IE791944L - Pyrrolo-isoquinolines - Google Patents
Pyrrolo-isoquinolinesInfo
- Publication number
- IE791944L IE791944L IE791944A IE194479A IE791944L IE 791944 L IE791944 L IE 791944L IE 791944 A IE791944 A IE 791944A IE 194479 A IE194479 A IE 194479A IE 791944 L IE791944 L IE 791944L
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- hydroxy
- phenyl
- alkoxy
- alkylamino
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1. Claims for the Contracting States : BE, CH, DE, FR, GB, IT, LU, NL, SE. An octahydro-1H-pyrrolo[2,3-g]isoquinoline of the general formula see diagramm : EP0010661,P42,F2 wherein R1 is hydrogen, (C1 -C7 )-alkyl, (C1 -C7 )-alkanoyl or benzoyl or phenyl-(C1 -C7 )-alkyl each of which is optionally substituted on the phenyl ring by halogen, trifluoromethyl, (C1 -C7 )-alkyl, (C1 -C7 )-alkoxy, nitro, amino, (C1 -C7 )-alkylamino or di-(C1 -C7 )-alkylamino, R2 and R3 independently of each other are hydrogen, (C1 -C7 )-alkyl, (C3 -C6 )-cycloalkyl, (C2 -C7 -alkenyl, (C1 -C7 )-alkanoyl or benzoyl, phenyl or phenyl-(C1 -C7 )-alkyl each of which is optionally substituted on the phenyl ring by halogen, trifluoromethyl, (C1 -C7 )-alkyl, (C1 -C7 )-alkoxy, nitro, amino, (C1 -C7 )-alkylamino or di-(C1 -C7 )-alkyl-amino and R4 is hydrogen, (C1 -C7 )-alkyl, hydroxy-(C1 -C7 )-alkyl, phenyl-hydroxy-(C1 -C7 )-alkyl, halophenyl-hydroxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkylphenyl-hydroxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkoxyphenyl-hydroxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkoxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkoxy-hydroxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkanoyloxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkoxycarbonyl-(C1 -C7 )-alkyl, (C2 -C7 )-alkenyl, (C3 -C6 )-cycloalkyl-(C1 -C7 )-alkyl, (C2 -C7 )-alkynyl, thienyl-(C1 -C7 )-alkyl, furyl-(C1 -C7 )-alkyl, (C1 -C7 )-alkanoyl-(C1 -C7 )-alkyl, (C3 -C6 )-cycloalkoxy-(C1 -C7 )-alkyl, (C3 -C6 )-cycloalkyl-hydroxy-(C1 -C7 )-alkyl, (C2 -C7 )-alkenyloxy-(C1 -C7 )-alkyl, N-(C1 -C7 )-alkyl-pyrrolidinyl-(C1 -C7 )-alkyl, trifluoroalkyl with 2 to 6 carbon atoms or phenoxy-hydroxy-(C1 -C7 )-alkyl, benzoyloxy-(C1 -C7 )-alkyl benzoyl-(C1 -C7 )-alkyl, phenyl-(C1 -C7 )-alkyl, phenylcarboxamido-(C1 -C7 )-alkyl, phenyl-(C2 -C7 )-alkenyl, phenoxy-(C1 -C7 )-alkyl or phenyl-N-imidazolonyl-(C1 -C7 )-alkyl each of which is optionally substituted on the phenyl ring by halogen, trifluoromethyl, (C1 -C7 )-alkyl, (C1 -C7 )-alkoxy, nitro, amino, (C1 -C7 )-alkylamino or di-(C1 -C7 )-alkylamino, or see diagramm : EP0010661,P43,F2 wherein R6 and R7 independently of each other are hydrogen or (C1 -C7 )-alkyl or together with the nitrogen atom are a 5- or membered saturated heterocyclic ring which can further contain as a ring member an oxygen atom or a nitrogen atom optionally substituted by (C1 -C7 )-alkyl or hydroxy-(C1 -C7 )-alkyl, and X is O or S, an optical or geometric isomer thereof or a pharmaceutically acceptable acid addition salt thereof. 1. Claims for the Contracting State : AT. A process for the manufacture of octahydro-1H-pyrrolo[2,3-g]isoquinolines of the general formula see diagramm : EP0010661,P47,F3 wherein R1 is hydrogen, (C1 -C7 )-alkyl, (C1 -C7 )-alkanoyl or benzoyl or phenyl-(C1 -C7 )-alkyl each of which is optionally substituted on the phenyl ring by halogen, trifluoromethyl, (C1 -C7 )-alkyl, (C1 -C7 )-alkoxy, nitro, amino, (C1 -C7 )-alkylamino or di-(C1 -C7 )-alkylamino, R2 and R3 independently of each other are hydrogen, (C1 -C7 )-alkyl, (C3 -C6 )-cycloalkyl, (C2 -C7 )-alkenyl, (C1 -C7 )-alkanoyl or benzoyl, phenyl or phenyl-(C1 -C7 )-alkyl each of which is optionally substituted on the phenyl ring by halogen, trifluoromethyl, (C1 -C7 )-alkyl, (C1 -C7 )-alkoxy, nitro, amino, (C1 -C7 )-alkylamino or di-(C1 -C7 )-alkylamino and R4 is hydrogen, (C1 -C7 )-alkyl, hydroxy-(C1 -C7 )-alkyl, phenyl-hydroxy-(C1 -C7 )-alkyl, halophenyl-hydroxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkylphenyl-hydroxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkoxyphenyl-hydroxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkoxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkoxy-hydroxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkanoyloxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkoxycarbonyl- (C1 -C7 )-alkyl, (C2 -C7 )-alkenyl, (C3 -C6 )-cycloalkyl-(C1 -C7 )-alkyl, (C2 -C7 )-alkynyl, thienyl-(C1 -C7 )-alkyl, furyl-(C1 -C7 )-alkyl, (C1 -C7 )-alkanoyl-(C1 -C7 )-alkyl, (C3 -C6 )-cycloalkoxy-(C1 -C7 )-alkyl, (C3 -C6)-cycloalkyl-hydroxy-(C1 -C7 )-alkyl, (C2 -C7 )-alkenyloxy-(C1 -C7 )-alkyl, N-(C1 -C7 )-alkyl-pyrrolidinyl-(C1 -C7 )-alkyl, trifluoroalkyl with 2 to 6 carbon atoms or phenoxy-hydroxy-(C1 -C7 )-alkyl, benzoyloxy-(C1 -C7 )-alkyl, benzoyl-(C1 -C7 )-alkyl, phenyl-(C1 -C7 )-alkyl, phenylcarboxamido-(C1 -C7 )-alkyl, phenyl-(C2 -C7 )-alkenyl, phenoxy-(C1 -C7 )-alkyl or phenyl-N-imidazolonyl-(C1 -C7 )-alkyl each of which is optionally substituted on the phenyl ring by halogen, trifluoromethyl, (C1 -C7 )-alkyl, (C1 -C7 )-alkoxy, nitro, amino, (C1 -C7 )-alkylamino or di-(C1 -C7 )-alkylamino, or see diagramm : EP0010661,P47,F2 wherein R6 and R7 independently of each other are hydrogen or (C1 -C7 )-alkyl or together with the nitrogen atom are a 5- or 6-membered saturated heterocyclic ring which can further contain as a ring member an oxygen atom or a nitrogen atom optionally substituted by (C1 -C7 )-alkyl or hydroxy-(C1 -C7 )-alkyl, and X is O or S, the optical and geometric isomers of these compounds and their pharmaceutically acceptable acid addition salts, characterized by a) for the manufacture of a compound of the general formula see diagramm : EP0010661,P47,F4 wherein R"4 is (C1 -C7 )-alkyl, (C1 -C7 )-alkoxy-(C1 -C7 )-alkyl or (C3 -C6 )-cyclo-alkyl-(C1 -C7 )-alkyl and R2 and R3 are as described previously, treating a compound of the general formula see diagramm : EP0010661,P48,F1 wherein R2 , R3 and R"4 are as described previously, with formaldehyde, or b) for the manufacture of a compound of formula Ia above, treating a compound of the general formula see diagramm : EP0010661,P48,F2 wherein R"4 is as described previously, with a compound of the general formula see diagramm : EP0010661,P48,F3 in the presence of a reducing agent, or with a compound of the general formula see diagramm : EP0010661,P48,F5 wherein R2 and R3 are as described previously, or a precursor thereof, or c) for the manufacture of a compound of the general formula see diagramm : EP0010661,P48,F7 wherein R2 and R3 are as described previously, N-demethylating a compound of formula Ia above wherein R"4 is methyl, or d) for the manufacture of a compound of the general formula see diagramm : EP0010661,P48,F8 wherein R'2 and R'3 independently of each other are hydrogen, (C1 -C7 )-alkyl, (C3 -C6 )-cycloalkyl, (C2 -C7 )-alkenyl or phenyl or phenyl-(C1 -C7 )-alkyl each of which is optionally substituted on the phenyl ring by halogen, trifluoromethyl, (C1 -C7 )-alkyl, (C1 -C7 )-alkoxy, nitro, amino, (C1 -C7 )-alkyl-amino or di-(C1 -C7 )-alkylamino, R'"4 is hydrogen, (C1 -C7 )-alkyl, (C1 -C7 )-alkoxy-(C1 -C7 )-alkyl, (C2 -C7 )-alkenyl, (C3 -C6 )-cycloalkyl-(C1 -C7 )-alkyl, (C2 -C7 )-alkynyl, thienyl-(C1 -C7 )-alkyl, furyl-(C1 -C7 )-alkyl, (C2 -C7 )-alkenyloxy-(C1 -C7 )-alkyl or phenyl-(C1 -C7 )-alkyl, phenyl-(C2 -C7 )-alkenyl or phenoxy-(C1 -C7 )-alkyl each of which is optionally substituted on the phenyl ring by halogen, trifluoro-methyl, (C1 -C7 )-alkyl, (C1 -C7 )-alkoxy, nitro, amino, (C1 -C7 )-alkylamino or di-(C1 -C7 )-alkylamino, or trifluoroalkyl with 2 to 6 carbon atoms and R1 is as described previously, treating a compound of the general formula see diagramm : EP0010661,P48,F4 wherein R1 , R'2 , R'3 and R'"4 are as described previously, with phosphorus pentasulphide, or e) for the manufacture of a compound of the general formula see diagramm : EP0010661,P48,F6 wherein R4-IV is hydroxy-(C1 -C7 )-alkyl, phenyl-hydroxy-(C1 -C7 )-alkyl, halophenyl-hydroxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkyl-phenyl-hydroxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkoxyphenyl-hydroxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkoxy-hydroxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkanoyloxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkoxycarbonyl-(C1 -C7 )-alkyl, (C1 -C7 )-alkanoyl-(C1 -C7 )-alkyl, (C3 -C6 )-cycloalkoxy-(C1 -C7 )-alkyl, (C3 -C6 )-cycloalkyl-hydroxy-(C1 -C7 )-alkyl, N-(C1 -C7 )-alkyl-pyrrolidinyl-(C1 -C7 )-alkyl or phenyl-N-imidazolonyl-(C1 -C7 )-alkyl, phenoxy-hydroxy-(C1 -C7 )-alkyl, benzoyloxy-(C1 -C7 )-alkyl, benzoyl-(C1 -C7 )-alkyl or phenylcarboxamido-(C1 -C7 )-alkyl each of which is optionally substituted on the phenyl ring by halogen, trifluoromethyl, (C1 -C7 )-alkyl, (C1 -C7 )-alkoxy, nitro, amino, (C1 -C7 )-alkylamino or di-(C1 -C7 )-alkylamino, or see diagramm : EP0010661,P48,F9 and R1 , R2 , R3 , R6 and R7 are as described previously, cleaving off the protecting group or protecting groups in a compound of the general formula see diagramm : EP0010661,P49,F1 wherein R"2 and R"3 have the same significance as R2 and R3 except when R2 and R3 are (C1 -C7 )-alkanoyl or benzoyl optionally substituted on the phenyl ring by halogen, trifluoromethyl, (C1 -C7 )-alkyl, (C1 -C7 )-alkoxy, nitro, amino, (C1 -C7 )-alkyl-amino or di-(C1 -C7 )-alkylamino, R"2 and R"3 are in protected form, R4-V has the same significance as R4-IV , but in protected form, and R1 is as described previously, or f) for the manufacture of a compound of the general formula see diagramm : EP0010661,P49,F2 wherein R'1 is (C1 -C7 )-alkyl, (C1 -C7 )-alkanoyl or benzoyl or phenyl-(C1 -C7 )-alkyl each of which is optionally substituted on the phenyl ring by halogen, trifluoromethyl, (C1 -C7 )-alkyl, (C1 -C7 )-alkoxy, nitro, amino, (C1 -C7 )-alkylamino or di-(C1 -C7 )-alkylamino and R2 , R3 , R"4 and X are as described previously, substituting a compound of the general formula see diagramm : EP0010661,P49,F5 wherein R2 , R3 , R"4 and X are as described previously, at the pyrrole nitrogen atom, or g) for the manufacture of a compound of the general formula see diagramm : EP0010661,P49,F7 wherein R'4 is (C1 -C7 )-alkyl, hydroxy-(C1 -C7 )-alkyl, phenyl-hydroxy-(C1 -C7 )-alkyl, halophenyl-hydroxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkylphenyl-hydroxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkoxyphenyl-hydroxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkoxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkoxy-hydroxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkanoyloxy-(C1 -C7 )-alkyl, (C1 -C7 )-alkoxycarbonyl-(C1 -C7 )-alkyl, (C2 -C7 )-alkenyl, (C3 -C6 )-cycloalkyl-(C1 -C7 )-alkyl, (C2 -C7 )-alkynyl, thienyl-(C1 -C7 )-alkyl, furyl-(C1 -C7 )-alkyl, (
[EP0010661A2]
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US95094778A | 1978-10-13 | 1978-10-13 | |
US06/073,813 US4260762A (en) | 1979-09-10 | 1979-09-10 | Octahydro-1H-pyrrolo[2,3-g]isoquinolines |
Publications (2)
Publication Number | Publication Date |
---|---|
IE791944L true IE791944L (en) | 1980-04-13 |
IE48965B1 IE48965B1 (en) | 1985-06-26 |
Family
ID=26754910
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IE1944/79A IE48965B1 (en) | 1978-10-13 | 1979-10-12 | Isoquinoline derivatives,process for their preparation,medicaments containing them and their pharmaceutical use |
Country Status (18)
Country | Link |
---|---|
EP (1) | EP0010661B1 (en) |
AR (2) | AR228244A1 (en) |
AU (1) | AU528685B2 (en) |
CA (1) | CA1132553A (en) |
CS (1) | CS242858B2 (en) |
DE (1) | DE2967215D1 (en) |
DK (1) | DK430579A (en) |
ES (2) | ES493015A0 (en) |
FI (1) | FI67548C (en) |
HU (1) | HU181883B (en) |
IE (1) | IE48965B1 (en) |
IL (1) | IL58438A (en) |
MC (1) | MC1285A1 (en) |
NO (1) | NO152873C (en) |
NZ (1) | NZ191830A (en) |
PH (1) | PH14835A (en) |
PT (1) | PT70310A (en) |
SU (3) | SU1109052A3 (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
MC1377A1 (en) * | 1980-02-28 | 1982-01-19 | Hoffmann La Roche | ISOQUINOLEIN DERIVATIVES |
EP0091565B1 (en) * | 1982-03-29 | 1986-04-23 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Process for the manufacture of isoquinoline diones |
US4732902A (en) * | 1986-05-23 | 1988-03-22 | Hoffmann-La Roche Inc. | Pyrroloisoquinolinyl-dimethyloxoalkyl alkonoates and their use as antipsychotic agents |
GB8828669D0 (en) * | 1988-12-08 | 1989-01-11 | Lilly Industries Ltd | Organic compounds |
CN1326437A (en) * | 1998-11-20 | 2001-12-12 | 巴斯福股份公司 | Method and intermediate products for producing BIS(oxim) monoethers |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS51118799A (en) * | 1975-04-10 | 1976-10-18 | Sankyo Co Ltd | Method for preparing pyridindole derivatives |
-
1979
- 1979-09-27 CA CA336,495A patent/CA1132553A/en not_active Expired
- 1979-10-08 SU SU792819251A patent/SU1109052A3/en active
- 1979-10-08 SU SU812819251K patent/SU1014474A3/en active
- 1979-10-10 MC MC791409A patent/MC1285A1/en unknown
- 1979-10-11 AU AU51697/79A patent/AU528685B2/en not_active Ceased
- 1979-10-11 IL IL58438A patent/IL58438A/en unknown
- 1979-10-11 EP EP79103908A patent/EP0010661B1/en not_active Expired
- 1979-10-11 DK DK430579A patent/DK430579A/en not_active Application Discontinuation
- 1979-10-11 NZ NZ191830A patent/NZ191830A/en unknown
- 1979-10-11 DE DE7979103908T patent/DE2967215D1/en not_active Expired
- 1979-10-12 IE IE1944/79A patent/IE48965B1/en unknown
- 1979-10-12 NO NO793301A patent/NO152873C/en unknown
- 1979-10-12 CS CS796945A patent/CS242858B2/en unknown
- 1979-10-12 HU HU79HO2188A patent/HU181883B/en not_active IP Right Cessation
- 1979-10-12 PT PT70310A patent/PT70310A/en unknown
- 1979-10-12 PH PH23160A patent/PH14835A/en unknown
- 1979-10-12 AR AR278488A patent/AR228244A1/en active
- 1979-10-12 FI FI793183A patent/FI67548C/en not_active IP Right Cessation
-
1980
- 1980-07-02 ES ES493015A patent/ES493015A0/en active Granted
- 1980-07-02 ES ES493014A patent/ES493014A0/en active Granted
-
1981
- 1981-03-02 SU SU813250198A patent/SU1048985A3/en active
- 1981-07-02 AR AR285961A patent/AR229096A1/en active
Also Published As
Publication number | Publication date |
---|---|
NZ191830A (en) | 1984-09-28 |
IL58438A0 (en) | 1980-01-31 |
SU1014474A3 (en) | 1983-04-23 |
EP0010661B1 (en) | 1984-09-12 |
CS242858B2 (en) | 1986-05-15 |
EP0010661A3 (en) | 1980-10-01 |
NO152873C (en) | 1985-12-04 |
PT70310A (en) | 1979-11-01 |
NO152873B (en) | 1985-08-26 |
FI67548B (en) | 1984-12-31 |
ES8104805A1 (en) | 1981-05-16 |
SU1048985A3 (en) | 1983-10-15 |
FI793183A (en) | 1980-04-14 |
CA1132553A (en) | 1982-09-28 |
AU528685B2 (en) | 1983-05-12 |
AU5169779A (en) | 1980-04-17 |
AR229096A1 (en) | 1983-06-15 |
NO793301L (en) | 1980-04-15 |
HU181883B (en) | 1983-11-28 |
IE48965B1 (en) | 1985-06-26 |
FI67548C (en) | 1985-04-10 |
DE2967215D1 (en) | 1984-10-18 |
MC1285A1 (en) | 1980-07-22 |
EP0010661A2 (en) | 1980-05-14 |
ES8104806A1 (en) | 1981-05-16 |
SU1109052A3 (en) | 1984-08-15 |
IL58438A (en) | 1982-12-31 |
CS694579A2 (en) | 1985-08-15 |
PH14835A (en) | 1981-12-16 |
ES493015A0 (en) | 1981-05-16 |
ES493014A0 (en) | 1981-05-16 |
AR228244A1 (en) | 1983-02-15 |
DK430579A (en) | 1980-04-14 |
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