KR930002364A - 골다공증 치료에 유용한 트리플루오로 메틸벤질 포스포네이트 - Google Patents
골다공증 치료에 유용한 트리플루오로 메틸벤질 포스포네이트 Download PDFInfo
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- KR930002364A KR930002364A KR1019920012631A KR920012631A KR930002364A KR 930002364 A KR930002364 A KR 930002364A KR 1019920012631 A KR1019920012631 A KR 1019920012631A KR 920012631 A KR920012631 A KR 920012631A KR 930002364 A KR930002364 A KR 930002364A
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- aralkyl
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- 208000001132 Osteoporosis Diseases 0.000 title claims 3
- 125000006493 trifluoromethyl benzyl group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims 8
- 125000004103 aminoalkyl group Chemical group 0.000 claims 7
- -1 piperidino, morpholino, thiomorpholino, piperazino, tetrahydroisoquinolinyl Chemical group 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 241000124008 Mammalia Species 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 3
- JRANUXHJUGOHIM-UHFFFAOYSA-N 1-(diethoxyphosphorylmethyl)-3-(trifluoromethyl)benzene Chemical compound CCOP(=O)(OCC)CC1=CC=CC(C(F)(F)F)=C1 JRANUXHJUGOHIM-UHFFFAOYSA-N 0.000 claims 2
- TVXYXFHWFHNWTJ-UHFFFAOYSA-N [3-(trifluoromethyl)phenyl]methylphosphonic acid Chemical compound OP(O)(=O)CC1=CC=CC(C(F)(F)F)=C1 TVXYXFHWFHNWTJ-UHFFFAOYSA-N 0.000 claims 2
- VYEUMHFHYLKSOA-UHFFFAOYSA-N ethoxy-[[3-(trifluoromethyl)phenyl]methyl]phosphinic acid Chemical compound CCOP(O)(=O)CC1=CC=CC(C(F)(F)F)=C1 VYEUMHFHYLKSOA-UHFFFAOYSA-N 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 2
- WRCZXALKTFNFPN-UHFFFAOYSA-N 1-[[ethoxy(3-phenylpropoxy)phosphoryl]methyl]-3-(trifluoromethyl)benzene Chemical compound C=1C=CC=CC=1CCCOP(=O)(OCC)CC1=CC=CC(C(F)(F)F)=C1 WRCZXALKTFNFPN-UHFFFAOYSA-N 0.000 claims 1
- YOPGFVQSFXWVHU-UHFFFAOYSA-N 2-[ethoxy-[[3-(trifluoromethyl)phenyl]methyl]phosphoryl]oxy-n,n-diethylethanamine Chemical compound CCN(CC)CCOP(=O)(OCC)CC1=CC=CC(C(F)(F)F)=C1 YOPGFVQSFXWVHU-UHFFFAOYSA-N 0.000 claims 1
- NVZRFUCVCIVKJR-UHFFFAOYSA-M benzyl(methoxy)phosphinate Chemical compound COP([O-])(=O)CC1=CC=CC=C1 NVZRFUCVCIVKJR-UHFFFAOYSA-M 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/6533—Six-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- 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)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3882—Arylalkanephosphonic acids
-
- 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
- C07F9/4056—Esters of arylalkanephosphonic acids
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- 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)
- Physical Education & Sports Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (13)
- 일반식(I)의 화합물 및 그의 약제학적으로 허용되는 염.상기 식에서, R1및 R2는 동일하거나 상이하며, 수소, 알킬, 알케닐, 히드록시알킬, 알콕시알킬, 아르알킬, 아릴 및 아미노알킬중에서 선택되고; R3및 R5는 각각이 H이거나 CF3일 수 있으나, 단 R3및 R5중의 단지 하나만 이 CF3일 수 있으며; R4및 R6는 각각 H 또는 CF3일 수 있으며, 단 R4및 R6중의 어느 하나 또는 둘다가 CF3이며, R3및 R5중의 어느것도 CF3일 수 없으며, 또한 R3내지 R6가 동시에 모두 H일 수는 없고, R4및 R6가 각각 CF3일 경우에만 R1및 R2는 모두 에틸일 수 있다.
- 제1항에 있어서, 아미노알킬이 -(CH2)n-NR7R8이며, 여기에서 n은 2 내지 6이고 R7및 R8은 동일하거나 상이하며 H, 알킬 및 아르알킬중에서 선택되거나, R7및 R8은 함께 결합하여 N, O 및 S중에서 선택된 하나이상의 헤테로 원자를 함유하는 헤테로 사이클 환을 형성하는 화합물.
- 제2항에 있어서, 헤테로사이클 환이 피페리디노, 모폴리노, 티오모폴리노, 피페라지노, 테트라히드로이소퀴놀리닐, 테트라이드로퀴놀리닐, 및 아르알킬 및 페닐중의 어느 하나에 의해 말단 N-4 위치에서 치환되는 치환된 피페라지노중에서 선택된 화합물.
- 제1항에 있어서, 3-트리플루오로메틸벤질포스폰산, 에틸 3-트리플루오로메틸벤질포스폰산, 알릴 에틸 3-트리플루오로메틸벤질 포스포네이트, 디에틸아미노에틸 에틸 3-트리플루오로메틸벤질포스포네이트 및 에틸 3-페닐프로필 3-트리플루오로메틸벤질포스포네이트중에서 선택되는 화합물.
- 치료학적 유효량의 일반식(I)의 화합물 및 약제학적으로 허용되는 담체를 함유하는 약제학적 조성물.상기 식에서, R1및 R2는 동일하거나 상이하며, 수소, 알킬, 알케닐, 히드록시알킬, 알콕시알킬, 아르알킬, 아릴 및 아미노알킬중에서 선택되고; R3및 R5는 각각이 H이거나 CF3일 수 있으나, 단 R3및 R5중의 단지 하나만 이 CF3일 수 있으며; R4및 R6는 각각 H 또는 CF3일 수 있으며, 단 R4및 R6중의 어느 하나 또는 둘다가 CF3이며, R3및 R5중의 어느것도 CF3일 수 없으며, 또한 R3내지 R6가 동시에 모두 H일 수는 없다.
- 제5항에 있어서, 아미노알킬이 -(CH2)n-NR7R8이며, 여기에서 n은 2 내지 6이고 R7및 R8은 동일하거나 상이하며 H, 알킬, 아미노알킬 및 아르알킬중에서 선택되거나, R7및 R8은 함께 결합하여 N, O 및 S중에서 선택된 하나이상의 헤테로 원자를 함유하는 헤테로 사이클 환을 형성하는 조성물.
- 제6항에 있어서, 헤테로사이클 환이 피페리디노, 모폴리노, 피페라지노, 테트라히드로이소퀴놀리닐, 테트라이드로퀴놀리닐, 및 아르알킬 및 페닐중의 어느 하나에 의해 말단 N-4 위치에서 치환되는 치환된 피페라지노중에서 선택되는 조성물.
- 제5항에 있어서, 화합물이 디에틸 3-트리플루오로메틸~ 벤질포스네이트, 3-트리플루오로메틸벤질포스폰 산, 에틸 3-트리-플루오로메틸벤질포스폰산, 아릴 에틸 3-트리플루오로메틸벤질-포스포네이트, 디에틸아미노에틸 에틸 3-트리플루오로메틸벤질- 포스포네이트 및 에틸 3-페닐프로필 3-트리플루오로메닐벤질포스포네이트중에서 선택되는 조성물.
- 유효량의 일반식(I)의 화합물 또는 그의 약제학적으로 허용되는 염을 포유동물에 투여함을 특징으로 하여 포유동물에서 골소모성 질환을 치료하는 방법.상기 식에서, R1및 R2는 동일하거나 상이하며, 수소, 알킬, 알케닐, 히드록시알킬, 알콕시알킬, 아르알킬, 아릴 및 아미노알킬중에서 선택되고; R3및 R5는 각각이 H이거나 CF3일 수 있으나, 단 R3및 R5중의 단지 하나만 이 CF3일 수 있으며; R4및 R6는 각각 H 또는 CF3일 수 있으며, 단 R4및 R6중의 어느 하나 또는 둘다가 CF3이며, R3및 R5중의 어느것도 CF3일 수 없으며, 또한 R3내지 R6가 동시에 모두 H일 수는 없다.
- 제9항에 있어서, 일반식(I)의 화합물이 디에틸 3-트리플루오로메틸벤질포스포네이트인 방법.
- 유효량의 일반식(I)의 화합물 또는 그이 약제학적으로 허용되는 염을 포유동물에게 투여함을 특징으로 하여 포유동물에서 골다공증을 치료하는 방법.상기 식에서, R1및 R2는 동일하거나 상이하며, 수소, 알킬, 알케닐, 히드록시알킬, 알콕시알킬, 아르알킬, 아릴 및 아미노알킬중에서 선택되고; R3및 R5는 각각이 H이거나 CF3일 수 있으나, 단 R3및 R5중의 단지 하나만이 CF3일 수 있으며; R4및 R6는 각각 H 또는 CF3일 수 있으며, 단 R4및 R6중의 어느 하나 또는 둘다가CF3이며, R3및 R5중의 어느것도 CF3일 수 없으며, 또한 R3내지 R6가 동시에 모두 H일 수는 없다.
- 제11항에 있어서, 일반식(I)의 화합물이 디에틸 3-트리플루오로메틸벤질포스포네이트인 방법.
- 제11항에 있어서, 일반식(I)의 화합물이 3-트리플루오로메틸 벤질포스포네이트인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US732,267 | 1991-07-18 | ||
| US07/732,267 US5300687A (en) | 1991-07-18 | 1991-07-18 | Trifluoromethylbenzylphosphonates useful in treating osteoporosis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR930002364A true KR930002364A (ko) | 1993-02-23 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019920012631A KR930002364A (ko) | 1991-07-18 | 1992-07-15 | 골다공증 치료에 유용한 트리플루오로 메틸벤질 포스포네이트 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US5300687A (ko) |
| EP (1) | EP0524023A1 (ko) |
| JP (1) | JPH05213977A (ko) |
| KR (1) | KR930002364A (ko) |
| CN (1) | CN1070408A (ko) |
| AU (1) | AU657146B2 (ko) |
| CA (1) | CA2074020A1 (ko) |
| FI (1) | FI923289A (ko) |
| HU (1) | HUT62907A (ko) |
| IE (1) | IE922341A1 (ko) |
| MX (1) | MX9204229A (ko) |
| NO (1) | NO922851L (ko) |
| TW (1) | TW216796B (ko) |
| ZA (1) | ZA925391B (ko) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5300687A (en) * | 1991-07-18 | 1994-04-05 | Ortho Pharmaceutical Corporation | Trifluoromethylbenzylphosphonates useful in treating osteoporosis |
| ZA941088B (en) * | 1993-02-19 | 1995-09-27 | Symphar Sa | Substituted ketophosphonates the processes for their preparation and pharmaceutical compositions containing them |
| ATE169924T1 (de) * | 1993-05-18 | 1998-09-15 | Takeda Chemical Industries Ltd | Benzopyran-derivate und ihre verwendung |
| CA2191980A1 (en) * | 1994-07-04 | 1996-01-18 | Takashi Sohda | Phosphonic acid compounds, their production and use |
| US5691153A (en) * | 1996-09-06 | 1997-11-25 | Creighton University | Genetic markers to detect high bone mass |
| US5922697A (en) * | 1996-10-02 | 1999-07-13 | Warner-Lambert Company | Compounds, compositions and methods for inhibiting the binding of proteins containing an SH2 domain to cognate phosphorylated proteins |
| US6566353B2 (en) * | 1996-12-30 | 2003-05-20 | Bone Care International, Inc. | Method of treating malignancy associated hypercalcemia using active vitamin D analogues |
| US20020128240A1 (en) * | 1996-12-30 | 2002-09-12 | Bone Care International, Inc. | Treatment of hyperproliferative diseases using active vitamin D analogues |
| EP0906759A1 (de) * | 1997-10-02 | 1999-04-07 | Roche Diagnostics GmbH | Neue Osteoblastenspezifische Mitogene: Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US6911553B1 (en) | 1997-10-02 | 2005-06-28 | Roche Diagnostics Gmbh | Osteoblast-specific mitogens and drugs containing such compounds |
| FR2771102B1 (fr) * | 1997-11-14 | 2000-12-15 | Biocoral Inc | Procede pour induire la differenciation osteoblastique de cellules de tissu adipeux extramedullaire humain |
| US6979728B2 (en) * | 1998-05-04 | 2005-12-27 | Baylor College Of Medicine | Articles of manufacture and methods for array based analysis of biological molecules |
| AU1525700A (en) | 1998-11-19 | 2000-06-05 | Board Of Trustees Of The University Of Arkansas, The | Increasing bone strength with selected bisphosphonates |
| US20020150887A1 (en) * | 2000-11-09 | 2002-10-17 | National Institute Of Advanced Industrial Science And Technology | Methods and nucleic acid probes for molecular genetic analysis of polluted environments and environmental samples |
| US20050032060A1 (en) * | 2001-08-31 | 2005-02-10 | Shishir Shah | Arrays comprising pre-labeled biological molecules and methods for making and using these arrays |
| US7439346B2 (en) * | 2001-10-12 | 2008-10-21 | Perkinelmer Las Inc. | Nucleic acids arrays and methods of use therefor |
| CA2463725A1 (en) | 2001-10-12 | 2003-11-06 | Spectral Genomics, Inc. | Compilations of nucleic acids and arrays and methods of using them |
| US6916621B2 (en) * | 2002-03-27 | 2005-07-12 | Spectral Genomics, Inc. | Methods for array-based comparitive binding assays |
| DE10259245A1 (de) | 2002-12-17 | 2004-07-01 | Merck Patent Gmbh | Derivate des Asimadolins mit kovalent gebundenen Säuren |
| MXPA05010871A (es) * | 2003-04-11 | 2005-11-25 | Barr Lab Inc | Metodos para administrar estrogenos y progestinas. |
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| US8821884B2 (en) * | 2004-07-27 | 2014-09-02 | The Regents Of The University Of California | Compositions and methods using MD-2 mutants and chimeric proteins |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2917533A (en) * | 1954-05-12 | 1959-12-15 | Virginia Carolina Chem Corp | Dialkylaminoalkyl esters of phosphonic acid and method of preparing same |
| US3363032A (en) * | 1964-06-11 | 1968-01-09 | Monsanto Co | Long chain aliphatic benzylphosphonic acids, esters and salts |
| DE3339383A1 (de) * | 1983-10-29 | 1985-05-09 | Bayer Ag, 5090 Leverkusen | Distyrylverbindungen |
| US4822780A (en) * | 1987-07-08 | 1989-04-18 | Otsuka Pharmaceutical Factory, Inc. | Carboxamide compounds |
| DE4003054A1 (de) * | 1990-02-02 | 1991-08-08 | Hoechst Ag | Verwendung von benzylphosphonsaeurederivaten zur behandlung von durch viren verursachte krankheiten |
| US5300687A (en) * | 1991-07-18 | 1994-04-05 | Ortho Pharmaceutical Corporation | Trifluoromethylbenzylphosphonates useful in treating osteoporosis |
-
1991
- 1991-07-18 US US07/732,267 patent/US5300687A/en not_active Expired - Lifetime
-
1992
- 1992-07-13 AU AU19656/92A patent/AU657146B2/en not_active Expired - Fee Related
- 1992-07-15 KR KR1019920012631A patent/KR930002364A/ko not_active Application Discontinuation
- 1992-07-16 CA CA002074020A patent/CA2074020A1/en not_active Abandoned
- 1992-07-17 HU HU9202353A patent/HUT62907A/hu unknown
- 1992-07-17 FI FI923289A patent/FI923289A/fi not_active Application Discontinuation
- 1992-07-17 MX MX9204229A patent/MX9204229A/es unknown
- 1992-07-17 ZA ZA925391A patent/ZA925391B/xx unknown
- 1992-07-17 IE IE234192A patent/IE922341A1/en not_active Application Discontinuation
- 1992-07-17 NO NO92922851A patent/NO922851L/no unknown
- 1992-07-17 JP JP4212292A patent/JPH05213977A/ja active Pending
- 1992-07-17 EP EP92306602A patent/EP0524023A1/en not_active Withdrawn
- 1992-07-18 CN CN92109763A patent/CN1070408A/zh not_active Withdrawn
- 1992-08-08 TW TW081106270A patent/TW216796B/zh active
-
1993
- 1993-12-09 US US08/164,602 patent/US5532226A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ZA925391B (en) | 1994-01-17 |
| NO922851D0 (no) | 1992-07-17 |
| JPH05213977A (ja) | 1993-08-24 |
| MX9204229A (es) | 1993-04-01 |
| HUT62907A (en) | 1993-06-28 |
| AU657146B2 (en) | 1995-03-02 |
| IE922341A1 (en) | 1993-01-27 |
| HU9202353D0 (en) | 1992-10-28 |
| US5300687A (en) | 1994-04-05 |
| NO922851L (no) | 1993-01-19 |
| TW216796B (ko) | 1993-12-01 |
| CN1070408A (zh) | 1993-03-31 |
| AU1965692A (en) | 1993-01-21 |
| FI923289A0 (fi) | 1992-07-17 |
| CA2074020A1 (en) | 1993-01-19 |
| US5532226A (en) | 1996-07-02 |
| EP0524023A1 (en) | 1993-01-20 |
| FI923289A (fi) | 1993-01-19 |
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