NO822360L - Fremgangsmaate ved fremstilling av nye indolderivater - Google Patents
Fremgangsmaate ved fremstilling av nye indolderivaterInfo
- Publication number
- NO822360L NO822360L NO822360A NO822360A NO822360L NO 822360 L NO822360 L NO 822360L NO 822360 A NO822360 A NO 822360A NO 822360 A NO822360 A NO 822360A NO 822360 L NO822360 L NO 822360L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- methyl
- acid
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims description 46
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- -1 1-imidazolyl Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
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- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims 1
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- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 229940127217 antithrombotic drug Drugs 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
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- 239000007864 aqueous solution Substances 0.000 description 1
- 230000007214 atherothrombosis Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000003727 cerebral blood flow Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000003544 deproteinization Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 1
- 229960002986 dinoprostone Drugs 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000010102 embolization Effects 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- PTCGDEVVHUXTMP-UHFFFAOYSA-N flutolanil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 PTCGDEVVHUXTMP-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 150000003278 haem Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 230000035874 hyperreactivity Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229940118019 malondialdehyde Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000328 pro-aggregatory effect Effects 0.000 description 1
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 description 1
- XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 description 1
- SGUKUZOVHSFKPH-YNNPMVKQSA-N prostaglandin G2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](OO)CCCCC)[C@H]2C\C=C/CCCC(O)=O SGUKUZOVHSFKPH-YNNPMVKQSA-N 0.000 description 1
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 208000014221 sudden cardiac arrest Diseases 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 208000032598 susceptibility microvascular complications of diabetes Diseases 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 150000003595 thromboxanes Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8120878 | 1981-07-07 | ||
| GB8213864 | 1982-05-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO822360L true NO822360L (no) | 1983-01-10 |
Family
ID=26280039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO822360A NO822360L (no) | 1981-07-07 | 1982-07-06 | Fremgangsmaate ved fremstilling av nye indolderivater |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4451472A (da) |
| EP (1) | EP0069513B1 (da) |
| AR (1) | AR230056A1 (da) |
| AU (1) | AU532640B2 (da) |
| CS (1) | CS229934B2 (da) |
| DD (1) | DD202714A5 (da) |
| DE (1) | DE3275545D1 (da) |
| DK (1) | DK297382A (da) |
| ES (1) | ES8305355A1 (da) |
| FI (1) | FI822386L (da) |
| GB (1) | GB2101992A (da) |
| GR (1) | GR76214B (da) |
| IL (1) | IL66223A0 (da) |
| NO (1) | NO822360L (da) |
| PL (1) | PL240814A1 (da) |
| PT (1) | PT75191B (da) |
| YU (1) | YU145482A (da) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4536505A (en) * | 1983-05-17 | 1985-08-20 | Ciba-Geigy Corporation | Certain N-(pyridyl) indoles |
| US4609733A (en) * | 1984-12-27 | 1986-09-02 | Ciba-Geigy Corporation | 3-keto-substituted-N-pyridylindoles |
| CA2030557A1 (en) * | 1989-03-31 | 1990-10-01 | Hiroshi Matsui | Imidazole derivatives, methods for their production and pharmaceutical use thereof |
| JPH03258779A (ja) * | 1990-03-06 | 1991-11-19 | Mitsui Toatsu Chem Inc | イミダゾール誘導体及び該イミダゾール誘導体を有効成分とする抗痙攣剤 |
| US5538973A (en) * | 1992-03-27 | 1996-07-23 | Kyoto Pharmaceutical Industries, Ltd. | Imidazole derivative, pharmaceutical use thereof, and intermediate therefor |
| GB9310635D0 (en) * | 1993-05-21 | 1993-07-07 | Glaxo Group Ltd | Chemical compounds |
| GB9319100D0 (en) * | 1993-09-15 | 1993-11-03 | Pfizer Ltd | 3-(3-pyridinyl)h-indoles |
| PL2736887T3 (pl) | 2011-07-29 | 2018-03-30 | Karyopharm Therapeutics, Inc. | Modulatory transportu jądrowego zawierające ugrupowanie hydrazydu i ich zastosowania |
| LT2858991T (lt) | 2012-05-09 | 2018-11-26 | Biogen Ma Inc. | Branduolinio transporto moduliatoriai ir jų panaudojimas |
| EP2968278B8 (en) | 2013-03-15 | 2019-05-22 | Karyopharm Therapeutics Inc. | Methods of promoting wound healing using crm1 inhibitors |
| BR112015032071B1 (pt) | 2013-06-21 | 2022-06-14 | Karyopharm Therapeutics Inc | Modulares do transporte nuclear e suas utilizações |
| CN111481553B (zh) | 2014-08-15 | 2023-09-01 | 卡尔约药物治疗公司 | 赛灵克斯的多晶型物 |
| MA43529A (fr) | 2015-12-31 | 2018-11-07 | Karyopharm Therapeutics Inc | Modulateurs de transport nucléaire et leurs utilisations |
| EP3397634A1 (en) | 2015-12-31 | 2018-11-07 | Karyopharm Therapeutics, Inc. | Nuclear transport modulators and uses thereof |
| WO2018098472A1 (en) | 2016-11-28 | 2018-05-31 | Karyopharm Therapeutics Inc. | Crm1 inhibitors for treating epilepsy |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3462440A (en) * | 1965-12-03 | 1969-08-19 | American Home Prod | 1,4-bis(2-indol-3-ylethyl)piperidines |
| FR2272081A1 (en) * | 1974-05-22 | 1975-12-19 | Labaz | Anti-inflammatory indolylpyridylketones prepn. - from 2-alkyl (or aryl) indole and pyridine carboxylic acid chlorides |
| DE2960547D1 (en) * | 1978-02-24 | 1981-11-05 | Pfizer Ltd | 3-(imidazol-1-ylalkyl)indoles as selective inhibitors of thromboxane synthetase,pharmaceutical compositions thereof, and methods for preparing them |
| IT1162310B (it) * | 1978-05-02 | 1987-03-25 | Ono Pharmaceutical Co | Derivati di imidazolo e procedimento per produrli |
| JPS55313A (en) * | 1978-06-13 | 1980-01-05 | Kissei Pharmaceut Co Ltd | Imidazole derivative |
| JPS5951943B2 (ja) * | 1978-08-21 | 1984-12-17 | キツセイ薬品工業株式会社 | 新規なイミダゾ−ル誘導体 |
| GB2045244B (en) * | 1979-03-07 | 1983-01-26 | Pfizer Ltd | 3-1-(imidazolylalkyl) indoles |
| US4363912A (en) * | 1980-12-15 | 1982-12-14 | Pfizer Inc. | Indole thromboxane synthetase inhibitors |
-
1982
- 1982-06-23 CS CS825037A patent/CS229934B2/cs unknown
- 1982-06-25 GB GB08218431A patent/GB2101992A/en not_active Withdrawn
- 1982-06-25 EP EP82303313A patent/EP0069513B1/en not_active Expired
- 1982-06-25 DE DE8282303313T patent/DE3275545D1/de not_active Expired
- 1982-07-01 PL PL24081482A patent/PL240814A1/xx unknown
- 1982-07-02 AR AR289873A patent/AR230056A1/es active
- 1982-07-02 US US06/394,554 patent/US4451472A/en not_active Expired - Fee Related
- 1982-07-02 DK DK297382A patent/DK297382A/da unknown
- 1982-07-05 YU YU01454/82A patent/YU145482A/xx unknown
- 1982-07-05 GR GR68642A patent/GR76214B/el unknown
- 1982-07-05 IL IL66223A patent/IL66223A0/xx unknown
- 1982-07-05 FI FI822386A patent/FI822386L/fi not_active Application Discontinuation
- 1982-07-06 PT PT75191A patent/PT75191B/pt unknown
- 1982-07-06 NO NO822360A patent/NO822360L/no unknown
- 1982-07-06 AU AU85638/82A patent/AU532640B2/en not_active Ceased
- 1982-07-06 ES ES513765A patent/ES8305355A1/es not_active Expired
- 1982-07-06 DD DD82241446A patent/DD202714A5/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES513765A0 (es) | 1983-04-01 |
| AU8563882A (en) | 1983-02-03 |
| DK297382A (da) | 1983-01-08 |
| EP0069513A3 (en) | 1984-03-21 |
| IL66223A0 (en) | 1982-11-30 |
| PT75191B (en) | 1985-10-04 |
| AU532640B2 (en) | 1983-10-06 |
| GR76214B (da) | 1984-08-04 |
| ES8305355A1 (es) | 1983-04-01 |
| DD202714A5 (de) | 1983-09-28 |
| EP0069513A2 (en) | 1983-01-12 |
| GB2101992A (en) | 1983-01-26 |
| FI822386A0 (fi) | 1982-07-05 |
| CS229934B2 (en) | 1984-07-16 |
| YU145482A (en) | 1985-03-20 |
| US4451472A (en) | 1984-05-29 |
| FI822386L (fi) | 1983-01-08 |
| DE3275545D1 (en) | 1987-04-09 |
| PL240814A1 (en) | 1983-10-10 |
| EP0069513B1 (en) | 1987-03-04 |
| AR230056A1 (es) | 1984-02-29 |
| PT75191A (en) | 1982-08-01 |
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