KR850008345A - 세팔로스포린 유도체의 제조방법 - Google Patents
세팔로스포린 유도체의 제조방법 Download PDFInfo
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- KR850008345A KR850008345A KR1019850003162A KR850003162A KR850008345A KR 850008345 A KR850008345 A KR 850008345A KR 1019850003162 A KR1019850003162 A KR 1019850003162A KR 850003162 A KR850003162 A KR 850003162A KR 850008345 A KR850008345 A KR 850008345A
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- carboxyl
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- 238000000034 method Methods 0.000 title claims 5
- 229930186147 Cephalosporin Natural products 0.000 title claims 3
- 229940124587 cephalosporin Drugs 0.000 title claims 3
- 150000001780 cephalosporins Chemical class 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- -1 phosphorus compound Chemical class 0.000 claims 8
- 125000003277 amino group Chemical group 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 231100000252 nontoxic Toxicity 0.000 claims 7
- 230000003000 nontoxic effect Effects 0.000 claims 7
- 150000002148 esters Chemical class 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 239000003153 chemical reaction reagent Substances 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 230000002503 metabolic effect Effects 0.000 claims 4
- 230000000903 blocking effect Effects 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 238000006317 isomerization reaction Methods 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 239000011574 phosphorus Substances 0.000 claims 2
- 150000003018 phosphorus compounds Chemical class 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical group CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 125000004452 carbocyclyl group Chemical group 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004854 thiadizolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/587—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with aliphatic hydrocarbon radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (6)
- (A) R이 아실화된 아미노그룹인 하기 일반식(I)의 화합물을 제조하기 위하여, R이 아미노 또는 실일화된 아미노그룹인 하기 일반식(I)의 화합물 또는 이의염을 아실화시키거나; (B) R이 실일화된 아미노그룹인 하기 일반식(I)의 화합물을 제조하기 위하여, R이 아미노그룹인 하기 일반식(I)의 화합물 또는 이의 염을 실일화시키거나; (C) 하기 일반식(IV)의 화합물을, 3-위치에서 일반식 -CH=CH-C≡C-R2의 그룹을 형성 또는 도입시키기 위한 시약 1종이상과 반응시킴을 특징으로 하는, 하기 일반(I)의 화합물, 이의 염, 이의 용매화합물 및 이의 에스테르의 제조방법.상기식에서, R은 NH2이거나 아실화 또는 실일화된 아미노그룹이고, R2는 수소 또는 할로겐원자이거나 알킬, 아릴, 카복실 또는 저급알콕시카보닐그룹이며, R3는 수소원자 또는 카복실차단그룹이고, B는또는(α- 또는 β-)이며, RA는는 NH2이거나 아실화 또는 실일화된 아미노그룹이거나 아실화된 아미노그룹의 보호된 형태이고, Y는 3- 위치에서 일반식 -CH"aCH-C"aC-R2의 그룹을 형성 또는 도입시키기 위한 언급된 시약 1종이상과 반응할 수 있는 치환체이며, 2-, 3- 및 4- 위치에 연결된 점선은 상기 화합물이 세프-2-엠 또는 세프-3-엠 화합물임을 나타낸다.
- 제1항에 있어서, (A') 하기 일반식(II)의 화합물, 이의 염 또는 이의 N- 실일유도체를 하기 일반식(III)의 산 또는 이에 상응하는 아실화제로 아실화시키거나; (B) 하기 일반식(IVa)의 화합물을, 3-위치에서 일반식 -CH=CH-C"aCH-C"aC-R2의 그룹을 형성 또는 도입시키기 위한 시약 1종이상과 반응시켜 하기 일반식(Id)의 화합물, 이의염, 이의 용매화합물 또는 이의 에스테르를 제조하고; 이어서 필요하다면 하기에서 선택되는 단계를 모든 적당한 순서로 수행함을 특징으로 하는, [(i) "-2-이성체의 "-3-이성체로의 전환, (ii) B가인 화합물의 B가인 화합물로의 화원반응, (iii) B가인 화합물의 S가인 화합물로의 산화반응, (iv) 무독성염의 제조, (v) 용매화합물의 제조, (vi) 무독성 대사성 에스테르의 제조, (vii) 이성체의 분리, (viii) 3-위치 측쇄중의 이중결합의, 시스로부터 트랜스 배위로의 이성화반응 또는 트랜스로부터 시스배위로의 이성화반응, 및 (ix) 카복실차단 그룹 및/또는 O- 또는 N-보호그룹의 제거]; 하기 일반식(Ia)의 화합물, 이의 무독성염, 이의 용매화합물, 이의 1-옥사이드 및 이의 독성대사성 에스테르의 제조방법:상기식에서, R1은 하기의 (i),(ii) 및 (iii)으로부터 선택된 아실그룹이고 [(i) 일반식 RaCH2CO-의 그룹(여기서, Ra는 S, N 및 O로부터 선택된 1개 이상의 헤테로원자를 환에 갖는 임의 치환된 5- 또는 6-원 헤테로시클릭 아릴그룹이다), (ii) 일반식의 그룹(여기서, Rb는 임의 치환된 카보시클리 또는 헤테로시클릭 아릴그룹이고, Rc는 수소원자이거나 임의 치환된 아실, 알킬, 알케닐, 알키닐, 시클로알킬, 시클로알킬, 시클로알킬알킬, 아릴 또는 아르알킬그룹이다), 및 (iii) 일반식의 그룹(여기서, Rd는 전술된 Ra와 동일하거나 임의 치환된 카보시클릭그룹이고, X는 아미노, 하이드록실, 아실화된 하이드록실, 카복실 또는 에스테르화된 카복실그룹이다)], R2는 수소 또는 할로겐원자이거나 알킬, 아릴, 카복실 또는 저급알콕시카보닐그룹이며, R1A는 전술된 R1과 동일하거나 이의 보호된 형태이고, R3는 수소원자이거나 카복실차단그룹이며, B는또는(α- 또는 β-)이고, Y는 3- 위치에서 일반식 -CH=CH-C-C"aR2의 그룹을 형성 또는 도입시키기 위한 시약 1종 이상과 반응할 수 있는 치환체이며, 2-, 3- 또는 4- 위치에 연결된 점선은 화합물이 세프-2-엠 또는 세프-3-엠화합물임을 나타낸다.
- 제1항 또는 제2항에 있어서, 목적화합물이 하기 일반식(Ib)의 화합물, 이의 무독성염, 이의 용매화합물 및 이의 무독성 대사성 에스테르인 방법 :상기식에서 Rb'는 아미노 또는 할로(클로로, 브로모 또는 요오도)로부터 선택된 1개 이상의 치환체로 임의 치환된 티아졸일, 티아디아졸일, 푸릴, 티에닐 또는 피리미딜그룹이고, Rc'는 수소원자이거나, 카바모일, 메틸바카모일, 디메틸카바모일, 카복실, C2-5알콕시카보닐 또는 할로로 임의 치환된 C1-4알킬, C2-4알케닐, C2-4알키닐, C3-6시클로알킬 또는 C3-6시클로알킬-C1-4알킬그룹이며, R2는 수소원자이거나, C1-4알킬, 페닐, 카복실 또는 C2-5알콕시카보닐그룹이다.
- 제1항 내지 제3항중 어느 하나에 있어서, 목적화합물이 하기 일반식(Ic)의 화합물, 이의 무독성염, 이의 용매화합물 및 이의 무독성 대사성 에스테르인 방법:상기식에서, Rc″는 수소원자이거나 메틸, 에틸, 카복시메틸, 2-카복시프로프-2-일, 카바모일메틸 또는 메톡시카보닐 메틸그룹이고, R2'는 수소원자 또는 C1-4알킬그룹이다.
- 제1항 내지 제4항중 어느 하나에 있어서, 목적화합물중의 세팔로스포린 환상의 언급된 3-치환체가 트랜스 배위인 방법.
- 제2항에 있어서, 언급된 일반식(Ia)의 목적화합물이, 세팔로스포린 핵상의 3-치환체가 트랜스 배위인 제1항 및 제3항 내지 제5항의 화합물로부터 선택되는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848411954A GB8411954D0 (en) | 1984-05-10 | 1984-05-10 | Cephalosporin antibiotics |
| GB8411954 | 1984-05-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR850008345A true KR850008345A (ko) | 1985-12-16 |
Family
ID=10560740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019850003162A KR850008345A (ko) | 1984-05-10 | 1985-05-09 | 세팔로스포린 유도체의 제조방법 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4666899A (ko) |
| JP (1) | JPS6156185A (ko) |
| KR (1) | KR850008345A (ko) |
| AT (1) | AT391319B (ko) |
| AU (1) | AU594923B2 (ko) |
| BE (1) | BE902381A (ko) |
| CH (1) | CH671765A5 (ko) |
| DE (1) | DE3516777A1 (ko) |
| DK (1) | DK205085A (ko) |
| ES (1) | ES8702917A1 (ko) |
| FR (1) | FR2564095B1 (ko) |
| GB (2) | GB8411954D0 (ko) |
| IT (1) | IT1181667B (ko) |
| LU (1) | LU86153A1 (ko) |
| NL (1) | NL8501324A (ko) |
| NZ (1) | NZ212029A (ko) |
| SE (1) | SE8502317L (ko) |
| ZA (1) | ZA853518B (ko) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4708955A (en) * | 1985-06-24 | 1987-11-24 | Bristol-Myers Company | 3-(substituted)propenyl-7-aminothiazol-ylcephalosporanic acids and esters thereof |
| US4799708A (en) * | 1986-10-27 | 1989-01-24 | Honda Giken Kogyo Kabushiki Kaisha | Off-road vehicle |
| JPH02124724A (ja) * | 1988-11-02 | 1990-05-14 | Taiyo Yuden Co Ltd | Ｍｎ−Ｚｎ系フェライト材料 |
| US6248881B1 (en) | 1991-03-08 | 2001-06-19 | Biochemie Gmbh | Intermediates and process for the production of 3-vinyl cephalosporins |
| GB0019124D0 (en) | 2000-08-03 | 2000-09-27 | Pfizer | Novel process |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4107431A (en) * | 1970-01-23 | 1978-08-15 | Glaxo Laboratories Limited | Δ3 -3-Vinyl or substituted vinyl-4-carboxy cephalosporins |
| GB1342241A (en) * | 1970-01-23 | 1974-01-03 | Glaxo Lab Ltd | Cephalosporin compounds |
| GB1399086A (en) * | 1971-05-14 | 1975-06-25 | Glaxo Lab Ltd | Cephalosporin compounds |
| US4409214A (en) * | 1979-11-19 | 1983-10-11 | Fujisawa Pharmaceutical, Co., Ltd. | 7-Acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof |
| US4609730A (en) * | 1982-11-22 | 1986-09-02 | Fujisawa Pharmaceutical Co., Ltd. | 7-[substituted imino-2-(2-aminothiazol-4-yl)-acetamido]-3(2,2-dihalovinyl or ethynyl)-3-cephem-4-carboxylic acid (syn isomers), having antimicrobial activities |
| US4520022A (en) * | 1983-01-28 | 1985-05-28 | Bristol-Myers Company | Substituted vinyl cephalosporins |
| US4486586A (en) * | 1983-02-10 | 1984-12-04 | Bristol-Myers Company | Cephalosporin derivatives |
| DE3306102C1 (de) * | 1983-02-22 | 1984-08-02 | Ludwig Heumann & Co GmbH, 8500 Nürnberg | Pyridin-Pyrimidinon-Derivate,Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
-
1984
- 1984-05-10 GB GB848411954A patent/GB8411954D0/en active Pending
-
1985
- 1985-05-09 SE SE8502317A patent/SE8502317L/xx not_active Application Discontinuation
- 1985-05-09 GB GB08511703A patent/GB2159515B/en not_active Expired
- 1985-05-09 DE DE19853516777 patent/DE3516777A1/de not_active Withdrawn
- 1985-05-09 CH CH1982/85A patent/CH671765A5/de not_active IP Right Cessation
- 1985-05-09 NZ NZ212029A patent/NZ212029A/xx unknown
- 1985-05-09 JP JP60096827A patent/JPS6156185A/ja active Pending
- 1985-05-09 AU AU42211/85A patent/AU594923B2/en not_active Expired - Fee Related
- 1985-05-09 DK DK205085A patent/DK205085A/da not_active Application Discontinuation
- 1985-05-09 FR FR8507041A patent/FR2564095B1/fr not_active Expired
- 1985-05-09 ZA ZA853518A patent/ZA853518B/xx unknown
- 1985-05-09 NL NL8501324A patent/NL8501324A/nl not_active Application Discontinuation
- 1985-05-09 ES ES542958A patent/ES8702917A1/es not_active Expired
- 1985-05-09 IT IT48062/85A patent/IT1181667B/it active
- 1985-05-09 BE BE0/214983A patent/BE902381A/fr not_active IP Right Cessation
- 1985-05-09 AT AT0139685A patent/AT391319B/de not_active IP Right Cessation
- 1985-05-09 KR KR1019850003162A patent/KR850008345A/ko not_active Application Discontinuation
- 1985-05-09 US US06/732,094 patent/US4666899A/en not_active Expired - Fee Related
- 1985-11-07 LU LU86153A patent/LU86153A1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT1181667B (it) | 1987-09-30 |
| NL8501324A (nl) | 1985-12-02 |
| IT8548062A1 (it) | 1986-11-09 |
| GB8511703D0 (en) | 1985-06-19 |
| GB8411954D0 (en) | 1984-06-13 |
| JPS6156185A (ja) | 1986-03-20 |
| DK205085D0 (da) | 1985-05-09 |
| AU4221185A (en) | 1985-11-14 |
| FR2564095A1 (fr) | 1985-11-15 |
| GB2159515A (en) | 1985-12-04 |
| DK205085A (da) | 1985-11-11 |
| SE8502317L (sv) | 1985-11-11 |
| ES542958A0 (es) | 1987-01-16 |
| ZA853518B (en) | 1987-01-28 |
| CH671765A5 (ko) | 1989-09-29 |
| AU594923B2 (en) | 1990-03-22 |
| NZ212029A (en) | 1988-09-29 |
| LU86153A1 (fr) | 1986-03-24 |
| ES8702917A1 (es) | 1987-01-16 |
| FR2564095B1 (fr) | 1988-10-14 |
| BE902381A (fr) | 1985-11-12 |
| ATA139685A (de) | 1990-03-15 |
| AT391319B (de) | 1990-09-25 |
| US4666899A (en) | 1987-05-19 |
| DE3516777A1 (de) | 1985-11-14 |
| IT8548062A0 (it) | 1985-05-09 |
| GB2159515B (en) | 1987-12-23 |
| SE8502317D0 (sv) | 1985-05-09 |
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| Date | Code | Title | Description |
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| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |