KR930010047A - 아미노알칸포스핀산 및 이의 염 - Google Patents
아미노알칸포스핀산 및 이의 염 Download PDFInfo
- Publication number
- KR930010047A KR930010047A KR1019920021950A KR920021950A KR930010047A KR 930010047 A KR930010047 A KR 930010047A KR 1019920021950 A KR1019920021950 A KR 1019920021950A KR 920021950 A KR920021950 A KR 920021950A KR 930010047 A KR930010047 A KR 930010047A
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- KR
- South Korea
- Prior art keywords
- ethyl
- hydroxy
- propyl
- phosphinic acid
- amino
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims abstract 23
- 239000002253 acid Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 14
- -1 1- (4-chlorophenyl) ethyl Chemical group 0.000 claims 65
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 35
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 35
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 9
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 8
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 3
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 claims 2
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 2
- 125000006185 3,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])[H])C([H])([H])[H])C([H])([H])* 0.000 claims 2
- CGXRUXCVQWFYAD-JRZJBTRGSA-N [(2s)-3-[1-(1,3-benzodioxol-5-yl)ethylamino]-2-hydroxypropyl]-benzylphosphinic acid Chemical compound C([C@@H](O)CNC(C)C=1C=C2OCOC2=CC=1)P(O)(=O)CC1=CC=CC=C1 CGXRUXCVQWFYAD-JRZJBTRGSA-N 0.000 claims 2
- AKRYTISXUYDZNA-YJBOKZPZSA-N benzyl-[(2s)-2-hydroxy-3-[[(1s)-1-(3,4,5-trimethoxyphenyl)ethyl]amino]propyl]phosphinic acid Chemical compound COC1=C(OC)C(OC)=CC([C@H](C)NC[C@H](O)CP(O)(=O)CC=2C=CC=CC=2)=C1 AKRYTISXUYDZNA-YJBOKZPZSA-N 0.000 claims 2
- HJTFXDFPIRCUFZ-PKHIMPSTSA-N benzyl-[(2s)-3-[1-(3,4-dimethoxyphenyl)ethylamino]-2-hydroxypropyl]phosphinic acid Chemical compound C1=C(OC)C(OC)=CC=C1C(C)NC[C@H](O)CP(O)(=O)CC1=CC=CC=C1 HJTFXDFPIRCUFZ-PKHIMPSTSA-N 0.000 claims 2
- LLPFZBXIVPKSPF-UHFFFAOYSA-N diethoxymethyl(propyl)phosphinic acid Chemical compound CCCP(O)(=O)C(OCC)OCC LLPFZBXIVPKSPF-UHFFFAOYSA-N 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- LEVONNIFUFSRKZ-UHFFFAOYSA-N 3-(carboxymethyl)-2,2-dimethylcyclobutane-1-carboxylic acid Chemical compound CC1(C)C(CC(O)=O)CC1C(O)=O LEVONNIFUFSRKZ-UHFFFAOYSA-N 0.000 claims 1
- YWPQYNDOJLNSOY-UHFFFAOYSA-N 3-[(3,5-dichlorophenyl)methylamino]propyl-(diethoxymethyl)phosphinic acid Chemical compound CCOC(OCC)P(O)(=O)CCCNCC1=CC(Cl)=CC(Cl)=C1 YWPQYNDOJLNSOY-UHFFFAOYSA-N 0.000 claims 1
- GWXUQLHTLLJVMG-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl-methylamino]propyl-(cyclohexylmethyl)phosphinic acid Chemical compound C=1C=C(Cl)C=CC=1CN(C)CCCP(O)(=O)CC1CCCCC1 GWXUQLHTLLJVMG-UHFFFAOYSA-N 0.000 claims 1
- JIVCLEJPGLAXJH-HNNXBMFYSA-N 3-[[(1s)-1-(3-chlorophenyl)ethyl]amino]propyl-(cyclohexylmethyl)phosphinic acid Chemical compound N([C@@H](C)C=1C=C(Cl)C=CC=1)CCCP(O)(=O)CC1CCCCC1 JIVCLEJPGLAXJH-HNNXBMFYSA-N 0.000 claims 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 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
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 1
- RRXSYZFVDIRTFB-UHFFFAOYSA-N C[CH]C1=CC=C(OC)C=C1 Chemical group C[CH]C1=CC=C(OC)C=C1 RRXSYZFVDIRTFB-UHFFFAOYSA-N 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- IBVCNRUWDCKLKX-LBPRGKRZSA-N [(2s)-3-[(3,4-dichlorophenyl)methylamino]-2-hydroxypropyl]-(diethoxymethyl)phosphinic acid Chemical compound CCOC(OCC)P(O)(=O)C[C@@H](O)CNCC1=CC=C(Cl)C(Cl)=C1 IBVCNRUWDCKLKX-LBPRGKRZSA-N 0.000 claims 1
- NGDHZDNEPMXLEA-JRZJBTRGSA-N [(2s)-3-[1-(1,3-benzodioxol-5-yl)ethylamino]-2-hydroxypropyl]-(cyclohexylmethyl)phosphinic acid Chemical compound C([C@@H](O)CNC(C)C=1C=C2OCOC2=CC=1)P(O)(=O)CC1CCCCC1 NGDHZDNEPMXLEA-JRZJBTRGSA-N 0.000 claims 1
- IDZYEGQLSLKQRY-KSSFIOAISA-N [(2s)-3-[[(1s)-1-(3-chlorophenyl)ethyl]amino]-2-hydroxypropyl]-(cyclohexylmethyl)phosphinic acid Chemical compound C([C@@H](O)CN[C@@H](C)C=1C=C(Cl)C=CC=1)P(O)(=O)CC1CCCCC1 IDZYEGQLSLKQRY-KSSFIOAISA-N 0.000 claims 1
- IWDWFFFTGZJMIW-JTQLQIEISA-N [(2s)-3-amino-2-hydroxypropyl]-[(4-methoxyphenyl)methyl]phosphinic acid Chemical compound COC1=CC=C(CP(O)(=O)C[C@@H](O)CN)C=C1 IWDWFFFTGZJMIW-JTQLQIEISA-N 0.000 claims 1
- WUUBZZOIRNAYJU-MNEFBYGVSA-N benzyl-[(2s)-2-hydroxy-3-[[(1r,2r)-1-hydroxy-1-phenylpropan-2-yl]amino]propyl]phosphinic acid Chemical compound C([C@@H](O)CN[C@H](C)[C@H](O)C=1C=CC=CC=1)P(O)(=O)CC1=CC=CC=C1 WUUBZZOIRNAYJU-MNEFBYGVSA-N 0.000 claims 1
- NAOLGPMUMLJCMF-LWKPJOBUSA-N benzyl-[(2s)-3-[1-(2,5-dimethoxyphenyl)ethylamino]-2-hydroxypropyl]phosphinic acid Chemical compound COC1=CC=C(OC)C(C(C)NC[C@H](O)CP(O)(=O)CC=2C=CC=CC=2)=C1 NAOLGPMUMLJCMF-LWKPJOBUSA-N 0.000 claims 1
- RTLKLHOQOCIOPJ-LWGFOQHQSA-N benzyl-[(2s)-3-[[1-(3,4-dichlorophenyl)-1-hydroxypropan-2-yl]amino]-2-hydroxypropyl]phosphinic acid Chemical compound C([C@@H](O)CNC(C)C(O)C=1C=C(Cl)C(Cl)=CC=1)P(O)(=O)CC1=CC=CC=C1 RTLKLHOQOCIOPJ-LWGFOQHQSA-N 0.000 claims 1
- VJTCABFDIJLBHR-BUSXIPJBSA-N benzyl-[(2s)-3-[[1-(3,4-dichlorophenyl)-2-hydroxyethyl]amino]-2-hydroxypropyl]phosphinic acid Chemical compound C([C@@H](O)CNC(CO)C=1C=C(Cl)C(Cl)=CC=1)P(O)(=O)CC1=CC=CC=C1 VJTCABFDIJLBHR-BUSXIPJBSA-N 0.000 claims 1
- CYNRMRPCCGSPBK-BUSXIPJBSA-N benzyl-[(2s)-3-[[2-(3,4-dichlorophenyl)-2-hydroxyethyl]amino]-2-hydroxypropyl]phosphinic acid Chemical compound C([C@H](O)CP(O)(=O)CC=1C=CC=CC=1)NCC(O)C1=CC=C(Cl)C(Cl)=C1 CYNRMRPCCGSPBK-BUSXIPJBSA-N 0.000 claims 1
- NNQRKHDOOIFRTJ-DIMJTDRSSA-N benzyl-[(2s)-3-[[cyclopropyl-(3,4-dichlorophenyl)methyl]amino]-2-hydroxypropyl]phosphinic acid Chemical compound C([C@H](O)CP(O)(=O)CC=1C=CC=CC=1)NC(C=1C=C(Cl)C(Cl)=CC=1)C1CC1 NNQRKHDOOIFRTJ-DIMJTDRSSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- DGJHLAULRJZSHW-XUJLQICISA-N cyclohex-3-en-1-ylmethyl-[(2s)-3-[1-(3,4-dichlorophenyl)ethylamino]-2-hydroxypropyl]phosphinic acid Chemical compound C([C@@H](O)CNC(C)C=1C=C(Cl)C(Cl)=CC=1)P(O)(=O)CC1CCC=CC1 DGJHLAULRJZSHW-XUJLQICISA-N 0.000 claims 1
- WLHBFPVBRQTWHR-PKHIMPSTSA-N cyclohexylmethyl-[(2s)-2-hydroxy-3-[1-(3,4,5-trimethoxyphenyl)ethylamino]propyl]phosphinic acid Chemical compound COC1=C(OC)C(OC)=CC(C(C)NC[C@H](O)CP(O)(=O)CC2CCCCC2)=C1 WLHBFPVBRQTWHR-PKHIMPSTSA-N 0.000 claims 1
- TYIUCIAIYKYLMH-MNEFBYGVSA-N cyclohexylmethyl-[(2s)-2-hydroxy-3-[[(1r,2r)-1-hydroxy-1-phenylpropan-2-yl]amino]propyl]phosphinic acid Chemical compound C([C@@H](O)CN[C@H](C)[C@H](O)C=1C=CC=CC=1)P(O)(=O)CC1CCCCC1 TYIUCIAIYKYLMH-MNEFBYGVSA-N 0.000 claims 1
- WLHBFPVBRQTWHR-YJBOKZPZSA-N cyclohexylmethyl-[(2s)-2-hydroxy-3-[[(1s)-1-(3,4,5-trimethoxyphenyl)ethyl]amino]propyl]phosphinic acid Chemical compound COC1=C(OC)C(OC)=CC([C@H](C)NC[C@H](O)CP(O)(=O)CC2CCCCC2)=C1 WLHBFPVBRQTWHR-YJBOKZPZSA-N 0.000 claims 1
- JGGVBBYJRQOPPA-VYIIXAMBSA-N cyclohexylmethyl-[(2s)-3-[1-(3,4-dichlorophenyl)ethylamino]-2-hydroxypropyl]phosphinic acid Chemical compound C([C@@H](O)CNC(C)C=1C=C(Cl)C(Cl)=CC=1)P(O)(=O)CC1CCCCC1 JGGVBBYJRQOPPA-VYIIXAMBSA-N 0.000 claims 1
- CFHOKTMPHWZCRU-PKHIMPSTSA-N cyclohexylmethyl-[(2s)-3-[1-(3,4-dimethoxyphenyl)ethylamino]-2-hydroxypropyl]phosphinic acid Chemical compound C1=C(OC)C(OC)=CC=C1C(C)NC[C@H](O)CP(O)(=O)CC1CCCCC1 CFHOKTMPHWZCRU-PKHIMPSTSA-N 0.000 claims 1
- JGGVBBYJRQOPPA-BBRMVZONSA-N cyclohexylmethyl-[(2s)-3-[[(1s)-1-(3,4-dichlorophenyl)ethyl]amino]-2-hydroxypropyl]phosphinic acid Chemical compound C([C@@H](O)CN[C@@H](C)C=1C=C(Cl)C(Cl)=CC=1)P(O)(=O)CC1CCCCC1 JGGVBBYJRQOPPA-BBRMVZONSA-N 0.000 claims 1
- BEAYZSRPPYXMIL-UHFFFAOYSA-N cyclohexylmethyl-[3-[(3,5-dichlorophenyl)methylamino]propyl]phosphinic acid Chemical compound C1CCCCC1CP(=O)(O)CCCNCC1=CC(Cl)=CC(Cl)=C1 BEAYZSRPPYXMIL-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims 1
- 239000005557 antagonist Substances 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
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- 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
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
- C07F9/65517—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
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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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
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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
- C07F9/547—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
- C07F9/553—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
- C07F9/60—Quinoline or hydrogenated quinoline ring systems
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
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- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
하기 일반식(I)의 화합물 및 이의 염은 GABAB-길항 특성을 지니며 GABAB-길항제에 응하는 질병의 치료에 사용할 수 있다.
상기식에서 R, R1, 내지 R3는 본 명세서에서 정의한 바와 동일하다.
Description
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Claims (16)
- 일반식(I)의 화합물 또는 이의 염.상기식에서, a)R은 부틸이고, R1은 수소이고, R2는 3,4-디클로로벤질, 1-(4-클로로페닐)에틸 또는 1-(3,4-디클로로페닐)에틸이고, R3은 수소이거나, b)R은 디에톡시메틸이고, R1은 수소이고, R2는 2,6-또는 3,5-디클로로벤질, 피리드-3-일메틸, 1-(4-메톡시페닐)에틸, 1-(4-클로로-3-요오드-페닐)에틸 또는 1-(3-클로로-4-요오드-페닐)에틸이고, R3은 수소이거나, 또는 R은 디에톡시메틸이고, R1은 하이드록시이고, R2는 3,4-디클로로벤질, 1-(3-클로로-4-요오드-페닐)에틸, 1-(4-클로로-3-요오드-페닐)에틸 또는 1-(3,4-디클로로벤질)에틸이고, R3은 수소이거나, c)R은 사이클로헥실메틸이고, R1은 수소이고, R2는 3,5-디클로로벤질, 퀴놀린-4-일-메틸, 1-(3-클로로페닐)에틸 또는 1-(3,4,5-트리메톡시페닐)에틸이고, R3은 수소이거나, R은 사이클로헥실메틸이고, R1은 하이드록시이고, R2는 3,4-디메틸벤질, 3,4-메틸렌디옥시벤질, 1-(3-클로로페닐)에틸, 1-(3,4-디클로로페닐)에틸, 1-(3-클로로-4-요오드-페닐)에틸, 1-(4-클로로-3-요오드-페닐)에틸, 1-(2,4-디메톡시페닐)에틸, 1-(2,5-디메톡시페닐)에틸, 1-(2,6-디메톡시페닐)에틸, 1-(3,4-디메톡시페닐)에틸, 1-(3,4-메틸렌디옥시페닐)에틸, 1-(3,5-디메톡시-페닐)에틸, 1-(3,4,5-트리메톡시페닐)에틸, 3-페닐프로프-2-일, 2-(3,4-디클로로페닐)프로필, 2-(3,4-디클로로페닐)프로필, 3-(,4-디클로로페닐)프로프-2-일 또는 3-페닐-3-하이드록시-프로프-2-일이고, R3는 수소이거나, 또는 R은 사이클로헥실메틸이고, R1은 수소이고, R2는 4-클로로벤질이고, R3은 메틸이거나, d)R은 사이클로헥스-3-에닐메틸이고, R1은 (S)-하이드록시이고, R2는 1(S)-(3,4-디클로로페닐)에틸이고, R3는 수소이거나, e)R은 벤질이고, R1은 하이드록시이고, R2는 α-사이클로프로필-3,4-디클로로-벤질, 3,4,5-트리메톡시벤질, 1-(3,5-디메톡시페닐)에틸, 1-(3,4-디클로로페닐)에틸, 2-(3,4-디클로로페닐)에틸, 1-(3-클로로-4-요오드-페닐)에틸, 1-(3,4-디클로로페닐)-2-하이드록시-에틸, 2-(,3,4-디클로로페닐)-2-하이드록시-에틸, 1-(2,4-디메톡시페닐)에틸, 1-(2,5-디메톡시페닐)에틸, 1-(2,6-디메톡시페닐)에틸, 1-(3,4-디메톡시페닐)에틸, 1-(3,4-메틸렌디옥시페닐)에틸, 1-(3,4,5-트리메톡시페닐)에틸, 3-페닐프로프-2-일, 3-페닐-3-하이드록시-프로프-2-일, 1-,2-, 또는 3-(3,4-디클로로페닐)프로필, 3-(3,4-디클로로페닐)프로프-2-일, 3-(3,4-디클로로페닐)-3-하이드록시-프로프-2-일 또는 4-(3,4-디클로로페닐)부틸이고, R3는 수소이거나, 또는 f)R은 4-클로로벤질, 4-메틸벤질, 4-메톡시벤질 또는 사이클로헥스-3-에틸메틸이고, R1, R2, 및 R3은 수소이다.
- 제1항에 있어서, R이 사이클로헥실메틸 또는 벤질이고, R1이 하이드록시이고, R2가 1-(2,4-메톡시페닐)에틸, 1-(2,5-디메톡시페닐)에틸, 1-(2,6-디메톡시페닐)에틸, 1-(3,4-디메톡시페닐)에틸, 1-(3,4-메틸렌디옥시페닐)에틸, 1-(3,5-디메톡시페닐)에틸 또는 1-(3,4,5-트리메톡시)펜에틸이고, R3이 수소인 일반식(I)의 화합물 또는 이의 염.
- 제1항에 있어서, R이 사이클로헥실메틸 또는 벤질이고, R1이 하이드록시이고, R2가 1-(3,4,5-트리메톡시페닐)에틸이고, R3이 수소인 일반식(I)의 화합물 또는 이의 염.
- 제1항 내지 제3항 중의 어느 한 항에 있어서, R1이 하이드록시이고, 1-(3,4-디클로로-, 3-클로로-4-요오드-, 4-클로로-3-요오드-, 2,4-디메톡시-, 2,5-디메톡시-, 2,4-디메톡시-, 3,4-디메톡시-, 3,5-디메톡시, 3,4,5-트리메톡시- 및 3,4-메틸렌디옥시페닐)에틸, α-사이클로프로필-4,4-디클로로-벤질 및 1-(3,4-디클로로페닐)프로필의 하이드록시 그룹 함유 탄소원자 및, 존재하는 경우, α-탄소원자가 (S)-배위를 갖고, R, R2및 R3은 각각의 경우에 위에서 정의한 바와 동일한 일반식(I)의 화합물 또는 이의 염.
- 3-{N-[1-(3,4,5-트리메톡시페닐)에틸]아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산 또는 이의 염.
- 3-{N-[1(S)-(3,4,5-트리메톡시페닐)에틸]아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산 또는 이의 염.
- 3-{N-[1-(3,4-메틸렌디옥시페닐)에틸]아미노}-2(S)-하이드록시-프로필-(벤질)-포스핀산 또는 이의 염.
- 3-{N-[1-(3,4-디메톡시페닐)에틸]아미노}-2(S)-하이드록시-프로필-(벤질)-포스핀산 또는 이의 염.
- 3-{N-[1-(3,4-디메톡시페닐)에틸]아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산 또는 이의 염.
- 3-{N-[1-(3,4-메틸렌디옥시페닐)에틸]아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산 또는 이의 염.
- 3-{N-[1-(3,4-메틸렌디옥시페닐)아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산 또는 이의 염.
- 3-{N-[1(S)-(3,4,5-트리메톡시페닐)에틸]아미노}-2(S)-하이드록시-프로필-(벤질)-포스핀산 또는 이의 염.
- 3-(3,5-디클로로벤질아미노)프로필(디에톡시메틸)포스핀산, 3-{N-1-(3,4-디클로로페닐)에틸]아미노}-2(S)-하이드록시-프로필(사이클로헥실메틸)포스핀산, 3-{N-(2,6-디클로로벤질)아미노]프로필-(디에톡시메틸)-포스핀산 또는 이의 염, 3-[N-(피리드-3-일메틸)아미노]프로필-(디에톡시메틸)-포스핀산, 3-{N-[1-(4-메톡시페닐)에틸]아미노)프로필-(디에톡시메틸)-포스핀산, 3-[N-(3,4,5-트리메톡시벤질)아미노]-2(S)-하이드록시-프로필-(벤질)-포스핀산, 3-{N-[-1-(3,4-디클로로페닐)에틸]아미노}-2(S)-하이드록시-프로필(벤질)-포스핀산, 3-{N-[-1-(3,4-디클로로페닐)에틸]아미노}-2(S)-하이드록시-프로필-(사이클로헥스-3-에닐메틸)-포스핀산, 3-[(3,5-디클로로벤질)아미노]-프로필-(사이클로헥실메틸)-포스핀산, 3-[N-퀴놀린-4-일)메틸아미노]-프로필-(사이클로헥실메틸)-포스핀산, 3-[N-(4-클로로벤질)-N-메틸-아미노]-프로필-(사이클로헥실메틸)-포스핀산, 3-[N-(3,4-클로로벤질)아미노]-프로필-(부틸)-포스핀산, 3-{N-[1-(4-클로로페닐)에틸아미노}-프로필-(부틸)-포스핀산 또는 이의 염, 3-{N-[1-(3,4-디클로로페닐)에틸아미노}-프로필-(부틸)-포스핀산 또는 이의 염, 3-{N-[1-(3-클로로-4-요오드-페닐)에틸]아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산, 3-{N-[1-4-클로로-3-요오드-페닐)에틸]아미노)-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산, 3-{N-[1-(4-클로로-3-요오드-페닐)에틸]아미노)프로필-(디에톡시메틸)-포스핀산, 3-{N-[1(S)-(3,4-디클로로페닐)에틸]아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산, 3-{N-[1(S)-(3,4-디클로로페닐)에틸]아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산, 3-[N-[1(S)-(3,4-디클로로페닐)에틸]아미노}-2(R)-하이드록시-프로필(사이콜로헥실메틸)-포스핀산, 3-[N-(3,4-디메틸벤질)아미노]-2(S)-하이드록시-프로판-(사이클로헥실메틸)-포스핀산, 3-{N-[1(R)-(3,4-디클로로페닐)에틸]아미노}-2(R)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산, 3-{N-[1(R)-(3,4-디클로로페닐)에틸]아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산, 3-{N-[1-(3-클로로-4-요오드-페닐)에틸]아미노}-2(S)-하이드록시-프로필-(벤질)-포스핀산, 3-{N-[1-(3-클로로-4-요오드-페닐)에틸]아미노}프로필-(디에톡시메틸)-포스핀산, 3-{N-[1-(3,4,5-트리메톡시페닐)에틸]아미노}프로필-(사이클로헥실메틸)-포스핀산, 3-{N-[1-(3,4-디클로로페닐)에틸]아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산,3-{N-[1(3,4-디클로로페닐)에틸]아미노}-2(S)-하이드록시-프로필-(벤질)-포스핀산,3-[N-[1(S)-(3,4,5-트리메톡시페닐)에틸]아미노}프로필-(사이콜로헥실메틸)-포스핀산,3-[N-(3,4-디클로로-α-사이클로프로필-벤질)아미노]-2(S)-하이드록시-프로필-(벤질)-포스핀산) 3-{N-[1-(2,5-디메톡시페닐)에틸]아미노}-2(S)-하이드록시-프로필-(벤질)-포스핀산, 3-{N-[1(3,4-메틸렌디옥시페닐)에틸]아미노}-2(S)-하이드록시-프로필-(벤질)-포스핀산, 3-{N-[1-(3,4-디메톡시페닐)에틸]아미노}-2(S)-하이드록시-프로필-(벤질)-포스핀산, 3-{N-[1-(2,5-디메톡시페닐)에틸아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산, 3-{N-[1-(2,6-디메톡시페닐)에틸아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산, 3-{N-[1-(3,4-디메톡시페닐)에틸아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산, 3-{N-[1-(2,4-디메톡시페닐)에틸아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산,3-{N-[1-(3,4-디메톡시페닐)에틸아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산,3-{N-[1-(3,4-디메톡시페닐)에틸아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산, 3-{N-[1(S)-(3,4,5-트리메톡시페닐)에틸]아미노}-2(S)-하이드록시-프로필-(벤질)-포스핀산,3-[N-(3,4-디클로로벤질)아미노}-2(S)-하이드록시-프로필-(디에톡시메틸)-포스핀산, 3-아미노-2(S)-하이드록시-프로필-(4-메톡시벤질)-포스핀산 또는 이들의 염.
- 3-{N-[1-(3,5-디메톡시페닐)에틸])아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산, 3-{N-[1(R)-(3,4-디클로로로페닐)에틸])아미노}-2(S)-하이드록시-프로필-(사이클로헥스-3-에닐메틸)-포스핀산, 3-{N-[1(S)-(3,4-디클로로페닐)에틸])아미노}-2(R)-하이드록시-프로필-(사이클로헥스-3-에닐메틸)-포스핀산3-{N-[1(R)-(3,4-디클로로페닐)에틸])아미노}-2(S)-하이드록시-프로필-(사이클로헥스-3-에닐메틸)-포스핀산, 3-{N-[1(R)-(3,4-클로로페닐)에틸])아미노}-2(S)-하이드록시-프로필-(벤질)-포스핀산, 3-{N-[1(S)-(3,4-디클로로페닐)에틸])아미노}-2(R)-하이드록시-프로필-(벤질)-포스핀산, 3-{N-[1(R)-(3,4-디클로로페닐)에틸])아미노}-2(S)-하이드록시-프로필-(디에톡시메닐)-포스핀산, 3-{N-[1(S)-(3,4-디클로로페닐)에틸])아미노}-2(S)-하이드록시-프로필-(디에톡시메닐)-포스핀산, 3-{N-[1(R)-(3,4-디클로로페닐)에틸])아미노}-2(S)-하이드록시-프로필-(디에톡시메닐)-포스핀산, 3-{N-[3-(3,4-디클로로페닐)에틸])아미노}-2(S)-하이드록시-프로필-(벤질)-포스핀산, 3-{N-[3(R)-(페닐)프로프-2(R)-일]아미노}-2(S)-하이드록시-프로필-(벤질)-포스핀산, 3-{N-[3(R)-(페닐)프고로프-2(R)-일]아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산, 3-{N-[3(R)-(페닐)-3-하이드록시-프로프-2(R)-일]아미노}-2(S)-하이드록시-프로필-(벤질)-포스핀산, 3-{N-[3(R)-(페닐)-3-하이드록시-프로프-2(R)-일]아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산, 3-{N-[3-(3,4-디클로로페닐)-3-하이드록시-프로프-2-일]아미노}-2(S)-하이드록시-프로필-(벤질)-포스핀산, 3-{N-[2-3,4-디클로로페닐)프로필)아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산, 3-{N-[2-3,4-디클로로페닐)프로필)아미노}-2(S)-하이드록시-프로필-(벤질)-포스핀산, 3-{N-[3-(3,4-디클로로페닐)프로프)-2-일]아미노}-2(S)-하이드록시-프로필-(벤질)-포스핀산, 3-{N-[4-(3,4-디클로로페닐)부트)-3-일]아미노}-2(S)-하이드록시-프로필-(벤질)-포스핀산, 3-{N-[1-(3,4-디클로로페닐)-2-하이드록시-에틸]아미노}-2(S)-하이드록시-프로필-(벤질)-포스핀산, 3-{N-[2-(3,4-디클로로페닐)-2-하이드록시-에틸]아미노}-2(S)-하이드록시-프로필-(벤질)-포스핀산, 3-{N-[1(S)-(3-클로로페닐)에틸]아미노}프로필-(사이클로헥실메틸)포스핀산 또는 3-{N-[1(S)-(3-클로로페닐)에틸]아미노}-2(S)-하이드록시-프로필-(사이클로헥실메틸)-포스핀산, 또는 이들의 염.
- 제1항 내지 14항 중의 어느 한 항에 따른 화합물을 통상적인 약제학적 부형제 및 담체와 함께 포함하는 약제학적 조성물.
- 일반식(Ⅱ)의 화합물 또는 이의 염에서, 하이드록시-보호 그룹 R6을 수소로 치환시켜 하이드록시 그룹을 유리시키고, 경우에 따라서 이모노-보호 그룹 R8로부터 하이드록시 그룹 R1을 유리시키고, 경우에 따라서 생성된 화합물을 일반식 (I)의 상이한 화합물로 전환시키고, 본 방법에 따라서 수득 가능한 이서아체 혼합물을 단일 성분으로 분리하고, 바람직한 이성체를 분리하고/분리하거나, 본 방법에 따라 수득 가능한 유리 화합물을 염으로 전환시키거나, 또는 본 방법에 따라 수득 가능한 염을 상응하는 유리 화합물로 전환시킴을 특징으로 하여 일반식(I)의 화합물 또는 이의 염을 제조하는 방법.상기식에서, R 및 R1내지 R3은 제1항에서 정의한 바와 동일하고, R5는 수소 또는 보호된 하이드록시이고, R6은 하이드록시 -보호 그룹이고, R8는 그룹 R3또는 아미노-보호 그룹니다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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| IL114631A (en) * | 1990-06-22 | 1998-12-06 | Novartis Ag | Anti-epileptic preparations containing antagonists of BABAG |
| EP0767174A1 (de) * | 1991-11-21 | 1997-04-09 | Ciba-Geigy Ag | Neue Aminoalkanphosphinsäuren und ihre Salze |
| AU662404B2 (en) * | 1992-05-08 | 1995-08-31 | Novartis Ag | Novel N-aralkyl- and N-heteroaralkyl-aminoalkanephosphinic acids |
| WO1997011953A1 (en) * | 1995-09-28 | 1997-04-03 | Novartis Ag | Novel hydroxylated and alkoxylated n- and/or p-aralkylphosphinic acid derivatives |
| AU744189B2 (en) * | 1997-06-23 | 2002-02-14 | Neuro Therapeutics Limited | Neurologically-active compounds |
| DE10014127A1 (de) * | 2000-03-22 | 2001-10-18 | Hassan Jomaa | Verwendung von phosphororganischen Verbindungen zur Behandlung von Infektionen |
| US6462084B1 (en) | 2001-05-14 | 2002-10-08 | Brookhaven Science Associates, Llc | Treatment for obsessive-compulsive disorder (OCD) and OCD-related disorders using GVG |
| AR045794A1 (es) * | 2003-09-23 | 2005-11-16 | Aventis Pharma Inc | Procedimiento para preparar derivados de acido 3- amino-2- hidroxipropilfosfinico |
| GB0327186D0 (en) * | 2003-11-21 | 2003-12-24 | Novartis Ag | Organic compounds |
| US7494985B2 (en) * | 2004-11-03 | 2009-02-24 | Xenoport, Inc. | Acyloxyalkyl carbamate prodrugs, methods of synthesis, and use |
| US7566738B2 (en) * | 2004-11-03 | 2009-07-28 | Xenoport, Inc. | Acyloxyalkyl carbamate prodrugs of sulfinic acids, methods of synthesis, and use |
| CA2597408A1 (en) * | 2005-02-11 | 2006-08-17 | Aventis Pharmaceuticals Inc. | Substituted propane phosphinic acid esters |
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| DE2440239A1 (de) * | 1974-08-22 | 1976-03-04 | Hoechst Ag | Innere ammoniumsalze von phosphinsaeuren |
| EP0093081B1 (de) * | 1982-04-23 | 1986-03-19 | Ciba-Geigy Ag | Herbizide und pflanzenwuchsregulierende Mittel |
| US4536355A (en) * | 1982-10-08 | 1985-08-20 | Zoecon Corporation | Phenoxyphenylaminoalkylphosphinates useful in weed control |
| US5243062A (en) * | 1984-10-12 | 1993-09-07 | Ciba-Geigy Corporation | Substituted propane-phosphonous acid compounds |
| GB8425872D0 (en) * | 1984-10-12 | 1984-11-21 | Ciba Geigy Ag | Chemical compounds |
| DK704488D0 (da) * | 1988-12-19 | 1988-12-19 | Novo Industri As | Nye n-substituerede azaheterocykliske carboxylsyrer |
| GB8728483D0 (en) * | 1987-12-04 | 1988-01-13 | Ciba Geigy Ag | Chemical compounds |
| US5300679A (en) * | 1987-12-04 | 1994-04-05 | Ciba-Geigy Corporation | Substituted propane-phosphinic acid compounds |
| US5190933A (en) * | 1987-12-04 | 1993-03-02 | Ciba-Geigy Corporation | Substituted propane-phosphinic acid compounds |
| DK270488D0 (da) * | 1988-05-18 | 1988-05-18 | Novo Industri As | Hidtil ukendte o-substituerede ketoximer |
| GB8820266D0 (en) * | 1988-08-26 | 1988-09-28 | Smith Kline French Lab | Compounds |
| GB8911017D0 (en) * | 1989-05-13 | 1989-06-28 | Ciba Geigy Ag | Substituted aminoalkylphosphinic acids |
| US5281747A (en) * | 1989-05-13 | 1994-01-25 | Ciba-Geigy Corporation | Substituted aminoalkylphosphinic acids |
| US5190934A (en) * | 1989-06-03 | 1993-03-02 | Ciba-Geigy Corporation | P-subsituted propane-phosphinic acid compounds |
| GB8912814D0 (en) * | 1989-06-03 | 1989-07-19 | Ciba Geigy Ag | P-substituted propane-phospinic acid compounds |
| IL114631A (en) * | 1990-06-22 | 1998-12-06 | Novartis Ag | Anti-epileptic preparations containing antagonists of BABAG |
| EP0767174A1 (de) * | 1991-11-21 | 1997-04-09 | Ciba-Geigy Ag | Neue Aminoalkanphosphinsäuren und ihre Salze |
| AU662404B2 (en) * | 1992-05-08 | 1995-08-31 | Novartis Ag | Novel N-aralkyl- and N-heteroaralkyl-aminoalkanephosphinic acids |
-
1992
- 1992-11-12 EP EP96118735A patent/EP0767174A1/de not_active Withdrawn
- 1992-11-12 EP EP19920810879 patent/EP0543780A3/de not_active Ceased
- 1992-11-18 FI FI925243A patent/FI925243A/fi not_active Application Discontinuation
- 1992-11-19 AU AU28504/92A patent/AU662938B2/en not_active Ceased
- 1992-11-19 US US07/979,513 patent/US5376684A/en not_active Expired - Fee Related
- 1992-11-19 CA CA002083307A patent/CA2083307A1/en not_active Abandoned
- 1992-11-19 MX MX9206702A patent/MX9206702A/es not_active Application Discontinuation
- 1992-11-19 JP JP4310082A patent/JPH05247069A/ja active Pending
- 1992-11-19 IL IL103808A patent/IL103808A0/xx unknown
- 1992-11-19 TW TW081109255A patent/TW213466B/zh active
- 1992-11-19 NZ NZ245185A patent/NZ245185A/en unknown
- 1992-11-20 PH PH45301A patent/PH30097A/en unknown
- 1992-11-20 ZA ZA928979A patent/ZA928979B/xx unknown
- 1992-11-20 NO NO92924479A patent/NO924479L/no unknown
- 1992-11-21 KR KR1019920021950A patent/KR930010047A/ko not_active Application Discontinuation
-
1994
- 1994-09-16 US US08/308,040 patent/US5500418A/en not_active Expired - Fee Related
-
1995
- 1995-12-14 AU AU40456/95A patent/AU4045695A/en not_active Abandoned
-
1997
- 1997-09-08 NO NO974117A patent/NO974117D0/no unknown
- 1997-09-08 NO NO974115A patent/NO974115D0/no unknown
- 1997-09-08 NO NO974116A patent/NO974116D0/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU4045695A (en) | 1996-04-26 |
| JPH05247069A (ja) | 1993-09-24 |
| NO974117L (no) | 1993-05-24 |
| US5500418A (en) | 1996-03-19 |
| EP0543780A2 (de) | 1993-05-26 |
| FI925243A (fi) | 1993-05-22 |
| AU2850492A (en) | 1993-05-27 |
| NO974116L (no) | 1993-05-24 |
| EP0767174A1 (de) | 1997-04-09 |
| NZ245185A (en) | 1995-04-27 |
| US5376684A (en) | 1994-12-27 |
| NO974115D0 (no) | 1997-09-08 |
| CA2083307A1 (en) | 1993-05-22 |
| ZA928979B (en) | 1994-04-15 |
| AU662938B2 (en) | 1995-09-21 |
| NO924479D0 (no) | 1992-11-20 |
| NO974115L (no) | 1993-05-24 |
| FI925243A0 (fi) | 1992-11-18 |
| NO974117D0 (no) | 1997-09-08 |
| TW213466B (ko) | 1993-09-21 |
| EP0543780A3 (en) | 1993-09-01 |
| PH30097A (en) | 1996-12-27 |
| MX9206702A (es) | 1994-06-30 |
| NO974116D0 (no) | 1997-09-08 |
| NO924479L (no) | 1993-05-24 |
| IL103808A0 (en) | 1993-04-04 |
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