KR840005141A - 구아닌 유도체 및 그 제조방법 - Google Patents
구아닌 유도체 및 그 제조방법 Download PDFInfo
- Publication number
- KR840005141A KR840005141A KR1019830002777A KR830002777A KR840005141A KR 840005141 A KR840005141 A KR 840005141A KR 1019830002777 A KR1019830002777 A KR 1019830002777A KR 830002777 A KR830002777 A KR 830002777A KR 840005141 A KR840005141 A KR 840005141A
- Authority
- KR
- South Korea
- Prior art keywords
- methoxy
- hydrogen
- fluoro
- compound
- methylthio
- Prior art date
Links
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical class O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 239000001257 hydrogen Substances 0.000 claims 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 19
- 125000001153 fluoro group Chemical group F* 0.000 claims 14
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000006239 protecting group Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- -1 cyclic acetal compounds Chemical class 0.000 claims 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 3
- 239000011630 iodine Chemical group 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- 230000003287 optical effect Effects 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 2
- MJGPTHPXMVMHPS-UHFFFAOYSA-N 1,3,2-dioxathietan-4-one Chemical class O=C1OSO1 MJGPTHPXMVMHPS-UHFFFAOYSA-N 0.000 claims 1
- UZSNCIPFGCERGD-UHFFFAOYSA-N 1-amino-1-nitro-3-oxourea Chemical compound N(=O)C(=O)N(N)[N+](=O)[O-] UZSNCIPFGCERGD-UHFFFAOYSA-N 0.000 claims 1
- WJSVJNDMOQTICG-UHFFFAOYSA-N 2-amino-1-[(2-methyl-4-methylidene-5-oxooxolan-2-yl)methyl]-7h-purin-6-one Chemical group NC1=NC=2N=CNC=2C(=O)N1CC1(C)CC(=C)C(=O)O1 WJSVJNDMOQTICG-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 150000001349 alkyl fluorides Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000006242 amine protecting group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000002926 oxygen Chemical class 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 238000007910 systemic administration Methods 0.000 claims 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 claims 1
- 150000003568 thioethers Chemical class 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/16—Radicals substituted by halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (5)
- 약학적으로 알맞은 담체에 관련하여 활성성분으로써 하기식(I)의 화합물, 생리학적으로 알맞은 염이나 이들의 광학이성체를 구성하는 제약조성물.상기식에서, R1은 수소 R2는 수소, 플루오로, 메톡시 또는 메틸티오, R3는 수소, 하드록시 또는 메르캅토; 조건부로 R3가 수소이면 R2는 메톡시 또는 메틸티오, R3가 히드록시이면 R2는 플루오로, 메톡시 또는 메틸티오이다. 한편 R2가 메톡시 또는 플루오로일때 R1가 메톡시 또는 플루오로가 될 수 있다.
- 제1항에 있어서, 전신투여용으로 적용되는 제약조성물.
- 제1항에 있어서, 국소투여용으로 적용되는 제약조성물.
- 식 Ⅱ의 화합물에서 비환식 측쇄를 식 Ⅲ의 구아닌 유도체 N-9위치에 축합시켜 가능한 보호기를 제거하거나, 식 Ⅳ의 화합물에서 치환 반응에 따라 가능한 보호기를 제거하거나, 식 Ⅴ의 화합물에서에 스테르기의 환원 알콜화반응에 따라 가능한 보호기를 제거하거나, 식 Ⅵ의 화합물의 폐환에 따라, 가능한 보호기를 제거하거나, 식 Ⅶ의 화합물의 폐환에 따라 가능한 보호기를 제거하거나, 식 Ⅷ의 화합물의 피리미딘환치환에 따라 가능한 보호기를 제거하여, 식 I 의 화합물이나 생리학적으로 알맞은 염 및 광학적 이성체(여기서, 산출된 염기는 약학적으로 알맞은 염으로 전환되고, 산출된 염은 염기 또는 상이한 약학적으로 알맞은 염으로 전환되며, 산출된 이성체 혼합물은 순수한 에난티오머(enantiomeric isomer)로 분리됨)를 제조하는 방법.상기식들중에서 R1은 수소, R2는 수소, 플루오로, 메톡시 또는 메틸티오, R3는 수소, 히드록시 또는 메르캅토, 조건부로 R3가 수소이면, R2는 메톡시 또는 메틸티오, R3가 히드록시이며, R2는 플루오로, 메톡시 또는 메틸티오이다. 한편, R2가 메톡시 또는 플루오로일때 R1도 메톡시 또는 플루오로가 될 수 있다. X는 염소, 브롬, 요오드 또는 OSO2R10기, R10은 탄소원자가 1-8인 알킬, 트리플루오로메틸같은 탄소원자가 1-8인 불화알킬, 알킬아릴 또는 아릴, Y는 수소 또는 테트라부틸암모늄 같은 4급 암모늄, R5는 상기와 같은 R3,또는 OR6나 SR5또는 산소유도체 OR12나SO2R10으로써 R6는 수소나 히드록실보호기, R5및 OR6는 R3가 OH일때 선별적으로 에폭사이드를 함께 형성하거나 카보네이트 에스테르, 카보네이트 티오에스테르 또는 상응하는 정산시크릭 유도체 또는 시크릭 아세탈형 화합물같은 시크릭 유도체를 형성한다.R7은 히드록실, 염소, 브롬, 요오드, 티오, 티오에테르, SO2R10, R12는 알킬알킬, 아릴치환된시킬, 포스포릴 디에스테르, 포스피노티오닐, R8및 R9는 상이하거나 같으며 R11이다.R11은 수소 또는 아민보호기, R13은R1, 요오드, 티오 또는 OSO2R10, R14는 R2, 요오드 또는 OSO2R10, R15는 R3,요오드 또는 OSO2R10, Z는 NH2또는 알콕시기, R16은NH2또는 구아니딘 R17은 니트로소, 니트로, 아미노, 포름미아드 또는 아미노오르도 에스테로, 할로겐은 플루오로, 클로로, 브롬, 요오드, H18은 히드록실 또는 아미노로써, R18이 아미노일때 아미노기는 히드록실기로 전환된다.
- 제4항에 있어서, R3는 수소, R1는 수소, 플루오로 및 메톡시중의 하나, R2는 플루오로, 메톡시 및 메틸티오중의 하나(조건부로 R3가 수소이면 R2는 메톡시나 메틸티오, 또한 R2가 메톡시나 플루오로이면 R1도 메톡시나 플루오로일 수 있다)인 화합물이거나 R1및R2는 수소 R3는 메르캅토인 화합물이거나 R1은 수소, R2는 플루오로, R3는 히드록시인 화합물이거나 R1은 수소, R2는 메톡시, R3는 히드록시인 화합물이거나 R1및 R2는 메톡시, R3는 수소인 화합물이거나, R3는 수소인 화합물이거나, 및 R1는 메톡시 R2는메톡시 R3는 히드록시인 화합물 및 생리학적으로 알맞은 염 및 이들의 광학이성체를 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8203855-5 | 1982-06-21 | ||
| SE8203855A SE8203855D0 (sv) | 1982-06-21 | 1982-06-21 | Novel derivatives of guanine i |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR840005141A true KR840005141A (ko) | 1984-11-03 |
Family
ID=20347137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830002777A KR840005141A (ko) | 1982-06-21 | 1983-06-21 | 구아닌 유도체 및 그 제조방법 |
Country Status (17)
| Country | Link |
|---|---|
| EP (2) | EP0112353A1 (ko) |
| JP (1) | JPS59501112A (ko) |
| KR (1) | KR840005141A (ko) |
| AT (1) | ATE18225T1 (ko) |
| AU (1) | AU1706083A (ko) |
| DD (1) | DD210274A5 (ko) |
| DE (1) | DE3362283D1 (ko) |
| ES (1) | ES8500942A1 (ko) |
| GB (1) | GB2122198B (ko) |
| GR (1) | GR78621B (ko) |
| IS (1) | IS2822A7 (ko) |
| NZ (1) | NZ204640A (ko) |
| PH (1) | PH19399A (ko) |
| PT (1) | PT76902B (ko) |
| SE (1) | SE8203855D0 (ko) |
| WO (1) | WO1984000167A1 (ko) |
| ZA (1) | ZA834532B (ko) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5684153A (en) | 1984-08-16 | 1997-11-04 | Beecham Group Plc | Process for the preparation of purine derivatives |
| IL73682A (en) * | 1983-12-20 | 1991-08-16 | Medivir Ab | Antiviral pharmaceutical compositions containing 9-hydroxy aliphatic derivatives of guanine,some new such derivatives and process for their preparation |
| EP0152316B1 (en) * | 1984-01-26 | 1989-07-26 | Merck & Co. Inc. | Substituted butyl guanines and their utilization in antiviral compositions |
| US4617304A (en) * | 1984-04-10 | 1986-10-14 | Merck & Co., Inc. | Purine derivatives |
| ES2001094A6 (es) * | 1985-08-16 | 1988-04-16 | Glaxo Group Ltd | Un procedimiento para la preparacion de un derivado de guanina |
| DE3627024A1 (de) | 1985-09-24 | 1987-04-02 | Hoechst Ag | In 6- und 9-stellung substituierte 2-aminopurine, ihre verwendung, diese purine enthaltende arzneimittel und verfahren zur herstellung der purine |
| DE3604899A1 (de) * | 1986-02-17 | 1987-08-20 | Hoechst Ag | Chirale umsetzungsprodukte aus mesogenen molekuelbausteinen und bifunktionell reaktionsfaehigen butantetraolderivaten und ihre verwendung als dotierstoff in fluessigkristall-phasen |
| US4916225A (en) * | 1986-11-25 | 1990-04-10 | Institut Organicheskogo Sinteza Akademii Nauk Latviiskoi Ssr | 9-substituted guanines |
| US4973318A (en) * | 1988-02-10 | 1990-11-27 | D.C.P. Af 1988 A/S | Disposable syringe |
| US5216141A (en) * | 1988-06-06 | 1993-06-01 | Benner Steven A | Oligonucleotide analogs containing sulfur linkages |
| US4966895A (en) * | 1989-02-02 | 1990-10-30 | Merck & Co. Inc. | Cyclic monophosphates of purine and pyrimidine acyclonucleosides as anti-retroviral agents |
| PT1144607E (pt) | 1999-07-20 | 2009-04-22 | Morphosys Ag | Novos métodos para apresentar (poli)peptídeos/ proteínas em partículas bacteriofágicas através de ligações dissulfureto |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1523865A (en) * | 1974-09-02 | 1978-09-06 | Wellcome Found | Purine compunds and salts thereof |
| US4230708A (en) * | 1977-10-20 | 1980-10-28 | Stichting Rega V.Z.W. | Therapeutic application of (S) -or (RS)-9-(2, 3-dihydroxypropyl) adenine for use as antiviral agents |
| US4221910A (en) * | 1978-09-15 | 1980-09-09 | Newport Pharmaceuticals International, Inc. | 9-(Hydroxy alkyl)purines |
| IL64501A (en) * | 1980-12-22 | 1985-07-31 | Astra Laekemedel Ab | 9-substituted 4-hydroxybutyl guanine derivatives,their preparation and antiviral use |
-
1982
- 1982-06-21 SE SE8203855A patent/SE8203855D0/xx unknown
-
1983
- 1983-06-20 EP EP83901965A patent/EP0112353A1/en active Pending
- 1983-06-20 GB GB08316743A patent/GB2122198B/en not_active Expired
- 1983-06-20 JP JP58502135A patent/JPS59501112A/ja active Pending
- 1983-06-20 AU AU17060/83A patent/AU1706083A/en not_active Abandoned
- 1983-06-20 EP EP83850170A patent/EP0103551B1/en not_active Expired
- 1983-06-20 WO PCT/SE1983/000254 patent/WO1984000167A1/en not_active Application Discontinuation
- 1983-06-20 ES ES523425A patent/ES8500942A1/es not_active Expired
- 1983-06-20 PT PT76902A patent/PT76902B/pt unknown
- 1983-06-20 DE DE8383850170T patent/DE3362283D1/de not_active Expired
- 1983-06-20 NZ NZ204640A patent/NZ204640A/en unknown
- 1983-06-20 AT AT83850170T patent/ATE18225T1/de not_active IP Right Cessation
- 1983-06-20 GR GR71722A patent/GR78621B/el unknown
- 1983-06-20 PH PH29089A patent/PH19399A/en unknown
- 1983-06-21 ZA ZA834532A patent/ZA834532B/xx unknown
- 1983-06-21 IS IS2822A patent/IS2822A7/is unknown
- 1983-06-21 DD DD83252201A patent/DD210274A5/de unknown
- 1983-06-21 KR KR1019830002777A patent/KR840005141A/ko not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU1706083A (en) | 1984-01-26 |
| EP0103551A3 (en) | 1984-06-13 |
| PH19399A (en) | 1986-04-10 |
| GB2122198B (en) | 1985-11-06 |
| GR78621B (ko) | 1984-09-27 |
| ATE18225T1 (de) | 1986-03-15 |
| GB2122198A (en) | 1984-01-11 |
| PT76902B (en) | 1986-04-09 |
| JPS59501112A (ja) | 1984-06-28 |
| NZ204640A (en) | 1986-07-11 |
| SE8203855D0 (sv) | 1982-06-21 |
| ES523425A0 (es) | 1984-11-01 |
| PT76902A (en) | 1983-07-01 |
| DE3362283D1 (en) | 1986-04-03 |
| ZA834532B (en) | 1984-03-28 |
| ES8500942A1 (es) | 1984-11-01 |
| WO1984000167A1 (en) | 1984-01-19 |
| GB8316743D0 (en) | 1983-07-20 |
| EP0112353A1 (en) | 1984-07-04 |
| EP0103551B1 (en) | 1986-02-26 |
| DD210274A5 (de) | 1984-06-06 |
| IS2822A7 (is) | 1986-02-28 |
| EP0103551A2 (en) | 1984-03-21 |
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| Date | Code | Title | Description |
|---|---|---|---|
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |