KR920700217A - 항 바이러스성 화합물 - Google Patents
항 바이러스성 화합물Info
- Publication number
- KR920700217A KR920700217A KR1019900702612A KR900702612A KR920700217A KR 920700217 A KR920700217 A KR 920700217A KR 1019900702612 A KR1019900702612 A KR 1019900702612A KR 900702612 A KR900702612 A KR 900702612A KR 920700217 A KR920700217 A KR 920700217A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- phosphate
- methylsulfonyl
- compound according
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract 25
- 230000000840 anti-viral effect Effects 0.000 title abstract 2
- 239000002777 nucleoside Substances 0.000 claims abstract 6
- 150000003833 nucleoside derivatives Chemical class 0.000 claims abstract 5
- 125000003118 aryl group Chemical group 0.000 claims abstract 3
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- -1 carboalkoxy Chemical group 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 241000282412 Homo Species 0.000 claims 3
- 206010038997 Retroviral infections Diseases 0.000 claims 3
- 241000700605 Viruses Species 0.000 claims 3
- 241000725303 Human immunodeficiency virus Species 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- 238000011282 treatment Methods 0.000 claims 2
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical group CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 208000005074 Retroviridae Infections Diseases 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 150000001555 benzenes Chemical group 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229940104302 cytosine Drugs 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 1
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000003835 nucleoside group Chemical group 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 150000004965 peroxy acids Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 230000010076 replication Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 230000001988 toxicity Effects 0.000 claims 1
- 231100000419 toxicity Toxicity 0.000 claims 1
- 230000029812 viral genome replication Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
-
- 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
- A61P31/12—Antivirals
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Abstract
내용 없음
Description
내용없음
Claims (30)
- 하기 일반식(Ⅰ)의 화합물 또는 약리학적으로 허용 가능한 이들의 염:상기식에서, R1은 지방족 히드로카르빌기이고; Ar은 치환 또는 비치환된 방향족핵이고; X는 -SO2- 또는 -CO-이고; R2및 R3는 같거나 다를 수 있으며 하기 일반식(a), (b), (c), (d), (e), (f), (g), (h) 또는 (ⅰ)의 부분들이고:상기식에서, B는 하기 일반식(A), (G), (C), (H) 또는 (T)의 뉴클레오시드염기의 잔기이며:단, R2및 R3가 일반식(a)의 비치환된 부분일 경우, B는 일반식(A), (G), (C) 또는 (H)의 뉴클레오시드염기이다.
- 제1항에 있어서, Ar이 치환 또는 비치환된 벤젠고리임을 특징으로 하는 화합물.
- 제2항에 있어서, R1X 및 인산염 치환기들의 서로 파라배열을 갖는 것을 특징으로 하는 화합물.
- 제1항에 있어서, Ar이 치환된 방향족 핵이어서 화합물(Ⅰ)의 독성에 잘 견디는 대응하는 페놀 R1XArOH로 쉽게 가수분해되는 것을 특징으로 하는 화합물.
- 제1항에 있어서, A는 같거나 다를 수 있는 하나 이상의 치환기를 (예로서, 할로겐원자, 플루오로알킬, 알콕시, 플루오로알콕시, 카르보알콕시, 아미노 또는 아미도기)에 의해 치환된 벤젠기임을 특징으로 하는 화합물.
- 제1항에 있어서, X는 술포닐기임을 특징으로 하는 화합물.
- 제1 내지 제6항중 어느 한항에 있어서, R2및 R3는 각각 일반식(a), (b), (d) 또는 (f)의 부분임을 특징으로 하는 화합물.
- 제7항에 있어서, R2및 R3가 각각 일반식(f)의 부분임을 특징으로 하는 화합물.
- 제7항에 있어서, R2및 R3가 각각 하기 일반식(ⅰ) 내지 (x)중 어느 하나임을 특징으로 하는 화합물;
- 제9항에 있어서, R2및 R3가 각각 일반식(i), (v), (vi) 또는 (ix)임을 특징으로 하는 화합물.
- 4-(메틸술포닐)페닐 비스(3´-이지도 티미딘-5´-일)인산염.
- 4-(메틸술포닐)페닐 비스(2´, 3´-디데히드로-2´, 3´-디데옥시시티딘-5´-일)인산염
- 4-(메틸술포닐)페닐 비스(2´, 3´-디데히드로-2´, 3´-디데옥시시티딘-5´-일)인산염
- 4-(메틸술포닐)페닐 비스(2´, 3´-디데옥시아데노신-5´-일)인산염
- 4-(메틸술포닐)페닐 비스(2´, 3´-디데히드로-2´, 3´-디데옥시 티미딘-5´-일)인산염
- 하기 일반식(Ⅲ)의 포스포로디할로겐화물을 일반식(Ⅱ)의 화합물 또는 R2의 뉴클레오시드염기 내 그룹이 보호된 유도체와 반응시키는 것으로 이루어진 일반식(Ⅰ)의 화합물의 제조방법;R1XArOP(O)Y2(Ⅲ)R2OH (Ⅱ)상기식에서, R1, R2, Ar 및 X는 제1항에 기재된 바와같고, Y는 할로겐원자이다.
- 제16항에 있어서, R2내 뉴클레오시드 염기가 아실화에 의해 보호된 시토신임을 특징으로 하는 방법.
- 제16 또는 17항에 있어서, 반응이 염기 존재하에 수행되는 것을 특징으로 하는 화합물.
- 제18항에 있어서, 염기가 1-메틸이미다졸임을 특징으로 하는 화합물.
- R1, Ar, R2및 R3기 제1항에 기재된 바와같은 일반식(Ⅳ): R1SArOP(O)(OR2)(OR3) 또는 일반식(Ⅴ): R1SOArOP(O)(OR2)(OR3)의 화합물을 산화시키는 것을 특징으로 하는, 일반식(Ⅰ)의 화합물의 제조방법.
- 제20항에 있어서, 산화가 과(per)산에 의해 수행되는 것을 특징으로 하는 방법.
- 일반식(Ⅳ)의 중간체.
- 일반식(Ⅴ)의 중간체.
- 치료에 사용하기 위한 일반식(Ⅰ)의 화합물.
- 사람의 레트로바이러스감염의 치료 또는 예방에 유용한 의약을 제조하기 위한 일반식(Ⅰ)의 화합물 사용.
- 아이러스복제를 억제 또는 방해하는데에 유효량의 일반식(Ⅰ)의 화합물을 바이러스로 감염된 객체에 투여하는 것으로 이루어진 사람의 레트로 바이러스 감염의 치료 또는 예방방법.
- 바이러스복제를 억제 또는 방해하는 데에 유효량의 일반식(Ⅰ)의 화합물을 가지고서 바이러스로 감염된 혈액을 치료하는 것으로 이루어진 사람의 레트로바이러스감염의 치료 또는 예방방법.
- 제26 또는 27항에 있어서, 바이러스가 사람의 면역결핍 바이러스(HIV)임을 특징으로 하는 방법.
- 일반식(Ⅰ)의 화합물과 함께 약리학적으로 허용 가능한 이들의 담체를 포함하는 것으로 이루어진, 사람의 레트로바이러스감염의 치료 또는 예방용 제제.
- 투여 형태로서의 제29항에 따른 제제.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB898908355A GB8908355D0 (en) | 1988-04-18 | 1989-04-13 | Output apparatus antiviral compounds |
GB89083554 | 1989-04-13 | ||
PCT/GB1990/000542 WO1990012023A1 (en) | 1989-04-13 | 1990-04-10 | Antiviral compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
KR920700217A true KR920700217A (ko) | 1992-02-19 |
Family
ID=10654960
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019900702612A KR920700217A (ko) | 1989-04-13 | 1990-04-10 | 항 바이러스성 화합물 |
Country Status (16)
Country | Link |
---|---|
EP (1) | EP0392791B1 (ko) |
JP (1) | JPH03505880A (ko) |
KR (1) | KR920700217A (ko) |
CN (1) | CN1046531A (ko) |
AT (1) | ATE125817T1 (ko) |
AU (1) | AU5407890A (ko) |
CA (1) | CA2028151A1 (ko) |
DE (1) | DE69021242T2 (ko) |
ES (1) | ES2077643T3 (ko) |
FI (1) | FI906113A0 (ko) |
GB (1) | GB2230266B (ko) |
NZ (1) | NZ233197A (ko) |
OA (1) | OA09553A (ko) |
PT (1) | PT93743A (ko) |
WO (1) | WO1990012023A1 (ko) |
ZA (1) | ZA902784B (ko) |
Families Citing this family (38)
Publication number | Priority date | Publication date | Assignee | Title |
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US6903224B2 (en) | 1988-04-11 | 2005-06-07 | Biochem Pharma Inc. | Substituted 1,3-oxathiolanes |
US5270315A (en) * | 1988-04-11 | 1993-12-14 | Biochem Pharma Inc. | 4-(purinyl bases)-substituted-1,3-dioxlanes |
US6350753B1 (en) | 1988-04-11 | 2002-02-26 | Biochem Pharma Inc. | 2-Substituted-4-substituted-1,3-dioxolanes and use thereof |
US7119202B1 (en) | 1989-02-08 | 2006-10-10 | Glaxo Wellcome Inc. | Substituted-1,3-oxathiolanes and substituted-1,3-dioxolanes with antiviral properties |
UA45942A (uk) * | 1989-02-08 | 2002-05-15 | Біокем Фарма, Інк. | 1,3-оксатіолан, його похідні, спосіб (варіанти) його одержання та фармацевтична композиція |
MY104575A (en) * | 1989-12-22 | 1994-04-30 | The Wellcome Foundation Ltd | Therapeutic nucleosides. |
US5276151A (en) * | 1990-02-01 | 1994-01-04 | Emory University | Method of synthesis of 1,3-dioxolane nucleosides |
US5914331A (en) | 1990-02-01 | 1999-06-22 | Emory University | Antiviral activity and resolution of 2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane |
US6703396B1 (en) | 1990-02-01 | 2004-03-09 | Emory University | Method of resolution and antiviral activity of 1,3-oxathiolane nuclesoside enantiomers |
US6346627B1 (en) | 1990-02-01 | 2002-02-12 | Emory University | Intermediates in the synthesis of 1,3-oxathiolane nucleoside enantiomers |
US5204466A (en) * | 1990-02-01 | 1993-04-20 | Emory University | Method and compositions for the synthesis of bch-189 and related compounds |
GB9009861D0 (en) | 1990-05-02 | 1990-06-27 | Glaxo Group Ltd | Chemical compounds |
US6228860B1 (en) | 1990-11-13 | 2001-05-08 | Biochem Pharma Inc. | Substituted 1,3-oxathiolanes with antiviral properties |
US6369066B1 (en) | 1990-11-13 | 2002-04-09 | Biochem Pharma, Inc. | Substituted 1,3-oxathiolanes with antiviral properties |
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US5925643A (en) * | 1990-12-05 | 1999-07-20 | Emory University | Enantiomerically pure β-D-dioxolane-nucleosides |
US5444063A (en) * | 1990-12-05 | 1995-08-22 | Emory University | Enantiomerically pure β-D-dioxolane nucleosides with selective anti-Hepatitis B virus activity |
AU1254892A (en) * | 1990-12-18 | 1992-07-22 | Sloan-Kettering Institute For Cancer Research | Novel synthesis of 2'-"up" fluorinated 2''-deoxy-arabinofuranosylpurines |
IL100502A (en) * | 1991-01-03 | 1995-12-08 | Iaf Biochem Int | PHARMACEUTICAL PREPARATIONS CONTAINING CIS-4-AMINO-1-) 2-HYDROXIMETHIL-1,3-OXETYOLEN-5-IL (- |
US6812233B1 (en) | 1991-03-06 | 2004-11-02 | Emory University | Therapeutic nucleosides |
US5817667A (en) * | 1991-04-17 | 1998-10-06 | University Of Georgia Research Foudation | Compounds and methods for the treatment of cancer |
GB9110874D0 (en) * | 1991-05-20 | 1991-07-10 | Iaf Biochem Int | Medicaments |
ZA923641B (en) * | 1991-05-21 | 1993-02-24 | Iaf Biochem Int | Processes for the diastereoselective synthesis of nucleosides |
FR2685331A1 (fr) * | 1991-12-12 | 1993-06-25 | Centre Nat Rech Scient | Phosphotriesters de la ddu, leur preparation et leur application en therapeutique. |
CA2129986C (en) * | 1992-02-13 | 2003-12-09 | Albert Reto Schwendener | Amphiphile nucleosidphosphatanaloga |
GB9226879D0 (en) * | 1992-12-23 | 1993-02-17 | Iaf Biochem Int | Anti-viral compounds |
US6005107A (en) | 1992-12-23 | 1999-12-21 | Biochem Pharma, Inc. | Antiviral compounds |
US6444656B1 (en) | 1992-12-23 | 2002-09-03 | Biochem Pharma, Inc. | Antiviral phosphonate nucleotides |
US20020120130A1 (en) | 1993-09-10 | 2002-08-29 | Gilles Gosselin | 2' or 3' -deoxy and 2', 3' -dideoxy-beta-L-pentofuranonucleo-side compounds, method of preparation and application in therapy, especially as anti- viral agents |
US5587362A (en) * | 1994-01-28 | 1996-12-24 | Univ. Of Ga Research Foundation | L-nucleosides |
WO1996002554A1 (en) * | 1994-07-15 | 1996-02-01 | Gruppo Lepetit S.P.A. | Dinucleoside-5',5'-pyrophosphates |
IL115156A (en) | 1994-09-06 | 2000-07-16 | Univ Georgia | Pharmaceutical compositions for the treatment of cancer comprising 1-(2-hydroxymethyl-1,3-dioxolan-4-yl) cytosines |
US5703058A (en) * | 1995-01-27 | 1997-12-30 | Emory University | Compositions containing 5-fluoro-2',3'-didehydro-2',3'-dideoxycytidine or a mono-, di-, or triphosphate thereof and a second antiviral agent |
US6391859B1 (en) | 1995-01-27 | 2002-05-21 | Emory University | [5-Carboxamido or 5-fluoro]-[2′,3′-unsaturated or 3′-modified]-pyrimidine nucleosides |
US5808040A (en) * | 1995-01-30 | 1998-09-15 | Yale University | L-nucleosides incorporated into polymeric structure for stabilization of oligonucleotides |
DE69636734T2 (de) | 1995-06-07 | 2007-10-18 | Emory University | Nucleoside mit anti-hepatitis b virus wirksamkeit |
US5753789A (en) * | 1996-07-26 | 1998-05-19 | Yale University | Oligonucleotides containing L-nucleosides |
AU6551800A (en) * | 1999-08-17 | 2001-03-13 | Adani, Alexander | Dinucleoside 5',5'-tetraphosphates as inhibitors of viral reverse transcriptasesand viruses |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA931561A (en) * | 1969-03-10 | 1973-08-07 | Syntex Corporation | Nucleoside phosphonates, phosphonic acids, phosphonic acid salts, and process for producing same |
CA1330794C (en) * | 1987-03-27 | 1994-07-19 | Phillip Frost | Anti-viral compounds, dosage forms and methods |
-
1990
- 1990-04-04 NZ NZ233197A patent/NZ233197A/xx unknown
- 1990-04-10 AT AT90303818T patent/ATE125817T1/de not_active IP Right Cessation
- 1990-04-10 ES ES90303818T patent/ES2077643T3/es not_active Expired - Lifetime
- 1990-04-10 EP EP90303818A patent/EP0392791B1/en not_active Expired - Lifetime
- 1990-04-10 AU AU54078/90A patent/AU5407890A/en not_active Abandoned
- 1990-04-10 CA CA002028151A patent/CA2028151A1/en not_active Abandoned
- 1990-04-10 WO PCT/GB1990/000542 patent/WO1990012023A1/en active Application Filing
- 1990-04-10 JP JP2505653A patent/JPH03505880A/ja active Pending
- 1990-04-10 KR KR1019900702612A patent/KR920700217A/ko not_active Application Discontinuation
- 1990-04-10 GB GB9008105A patent/GB2230266B/en not_active Expired - Lifetime
- 1990-04-10 DE DE69021242T patent/DE69021242T2/de not_active Expired - Fee Related
- 1990-04-11 ZA ZA902784A patent/ZA902784B/xx unknown
- 1990-04-11 PT PT93743A patent/PT93743A/pt not_active Application Discontinuation
- 1990-04-13 CN CN90103632A patent/CN1046531A/zh active Pending
- 1990-11-15 OA OA59895A patent/OA09553A/en unknown
- 1990-12-12 FI FI906113A patent/FI906113A0/fi not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
GB2230266A (en) | 1990-10-17 |
GB2230266B (en) | 1992-08-12 |
EP0392791B1 (en) | 1995-08-02 |
FI906113A0 (fi) | 1990-12-12 |
DE69021242T2 (de) | 1996-01-11 |
NZ233197A (en) | 1991-11-26 |
WO1990012023A1 (en) | 1990-10-18 |
CN1046531A (zh) | 1990-10-31 |
ES2077643T3 (es) | 1995-12-01 |
AU5407890A (en) | 1990-11-05 |
JPH03505880A (ja) | 1991-12-19 |
OA09553A (en) | 1993-01-31 |
ATE125817T1 (de) | 1995-08-15 |
EP0392791A1 (en) | 1990-10-17 |
DE69021242D1 (de) | 1995-09-07 |
GB9008105D0 (en) | 1990-06-06 |
ZA902784B (en) | 1991-12-24 |
CA2028151A1 (en) | 1990-10-14 |
PT93743A (pt) | 1990-11-20 |
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