KR930019685A - 치환된 아미노포스포네이트 유도체와 이의 제조방법 및 이를 함유하는 제약 조성물 - Google Patents
치환된 아미노포스포네이트 유도체와 이의 제조방법 및 이를 함유하는 제약 조성물 Download PDFInfo
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- KR930019685A KR930019685A KR1019930003335A KR930003335A KR930019685A KR 930019685 A KR930019685 A KR 930019685A KR 1019930003335 A KR1019930003335 A KR 1019930003335A KR 930003335 A KR930003335 A KR 930003335A KR 930019685 A KR930019685 A KR 930019685A
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- Prior art keywords
- butyl
- hydroxyphenyl
- tert
- aminomethylphosphate
- diethyl
- Prior art date
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- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical class NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 title claims abstract 5
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract 4
- 238000002360 preparation method Methods 0.000 title abstract 2
- -1 perfluoro Chemical group 0.000 claims 17
- 125000004432 carbon atom Chemical group C* 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- IAANMKMHMYZVOC-UHFFFAOYSA-N aminomethyl dihydrogen phosphate Chemical compound NCOP(O)(O)=O IAANMKMHMYZVOC-UHFFFAOYSA-N 0.000 claims 5
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 150000002466 imines Chemical class 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 229940086542 triethylamine Drugs 0.000 claims 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- BCXBKOQDEOJNRH-UHFFFAOYSA-N NOP(O)=O Chemical class NOP(O)=O BCXBKOQDEOJNRH-UHFFFAOYSA-N 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000001118 alkylidene group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- DALDUXIBIKGWTK-UHFFFAOYSA-N benzene;toluene Chemical compound C1=CC=CC=C1.CC1=CC=CC=C1 DALDUXIBIKGWTK-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 239000003610 charcoal Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- 125000006165 cyclic alkyl group Chemical group 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 235000012489 doughnuts Nutrition 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000012362 glacial acetic acid Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000002808 molecular sieve Substances 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 claims 1
- 150000002978 peroxides Chemical class 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
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- 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
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
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- A61K31/00—Medicinal preparations containing organic active ingredients
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- A61K31/661—Phosphorus acids or esters thereof not having P—C bonds, e.g. fosfosal, dichlorvos, malathion or mevinphos
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- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
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Abstract
본원은 하기식(I)의,-위치가 페닐그룹들로 치환된 신규 아미노포스포네 이트 유도체와 이의 제조방법 및 이를 함유하는 제약 조성물에 관한다.
식중, X1, X2, X3, R1, R2, A, B, Z 및 n는 청구범위 제1항에서 정의된 바와같음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (13)
- 알파위치가 페놀그룹으로 치환된 하기 일반식(I)의 아미노 포스포네이트 유도체.식중, X1, X2(동일하거나 또는 서로다른)는 H, 하이드록시그룹 또는 니트로그룹, 1 내지 8개의 탄소원자들을 지니는 직쇄 또는 분기쇄 알킬 또는 알콕시그룹, X3는 H, 1 내지 4개의 탄소원자들을 지니는 알킬 그룹이고, 이때 X3O와 두개의 다른 치환체들인 X1또는 X2가운데 하나는 1 내지 4개의 탄소원자들을 지니는 알킬리덴 디옥시환을 형성할 수도 있음.R1, R2(동일하거나 또는 서로 다른)는 H, 1내지 6개의 탄소원자들을 지니는 직쇄 또는 분기쇄 알킬 그룹 B는 CH2, CH2-CH2또는 CH=CH, n은 0 또는 1, Z는 H, 1 내지 8개의 탄소원자들을 지니는 직쇄 또는 분기쇄 알킬 그룹, 아실 그룹 R3-Co (R3는 1 내지 4개의 탄소원자들을 지니는 알킬그룹, 1 내지 4개의 탄소원자들을 지니는 퍼플루오로알킬 그룹).A는 H, CH2-CH=CH2, 1 내지 8개의 탄소원자들을 지니는 직쇄, 분기쇄 또는 환상알킬그룹, 또는 하기 그룹 가운데 선택된 그룹:식중, k는 2 내지 4의 정수, m은 0 내지 5의 정수, X4, X5, X6(동일하거나 또는 서로다른)는 H, 하이드록시그룹, 트리플루오로메틸그룹, 니트로그룹, 아미노그룹, 디메틸아미노그룹, 디에틸아미노그룹, 할로겐원자 (F, Cl, Br, I) 1 내지 8개의 탄소원자들을 지니는 직쇄 또는 분기쇄알킬 또는 알콕시그룹이고, 이때 X4와 X5는 1 내지 4개의 탄소원자들을 지니는 알킬리덴디옥시환을 형성할 수도 있음, X7는 H 또는 CH3, R은 1 내지 6개의 탄소원자들을 지니는 직쇄 또는 분기쇄 알킬그룹, 6 내지 9개의 탄소원자들을 지니는 아릴 또는 알킬아릴 그룹.
- 제1항에 있어서, 하기 일반식(I)의 화합물.식중 X3는 H 또는 1 내지 4개의 탄소원자들을 지니는 알킬그룹, 바람직스럽기로는 X3가 H, X1과 X2(동일하거나 또는 서로다른)는 1 내지 6개의 탄소원자들을 지니는 직쇄 또는 분기쇄알킬 그룹, 바람직스럽기로는 X1과 X2모두 t-부틸, R1과 R2는 각기 H 또는 1 내지 4개의 탄소원자들을 지니는 직쇄 또는 분기쇄 알킬 그룹, 바람직스럽기는 에틸, B는 CH2n은 0 또는 1, 바람직스럽기로는 n 가 0 z는 H, 1 내지 4개의 탄소원자들을 지니는 직쇄 또는 부기쇄 알킬 그룹, 아실그룹 R3-CO (R3는 C1-4알킬 그룹), 그리고 A는 H 또는 하기 그룹 가운데 선택되는 그룹 :식중, m, X4, X5, X6는 앞서 정의한 바와같음.
- 제1항에 있어서, 하기 일반식(I)의 화합물.식중, X1과 X2는 각기 터트-부틸 그룹, X3는 H R1과 R2는 각기 에틸 그룹, n은 0 z는 H 그리고 A는 하기 그룹가운데 선택되는 그룹 :X4, X5, X6및 m은 제1항에서 정의한 바와같음.
- 제1항에 있어서, 하기 그룹을 포함하는 그룹가운데서 선택되는 아미노포스포네이트 유도체.-디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-페닐-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(4-하이드록시페닐)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(4-클로로페닐)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(4-메톡시페닐)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(4-메틸페닐)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(4-에톡시페닐)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(4-펜틸페닐)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-[-4-(4-클로로프탈아미도)-3-메틸페닐]아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-벤질-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(2-페닐에틸)-아미노메틸포스네이트, -디메틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-[2-(4-하이드록시페닐)에틸]아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-[2-(4-클로로페닐)에틸]-아미노메틸포스네이트,-디에틸-(3,5-디-터드-부틸-4-하이드록시 페닐)-N-〔2-(4-클로로페닐)-에틸〕-아미노메틸포스네이트, -디프로필-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-[2-(4-클로로페닐)에틸]-아미노메틸포스네이트, -디이소프로필-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-[2-(4-클로로페닐)에틸]-아미노메틸포스네이트, -디메틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(3-페닐프로필)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(3-페닐프로필)-아미노메틸포스네이트, -디이소프로필-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(3-페닐프로필)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(4-페닐부틸)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(4-페닐에틸)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(2, 2, 6, 6-테트라메틸-4-피페리딜)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-피레로닐-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(3, 5-디-터트-부틸-4-하이드록시벤질)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(3-피콜일)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-[2-(2-피리딜)에틸)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(2-벤조티아졸일)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(1-페닐사이클로펜틸)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(3-피리딜)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(3-페닐프로필)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-메틸-N-(3-피콜일)- 아미노메틸포스네이트, -디메틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-아세틸-N-(3-페니프로필)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-아세틸-N-(3-페니프로필)-아미노메틸포스네이트, -디프로필-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-아세틸-N-(3-페니프로필)-아미노메틸포스네이트, -디이소프로필-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-아세틸-N-(3-페니프로필)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-메톡시페닐)-N-(3-페니프로필)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(3-페니프로필)-아미노메틸포스네이트, -디에틸-(3, 5-디-세크-부틸-4-하이드록시페닐)-N-(2-페니에틸)-아미노메틸포스네이트, -디에틸-(3, 5-디-이소프로필-부틸-4-하이드록시페닐)-N-(2-페니에틸)-아미노메틸포스네이트, -디에틸-(4-하이드록시페닐)-N-[2-(4-클로로페닐)에틸]-아미노메틸포스네이트, --(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(3-페니프로필)-아미노메틸포스폰산, -디-터트-부틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-[2-(4-클로로페닐) 에틸] 아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-알릴-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-벤질옥시카보닐-아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-(2, 2-디메틸-4-페닐-1, 3-디옥사-5-사이클로헥실) 아미노메틸포스네이트, -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-아세틸-N-[2-(2-피리딜)에틸]-아미노메틸포스네이트, 및 -디에틸-(3, 5-디-터트-부틸-4-하이드록시페닐)-N-헵타플루오로부티릴-N-(3-페니프로필) 아미노메틸포스네이트.
- 제1항에 있어서, 하기 일반식(Ⅳ)의 이민을 용매 또는 방향족 탄화수소 존재하 20° 내지 140°사이의 온도에서 하기 일반식(Ⅴ)의 디알킬 포스파이트와 반응시키는 것으로 이루어지는 일반식(I)의 아미노포스포네이트 제조방법.식중, X1, X2, X3, A, B R1, R2및 n는 제1항에 정의한 바와같음.
- 제5항에 있어서, 반응이 아민 (예컨대, 디에틸아민, 또는 트리에틸 아민과 같은)에 의해 촉매되는 방법.
- 제1항에서, 일반식(Ⅳ)의 아민을 하기 일반식(Ⅳ)의 시약 트리메틸실일-디알킬포스파이트 [할로겐화된 용매존재하, 0℃ 내지 30℃ 사이의 온도에서 클로로트리메틸실란, 디알킬포스파이트 및 트리에틸아민 사이에 원위치(in situ) 제조된]과 반응시키는 것으로 이루어지는 일반식(I)의 아미노메틸포스포네이트 에스테르 제조방법.
- 제5항에 있어서, 에테르, 테트라하이드로퓨란, 벤젠, 톨루엔, 에탄올과 같은 용매내에서, 하기 일반식(Ⅱ)의 알데하이드와 하기 일반식(Ⅲ) (식중, Z=H)의 1차 아민을 촉매로서 분자이시이브, 산 또는 염기 존재 또는 부재하, 0℃와 사용한 용매의 비등점 사이의 온도에서 축합 반응시킴으로서 일반식 Ⅳ의 이민을 얻는 방법.
- 제1항에 있어서, 일반식(I) (R1및 R2가 C1-4알킬 그룹인)의 아미노포스포네이트 에스테르를 진한 염산과 환류시켜 가수분해시키거나 또는 브로모트리메틸실란으로 가수분해시킨뒤, 수성 가수분해시키는 일반식(I) (R1=R2=H)의 아미노포스폰산의 제조방법.
- 제1항에 있어서, 3차 아민 존재하에 페트롤리움 에테르, 벤젠 톨루엔, 에테르, 테트라하이드로퓨란과 같은 용매내에서 당해 아미노포스포테이트 (1) (A 또는 Z 두 그룹중 최소한 한개는 H 인)를 일반식(Ⅶ)의 아실화제를 이용 아실화시키는 일반식(I)의 N-아실화도니 아미노포스포네이트 제조방법.
- 제1항에 있어서, 촉매로서 챠콜부착 팔라듐 또는 챠콜부착 팔라듐(Ⅱ)하이드록사이드를 그리고 용매로서 에탄올 또는 빙초산을 이용, 일반식(I)의 당해 아미노포스포네이트(Z=H이고 A는 1-페닐에틸, 1-페닐사이클로 펜틸과 같은-치환된 벤질 그룹 또는 벤질옥시카보닐 그룹인)를 촉매적 수소화 (catalytic hydrogenation)시키는 식(I)의 아미노포스포네이트(A=Z=H) 제조방법.
- 약제학적으로 용인되는 지지체와 컴비네이션시킨, 치료효과를 나타낼 수 있는 양의 제1항에 따른, 최소한 한개의 식(I) 아미노포스포네이트를 포함하는 제약 조성물.
- 제12항에 있어서, 혈장 콜레스테롤과 혈중 과산화물을 감소시켜주는 동맥경화증 치료용 제약 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH704/92A CH683996A5 (fr) | 1992-03-05 | 1992-03-05 | Dérivés aminophosphonates substitués, leur procédé de préparation et compositions pharmaceutiques les contenant. |
| US704/92 | 1992-03-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR930019685A true KR930019685A (ko) | 1993-10-18 |
Family
ID=4193232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019930003335A KR930019685A (ko) | 1992-03-05 | 1993-03-05 | 치환된 아미노포스포네이트 유도체와 이의 제조방법 및 이를 함유하는 제약 조성물 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5424303A (ko) |
| EP (1) | EP0559079B1 (ko) |
| JP (1) | JPH0649083A (ko) |
| KR (1) | KR930019685A (ko) |
| AT (1) | ATE156829T1 (ko) |
| AU (1) | AU662957B2 (ko) |
| CA (1) | CA2091031A1 (ko) |
| CH (1) | CH683996A5 (ko) |
| DE (1) | DE69312984T2 (ko) |
| DK (1) | DK0559079T3 (ko) |
| ES (1) | ES2108772T3 (ko) |
| FI (1) | FI930974A (ko) |
| GR (1) | GR3025268T3 (ko) |
| NO (1) | NO303783B1 (ko) |
| NZ (1) | NZ247056A (ko) |
| SG (1) | SG43831A1 (ko) |
| ZA (1) | ZA931473B (ko) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4433244A1 (de) * | 1994-09-19 | 1996-03-28 | Hoechst Ag | Aminomethylphosphon- und Aminomethylphosphinsäure-Derivate und deren Verwendung zur Behandlung von degenerativen Gelenkserkrankungen |
| DE19502209A1 (de) * | 1995-01-25 | 1996-08-01 | Hoechst Ag | Phosphonoessigsäure-Derivate und deren Verwendung zur Behandlung von degenerativen Gelenkserkrankungen |
| CH690264A5 (fr) * | 1995-06-30 | 2000-06-30 | Symphar Sa | Dérivés aminophosphonates substitués, leur procédé de préparation et leur utilisation pour la préparation de compositions pharmaceutiques. |
| GB9626536D0 (en) * | 1996-12-20 | 1997-02-05 | Symphar Sa | Novel compounds |
| GB9626616D0 (en) * | 1996-12-20 | 1997-02-05 | Symphar Sa | Novel compounds |
| GB9626615D0 (en) * | 1996-12-20 | 1997-02-05 | Symphar Sa | Novel compounds |
| JP3418322B2 (ja) | 1997-08-28 | 2003-06-23 | 日本電信電話株式会社 | 使用状態表示機能付きｉｃカードおよびｉｃカードシステム |
| DE19748659A1 (de) * | 1997-11-04 | 1999-05-06 | Hoechst Ag | Aminophosphoniumgruppen enthaltende vernetzte Copolymere für medizinische Verwendungen |
| DE69910045T2 (de) | 1998-09-09 | 2004-04-22 | Metabasis Therapeutics Inc., San Diego | Neue heteroaromatische fructose 1,6-bisphosphatase inhibitoren |
| EP1242066B1 (en) | 1999-10-27 | 2006-06-28 | Teva Pharmaceutical Industries Ltd. | Use of 1-aminoindan derivatives for treatment of mania in bipolar mood disorder |
| US7563774B2 (en) | 2000-06-29 | 2009-07-21 | Metabasis Therapeutics, Inc. | Combination of FBPase inhibitors and antidiabetic agents useful for the treatment of diabetes |
| US20030114421A1 (en) * | 2000-09-27 | 2003-06-19 | Phan Hieu Trung | Alpha-substituted beta-aminoethyl phosphonate derivatives |
| AU9479201A (en) | 2000-09-27 | 2002-04-08 | Ilex Oncology Res S A | Alpha-substituted beta-aminoethyl phosphonates |
| GB0025849D0 (en) | 2000-10-23 | 2000-12-06 | Smithkline Beecham Plc | Novel compounds |
| EP2520290B1 (en) * | 2003-12-23 | 2014-12-10 | Abraxis BioScience, LLC | Propofol analogs, process for their preparation, and methods of use |
| JP4824968B2 (ja) * | 2005-08-18 | 2011-11-30 | 株式会社クレハ | ホスホン酸誘導体及びその酸付加塩、並びにそれを用いた農園芸用病害防除剤 |
| JP2007318972A (ja) | 2006-05-29 | 2007-12-06 | Jtekt Corp | モータ及び電動パワーステアリング装置 |
| CN101003548B (zh) * | 2006-12-12 | 2010-09-08 | 中国林业科学研究院林产化学工业研究所 | 松香基二萜改性α-氨基磷酸酯、制备方法及抗肿瘤应用 |
| EP2854539A4 (en) * | 2012-05-14 | 2016-03-09 | Univ Kansas | PHOSPHONATE DERIVATIVES FOR THE TREATMENT OF MORBUS ALZHEIMER |
| CN104987350B (zh) * | 2015-01-29 | 2017-12-05 | 贵州大学 | 一类具有抗病毒活性的含苯并噻唑杂环的手性α‑氨基膦酸酯化合物及制备和应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1200679B (de) * | 1964-04-25 | 1965-09-09 | Agfa Ag | Lichtempfindliches Material mit eingelagerter Entwicklersubstanz |
| GB1298199A (en) * | 1969-02-13 | 1972-11-29 | Curwen & Newberry Ltd | Improvements in or relating to boilers or fluid heaters |
| US4144224A (en) * | 1976-11-26 | 1979-03-13 | Ciba-Geigy Corporation | Phosphonate stabilizers |
| CH675422A5 (ko) * | 1988-03-31 | 1990-09-28 | Symphar Sa |
-
1992
- 1992-03-05 CH CH704/92A patent/CH683996A5/fr not_active IP Right Cessation
-
1993
- 1993-02-25 SG SG1996001674A patent/SG43831A1/en unknown
- 1993-02-25 ES ES93102934T patent/ES2108772T3/es not_active Expired - Lifetime
- 1993-02-25 AT AT93102934T patent/ATE156829T1/de not_active IP Right Cessation
- 1993-02-25 EP EP93102934A patent/EP0559079B1/en not_active Expired - Lifetime
- 1993-02-25 DE DE69312984T patent/DE69312984T2/de not_active Expired - Fee Related
- 1993-02-25 DK DK93102934.2T patent/DK0559079T3/da not_active Application Discontinuation
- 1993-02-26 US US08/024,731 patent/US5424303A/en not_active Expired - Lifetime
- 1993-03-02 ZA ZA931473A patent/ZA931473B/xx unknown
- 1993-03-03 NZ NZ247056A patent/NZ247056A/en unknown
- 1993-03-03 NO NO930768A patent/NO303783B1/no unknown
- 1993-03-04 CA CA002091031A patent/CA2091031A1/en not_active Abandoned
- 1993-03-04 AU AU33947/93A patent/AU662957B2/en not_active Ceased
- 1993-03-04 FI FI930974A patent/FI930974A/fi unknown
- 1993-03-05 KR KR1019930003335A patent/KR930019685A/ko not_active IP Right Cessation
- 1993-03-05 JP JP5069078A patent/JPH0649083A/ja active Pending
-
1997
- 1997-11-05 GR GR970402906T patent/GR3025268T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US5424303A (en) | 1995-06-13 |
| AU662957B2 (en) | 1995-09-21 |
| CH683996A5 (fr) | 1994-06-30 |
| AU3394793A (en) | 1993-09-09 |
| ZA931473B (en) | 1993-09-23 |
| JPH0649083A (ja) | 1994-02-22 |
| EP0559079B1 (en) | 1997-08-13 |
| ES2108772T3 (es) | 1998-01-01 |
| DE69312984T2 (de) | 1998-03-12 |
| FI930974A (fi) | 1993-09-06 |
| FI930974A0 (fi) | 1993-03-04 |
| NO930768D0 (no) | 1993-03-03 |
| EP0559079A1 (en) | 1993-09-08 |
| DE69312984D1 (de) | 1997-09-18 |
| GR3025268T3 (en) | 1998-02-27 |
| NO303783B1 (no) | 1998-08-31 |
| CA2091031A1 (en) | 1993-09-06 |
| NO930768L (no) | 1993-09-06 |
| NZ247056A (en) | 1995-08-28 |
| SG43831A1 (en) | 1997-11-14 |
| ATE156829T1 (de) | 1997-08-15 |
| DK0559079T3 (da) | 1998-03-30 |
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