YU46193B - Postupak za dobijanje derivata benzimidazol-2-sulfonamida i imidazopiridin-2-sulfonamida - Google Patents
Postupak za dobijanje derivata benzimidazol-2-sulfonamida i imidazopiridin-2-sulfonamidaInfo
- Publication number
- YU46193B YU46193B YU72387A YU72387A YU46193B YU 46193 B YU46193 B YU 46193B YU 72387 A YU72387 A YU 72387A YU 72387 A YU72387 A YU 72387A YU 46193 B YU46193 B YU 46193B
- Authority
- YU
- Yugoslavia
- Prior art keywords
- radical
- alkyl
- group
- atom
- hydrogen atom
- Prior art date
Links
- XRGHQBXKSHAQRB-UHFFFAOYSA-N 1h-benzimidazole-2-sulfonamide Chemical class C1=CC=C2NC(S(=O)(=O)N)=NC2=C1 XRGHQBXKSHAQRB-UHFFFAOYSA-N 0.000 title 1
- FEKKTFYYDHHOBD-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyridine-2-sulfonamide Chemical compound C1=CC=C2NC(S(=O)(=O)N)=NC2=N1 FEKKTFYYDHHOBD-UHFFFAOYSA-N 0.000 title 1
- -1 alkyl radical Chemical class 0.000 abstract 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 7
- 229910052757 nitrogen Inorganic materials 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 5
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- 150000001721 carbon Chemical group 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 150000005840 aryl radicals Chemical class 0.000 abstract 3
- 125000001072 heteroaryl group Chemical group 0.000 abstract 3
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000004442 acylamino group Chemical group 0.000 abstract 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000004076 pyridyl group Chemical group 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 101100439664 Arabidopsis thaliana CHR8 gene Proteins 0.000 abstract 1
- 101100439665 Arabidopsis thaliana SWI2 gene Proteins 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 abstract 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000005129 aryl carbonyl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000002540 isothiocyanates Chemical class 0.000 abstract 1
- 125000000842 isoxazolyl group Chemical group 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000004193 piperazinyl group Chemical group 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 125000003396 thiol group Chemical class [H]S* 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/28—Sulfur atoms
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
u kojoj Z1 je atom azota ili je atom ugljenika iz C-R4; Z2 je atom azota ili je atom ugljenika iz C-R5; Z3 je atom azota ili je atom ugljenika iz C-R6; Z4 je atom azota ili je atom ugljenika iz C-R7; pri cemu samo jedna od grupa Z1, Z2, Z3 i Z4 predstavlja atom azota; R1 i R2 predstavljaju nezavisno atom vodonika, alkil radikal pravog ili racvastog niza, alkilaril, alkilkarbonilalkil, alkilkarbonilaril, alkilkarbonilpiridil, cikloalkil, karboksialkil, acil, nitro, ili R1 i R2 zajedno obrazuju vezu predstavljenu grupom X, pri cemu alkil radikal sam ili u grupi koja ga sadrzi ima od C1 do C5, cikloalkil radikal ima od C3 do C10, aril radikal je od C6 do C12 karbociklicni aromaticni radikal, i acil radikal sadrzi od C1 do C6; R3 predstavlja atom vodonika, alkil radikal pravog ili racvastog niza, aril, heteroaril, alkilaril, hidroksialkil, alkilheteroaril, mono-, bi- ili tri-cikloalkil, alkilamino, N-alkil-alkilamino, alkilkarboksialkil, acil, haloalkil, cijanoalkil, haloaril, alkiltioalkil, alkilsulfonilalkil, alkilsulfonilheteroaril, alkiltioalkilaril, alkilsulfonilalkilaril, N-alkil-N-alkilaril-alkilamino, N-alkilaril-alkilamino, N,N-dialkilalkilamino, adamantil, pri cemu alkil radikal sam ili u grupi ima od C1 do C6, cikloalkil radikal ima od C3 do C10, aril radikal je iz grupe koju cine fenil, naftil i benzil, acil radikal sadrzi od C1 do C6, heteroaril je iz grupe koju cine piridil, izksalolil, morfolino i piperazinil; X predstavlja -(CHR8)n-(CHR9)m-ili -CR8=CR9-; R2 i R3 mogu zajedno da obrazuju vezu predstavljenu grupom -(CH2)nYm-CH R10-; Y predstavlja -CH2-O-CH2- ili -CH2-NR11-CH2-; n predstavlja 1,2,3 ili 4; m je o ili 1; R4 i R7 predstavljaju nezavisno atom vodonika, atom halogena, nitro, amino, ili acilamino kao sto je acetilamino; R5 i R6 predstavljaju nezavisno atom vodonika, halogena, nitro, nizi alkil, trifluorometil, alkoksi, ariloksi, merkapto, alkiltio, alkilsulfinil, alkilsulfonil, izotiocijanat, sulfamoil, alkilkarbonil, arilkarbonil, acilamino kao acetilamino, cijano, karboksil, karboksamido ili karboksialkil; pri tome alkil grupa u alkil radikalu. u radikalu koji sadrzi alkil je C1-C6 alkil grupa, i acil radikal je C1-C6 grupa; R8 i R9 predstavljaju-nezavisno atom vodonika, nizi alkil, aril ili heteroaril, pri tome aril radikal je C6-C12 karbociklicno aromaticni radikal, a heteroaril radikal je petoclani ili sestoclani heterociklicni prsten izabran iz grupe koju cine piridil, izoksazolil i morfolino radikali; R10 predstavlja atom vodonika, radikal -CH2OH, -CH2Cl ili -CH2-; R1 moze da predstavlja vezu sa R10 kad R10 je radikal metilen -CH2- a sam R1 predstavlja vezu; R11 predstavlja atom vodonika, alkil ili hidroksialkil; naznacen tim e, sto suspendovano u vodi ili u 10 do 90%nom vodenom rastvoru sircetne kiseline jedinjenja formule II u kojoj Z1, Z2, Z3, Z4, R1, R4, R5, R6 i R7 imaju napred navedena znacenja, reaguje sa strujom gasovitog hlota u trajanju od 10 minuta do 2 sata tako da se dobija hlorid odgovarajuce sulfonske kis
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8605721A FR2597478B1 (fr) | 1986-04-21 | 1986-04-21 | Benzimidazoles et imidazopyridines sulfonamides, leur preparation et leur application en tant que medicaments. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| YU72387A YU72387A (en) | 1989-02-28 |
| YU46193B true YU46193B (sh) | 1993-05-28 |
Family
ID=9334440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU72387A YU46193B (sh) | 1986-04-21 | 1987-04-21 | Postupak za dobijanje derivata benzimidazol-2-sulfonamida i imidazopiridin-2-sulfonamida |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US4933338A (sh) |
| EP (1) | EP0246126A1 (sh) |
| JP (1) | JPH0643404B2 (sh) |
| KR (1) | KR930003613B1 (sh) |
| CN (1) | CN87102916A (sh) |
| AU (1) | AU608511B2 (sh) |
| BR (1) | BR8701897A (sh) |
| CA (1) | CA1300133C (sh) |
| DD (1) | DD297817A5 (sh) |
| DK (1) | DK185487A (sh) |
| ES (1) | ES2005158A6 (sh) |
| FR (1) | FR2597478B1 (sh) |
| HU (1) | HUT63151A (sh) |
| IN (1) | IN167204B (sh) |
| NO (1) | NO871643L (sh) |
| PL (1) | PL156736B1 (sh) |
| PT (1) | PT84724B (sh) |
| RU (1) | RU1813087C (sh) |
| YU (1) | YU46193B (sh) |
| ZA (1) | ZA872739B (sh) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU195220B (en) * | 1983-05-03 | 1988-04-28 | Byk Gulden Lomberg Chem Fqb | Process for production of new fluor-alkoxi-benzimidasole-derivatives and medical compositions containig them |
| KR950001015B1 (ko) * | 1986-01-10 | 1995-02-07 | 닛뽕 케미화 가부시끼가이샤 | 술폭시드 유도체의 제조방법 |
| WO1989010927A1 (en) * | 1988-05-12 | 1989-11-16 | Eisai Co., Ltd. | Pyridinium salt and pharmacological composition containing the same |
| ZA953311B (en) | 1994-04-29 | 1996-10-24 | Lilly Co Eli | Non-peptidyl tachykinin receptor antagonists |
| US6479514B1 (en) | 1998-05-23 | 2002-11-12 | Altana Pharma Ag | Quinoline-aminomethyl-pyridyl derivatives with anti-helicobacter activity |
| KR20010052503A (ko) | 1998-06-03 | 2001-06-25 | 다니엘 피. 맥컬럼 | Ｎ-헤테로사이클릭 카복실산 또는 카복실산 등입체의ｎ-결합된 설폰아미드 |
| WO2004032861A2 (en) * | 2002-10-11 | 2004-04-22 | Bristol-Myers Squibb Company | Hexahydro-benzimidazolone compounds useful as anti-inflammatory agents |
| CN101497616B (zh) * | 2008-01-30 | 2011-05-18 | 山东轩竹医药科技有限公司 | 含有氨基氧基取代的吡啶的咪唑并吡啶的化合物 |
| CN110551145B (zh) * | 2019-10-24 | 2022-08-05 | 江苏师范大学 | 一类呋喃并香豆素-Tröger’s Base衍生物及其合成方法与应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE502319A (sh) * | 1950-04-04 | |||
| US2603649A (en) * | 1950-04-04 | 1952-07-15 | American Cyanamid Co | Heterocyclic sulfonamides and method of preparing the same |
| GB833049A (en) * | 1957-04-04 | 1960-04-21 | Omikron Gagliardi Soc Di Fatto | Improvements in the preparation of heterocyclic sulfonamides |
| DE2726625A1 (de) * | 1976-06-25 | 1977-12-29 | Ciba Geigy Ag | Verfahren zum flammfestmachen von polyesterfasermaterialien |
| GB8316645D0 (en) * | 1983-06-18 | 1983-07-20 | Wyeth John & Brother Ltd | Heterocyclic compounds |
-
1986
- 1986-04-21 FR FR8605721A patent/FR2597478B1/fr not_active Expired
-
1987
- 1987-04-09 IN IN305/DEL/87A patent/IN167204B/en unknown
- 1987-04-10 DK DK185487A patent/DK185487A/da not_active Application Discontinuation
- 1987-04-13 AU AU71438/87A patent/AU608511B2/en not_active Ceased
- 1987-04-13 CA CA000534593A patent/CA1300133C/fr not_active Expired - Fee Related
- 1987-04-14 ES ES8701081A patent/ES2005158A6/es not_active Expired
- 1987-04-15 US US07/038,874 patent/US4933338A/en not_active Expired - Fee Related
- 1987-04-16 EP EP87400875A patent/EP0246126A1/fr not_active Withdrawn
- 1987-04-16 ZA ZA872739A patent/ZA872739B/xx unknown
- 1987-04-17 HU HU871716A patent/HUT63151A/hu unknown
- 1987-04-20 PT PT84724A patent/PT84724B/pt not_active IP Right Cessation
- 1987-04-20 RU SU874202461A patent/RU1813087C/ru active
- 1987-04-20 DD DD87301968A patent/DD297817A5/de not_active IP Right Cessation
- 1987-04-21 PL PL1987265299A patent/PL156736B1/pl unknown
- 1987-04-21 BR BR8701897A patent/BR8701897A/pt unknown
- 1987-04-21 JP JP62098483A patent/JPH0643404B2/ja not_active Expired - Lifetime
- 1987-04-21 YU YU72387A patent/YU46193B/sh unknown
- 1987-04-21 CN CN198787102916A patent/CN87102916A/zh active Pending
- 1987-04-21 NO NO871643A patent/NO871643L/no unknown
- 1987-04-21 KR KR1019870003936A patent/KR930003613B1/ko not_active IP Right Cessation
-
1989
- 1989-04-28 US US07/344,966 patent/US4943570A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4933338A (en) | 1990-06-12 |
| AU7143887A (en) | 1987-10-22 |
| NO871643L (no) | 1987-10-22 |
| HUT63151A (en) | 1993-07-28 |
| KR930003613B1 (ko) | 1993-05-08 |
| FR2597478A1 (fr) | 1987-10-23 |
| KR870010050A (ko) | 1987-11-30 |
| CA1300133C (fr) | 1992-05-05 |
| PT84724B (pt) | 1989-12-29 |
| JPS62289568A (ja) | 1987-12-16 |
| PL265299A1 (en) | 1988-07-21 |
| PL156736B1 (pl) | 1992-04-30 |
| PT84724A (fr) | 1987-05-01 |
| JPH0643404B2 (ja) | 1994-06-08 |
| CN87102916A (zh) | 1988-04-27 |
| IN167204B (sh) | 1990-09-22 |
| EP0246126A1 (fr) | 1987-11-19 |
| AU608511B2 (en) | 1991-04-11 |
| DD297817A5 (de) | 1992-01-23 |
| FR2597478B1 (fr) | 1988-12-16 |
| YU72387A (en) | 1989-02-28 |
| US4943570A (en) | 1990-07-24 |
| BR8701897A (pt) | 1988-02-02 |
| DK185487A (da) | 1987-10-22 |
| RU1813087C (ru) | 1993-04-30 |
| DK185487D0 (da) | 1987-04-10 |
| ZA872739B (en) | 1987-12-30 |
| NO871643D0 (no) | 1987-04-21 |
| ES2005158A6 (es) | 1989-03-01 |
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