PT100357B - Compostos lactama macrociclicos, seu processo de preparacao e intermediarios, e composicoes que os contem - Google Patents
Compostos lactama macrociclicos, seu processo de preparacao e intermediarios, e composicoes que os contem Download PDFInfo
- Publication number
- PT100357B PT100357B PT100357A PT10035792A PT100357B PT 100357 B PT100357 B PT 100357B PT 100357 A PT100357 A PT 100357A PT 10035792 A PT10035792 A PT 10035792A PT 100357 B PT100357 B PT 100357B
- Authority
- PT
- Portugal
- Prior art keywords
- oxy
- methyl
- tridesoxy
- ribohexopyranosyl
- ethyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 143
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000000203 mixture Substances 0.000 title abstract description 56
- -1 lactam compounds Chemical class 0.000 claims abstract description 105
- 238000000034 method Methods 0.000 claims abstract description 26
- 230000008569 process Effects 0.000 claims abstract description 13
- QIVRQFJRUABARQ-UHFFFAOYSA-N pentadec-14-en-7-one Chemical compound CCCCCCC(=O)CCCCCCC=C QIVRQFJRUABARQ-UHFFFAOYSA-N 0.000 claims description 66
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 58
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 36
- QBEKGNIWIHIMOM-UHFFFAOYSA-N tridec-12-en-5-one Chemical compound CCCCC(=O)CCCCCCC=C QBEKGNIWIHIMOM-UHFFFAOYSA-N 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 229960003276 erythromycin Drugs 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 15
- 150000002118 epoxides Chemical class 0.000 claims description 11
- 150000003951 lactams Chemical class 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000001589 carboacyl group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 210000000813 small intestine Anatomy 0.000 claims description 6
- JFVYXJKGJMUGRG-KJPZRSJGSA-N Erythromycin a enol ether Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C2=C(C)C[C@](O2)(C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 JFVYXJKGJMUGRG-KJPZRSJGSA-N 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 150000005676 cyclic carbonates Chemical class 0.000 claims description 5
- 230000005176 gastrointestinal motility Effects 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 5
- VUXXXYMMZBAUSE-UHFFFAOYSA-N pentadecan-7-one Chemical compound CCCCCCCCC(=O)CCCCCC VUXXXYMMZBAUSE-UHFFFAOYSA-N 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- GBCKRQRXNXQQPW-UHFFFAOYSA-N n,n-dimethylprop-2-en-1-amine Chemical compound CN(C)CC=C GBCKRQRXNXQQPW-UHFFFAOYSA-N 0.000 claims description 4
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 241000282412 Homo Species 0.000 claims description 2
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- 230000002269 spontaneous effect Effects 0.000 claims description 2
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- 239000000243 solution Substances 0.000 description 116
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 108
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 60
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- 239000011541 reaction mixture Substances 0.000 description 46
- 239000000047 product Substances 0.000 description 36
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
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- 239000012267 brine Substances 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
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- 239000012074 organic phase Substances 0.000 description 17
- 230000002829 reductive effect Effects 0.000 description 17
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
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- 239000003054 catalyst Substances 0.000 description 13
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- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
- 229910021529 ammonia Inorganic materials 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 229930006677 Erythromycin A Natural products 0.000 description 11
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
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- 239000000463 material Substances 0.000 description 9
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 9
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
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- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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- 231100000673 dose–response relationship Toxicity 0.000 description 6
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- 150000001350 alkyl halides Chemical class 0.000 description 5
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- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
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- IDRYSCOQVVUBIJ-UHFFFAOYSA-N Erythromycin-B Natural products CC1C(OC2C(C(CC(C)O2)N(C)C)O)C(C)(O)CC(C)C(=O)C(C)C(O)C(C)C(CC)OC(=O)C(C)C1OC1CC(C)(OC)C(O)C(C)O1 IDRYSCOQVVUBIJ-UHFFFAOYSA-N 0.000 description 4
- MWFRKHPRXPSWNT-UHFFFAOYSA-N Erythromycin-C Natural products CC1C(OC2C(C(CC(C)O2)N(C)C)O)C(C)(O)CC(C)C(=O)C(C)C(O)C(O)(C)C(CC)OC(=O)C(C)C1OC1CC(C)(O)C(O)C(C)O1 MWFRKHPRXPSWNT-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- 206010021518 Impaired gastric emptying Diseases 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
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- 238000000576 coating method Methods 0.000 description 3
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 3
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- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 210000002438 upper gastrointestinal tract Anatomy 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 210000002417 xiphoid bone Anatomy 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
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)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Polyamides (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hydrogenated Pyridines (AREA)
- Cephalosporin Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68283691A | 1991-04-09 | 1991-04-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT100357A PT100357A (pt) | 1993-07-30 |
| PT100357B true PT100357B (pt) | 1999-06-30 |
Family
ID=24741372
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT100357A PT100357B (pt) | 1991-04-09 | 1992-04-08 | Compostos lactama macrociclicos, seu processo de preparacao e intermediarios, e composicoes que os contem |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5538961A (Sortimente) |
| EP (1) | EP0579770B1 (Sortimente) |
| JP (1) | JPH06509326A (Sortimente) |
| KR (1) | KR100222014B1 (Sortimente) |
| AT (1) | ATE139697T1 (Sortimente) |
| AU (1) | AU663089B2 (Sortimente) |
| CA (1) | CA2103913A1 (Sortimente) |
| DE (1) | DE69211845T2 (Sortimente) |
| DK (1) | DK0579770T3 (Sortimente) |
| ES (1) | ES2091471T3 (Sortimente) |
| GR (1) | GR3020853T3 (Sortimente) |
| IE (1) | IE73236B1 (Sortimente) |
| IL (1) | IL101504A (Sortimente) |
| PT (1) | PT100357B (Sortimente) |
| WO (1) | WO1992018134A1 (Sortimente) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1122261A3 (en) * | 2000-01-31 | 2001-09-26 | Pfizer Products Inc. | 13 and 14-membered antibacterial macrolides |
| AU2001238476A1 (en) | 2000-02-18 | 2001-08-27 | Kosan Biosciences, Inc. | Motocide compounds |
| AU2000265939A1 (en) | 2000-08-17 | 2002-02-25 | The Kitasato Institute | Novel pseudoerythromycin derivatives |
| JP2004522726A (ja) * | 2000-12-01 | 2004-07-29 | コーサン バイオサイエンシーズ， インコーポレイテッド | モチリド化合物 |
| US20020094962A1 (en) * | 2000-12-01 | 2002-07-18 | Gary Ashley | Motilide compounds |
| ATE417856T1 (de) * | 2002-08-29 | 2009-01-15 | Pfizer | Motilidverbindungen |
| EP1536841A1 (en) * | 2002-09-12 | 2005-06-08 | The University of Chicago | Monitoring and diagnosis of gastric emptying and gastroparesis |
| DE602004025569D1 (de) | 2003-06-18 | 2010-04-01 | Tranzyme Pharma Inc | Makrozyklische motilin rezeptorantagonisten |
| US7407941B2 (en) * | 2003-08-26 | 2008-08-05 | Pfizer, Inc. | N-desmethyl-N-substituted-11-deoxyerythromycin compounds |
| US20050113319A1 (en) * | 2003-08-26 | 2005-05-26 | Christopher Carreras | 11-Deoxy-6,9-ether erythromycin compounds |
| US7211568B2 (en) * | 2003-12-18 | 2007-05-01 | Kosan Biosciences Incorporated | 9-Desoxoerythromycin compounds as prokinetic agents |
| US7582611B2 (en) | 2005-05-24 | 2009-09-01 | Pfizer Inc. | Motilide compounds |
| BRPI0619556A2 (pt) * | 2005-12-08 | 2011-10-04 | Pfizer | processo para desmetilação de grupo 3' -dimetil amino de compostos eritromicina |
| JP5684474B2 (ja) | 2006-09-11 | 2015-03-11 | オセラ セラピューティクス， インコーポレイテッド | 胃腸の運動障害疾患の治療のためのモチリン受容体の大環状アンタゴニスト |
| ES2401467T3 (es) | 2006-12-05 | 2013-04-19 | Bristol-Myers Squibb Company | Polimorfos de motilida |
| US20080287371A1 (en) * | 2007-05-17 | 2008-11-20 | Tranzyme Pharma Inc. | Macrocyclic antagonists of the motilin receptor for modulation of the migrating motor complex |
| CA2843221A1 (en) * | 2011-07-29 | 2013-02-07 | Michael John Booth | Methods for detection of nucleotide modification |
| EP3351644B1 (en) | 2012-11-30 | 2020-01-29 | Cambridge Epigenetix Limited | Oxidising agent for modified nucleotides |
| CN115057794B (zh) * | 2022-07-07 | 2023-11-17 | 桂林理工大学 | 一种可见光诱导铈催化氧化酰胺去甲基化的方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4512982A (en) * | 1984-04-13 | 1985-04-23 | Pfizer Inc. | 9α-Aza-9α-homoerythromycin compounds, pharmaceutical composition and therapeutic method |
| US4518590A (en) * | 1984-04-13 | 1985-05-21 | Pfizer Inc. | 9α-Aza-9α-homoerythromycin compounds, pharmaceutical compositions and therapeutic method |
| DE3689758T2 (de) * | 1985-08-31 | 1994-08-18 | Kitasato Inst | Erythromycinderivat und Verfahren zu dessen Herstellung. |
| US5008249A (en) * | 1985-08-31 | 1991-04-16 | Kitasato Kenkyusho | Therapeutic method of stimulating digestive tract contractile motion in mammals |
| US5106961A (en) * | 1987-05-26 | 1992-04-21 | Eli Lilly And Company | Erythromycin ring-contracted derivatives |
| US4958010A (en) * | 1988-02-16 | 1990-09-18 | Bristol-Myers Company | Epipodophyllotoxin glucoside lactam derivatives |
| US4920102A (en) * | 1988-04-18 | 1990-04-24 | Eli Lilly And Company | Method for treating gastrointestinal disorders |
| US5202434A (en) * | 1991-04-05 | 1993-04-13 | Merck & Co., Inc. | 8a-aza-8a-homoerythromycin lactams |
| US5189159A (en) * | 1992-04-02 | 1993-02-23 | Merck & Co., Inc. | 8a-AZA-8a-homoerythromycin cyclic iminoethers |
-
1992
- 1992-03-30 US US08/108,659 patent/US5538961A/en not_active Expired - Fee Related
- 1992-03-30 CA CA002103913A patent/CA2103913A1/en not_active Abandoned
- 1992-03-30 EP EP92911585A patent/EP0579770B1/en not_active Expired - Lifetime
- 1992-03-30 AU AU19103/92A patent/AU663089B2/en not_active Ceased
- 1992-03-30 KR KR1019930703026A patent/KR100222014B1/ko not_active Expired - Fee Related
- 1992-03-30 AT AT92911585T patent/ATE139697T1/de not_active IP Right Cessation
- 1992-03-30 WO PCT/US1992/002590 patent/WO1992018134A1/en not_active Ceased
- 1992-03-30 JP JP4511370A patent/JPH06509326A/ja active Pending
- 1992-03-30 DE DE69211845T patent/DE69211845T2/de not_active Expired - Fee Related
- 1992-03-30 ES ES92911585T patent/ES2091471T3/es not_active Expired - Lifetime
- 1992-03-30 DK DK92911585.5T patent/DK0579770T3/da active
- 1992-04-02 IE IE921045A patent/IE73236B1/en not_active IP Right Cessation
- 1992-04-06 IL IL101504A patent/IL101504A/en not_active IP Right Cessation
- 1992-04-08 PT PT100357A patent/PT100357B/pt not_active IP Right Cessation
-
1996
- 1996-08-22 GR GR960402210T patent/GR3020853T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE139697T1 (de) | 1996-07-15 |
| CA2103913A1 (en) | 1992-10-10 |
| US5538961A (en) | 1996-07-23 |
| WO1992018134A1 (en) | 1992-10-29 |
| DK0579770T3 (da) | 1996-11-04 |
| DE69211845D1 (de) | 1996-08-01 |
| JPH06509326A (ja) | 1994-10-20 |
| EP0579770B1 (en) | 1996-06-26 |
| GR3020853T3 (en) | 1996-11-30 |
| EP0579770A1 (en) | 1994-01-26 |
| ES2091471T3 (es) | 1996-11-01 |
| AU1910392A (en) | 1992-11-17 |
| AU663089B2 (en) | 1995-09-28 |
| IE921045A1 (en) | 1992-10-21 |
| IL101504A0 (en) | 1992-12-30 |
| IL101504A (en) | 1998-04-05 |
| PT100357A (pt) | 1993-07-30 |
| IE73236B1 (en) | 1997-05-21 |
| DE69211845T2 (de) | 1997-01-23 |
| KR100222014B1 (ko) | 1999-10-01 |
| EP0579770A4 (Sortimente) | 1994-03-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB1A | Laying open of patent application |
Effective date: 19930317 |
|
| FG3A | Patent granted, date of granting |
Effective date: 19990331 |
|
| MM3A | Annulment or lapse |
Free format text: LAPSE DUE TO NON-PAYMENT OF FEES Effective date: 20030930 |