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)
- Catalysts (AREA)
- Treating Waste Gases (AREA)
- Ultra Sonic Daignosis Equipment (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 (pt) |
| EP (1) | EP0463560B1 (pt) |
| JP (1) | JP3222487B2 (pt) |
| KR (1) | KR100219315B1 (pt) |
| AT (1) | ATE129500T1 (pt) |
| AU (1) | AU641772B2 (pt) |
| CA (1) | CA2045077C (pt) |
| DE (1) | DE59106756D1 (pt) |
| DK (1) | DK0463560T3 (pt) |
| ES (1) | ES2079520T3 (pt) |
| FI (1) | FI101705B (pt) |
| GR (1) | GR3017895T3 (pt) |
| HR (1) | HRP940512A2 (pt) |
| HU (1) | HUT59148A (pt) |
| IE (1) | IE69314B1 (pt) |
| IL (3) | IL114631A (pt) |
| NO (1) | NO302476B1 (pt) |
| NZ (2) | NZ247934A (pt) |
| PT (1) | PT98064B (pt) |
| SI (1) | SI9111099B (pt) |
| YU (1) | YU109991A (pt) |
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| 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 |
| 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 |
| AU744189B2 (en) * | 1997-06-23 | 2002-02-14 | Neuro Therapeutics Limited | Neurologically-active compounds |
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| SE9904508D0 (sv) * | 1999-12-09 | 1999-12-09 | Astra Ab | New 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 |
| JP2007509974A (ja) * | 2003-10-31 | 2007-04-19 | アルザ・コーポレーシヨン | ３−アミノプロピル−ｎ−ブチルホスフィン酸の増大した吸収のための組成物および薬用量形態 |
| GB0327186D0 (en) * | 2003-11-21 | 2003-12-24 | Novartis Ag | Organic compounds |
| US7566738B2 (en) * | 2004-11-03 | 2009-07-28 | 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 |
| WO2008033572A1 (en) * | 2006-09-15 | 2008-03-20 | Xenoport, Inc. | Acyloxyalkyl carbamate prodrugs, methods of synthesis and use |
| WO2010051883A1 (de) | 2008-11-05 | 2010-05-14 | Clariant International Ltd | Verfahren zur herstellung von dialkylphosphinsäuren, -estern und -salzen mittels allylalkoholen/acroleinen und ihre verwendung |
| 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 |
| 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 |
| 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 |
| 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 |
| DE102008056342A1 (de) | 2008-11-07 | 2010-05-12 | Clariant International Limited | Verfahren zur Herstellung von Dialkylphosphinsäuren, -estern und -salzen mittels Acrylnitrilen und ihre Verwendung |
| EP2367835B1 (de) | 2008-11-11 | 2013-12-11 | Clariant Finance (BVI) Limited | Verfahren zur herstellung von mono-allylfunktionalisierten dialkylphosphinsäuren, deren salze und ester mit allylischen verbindungen 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 |
| 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 |
| 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 |
| 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 |
| US9181487B2 (en) | 2008-12-18 | 2015-11-10 | Clariant Finance (Bvi) Limited | Process for preparing ethylenedialkylphosphinic acids, esters and salts by means of acetylene and use thereof |
| DE102008063640A1 (de) * | 2008-12-18 | 2010-06-24 | Clariant International Limited | Verfahren zur Herstellung von gemischtsubstituierten Dialkylphosphinsäuren, -estern und -salzen 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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| US3784590A (en) * | 1969-01-02 | 1974-01-08 | Merck & Co Inc | Hydroxy and imino containing phosphonic acid diesters |
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| SU463675A1 (ru) * | 1973-12-04 | 1975-03-15 | Казанский Химико-Технологический Институт Им.С.М.Кирова | Способ получени -фосфорилированных нитроалканолов |
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| US4466913A (en) * | 1981-06-30 | 1984-08-21 | Maiji Seika Kaisha Ltd. | Phosphorus-containing compounds and process for producing the same |
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| US4536355A (en) * | 1982-10-08 | 1985-08-20 | Zoecon Corporation | Phenoxyphenylaminoalkylphosphinates useful in weed control |
| SU1174438A1 (ru) * | 1984-05-21 | 1985-08-23 | МГУ им.М.В.Ломоносова | Способ получени алкокси-(триметилсилокси)фосфинов |
| GB8425872D0 (en) * | 1984-10-12 | 1984-11-21 | Ciba Geigy Ag | Chemical compounds |
| US5243062A (en) * | 1984-10-12 | 1993-09-07 | Ciba-Geigy Corporation | Substituted propane-phosphonous acid compounds |
| US4740322A (en) * | 1985-07-29 | 1988-04-26 | The Lubrizol Corporation | Sulfur-containing compositions, and additive concentrates, lubricating oils, metal working lubricants and asphalt compositions containing same |
| US4657899A (en) * | 1986-04-09 | 1987-04-14 | Nova Pharmaceutical Corporation | Antagonists of specific excitatory amino acid neurotransmitter receptors |
| US4740332A (en) * | 1986-05-12 | 1988-04-26 | E. R. Squibb & Sons, Inc. | Process for preparing phosphonous acids |
| 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 |
| JPH0651709B2 (ja) * | 1987-12-09 | 1994-07-06 | 明治製菓株式会社 | 新規ホスフィン酸誘導体およびそれを有効成分とする脳循環代謝改善剤 |
| GB8820266D0 (en) * | 1988-08-26 | 1988-09-28 | Smith Kline French Lab | Compounds |
| 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 |
-
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 FI FI912998A patent/FI101705B/fi active
- 1991-06-19 DE DE59106756T patent/DE59106756D1/de not_active Expired - Fee Related
- 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
- 1991-06-19 ES ES91110074T patent/ES2079520T3/es not_active Expired - Lifetime
- 1991-06-19 EP EP91110074A patent/EP0463560B1/de not_active Expired - Lifetime
- 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 NZ NZ238636A patent/NZ238636A/en unknown
- 1991-06-20 CA CA002045077A patent/CA2045077C/en not_active Expired - Fee Related
- 1991-06-21 IE IE215891A patent/IE69314B1/en unknown
- 1991-06-21 NO NO912429A patent/NO302476B1/no not_active IP Right Cessation
- 1991-06-21 JP JP15064791A patent/JP3222487B2/ja not_active Expired - Fee Related
- 1991-06-21 PT PT98064A patent/PT98064B/pt not_active IP Right Cessation
- 1991-06-21 KR KR1019910010289A patent/KR100219315B1/ko not_active IP Right Cessation
- 1991-06-21 YU YU109991A patent/YU109991A/sh unknown
- 1991-06-21 AU AU79220/91A patent/AU641772B2/en not_active Ceased
- 1991-06-21 SI SI9111099A patent/SI9111099B/sl unknown
-
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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