NO302476B1 - Analogifremgangsmåte for fremstilling av aralifatiske N-substituerte aminoalkanfosfinsyrer - Google Patents
Analogifremgangsmåte for fremstilling av aralifatiske N-substituerte aminoalkanfosfinsyrer Download PDFInfo
- Publication number
- NO302476B1 NO302476B1 NO912429A NO912429A NO302476B1 NO 302476 B1 NO302476 B1 NO 302476B1 NO 912429 A NO912429 A NO 912429A NO 912429 A NO912429 A NO 912429A NO 302476 B1 NO302476 B1 NO 302476B1
- Authority
- NO
- Norway
- Prior art keywords
- propyl
- hydroxy
- phosphinic acid
- alkyl
- hydrogen
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 32
- 230000008569 process Effects 0.000 title claims abstract description 11
- 239000002253 acid Substances 0.000 title claims description 27
- 150000007513 acids Chemical class 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 150000003839 salts Chemical class 0.000 claims abstract description 53
- 239000001257 hydrogen Substances 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 19
- -1 3-[1-(p-chlorophenyl)-aminoethyl]-2(S)-hydroxy-propyl (benzyl)-phosphinic acid Chemical compound 0.000 claims description 25
- 125000006239 protecting group Chemical group 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000007858 starting material Substances 0.000 claims description 12
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical group O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- INZLCQIVKAUPBT-UHFFFAOYSA-N 3-[(4-chlorophenyl)methylamino]propyl-(diethoxymethyl)phosphinic acid Chemical compound CCOC(OCC)P(O)(=O)CCCNCC1=CC=C(Cl)C=C1 INZLCQIVKAUPBT-UHFFFAOYSA-N 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
- GJZVQXWEIYRHBE-UHFFFAOYSA-N 3-[(3,4-dichlorophenyl)methylamino]propyl-(diethoxymethyl)phosphinic acid Chemical compound CCOC(OCC)P(O)(=O)CCCNCC1=CC=C(Cl)C(Cl)=C1 GJZVQXWEIYRHBE-UHFFFAOYSA-N 0.000 claims description 2
- GLKKTGWXWNOWPJ-UHFFFAOYSA-N 3-[1-(3,4-dichlorophenyl)ethylamino]propyl-(diethoxymethyl)phosphinic acid Chemical compound CCOC(OCC)P(O)(=O)CCCNC(C)C1=CC=C(Cl)C(Cl)=C1 GLKKTGWXWNOWPJ-UHFFFAOYSA-N 0.000 claims description 2
- JJFYYCBNGQCREI-KRWDZBQOSA-N benzyl-[(2s)-3-[(4-chlorophenyl)methylamino]-2-hydroxypropyl]phosphinic acid Chemical compound C([C@H](O)CP(O)(=O)CC=1C=CC=CC=1)NCC1=CC=C(Cl)C=C1 JJFYYCBNGQCREI-KRWDZBQOSA-N 0.000 claims description 2
- KLCOFMAFXDCDDG-UHFFFAOYSA-N diethoxymethyl-[3-[(4-fluorophenyl)methylamino]propyl]phosphinic acid Chemical compound CCOC(OCC)P(O)(=O)CCCNCC1=CC=C(F)C=C1 KLCOFMAFXDCDDG-UHFFFAOYSA-N 0.000 claims description 2
- ZBQRSDDBLGMYLP-KRWDZBQOSA-N [(2S)-3-[(4-chlorophenyl)methylamino]-2-hydroxypropyl]-(cyclohexylmethyl)phosphinic acid Chemical compound ClC1=CC=C(CNC[C@@H](CP(O)(=O)CC2CCCCC2)O)C=C1 ZBQRSDDBLGMYLP-KRWDZBQOSA-N 0.000 claims 1
- DQTXREZQTSRRTI-INIZCTEOSA-N benzyl-[(2s)-2-hydroxy-3-(pyridin-2-ylmethylamino)propyl]phosphinic acid Chemical compound C([C@H](O)CP(O)(=O)CC=1C=CC=CC=1)NCC1=CC=CC=N1 DQTXREZQTSRRTI-INIZCTEOSA-N 0.000 claims 1
- 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 1
- MBDYVJOTAGXSHX-HNNXBMFYSA-N cyclohexylmethyl-[(2s)-3-[(3,4-dichlorophenyl)methylamino]-2-hydroxypropyl]phosphinic acid Chemical compound C([C@H](O)CP(O)(=O)CC1CCCCC1)NCC1=CC=C(Cl)C(Cl)=C1 MBDYVJOTAGXSHX-HNNXBMFYSA-N 0.000 claims 1
- CQYJDQPPTXXOTE-UHFFFAOYSA-N cyclohexylmethyl-[3-[(3,4-dichlorophenyl)methylamino]propyl]phosphinic acid Chemical compound C1CCCCC1CP(=O)(O)CCCNCC1=CC=C(Cl)C(Cl)=C1 CQYJDQPPTXXOTE-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 18
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- 150000002367 halogens Chemical class 0.000 abstract description 8
- 150000002431 hydrogen Chemical class 0.000 abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 5
- 206010015037 epilepsy Diseases 0.000 abstract description 4
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- 206010034759 Petit mal epilepsy Diseases 0.000 abstract description 2
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- 241000700159 Rattus Species 0.000 description 21
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- 238000006243 chemical reaction Methods 0.000 description 17
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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- KPYSYYIEGFHWSV-UHFFFAOYSA-N Baclofen Chemical compound OC(=O)CC(CN)C1=CC=C(Cl)C=C1 KPYSYYIEGFHWSV-UHFFFAOYSA-N 0.000 description 10
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
- WJOMGDVVBPDSRV-UHFFFAOYSA-N 3-[diethoxymethyl(ethoxy)phosphoryl]propan-1-amine Chemical compound CCOC(OCC)P(=O)(OCC)CCCN WJOMGDVVBPDSRV-UHFFFAOYSA-N 0.000 description 6
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
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- BEUJIYDGMCASAZ-WHUIICBVSA-N (2r)-1-[benzyl(ethoxy)phosphoryl]-3-chloropropan-2-ol Chemical compound ClC[C@H](O)CP(=O)(OCC)CC1=CC=CC=C1 BEUJIYDGMCASAZ-WHUIICBVSA-N 0.000 description 4
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Classifications
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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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/36—Amides thereof
-
- 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
- C07F9/30—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
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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
- A61P25/08—Antiepileptics; Anticonvulsants
- A61P25/10—Antiepileptics; Anticonvulsants for petit-mal
-
- 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
- C07F9/58—Pyridine rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
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- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Treating Waste Gases (AREA)
- Ultra Sonic Daignosis Equipment (AREA)
- Catalysts (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH209290 | 1990-06-22 | ||
| CH44091 | 1991-02-13 | ||
| CH119991 | 1991-04-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO912429D0 NO912429D0 (no) | 1991-06-21 |
| NO912429L NO912429L (no) | 1991-12-23 |
| NO302476B1 true NO302476B1 (no) | 1998-03-09 |
Family
ID=27172107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO912429A NO302476B1 (no) | 1990-06-22 | 1991-06-21 | Analogifremgangsmåte for fremstilling av aralifatiske N-substituerte aminoalkanfosfinsyrer |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US5229379A (xx) |
| EP (1) | EP0463560B1 (xx) |
| JP (1) | JP3222487B2 (xx) |
| KR (1) | KR100219315B1 (xx) |
| AT (1) | ATE129500T1 (xx) |
| AU (1) | AU641772B2 (xx) |
| CA (1) | CA2045077C (xx) |
| DE (1) | DE59106756D1 (xx) |
| DK (1) | DK0463560T3 (xx) |
| ES (1) | ES2079520T3 (xx) |
| FI (1) | FI101705B (xx) |
| GR (1) | GR3017895T3 (xx) |
| HR (1) | HRP940512A2 (xx) |
| HU (1) | HUT59148A (xx) |
| IE (1) | IE69314B1 (xx) |
| IL (3) | IL114631A (xx) |
| NO (1) | NO302476B1 (xx) |
| NZ (2) | NZ238636A (xx) |
| PT (1) | PT98064B (xx) |
| SI (1) | SI9111099B (xx) |
| YU (1) | YU109991A (xx) |
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| US5567840A (en) * | 1989-05-13 | 1996-10-22 | Ciba-Geigy Corporation | Substituted aminoalkylphosphinic acids |
| EP0767174A1 (de) * | 1991-11-21 | 1997-04-09 | Ciba-Geigy Ag | Neue Aminoalkanphosphinsäuren und ihre Salze |
| GB9125615D0 (en) * | 1991-12-02 | 1992-01-29 | Wyeth John & Brother Ltd | Amines |
| AU662404B2 (en) * | 1992-05-08 | 1995-08-31 | Novartis Ag | Novel N-aralkyl- and N-heteroaralkyl-aminoalkanephosphinic acids |
| DE4407197A1 (de) * | 1994-03-04 | 1995-09-07 | Hoechst Schering Agrevo Gmbh | Verfahren zur Herstellung von /L/-Homoalanin-4-yl-(methyl)phosphinsäure und deren Salze durch Racematspaltung |
| AU7130196A (en) * | 1995-09-28 | 1997-04-17 | Novartis Ag | Novel hydroxylated and alkoxylated N- and/or P-aralkylphosphinic acid derivatives |
| DE19634706A1 (de) * | 1996-08-28 | 1998-03-05 | Hoechst Ag | Verfahren zur Herstellung von 2-Cyanoethyl-phosphinsäureestern |
| EP1000071B1 (en) * | 1997-06-23 | 2004-11-17 | Polychip Pharmaceuticals Pty. Ltd. | Gaba-c receptor antagonists for stimulating memory capacity |
| JP3382159B2 (ja) * | 1998-08-05 | 2003-03-04 | 株式会社東芝 | 情報記録媒体とその再生方法及び記録方法 |
| US7319095B2 (en) * | 1999-12-09 | 2008-01-15 | Astrazeneca Ab | Use of GABAB receptor agonists |
| SE9904508D0 (sv) * | 1999-12-09 | 1999-12-09 | Astra Ab | New compounds |
| WO2004083855A1 (en) * | 2003-03-19 | 2004-09-30 | Solvo Biotechnology, Inc. | Method for the identification of cells specifically modulating slow inhibition in the neocortex |
| AR045794A1 (es) * | 2003-09-23 | 2005-11-16 | Aventis Pharma Inc | Procedimiento para preparar derivados de acido 3- amino-2- hidroxipropilfosfinico |
| EP1677759A1 (en) * | 2003-10-31 | 2006-07-12 | Alza Corporation | Compositions and dosage forms for enhanced absorption of gabapentin and pregabalin |
| GB0327186D0 (en) | 2003-11-21 | 2003-12-24 | Novartis Ag | Organic compounds |
| WO2006050471A2 (en) * | 2004-11-03 | 2006-05-11 | Xenoport, Inc. | Acyloxyalkyl carbamate prodrugs of sulfinic acids, methods of synthesis, and use |
| WO2006050472A2 (en) * | 2004-11-03 | 2006-05-11 | Xenoport, Inc. | Acyloxyalkyl carbamate prodrugs of 3-aminopropylphosphonous and -phosphinic acids |
| WO2008033572A1 (en) * | 2006-09-15 | 2008-03-20 | Xenoport, Inc. | Acyloxyalkyl carbamate prodrugs, methods of synthesis and use |
| DE102008055916A1 (de) | 2008-11-05 | 2010-05-06 | Clariant International Limited | Verfahren zur Herstellung von mono-hydroxyfunktionalisierten Dialkylphosphinsäuren, -estern und -salzen mittels Allylalkoholen und ihre Verwendung |
| CN102177164B (zh) | 2008-11-05 | 2015-02-11 | 科莱恩金融(Bvi)有限公司 | 利用烯丙醇/丙烯醛制备二烷基次膦酸、二烷基次膦酸酯和二烷基次膦酸盐的方法,以及它们的用途 |
| DE102008055914A1 (de) | 2008-11-05 | 2010-05-06 | Clariant International Limited | Verfahren zur Herstellung von mono-hydroxyfunktionalisierten Dialkylphosphinsäuren, -estern und -salzen mittels Acroleinen und ihre Verwendung |
| DE102008056228A1 (de) * | 2008-11-06 | 2010-05-12 | Clariant International Limited | Verfahren zur Herstellung von monoaminofunktionalisierten Dialkylphosphinsäuren, deren Salze und Ester und ihre Verwendung |
| DE102008056234A1 (de) * | 2008-11-06 | 2010-05-12 | Clariant International Ltd. | Verfahren zur Herstellung von momo-carboxyfunktionalisierten Dialkylphosphinsäuren, -estern und -salzen mittels Vinylen/Nitrilen und ihre Verwendung |
| DE102008056341A1 (de) | 2008-11-07 | 2010-05-12 | Clariant International Limited | Verfahren zur Herstellung von monoaminofunktionalisierten Dialkylphosphinsäuren, -estern und -salzen mittels Acrylnitrilen und ihre Verwendung |
| DE102008056339A1 (de) * | 2008-11-07 | 2010-05-12 | Clariant International Limited | Verfahren zur Herstellung von mono-aminofunktionalisierten Dialkylphosphinsäuren, -estern und -salzen und ihre Verwendung |
| WO2010051893A1 (de) | 2008-11-07 | 2010-05-14 | Clariant International Ltd | Verfahren zur herstellung von dialkylphosphinsäuren, -estern und -salzen mittels acrylsäurederivaten und ihre verwendung |
| DE102008056342A1 (de) | 2008-11-07 | 2010-05-12 | Clariant International Limited | Verfahren zur Herstellung von Dialkylphosphinsäuren, -estern und -salzen mittels Acrylnitrilen und ihre Verwendung |
| JP5743219B2 (ja) | 2008-11-11 | 2015-07-01 | クラリアント・ファイナンス・（ビーブイアイ）・リミテッド | アリル化合物を用いる、モノアリル官能性ジアルキルホスフィン酸、それらの塩およびエステルの製造方法およびそれらの使用 |
| DE102008060036A1 (de) | 2008-12-02 | 2010-06-10 | Clariant International Limited | Verfahren zur Herstellung von mono-carboxyfunktionalisierten Dialkylphosphinsäuren, -estern und -salzen mittels Vinylester einer Carbonsäure und ihre Verwendung |
| DE102008060035A1 (de) | 2008-12-02 | 2010-06-10 | Clariant International Limited | Verfahren zur Herstellung von mono-hydroxyfunktionalisierten Dialkylphosphinsäuren, -estern und -salzen mittels Vinylester einer Carbonsäure und ihre Verwendung |
| DE102008060535A1 (de) | 2008-12-04 | 2010-06-10 | Clariant International Limited | Verfahren zur Herstellung von mono-carboxyfunktionalisierten Dialkylphosphinsäuren, -estern und -salzen mittels Vinylether und ihre Verwendung |
| DE102008063640A1 (de) * | 2008-12-18 | 2010-06-24 | Clariant International Limited | Verfahren zur Herstellung von gemischtsubstituierten Dialkylphosphinsäuren, -estern und -salzen und ihre Verwendung |
| DE102008063627A1 (de) | 2008-12-18 | 2010-06-24 | Clariant International Limited | Verfahren zur Herstellung von monohydroxyfunktionalisierten Dialkylphosphinsäuren,-estern und -salzen mittels Ethylenoxid und ihre Verwendung |
| KR101697948B1 (ko) | 2008-12-18 | 2017-01-19 | 클라리언트 파이넌스 (비브이아이)리미티드 | 아세틸렌을 사용하는 에틸렌디알킬포스핀산, 에틸렌디알킬포스핀산 에스테르 및 에틸렌디알킬포스핀산 염의 제조방법 및 이의 용도 |
| DE102008063642A1 (de) | 2008-12-18 | 2010-06-24 | Clariant International Limited | Verfahren zur Herstellung von monocarboxyfunktionalisierten Dialkylphosphinsäuren, -estern und -salzen mittels Alkylenoxiden und ihre Verwendung |
| DE102008063668A1 (de) | 2008-12-18 | 2010-07-01 | Clariant International Limited | Verfahren zur Herstellung von Alkylphosponsäuren, -estern und -salzen mittels Oxidation von Alkylphosphonigsäuren und ihre Verwendung |
| DE102008064012A1 (de) | 2008-12-19 | 2010-06-24 | Clariant International Limited | Halogenfreie Addukte von Alkylphosphonigsäurederivaten und diesterbildenden Olefinen, halogenfreie Verfahren zu deren Herstellung und ihre Verwendung |
| DE102008064003A1 (de) | 2008-12-19 | 2010-06-24 | Clariant International Limited | Verfahren zur Herstellung von mono-funktionalisierten Dialkylphosphinsäuren, -estern und -salzen und ihre Verwendung |
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-
1991
- 1991-06-14 IL IL11463191A patent/IL114631A/en not_active IP Right Cessation
- 1991-06-14 IL IL98502A patent/IL98502A/en not_active IP Right Cessation
- 1991-06-19 DE DE59106756T patent/DE59106756D1/de not_active Expired - Fee Related
- 1991-06-19 FI FI912998A patent/FI101705B/fi active
- 1991-06-19 ES ES91110074T patent/ES2079520T3/es not_active Expired - Lifetime
- 1991-06-19 EP EP91110074A patent/EP0463560B1/de not_active Expired - Lifetime
- 1991-06-19 DK DK91110074.1T patent/DK0463560T3/da not_active Application Discontinuation
- 1991-06-19 AT AT91110074T patent/ATE129500T1/de not_active IP Right Cessation
- 1991-06-20 NZ NZ238636A patent/NZ238636A/en unknown
- 1991-06-20 HU HU912064A patent/HUT59148A/hu unknown
- 1991-06-20 US US07/718,503 patent/US5229379A/en not_active Expired - Lifetime
- 1991-06-20 NZ NZ247934A patent/NZ247934A/en unknown
- 1991-06-20 CA CA002045077A patent/CA2045077C/en not_active Expired - Fee Related
- 1991-06-21 JP JP15064791A patent/JP3222487B2/ja not_active Expired - Fee Related
- 1991-06-21 KR KR1019910010289A patent/KR100219315B1/ko not_active IP Right Cessation
- 1991-06-21 SI SI9111099A patent/SI9111099B/sl unknown
- 1991-06-21 AU AU79220/91A patent/AU641772B2/en not_active Ceased
- 1991-06-21 NO NO912429A patent/NO302476B1/no not_active IP Right Cessation
- 1991-06-21 IE IE215891A patent/IE69314B1/en unknown
- 1991-06-21 YU YU109991A patent/YU109991A/sh unknown
- 1991-06-21 PT PT98064A patent/PT98064B/pt not_active IP Right Cessation
-
1993
- 1993-05-03 US US08/056,726 patent/US5407922A/en not_active Expired - Lifetime
-
1994
- 1994-09-08 HR HR940512A patent/HRP940512A2/xx not_active Application Discontinuation
-
1995
- 1995-01-20 US US08/375,878 patent/US5545631A/en not_active Expired - Lifetime
- 1995-07-17 IL IL11463195A patent/IL114631A0/xx unknown
- 1995-10-26 GR GR950402941T patent/GR3017895T3/el unknown
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