LU86540A1 - Sels de cephalosporine et compositions injectables - Google Patents
Sels de cephalosporine et compositions injectables Download PDFInfo
- Publication number
- LU86540A1 LU86540A1 LU86540A LU86540A LU86540A1 LU 86540 A1 LU86540 A1 LU 86540A1 LU 86540 A LU86540 A LU 86540A LU 86540 A LU86540 A LU 86540A LU 86540 A1 LU86540 A1 LU 86540A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- mixture
- crystalline
- salts
- sulfuric acid
- ion
- Prior art date
Links
- 239000007972 injectable composition Substances 0.000 title description 11
- 229930186147 Cephalosporin Natural products 0.000 title description 5
- 229940124587 cephalosporin Drugs 0.000 title description 5
- 150000001780 cephalosporins Chemical class 0.000 title description 4
- 150000003839 salts Chemical class 0.000 claims description 79
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 50
- 150000002500 ions Chemical class 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 229910001868 water Inorganic materials 0.000 claims description 25
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 24
- 238000002425 crystallisation Methods 0.000 claims description 19
- 230000008025 crystallization Effects 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 17
- -1 2-amino-thiazol-4-yl Chemical group 0.000 claims description 15
- 239000006069 physical mixture Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- 238000000926 separation method Methods 0.000 claims description 9
- 230000000977 initiatory effect Effects 0.000 claims description 8
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical group NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 7
- 229960003646 lysine Drugs 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 235000011007 phosphoric acid Nutrition 0.000 claims description 7
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical group OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 6
- 238000007865 diluting Methods 0.000 claims description 5
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 5
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 4
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 3
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 56
- 239000013078 crystal Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 13
- 238000003828 vacuum filtration Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 11
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000010790 dilution Methods 0.000 description 6
- 239000012895 dilution Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 238000010899 nucleation Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000008223 sterile water Substances 0.000 description 4
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229960004261 cefotaxime Drugs 0.000 description 2
- AZZMGZXNTDTSME-JUZDKLSSSA-M cefotaxime sodium Chemical compound [Na+].N([C@@H]1C(N2C(=C(COC(C)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 AZZMGZXNTDTSME-JUZDKLSSSA-M 0.000 description 2
- ORFOPKXBNMVMKC-DWVKKRMSSA-N ceftazidime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 ORFOPKXBNMVMKC-DWVKKRMSSA-N 0.000 description 2
- 229960000484 ceftazidime Drugs 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 238000005057 refrigeration Methods 0.000 description 2
- 230000035807 sensation Effects 0.000 description 2
- 239000001509 sodium citrate Substances 0.000 description 2
- 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 description 2
- 238000001228 spectrum Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- HVFLCNVBZFFHBT-ZKDACBOMSA-N cefepime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1C[N+]1(C)CCCC1 HVFLCNVBZFFHBT-ZKDACBOMSA-N 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 150000003952 β-lactams Chemical class 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing 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)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76223585A | 1985-08-05 | 1985-08-05 | |
| US76223585 | 1985-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU86540A1 true LU86540A1 (fr) | 1987-03-06 |
Family
ID=25064475
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU86540A LU86540A1 (fr) | 1985-08-05 | 1986-08-04 | Sels de cephalosporine et compositions injectables |
| LU88574C LU88574I2 (fr) | 1985-08-05 | 1986-08-04 | CEFEPIME et ses sels pharmaceutiquement acceptables (Maxipime R) |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU88574C LU88574I2 (fr) | 1985-08-05 | 1986-08-04 | CEFEPIME et ses sels pharmaceutiquement acceptables (Maxipime R) |
Country Status (34)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4883868A (en) * | 1984-12-27 | 1989-11-28 | Banyu Pharmaceutical Co., Ltd. | 7-amino-3-(substituted isoindolinium)methyl-3-cephem derivatives |
| US4959469A (en) * | 1984-12-27 | 1990-09-25 | Banyu Pharmaceutical Company, Ltd. | Crystalline cephalosporin compounds |
| US4910301A (en) * | 1985-08-05 | 1990-03-20 | Bristol-Myers Company | Cefepime cephalosporin salts |
| US5244891A (en) * | 1985-08-05 | 1993-09-14 | Bristol-Myers Squibb Company | Injectable compositions of cefepime dihydrochloride hydrate |
| US4808617A (en) * | 1985-12-18 | 1989-02-28 | Bristol-Myers Company | Lyophilized or precipitated cephalosporin zwitterion and salt combination |
| DE3788279T2 (de) * | 1987-06-25 | 1994-06-16 | Banyu Pharma Co Ltd | Kristalline cephalosporinzusammensetzungen, verfahren und zwischenprodukte für ihre herstellung. |
| JPH02101081A (ja) * | 1988-10-08 | 1990-04-12 | Meiji Seika Kaisha Ltd | セファロスポリン誘導体結晶性二塩酸塩及びその製造法 |
| CA2011116C (en) * | 1989-03-06 | 1999-11-16 | Murray A. Kaplan | Lyophilized bmy-28142 dihydrochloride for parenteral use |
| CA2101571A1 (en) * | 1992-09-08 | 1994-03-09 | Elizabeth A. Garofalo | Crystalline dihydrate of a cephalosporin dihydrate salt and injectable compositions thereof |
| JP3852946B2 (ja) * | 1993-03-12 | 2006-12-06 | ファルマシア・アンド・アップジョン・カンパニー | 結晶性セフチオフル遊離酸 |
| EP0638573A1 (en) * | 1993-08-10 | 1995-02-15 | Lucky Ltd. | Crystalline hydrates of cephalosporin and process for preparation thereof |
| ES2298850T3 (es) | 2003-12-23 | 2008-05-16 | Sandoz Gmbh | Proceso para la produccion de intermedios para utilizar en la sintesis de la cefalosporina. |
| WO2008056221A2 (en) * | 2006-11-06 | 2008-05-15 | Orchid Chemicals & Pharmaceuticals Limited | Crystalline sulfate salt of cephalosporin antibiotic |
| DE102012101680A1 (de) * | 2012-02-29 | 2013-08-29 | Aicuris Gmbh & Co. Kg | Pharmazeutische Zubereitung enthaltend ein antiviral wirksames Dihydrochinazolinderivat |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55151588A (en) * | 1979-05-14 | 1980-11-26 | Takeda Chem Ind Ltd | Preparation of cephalosporin salt crystal |
| US4406899A (en) * | 1982-03-04 | 1983-09-27 | Bristol-Myers Company | Cephalosporins |
| CA1213882A (en) * | 1982-03-04 | 1986-11-12 | Jun Okumura | Cephalosporins |
| US4525473A (en) * | 1983-03-30 | 1985-06-25 | Bristol-Myers Company | Cephalosporins |
| DE3419015A1 (de) * | 1984-05-22 | 1985-11-28 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von cephalosporinen |
| GB2165245B (en) * | 1984-10-01 | 1988-05-25 | Glaxo Group Ltd | Chemical compounds |
| GB8424692D0 (en) * | 1984-10-01 | 1984-11-07 | Glaxo Group Ltd | Chemical compounds |
-
1986
- 1986-07-28 CA CA000514766A patent/CA1284994C/en not_active Expired - Lifetime
- 1986-07-28 FR FR8610892A patent/FR2585705B1/fr not_active Expired
- 1986-07-29 AR AR86304717A patent/AR243894A1/es active
- 1986-07-30 AU AU60694/86A patent/AU597262B2/en not_active Expired
- 1986-07-31 YU YU137186A patent/YU45793B/sh unknown
- 1986-08-01 IE IE207886A patent/IE59222B1/en not_active IP Right Cessation
- 1986-08-01 FI FI863155A patent/FI84484C/fi not_active IP Right Cessation
- 1986-08-04 IL IL79608A patent/IL79608A/xx not_active IP Right Cessation
- 1986-08-04 GB GB8618989A patent/GB2179936B/en not_active Expired
- 1986-08-04 NL NL8601991A patent/NL8601991A/nl not_active Application Discontinuation
- 1986-08-04 CH CH3117/86A patent/CH675581A5/de not_active IP Right Cessation
- 1986-08-04 LU LU86540A patent/LU86540A1/fr unknown
- 1986-08-04 SE SE8603308A patent/SE469633B/sv not_active IP Right Cessation
- 1986-08-04 SU SU864027914A patent/SU1516013A3/ru active
- 1986-08-04 CS CS865827A patent/CS276717B6/cs unknown
- 1986-08-04 DK DK371886A patent/DK162053C/da not_active IP Right Cessation
- 1986-08-04 CS CS903570A patent/CS276849B6/cs unknown
- 1986-08-04 ZA ZA865842A patent/ZA865842B/xx unknown
- 1986-08-04 GR GR862055A patent/GR862055B/el unknown
- 1986-08-04 BE BE07217010A patent/BE905219A/fr not_active IP Right Cessation
- 1986-08-04 PT PT83134A patent/PT83134B/pt unknown
- 1986-08-04 IT IT21409/86A patent/IT1197067B/it active Protection Beyond IP Right Term
- 1986-08-04 LU LU88574C patent/LU88574I2/fr unknown
- 1986-08-04 JP JP61183288A patent/JPH0615548B2/ja not_active Expired - Lifetime
- 1986-08-04 DE DE19863626375 patent/DE3626375A1/de not_active Ceased
- 1986-08-05 ES ES8600872A patent/ES2002112A6/es not_active Expired
- 1986-08-05 DD DD86293433A patent/DD254941A5/de unknown
- 1986-08-05 AT AT0211086A patent/AT390957B/de not_active IP Right Cessation
- 1986-08-05 OA OA58918A patent/OA08672A/xx unknown
- 1986-08-05 KR KR1019860006445A patent/KR930003121B1/ko not_active Expired - Lifetime
- 1986-08-05 HU HU863376A patent/HU196602B/hu unknown
-
1987
- 1987-09-29 MY MYPI87002279A patent/MY102212A/en unknown
-
1988
- 1988-03-30 DD DD88314213A patent/DD268395A5/de unknown
-
1989
- 1989-08-04 EG EG489/86A patent/EG18003A/xx active
-
1991
- 1991-10-02 SG SG797/91A patent/SG79791G/en unknown
- 1991-12-05 HK HK996/91A patent/HK99691A/xx not_active IP Right Cessation
-
1992
- 1992-07-10 CY CY1614A patent/CY1614A/en unknown
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