IL70232A0 - 6-(hydroxy-lower alkyl)-penem compounds,their manufacture and pharmaceutical compositions containing them - Google Patents
6-(hydroxy-lower alkyl)-penem compounds,their manufacture and pharmaceutical compositions containing themInfo
- Publication number
- IL70232A0 IL70232A0 IL70232A IL7023283A IL70232A0 IL 70232 A0 IL70232 A0 IL 70232A0 IL 70232 A IL70232 A IL 70232A IL 7023283 A IL7023283 A IL 7023283A IL 70232 A0 IL70232 A0 IL 70232A0
- Authority
- IL
- Israel
- Prior art keywords
- lower alkyl
- hydroxy
- carboxy
- radical
- formula
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 title abstract 17
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 10
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 6
- 150000003839 salts Chemical class 0.000 abstract 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 125000003282 alkyl amino group Chemical group 0.000 abstract 4
- 125000000524 functional group Chemical group 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- -1 lower alkalnoylamino Chemical group 0.000 abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 4
- 230000003287 optical effect Effects 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 3
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 125000005237 alkyleneamino group Chemical group 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000000753 cycloalkyl 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000002950 monocyclic group Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000000369 oxido group Chemical group [*]=O 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 2
- 230000004962 physiological condition Effects 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- 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
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/88—Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/568—Four-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Indole Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
1. Claims (for the Contracting States : BE, CH, LI, DE, FR, GB, IT, LU, NL, SE) 2-heterocyclyl-lower alkyl-6-hydroxy-lower alkyl-2-penem compounds of the formula see diagramm : EP0110826,P37,F1 in which R1 represents hydrogen or methyl, R2 represents hydroxy or protected hydroxy, R3 represents carboxy or protected carboxy R'3 , especially esterified carboxy R'3 that can be cleaved under physiological conditions, R4 represents a monocyclic, optionally partially saturated 5-membered heteroaryl radical that has from 1 to 4 ring nitrogen atoms and is bonded via a tertiary ring nitrogen atom to the radical -(CH2 )m - or a corresponding partially saturated 6-membered heteroaryl radical having from 1 to 3 ring nitrogen atoms, these radicals being unsubstituted or substituted by hydroxy, lower alkoxy, lower alkanoyloxy, halogen, mercapto, lower alkylthio, phenylthio, lower alkyl, hydroxy-lower alkyl, lower alkoxy-lower alkyl, carboxy-lower alkyl, amino-lower alkyl, di-lower alkylamino-lower alkyl, sulpho-lower alkyl, amino, lower alkylamino, di-lower alkylamino, lower alkyleneamino, lower alkalnoylamino, carboxy, lower alkoxycarbonyl, optionally N-mono- or N,N-di-lower alkylated carbamoyl, cyano, sulpho, sulphamoyl, phenyl that is optionally substituted by lower alkyl, nitro, lower alkoxy and/or by halogen, cycloalkyl, nitro, oxo and/or oxido, the radicals designated "lower" containing up to 7 carbon atoms, and m represents an integer from 1 to 4, salts of compounds of the formula I that have a salt-forming group, optical isomers of compounds of the formula I and mixtures of these optical isomers. 1. Claims (for the Contracting State AT) Process for the manufacture of compounds of the formula see diagramm : EP0110826,P40,F1 in which R1 represents hydrogen or methyl, R2 represents hydroxy or protected hydroxy, R3 represents carboxy or protected carboxy R'3 , especially esterified carboxy R'3 that can be cleaved under physiological conditions, R4 represents a mono-cyclic, optionally partially saturated 5-membered heteroaryl radical that has from 1 to 4 ring nitrogen atoms and is bonded via a tertiary ring nitrogen atom to the radical -(CH2 )m - or a corresponding partially saturated 6-membered heteroaryl radical having from 1 to 3 ring nitrogen atoms, these radicals being unsubstituted or substituted by hydroxy, lower alkoxy, lower alkanoyloxy, halogen, mercapto, lower alkylthio, phenylthio, lower alkyl, hydroxy-lower alkyl, lower alkoxy-lower alkyl, carboxy-lower alkyl, amino-lower alkyl, di-lower alkylamino-lower alkyl, sulpho-lower alkyl, amino, lower alkylamino, di-lower alkylamino, lower alkyleneamino, lower alkanoylamino, carboxy, lower alkoxycarbonyl, optionally N-mono- or N,N-di-lower alkylated carbamoyl, cyano, sulpho, sulphamoyl, phenyl that is optionally substituted by lower alkyl, nitro, lower alkoxy and/or by halogen, cycloalkyl, nitro, oxo and/or oxido, the radicals designated "lower" containing up to 7 carbon atoms, and m represents an integer form 1 to 4, their salts, their optical isomers and mixtures of their optical isomers, characterised in that a) an ylide compound of the formula see diagramm : EP0110826,P40,F2 in which R1 , R2 , R'3 , R4 and m have the meanings given under formula I, a hydroxy group R2 and any functional groups which may additionally be present in the radical R4 preferably being in protected form, Z represents oxygen or sulphur and X (anion) represents either a trisubstituted phosphonio group or a diesterified phosphono group together with a cation, is cyclised, or b) a compound of the formula see diagramm : EP0110826,P40,F3 in which R1 , R2 , R'3 , R4 and m have the meanings given under formula I, a hydroxy group R2 and any functional groups which may additionally be present in the radical R4 preferably being in protected form, is treated with an organic compound of trivalent phosphorus, or c) a compound of the formula see diagramm : EP0110826,P40,F4 in which R1 , R2 , R'3 and m have the meanings given above, and Q represents a reactive esterified hydroxy group, is reacted with an agent that introduces the azaheterocyclyl radical R4 , and, if desired or necessary, in a resulting compound of the formula I a protected hydroxy group R2 is converted into a free hydroxy group, and/or, if desired, in a resulting compound of the formula I a protected carboxy group R'3 is converted into the free carboxy group R'3 , and/or, if desired, other protected functional groups present in the radical R4 are converted into the free functional groups, and/or, if desired, a resulting compound of the formula I a radical R4 is converted into a different radical R4 , and/or, if desired, a resulting compound having a salt-forming group is converted into a salt, or a resulting salt is converted into the free compound or into a different salt, and/or, if desired, a resulting mixture of isomeric compounds is separated into the individual isomers.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH667082 | 1982-11-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL70232A0 true IL70232A0 (en) | 1984-02-29 |
| IL70232A IL70232A (en) | 1988-03-31 |
Family
ID=4313181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL70232A IL70232A (en) | 1982-11-16 | 1983-11-14 | 6-(hydroxy-lower alkyl)-penem compounds,their manufacture and pharmaceutical compositions containing them |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0110826B1 (en) |
| JP (1) | JPS59101492A (en) |
| KR (1) | KR840006665A (en) |
| AT (1) | ATE29031T1 (en) |
| AU (1) | AU569264B2 (en) |
| DD (1) | DD215551A5 (en) |
| DE (1) | DE3373098D1 (en) |
| DK (1) | DK522783A (en) |
| ES (2) | ES8605525A1 (en) |
| FI (1) | FI76348C (en) |
| GR (1) | GR79072B (en) |
| HU (1) | HU192827B (en) |
| IE (1) | IE56236B1 (en) |
| IL (1) | IL70232A (en) |
| NO (1) | NO834189L (en) |
| NZ (1) | NZ206278A (en) |
| PH (1) | PH21930A (en) |
| PT (1) | PT77658B (en) |
| ZA (1) | ZA838462B (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4794109A (en) * | 1982-11-16 | 1988-12-27 | Ciba-Geigy Corporation | 6-hydroxy-lower alkylpenem compounds, pharmaceutical preparations that contain these compounds, and the use of the latter |
| DK613984A (en) * | 1983-12-30 | 1985-07-01 | Ciba Geigy Ag | 2-HETEROCYCLYL-6-HYDROXYLAVALKYL-2-PENEM COMPOUNDS AND THEIR PREPARATION AND USE |
| GB8416651D0 (en) * | 1984-06-29 | 1984-08-01 | Erba Farmitalia | Penem derivatives |
| US4617300A (en) * | 1984-09-21 | 1986-10-14 | Schering Corporation | 2(N-heterocyclyl) penems |
| GB8509180D0 (en) * | 1985-04-10 | 1985-05-15 | Erba Farmitalia | Penem derivatives |
| US4891369A (en) * | 1986-12-03 | 1990-01-02 | Taiho Pharmaceutical Company, Limited | 2β-Substituted-methylpenicillanic acid derivatives, and salts and esters thereof |
| EP0275233A1 (en) * | 1987-01-14 | 1988-07-20 | Ciba-Geigy Ag | 2-Heterocyclylalkyl-2-penem compounds |
| IT1262908B (en) * | 1992-09-17 | 1996-07-22 | Menarini Farma Ind | PENEMS DERIVATIVES; THEIR PREPARATION AND PHARMACOLOGICAL COMPOSITIONS THAT CONTAIN THEM |
| DE102014117978A1 (en) | 2013-12-06 | 2015-06-11 | Werth Messtechnik Gmbh | Apparatus and method for measuring workpieces |
| DE102015121582A1 (en) | 2014-12-12 | 2016-06-16 | Werth Messtechnik Gmbh | Method and device for measuring features on workpieces |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4168314A (en) * | 1977-11-17 | 1979-09-18 | Merck & Co., Inc. | 6-(1'-Hydroxyethyl)-2-aminoethylthio-pen-2-em-3-carboxylic acid |
| EP0042026B1 (en) * | 1978-02-02 | 1986-01-08 | Ciba-Geigy Ag | 3,4-disubstituted azetidin-2-on compounds and process for their preparation |
| JPS5625110A (en) * | 1978-12-18 | 1981-03-10 | Bristol Myers Co | Antibacterial |
| AT368506B (en) * | 1979-02-24 | 1982-10-25 | Erba Farmitalia | METHOD FOR PRODUCING NEW PENEM CARBONIC ACIDS AND THEIR SALTS |
| EP0109362A1 (en) * | 1982-11-16 | 1984-05-23 | Ciba-Geigy Ag | Hetereocyclic compounds, process for their preparation, pharmaceutical compositions containing them and their use |
| EP0125207A1 (en) * | 1983-05-06 | 1984-11-14 | Ciba-Geigy Ag | 2-Tetrazolylpropyl-2-penem derivatives, process for their preparation, pharmaceutical compositions containing them and their use |
-
1983
- 1983-11-08 PH PH29799A patent/PH21930A/en unknown
- 1983-11-10 DE DE8383810519T patent/DE3373098D1/en not_active Expired
- 1983-11-10 AT AT83810519T patent/ATE29031T1/en not_active IP Right Cessation
- 1983-11-10 EP EP83810519A patent/EP0110826B1/en not_active Expired
- 1983-11-11 FI FI834139A patent/FI76348C/en not_active IP Right Cessation
- 1983-11-14 IL IL70232A patent/IL70232A/en unknown
- 1983-11-14 PT PT77658A patent/PT77658B/en unknown
- 1983-11-14 ZA ZA838462A patent/ZA838462B/en unknown
- 1983-11-14 DD DD83256670A patent/DD215551A5/en unknown
- 1983-11-14 JP JP58212651A patent/JPS59101492A/en active Pending
- 1983-11-15 HU HU833928A patent/HU192827B/en unknown
- 1983-11-15 NZ NZ206278A patent/NZ206278A/en unknown
- 1983-11-15 IE IE2673/83A patent/IE56236B1/en unknown
- 1983-11-15 KR KR1019830005448A patent/KR840006665A/en not_active Application Discontinuation
- 1983-11-15 AU AU21388/83A patent/AU569264B2/en not_active Expired - Fee Related
- 1983-11-15 GR GR72989A patent/GR79072B/el unknown
- 1983-11-15 ES ES527292A patent/ES8605525A1/en not_active Expired
- 1983-11-15 DK DK522783A patent/DK522783A/en not_active Application Discontinuation
- 1983-11-15 NO NO834189A patent/NO834189L/en unknown
-
1985
- 1985-05-28 ES ES543556A patent/ES8609335A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3373098D1 (en) | 1987-09-24 |
| HU192827B (en) | 1987-07-28 |
| KR840006665A (en) | 1984-12-01 |
| PH21930A (en) | 1988-04-08 |
| ES527292A0 (en) | 1986-03-16 |
| ES8605525A1 (en) | 1986-03-16 |
| FI834139A0 (en) | 1983-11-11 |
| NO834189L (en) | 1984-05-18 |
| ATE29031T1 (en) | 1987-09-15 |
| JPS59101492A (en) | 1984-06-12 |
| EP0110826B1 (en) | 1987-08-19 |
| FI76348C (en) | 1988-10-10 |
| DK522783A (en) | 1984-05-17 |
| EP0110826A1 (en) | 1984-06-13 |
| DK522783D0 (en) | 1983-11-15 |
| IL70232A (en) | 1988-03-31 |
| IE832673L (en) | 1984-05-16 |
| ZA838462B (en) | 1984-06-27 |
| NZ206278A (en) | 1986-05-09 |
| AU569264B2 (en) | 1988-01-28 |
| ES543556A0 (en) | 1986-09-01 |
| ES8609335A1 (en) | 1986-09-01 |
| IE56236B1 (en) | 1991-05-22 |
| FI76348B (en) | 1988-06-30 |
| DD215551A5 (en) | 1984-11-14 |
| GR79072B (en) | 1984-10-02 |
| AU2138883A (en) | 1984-05-24 |
| FI834139A (en) | 1984-05-17 |
| PT77658A (en) | 1983-12-01 |
| PT77658B (en) | 1986-05-12 |
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