KR920000778A - 비스포스폰산 유도체, 그의 제조와 용도 - Google Patents
비스포스폰산 유도체, 그의 제조와 용도 Download PDFInfo
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- KR920000778A KR920000778A KR1019910010616A KR910010616A KR920000778A KR 920000778 A KR920000778 A KR 920000778A KR 1019910010616 A KR1019910010616 A KR 1019910010616A KR 910010616 A KR910010616 A KR 910010616A KR 920000778 A KR920000778 A KR 920000778A
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- 239000002253 acid Substances 0.000 title claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims abstract 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 8
- 150000003839 salts Chemical class 0.000 claims abstract 8
- 125000002252 acyl group Chemical group 0.000 claims abstract 6
- 229940078581 Bone resorption inhibitor Drugs 0.000 claims abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000005907 alkyl ester group Chemical group 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- UIUDOKJAPVWEPX-UHFFFAOYSA-N [phosphono-(4-pyridin-2-ylsulfanylbutylamino)methyl]phosphonic acid Chemical compound OP(O)(=O)C(P(O)(O)=O)NCCCCSC1=CC=CC=N1 UIUDOKJAPVWEPX-UHFFFAOYSA-N 0.000 claims 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000004149 thio group Chemical group *S* 0.000 claims 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 1
- -1 4-[(1-methyl-1,2,3,4-tetrazol-5-yl) thio] butylaminomethylenebisphosphonic acid Chemical compound 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 1
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims 1
- RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical class OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 claims 1
- QTYSMFSLJXMVRM-UHFFFAOYSA-N [(4-phenylsulfanylbutylamino)-phosphonomethyl]phosphonic acid Chemical compound OP(O)(=O)C(P(O)(O)=O)NCCCCSC1=CC=CC=C1 QTYSMFSLJXMVRM-UHFFFAOYSA-N 0.000 claims 1
- AEDPOTDCAAOODK-UHFFFAOYSA-N [butylamino(phosphono)methyl]phosphonic acid Chemical compound CCCCNC(P(O)(O)=O)P(O)(O)=O AEDPOTDCAAOODK-UHFFFAOYSA-N 0.000 claims 1
- QOUWXIKEWMEADL-UHFFFAOYSA-N [phosphono-[4-(1,3-thiazol-2-ylsulfanyl)butylamino]methyl]phosphonic acid Chemical compound OP(O)(=O)C(P(O)(O)=O)NCCCCSC1=NC=CS1 QOUWXIKEWMEADL-UHFFFAOYSA-N 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims 1
- 125000005750 substituted cyclic group Chemical group 0.000 abstract 1
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- 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
- C07F9/405—Esters of poly(thio)phosphonic acids containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)
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- 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
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- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
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- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- 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
- C07F9/3839—Polyphosphonic acids
- C07F9/3873—Polyphosphonic acids containing nitrogen substituent, e.g. N.....H or N-hydrocarbon group which can be substituted by halogen or nitro(so), N.....O, N.....S, N.....C(=X)- (X =O, S), N.....N, N...C(=X)...N (X =O, S)
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- 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
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- 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
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
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- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
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- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
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- 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
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Abstract
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Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (15)
- 하기 일반식(I)의 비스포스폰산 유도체 또는 그것의 염:(식중, A는 임의로 치환된 고리기이고, R1은 수소원자 또는 저급 알카노일기이며, R2, R3, R4및 R5는 같거나 다르고, 수소원자 또는 저급알킬기이며, m은 0,1 또는 2이며, n은 2-10의 정수이다.)
- 제1항에 있어서, 임의로 치환된 고리기의 고리기는 C6-14방향족 탄화수소기, 1-4개의 헤테로원자를 함유하는 5 또는 6원 방향족 헤테로고리기, C6-14방향족 탄화수소고리 또는 1-4개의 질소, 산소 및/또는 황원자를 함유하는 5 또는 6원 방향족 헤테로고리와 공역된 1-4개의 질소, 산소 및/또는 황원자를 함유하는 5 또는 6원 방향족 헤테로고리기, C3-7시클로알킬기, 또는 1-4개의 헤테로원자들을 함유하는 5 또는 6원 비-방향족 헤테로 고리기이며, 이들 고리기는 (1)할로겐원자, (2)니트로, (3)할로겐원자, 히드록시기 및 C1-6알콕시기로 구성되는 군에서 선택된 1-3개의 치환체로 치환될수 있는 C1-7알킬기, (4)할로겐 원자, 히드록시기 및 C1-6알콕시기로 구성되는 군에서 선택된 1-3개의 치환체로 치환될 수 있는 C3-7시클로알킬기, (5)히드록실, (6)할로겐, 히드록실 및 C1-6알콕시기로 구성되는 군에서 선택된 1-3개의 치환체로 치환될 수 있는 C1-6알콕시기, C4-6시클로알콕시기, C2-6알켄일옥시, C6-19아랄킬옥시, C2-7알카노일옥시 및 C6-14아릴옥시로 구성되는 군에서 선택된 보호된 히드록시기, (7)티올 및 (8)할로겐, 히드록시기 및 C1-6알콕시기로 구성되는 군에서 선택되는 1-3개의 치환체로 치환될 수 있는 C1-6알킬티오, C4-7시클로알킬티오, C7-19아랄킬티오 및 C2-7알카노일 티오기로 구성되는 군에서 선택되는 보호된 티올기의 군에서 선택되는 1-4개의 치환체로 임의로 치환된 것임을 특징으로 하는 화합물.
- 제1항에 있어서, R1으로 표시되는 저급알카노일이 C1-6알킬-카르보닐기인 화합물.
- 제1항에 있어서, R2, R3, R4및 R5로 표시되는 저급 알킬기가 C1-4알킬기인 화합물.
- 제1항에 있어서, A가 페닐기인 화합물.
- 제1항에 있어서, A는 피리딜기인 화합물.
- 제1항에 있어서, 4-(페닐티오)부틸아미노메틸렌비스포스폰산 또는 그것의 염 또는 C1-4알킬에스테르인 화합물.
- 제1항에 있어서, 4-(페닐티오)부틸아미노메틸렌비스폰스폰산인 화합물.
- 제1항에 있어서, 4-(2-피리딜티오)부틸아미노메틸렌비스포스폰산 또는 그것의 염 또는 C1-4알킬에스테르기인 화합물.
- 제1항에 있어서, 4-(2-피리딜티오)부틸아미노메틸렌비스포스폰산인 화합물.
- 제1항에 있어서, 4-[(4-메톡시페닐)티오)부틸아미노메틸렌비스포스폰산 또는 그것의 염 또는 C1-4알킬 에스테르기인 화합물.
- 제1항에 있어서, 4-[(1-메틸-1,2,3,4-테트라졸-5-일)티오]부틸아미노메틸렌비스포스폰산 또는 그것의 염 또는 C1-4알킬에스테르기인 화합물.
- 제1항에 있어서, 4-[(2-티아졸일)티오]부틸아미노메틸렌비스포스폰산 또는 그것의 염 또는 C1-4알킬에스테르기인 화합물.
- 일반식(Ⅱ)의 아민유도체를 일반식(Ⅲ)의 오르토포름산 유도체 및 일반식(Ⅳ)의 포스파이트 유도체와 반응시킨 다음, 임의로 아실화, 산화 및/또는 가수분해 시키는 것을 특징으로 하는 하기 일반식(I)의 화합물의 제조방법.(식중, A는 임의로 치환된 고리기이고, R1은 수소원자 또는 저급 알카노일기이며, R2, R3, R4및 R5는 같거나 다르고, 수소원자 또는 저급알킬기이며, m은 0,1 또는 2이며, n은 2-10의 정수이며, R6는 저급 알킬기이고, R7, R8, R9및 R10은 같거나 다르며 저급 알킬기이다.)
- 하기 일반식(I)의 화합물 또는 그것의 염, 그리고 약학적 허용가능한 담체, 희석제 또는 부형제를 함유하는 골-재흡수억제 조성물.(식중, A는 임의로 치환된 고리기이고, R1은 수소원자 또는 저급 알카노일기이며, R2, R3, R4및 R5는 같거나 다르고, 수소원자 또는 저급알킬기이며, m은 0,1 또는 2이며, n은 2-10의 정수이다.)※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP167600/1990 | 1990-06-25 | ||
| JP16760090 | 1990-06-25 | ||
| JP410501/1990 | 1990-12-12 | ||
| JP41050190 | 1990-12-12 | ||
| JP9208091 | 1991-04-23 | ||
| JP092080/1991 | 1991-04-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR920000778A true KR920000778A (ko) | 1992-01-29 |
Family
ID=27306931
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019910010616A KR920000778A (ko) | 1990-06-25 | 1991-06-25 | 비스포스폰산 유도체, 그의 제조와 용도 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US5376647A (ko) |
| EP (1) | EP0464509B1 (ko) |
| JP (1) | JP3072390B2 (ko) |
| KR (1) | KR920000778A (ko) |
| CN (1) | CN1057654A (ko) |
| AT (1) | ATE127123T1 (ko) |
| AU (1) | AU637508B2 (ko) |
| CA (1) | CA2045293A1 (ko) |
| DE (1) | DE69112511T2 (ko) |
| FI (1) | FI913067A (ko) |
| HU (1) | HUT57787A (ko) |
| IE (1) | IE912115A1 (ko) |
| NO (1) | NO912462L (ko) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0531253T3 (da) * | 1991-08-27 | 1997-01-27 | Ciba Geigy Ag | N-substituerede aminomethandiphosphonsyrer |
| EP0541037A3 (en) * | 1991-11-06 | 1997-02-26 | Takeda Chemical Industries Ltd | Squalene synthetase inhibitory composition and use thereof |
| EP0854724B1 (en) * | 1995-09-29 | 2005-03-16 | Novartis AG | Method of treating the navicular disease in horses |
| PL205637B1 (pl) * | 2004-10-22 | 2010-05-31 | Inst Farmaceutyczny | Sposób wytwarzania kwasu (R,E)-(1-{1-{3-[2-(7-chlorochinolin-2-ylo)etenylo]fenylo}-3-[2-(1-hydroksy-1-metyloetylo)fenylo] propylosulfanylometylo}cyklopropylo)octowego i/lub jego farmaceutycznie dopuszczalnych soli |
| PL205444B1 (pl) * | 2007-05-02 | 2010-04-30 | Zak & Lstrok Ady Farmaceutyczn | Sposób wytwarzania soli sodowej kwasu 1-(((1(R)-(3-(2-(7--chloro-2- chinolinylo)-etenylo)fenylo)-3-(2-(1-hydroksy-1- metyloetylo)fenylo)propylo)sulfanylo)metylo)-cyklopropanooctowego |
| US20160016982A1 (en) | 2009-07-31 | 2016-01-21 | Thar Pharmaceuticals, Inc. | Crystallization method and bioavailability |
| ES2650665T3 (es) * | 2009-07-31 | 2018-01-19 | Grünenthal GmbH | Método de cristalización y biodisponibilidad |
| US9169279B2 (en) | 2009-07-31 | 2015-10-27 | Thar Pharmaceuticals, Inc. | Crystallization method and bioavailability |
| EP2488544B1 (en) | 2009-10-15 | 2015-03-18 | Monash University | Affinity ligands and methods for protein purification |
| WO2012071517A2 (en) | 2010-11-24 | 2012-05-31 | Thar Pharmaceuticals, Inc. | Novel crystalline forms |
| WO2017208070A1 (en) | 2016-05-31 | 2017-12-07 | Grünenthal GmbH | Bisphosphonic acid and coformers with lysin, glycin, nicotinamide for treating psoriatic arthritis |
| CN110114366A (zh) * | 2016-06-03 | 2019-08-09 | 百奥维骨有限责任公司 | 双膦酸喹诺酮缀合物及其用途 |
| US10865220B2 (en) | 2016-06-03 | 2020-12-15 | Biovinc, Llc | Bisphosphonate quinolone conjugates and uses thereof |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU445675A1 (ru) * | 1972-12-28 | 1974-10-05 | Казанский государственный университет им. В.И.Ульянова-Ленина | Способ получени =фениламинотетралкилдифосфонметана |
| NL7613779A (nl) * | 1975-12-16 | 1977-06-20 | Hoechst Ag | Werkwijze voor het bereiden van fosfor bevat- tende polyadducten. |
| JPS5437829A (en) * | 1977-08-29 | 1979-03-20 | Nissan Chem Ind Ltd | Disulfonic acid type herbicidal and insecticidal agents |
| FR2531088B1 (fr) * | 1982-07-29 | 1987-08-28 | Sanofi Sa | Produits anti-inflammatoires derives de l'acide methylenediphosphonique et leur procede de preparation |
| FR2558837B1 (fr) * | 1984-01-26 | 1986-06-27 | Sanofi Sa | Derives de l'acide methylenediphosphonique, procede d'obtention et medicaments antirhumatismaux les contenant |
| DE3540150A1 (de) * | 1985-11-13 | 1987-05-14 | Boehringer Mannheim Gmbh | Neue diphosphonsaeurederivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| US4902679A (en) * | 1985-12-13 | 1990-02-20 | Norwich Eaton Pharmaceuticals, Inc. | Methods of treating diseases with certain geminal diphosphonates |
| DE3770982D1 (de) * | 1986-04-24 | 1991-08-01 | Fujisawa Pharmaceutical Co | Diphosphonsaeure-verbindungen, verfahren zu deren herstellung und sie enthaltende arzneimittel. |
| US4973576A (en) * | 1987-03-10 | 1990-11-27 | Yamanouchi Pharmaceutical Co., Ltd. | Bisphophonic acid derivatives and pharmaceutical compositions containing the same |
| KR880011136A (ko) * | 1987-03-11 | 1988-10-26 | 모리오까 시게오 | 아졸- 아미노메틸렌 비스포스폰산 유도체 |
| IL86951A (en) * | 1987-07-06 | 1996-07-23 | Procter & Gamble Pharma | Methylene phosphonoalkylphosphinates and pharmaceutical preparations containing them |
| CA1339805C (en) * | 1988-01-20 | 1998-04-07 | Yasuo Isomura | (cycloalkylamino)methylenebis(phosphonic acid) and medicines containing the same as an active |
| JPH01258695A (ja) * | 1988-04-07 | 1989-10-16 | Yamanouchi Pharmaceut Co Ltd | （ピラゾリルアミノ）メチレンビス（ホスホン酸）誘導体及びその医薬 |
| US4933472A (en) * | 1988-04-08 | 1990-06-12 | Yamanouchi Pharmaceutical Co., Ltd. | Substituted aminomethylenebis(phosphonic acid) derivatives |
| PH26923A (en) * | 1989-03-08 | 1992-12-03 | Ciba Geigy | N-substituted amino alkanediphosphonic acids |
-
1991
- 1991-06-19 IE IE211591A patent/IE912115A1/en unknown
- 1991-06-21 AT AT91110239T patent/ATE127123T1/de not_active IP Right Cessation
- 1991-06-21 DE DE69112511T patent/DE69112511T2/de not_active Expired - Fee Related
- 1991-06-21 EP EP91110239A patent/EP0464509B1/en not_active Expired - Lifetime
- 1991-06-24 NO NO91912462A patent/NO912462L/no unknown
- 1991-06-24 AU AU79287/91A patent/AU637508B2/en not_active Ceased
- 1991-06-24 CA CA002045293A patent/CA2045293A1/en not_active Abandoned
- 1991-06-24 HU HU912105A patent/HUT57787A/hu unknown
- 1991-06-24 JP JP03151484A patent/JP3072390B2/ja not_active Expired - Fee Related
- 1991-06-24 FI FI913067A patent/FI913067A/fi not_active Application Discontinuation
- 1991-06-25 KR KR1019910010616A patent/KR920000778A/ko not_active Application Discontinuation
- 1991-06-25 CN CN91104316A patent/CN1057654A/zh active Pending
-
1993
- 1993-01-19 US US08/003,955 patent/US5376647A/en not_active Expired - Fee Related
-
1994
- 1994-09-09 US US08/303,665 patent/US5512552A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ATE127123T1 (de) | 1995-09-15 |
| EP0464509A1 (en) | 1992-01-08 |
| DE69112511D1 (de) | 1995-10-05 |
| US5376647A (en) | 1994-12-27 |
| HUT57787A (en) | 1991-12-30 |
| US5512552A (en) | 1996-04-30 |
| CA2045293A1 (en) | 1991-12-26 |
| JP3072390B2 (ja) | 2000-07-31 |
| JPH05294979A (ja) | 1993-11-09 |
| NO912462L (no) | 1991-12-27 |
| EP0464509B1 (en) | 1995-08-30 |
| DE69112511T2 (de) | 1996-02-08 |
| IE912115A1 (en) | 1992-01-01 |
| FI913067A (fi) | 1991-12-26 |
| NO912462D0 (no) | 1991-06-24 |
| FI913067A0 (fi) | 1991-06-24 |
| CN1057654A (zh) | 1992-01-08 |
| AU637508B2 (en) | 1993-05-27 |
| AU7928791A (en) | 1992-01-02 |
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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 |