BG60531B2 - Специфични алкилиращи средства - Google Patents
Специфични алкилиращи средства Download PDFInfo
- Publication number
- BG60531B2 BG60531B2 BG098518A BG9851894A BG60531B2 BG 60531 B2 BG60531 B2 BG 60531B2 BG 098518 A BG098518 A BG 098518A BG 9851894 A BG9851894 A BG 9851894A BG 60531 B2 BG60531 B2 BG 60531B2
- Authority
- BG
- Bulgaria
- Prior art keywords
- carboxamido
- methyl
- pyrrole
- compound
- chloroethyl
- Prior art date
Links
- 230000000259 anti-tumor effect Effects 0.000 claims abstract description 7
- 230000000840 anti-viral effect Effects 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- GNFWGDKKNWGGJY-UHFFFAOYSA-N propanimidamide Chemical compound CCC(N)=N GNFWGDKKNWGGJY-UHFFFAOYSA-N 0.000 claims description 8
- 239000013543 active substance Substances 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000005518 carboxamido group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 claims 1
- 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 class 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 claims 1
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 claims 1
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract 1
- UPBAOYRENQEPJO-UHFFFAOYSA-N n-[5-[[5-[(3-amino-3-iminopropyl)carbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-4-formamido-1-methylpyrrole-2-carboxamide Chemical class CN1C=C(NC=O)C=C1C(=O)NC1=CN(C)C(C(=O)NC2=CN(C)C(C(=O)NCCC(N)=N)=C2)=C1 UPBAOYRENQEPJO-UHFFFAOYSA-N 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
- 239000000203 mixture Substances 0.000 description 22
- -1 hydroxy, aziridinyl Chemical group 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
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- 210000004027 cell Anatomy 0.000 description 12
- 229910052736 halogen Inorganic materials 0.000 description 12
- 150000002367 halogens Chemical class 0.000 description 12
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- 238000006243 chemical reaction Methods 0.000 description 9
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- 239000001257 hydrogen Substances 0.000 description 8
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- 125000003545 alkoxy group Chemical group 0.000 description 6
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- 229920002261 Corn starch Polymers 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 206010039491 Sarcoma Diseases 0.000 description 4
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- 238000004587 chromatography analysis Methods 0.000 description 4
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- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
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- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
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- 108020004707 nucleic acids Proteins 0.000 description 1
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- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- GLQWRXYOTXRDNH-UHFFFAOYSA-N thiophen-2-amine Chemical compound NC1=CC=CS1 GLQWRXYOTXRDNH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/34—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 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Peptides Or Proteins (AREA)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB868612218A GB8612218D0 (en) | 1986-05-20 | 1986-05-20 | Site specific alkylating agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG60531B2 true BG60531B2 (bg) | 1995-07-28 |
Family
ID=10598117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG098518A BG60531B2 (bg) | 1986-05-20 | 1994-02-22 | Специфични алкилиращи средства |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US5017599A (fi) |
| EP (1) | EP0246868B1 (fi) |
| JP (1) | JPH0623193B2 (fi) |
| KR (1) | KR950011408B1 (fi) |
| AT (1) | ATE80617T1 (fi) |
| AU (1) | AU597659B2 (fi) |
| BG (1) | BG60531B2 (fi) |
| BR (1) | BR1101017A (fi) |
| CA (1) | CA1314551C (fi) |
| CS (1) | CS413791A3 (fi) |
| DE (1) | DE3781716T2 (fi) |
| DK (1) | DK254587A (fi) |
| ES (1) | ES2046202T3 (fi) |
| FI (1) | FI86543C (fi) |
| GB (1) | GB8612218D0 (fi) |
| GR (1) | GR3006163T3 (fi) |
| HK (1) | HK31993A (fi) |
| HU (1) | HU201336B (fi) |
| IE (1) | IE60198B1 (fi) |
| IL (1) | IL82553A (fi) |
| MX (1) | MX9203122A (fi) |
| NZ (1) | NZ220361A (fi) |
| PT (1) | PT84896B (fi) |
| SG (1) | SG3793G (fi) |
| SU (1) | SU1528316A3 (fi) |
| UA (1) | UA5928A1 (fi) |
| ZA (1) | ZA873593B (fi) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN85103908A (zh) * | 1985-07-16 | 1986-11-05 | 法米塔利·卡洛·埃尔巴有限公司 | 制备4′-表多克索红菌素的新方法 |
| GB8906709D0 (en) * | 1989-03-23 | 1989-05-10 | Creighton Andrew M | Acryloyl substituted pyrrole derivatives |
| IT1262921B (it) * | 1992-01-10 | 1996-07-22 | Federico Arcamone | Agenti antitumorali analoghi di oligopeptidi pirrol-amidinici retroversi processi di preparazione e prodotti farmaceutici che li contengono |
| IT1271456B (it) * | 1993-03-01 | 1997-05-28 | Menarini Farma Ind | Composti pirrol-amidinici, e loro sali farmaceuticamente accettabili, processi di preparazione e composizioni farmaceutiche che li contengono |
| GB9416005D0 (en) * | 1994-08-08 | 1994-09-28 | Erba Carlo Spa | Peptidic compounds analogous to distamycin a and process for their preparation |
| US5821258A (en) * | 1994-12-27 | 1998-10-13 | Mitsui Chemicals, Inc. | Phenylbenzimidazole derivatives |
| CA2180206A1 (en) * | 1995-06-30 | 1996-12-31 | Motoya Ohshika | Freeze-dried preparation for pharmaceutical use |
| GB9514993D0 (en) * | 1995-07-21 | 1995-09-20 | Pharmacia Spa | Site specific phenyl nitrogen mustards |
| US5808087A (en) * | 1995-11-29 | 1998-09-15 | Mitsui Chemicals, Inc. | Sulfonium salts of pyrrolylbenzimidazoles |
| AU1596097A (en) * | 1996-02-02 | 1997-08-22 | Pharmacia & Upjohn S.P.A. | Distamycin derivatives, process for preparing them, and their use as antitumor and antiviral agents |
| US6506906B1 (en) | 1996-02-26 | 2003-01-14 | California Institute Of Technology | Preparation and use of bifunctional molecules having DNA sequence binding specificity |
| US6090947A (en) | 1996-02-26 | 2000-07-18 | California Institute Of Technology | Method for the synthesis of pyrrole and imidazole carboxamides on a solid support |
| JP2001513759A (ja) | 1996-02-26 | 2001-09-04 | カリフォルニア・インスティチュート・オブ・テクノロジー | 二本鎖ｄｎａの副溝において結合する改良されたポリアミド |
| US6555692B1 (en) | 1996-02-26 | 2003-04-29 | California Institute Of Technology | Preparation and use of bifunctional molecules having DNA sequence binding specificity |
| US6635417B1 (en) | 1996-07-31 | 2003-10-21 | California Institute Of Technology | Complex formation between DSDNA and oligomer of cyclic heterocycles |
| EP1023288A1 (en) | 1996-02-26 | 2000-08-02 | California Institute Of Technology | Stereochemical control of the dna binding affinity, sequence specificity, and orientation-preference of chiral hairpin polyamides in the minor groove |
| US6143901A (en) * | 1996-07-31 | 2000-11-07 | Genesoft, Inc. | Complex formation between dsDNA and pyrrole imidazole polyamides |
| GB9610079D0 (en) * | 1996-05-14 | 1996-07-17 | Pharmacia Spa | Distamycin deriratives process for preparing them and their use as antitumor and antiviral agents |
| GB9615692D0 (en) * | 1996-07-25 | 1996-09-04 | Pharmacia Spa | Acryloyl substituted distamycin derivatives, process for preparing them, and their use as antitumor and antiviral agents |
| US5998140A (en) * | 1996-07-31 | 1999-12-07 | The Scripps Research Institute | Complex formation between dsDNA and oligomer of cyclic heterocycles |
| GB9623522D0 (en) * | 1996-11-11 | 1997-01-08 | Pharmacia & Upjohn Spa | Benzoheterocycle distamycin derivatives process for preparing them and their use as antitumour and antiviral agents |
| US20040072889A1 (en) * | 1997-04-21 | 2004-04-15 | Pharmacia Corporation | Method of using a COX-2 inhibitor and an alkylating-type antineoplastic agent as a combination therapy in the treatment of neoplasia |
| GB9806692D0 (en) * | 1998-03-27 | 1998-05-27 | Pharmacia & Upjohn Spa | Benzoheterocyclic distamycin derivatives, process for preparing them and their use as antitumour agents |
| GB9816652D0 (en) * | 1998-07-30 | 1998-09-30 | Pharmacia & Upjohn Spa | Sulfurated distamycin derivatives process for preparing them and their use as antitumor agents |
| GB9816653D0 (en) * | 1998-07-30 | 1998-09-30 | Pharmacia & Upjohn Spa | Oxidised sulfurated distamycin derivatives process for preparing them and their use as antitumor agents |
| KR20010063274A (ko) * | 1999-12-22 | 2001-07-09 | 성재갑 | 〔1-｛〔1-（1,3-벤조디옥솔-5-일메틸-1ｈ-이미다졸-5-일〕메틸｝-4-(1-나프틸)-1ｈ-피롤-3-일〕（4-메틸-1-피페라지닐）메타논의 약학적 조성물 |
| US6559125B1 (en) | 2000-01-28 | 2003-05-06 | California Institute Of Technology | Polyamide-alkylator conjugates and related products and method |
| US7078536B2 (en) * | 2001-03-14 | 2006-07-18 | Genesoft Pharmaceuticals, Inc. | Charged compounds comprising a nucleic acid binding moiety and uses therefor |
| CA2403537A1 (en) * | 2000-03-16 | 2001-10-11 | Genesoft, Inc. | Charged compounds comprising a nucleic acid binding moiety and uses therefor |
| GB0011059D0 (en) | 2000-05-08 | 2000-06-28 | Pharmacia & Upjohn Spa | Use of substituted acryloyl distamycin derivatives in the treatment of tumours associated with high levels of glutathione |
| GB0015446D0 (en) | 2000-06-23 | 2000-08-16 | Pharmacia & Upjohn Spa | Combined therapy against tumors comprising substituted acryloyl distamycin derivates,taxanes and/or antimetabolites |
| GB0015447D0 (en) * | 2000-06-23 | 2000-08-16 | Pharmacia & Upjohn Spa | Combined therapy against tumors comprising substituted acryloyl derivates and alkylating agents |
| GB0016447D0 (en) | 2000-07-04 | 2000-08-23 | Pharmacia & Upjohn Spa | Process for preparing distamycin derivatives |
| GB0029004D0 (en) | 2000-11-28 | 2001-01-10 | Pharmacia & Upjohn Spa | Process for preparing distamycin derivatives |
| WO2002088119A1 (en) * | 2001-04-26 | 2002-11-07 | Genesoft Pharmaceuticals, Inc | Halogen-substituted thienyl compounds |
| US6969592B2 (en) | 2001-09-26 | 2005-11-29 | Pharmacia Italia S.P.A. | Method for predicting the sensitivity to chemotherapy |
| EP1539151B1 (en) | 2002-08-02 | 2009-03-18 | Genesoft Pharmaceuticals, Inc. | Biaryl compounds having anti-infective activity |
| WO2004039318A2 (en) * | 2002-10-25 | 2004-05-13 | Genesoft Pharmaceuticals, Inc. | Anti-infective biaryl compounds |
| EP1587529A4 (en) | 2002-12-10 | 2009-08-12 | Oscient Pharmaceuticals Corp | ANTIBACTERIAL COMPOUNDS HAVING A PATTERN (CARBOXAMIDE PYRROLE) - (BENZAMIDE) - (IMIDAZOLE CARBOXAMIDE) |
| GB202114032D0 (en) * | 2021-09-30 | 2021-11-17 | Univ Strathclyde | Antivirals |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR86210E (fi) * | 1963-04-04 | 1966-03-23 | ||
| BR6461040D0 (pt) * | 1963-07-26 | 1973-08-02 | Farmaceutici Italia | Processo para preparar novos derivados de pirrol |
| DE1795539A1 (de) * | 1963-07-26 | 1972-01-13 | Farmaceutici Italia | Verfahren zur Herstellung von neuen Pyrrolderivaten und ihren Salzen |
| FR141F (fi) * | 1963-07-26 | |||
| NL130086C (fi) * | 1964-07-14 | 1970-06-15 | ||
| CN85103908A (zh) * | 1985-07-16 | 1986-11-05 | 法米塔利·卡洛·埃尔巴有限公司 | 制备4′-表多克索红菌素的新方法 |
| GB8517922D0 (en) * | 1985-07-16 | 1985-08-21 | Erba Farmitalia | Carboxamido derivatives |
-
1986
- 1986-05-20 GB GB868612218A patent/GB8612218D0/en active Pending
-
1987
- 1987-05-14 HU HU872168A patent/HU201336B/hu not_active IP Right Cessation
- 1987-05-18 FI FI872173A patent/FI86543C/fi not_active IP Right Cessation
- 1987-05-18 AU AU73163/87A patent/AU597659B2/en not_active Ceased
- 1987-05-18 IE IE129287A patent/IE60198B1/en not_active IP Right Cessation
- 1987-05-18 UA UA4202591A patent/UA5928A1/uk unknown
- 1987-05-18 IL IL82553A patent/IL82553A/xx unknown
- 1987-05-18 SU SU874202591A patent/SU1528316A3/ru active
- 1987-05-19 JP JP62122375A patent/JPH0623193B2/ja not_active Expired - Lifetime
- 1987-05-19 AT AT87304442T patent/ATE80617T1/de not_active IP Right Cessation
- 1987-05-19 PT PT84896A patent/PT84896B/pt not_active IP Right Cessation
- 1987-05-19 KR KR1019870004929A patent/KR950011408B1/ko not_active IP Right Cessation
- 1987-05-19 DE DE8787304442T patent/DE3781716T2/de not_active Expired - Fee Related
- 1987-05-19 DK DK254587A patent/DK254587A/da not_active Application Discontinuation
- 1987-05-19 EP EP87304442A patent/EP0246868B1/en not_active Expired - Lifetime
- 1987-05-19 CA CA000537338A patent/CA1314551C/en not_active Expired - Fee Related
- 1987-05-19 ES ES198787304442T patent/ES2046202T3/es not_active Expired - Lifetime
- 1987-05-19 ZA ZA873593A patent/ZA873593B/xx unknown
- 1987-05-19 NZ NZ220361A patent/NZ220361A/en unknown
-
1990
- 1990-02-21 US US07/485,847 patent/US5017599A/en not_active Expired - Fee Related
-
1991
- 1991-12-30 CS CS914137A patent/CS413791A3/cs unknown
-
1992
- 1992-06-22 MX MX9203122A patent/MX9203122A/es unknown
- 1992-11-05 GR GR920402483T patent/GR3006163T3/el unknown
-
1993
- 1993-01-08 SG SG37/93A patent/SG3793G/en unknown
- 1993-04-01 HK HK319/93A patent/HK31993A/xx not_active IP Right Cessation
-
1994
- 1994-02-22 BG BG098518A patent/BG60531B2/bg unknown
-
1997
- 1997-05-14 BR BR1101017-7A patent/BR1101017A/pt active IP Right Grant
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