KR920702684A - 신규의 메틸렌비스포스폰산 유도체 - Google Patents
신규의 메틸렌비스포스폰산 유도체Info
- Publication number
- KR920702684A KR920702684A KR1019910701935A KR910701935A KR920702684A KR 920702684 A KR920702684 A KR 920702684A KR 1019910701935 A KR1019910701935 A KR 1019910701935A KR 910701935 A KR910701935 A KR 910701935A KR 920702684 A KR920702684 A KR 920702684A
- Authority
- KR
- South Korea
- Prior art keywords
- hydrogen
- formula
- groups
- compound
- bisphosphonic acid
- Prior art date
Links
- MBKDYNNUVRNNRF-UHFFFAOYSA-N medronic acid Chemical class OP(O)(=O)CP(O)(O)=O MBKDYNNUVRNNRF-UHFFFAOYSA-N 0.000 title claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 22
- 239000001257 hydrogen Substances 0.000 claims abstract 22
- 150000001875 compounds Chemical class 0.000 claims abstract 16
- 239000002253 acid Substances 0.000 claims abstract 8
- 150000003839 salts Chemical class 0.000 claims abstract 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 5
- 239000000460 chlorine Chemical group 0.000 claims abstract 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract 4
- 229910052794 bromium Inorganic materials 0.000 claims abstract 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 2
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 2
- 239000011737 fluorine Chemical group 0.000 claims abstract 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims abstract 2
- 150000002431 hydrogen Chemical class 0.000 claims 8
- -1 monoethyl ester Chemical class 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 229910052736 halogen Chemical group 0.000 claims 4
- 150000002367 halogens Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 238000005886 esterification reaction Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 150000005691 triesters Chemical class 0.000 claims 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 2
- 239000012042 active reagent Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 239000011630 iodine Substances 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 claims 1
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 claims 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- ACSIXWWBWUQEHA-UHFFFAOYSA-N clodronic acid Chemical compound OP(O)(=O)C(Cl)(Cl)P(O)(O)=O ACSIXWWBWUQEHA-UHFFFAOYSA-N 0.000 claims 1
- 238000005695 dehalogenation reaction Methods 0.000 claims 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical group BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 claims 1
- 150000005690 diesters Chemical class 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 1
- SQQWBSBBCSFQGC-JLHYYAGUSA-N ubiquinone-2 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(C)C1=O SQQWBSBBCSFQGC-JLHYYAGUSA-N 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
Classifications
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4025—Esters of poly(thio)phosphonic acids
- C07F9/4037—Esters of poly(thio)phosphonic acids containing halogen or nitro(so) substituents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4081—Esters with cycloaliphatic alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Detergent Compositions (AREA)
- Paints Or Removers (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Breeding Of Plants And Reproduction By Means Of Culturing (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (11)
- 다음 일반식(I)의 신규의 비스포스폰산 유도체, 그 화합물의 입체이성체, 이를테면 기하이성체 및 광학 활성이성체, 그 외에 그 화합물의 약리적으로 허용되는 염에 관한 것이다.상기식에서, R1, R2, R3및 R4는 각각 C1-C22-알킬, C2-C22-알켄일, C2-C22-알킨일, C3-C10-시클로알킬, C2-C10-시클로알켄일, 아릴, 아르알킬, 실릴 또는 수소이며, 따라서, 일반식(I)에서 R1,R2,R3및 R4기중 적어도 한가지는 수소이며 R1,R2,R3및 R4기중 적어도 한가지는 수소가 아니며, Q1은 수소, 불소, 염소, 브롬 또는 요오드이며, Q2은 염소, 브롬 또는 요오드이다.
- 제1항에 있어서, Q1및 Q2가 염소인 일반식(I)의 비스포스폰산 유도체.
- 제1항에 있어서, R1-R4기중 한가지가 수소가 아니며 나머지가 수소인 일반식(I)의 화합물.
- 제2항에 있어서, R1-R4기중 한가지가 수소이며, R1-R4기중 한가지가 저급알킬이며 나머지가 수소 또는 저급알킬, 바람직하게는 메틸 또는 에틸인 일반식(I)의 화합물.
- 제4항에 있어서, R1-R4기중 한가지 또는 두가지가 저급알킬, 바람직하게는 메틸 또는에틸인 일반식(I)의 화합물.
- 제5항에 있어서, (디클로로메틸렌)비스포스폰산의 모노메틸 또는 모노에틸에스테르인 일반식(I)의 화합물.
- 제2항에 있어서, R1-R4기중 한가지 또는 두가지가 C14-C18-알킬 또는 -알켄일이고 나머지가 수소인 일반식(I)의 화합물.
- 제1항에 따른 일반식(I)의 (플루오로클로로-, 브로모클로로- 및 디브로모메틸렌)비스포스폰산 모노메틸- 및 모노에틸 에스테르.
- a) 다음 일반식(II)의 메틸렌비스포스폰산 테트라에스테르를 선택적 가수분해반응시켜 R1,R2,R3및 R4기중 한가지가 수소를 의미하는 상응하는 트리에스테르(III), 또는 그의 염을 형성하거나, 또는 R1,R2,R3및 R4기중 두가지가 수소를 의미하는 상응하는 디에스테르(IV 및/또는 V), 또는 그의 염을 형성하거나, 또는 R1,R2,R3및 R4기중 세가지가 수소를 의미하는 상응하는 모노에스테르(VI), 또는 그의 염을 형성하거나, 또는(상기식에서, Q1및 Q2는 제1항에서와 동일한 의미를 가지며, R1,R2,R3및 R4기는 수소를 제외하고 제1항에서와 동일한 의미를 가진다)b) 다음 일반식(VII)의 비스포스폰산 또는 그의 금속 또는 암모늄염, 또는 상응하는 산 테트라클로라이드를 필요로한 R1-R4기에 상응하는 에스테르화제와 반응시킴으로서 선택 에스테르화 반응시켜 R1,R2,R3및 R4기중 한가지가 수소를 의미하는 상응하는 트리에스테르(III), 또는 그의 염을 형성하거나, 또는 R1,R2,R3및 R4기중 두가지가 수소를 의미하는 상응하는 디에스테르(IV 및/또는 V), 또는 그의 염을 형성하거나, 또는 R1,R2,R3및 R4기중 세가지가 수소를 의미하는 상응하는 모노에스테르(VI) 또는 그의 염을 형성하거나, 또는(상기식에서 Q1및 Q2는 제1항에서와 동일한 의미를 가진다) c) 다음 일반식(IX)을 가진 포스포네이트를 활성화된 포스페인트와 반응시키거나, 또는 일반식(X)에 따른 수소 포스포네이트를 일반식(X)에 상응하는 포스파이트와 반응시키거나, 또는(상기식에서 Y는 수소 또는 할로겐, 또는 다른 이탈기이며, Z는 수소, 할로겐, 아릴록시, 술포닐록시, 또는 알콕시이며, R1-R4및 Q1,Q2는 일반식(I)에서와 동일한 의미를 가진다) d) 다음 일반식(XI)의 비스포스포나이트 화합물, 또는 상응하는 수소포스포에니트 화합물을 일반식(I)의 화합물로 산화시키거나, 또는(상기식에서 R1-R4및 Q1,Q2는 일반식(I)에서와 동일한 의미를 가진다)e) 다음 일반식(XV)의 메틸렌비스포스포네이트를 할로겐화하고,(상기식에서 R1-R4는 제1항에서와 동일한 의미를 가진다) 필요하다면 방법 a)-e)에서 상기에 얻어진 부분 에스테르산을 부분 에스트르염을 전환시키거나, 또는 부분에스테르염을 부분에스테르산으로 전환시키고, 그리고/또는, 필요하다면 일반식(I)에 따라 얻어진 화합물을 예를들어 가수분해 반응, 에스테르화 반응, 제에스테르화 반응, 메틸렌수소를 할로겐화시키는 것, 다할로겐 치환메틸렌기를 모노-탈할로겐화시키는 것, 또는 정의의 범위내에서 할로겐을 또다른 할로겐에 대하여 교환시키는 것에 의하여 일반식(I)에 따른 또다른 화합물로 전환시키는 것이 특징인 제1항에 따른 화합물의 제조방법.
- 약리적으로 활성인 시약으로서 제1항에 따른 일반식(I)의 화합물로 이루어진 것이 특징인 약제조성물.
- 치료활성시약으로서 제1항에 따른 일반식(I)화합물의 용도.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI893039 | 1989-06-21 | ||
| FI893039A FI83421C (fi) | 1989-06-21 | 1989-06-21 | Foerfarande foer framstaellning av farmakologiskt anvaendbara metylenbisfosfonsyraderivat. |
| PCT/FI1990/000163 WO1990015806A1 (en) | 1989-06-21 | 1990-06-19 | Novel methylenebisphosphonic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR920702684A true KR920702684A (ko) | 1992-10-06 |
Family
ID=8528656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019910701935A KR920702684A (ko) | 1989-06-21 | 1990-06-19 | 신규의 메틸렌비스포스폰산 유도체 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5376649A (ko) |
| EP (1) | EP0479813B1 (ko) |
| JP (1) | JP2929236B2 (ko) |
| KR (1) | KR920702684A (ko) |
| AT (1) | ATE128139T1 (ko) |
| CA (1) | CA2062735C (ko) |
| DE (1) | DE69022593T2 (ko) |
| ES (1) | ES2078970T3 (ko) |
| FI (1) | FI83421C (ko) |
| HK (1) | HK26096A (ko) |
| HU (2) | HU208701B (ko) |
| NO (1) | NO178030C (ko) |
| NZ (1) | NZ234179A (ko) |
| RU (1) | RU2074860C1 (ko) |
| WO (1) | WO1990015806A1 (ko) |
| ZA (1) | ZA904828B (ko) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6458772B1 (en) * | 1909-10-07 | 2002-10-01 | Medivir Ab | Prodrugs |
| NZ254765A (en) † | 1993-05-15 | 1997-02-24 | Boehringer Mannheim Gmbh | Tablet medicament; comprises dichloromethylene diphosphonic acid (clodronic acid) or a pharmaceutically acceptable salt thereof as active ingredient and microcrystalline cellulose as auxiliary |
| US5462932A (en) * | 1994-05-17 | 1995-10-31 | Merck & Co., Inc. | Oral liquid alendronate formulations |
| FR2721929B1 (fr) * | 1994-06-30 | 1996-12-20 | Centre Nat Rech Scient | Analogues stables, non hydrolysables, de diphosphates et leurs procedes de preparation |
| US5652227A (en) * | 1995-01-30 | 1997-07-29 | Teronen; Olli Pekka | Inhibition of the degradation of connective tissue matrix protein components in mammals |
| FI104901B (fi) | 1997-10-20 | 2000-04-28 | Leiras Oy | Uudet metyleenibisfosfonihappojohdannaiset |
| US20020128301A1 (en) * | 1998-02-13 | 2002-09-12 | Medivir AB | Non-nucleoside reverse transcriptase inhibitors |
| SE9903345D0 (sv) * | 1999-09-17 | 1999-09-17 | Astra Pharma Prod | Novel process |
| ATE385797T1 (de) * | 1999-12-03 | 2008-03-15 | Univ California At San Diego | Phosphonatverbindungen |
| US7862552B2 (en) | 2005-05-09 | 2011-01-04 | Boston Scientific Scimed, Inc. | Medical devices for treating urological and uterine conditions |
| NZ578296A (en) * | 2007-01-26 | 2012-07-27 | Kaneq Pharma Inc | Fused aromatic ptp-1b inhibitors |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3303139A (en) * | 1962-01-27 | 1967-02-07 | Henkel & Cie Gmbh | Aminophosphonic acids and their derivatives as complex formers for metal ions |
| SE350402B (ko) * | 1965-12-08 | 1972-10-30 | Procter & Gamble | |
| DE1617118C3 (de) * | 1966-08-26 | 1975-04-03 | Henkel & Cie Gmbh, 4000 Duesseldorf | Verfahren zur Reinigung von etikettierten starren Gegenständen |
| US3962318A (en) * | 1970-04-13 | 1976-06-08 | Monsanto Company | Substituted ethane diphosphonic acids and salts and esters thereof |
| US3957858A (en) * | 1970-04-13 | 1976-05-18 | Monsanto Company | Substituted ethane diphosphonic acids and salts and esters thereof |
| US3683080A (en) * | 1970-08-28 | 1972-08-08 | Procter & Gamble | Compositions for inhibiting anomalous deposition and mobilization of calcium phosphate in animal tissue |
| DE2813121A1 (de) * | 1977-03-29 | 1978-10-12 | Procter & Gamble | Verwendung von dichlormethan-diphosphonatverbindungen bei der bekaempfung von collagen-erkrankungen und zur wundheilung |
| US4634691A (en) * | 1980-10-07 | 1987-01-06 | The Procter & Gamble Company | Method for inhibiting tumor metastasis |
| US4478763A (en) | 1982-10-20 | 1984-10-23 | Univ. Of Southern California | Process for preparing alpha-fluorinated alkanediphosphonates |
| GB8419489D0 (en) * | 1984-07-31 | 1984-09-05 | Leo Pharm Prod Ltd | Chemical compounds |
| IL77243A (en) * | 1984-12-21 | 1996-11-14 | Procter & Gamble | Pharmaceutical compositions containing geminal diphosphonic acid compounds and certain such novel compounds |
| EP0356866A3 (en) * | 1988-08-29 | 1991-03-27 | E.R. SQUIBB & SONS, INC. | Phosphorus-containing squalene synthetase inhibitors and method |
-
1989
- 1989-06-21 FI FI893039A patent/FI83421C/fi active IP Right Grant
-
1990
- 1990-06-19 RU SU905010886A patent/RU2074860C1/ru not_active IP Right Cessation
- 1990-06-19 ES ES90909051T patent/ES2078970T3/es not_active Expired - Lifetime
- 1990-06-19 CA CA002062735A patent/CA2062735C/en not_active Expired - Fee Related
- 1990-06-19 WO PCT/FI1990/000163 patent/WO1990015806A1/en active IP Right Grant
- 1990-06-19 KR KR1019910701935A patent/KR920702684A/ko not_active Application Discontinuation
- 1990-06-19 US US07/777,555 patent/US5376649A/en not_active Expired - Lifetime
- 1990-06-19 EP EP90909051A patent/EP0479813B1/en not_active Expired - Lifetime
- 1990-06-19 AT AT90909051T patent/ATE128139T1/de not_active IP Right Cessation
- 1990-06-19 DE DE69022593T patent/DE69022593T2/de not_active Expired - Fee Related
- 1990-06-19 JP JP2508624A patent/JP2929236B2/ja not_active Expired - Fee Related
- 1990-06-19 HU HU904623A patent/HU208701B/hu not_active IP Right Cessation
- 1990-06-21 ZA ZA904828A patent/ZA904828B/xx unknown
- 1990-06-21 NZ NZ234179A patent/NZ234179A/en unknown
-
1991
- 1991-12-19 NO NO915021A patent/NO178030C/no not_active IP Right Cessation
-
1995
- 1995-06-15 HU HU95P/P00212P patent/HU211204A9/hu unknown
-
1996
- 1996-02-08 HK HK26096A patent/HK26096A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU5827290A (en) | 1991-01-08 |
| DE69022593D1 (de) | 1995-10-26 |
| WO1990015806A1 (en) | 1990-12-27 |
| HU208701B (en) | 1993-12-28 |
| HU904623D0 (en) | 1992-06-29 |
| FI83421C (fi) | 1991-07-10 |
| FI893039A (fi) | 1990-12-22 |
| DE69022593T2 (de) | 1996-06-13 |
| JPH05500208A (ja) | 1993-01-21 |
| HU211204A9 (en) | 1995-11-28 |
| ES2078970T3 (es) | 1996-01-01 |
| NO178030C (no) | 1996-01-10 |
| ZA904828B (en) | 1991-03-27 |
| JP2929236B2 (ja) | 1999-08-03 |
| HK26096A (en) | 1996-02-16 |
| ATE128139T1 (de) | 1995-10-15 |
| CA2062735A1 (en) | 1990-12-22 |
| EP0479813B1 (en) | 1995-09-20 |
| CA2062735C (en) | 2000-08-15 |
| FI893039A0 (fi) | 1989-06-21 |
| RU2074860C1 (ru) | 1997-03-10 |
| NZ234179A (en) | 1991-12-23 |
| AU633459B2 (en) | 1993-01-28 |
| FI83421B (fi) | 1991-03-28 |
| EP0479813A1 (en) | 1992-04-15 |
| US5376649A (en) | 1994-12-27 |
| NO915021L (no) | 1991-12-19 |
| NO915021D0 (no) | 1991-12-19 |
| NO178030B (no) | 1995-10-02 |
| HUT62008A (en) | 1993-03-29 |
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| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |