KR830010044A - 알릴아민 mao 억제제의 제조방법 - Google Patents
알릴아민 mao 억제제의 제조방법 Download PDFInfo
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- KR830010044A KR830010044A KR1019820002435A KR820002435A KR830010044A KR 830010044 A KR830010044 A KR 830010044A KR 1019820002435 A KR1019820002435 A KR 1019820002435A KR 820002435 A KR820002435 A KR 820002435A KR 830010044 A KR830010044 A KR 830010044A
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- phenyl
- hydrogen
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- fluorine
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- 238000000034 method Methods 0.000 title claims 16
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 title 2
- 239000002899 monoamine oxidase inhibitor Substances 0.000 title 1
- -1 succinimido, maleimido Chemical group 0.000 claims 44
- 239000001257 hydrogen Substances 0.000 claims 22
- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 18
- 229910052731 fluorine Inorganic materials 0.000 claims 17
- 239000011737 fluorine Substances 0.000 claims 17
- 150000002431 hydrogen Chemical class 0.000 claims 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 12
- 229910052794 bromium Inorganic materials 0.000 claims 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 11
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 8
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 7
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 7
- 125000001153 fluoro group Chemical group F* 0.000 claims 7
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 239000000460 chlorine Substances 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims 5
- 235000012054 meals Nutrition 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- 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 3
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims 2
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000005157 alkyl carboxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000005544 phthalimido group Chemical group 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/62—Preparation of compounds containing amino groups bound to a carbon skeleton by cleaving carbon-to-nitrogen, sulfur-to-nitrogen, or phosphorus-to-nitrogen bonds, e.g. hydrolysis of amides, N-dealkylation of amines or quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- 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
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
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- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
- C07C33/48—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts with unsaturation outside the aromatic rings
- C07C33/483—Monocyclic
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Abstract
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Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (22)
- 일반식(Ⅴ) 또는 (Ⅵ)의 화합물의 석신이미도, 말레이미도 또는 프탈이미도 그룹을 1급 아미노 그룹으로 전환시킴을 특징으로 하여 일반식(Ⅰ) 또는 (Ⅱ)의 화합물을 제조하는 방법상기식중R은 3,4-메틸렌디옥시페닐, 페닐, (C1-C8)알킬, (C1-C8)알콕시, (C1-C6)알킬, 카보닐옥시, 하이드륵시, 염소, 브롬, 요오드, 불소, 트리플루오로메틸, 니트로, (C1-C6)알킬카보닐, 벤조일, 혹은 페닐기등에 의해 단일, 이중, 혹은 삼중치환된 페닐, 1-혹은 2-나프틸, 1-,2- 혹은 3-인데닐, 1-,2-, 혹은 9-플루오레닐, 2-피리디닐, 1-,2-, 혹은 3-피페리디닐, 2-혹은 3-피를릴, 2-혹은 3-티에닐, 2-혹은 3-푸라닐, 2-혹은 3-인돌릴, 2-혹은 3-티아나프테닐, 혹은 2-혹은 3-벤조푸라닐이고,R1은 수소, (C1-C8)알킬, 벤질, 혹은 페네틸이며X와 Y는 각각 수소, 불소, 염소 혹은 브롬이고A는 다음과 같은 구조식을 가지는 2가 라디칼이며,-(여기서 R2는 수소, 메틸 혹은 에틸이고, m과 n은 각각 0에서 4까지의 정수이며 단 m+n은 4보다 클 수 없다), -(CH2)p-D-(CH2)q-(여기서 D는 산소 혹은 유황이며 P는 2에서 4까지의 정수이고, q는 0에서 2까지의 정수이며 단, p+q는 4보다 클 수 없다), 혹은 -(CH2)rCH=CH(CH2)s-(여기서 r는 1에서 3까지의 정수이고, S는 0에서 2까지의 정수이며 단, r+s는 3보다 클 수 없다),단, 일반식(Ⅰ)중 X 및 Y가 각기 수소일 경우에는 R이 페닐이 될 수 없고W는또는이다.
- 제1항에 있어서, W가이고 하이드라진과 반응시키거나 강무기산을 사용하여 가수분해적 분해법에 의해 처리하는 방법.
- 일반식(Ⅶ) 또는 (Ⅷ)의 알콜의 하이드록시 그룹을 1급 아미노 그룹으로 전환시킴을 특징으로 하여 일반식(Ⅰ) 또는 (Ⅱ)의 화합물을 제조하는 방법상기식중R은 3,4-메틸렌디옥시페닐, 페닐, (C1-C8)알킬, (C1-C8)알콕시, (C1-C6)알킬카보닐옥시, 하이드록시염소, 브롬, 요오드, 불소, 트리플루오로메틸, 니트로, (C1-C6)알킬카보닐, 벤조일, 혹은 페닐기등에 의해 단일, 이중, 혹은 삼중치환된 페닐, 1-혹은 2-나프틸, 1-,2-, 혹은 3-인데닐, 1-,2-, 혹은 9-플루오레닐, 2-피리디닐, 1-,2-, 혹은 3-피페리디닐, 2-혹은 3-피롤릴, 2-혹은 3-티에닐, 2-혹은 3-푸라닐, 2-혹은 3-인돌릴, 2-혹은 3-티아나프테닐, 혹은 2-혹은 3-벤조푸라닐이고R1은 수소, (C1-C8)알킬, 벤질, 혹은 페네틸이며X와 Y는 각각 수소, 불소, 염소 혹은 브롬이고A는 다음과 같은 구조식을 가지는 2가 라디칼이며,-(여기서 R2는 수소, 메틸 혹은 에틸이고, m과 n은 각각 0에서 4까지의 정수이며 단 m+n은 4보다 클 수 없다),-(CH2)p-D-(CH2)q-(여기서 D는 산소 혹은 유황이며 P는 2에서 4까지의 정수이고 q는 0에서 2까지의 정수이며 단, p+q는 4보다 클 수 없다), 혹은-(CH2)rCH=CH(CH2)s-(여기서 r은 1에서 3까지의 정수이고, S는 0에서 2까지의 정수이며 단 r+s는 3보다 클 수 없다),단, 일반식(Ⅰ) 중 X 및 Y가 각기 수소일 경우에는 R이 페닐이 될 수 없고, 단, Y가 불소, 염소 또는 브롬일 경우에는 X가 수소가 될 수 없다.
- 제2항에 있어서, 언급된 알콜을 일반식(Ⅸ) 또는 (Ⅹ)의 유도체로 전환시킨후 이 유도체의 석신이미도프탈이미도 또는 말레이미도 그룹, 헥사메틸렌테트르암모늄그룹 또는 (C1-C4)알킬 카복시마미노 그룹을 1급 아미노 그룹으로 전환시키는 방법.상기식중X,Y 및 R은 일반식(Ⅰ) 또는 (Ⅱ)에서 정의된 바와 같으나, Y가 불소, 염소 또는 브롬일 경우에는 X가 수소가 될 수 없으며, B는 석신이미도, 프탈이미도 또는 말레이미도 그룹, 헥사메틸렌테트르암모늄그룹 또는 (C1-C4)-알킬카복시 아미노 그룹이다.
- 제4항에 있어서, (a) B가 석신이미도, 프탈이미도 또는 말레이미도 그룹이고 하이드라진과 반응시키거나 강산을 사용하여 가수분해적으로 분해시킴을 특징으로 하여 언급된 아미노로 전환시키거나, (b) B가 헥사메틸렌테르라암모늄 그룹이고 강산과 함께 가열처리함을 특징으로 하여 언급된 그룹을 아미노로 전환시키거나, (C) B가 (C1-C4)알킬카복시 아미노 그룹이고 강무기산으로 가수분해시킴을 특징으로 하여 언급된 그룹을 아미노로 전환시키는 방법.
- 제1항 내지 5항중의 어느 하나에 있어서, 제조된 화합물이 일반식(Ⅰ)의 화합물인 방법.
- 제1항 내지 5항중의 어느 하나에 있어서, 제조된 화합물이 일반식(Ⅱ)의 화합물인 방법.
- 제7항에 있어서, A가 -CH2-인 방법.
- 제1항 내지 8항중의 어느 하나에 있어서, X가 불소이고 Y가 수소인 방법.
- 제1항 내지 9항중의 어느 하나에 있어서, R이 3,4-메틸렌디옥시페닐, 페닐, (C1-C8)알킬, (C1-C8)알콕시, (C1-C6)알킬카보닐옥시, 하이드록시, 염소, 브롬, 요오드, 불소, 트리플루오로메틸, 니트로, (C1-C6)-알킬카보닐, 벤조일 또는 페닐로 모노치환, 디치환 또는 트리치환된 페닐, 또는 1-나프틸 또는 2-나프틸인 방법.
- 제10항에 있어서, R이 페닐, (C1-C8)알콕시페닐, 디(C1-C8)알콕시페닐, (C1-C8)알킬페닐, 하이드록시페닐, 디하이록시페닐, 클로로페닐, 트리플루오로메틸페닐, 1-나프틸 또는 2-나프틸인 방법.
- 제11항에 있어서, R이 메톡시페닐, 디메톡시페닐, 에톡시페닐 또는 디에톡시페닐인 방법.
- 제12항에 있어서, X가 불소이고 Y가 수소이며 R1이 수소이고 R은 3,4-디메톡시페닐이며 제조된 생성물이(E)-2-(3′,4′-디메톡시페닐)-3-플루오로 알릴아민인 방법.
- 일반식(ⅩⅠ) 또는 (ⅩⅡ)의 화합물을 환원시킴을 특징으로 하여 일반식(Ⅲ) 또는 (Ⅳ)의 화합물을 제조하는 방법.상기식중R은 3,4-메틸렌디옥시페닐, 페닐, (C1-C8)알킬, (C1-C8)알콕시, (C1-C8)알킬카보닐옥시, 하이드록시염소, 브롬, 요오드, 불소, 트리플루오로메틸, 니트로, (C1-C6)알킬카보닐, 벤조일, 혹은 페닐기등에 의해 단일, 이중, 혹은 삼중치환된 페닐, 1-혹은 2-나프틸, 1-,2-, 혹은 3-인데닐, 1-,2-, 혹은 9-플루오레닐, 2-피리디닐, 1-,2-, 혹은 3-피페리디닐, 2-혹은 3-피롤릴, 2-혹은 3-티에닐, 2-혹은 3-푸라닐, 2-혹은 3-인돌릴, 2-혹은 3-티아나프테닐, 혹은 2-혹은 3-벤조푸라닐이고X와 Y는 각각 수소, 불소, 염소 혹은 브롬이고 A는 다음과 같은 구조식을 가지는 2가 라디칼이며,-(여기서 R는 수소, 메틸, 혹은 에틸이고, m과 n은 각각 0에서 4까지의 정수이며 단 m+n은 4보다 클 수 없다),-(CH2)p-D-(CH2)q-(여기서 D는 산소 혹은 유황이며 P는 2에서 4까지의 정수이고 q는 0에서 2까지의 정수이며 단, p+q는 4보다 클 수 없다), 혹은-(CH2)rCH=CH(CH2)s-(여기서 r은 1에서 3까지의 정수이고, S는 0에서 2까지의 정수이며 단 r+s는 3보다 클 수 없다),Rd는 수소 또는 (C1-C4)알킬이다.
- 제14항에 있어서, 환원반응을 디이소부틸 알루미늄 하이드리드를 사용하여 시행하는 방법.
- 제15항에 있어서, X가 불소이고 Y가 수소인 방법.
- 제14항 또는 제16항에 있어서, R이 3,4-메틸렌디옥시페닐, 페닐, (C1-C8)알킬, (C1-C8)알콕시, (C1-C8)알킬카보닐옥시, 하이드록시, 염소, 브롬, 요오드, 불소, 트리플루오로메틸, 니트로, (C1-C6)-알킬카보닐, 벤조일 또는 페닐로 모노치환된, 디치환된 또는 트리치환된 페닐, 또는 1-또는 2-나프타린 방법.
- 제17항에 있어서, R이 페닐, (C1-C8)알콕시페닐, 디(C1-C8)알콕시페닐, (C1-C8)알킬페닐, 하이드록시페닐, 디하이드록시페닐, 클로로페닐, 트리플루오로메틸페닐, 1-나프틸 또는 2-나프틸인 방법.
- 제18항에 있어서, R이 메톡시페닐, 디메톡시페닐, 에톡시페닐 또는 디에톡시 페닐인 방법.
- 제19항에 있어서, X가 불소이고, Y가 수소이며 R이 3,4-메톡시페닐이고 제조된 화합물이 (E)-2-(3′,4′-디메톡시페닐)-3-플루오로알릴 알콜인 방법.
- 일반식(ⅩⅢ) 또는 (ⅩⅣ)의 화합물을 알킬화시킴을 특징으로 하여 일반식(Ⅰ′) 또는 (Ⅱ′)의 화합물을 제조하는 방법상기식중R은 3,4-메틸디옥시페닐, 페닐, (C1-C8)알킬, (C1-C8)알콕시, (C1-C8)알킬카보닐옥시, 하이드록시, 염소, 브롬, 요오드, 불소, 트리플루오로메틸, 니트로, (C1-C6)알킬카보닐, 벤조일, 혹은 페닐기등에 의해 단일, 이중, 혹은 삼중 치환된 페닐, 1-혹은 2-나프틸, 1-,2-, 혹은 3-인데닐, 1-,2-, 혹은 9-플루오레닐, 2-피리디닐, 1-,2-, 혹은 3-피페리디닐, 2-혹은 3-피롤릴, 2-혹은 3-티에닐, 2-혹은 3-푸라닐, 2-혹은 3-인돌릴, 2-혹은 3-티아나프테닐, 혹은 2-혹은 3-벤조푸라닐이고R은 (C1-C8)알킬, 벤질, 혹은 페네틸이며X와 Y는 각각 수소, 불소, 염소 혹은 브롬이고A는 다음과 같은 구조식을 가지는 2가 라디칼이며,-(여기서 R는 수소, 메틸, 혹은 에틸이고, m과 n은 각각 0에서 4까지의 정수이며 단 m+n은 4보다 클 수 없다),-(CH2)p-D-(CH2)q-(여기서 D는 산소 혹은 유황이며 P는 2에서 4까지의 정수이고 q는 0에서 2까지의 정수이며 단, p+q는 4보다 클 수 없다), 혹은-(CH2)rCH=CH(CH2)s-(여기서 r은 1에서 3까지의 정수이고, S는 0에서 2까지의 정수이며 단 r+s는 3보다 클 수 없다),단, 일반식(Ⅰ)중 X및 Y가 각기 수소일 경우에는 R이 페닐이될 수 없다.
- 제21항에 있어서, X가 불소이고 Y가 수소이며 R이 4-메톡시페닐 또는 3,4- 디메톡시페닐이고 R1이 메틸 또는 에틸인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/268,555 US4454158A (en) | 1981-06-01 | 1981-06-01 | Allyl amine MAO inhibitors |
| US268555 | 1981-06-01 | ||
| US268.555 | 1982-06-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830010044A true KR830010044A (ko) | 1983-12-24 |
| KR890002756B1 KR890002756B1 (ko) | 1989-07-27 |
Family
ID=23023513
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8202435A KR890002756B1 (ko) | 1981-06-01 | 1982-05-31 | 알릴아민 mao 억제제의 제조 방법 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4454158A (ko) |
| EP (1) | EP0067105B1 (ko) |
| JP (1) | JPS5823649A (ko) |
| KR (1) | KR890002756B1 (ko) |
| AT (1) | ATE29875T1 (ko) |
| AU (2) | AU550607B2 (ko) |
| CA (2) | CA1187500A (ko) |
| DE (1) | DE3277371D1 (ko) |
| DK (1) | DK244282A (ko) |
| ES (4) | ES8402810A1 (ko) |
| GB (2) | GB2100255B (ko) |
| GR (1) | GR78033B (ko) |
| IE (1) | IE53456B1 (ko) |
| IL (2) | IL65808A (ko) |
| MX (1) | MX9202950A (ko) |
| NO (1) | NO152837C (ko) |
| NZ (1) | NZ200644A (ko) |
| ZA (1) | ZA823633B (ko) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4699928A (en) * | 1984-07-13 | 1987-10-13 | Merrell Dow Pharmaceuticals Inc. | Fluoroallylamine derivatives |
| US4703058A (en) * | 1984-12-31 | 1987-10-27 | Merrell Dow Pharmaceuticals Inc. | β-methylene furanethanamines and use as anti-hypertensive agents |
| NZ214697A (en) * | 1984-12-31 | 1988-10-28 | Merrell Dow Pharma | B-methylene-2- and 3-furanethanamine and pharmaceutical compositions |
| NZ214698A (en) * | 1984-12-31 | 1988-08-30 | Merrell Dow Pharma | Thiophene derivatives and pharmaceutical compositions containing such |
| DE3683604D1 (de) * | 1985-12-05 | 1992-03-05 | Merrell Dow Pharma | Nichtaromatische fluoralkylamin-mao-inhibitoren. |
| US4650907A (en) * | 1985-12-05 | 1987-03-17 | Merrell Dow Pharmaceuticals Inc. | Nonaromatic fluoroallylamine MAO inhibitors |
| US4822812A (en) * | 1987-05-21 | 1989-04-18 | Merrell Dow Pharmaceuticals Inc. | β-(Fluoromethylene)-5-hydroxytryptophan and derivatives and their use as prodrugs for MAO inhibition |
| NZ224982A (en) * | 1987-06-16 | 1990-08-28 | Merrell Dow Pharma | E-2-(p-fluorophenethyl)-3-fluoroallylamine and its pharmaceutical compositions |
| US5252608A (en) * | 1988-02-25 | 1993-10-12 | Merrell Dow Pharmaceuticals Inc. | Inhibitors of lysyl oxidase |
| US5182297A (en) * | 1988-02-25 | 1993-01-26 | Merrell Dow Pharmaceuticals Inc. | Inhibitors of lysyl oxidase |
| US5059714A (en) * | 1988-02-25 | 1991-10-22 | Merrell Dow Pharmaceuticals Inc. | Inhibitors of lysyl oxidase |
| US4943593A (en) * | 1988-02-25 | 1990-07-24 | Merrell Dow Pharmaceuticals Inc. | Inhibitors of lysyl oxidase |
| CA1338647C (en) * | 1988-02-25 | 1996-10-15 | Michael G. Palfreyman | Inhibitors of lysyl oxidase |
| US4965288A (en) * | 1988-02-25 | 1990-10-23 | Merrell Dow Pharmaceuticals Inc. | Inhibitors of lysyl oxidase |
| US5120764A (en) * | 1988-11-01 | 1992-06-09 | Merrell Dow Pharmaceuticals Inc. | Inhibitors of lysyl oxidase |
| US4981868A (en) * | 1989-07-25 | 1991-01-01 | Merrell Dow Pharmaceutical | Pharmaceutically active 3-heteroaryl-2-fluoro-1-olefins |
| NZ302723A (en) * | 1995-03-02 | 1998-04-27 | Scherer Ltd R P | Composition comprising monoamine oxidase b inhibitor and a carrier formulated for pre-gastric absorption of the monoamine oxidase b inhibitor |
| WO2007120528A2 (en) * | 2006-03-31 | 2007-10-25 | La Jolla Pharmaceutical Company | Inhibitors of semicarbazide-sensitive amine oxidase (ssao) and vap-1 mediated adhesion useful for treatment and prevention of diseases |
| EP2046794A1 (de) * | 2006-07-13 | 2009-04-15 | Basf Se | Fungizide azolopyrimidine, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen sowie sie enthaltende mittel |
| WO2009055002A1 (en) * | 2007-10-24 | 2009-04-30 | La Jolla Pharmaceutical Company | Combined inhibitors of cyclooxygenase and semicarbazide-sensitive amine oxidase (ssao) (vascular adhesion protein, vap-1) |
| EP2222160B1 (en) | 2007-11-21 | 2015-03-18 | Pharmaxis Ltd. | Haloallylamine inhibitors of ssao/vap-1 and uses therefor |
| PL2844637T3 (pl) | 2012-05-02 | 2018-09-28 | Boehringer Ingelheim International Gmbh | Podstawione 3-haloalliloaminowe inhibitory ssao i ich zastosowania |
| WO2015087094A1 (en) * | 2013-12-10 | 2015-06-18 | Semmelweis Egyetem | New arylalkenylpropargylamine derivatives exhibiting neuroprotective action for the treatment of neurodegenerative diseases |
| TW202019877A (zh) | 2018-08-03 | 2020-06-01 | 澳大利亞商法瑪西斯有限公司 | 離胺醯氧化酶之鹵化烯丙胺碸衍生物抑制劑及其用途 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2343038A1 (de) * | 1973-08-25 | 1975-03-06 | Hoechst Ag | 2,3-diaryl-3-halogenallylamine und verfahren zu ihrer herstellung |
| SE7809127L (sv) * | 1978-08-30 | 1980-03-01 | Claesson Alf | Allenaminer |
-
1981
- 1981-06-01 US US06/268,555 patent/US4454158A/en not_active Expired - Lifetime
-
1982
- 1982-05-17 NZ NZ200644A patent/NZ200644A/en unknown
- 1982-05-17 IL IL65808A patent/IL65808A/xx not_active IP Right Cessation
- 1982-05-21 GB GB8214854A patent/GB2100255B/en not_active Expired
- 1982-05-25 ZA ZA823633A patent/ZA823633B/xx unknown
- 1982-05-25 IE IE1246/82A patent/IE53456B1/en not_active IP Right Cessation
- 1982-05-27 AU AU84238/82A patent/AU550607B2/en not_active Ceased
- 1982-05-27 EP EP82400991A patent/EP0067105B1/en not_active Expired
- 1982-05-27 AT AT82400991T patent/ATE29875T1/de active
- 1982-05-27 DE DE8282400991T patent/DE3277371D1/de not_active Expired
- 1982-05-28 NO NO821799A patent/NO152837C/no not_active IP Right Cessation
- 1982-05-28 CA CA000403943A patent/CA1187500A/en not_active Expired
- 1982-05-28 DK DK244282A patent/DK244282A/da not_active Application Discontinuation
- 1982-05-31 KR KR8202435A patent/KR890002756B1/ko active
- 1982-05-31 GR GR68306A patent/GR78033B/el unknown
- 1982-05-31 ES ES512699A patent/ES8402810A1/es not_active Expired
- 1982-06-01 JP JP57092250A patent/JPS5823649A/ja active Granted
-
1983
- 1983-07-05 ES ES523874A patent/ES523874A0/es active Granted
- 1983-07-05 ES ES523873A patent/ES523873A0/es active Granted
- 1983-07-05 ES ES523875A patent/ES523875A0/es active Granted
-
1984
- 1984-11-15 GB GB08428858A patent/GB2152039B/en not_active Expired
-
1985
- 1985-03-13 CA CA000476463A patent/CA1204759A/en not_active Expired
- 1985-07-17 IL IL75829A patent/IL75829A0/xx unknown
-
1986
- 1986-01-02 AU AU51805/86A patent/AU576281B2/en not_active Ceased
-
1992
- 1992-06-17 MX MX9202950A patent/MX9202950A/es unknown
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