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)
Claims (38)
1 PATENTNI ZAHTEVKI I. Postopek za pripravo novih aralifatsko N-substituiranih aminoalkanfosfinskih kislin s formulo I HO R OII R.
CH- -N / I \ Π. R„ R, (I), v kateri pomenijo, Ru RT, R?' in R.i vodik. R: predstavlja vodik ali hidroksi, R^ pomeni v fenilnem oz naftilnem delu s CrC4-alkilom. Ci-C4-alkoksi. hidroksi in ali halogenom mono-, di- ali trisubstituiran fenil-C|-C4-alkilm. difenil-Ci-Ca-alkilni ali naftil-CrCj-alkilm ostanek ali nesubstituiran ali v tienilnem, funlnem oz piridilnem delu s halogenom substituiran tienil-, furil- ali piridil-Ci-C4-alkilni ostanek, R, predstavlja vodik, Ci-C4-alkil ali skupino R4 in R pomeni (V-CValkil, C:-C4-alkenil, C2-C7-alkinil, okso-C2-C7-alkil, hidroksi-C2-C7-alkil ali dihidroksi-C2-C?-alkil, a-hidroksi-C3-C5-alkenil, mono-, di- ali trifluor-C2-C5-aIkil, mono-, di- ali trifluor-C2-Cj-alkenil, mono-, di- ali trifluor-a-hidroksi-C2-C5-alkil, mono-, di- ali trifluor-a-hidroksi-C2-C5-alkenil, C|-C4-alkoksi-CrC4-alkiI, di-C|-C4-alkoksi-C|-C4-alkil, Cr C4-alkoksi C1-C4-alkoksi-C2-C7-(hidroksi)-alkil, C|-C4-alkoksi-C2-C<.-(halo)-alkil, Cr C4-alkiltio-CrC4-alkil, di-C^C^-aLkiltio-C|-C4-alkiI, CrCg-cikloalkil, a-hidroksi-Cr C^-cikloalkil, oksa- ali tia-Cj-C^-cikloalkil, 1,3-dioksa- ali l,3-ditia-C3-C8-cUdoalkil, ί C3-C8-cikloalkil-CrC4-alkil, C3-C8-cikloalkenil-C|-C4-alkiI, mono-, di- ali trihidroksi-C3-C8-cikloalkenil, C3-C6-cikloalkil-(hidroksi)-Ci-C4-alkil, l-(C|-C4-alkiltio-C3-C6-cikloalkil)-l-hidroksi)-C|-C4-alkil, nesubstituiran ali s C|-C4-alkilom, Ci-C4-alkoksi, halogenom, hidroksi in/ali trifluorometilom mono-, di- ali trisubstituiran mono- ali difenil-CrC4-alkil, naftil-CiATi-alkil l ali nesubstituiran ali s halogenom substituiran tienil-, furil- ali piridil-CrC4-alkil, in njihovih soli, označen s tem, da v spojini s formulo II O R, R10 R, QR.°OI I I I A'—c-C CH-" k h R -N \ (II). R. ? v kateri pomenijo R,, R,', R2’ in R3 vodik, R^ stoji za zaščitno skupino za hidroksi, R8 stoji za skupino Rs ali za zaščitno skupino za amtno in Ri0 za vodik ali zaščiten hidroksi, pri čemer imajo R, Rt, R4 in R5 navedeni pomen, ali v njem soli z nadomestitvijo zaščitne skupine za hidroksi R^, z vodikom sprostimo hidroksi skupine in v danem primeru odcepimo zaščitno skupino za amino R8 in v danem primeru iz zaščitene hidroksi skupine R|() sprostimo hidroksi skupine R2 m po želji dobljeno spojino prevedemo v drugo spojino s formulo 1, izomemo zmes. ki se jo da dobiti v smislu postopka, ločimo v komponente in ločimo vsakokrat prednostni izomer ίη/ali prosto spojino, ki sejo da dobiti v smislu postopka, prevedemo v sol ali sol, ki sejo da dobiti v smislu postopka, v ustrezno prosto spojino.
2 Postopek po zahtevku 1, označen s tem, da pripravimo spojine s formulo l, v kateri pomenijo R|, R/, R2' in R3 vodik, R2 predstavlja vodik ali hidroksi, Rj pomeni s Cr C4-alkilom, CrC4-alkoksi, hidroksi ιη/ali halogenoin substituiran fenil- ali naftil-C(-Cj-alkilni ostanek ali nesubstituiran ali s halogenoin substituiran tienil-, furil- ali piridil-Ci-C4-aLkilni ostanek, R5 predstavlja vodik, nižji alkil ali skupino Rj in R pomeni C2-C4-alkil, C2-C4-alkenil, C2-C7-alkmil, okso-C2-C7-alkil, hidroksi-C2-C7-alkil ali dihidroksi-C2-C7-alkil, a-hidroksi-C3-C3-alkenil, mono-, di- ali mono- di- ali trifluor-C2-C5-alkil, mono-, di- ali trifluor-CVCs-alkeml, mono-, di- ali tnfluor-a-hidroksi-C2-C5-alkil, mono-, di- ali tnfluor-a-hidroksi-C2-C5-alkenil, C|-C4-alkoksi-CrC4-alkil, di-C|-C4-alkoksi-Ci-C4-alkil, Ci-C4-alkoksi-C2-C7-(hidroksi)-alkil, C1-C4-alkoksi-C2-C5-(halo)-alkil, C|-C4-alkiltio-C|-C4-alkiI, di-Ci-C4-alkiltio-Ci-C4-alkil, C3-C8-cikloalkil, a-hidroksi-C3-C6-cikloalkil, oksa- ali tia-C3-C6-cikloalkil, 1,3-dioksa- ali l,3-ditia-C3-C8-cikloalkil, C3-C6-cikloalkil-(hidroksi)-C|-C4-alkil, l-(Cr C4-alkiltio-C3-C6-cikloalkil)-l-hidroksi)-Ci-C4-alkil ali nesubstituiran ali s CrC4-alkilom, C(-C4-alkoksi, hidroksi m/ali halogenom subsriuiran feniI-Ci-C4-alkil ali naftil-CrC4-alkil, in njihove soli.
3. Postopek po zahtevku 1, označen s tem, da pripravimo spojine s formulo I, v kateri pomeni R C3-C7-alkil, a,a-di-Ci-C4-alkoksi-CrC4-alkil, C3-C6-cikloalkil-Ci-C4-alkil, C3-C6-cikloalkeniI-C|-C4-alkil, mono-, di- ali trihidroksi-C3-C6-cikloalkil-CrC4-alkil 3 ali nesubstituiran ali s CrC4-alkilom, Ci-C4-alkoksi, hidroksi in/ali halogenom mono-, di- ali trisubstituiran benzil, R2 predstavlja vodik ali hidroksi, R|, RT, R2' in R3 pomenijo vodik, R4 predstavlja s CrC4-alkilom, CrC4-alkoksi in/ali halogenom mono-, di- ali trisubstituiran fenil- ali difeml-C|-C4-alkil ali nesubstituiran ali s halogenom z atomskim številom do vključno 35 monosubstituiran naftil-C|-C4-alkil m Rs pomeni vodik, CrC4-alkil ali skupino R^ m njihove soli
4 Postopek po zahtevku 1, označen s tem, da pripravimo spojine s formulo I, v kateri pomenijo R|, R|', R2' m R3 vodik, R2 predstavlja vodik ali hidroksi, R^ predstavlja s C|-C4-alkilom ali Ci-C4-alkoksi monosubstituiran ali s halogenom z atomskim številom do vključno 35 mono- ali disubstituiran fenil-CrC4-alkil ali nesubstituiran ali s halogenom z atomskim številom do vključno 35 monosubstituiran naftil-, tienil-, furil- ali piridil-Ci-C4-alkiL R5 pomeni vodik, CrC4-alkil ali skupino in R pomeni C3-C7-alkil, a,a-di-CrC4-alkoksi-Ci-C4-alkil, C3-C6-cikloalkil-C|-C4-alkil ali nesubstituiran ali s C|-C4-alkilom, CrC4-alkoksi ali halogenom z atomskim številom do vključno 35 substituiran benzil, m njihove soli.
5 Postopek po zahtevku 1, označen s tem, da pripravimo spojine s formulo l, v kateri Ri, R|', R2' in R3 pomenijo vodik, R2 predstavlja vodik ali hidroksi, predstavlja s halogenom z atomskim številom do vključno 35 mono- ali disubstituiran a-feml-Cr t4-alkil ali nesubstituiran oc-naftil-C|-C4-alkil, a-tienil-Ci-C4-alkil, a-furil-Ci-C4-alkil ali a-piridil-CrC4-alkil, R3 pomeni vodik, CrC4-alkil ali skupino R4 m R pomeni C3-Cj-alkil, a,a-di-C)-C4-alkoksimetil, C3-C6-cikloalkil-C|-C4-alkil, a-(C3-C6-cikloalkeml)-Ci-C4-alkil, a-(mono-, di- ali trihidroksi-C3-C6-cikloalkil)-C|-C4-alkil ali benzil, in njihove soli.
6. Postopek po zahtevku 1, označen s tem, da pripravimo spojine s formulo I, v kateri pomenijo Rj, Rf, R2' in R3 vodik, R2 predstavlja vodik ali hidroksi, R4 predstavlja s halogenom z atomskim številom do vključno 35 mono- ali disubstituiran fenil-Ci-C4-alkil ali nesubstituiran naftil-, tienil-, furil- ali piridil-C i-C4-alkil, R5 pomeni vodik, 4 CrGralkil ali skupino R4, in R pomeni C3-C5-alkil, a,a-di-CrC4-aLkoksimetil, C3-C6-cikloalkil-Cj-C4-alkil ali benzil, m njihove soli.
7. Postopek po zahtevku 1, označen s tem. da pripravimo 3-(p- klorbenzilamino)propil(dietoksimetil)fosfinsko kislino ali eno od njenih soh
8. Postopek po zahtevku 1, označen s tem, da pripravimo 3-(p-klorbenzilamino-2(S)-hidroksipropil(benzil)fosfinsko kislino ali eno od njenih soli
9. Postopek po zahtevku 1, označen s tem, da pripravimo 3-(p- klorbenzilamino)propil(n-butil)fbsfinsko kislino ali eno od njenih soli
10. Postopek po zahtevku 1, označen s tem, da pripravimo 3-(p- klorbenzilamino)propil(cikloheksilmetil)fosfmsko kislino ali eno od njenih soli
11. Postopek po zahtevku 1, označen s tem, da pripravimo 3-(p-klorbenzilamino)-2(R)-hidroksipropil(benziI)fosfinsko kislino ali eno od njenih soli.
12 Postopek po zahtevku 1, označen s tem, da pripravimo 3-(3,4- diklorbenzilamino)propil(dietoksimetiI)fosfinsko kislino ali eno od njenih soli i
13. Postopek po zahtevku 1, označen s tem, da pripravimo 3-[l-(p- klorfenil)etilamino]propil(dietoksimetil)fosfinsko kislino ali eno od njenih soli
14. Postopek po zahtevku 1, označen s tem, da pripravimo 3-(naftil- l-ilmetilamino)-propil(dietoksimetil)fosfinsko kislino ali eno od njenih soli.
15. Postopek po zahtevku 1, označen s tem, da pripravimo 3-(3,4- diklorbenzilamino)propil(cikloheksilmetil)fosfinsko kislino ali eno od njenih soli. 5
16. Postopek po zahtevku 1, označen s tem, da pripravimo 3-(pirid-2-ilmetilammo)-2(S)-hidroksipropil(benzil)fosfmsko kislino ali eno od njenih soli
17. Postopek po zahtevku 1. označen s tem. da pripravimo 3-(p-klorbenzilammoiI)-2(S)-hidroksipropil(cikloheksiImetiI)fosfinsko kislino ali eno od njenih soli.
18 Postopek po zahtevku 1. označen s tem, da pripravimo 3-(3,4-diklorbenzilaminoil)-2(S)-hidroksipropil(benzil)fosfinsko kislino ali eno od njenih soli.
19. Postopek po zahtevku 1, označen s tem, da pripravimo 3-(p- fluorbenzilarruno)propil(dietoksimetil)fosfinsko kislmo ali eno od njenih soli.
20. Postopek po zahtevku 1, označen s tem, da pripravimo 3-(4-klor-3-trifluormetilbenzilamino)propil(dietoksunetil)fosfinsko kislino ali eno od njenih soli.
21 Postopek po zahtevku 1, označen s tem, da pripravimo 3-(m- klorbenzilamino)propil(dietoksimetil)fosfinsko kislmo ali eno od njenih soli.
22. Postopek po zahtevku 1, označen s tem, da pripravimo 3-(3,4-diklorbenzilamino)-2(S)-hidroksipropil(cikloheksilmetiI)fosfinsko kislmo ali eno od njenih soli
23. Postopek po zahtevku 1, označen s tem, da pripravimo 3-[1-(3,4-diklorfenil)etilamino]propil(dietoksimetil)fosfinsko kislmo ali eno od njenih soli
24. Postopek po zahtevku 1, označen s tem, da pripravimo 3-[ l-(p-kJorfenil)amino-etil]-2(S)-hidroksipropil(benzil)fosfinsko kislino ali eno od njenih soli.
25. Postopek po zahtevku 1, označen s tem, da pripravimo 3-(p- jodbenzilamino)propil(dietoksimetil)fosfmsko kislino ali eno od njenih soli. 6
26. Postopek po zahtevku 1, označen s tem, da popravimo 3-(2,4- diklorbenzilammo)propil(dietoksimetil)fosfinsko kislino ali eno od njenih soli
27. Postopek po zahtevku 1, označen s tem, da pripravimo 3-(o- klorbenzilamino)propil(dietoksimetil)fosfinsko kislino ah eno od njenih soh.
28. Postopek po zahtevku 1, označen s tem. da pripravimo 3-(3,4- diklorbenzilamino)propil(ciklopropilmetil)fosfinsko kislino ah eno od njenih soh.
29 Postopek po zahtevku 1, označen s tem, da pripravimo 3-(p- k]orbenzilamino)propil(tetrahidrofuran-2-il)fosfinsko kislino ah eno od njenih soh
30. Postopek po zahtevku 1, označen s tem, da pripravimo 3-[N-(p-klorbenzil)-N-metilamino]propil(dietoksimetil)fosfinsko kislino ah eno od njenih soli.
31. Postopek po zahtevku 1, označen s tem, da pripravimo 3-(p-kIorbenzilamino)-2(S)-hidroksipropil(p-metilbenzil)fosfinsko kislino ah eno od njenih soli.
32 Postopek po zahtevku 1, označen s tem, da pripravimo 3-(3,4-diklorbenzilamino)-2(S)-hidroksipropil(p-metilbenzil)fosfinsko kislino ah eno od njenih soli. i
33. Postopek po zahtevku 1, označen s tem, da pripravimo 3-(p-klorbenzilamino)-2(S)-hidroksi-propil(p-klorbenzil)fosfinsko kislino ah eno od njenih soli.
34 Postopek po zahtevku 1, označen s tem, da pripravuno 3-(3,4-diklorbenzilamino)-2(S)-hidroksipropil(p-klorbenzil)fosfinsko kislino ali eno od njenih soli.
35. Postopek po zahtevku 1, označen s tem, da pripravimo 3-(p-klorbenzilamino)-2(S)-hidroksi-propil(dietoksimetil)fosfmsko kislino; 3-[l-(p-klorfenil)etilamino]-2(S)-hidroksi-propil(dietoksimetil)fosfmsko kislino; 3-(3,4-diklorbenzilamino)-2(S)-hidroksi-propil(dietoksimetil)fosfinsko kislino; 3-[l-(3,4-diklorfenil)etilamino]-2(S)-hidroksi-propil(dietoksimetil)fosfmsko kislino; 7 3-[N-(p-klorbenzil)-N-metil-amino]-2(S)-hidroksi-propil(benzil)fosfinsko kislino; 3-(p-klorbenzilannno)-2(S)-hidroksi-propil(p-metoksibenzil)fosfinsko kislino; 3-(p-klorbenzilamino)-2(S)-hidroksi-propil(3,4-dimetoksibenzil)fosfinsko kislino; 3-(3,4-diklorbenzilamino)-2(S)-hidroksi-propil(3,4-dimetoksibenzil)fosfinsko kislino; 3-[2-(p-klorfenil)prop-2-ilamino]propil(dietoksiinetil)fosfinsko kislino, 3-(2-(3,4-diklorfenil)prop-2-ilamino]propil(dietoksunetil)fosfinsko kislino; 3-[2-(p-klorfenil)prop-2-ilamino]-2(S)-hidiOksi-propiI(benzil)fosfinsko kislino, 3-[2-(3,4-diklorfenil)prop-2-ilammo)-2(S)-hidroksi-propil(benzil)fosfinsko kislino; 3-(3,4-diklorbenzilamino)-2-(S)-hidroksi-piOpil(3,4,5-tnhidroksicikloheksil-metil)fosfinsko kislino; 3-(4-klor-3-metoksi-benziIamino)propil(dietoksimetil (fosfmsko kislino, 3-(4-klor-3-metoksi-benzilamino)-2(S)-hidroksi-propiI(benzil)fosfinsko kislino; 3-(2-feniletilamino)propil(dietoksimetil)fosfinsko kislino; 3-(2-feniletilamino)-2(S)-hidroksi-propil(dietoksimetil)fosfinsko kislino; 3-(p-klorbenzilamino-2(S)-hidroksi-propil(4-metoksicikloheksil)fosfinsko kislino; 3-(3,4-diklor-6-jod-benzilamino)-2(S)-hidroksi-propil(benzil)fosfinsko kislino; 3-(3,4-diklor-6-jod-benzilamino)propil(dietoksimetil)fosfinsko kislino; 3-(4-klor-3-jod-benzilamino)propil(dietoksimetil)fosfinsko kislino; 3-(3-klor-4-jod-benziIamino)propiI(dietoksimetil)fosfinsko kislino, 3-(4-klor-3-jod-benzilamino)-2(S)-hidroksi-propil(benzil)fosfinsko kislino; 3-(3-klor-4-jod-benzilamino)-2(S)-hidroksi-propil(benzil)fosfinsko kislino; 3-di-(p-klorbenzil)aminopropil(dietoksimetil)fosfinsko kislino, 3-di-(3,4-diklorbenzil)amino-2(S)-hidroksi-propil(benzil)fosfinsko kislino, 3-(m-klorbenzilamino)-2(S)-hidroksi-propil(benzil)fosfinsko kislino; 3-(3,4-diklorbenziI)amino-2(S)-hidroksi-propil(cis-4,5-dihidroksicikloheksilmetil)-fosfmsko kislino; 3-(3,4-diklorbenzil)amino-2(S)-hidroksi-propil(cikloheks-3-enilmetil)fosfinsko kislino; 3jl-(3,4-diklorfenil)etilamincj-2(S)-hidiOksi-propil(cikloheks-3-enilmetil)fosfinska kislina ali 3 jl-(3,4-diklorferLil)etilamin^-2(S)-hidroksi-propil(cis-4,5-dihidroksicildoheksilrnetil)-fosfmsko kislino ali vsakokrat njeno sol. 8
36. Postopek za pripravo farmacevtskih pripravkov, označen s tem, da spojino s formulo 1 8 H Os R' O R, Ro R, -C — c- •CH — N. /R· \ R/ R,’ R„ (D. v kateri pomenijo R|. Rf, R2’ in R5 vodik, R2 predstavlja vodik ali hidroksi, R4 pomeni nesubstituiran ali v fenilnem oz. naftilnem delu s C|-C4-alkilom. CrC4-alkoksi, hidroksi in7ali halogenom mono-, di- ali trisubstituiran feniI-CrC4-alkilni. difeml-Cr C4-alkilni ali naftil-C|-C4-alkilni ostanek ali nesubstituiran ali v tiemlnem, furilnem oz piridilnem delu s halogenom substitULran tiemi-. furil- ali piridil-CrC4-alkilni ostanek, R5 predstavlja vodik, CrC4-alkil ali skupino R4 m R pomeni C2-C4-alkil, C2-C4-alkenil, C2-C7-alkinil, okso-C2-C7-alkil, hjdroksi-C2-C7-alkil ali dihidroksi-C2-C7-alkil, a-hidroksi-CrC5-alkenil, mono-, di- ali tnfluor-CVCValkil, mono-, di- ali trifluor-CrC.s-alkeml, mono-, di- ali trifluor-a-hjdroksi-C2-C5-alkil, mono-, di- ali trifluor-a-hidroksi-C2-C5-alkeml, Ci-Cj-alkoksi-Ci-Ca-alkil, di-C|-C4-alkoksi-Ci-C4-alkil, C|-C4-alkoksi-C|-C4-alkoksi-C2-C7-(hidroksi)-alkil, Ci-C4-alkoksi-C2-C0-(halo)-alkil, C|-C4-alkiltio-C|-C4-alkil, di-Ci-C4-alkiltio-C1-C4-alkil, CrCs-cikloalkil, a-hidroksi-Ci-Cfi-cikloalkil, oksa- ali tia-C3-C6-cikIoalkil, 1,3-dioksa- ali l,3-ditia-C3-Cg-cikloalkil, C3-C8-crkloalkjl-CrC4-alkil, C3-Cg-cikloalkenil-C|-C4-alkil, mono-, di-ali tnhidroksi-C3-C8-cikloalkenil, C3-C6-cikloalkil-(hidroksi)-Ci-C4-alkil, l-(CrC4-alkiltio-C3-C6-cildoalkil)-l-hidroksi)-Ci-C4-alkil, nesubstituiran ali s C|-C4-alkilom, C|-C4-alkoksi, halogenom, hidroksi in/ali trifluormetilom mono-, di- ali trisubstituiran mono- ali difem!-CrC4-alkil, naftil-Ci-C4-alkil ali nesubstituiran ali s halogenom substituiran tiemi, furil ali piridil-Ci-C4-alkil, v prosti obliki ali v obliki farmacevtsko uporabnih soli pomešamo z običajnimi farmacevtskimi pomožnimi snovmi.
37. Postopek po zahtevku 36 za pripravo farmacevtskih pripravkov, označen s tem, da spojmo po enem od zahtevkov 1 do 35 v prosti obliki ali v obliki farmacevtsko uporabnih soli pomešamo z običajnimi farmacevtskimi pomožnimi snovmi. 9
38. Postopek po zahtevku 36 ali 37, označen s tem, da pripravimo farmacevtske pripravke, določene za zdravljenje epilepsij bolezenskih oblik "petit mal" kot tudi za preprečevanje stanj, podobnih "petit mal", ki lahko nastopijo pri zdravljenju s femtoinom. karbamazepinom, Vigabatrinom@ in antiepileptiki z enakim ali podobnim profilom učinka
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| Application Number | Priority Date | Filing Date | Title |
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| 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 |
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| SI9111099B true SI9111099B (en) | 2001-06-30 |
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| EP (1) | EP0463560B1 (sl) |
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| DK (1) | DK0463560T3 (sl) |
| ES (1) | ES2079520T3 (sl) |
| FI (1) | FI101705B (sl) |
| GR (1) | GR3017895T3 (sl) |
| HR (1) | HRP940512A2 (sl) |
| HU (1) | HUT59148A (sl) |
| IE (1) | IE69314B1 (sl) |
| IL (3) | IL98502A (sl) |
| NO (1) | NO302476B1 (sl) |
| NZ (2) | NZ238636A (sl) |
| PT (1) | PT98064B (sl) |
| SI (1) | SI9111099B (sl) |
| YU (1) | YU109991A (sl) |
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| 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 |
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| EP1677757A2 (en) * | 2003-10-31 | 2006-07-12 | Alza Corporation | Compositions and dosage forms for enhanced absorption |
| 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 |
| 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 |
| 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 |
| 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 |
| DE102008056339A1 (de) | 2008-11-07 | 2010-05-12 | Clariant International Limited | Verfahren zur Herstellung von mono-aminofunktionalisierten Dialkylphosphinsäuren, -estern und -salzen und ihre Verwendung |
| CN102171226B (zh) | 2008-11-11 | 2015-02-11 | 科莱恩金融(Bvi)有限公司 | 利用烯丙基化合物制备单烯丙基官能化的二烷基次膦酸、其盐或酯的方法以及它们的用途 |
| 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 |
| 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 |
| 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 |
| 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 |
| DE102008064003A1 (de) | 2008-12-19 | 2010-06-24 | Clariant International Limited | Verfahren zur Herstellung von mono-funktionalisierten 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 |
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| EP0093081B1 (de) * | 1982-04-23 | 1986-03-19 | Ciba-Geigy Ag | Herbizide und pflanzenwuchsregulierende Mittel |
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| GB8728483D0 (en) * | 1987-12-04 | 1988-01-13 | Ciba Geigy Ag | Chemical compounds |
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| 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 IL98502A patent/IL98502A/en not_active IP Right Cessation
- 1991-06-14 IL IL11463191A patent/IL114631A/en not_active IP Right Cessation
- 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 DE DE59106756T patent/DE59106756D1/de not_active Expired - Fee Related
- 1991-06-19 ES ES91110074T patent/ES2079520T3/es not_active Expired - Lifetime
- 1991-06-19 FI FI912998A patent/FI101705B/fi active
- 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 US US07/718,503 patent/US5229379A/en not_active Expired - Lifetime
- 1991-06-20 NZ NZ247934A patent/NZ247934A/en unknown
- 1991-06-20 HU HU912064A patent/HUT59148A/hu unknown
- 1991-06-20 CA CA002045077A patent/CA2045077C/en not_active Expired - Fee Related
- 1991-06-21 PT PT98064A patent/PT98064B/pt not_active IP Right Cessation
- 1991-06-21 AU AU79220/91A patent/AU641772B2/en not_active Ceased
- 1991-06-21 IE IE215891A patent/IE69314B1/en unknown
- 1991-06-21 JP JP15064791A patent/JP3222487B2/ja not_active Expired - Fee Related
- 1991-06-21 NO NO912429A patent/NO302476B1/no not_active IP Right Cessation
- 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 YU YU109991A patent/YU109991A/sh 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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