SI9111099B - Process for preparation of araliphatically n-substituted aminoalkanephosphinic acids - Google Patents
Process for preparation of araliphatically n-substituted aminoalkanephosphinic acids Download PDFInfo
- Publication number
- SI9111099B SI9111099B SI9111099A SI9111099A SI9111099B SI 9111099 B SI9111099 B SI 9111099B SI 9111099 A SI9111099 A SI 9111099A SI 9111099 A SI9111099 A SI 9111099A SI 9111099 B SI9111099 B SI 9111099B
- Authority
- SI
- Slovenia
- Prior art keywords
- alkyl
- hydroxy
- phosphinic acid
- propyl
- salts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 43
- 238000002360 preparation method Methods 0.000 title claims abstract 5
- 239000002253 acid Substances 0.000 title claims 4
- 150000007513 acids Chemical class 0.000 title claims 2
- 150000003839 salts Chemical class 0.000 claims abstract 41
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 33
- 239000001257 hydrogen Substances 0.000 claims abstract 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 29
- 150000002431 hydrogen Chemical class 0.000 claims abstract 17
- 229910052736 halogen Inorganic materials 0.000 claims abstract 14
- 150000002367 halogens Chemical class 0.000 claims abstract 14
- 150000001875 compounds Chemical class 0.000 claims abstract 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 11
- 206010034759 Petit mal epilepsy Diseases 0.000 claims abstract 3
- 206010015037 epilepsy Diseases 0.000 claims abstract 2
- -1 C--C4-alkoxy Chemical group 0.000 claims 15
- 125000001544 thienyl group Chemical group 0.000 claims 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims 5
- 125000006239 protecting group Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 2
- 125000000217 alkyl group Chemical group 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
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- SKPCXBBLVIIRSY-HNNXBMFYSA-N (4-chlorophenyl)methyl-[(2s)-3-[(3,4-dichlorophenyl)methylamino]-2-hydroxypropyl]phosphinic acid Chemical compound C([C@H](O)CP(O)(=O)CC=1C=CC(Cl)=CC=1)NCC1=CC=C(Cl)C(Cl)=C1 SKPCXBBLVIIRSY-HNNXBMFYSA-N 0.000 claims 1
- MLEZXJMWOIHWDM-KRWDZBQOSA-N (4-chlorophenyl)methyl-[(2s)-3-[(4-chlorophenyl)methylamino]-2-hydroxypropyl]phosphinic acid Chemical compound C([C@H](O)CP(O)(=O)CC=1C=CC(Cl)=CC=1)NCC1=CC=C(Cl)C=C1 MLEZXJMWOIHWDM-KRWDZBQOSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- UJUFOUVXOUYYRG-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)ethanamine Chemical compound CC(N)C1=CC=C(Cl)C(Cl)=C1 UJUFOUVXOUYYRG-UHFFFAOYSA-N 0.000 claims 1
- ZSWKCGLIENVNON-UHFFFAOYSA-N 3-[(2,4-dichlorophenyl)methylamino]propyl-(diethoxymethyl)phosphinic acid Chemical compound CCOC(OCC)P(O)(=O)CCCNCC1=CC=C(Cl)C=C1Cl ZSWKCGLIENVNON-UHFFFAOYSA-N 0.000 claims 1
- PWJPVWNGRGJWGS-UHFFFAOYSA-N 3-[(2-chlorophenyl)methylamino]propyl-(diethoxymethyl)phosphinic acid Chemical compound CCOC(OCC)P(O)(=O)CCCNCC1=CC=CC=C1Cl PWJPVWNGRGJWGS-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- GKQYUKHULDZHJN-UHFFFAOYSA-N 3-[(3-chloro-4-iodophenyl)methylamino]propyl-(diethoxymethyl)phosphinic acid Chemical compound CCOC(OCC)P(O)(=O)CCCNCC1=CC=C(I)C(Cl)=C1 GKQYUKHULDZHJN-UHFFFAOYSA-N 0.000 claims 1
- IEUYIKWNRLIURQ-UHFFFAOYSA-N 3-[(3-chlorophenyl)methylamino]propyl-(diethoxymethyl)phosphinic acid Chemical compound CCOC(OCC)P(O)(=O)CCCNCC1=CC=CC(Cl)=C1 IEUYIKWNRLIURQ-UHFFFAOYSA-N 0.000 claims 1
- PCYWOXATQLNRFU-UHFFFAOYSA-N 3-[(4-chloro-3-iodophenyl)methylamino]propyl-(diethoxymethyl)phosphinic acid Chemical compound CCOC(OCC)P(O)(=O)CCCNCC1=CC=C(Cl)C(I)=C1 PCYWOXATQLNRFU-UHFFFAOYSA-N 0.000 claims 1
- GVWYUGDBZPZCCA-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl-methylamino]propyl-(diethoxymethyl)phosphinic acid Chemical compound CCOC(OCC)P(O)(=O)CCCN(C)CC1=CC=C(Cl)C=C1 GVWYUGDBZPZCCA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- MYKIJSRPIOTISR-UHFFFAOYSA-N 3-[1-(4-chlorophenyl)ethylamino]propyl-(diethoxymethyl)phosphinic acid Chemical compound CCOC(OCC)P(O)(=O)CCCNC(C)C1=CC=C(Cl)C=C1 MYKIJSRPIOTISR-UHFFFAOYSA-N 0.000 claims 1
- RZAUIDBBCKNJKN-UHFFFAOYSA-N C(CC)P(O)(=O)C1OCCC1 Chemical compound C(CC)P(O)(=O)C1OCCC1 RZAUIDBBCKNJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
- GPMWTSVCVROROH-UHFFFAOYSA-N CCOC(OCC)P(O)=O Chemical compound CCOC(OCC)P(O)=O GPMWTSVCVROROH-UHFFFAOYSA-N 0.000 claims 1
- VJPSXQDGJKPAQK-UAIPMZCESA-N ClC=1C=C(CC([C@@H](CP(O)(=O)CC2CC=CCC2)O)N)C=CC1Cl Chemical compound ClC=1C=C(CC([C@@H](CP(O)(=O)CC2CC=CCC2)O)N)C=CC1Cl VJPSXQDGJKPAQK-UAIPMZCESA-N 0.000 claims 1
- BJDMWTDZAPAKHF-SNVBAGLBSA-N OCCCP(O)(=O)C[C@@H]1CC=CCC1 Chemical compound OCCCP(O)(=O)C[C@@H]1CC=CCC1 BJDMWTDZAPAKHF-SNVBAGLBSA-N 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
- VEPDLZVVQZPWQJ-HNNXBMFYSA-N [(2s)-3-[(3,4-dichlorophenyl)methylamino]-2-hydroxypropyl]-[(3,4-dimethoxyphenyl)methyl]phosphinic acid Chemical compound C1=C(OC)C(OC)=CC=C1CP(O)(=O)C[C@@H](O)CNCC1=CC=C(Cl)C(Cl)=C1 VEPDLZVVQZPWQJ-HNNXBMFYSA-N 0.000 claims 1
- DKLQVPIATJRCFL-INIZCTEOSA-N [(2s)-3-[(3,4-dichlorophenyl)methylamino]-2-hydroxypropyl]-[(4-methylphenyl)methyl]phosphinic acid Chemical compound C1=CC(C)=CC=C1CP(O)(=O)C[C@@H](O)CNCC1=CC=C(Cl)C(Cl)=C1 DKLQVPIATJRCFL-INIZCTEOSA-N 0.000 claims 1
- WTQAUFMHCSXPKQ-GTPINHCMSA-N [(2s)-3-[(4-chlorophenyl)methylamino]-2-hydroxypropyl]-(4-methoxycyclohexyl)phosphinic acid Chemical compound C1CC(OC)CCC1P(O)(=O)C[C@@H](O)CNCC1=CC=C(Cl)C=C1 WTQAUFMHCSXPKQ-GTPINHCMSA-N 0.000 claims 1
- WFTNLWMVNFEQAX-KRWDZBQOSA-N [(2s)-3-[(4-chlorophenyl)methylamino]-2-hydroxypropyl]-[(3,4-dimethoxyphenyl)methyl]phosphinic acid Chemical compound C1=C(OC)C(OC)=CC=C1CP(O)(=O)C[C@@H](O)CNCC1=CC=C(Cl)C=C1 WFTNLWMVNFEQAX-KRWDZBQOSA-N 0.000 claims 1
- QPABBRWIPSHTLG-KRWDZBQOSA-N [(2s)-3-[(4-chlorophenyl)methylamino]-2-hydroxypropyl]-[(4-methoxyphenyl)methyl]phosphinic acid Chemical compound C1=CC(OC)=CC=C1CP(O)(=O)C[C@@H](O)CNCC1=CC=C(Cl)C=C1 QPABBRWIPSHTLG-KRWDZBQOSA-N 0.000 claims 1
- FBLVZVJFTCBCSV-SFHVURJKSA-N [(2s)-3-[(4-chlorophenyl)methylamino]-2-hydroxypropyl]-[(4-methylphenyl)methyl]phosphinic acid Chemical compound C1=CC(C)=CC=C1CP(O)(=O)C[C@@H](O)CNCC1=CC=C(Cl)C=C1 FBLVZVJFTCBCSV-SFHVURJKSA-N 0.000 claims 1
- WPHULXBMTBGVSX-YUZLPWPTSA-N [(2s)-3-[1-(3,4-dichlorophenyl)ethylamino]-2-hydroxypropyl]-(diethoxymethyl)phosphinic acid Chemical compound CCOC(OCC)P(O)(=O)C[C@@H](O)CNC(C)C1=CC=C(Cl)C(Cl)=C1 WPHULXBMTBGVSX-YUZLPWPTSA-N 0.000 claims 1
- 230000003556 anti-epileptic effect Effects 0.000 claims 1
- 239000001961 anticonvulsive agent Substances 0.000 claims 1
- 229960003965 antiepileptics Drugs 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- JJFYYCBNGQCREI-QGZVFWFLSA-N benzyl-[(2r)-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-QGZVFWFLSA-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
- ODENYXJMEKJPGA-HNNXBMFYSA-N benzyl-[(2s)-3-[(3-chloro-4-iodophenyl)methylamino]-2-hydroxypropyl]phosphinic acid Chemical compound C([C@H](O)CP(O)(=O)CC=1C=CC=CC=1)NCC1=CC=C(I)C(Cl)=C1 ODENYXJMEKJPGA-HNNXBMFYSA-N 0.000 claims 1
- JUOVCPHAFXJVKX-AWEZNQCLSA-N benzyl-[(2s)-3-[(4,5-dichloro-2-iodophenyl)methylamino]-2-hydroxypropyl]phosphinic acid Chemical compound C([C@H](O)CP(O)(=O)CC=1C=CC=CC=1)NCC1=CC(Cl)=C(Cl)C=C1I JUOVCPHAFXJVKX-AWEZNQCLSA-N 0.000 claims 1
- CYEXRUNXQBAIFH-HNNXBMFYSA-N benzyl-[(2s)-3-[(4-chloro-3-iodophenyl)methylamino]-2-hydroxypropyl]phosphinic acid Chemical compound C([C@H](O)CP(O)(=O)CC=1C=CC=CC=1)NCC1=CC=C(Cl)C(I)=C1 CYEXRUNXQBAIFH-HNNXBMFYSA-N 0.000 claims 1
- NQNSMMBTNHUINE-INIZCTEOSA-N benzyl-[(2s)-3-[(4-chloro-3-methoxyphenyl)methylamino]-2-hydroxypropyl]phosphinic acid Chemical compound C1=C(Cl)C(OC)=CC(CNC[C@H](O)CP(O)(=O)CC=2C=CC=CC=2)=C1 NQNSMMBTNHUINE-INIZCTEOSA-N 0.000 claims 1
- YUBRYSPHOZLWJZ-IBYPIGCZSA-N benzyl-[(2s)-4-(4-chloroanilino)-2-hydroxypentyl]phosphinic acid Chemical compound C([C@@H](O)CC(C)NC=1C=CC(Cl)=CC=1)P(O)(=O)CC1=CC=CC=C1 YUBRYSPHOZLWJZ-IBYPIGCZSA-N 0.000 claims 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- PHIBEYMUALDAQI-UHFFFAOYSA-N benzylphosphinic acid Chemical compound OP(=O)CC1=CC=CC=C1 PHIBEYMUALDAQI-UHFFFAOYSA-N 0.000 claims 1
- RAGWAGJHCBJGIV-UHFFFAOYSA-N butyl-[3-[(4-chlorophenyl)methylamino]propyl]phosphinic acid Chemical compound CCCCP(O)(=O)CCCNCC1=CC=C(Cl)C=C1 RAGWAGJHCBJGIV-UHFFFAOYSA-N 0.000 claims 1
- 229960000623 carbamazepine Drugs 0.000 claims 1
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 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
- VGEXYWCEAOBBPU-UHFFFAOYSA-N cyclopropylmethyl-[3-[(3,4-dichlorophenyl)methylamino]propyl]phosphinic acid Chemical compound C1CC1CP(=O)(O)CCCNCC1=CC=C(Cl)C(Cl)=C1 VGEXYWCEAOBBPU-UHFFFAOYSA-N 0.000 claims 1
- WOFMXLHACUSRKL-HNNXBMFYSA-N diethoxymethyl-[(2s)-2-hydroxy-3-(2-phenylethylamino)propyl]phosphinic acid Chemical compound CCOC(OCC)P(O)(=O)C[C@@H](O)CNCCC1=CC=CC=C1 WOFMXLHACUSRKL-HNNXBMFYSA-N 0.000 claims 1
- ZAUYNZDEMRYOMJ-UHFFFAOYSA-N diethoxymethyl-[3-(2-phenylethylamino)propyl]phosphinic acid Chemical compound CCOC(OCC)P(O)(=O)CCCNCCC1=CC=CC=C1 ZAUYNZDEMRYOMJ-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 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 1
- 229960005318 vigabatrin Drugs 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 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
- C07F9/30—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
-
- 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)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- 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 (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH209290 | 1990-06-22 | ||
| CH44091 | 1991-02-13 | ||
| CH119991 | 1991-04-22 | ||
| YU109991A YU109991A (sh) | 1990-06-22 | 1991-06-21 | Aralifatske n-substituisane aminoalkanfosfinske kiseline i postupak za njihovo pripremanje |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI9111099A SI9111099A (sl) | 1998-02-28 |
| SI9111099B true SI9111099B (en) | 2001-06-30 |
Family
ID=27172107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9111099A SI9111099B (en) | 1990-06-22 | 1991-06-21 | Process for preparation of araliphatically n-substituted aminoalkanephosphinic acids |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US5229379A (ja) |
| EP (1) | EP0463560B1 (ja) |
| JP (1) | JP3222487B2 (ja) |
| KR (1) | KR100219315B1 (ja) |
| AT (1) | ATE129500T1 (ja) |
| AU (1) | AU641772B2 (ja) |
| CA (1) | CA2045077C (ja) |
| DE (1) | DE59106756D1 (ja) |
| DK (1) | DK0463560T3 (ja) |
| ES (1) | ES2079520T3 (ja) |
| FI (1) | FI101705B1 (ja) |
| GR (1) | GR3017895T3 (ja) |
| HR (1) | HRP940512A2 (ja) |
| HU (1) | HUT59148A (ja) |
| IE (1) | IE69314B1 (ja) |
| IL (3) | IL114631A (ja) |
| NO (1) | NO302476B1 (ja) |
| NZ (2) | NZ238636A (ja) |
| PT (1) | PT98064B (ja) |
| SI (1) | SI9111099B (ja) |
| YU (1) | YU109991A (ja) |
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| WO1997011953A1 (en) * | 1995-09-28 | 1997-04-03 | 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 |
| WO1998058939A1 (en) * | 1997-06-23 | 1998-12-30 | Polychip Pharmaceuticals Pty. Ltd. | Neurologically-active compounds |
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| AR045794A1 (es) * | 2003-09-23 | 2005-11-16 | Aventis Pharma Inc | Procedimiento para preparar derivados de acido 3- amino-2- hidroxipropilfosfinico |
| EP1677758A1 (en) * | 2003-10-31 | 2006-07-12 | ALZA Corporation | Compositions and dosage forms for enhanced absorption of 3-amino-n-butyl-phosphinic acid |
| 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 |
| US7494985B2 (en) * | 2004-11-03 | 2009-02-24 | Xenoport, Inc. | Acyloxyalkyl carbamate prodrugs, methods of synthesis, and use |
| US7585996B2 (en) * | 2006-09-15 | 2009-09-08 | Xenoport, Inc. | Acyloxyalkyl carbamate prodrugs, methods of synthesis and use |
| 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 |
| 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 |
| 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 |
| 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 |
| DE102008056228A1 (de) * | 2008-11-06 | 2010-05-12 | Clariant International Limited | Verfahren zur Herstellung von monoaminofunktionalisierten Dialkylphosphinsäuren, deren Salze und Ester und ihre Verwendung |
| EP2352740B1 (de) | 2008-11-07 | 2014-09-24 | Clariant Finance (BVI) Limited | 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 |
| DE102008056339A1 (de) * | 2008-11-07 | 2010-05-12 | Clariant International Limited | Verfahren zur Herstellung von mono-aminofunktionalisierten Dialkylphosphinsäuren, -estern und -salzen 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 |
| US8772519B2 (en) | 2008-11-11 | 2014-07-08 | Clariant Finance (Bvi) Limited | Process for preparing mono-allyl-functionalized dialkylphosphinic acids, salts and esters thereof with allylic compounds, and the use thereof |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| ES2446666T3 (es) | 2008-12-18 | 2014-03-10 | Clariant Finance (Bvi) Limited | Procedimiento para la preparación de ácidos etilen-dialquil-fosfínicos, o de sus ésteres y sales, mediante acetileno, y su utilización |
| 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 |
| 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 DK DK91110074.1T patent/DK0463560T3/da not_active Application Discontinuation
- 1991-06-19 DE DE59106756T patent/DE59106756D1/de not_active Expired - Fee Related
- 1991-06-19 FI FI912998A patent/FI101705B1/fi active
- 1991-06-19 EP EP91110074A patent/EP0463560B1/de not_active Expired - Lifetime
- 1991-06-19 AT AT91110074T patent/ATE129500T1/de not_active IP Right Cessation
- 1991-06-19 ES ES91110074T patent/ES2079520T3/es not_active Expired - Lifetime
- 1991-06-20 NZ NZ238636A patent/NZ238636A/en unknown
- 1991-06-20 CA CA002045077A patent/CA2045077C/en not_active Expired - Fee Related
- 1991-06-20 US US07/718,503 patent/US5229379A/en not_active Expired - Lifetime
- 1991-06-20 HU HU912064A patent/HUT59148A/hu unknown
- 1991-06-20 NZ NZ247934A patent/NZ247934A/en unknown
- 1991-06-21 JP JP15064791A patent/JP3222487B2/ja not_active Expired - Fee Related
- 1991-06-21 IE IE215891A patent/IE69314B1/en unknown
- 1991-06-21 PT PT98064A patent/PT98064B/pt not_active IP Right Cessation
- 1991-06-21 SI SI9111099A patent/SI9111099B/sl unknown
- 1991-06-21 YU YU109991A patent/YU109991A/sh unknown
- 1991-06-21 AU AU79220/91A patent/AU641772B2/en not_active Ceased
- 1991-06-21 KR KR1019910010289A patent/KR100219315B1/ko not_active IP Right Cessation
- 1991-06-21 NO NO912429A patent/NO302476B1/no 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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