NZ252587A - Phosphonate compounds; quaternary nitrogen containing compounds and pharmaceutical compositions containing them - Google Patents
Phosphonate compounds; quaternary nitrogen containing compounds and pharmaceutical compositions containing themInfo
- Publication number
- NZ252587A NZ252587A NZ252587A NZ25258793A NZ252587A NZ 252587 A NZ252587 A NZ 252587A NZ 252587 A NZ252587 A NZ 252587A NZ 25258793 A NZ25258793 A NZ 25258793A NZ 252587 A NZ252587 A NZ 252587A
- Authority
- NZ
- New Zealand
- Prior art keywords
- substituted
- alkyl
- unsubstituted
- quaternary nitrogen
- unsubstltuted
- Prior art date
Links
- 239000008194 pharmaceutical composition Chemical group 0.000 title claims description 30
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title description 28
- 150000001875 compounds Chemical class 0.000 claims description 66
- -1 nitrogen-containing phosphonate compound Chemical class 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 208000001132 Osteoporosis Diseases 0.000 claims description 30
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 29
- 239000011575 calcium Substances 0.000 claims description 29
- 229910052791 calcium Inorganic materials 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 27
- 229910019142 PO4 Inorganic materials 0.000 claims description 25
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 25
- 239000010452 phosphate Substances 0.000 claims description 25
- 125000002950 monocyclic group Chemical group 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 230000002159 abnormal effect Effects 0.000 claims description 14
- 239000002775 capsule Substances 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 230000004060 metabolic process Effects 0.000 claims description 14
- 238000002560 therapeutic procedure Methods 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000003367 polycyclic group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
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- 238000005303 weighing Methods 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 6
- 230000002829 reductive effect Effects 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 230000007423 decrease Effects 0.000 claims description 4
- 238000012423 maintenance Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
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- 208000025962 Crush injury Diseases 0.000 claims description 2
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- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 29
- 210000000988 bone and bone Anatomy 0.000 description 26
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
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- 125000003118 aryl group Chemical group 0.000 description 9
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- 229940116254 phosphonic acid Drugs 0.000 description 8
- 208000024891 symptom Diseases 0.000 description 8
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 7
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- 208000004434 Calcinosis Diseases 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 4
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 4
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- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
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- 229910052753 mercury Inorganic materials 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 230000004089 microcirculation Effects 0.000 description 1
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- 125000002757 morpholinyl group Chemical group 0.000 description 1
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- UEHLXXJAWYWUGI-UHFFFAOYSA-M nitromersol Chemical compound CC1=CC=C([N+]([O-])=O)C2=C1O[Hg]2 UEHLXXJAWYWUGI-UHFFFAOYSA-M 0.000 description 1
- 229940118238 nitromersol Drugs 0.000 description 1
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- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
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- 230000036961 partial effect Effects 0.000 description 1
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- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000008782 phagocytosis Effects 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical group [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical group O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003007 phosphonic acid derivatives Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000000554 physical therapy Methods 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
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- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- NYHLAZJBJZRGPV-UHFFFAOYSA-N s-(2-bromoethyl) ethanethioate Chemical compound CC(=O)SCCBr NYHLAZJBJZRGPV-UHFFFAOYSA-N 0.000 description 1
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- 231100000241 scar Toxicity 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
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- 239000008109 sodium starch glycolate Substances 0.000 description 1
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- 210000004872 soft tissue Anatomy 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
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- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
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- 238000002636 symptomatic treatment Methods 0.000 description 1
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- 238000012385 systemic delivery Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229910052713 technetium Inorganic materials 0.000 description 1
- 229960004989 tetracycline hydrochloride Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
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- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000012384 transportation and delivery Methods 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 description 1
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- 125000005023 xylyl group Chemical group 0.000 description 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)]
- C07F9/3804—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)
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3821—Acyclic saturated acids which can have further substituents on alkyl substituted by B, Si, P or a metal
-
- 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
- C07F9/553—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
- C07F9/59—Hydrogenated pyridine rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Physical Education & Sports Medicine (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US89135592A | 1992-05-29 | 1992-05-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ252587A true NZ252587A (en) | 1997-02-24 |
Family
ID=25398040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ252587A NZ252587A (en) | 1992-05-29 | 1993-05-11 | Phosphonate compounds; quaternary nitrogen containing compounds and pharmaceutical compositions containing them |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0642517A1 (zh) |
| JP (1) | JPH07507305A (zh) |
| KR (1) | KR950701927A (zh) |
| CN (1) | CN1085906A (zh) |
| AU (1) | AU675224B2 (zh) |
| CA (1) | CA2136819A1 (zh) |
| CZ (1) | CZ296694A3 (zh) |
| FI (1) | FI945598A (zh) |
| HU (1) | HUT69732A (zh) |
| IL (1) | IL105831A0 (zh) |
| MX (1) | MX9303245A (zh) |
| NZ (1) | NZ252587A (zh) |
| RU (1) | RU94046139A (zh) |
| SK (1) | SK144594A3 (zh) |
| WO (1) | WO1993024494A1 (zh) |
| ZA (1) | ZA933758B (zh) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5728650A (en) * | 1993-10-07 | 1998-03-17 | Zeneca Limited | Herbicidal aza bisphosphonic acids and compositions containing the same |
| IL115041A0 (en) * | 1995-08-23 | 1995-12-08 | Yissum Res Dev Co | Novel bisphosphonates process for their preparation and pharmaceutical compositions containing them |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2534391C2 (de) * | 1975-08-01 | 1983-01-13 | Henkel KGaA, 4000 Düsseldorf | 1-Hydroxy-3-aminoalkan-1,1-diphosphonsäuren |
| DE4011777A1 (de) * | 1989-04-14 | 1990-10-18 | Ciba Geigy Ag | N-trisubstituierte aminoalkandiphosphonsaeuren |
-
1993
- 1993-05-11 WO PCT/US1993/004469 patent/WO1993024494A1/en not_active Application Discontinuation
- 1993-05-11 RU RU94046139/04A patent/RU94046139A/ru unknown
- 1993-05-11 NZ NZ252587A patent/NZ252587A/en unknown
- 1993-05-11 CA CA002136819A patent/CA2136819A1/en not_active Abandoned
- 1993-05-11 CZ CZ942966A patent/CZ296694A3/cs unknown
- 1993-05-11 KR KR1019940704304A patent/KR950701927A/ko not_active Application Discontinuation
- 1993-05-11 EP EP93911255A patent/EP0642517A1/en not_active Ceased
- 1993-05-11 JP JP6500570A patent/JPH07507305A/ja active Pending
- 1993-05-11 HU HU9403406A patent/HUT69732A/hu unknown
- 1993-05-11 SK SK1445-94A patent/SK144594A3/sk unknown
- 1993-05-11 AU AU42453/93A patent/AU675224B2/en not_active Ceased
- 1993-05-28 IL IL105831A patent/IL105831A0/xx unknown
- 1993-05-28 ZA ZA933758A patent/ZA933758B/xx unknown
- 1993-05-29 CN CN93108225A patent/CN1085906A/zh active Pending
- 1993-05-31 MX MX9303245A patent/MX9303245A/es unknown
-
1994
- 1994-11-28 FI FI945598A patent/FI945598A/fi unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CZ296694A3 (en) | 1995-12-13 |
| FI945598A (fi) | 1995-01-25 |
| FI945598A0 (fi) | 1994-11-28 |
| HU9403406D0 (en) | 1995-02-28 |
| IL105831A0 (en) | 1993-09-22 |
| RU94046139A (ru) | 1996-09-27 |
| AU4245393A (en) | 1993-12-30 |
| JPH07507305A (ja) | 1995-08-10 |
| KR950701927A (ko) | 1995-05-17 |
| HUT69732A (en) | 1995-09-28 |
| EP0642517A1 (en) | 1995-03-15 |
| MX9303245A (es) | 1994-05-31 |
| WO1993024494A1 (en) | 1993-12-09 |
| CA2136819A1 (en) | 1993-12-09 |
| AU675224B2 (en) | 1997-01-30 |
| ZA933758B (en) | 1994-01-20 |
| SK144594A3 (en) | 1995-07-11 |
| CN1085906A (zh) | 1994-04-27 |
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