH (1) | PH15769A (it) |
| SE (1) | SE451842B (it) |
| ZA (1) | ZA803635B (it) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004096285A2 (en) * | 2003-04-25 | 2004-11-11 | Gilead Sciences, Inc. | Anti-infective phosphonate conjugates |
| JP5368092B2 (ja) * | 2005-08-11 | 2013-12-18 | ターガンタ セラピュティクス，インコーポレイティド | ホスホン化リファマイシン類および骨と関節感染の予防と治療のためのその投与法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR208F (it) * | 1964-07-31 | |||
| FR5223M (it) * | 1965-11-12 | 1967-07-10 | ||
| US4005076A (en) * | 1971-06-24 | 1977-01-25 | Gruppo Lepetit S.P.A. | Hydrazones of 3-formylrifamycin SV |
| BE794100A (fr) * | 1972-02-23 | 1973-05-16 | Lepetit Spa | Derives 3-hydrazonomethyles de rifamycine et leur preparation |
| AR205434A1 (es) * | 1972-03-27 | 1976-05-07 | Lepetit Spa | Proceso para la preparacion de 3-acilhidrazonometil rifamicinas sv |
| GB1478563A (en) * | 1975-03-05 | 1977-07-06 | Lepetit Spa | Rifamycin derivatives |
| GB1486118A (en) * | 1975-03-05 | 1977-09-21 | Lepetit Spa | Rifamycin derivatives |
| GR64108B (en) * | 1977-04-15 | 1980-01-24 | Dso Pharmachim | Method for the preparation of azomethine-derivatives of rifamycin s.v |
-
1980
- 1980-06-10 AU AU59188/80A patent/AU536524B2/en not_active Ceased
- 1980-06-17 IT IT8022817A patent/IT1209333B/it active
- 1980-06-18 ZA ZA00803635A patent/ZA803635B/xx unknown
- 1980-06-18 GB GB8019904A patent/GB2051815B/en not_active Expired
- 1980-06-18 NL NL8003527A patent/NL8003527A/nl not_active Application Discontinuation
- 1980-06-19 US US06/160,799 patent/US4271155A/en not_active Expired - Lifetime
- 1980-06-24 DK DK269380A patent/DK155742C/da not_active IP Right Cessation
- 1980-06-25 NZ NZ194144A patent/NZ194144A/en unknown
- 1980-06-26 AR AR281548A patent/AR225181A1/es active
- 1980-06-26 SE SE8004739A patent/SE451842B/sv not_active IP Right Cessation
- 1980-06-26 JP JP8600480A patent/JPS5618993A/ja active Granted
- 1980-06-26 FR FR8014247A patent/FR2460304A1/fr active Granted
- 1980-06-27 PH PH24203A patent/PH15769A/en unknown
- 1980-06-27 CA CA354,957A patent/CA1114814A/en not_active Expired
- 1980-06-27 IE IE1346/80A patent/IE49930B1/en not_active IP Right Cessation
- 1980-06-27 DE DE19803024304 patent/DE3024304A1/de active Granted
- 1980-06-28 KR KR1019800002558A patent/KR830002533B1/ko active
-
1984
- 1984-03-15 HK HK236/84A patent/HK23684A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL8003527A (nl) | 1980-12-30 |
| AU5918880A (en) | 1981-01-08 |
| AU536524B2 (en) | 1984-05-10 |
| FR2460304A1 (fr) | 1981-01-23 |
| IE49930B1 (en) | 1986-01-08 |
| PH15769A (en) | 1983-03-24 |
| JPS5618993A (en) | 1981-02-23 |
| SE8004739L (sv) | 1980-12-29 |
| KR830002533B1 (ko) | 1983-11-12 |
| ZA803635B (en) | 1981-06-24 |
| IT8022817A0 (it) | 1980-06-17 |
| DK155742C (da) | 1989-09-18 |
| US4271155A (en) | 1981-06-02 |
| KR830002767A (ko) | 1983-05-30 |
| FR2460304B1 (it) | 1984-07-27 |
| GB2051815B (en) | 1983-07-06 |
| HK23684A (en) | 1984-03-23 |
| DK269380A (da) | 1980-12-29 |
| DE3024304A1 (de) | 1981-02-05 |
| GB2051815A (en) | 1981-01-21 |
| DE3024304C2 (it) | 1991-10-31 |
| IT1209333B (it) | 1989-07-16 |
| CA1114814A (en) | 1981-12-22 |
| IE801346L (en) | 1980-12-28 |
| JPS6348877B2 (it) | 1988-09-30 |
| AR225181A1 (es) | 1982-02-26 |
| DK155742B (da) | 1989-05-08 |
| NZ194144A (en) | 1984-05-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7915303B2 (en) | Glycopyrronium salts and their therapeutic use | |
| EP3978472A1 (en) | Biaryl monabactam compounds and methods of use thereof for the treatment of bacterial infections | |
| CA1283656C (en) | Deoxyadenosine phosphate compounds and methods of making and using the same | |
| DE68906183T2 (de) | 2'-desoxy-5-fluoruridinderivate. | |
| EP2020416A1 (en) | Phosphonocephem compound | |
| PT89009B (pt) | Processo para a preparacao de novos derivados de fluorocitidina e composicoes farmaceuticas que os contem' | |
| US4512998A (en) | Anthelmintic benzimidazole carbamates | |
| SU1604158A3 (ru) | Способ получени производных гризеоловой кислоты | |
| US4636508A (en) | 5-pyrimidinecarboxyamides and treatment of leukemia therewith | |
| Fletcher et al. | Preparation of O, O-diethyl Op-nitrophenyl thiophosphate (parathion) | |
| GB1599928A (en) | Process for producing glycopyranosenitrosourea compounds and a compound included therein | |
| US4727065A (en) | Bis-(2-ammonium-2-hydroxymethyl-1,3-propanediol(2R-cis)-(3-methyloxiranyl)-phosphonate, a method of preparing same, and pharmaceutical compositions containing same | |
| EP0027597B1 (en) | Mono(2-ammonium-2-hydroxymethyl-1,3-propanediol)(2r-cis)-(3-methyloxiranyl)phosphonate, its preparation and pharmaceutical compositions containing it | |
| US4406893A (en) | N-Alkoxycarbonyl-N'-[2-nitro-4 or 5-alkylthiophenyl]-N"-[substituted alkyl]-guanidines useful as anthelmintics | |
| KR0178956B1 (ko) | 항균성 페넴 에스테르 유도체 | |
| SE451842B (sv) | Vattenlosliga 3-formylrifamycin-sv-hydrazoner samt farmaceutiska kompositioner innehallande dessa substanser | |
| US4567169A (en) | Nitrosourea substituted phosphonates and pharmaceutical use | |
| EP1284984B1 (fr) | Derives de l'uridine comme antibiotiques | |
| US3836656A (en) | Substituted purines as hypolipidemics | |
| US4544501A (en) | Bis(2,2-dimethyl-1-aziridinyl)phosphinic amides for use in the treatment of tumors | |
| DE69815380T2 (de) | N,n'-bis (sulfonyl) hydrazine die als antineoplastische mittel nützlich sind | |
| PL170798B1 (pl) | Sposób wytwarzania krystalicznych soli addycyjnych z kwasem obydwóch poszczególnych diastereomerówestru 1-(2,2-dimetylopropionyloksy)-etylowego kwasu 3-cefem-4-karboksylowego PL PL | |
| US4920126A (en) | Barbituric acid derivative and treatment of leukemia and tumors therewith | |
| HU197568B (en) | Process for producing crystalline salts of square brackets open 3siz square brackets closed-2-brackets open square brackets open square brackets open 1-/2-amino-4-thiazolyl/-2-square brackets open square brackets open 2,2-dimethyl-4-oxo-1-sulfoxy-3-azetidinyl square brackets closed-amino square brackets closed-2-oxoehtylidene square brackets closed-amino square brackets closed-oxy brackets closed acetic acid and pharmaceuticals comprising same as active ingredient | |
| US4218465A (en) | Glyoxylic acid hydrocarbylsulfonylhydrazones and therapeutic compositions |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
Ref document number: 8004739-2 Effective date: 19950110 Format of ref document f/p: F |
|
| NUG | Patent has lapsed |
Ref document number: 8004739-2 Format of ref document f/p: F |