CA1300005C - Sterilization of compositions of limited stability - Google Patents
Sterilization of compositions of limited stabilityInfo
- Publication number
- CA1300005C CA1300005C CA000558096A CA558096A CA1300005C CA 1300005 C CA1300005 C CA 1300005C CA 000558096 A CA000558096 A CA 000558096A CA 558096 A CA558096 A CA 558096A CA 1300005 C CA1300005 C CA 1300005C
- Authority
- CA
- Canada
- Prior art keywords
- buffer
- formulation
- sterilization
- drug
- range
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 47
- 230000001954 sterilising effect Effects 0.000 title claims abstract description 21
- 238000004659 sterilization and disinfection Methods 0.000 title claims abstract description 13
- 239000000872 buffer Substances 0.000 claims abstract description 32
- 238000009472 formulation Methods 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 28
- 239000003690 nonionic contrast media Substances 0.000 claims description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical group [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 8
- 150000007942 carboxylates Chemical class 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000007853 buffer solution Substances 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- 239000013011 aqueous formulation Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract description 25
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract description 19
- 229940079593 drug Drugs 0.000 abstract description 19
- 239000003814 drug Substances 0.000 abstract description 19
- 239000001569 carbon dioxide Substances 0.000 abstract description 12
- 239000013583 drug formulation Substances 0.000 abstract description 4
- 206010053567 Coagulopathies Diseases 0.000 abstract description 3
- 230000003139 buffering effect Effects 0.000 abstract description 3
- 230000035602 clotting Effects 0.000 abstract description 3
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 239000002872 contrast media Substances 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 229940039231 contrast media Drugs 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 4
- 239000000306 component Substances 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 238000011067 equilibration Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000002586 coronary angiography Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000004217 heart function Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 229960002611 ioxilan Drugs 0.000 description 2
- UUMLTINZBQPNGF-UHFFFAOYSA-N ioxilan Chemical compound OCC(O)CN(C(=O)C)C1=C(I)C(C(=O)NCCO)=C(I)C(C(=O)NCC(O)CO)=C1I UUMLTINZBQPNGF-UHFFFAOYSA-N 0.000 description 2
- -1 of up to about 4 Chemical class 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 229910001415 sodium ion Inorganic materials 0.000 description 2
- FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 1
- RBNPOMFGQQGHHO-UWTATZPHSA-N D-glyceric acid Chemical compound OC[C@@H](O)C(O)=O RBNPOMFGQQGHHO-UWTATZPHSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- BAQCROVBDNBEEB-UBYUBLNFSA-N Metrizamide Chemical compound CC(=O)N(C)C1=C(I)C(NC(C)=O)=C(I)C(C(=O)N[C@@H]2[C@H]([C@H](O)[C@@H](CO)OC2O)O)=C1I BAQCROVBDNBEEB-UBYUBLNFSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 206010047095 Vascular pain Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- YVPYQUNUQOZFHG-UHFFFAOYSA-N amidotrizoic acid Chemical compound CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I YVPYQUNUQOZFHG-UHFFFAOYSA-N 0.000 description 1
- 238000002583 angiography Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001767 cationic compounds Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 229940097042 glucuronate Drugs 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 208000021267 infertility disease Diseases 0.000 description 1
- 229910001411 inorganic cation Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 229960001025 iohexol Drugs 0.000 description 1
- NTHXOOBQLCIOLC-UHFFFAOYSA-N iohexol Chemical compound OCC(O)CN(C(=O)C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NTHXOOBQLCIOLC-UHFFFAOYSA-N 0.000 description 1
- 239000002611 ionic contrast media Substances 0.000 description 1
- OLAOYPRJVHUHCF-UHFFFAOYSA-N iooxitalamic acid Chemical compound CC(=O)NC1=C(I)C(C(O)=O)=C(I)C(C(=O)NCCO)=C1I OLAOYPRJVHUHCF-UHFFFAOYSA-N 0.000 description 1
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229960000554 metrizamide Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/0005—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor for pharmaceuticals, biologicals or living parts
- A61L2/0011—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor for pharmaceuticals, biologicals or living parts using physical methods
- A61L2/0023—Heat
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/02—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using physical phenomena
- A61L2/04—Heat
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/90—In vivo diagnostic or in vivo test agent which contains an additional ingredient to reduce the toxicity or side effects of the active ingredient
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/011,016 US4863714A (en) | 1987-02-05 | 1987-02-05 | Sterilization of compositions of limited stability |
| US011,016 | 1993-01-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1300005C true CA1300005C (en) | 1992-05-05 |
Family
ID=21748489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000558096A Expired - Lifetime CA1300005C (en) | 1987-02-05 | 1988-02-04 | Sterilization of compositions of limited stability |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4863714A (enExample) |
| EP (1) | EP0278674B1 (enExample) |
| JP (1) | JPH0667855B2 (enExample) |
| AT (1) | ATE79279T1 (enExample) |
| AU (1) | AU607461B2 (enExample) |
| CA (1) | CA1300005C (enExample) |
| DE (1) | DE3873553T2 (enExample) |
| ES (1) | ES2034184T3 (enExample) |
| GR (1) | GR3006111T3 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8906130D0 (en) * | 1989-03-17 | 1989-05-04 | Nycomed As | Compositions |
| GB9020091D0 (en) * | 1990-09-14 | 1990-10-24 | Nycomed As | Contrast media |
| DE4015832A1 (de) * | 1990-05-17 | 1991-11-21 | Thomae Gmbh Dr K | Verfahren zur inaktivierung der biologischen aktivitaet von dna |
| DE69527923T2 (de) * | 1994-07-01 | 2003-04-24 | Baxter International Inc., Deerfield | Biochemisch isotone peritonealdialyselösungen |
| US5605934A (en) * | 1995-03-23 | 1997-02-25 | Baxter International Inc. | Method of manufacturing and storing solutions |
| US5972225A (en) * | 1996-05-07 | 1999-10-26 | Cook Imaging Corporation | Process for remediating endotoxin-contaminated bulk non-ionic contrast media |
| US6309673B1 (en) | 1999-09-10 | 2001-10-30 | Baxter International Inc. | Bicarbonate-based solution in two parts for peritoneal dialysis or substitution in continuous renal replacement therapy |
| US7122210B2 (en) * | 2002-01-11 | 2006-10-17 | Baxter International Inc. | Bicarbonate-based solutions for dialysis therapies |
| US7445801B2 (en) * | 2002-06-07 | 2008-11-04 | Baxter International Inc. | Stable bicarbonate-based solution in a single container |
| US20060094700A1 (en) * | 2004-11-02 | 2006-05-04 | Allergan, Inc. | Heat sterilization of a steroid in the presence of phosphate |
| US7935070B2 (en) * | 2005-01-28 | 2011-05-03 | Fresenius Medical Care North America | Systems and methods for dextrose containing peritoneal dialysis (PD) solutions with neutral pH and reduced glucose degradation product |
| JPWO2008146731A1 (ja) * | 2007-05-25 | 2010-08-19 | 味の素株式会社 | 末梢静脈投与用輸液の製造方法 |
| BR112012023063A2 (pt) * | 2010-03-23 | 2016-05-17 | Ge Healthcare As | processo para a preparação de uma composição para raio x, e, composição de diagnóstico para raio x |
| US9585810B2 (en) | 2010-10-14 | 2017-03-07 | Fresenius Medical Care Holdings, Inc. | Systems and methods for delivery of peritoneal dialysis (PD) solutions with integrated inter-chamber diffuser |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4224440A (en) * | 1975-05-15 | 1980-09-23 | Mallinckrodt, Inc. | 1-(3,5-Disubstituted-2,4,6-triiodophenly)-3-(polyhydroxy-alkyl)urea compounds |
| GB2031405B (en) * | 1978-07-04 | 1983-06-15 | Nyegaard & Co As | Process for the preparation of a sterile injectable physiologically acceptable solution of an x-ray contrast agent and solutions of the x-ray contrast agent and a buffer |
| KR830001643B1 (ko) * | 1978-07-04 | 1983-08-22 | 울프 블릭스 | X-선 조영제의 생리적으로 허용되는 멸균 주사용 용액을 제조하는 방법 |
| FR2571367B1 (fr) * | 1984-10-09 | 1987-02-13 | Guerbet Sa | Composes triaminobenzeniques iodes et/ou bromes, leur procede de preparation et leur application dans des produits de contraste |
| GB8717625D0 (en) * | 1987-07-24 | 1987-09-03 | Nycomed As | Chemical compounds |
-
1987
- 1987-02-05 US US07/011,016 patent/US4863714A/en not_active Expired - Fee Related
-
1988
- 1988-02-04 CA CA000558096A patent/CA1300005C/en not_active Expired - Lifetime
- 1988-02-04 JP JP63022941A patent/JPH0667855B2/ja not_active Expired - Lifetime
- 1988-02-04 AT AT88300926T patent/ATE79279T1/de not_active IP Right Cessation
- 1988-02-04 EP EP88300926A patent/EP0278674B1/en not_active Expired - Lifetime
- 1988-02-04 ES ES198888300926T patent/ES2034184T3/es not_active Expired - Lifetime
- 1988-02-04 DE DE8888300926T patent/DE3873553T2/de not_active Expired - Lifetime
- 1988-02-05 AU AU11336/88A patent/AU607461B2/en not_active Expired
-
1992
- 1992-10-29 GR GR920402432T patent/GR3006111T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU607461B2 (en) | 1991-03-07 |
| EP0278674B1 (en) | 1992-08-12 |
| AU1133688A (en) | 1988-08-11 |
| DE3873553D1 (de) | 1992-09-17 |
| ES2034184T3 (es) | 1993-04-01 |
| EP0278674A3 (en) | 1989-07-19 |
| JPH01221330A (ja) | 1989-09-04 |
| DE3873553T2 (de) | 1993-02-18 |
| JPH0667855B2 (ja) | 1994-08-31 |
| EP0278674A2 (en) | 1988-08-17 |
| GR3006111T3 (enExample) | 1993-06-21 |
| ATE79279T1 (de) | 1992-08-15 |
| US4863714A (en) | 1989-09-05 |
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