DK175113B1 - Anvendelse af 5- og 6-leddede heterocycliske forbindelser til fremstilling af et præparat til behandling af patienter inficeret med HIV - Google Patents
Anvendelse af 5- og 6-leddede heterocycliske forbindelser til fremstilling af et præparat til behandling af patienter inficeret med HIV Download PDFInfo
- Publication number
- DK175113B1 DK175113B1 DK198807081A DK708188A DK175113B1 DK 175113 B1 DK175113 B1 DK 175113B1 DK 198807081 A DK198807081 A DK 198807081A DK 708188 A DK708188 A DK 708188A DK 175113 B1 DK175113 B1 DK 175113B1
- Authority
- DK
- Denmark
- Prior art keywords
- dideoxy
- imino
- compound
- methyl
- hiv
- Prior art date
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- 150000000565 5-membered heterocyclic compounds Chemical class 0.000 title 1
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
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- 239000008346 aqueous phase Substances 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
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- 239000013078 crystal Substances 0.000 description 1
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- 238000011161 development Methods 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 230000007614 genetic variation Effects 0.000 description 1
- 230000013595 glycosylation Effects 0.000 description 1
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- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
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- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 208000018555 lymphatic system disease Diseases 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 108010009689 mannosyl-oligosaccharide 1,2-alpha-mannosidase Proteins 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- FDNFXHCDOASWAY-UHFFFAOYSA-N methyl 6-oxohexanoate Chemical compound COC(=O)CCCCC=O FDNFXHCDOASWAY-UHFFFAOYSA-N 0.000 description 1
- HOVAGTYPODGVJG-ZFYZTMLRSA-N methyl alpha-D-glucopyranoside Chemical compound CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HOVAGTYPODGVJG-ZFYZTMLRSA-N 0.000 description 1
- HOVAGTYPODGVJG-UHFFFAOYSA-N methyl beta-galactoside Natural products COC1OC(CO)C(O)C(O)C1O HOVAGTYPODGVJG-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- AXIPBRXJGSXLHF-UHFFFAOYSA-N piperidine;pyrrolidine Chemical compound C1CCNC1.C1CCNCC1 AXIPBRXJGSXLHF-UHFFFAOYSA-N 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000001902 propagating effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003215 pyranoses Chemical class 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- HEBKCHPVOIAQTA-ZXFHETKHSA-N ribitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)CO HEBKCHPVOIAQTA-ZXFHETKHSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- UYCAUPASBSROMS-AWQJXPNKSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-][13C](=O)[13C](F)(F)F UYCAUPASBSROMS-AWQJXPNKSA-M 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
- C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Compounds Of Unknown Constitution (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13621987A | 1987-12-21 | 1987-12-21 | |
| US13621987 | 1987-12-21 | ||
| US24914488 | 1988-09-26 | ||
| US07/249,144 US4999360A (en) | 1987-12-21 | 1988-09-26 | Method of inhibiting virus |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK708188D0 DK708188D0 (da) | 1988-12-20 |
| DK708188A DK708188A (da) | 1989-06-22 |
| DK175113B1 true DK175113B1 (da) | 2004-06-07 |
Family
ID=26834131
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK198807081A DK175113B1 (da) | 1987-12-21 | 1988-12-20 | Anvendelse af 5- og 6-leddede heterocycliske forbindelser til fremstilling af et præparat til behandling af patienter inficeret med HIV |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4999360A (fr) |
| EP (1) | EP0322395B1 (fr) |
| JP (1) | JP2538014B2 (fr) |
| KR (1) | KR910009994B1 (fr) |
| AT (1) | ATE87206T1 (fr) |
| AU (1) | AU607834B2 (fr) |
| CA (1) | CA1316929C (fr) |
| DE (1) | DE3879653T2 (fr) |
| DK (1) | DK175113B1 (fr) |
| FI (1) | FI93210C (fr) |
| IE (1) | IE63095B1 (fr) |
| IL (1) | IL88742A (fr) |
| NO (1) | NO172340C (fr) |
| NZ (1) | NZ227410A (fr) |
| OA (1) | OA08937A (fr) |
| PT (1) | PT89267B (fr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2086323T3 (es) * | 1988-11-03 | 1996-07-01 | Searle & Co | Derivados del didesoxi-arabinitol como compuestos antiviricos. |
| US4894388A (en) * | 1988-12-22 | 1990-01-16 | Monsanto Company | Glycosidase inhibitors and use thereof |
| US5100797A (en) * | 1989-06-27 | 1992-03-31 | Monsanto Company | Fucosidase inhibitors |
| US5043273A (en) * | 1989-08-17 | 1991-08-27 | Monsanto Company | Phosphorylated glycosidase inhibitor prodrugs |
| IT1239950B (it) * | 1990-03-28 | 1993-11-27 | Zambon Spa | Processo per la preparazione di composti con attivita' analgesica centrale |
| US5536732A (en) * | 1990-04-27 | 1996-07-16 | Merrell Pharmaceuticals Inc. | N-derivatives of 1-deoxy nojirimycin |
| US5252587A (en) * | 1990-04-27 | 1993-10-12 | Merrell Dow Pharmaceuticals, Inc. | N-derivatives of 1-deoxy nojirimycin |
| US5290948A (en) * | 1990-09-17 | 1994-03-01 | Mcneilab, Inc. | Process for producing polyhydroxylated piperidines and pyrrolidines and compounds thereof |
| GB9026271D0 (en) * | 1990-12-03 | 1991-01-16 | Alphey Thomas J W | Control of parasitic nematodes(a) |
| US5258518A (en) * | 1992-04-01 | 1993-11-02 | G. D. Searle & Co. | 2-substituted tertiary carbinol derivatives of deoxynojirimycin |
| US5451679A (en) * | 1994-03-08 | 1995-09-19 | G. D. Searle & Co. | 2-chloro and 2-bromo derivatives of 1,5-iminosugars |
| AU724003B2 (en) * | 1995-09-08 | 2000-09-07 | Novo Nordisk A/S | 2-alkylpyrrolidines |
| CN102399228B (zh) * | 2010-09-08 | 2013-10-16 | 中国科学院成都生物研究所 | N-烷基多羟基哌啶衍生物的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1555654A (en) * | 1977-06-25 | 1979-11-14 | Exxon Research Engineering Co | Agricultural burner apparatus |
| US4065562A (en) * | 1975-12-29 | 1977-12-27 | Nippon Shinyaku Co., Ltd. | Method and composition for reducing blood glucose levels |
| DE3038901A1 (de) * | 1980-10-15 | 1982-05-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von n-substituierten derivaten des 1-desoxynojirimycins |
| DE3507019A1 (de) * | 1985-02-28 | 1986-08-28 | Bayer Ag, 5090 Leverkusen | Neue derivate von 3,4,5-trihydroxypiperidin, verfahren zu ihrer herstellung und ihre verwendung |
| EP0252962B1 (fr) * | 1985-12-23 | 1995-08-23 | Fred Hutchinson Cancer Research Center | Regulation de la replication, de l'infection et de la pathogenese retrovirales |
-
1988
- 1988-09-26 US US07/249,144 patent/US4999360A/en not_active Expired - Lifetime
- 1988-12-20 PT PT89267A patent/PT89267B/pt active IP Right Revival
- 1988-12-20 EP EP88870192A patent/EP0322395B1/fr not_active Expired - Lifetime
- 1988-12-20 OA OA59494A patent/OA08937A/fr unknown
- 1988-12-20 DE DE88870192T patent/DE3879653T2/de not_active Expired - Fee Related
- 1988-12-20 FI FI885880A patent/FI93210C/fi not_active IP Right Cessation
- 1988-12-20 CA CA000586466A patent/CA1316929C/fr not_active Expired - Fee Related
- 1988-12-20 KR KR1019880017028A patent/KR910009994B1/ko not_active Expired
- 1988-12-20 NZ NZ227410A patent/NZ227410A/en unknown
- 1988-12-20 IL IL88742A patent/IL88742A/xx not_active IP Right Cessation
- 1988-12-20 JP JP63321868A patent/JP2538014B2/ja not_active Expired - Fee Related
- 1988-12-20 AU AU27068/88A patent/AU607834B2/en not_active Ceased
- 1988-12-20 NO NO885655A patent/NO172340C/no not_active IP Right Cessation
- 1988-12-20 IE IE379488A patent/IE63095B1/en not_active IP Right Cessation
- 1988-12-20 AT AT88870192T patent/ATE87206T1/de not_active IP Right Cessation
- 1988-12-20 DK DK198807081A patent/DK175113B1/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2538014B2 (ja) | 1996-09-25 |
| NO172340C (no) | 1993-07-07 |
| FI93210B (fi) | 1994-11-30 |
| FI93210C (fi) | 1995-03-10 |
| IE883794L (en) | 1989-06-21 |
| DK708188D0 (da) | 1988-12-20 |
| JPH01230517A (ja) | 1989-09-14 |
| PT89267B (pt) | 1993-12-31 |
| EP0322395A1 (fr) | 1989-06-28 |
| US4999360A (en) | 1991-03-12 |
| FI885880L (fi) | 1989-06-22 |
| NZ227410A (en) | 1991-06-25 |
| CA1316929C (fr) | 1993-04-27 |
| FI885880A0 (fi) | 1988-12-20 |
| NO172340B (no) | 1993-03-29 |
| KR910009994B1 (ko) | 1991-12-10 |
| AU607834B2 (en) | 1991-03-14 |
| IE63095B1 (en) | 1995-03-22 |
| IL88742A (en) | 1993-08-18 |
| DE3879653D1 (de) | 1993-04-29 |
| DE3879653T2 (de) | 1993-10-14 |
| PT89267A (pt) | 1989-12-29 |
| NO885655D0 (no) | 1988-12-20 |
| ATE87206T1 (de) | 1993-04-15 |
| AU2706888A (en) | 1989-06-22 |
| NO885655L (no) | 1989-06-22 |
| DK708188A (da) | 1989-06-22 |
| IL88742A0 (en) | 1989-07-31 |
| OA08937A (fr) | 1989-10-31 |
| EP0322395B1 (fr) | 1993-03-24 |
| KR890009389A (ko) | 1989-08-01 |
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