YU47878B - Postupak za dobijanje avermektina b i njihovih derivata - Google Patents
Postupak za dobijanje avermektina b i njihovih derivataInfo
- Publication number
- YU47878B YU47878B YU11988A YU11988A YU47878B YU 47878 B YU47878 B YU 47878B YU 11988 A YU11988 A YU 11988A YU 11988 A YU11988 A YU 11988A YU 47878 B YU47878 B YU 47878B
- Authority
- YU
- Yugoslavia
- Prior art keywords
- cooh
- alkyl
- group
- alpha
- avermectin
- Prior art date
Links
- 239000005660 Abamectin Substances 0.000 title abstract 4
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 abstract 1
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 101710088194 Dehydrogenase Proteins 0.000 abstract 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 abstract 1
- 229920002472 Starch Polymers 0.000 abstract 1
- 241001468227 Streptomyces avermitilis Species 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 238000010564 aerobic fermentation Methods 0.000 abstract 1
- OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 150000004716 alpha keto acids Chemical class 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000004132 cross linking Methods 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 230000001419 dependent effect Effects 0.000 abstract 1
- 238000000855 fermentation Methods 0.000 abstract 1
- 230000004151 fermentation Effects 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 235000019698 starch Nutrition 0.000 abstract 1
- 239000008107 starch Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/44—Preparation of O-glycosides, e.g. glucosides
- C12P19/60—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin
- C12P19/62—Preparation of O-glycosides, e.g. glucosides having an oxygen of the saccharide radical directly bound to a non-saccharide heterocyclic ring or a condensed ring system containing a non-saccharide heterocyclic ring, e.g. coumermycin, novobiocin the hetero ring having eight or more ring members and only oxygen as ring hetero atoms, e.g. erythromycin, spiramycin, nystatin
- C12P19/623—Avermectin; Milbemycin; Ivermectin; C-076
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/465—Streptomyces
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Microbiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Fodder In General (AREA)
- Enzymes And Modification Thereof (AREA)
- Steroid Compounds (AREA)
Abstract
POSTUPAK ZA DOBIJANJE AVERMEKTINA B I NJIHOVIH DERIVATA, formule u kojoj izlomljena linija na 22-23 polozaju predstavlja opcionu dvogubu vezu, R1 je hidroksi i prisutno je samo kada izostaje dvoguba veza, R2 je 4-(alfa-L-oleandrozil)-alfa-L-oleandroziloksi formule: R3 je vodonik, a R je alfa-racvasti C3-C8 alkil, C3-C8 alkenil, C3-C8 alkinil, C3-C8 alkoksialkil ili C3-C8 alkiltioalkil grupa, C5-C8 cik-loalkilalkil grupa, gde je alkil grupa jedna alfa razgranata C2-C5 alkil grupa, C3-C8 cikloalkil ili C5-C8 cikloalkenil grupa, pri cemu bilo koja od njih moze biti opciono supstituisana metilen grupom ili jednom ili vise C1-C4 alkil grupa ili halogenim atomima, ili 3- ili 6-clani heterociklicni prsten koji sadrzi kiseonik ili sumpor, koji moze biti zasicen ili potpuno ili parcijalno nezasicen i koji moze opciono biti supstituisan jednom ili vise C1-C4 alkil grupom ili halogen atomom, naznacen time, sto obuhvata aerobnu fermentaciju soja Streptomyces avermitilis ATCC 53692, kome nedostaje dehidrogenazna aktivnost za 2-okso kiselinu sa racvastim nizom i avermektin B-O-metiltransferazna aktivnost, na vodenoj podlozi koja sadrzi asimilirajuci izvor azota u kolicini do ko 5g(dm3 kao sto je kvasac, ugljenika u kolicini od oko 20-80g/dm3kao sto je skrob i neorganskih soli u kolicini od oko 0,001 do oko 7g/dm3 kao sto su soli Ca, Mg, Na, Fe, K ili Zn i jedinjenje sposobno za kroiscenje u biosintezi avermektina B formule: B-COOH ili jedinjenje koje se moze pretvoriti u pomenuto jedinjenje za vreme fermentacionog procesa formule R-(CH2)n-2 gde je R kao sto je prethodno definisano, n je 0, 2, 4 ili 6, a Z je -CH2OH, -CHO, -COOR4, CH2NH2 i CONHR5, gde je R4 H ili C1-C6 alkil, R5 je vodonik, C1-C4 alkil, -CH(COOH)CH2COOH, -CH(COOH) (CH2)2 COOH ili -CH(COOH) (CH2)2SCH3 na temperaturi od oko 24 do oko 33°C i priblizno neutralnoj pH vred-nosti. Prijava sadrzi jos 2 zavisna zahteva.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US651287A | 1987-01-23 | 1987-01-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| YU11988A YU11988A (en) | 1989-08-31 |
| YU47878B true YU47878B (sh) | 1996-05-20 |
Family
ID=21721247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU11988A YU47878B (sh) | 1987-01-23 | 1988-01-22 | Postupak za dobijanje avermektina b i njihovih derivata |
Country Status (30)
| Country | Link |
|---|---|
| EP (2) | EP0276103B1 (sh) |
| JP (2) | JPH0681757B2 (sh) |
| KR (2) | KR900004419B1 (sh) |
| CN (1) | CN1056883C (sh) |
| AR (1) | AR241798A1 (sh) |
| AT (2) | ATE96174T1 (sh) |
| AU (2) | AU595673B2 (sh) |
| BG (1) | BG51051A3 (sh) |
| BR (1) | BR8800271A (sh) |
| CZ (1) | CZ279782B6 (sh) |
| DD (2) | DD290214A5 (sh) |
| DE (2) | DE3884973T2 (sh) |
| DK (2) | DK28988A (sh) |
| EG (1) | EG18797A (sh) |
| ES (2) | ES2059498T3 (sh) |
| FI (2) | FI90091C (sh) |
| GR (1) | GR3007586T3 (sh) |
| HU (2) | HU201973B (sh) |
| IE (2) | IE61066B1 (sh) |
| IL (2) | IL85118A (sh) |
| IN (1) | IN167980B (sh) |
| MA (1) | MA21160A1 (sh) |
| MY (1) | MY103514A (sh) |
| NZ (2) | NZ223271A (sh) |
| PL (2) | PL156763B1 (sh) |
| PT (2) | PT86583B (sh) |
| RU (1) | RU1806198C (sh) |
| SK (1) | SK279351B6 (sh) |
| YU (1) | YU47878B (sh) |
| ZA (3) | ZA88448B (sh) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4806527A (en) * | 1987-03-16 | 1989-02-21 | Merck & Co., Inc. | Avermectin derivatives |
| US4874749A (en) * | 1987-07-31 | 1989-10-17 | Merck & Co., Inc. | 4"-Deoxy-4-N-methylamino avermectin Bla/Blb |
| EP0313297B1 (en) * | 1987-10-23 | 1993-05-19 | Pfizer Inc. | Process for production of avermectin aglycones and cultures therefor |
| GB8807280D0 (en) * | 1988-03-26 | 1988-04-27 | Pfizer Ltd | Antiparasitic agents |
| GB8811036D0 (en) * | 1988-05-10 | 1988-06-15 | Glaxo Group Ltd | Chemical compounds |
| GB8813760D0 (en) * | 1988-06-10 | 1988-07-13 | American Cyanamid Co | Chemical process |
| GB8815967D0 (en) * | 1988-07-05 | 1988-08-10 | Pfizer Ltd | Antiparasitic agents |
| NZ231772A (en) * | 1988-12-23 | 1992-11-25 | Merck & Co Inc | Avermectin derivatives, preparation and parasiticidal compositions thereof |
| NZ231773A (en) * | 1988-12-23 | 1992-09-25 | Merck & Co Inc | Avermectin derivatives, preparation and parasiticidal pharmaceutical compositions thereof |
| US5015630A (en) * | 1989-01-19 | 1991-05-14 | Merck & Co., Inc. | 5-oxime avermectin derivatives |
| US4897383A (en) * | 1989-02-13 | 1990-01-30 | Merck & Co., Inc. | Avermectin derivatives |
| US5252474A (en) * | 1989-03-31 | 1993-10-12 | Merck & Co., Inc. | Cloning genes from Streptomyces avermitilis for avermectin biosynthesis and the methods for their use |
| US5030622A (en) * | 1989-06-02 | 1991-07-09 | Merck & Co., Inc. | Avermectin derivatives |
| US5057499A (en) * | 1989-06-02 | 1991-10-15 | Merck & Co. Inc. | Avermectin derivatives |
| US5023241A (en) * | 1989-07-31 | 1991-06-11 | Merck & Co., Inc. | Avermectin derivatives |
| US5830875A (en) * | 1989-10-30 | 1998-11-03 | Merck & Co., Inc. | 24-and 25-substituted avermectin and milbemycin derivatives |
| JP2888586B2 (ja) * | 1990-03-05 | 1999-05-10 | 社団法人北里研究所 | エバーメクチンの特定成分を選択生産するための微生物およびその選択的製造法 |
| US5169839A (en) * | 1990-05-11 | 1992-12-08 | Merck & Co., Inc. | Derivatives of 3'- and 3"-o-desmethyl avermectin compounds, compositions and methods of treating melmintic and parasitic infections |
| US5208222A (en) * | 1991-03-28 | 1993-05-04 | Merck & Co., Inc. | 4"-and 4'-alkylthio avermectin derivatives |
| US5240915A (en) * | 1991-10-15 | 1993-08-31 | Merck & Co., Inc. | Avermectin derivatives |
| US6103504A (en) * | 1992-03-25 | 2000-08-15 | Pfizer Inc. | Process for production of avermectins and cultures therefor |
| US5292647A (en) * | 1992-11-30 | 1994-03-08 | Eli Lilly And Company | Strain of streptomyces for producing avermectins and processes therewith |
| CN1038330C (zh) * | 1993-07-05 | 1998-05-13 | 塞泰克斯公司 | 阿弗麦菌素的生产与分离 |
| EP0711349B1 (en) * | 1993-07-30 | 2003-09-03 | Pfizer Inc. | Genes encoding branched-chain alpha-ketoacid dehydrogenase complex from streptomyces avermitilis |
| JP2761296B2 (ja) * | 1993-10-05 | 1998-06-04 | フアイザー・インコーポレイテツド | ドラメクチンの製造方法および駆虫性中間体 |
| FI942725A (fi) * | 1993-12-16 | 1995-06-17 | Pfizer | Haaraketjuista alfaketohappodenydrogenaasikompleksia koodaavia geenejä Streptomyces avermitiliksesta |
| US5701591A (en) * | 1995-04-07 | 1997-12-23 | Telecommunications Equipment Corporation | Multi-function interactive communications system with circularly/elliptically polarized signal transmission and reception |
| CN1297485A (zh) * | 1998-02-13 | 2001-05-30 | 辉瑞产品公司 | 介导除虫菌素b2:b1比例的除虫链霉菌基因 |
| IL147563A0 (en) * | 1999-08-12 | 2002-08-14 | Pfizer Prod Inc | Streptomyces avermitilis gene directing the ratio of b2:b1 avermectins |
| KR100415395B1 (ko) * | 2000-08-02 | 2004-01-16 | 한국생명공학연구원 | 에버멕틴 ｂｃ-5-ｏ-메칠트랜스퍼라제의 유전자가 파괴된 스트렙토마이세스 에버미티리스 변이균주 및 그의 제조 방법 |
| ES2373629T3 (es) | 2002-02-12 | 2012-02-07 | Pfizer Products Inc. | Gen de streptomyces avemitilis que dirige la proporción de avermectinas b2:b1. |
| WO2023203038A1 (en) | 2022-04-19 | 2023-10-26 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE434277B (sv) | 1976-04-19 | 1984-07-16 | Merck & Co Inc | Sett att framstella nya antihelmintiskt verkande foreningar genom odling av streptomyces avermitilis |
| NZ188459A (en) * | 1977-10-03 | 1982-09-07 | Merck & Co Inc | Derivatives of c-076 compounds and pesticidal compositions |
| US4429042A (en) | 1978-09-08 | 1984-01-31 | Merck & Co., Inc. | Strain of Streptomyces for producing antiparasitic compounds |
| ES8800986A1 (es) * | 1985-07-27 | 1987-12-01 | Pfizer | Un procedimiento para la produccion de un nuevo derivado de avermectina |
| GB8606120D0 (en) * | 1986-03-12 | 1986-04-16 | Glaxo Group Ltd | Process |
-
1987
- 1987-12-10 IN IN1059/DEL/87A patent/IN167980B/en unknown
-
1988
- 1988-01-18 BG BG082657A patent/BG51051A3/xx unknown
- 1988-01-18 EP EP88300354A patent/EP0276103B1/en not_active Expired - Lifetime
- 1988-01-18 ES ES88300354T patent/ES2059498T3/es not_active Expired - Lifetime
- 1988-01-18 AT AT88300354T patent/ATE96174T1/de not_active IP Right Cessation
- 1988-01-18 IL IL85118A patent/IL85118A/xx not_active IP Right Cessation
- 1988-01-18 DE DE88300354T patent/DE3884973T2/de not_active Expired - Lifetime
- 1988-01-19 MA MA21397A patent/MA21160A1/fr unknown
- 1988-01-19 MY MYPI88000037A patent/MY103514A/en unknown
- 1988-01-20 ES ES88300426T patent/ES2053719T3/es not_active Expired - Lifetime
- 1988-01-20 AT AT88300426T patent/ATE87927T1/de not_active IP Right Cessation
- 1988-01-20 EP EP88300426A patent/EP0276131B1/en not_active Expired - Lifetime
- 1988-01-20 DE DE8888300426T patent/DE3879975T2/de not_active Expired - Lifetime
- 1988-01-21 SK SK407-88A patent/SK279351B6/sk unknown
- 1988-01-21 EG EG3588A patent/EG18797A/xx active
- 1988-01-21 PT PT86583A patent/PT86583B/pt unknown
- 1988-01-21 PT PT86584A patent/PT86584B/pt unknown
- 1988-01-21 PL PL1988270238A patent/PL156763B1/pl unknown
- 1988-01-21 CZ CS88407A patent/CZ279782B6/cs unknown
- 1988-01-21 PL PL1988270239A patent/PL156764B1/pl unknown
- 1988-01-21 IL IL85165A patent/IL85165A/xx not_active IP Right Cessation
- 1988-01-22 YU YU11988A patent/YU47878B/sh unknown
- 1988-01-22 ZA ZA88448A patent/ZA88448B/xx unknown
- 1988-01-22 CN CN88100649A patent/CN1056883C/zh not_active Expired - Lifetime
- 1988-01-22 IE IE16188A patent/IE61066B1/en not_active IP Right Cessation
- 1988-01-22 HU HU88260D patent/HU201973B/hu unknown
- 1988-01-22 FI FI880280A patent/FI90091C/fi not_active IP Right Cessation
- 1988-01-22 DD DD88312393A patent/DD290214A5/de unknown
- 1988-01-22 JP JP63012462A patent/JPH0681757B2/ja not_active Expired - Lifetime
- 1988-01-22 DK DK028988A patent/DK28988A/da not_active Application Discontinuation
- 1988-01-22 AR AR88309888A patent/AR241798A1/es active
- 1988-01-22 HU HU88261A patent/HU200487B/hu unknown
- 1988-01-22 ZA ZA88449A patent/ZA88449B/xx unknown
- 1988-01-22 ZA ZA88447A patent/ZA88447B/xx unknown
- 1988-01-22 DK DK198800290A patent/DK175720B1/da not_active IP Right Cessation
- 1988-01-22 IE IE16088A patent/IE61483B1/en not_active IP Right Cessation
- 1988-01-22 NZ NZ223271A patent/NZ223271A/en unknown
- 1988-01-22 DD DD88312394A patent/DD267512A5/de unknown
- 1988-01-22 NZ NZ223272A patent/NZ223272A/xx unknown
- 1988-01-22 FI FI880281A patent/FI90088C/fi not_active IP Right Cessation
- 1988-01-22 RU SU884355079A patent/RU1806198C/ru active
- 1988-01-22 AU AU10696/88A patent/AU595673B2/en not_active Expired
- 1988-01-22 KR KR1019880000470A patent/KR900004419B1/ko not_active IP Right Cessation
- 1988-01-23 KR KR1019880000506A patent/KR910002225B1/ko not_active IP Right Cessation
- 1988-01-23 JP JP63011881A patent/JPH0817693B2/ja not_active Expired - Lifetime
- 1988-01-25 BR BRPI8800271-3A patent/BR8800271A/pt not_active IP Right Cessation
-
1991
- 1991-02-15 AU AU71110/91A patent/AU631298B2/en not_active Expired
-
1993
- 1993-04-08 GR GR930400638T patent/GR3007586T3/el unknown
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