KR920019721A - 광학 활성 2차 아민 화합물, 이의 제조방법 및 이를 이용한 광학 활성 카르복실산의 제조방법 - Google Patents
광학 활성 2차 아민 화합물, 이의 제조방법 및 이를 이용한 광학 활성 카르복실산의 제조방법 Download PDFInfo
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- KR920019721A KR920019721A KR1019920005857A KR920005857A KR920019721A KR 920019721 A KR920019721 A KR 920019721A KR 1019920005857 A KR1019920005857 A KR 1019920005857A KR 920005857 A KR920005857 A KR 920005857A KR 920019721 A KR920019721 A KR 920019721A
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- South Korea
- Prior art keywords
- hydroxy
- ethylamine
- methoxybenzyl
- hydroxybenzyl
- compound
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- -1 secondary amine compound Chemical class 0.000 title claims 71
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims 8
- 238000002360 preparation method Methods 0.000 title 2
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 11
- 238000000034 method Methods 0.000 claims 11
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 10
- 239000002253 acid Substances 0.000 claims 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 7
- 125000001624 naphthyl group Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 150000002466 imines Chemical class 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- XDVIWNKKFZZOBZ-UHFFFAOYSA-N 2-[(1-cyclohexylethylamino)methyl]-6-methoxyphenol Chemical compound COC1=CC=CC(CNC(C)C2CCCCC2)=C1O XDVIWNKKFZZOBZ-UHFFFAOYSA-N 0.000 claims 3
- YBGKDEDFGSTHKT-UHFFFAOYSA-N 2-[[1-(4-bromophenyl)ethylamino]methyl]-6-methoxyphenol Chemical compound COC1=CC=CC(CNC(C)C=2C=CC(Br)=CC=2)=C1O YBGKDEDFGSTHKT-UHFFFAOYSA-N 0.000 claims 3
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 3
- BMBGPGQJCYSEHF-UHFFFAOYSA-N 2-methoxy-6-[(1-phenylethylamino)methyl]phenol Chemical compound COC1=CC=CC(CNC(C)C=2C=CC=CC=2)=C1O BMBGPGQJCYSEHF-UHFFFAOYSA-N 0.000 claims 3
- JGHSCASIJSJKCV-UHFFFAOYSA-N 2-methoxy-6-[[1-(4-methylphenyl)ethylamino]methyl]phenol Chemical compound COC1=CC=CC(CNC(C)C=2C=CC(C)=CC=2)=C1O JGHSCASIJSJKCV-UHFFFAOYSA-N 0.000 claims 3
- VDCAUGMKBUHYIY-UHFFFAOYSA-N 2-methoxy-6-[[1-(4-propan-2-ylphenyl)ethylamino]methyl]phenol Chemical compound COC1=CC=CC(CNC(C)C=2C=CC(=CC=2)C(C)C)=C1O VDCAUGMKBUHYIY-UHFFFAOYSA-N 0.000 claims 3
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 3
- NBVIBKHMVOGMDC-UHFFFAOYSA-N 4-[(1-phenylethylamino)methyl]phenol Chemical compound C=1C=CC=CC=1C(C)NCC1=CC=C(O)C=C1 NBVIBKHMVOGMDC-UHFFFAOYSA-N 0.000 claims 3
- RMYKMCGWCMZPCS-UHFFFAOYSA-N 4-[[1-(4-bromophenyl)ethylamino]methyl]phenol Chemical compound C=1C=C(Br)C=CC=1C(C)NCC1=CC=C(O)C=C1 RMYKMCGWCMZPCS-UHFFFAOYSA-N 0.000 claims 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 238000006722 reduction reaction Methods 0.000 claims 3
- FLUCHNPWMOHOHM-UHFFFAOYSA-N 2-methoxy-6-[[1-(4-methoxyphenyl)ethylamino]methyl]phenol Chemical compound C1=CC(OC)=CC=C1C(C)NCC1=CC=CC(OC)=C1O FLUCHNPWMOHOHM-UHFFFAOYSA-N 0.000 claims 2
- AVJSUCZVDIYBJU-UHFFFAOYSA-N 2-methoxy-6-[[1-(4-nitrophenyl)ethylamino]methyl]phenol Chemical compound COC1=CC=CC(CNC(C)C=2C=CC(=CC=2)[N+]([O-])=O)=C1O AVJSUCZVDIYBJU-UHFFFAOYSA-N 0.000 claims 2
- BMNWONCEUMEPQL-UHFFFAOYSA-N 4-[(1-cyclohexylethylamino)methyl]phenol Chemical compound C1CCCCC1C(C)NCC1=CC=C(O)C=C1 BMNWONCEUMEPQL-UHFFFAOYSA-N 0.000 claims 2
- AVDKURWORRBGIU-UHFFFAOYSA-N 4-[(1-naphthalen-1-ylethylamino)methyl]phenol Chemical compound C=1C=CC2=CC=CC=C2C=1C(C)NCC1=CC=C(O)C=C1 AVDKURWORRBGIU-UHFFFAOYSA-N 0.000 claims 2
- DLLOLOOEKAPONJ-UHFFFAOYSA-N 4-[[1-(4-methoxyphenyl)ethylamino]methyl]phenol Chemical compound C1=CC(OC)=CC=C1C(C)NCC1=CC=C(O)C=C1 DLLOLOOEKAPONJ-UHFFFAOYSA-N 0.000 claims 2
- FSHIXDVAUYEROR-UHFFFAOYSA-N 4-[[1-(4-methylphenyl)ethylamino]methyl]phenol Chemical compound C=1C=C(C)C=CC=1C(C)NCC1=CC=C(O)C=C1 FSHIXDVAUYEROR-UHFFFAOYSA-N 0.000 claims 2
- WVBLGEKHAAWFNO-UHFFFAOYSA-N 4-[[1-(4-propan-2-ylphenyl)ethylamino]methyl]phenol Chemical compound C1=CC(C(C)C)=CC=C1C(C)NCC1=CC=C(O)C=C1 WVBLGEKHAAWFNO-UHFFFAOYSA-N 0.000 claims 2
- VMVDSBVUFHGDBR-UHFFFAOYSA-N 4-[[[2-(4-methylphenyl)-1-phenylethyl]amino]methyl]phenol Chemical compound C1=CC(C)=CC=C1CC(C=1C=CC=CC=1)NCC1=CC=C(O)C=C1 VMVDSBVUFHGDBR-UHFFFAOYSA-N 0.000 claims 2
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims 2
- JJVNINGBHGBWJH-UHFFFAOYSA-N ortho-vanillin Chemical compound COC1=CC=CC(C=O)=C1O JJVNINGBHGBWJH-UHFFFAOYSA-N 0.000 claims 2
- SOZMSEPDYJGBEK-UHFFFAOYSA-N 1-(4-bromophenyl)ethanamine Chemical compound CC(N)C1=CC=C(Br)C=C1 SOZMSEPDYJGBEK-UHFFFAOYSA-N 0.000 claims 1
- JTDGKQNNPKXKII-UHFFFAOYSA-N 1-(4-methoxyphenyl)ethanamine Chemical compound COC1=CC=C(C(C)N)C=C1 JTDGKQNNPKXKII-UHFFFAOYSA-N 0.000 claims 1
- UZDDXUMOXKDXNE-UHFFFAOYSA-N 1-(4-methylphenyl)ethanamine Chemical compound CC(N)C1=CC=C(C)C=C1 UZDDXUMOXKDXNE-UHFFFAOYSA-N 0.000 claims 1
- RAEVOBPXEHVUFY-UHFFFAOYSA-N 1-(4-nitrophenyl)ethanamine Chemical compound CC(N)C1=CC=C([N+]([O-])=O)C=C1 RAEVOBPXEHVUFY-UHFFFAOYSA-N 0.000 claims 1
- UHAQMLODFYUKOM-UHFFFAOYSA-N 1-(4-propan-2-ylphenyl)ethanamine Chemical compound CC(C)C1=CC=C(C(C)N)C=C1 UHAQMLODFYUKOM-UHFFFAOYSA-N 0.000 claims 1
- XBWOPGDJMAJJDG-UHFFFAOYSA-N 1-cyclohexylethanamine Chemical compound CC(N)C1CCCCC1 XBWOPGDJMAJJDG-UHFFFAOYSA-N 0.000 claims 1
- RTCUCQWIICFPOD-UHFFFAOYSA-N 1-naphthalen-1-ylethanamine Chemical compound C1=CC=C2C(C(N)C)=CC=CC2=C1 RTCUCQWIICFPOD-UHFFFAOYSA-N 0.000 claims 1
- KHSYYLCXQKCYQX-UHFFFAOYSA-N 1-naphthalen-2-ylethanamine Chemical compound C1=CC=CC2=CC(C(N)C)=CC=C21 KHSYYLCXQKCYQX-UHFFFAOYSA-N 0.000 claims 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 claims 1
- AQFLVLHRZFLDDV-UHFFFAOYSA-N 1-phenylpropan-1-amine Chemical compound CCC(N)C1=CC=CC=C1 AQFLVLHRZFLDDV-UHFFFAOYSA-N 0.000 claims 1
- VTJMSIIXXKNIDJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutyric acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(Cl)C=C1 VTJMSIIXXKNIDJ-UHFFFAOYSA-N 0.000 claims 1
- ZICDZTXDTPZBKH-UHFFFAOYSA-N 2-(4-methylphenyl)-1-phenylethanamine Chemical compound C1=CC(C)=CC=C1CC(N)C1=CC=CC=C1 ZICDZTXDTPZBKH-UHFFFAOYSA-N 0.000 claims 1
- JNJCEALGCZSIGB-UHFFFAOYSA-N 2-hydroxy-4-phenylbutanoic acid Chemical compound OC(=O)C(O)CCC1=CC=CC=C1 JNJCEALGCZSIGB-UHFFFAOYSA-N 0.000 claims 1
- ZNSUBYPSVCDYPB-UHFFFAOYSA-N 2-methoxy-6-[(1-naphthalen-1-ylethylamino)methyl]phenol Chemical compound COC1=CC=CC(CNC(C)C=2C3=CC=CC=C3C=CC=2)=C1O ZNSUBYPSVCDYPB-UHFFFAOYSA-N 0.000 claims 1
- UVXXBSCXKKIBCH-UHFFFAOYSA-N 2-methyl-1-phenylpropan-1-amine Chemical compound CC(C)C(N)C1=CC=CC=C1 UVXXBSCXKKIBCH-UHFFFAOYSA-N 0.000 claims 1
- HECWRQKULWTFRW-UHFFFAOYSA-N 4-[[1-(4-nitrophenyl)ethylamino]methyl]phenol Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(C)NCC1=CC=C(O)C=C1 HECWRQKULWTFRW-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000007868 Raney catalyst Substances 0.000 claims 1
- 229910000564 Raney nickel Inorganic materials 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 claims 1
- 238000010531 catalytic reduction reaction Methods 0.000 claims 1
- 125000006289 hydroxybenzyl group Chemical group 0.000 claims 1
- 239000012280 lithium aluminium hydride Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 1
- UYLUJGRCKKSWHS-UHFFFAOYSA-N prop-1-en-1-one Chemical compound CC=C=O UYLUJGRCKKSWHS-UHFFFAOYSA-N 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/16—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic the nitrogen atom of the amino group being further bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
- C07C215/50—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
내용 없음
Description
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Claims (27)
- 하기 일반식(Ⅰ)의 광학 활성 2차 아민 화합물 또는 그의 염:(상기식에서, R1은 나프틸 또는 시클로헥실기, 또는 할로겐, 니트로, 저급 알킬 또는 저급 알콕시로 치환될 수 있는 페닐기를 나타내고, R2는 저급 알킬기 또는 저급 알킬로 치환될 수 있는 벤질기를 나타내며, R3은 R2가 저급 알킬일 때, p-히드록시페닐 또는 2-히드록시-3-저급 알콕시페닐기를 나타내거나, R2가 저급 알킬로 치환될 수 있는 벤질일 때 p-히드록시페닐기를 나타내고, C*는 부재 탄소원자를 나타낸다).
- 제1항에 있어서, R1이 나프틸, 시클로헥실, 페닐, o-, m- 또는 p-클로로페닐, o-, m- 또는 p-브로모페닐, o-, m- 또는 p-니트로페닐, o-, m- 또는 p-톨릴, o-, m- 또는 p-에틸페닐, o-, m- 또는 p-프로필페닐, o-, m- 또는 p-메톡시페닐, o-, m- 또는 p-에톡시페닐 또는 o-, m- 또는 p-프로폭시페닐인 광학 활성 2차 아민 화합물 또는 그의 염.
- 제1항에 있어서, R2가 메틸, 에틸, 프로필, 부틸, 펜틸, 벤질, o-, m- 또는 p-톨릴메틸, o-, m- 또는 p-에틸페닐메틸, o-, m- 또는 p-프로필페닐메틸, o-, m- 또는 p-부틸페닐메틸 또는 o-, m- 또는 p-펜틸페닐메틸인 광학 활성 2차 아민 화합물 또는 그의 염.
- 제1항에 있어서, R3이 p-히드록시페닐, 2-히드록시-3-메톡시페닐, 2-히드록시-3-에톡시페닐, 2-히드록시-3-프로폭시페닐, 2-히드록시-3-부톡시페닐 또는 2-히드록시-3-펜톡시페닐인 광학 활성 2차 아민 화합물 또는 그의 염.
- 제1항에 있어서, 화합물이 N-(p-히드록시벤질)-1-페닐에틸아민, N-(p-히드록시벤질)-1-(p-톨릴)에틸아민, N-(p-히드록시벤질)-1-(p-이소프로필페닐)에틸아민,N-(p-히드록시벤질)-1-(p-니트로페닐)에틸아민,N-(p-히드록시벤질)-1-(p-브로모페닐)에틸아민, N-(p-히드록시벤질)-1-(p-나프틸)에틸아민, N-(p-히드록시벤질)-1-시클로헥실에틸아민, N-(p-히드록시벤질)-1-(p-메톡시페닐)에틸아민, N-(2-히드록시-3-메톡시벤질)-1-페닐에틸아민, N-(2-히드록시-3-메톡시벤질)-1-(p-톨릴)에틸아민, N-(2-히드록시-3-메톡시벤질)-1-(p-이소프로필페닐)에틸아민, N-(2-히드록시-3-메톡시벤질)-1-(p-니트로페닐)에틸아민,N-(2-히드록시-3-메톡시벤질)-1-(p-브로모페닐)에틸아민,N-(2-히드록시-3-메톡시벤질)-1-(1-나프틸)에틸아민, N-(2-히드록시-3-메톡시벤질)-1-시클로헥실에틸아민, N-(2-히드록시-3-메톡시벤질)-1-(p-메톡시페닐)에틸아민 및 N-p-히드록시벤질-α-페닐-β-p-톨릴에틸아민을 포함하는 광학 활성 2차 아민 화합물 또는 그의 염.
- 하기 일반식(Ⅱ)의 광학 활성 아민을 하기 일반식(Ⅲ)의 히드록시벤즈알데히드와 반응시켜 하기 일반식(Ⅳ)의 이민 화합물을 형성한 후, 수득한 이민 화합물을 환원 반응시켜 하기 일반식(Ⅰ)의 광학 활성 2차 아민 화합물 또는 그의 염을 제조하는 방법.(상기식에서, R1은 나프틸 또는 시클로헥실기, 또는 할로겐, 니트로, 저급 알킬 또는 저급 알콕시로 치환될 수 있는 페닐기를 나타내고, R2는 저급 알킬기 또는 저급 알킬로 치환될 수 있는 벤질기를 나타내며, R3은 R2가 저급 알킬일 때, p-히드록시페닐 또는 2-히드록시-3-저급 알콕시페닐기를 나타내거나, R2가 저급 알킬로 치환될 수 있는 벤질일 때 p-히드록시페닐기를 나타내고, C*는 부제 탄소원자를 나타낸다).
- 제6항에 있어서, 광학 활성 화합물(Ⅱ)가 1-페닐에틸아민, 1-(1-나프틸)에틸아민, 1-시클로헥실에틸아민, 1-(p-톨릴)에틸아민, 1-(p-이소프로필페닐)에틸아민, 1-(p-니트로페닐)에틸아민, 1-(p-브로모페닐)에틸아민, α-에틸벤질아민, α-이소프로필벤질아민, 1-(β-나프틸)에틸아민 또는 α-페닐-β-p-톨릴에틸아민인 방법.
- 제6항에 있어서, 히드록시벤즈알데히드(Ⅲ)이 p-히드록시벤즈 알데히드 또는 2-히드록시-3-메톡시벤즈알데히드인 방법.
- 제6항에 있어서, 수소화 알루미늄 리튬, 수소화붕소 나트륨, 디보란, 보란-THF, 보란-술피드 착화합물 또는 보란-아민 착화합물 존재하에서 환원반응을 수행하는 방법.
- 제6항에 있어서, 환원 반응이 라니 니켈, 팔라듐, 카아본, 플라티늄 디옥사이드 또는 플라티늄 블랙을 사용한 촉매 환원 반응인 방법.
- 제6항에 있어서, 광학 활성 2차 아민 화합물이 N-(p-히드록시벤질)-1-페닐에틸아민, N-(p-히드록시벤질)-1-(p-톨릴)에틸아민, N-(p-히드록시벤질)-1-(p-이소프로필페닐)에틸아민, N-(p-히드록시벤질)-1-(p-브로모페닐)에틸아민, N-(p-히드록시벤질)-1-(1-나프틸)에틸아민, N-(p-히드록시벤질)-1-시클로헥실에틸아민, N-(p-히드록시벤질)-1-(p-메톡시페닐)에틸아민, N-(2-히드록시-3-메톡시벤질)-1-페닐에틸아민, N-(2-히드록시-3-메톡시벤질)-1-(p-톨릴)에틸아민, N-(2-히드록시-3-메톡시벤질)-1-(p-이소프로필페닐)에틸아민, N-(2-히드록시-3-메톡시벤질)-1-(p-니트로페닐)에틸아민, N-(2-히드록시-3-메톡시벤질)-1-(p-니트 닐)에틸아민, N-(2-히드록시-3-메톡시벤질)-1-(p-브로모페닐)에틸아민, N-(2-히드록시-3-메톡시벤질)-1-(p-나프틸)에틸아민, N-(2-히드록시-3-메톡시벤질)-1-시클로헥실에틸아민, N-(2-히드록시-3-메톡시벤질)-1-(p-메톡시페닐)에틸아민 또는 N-p-히드록시벤질-α-β-p-톨릴에틸아민인 방법.
- 하기 일반식(Ⅳ)의 이민 화합물:(상기식에서, R1은 나프틸 또는 시클로헥실기, 또는 할로겐, 니트로, 저급 알킬 또는 저급 알콕시로 치환될 수 있는 페닐기를 나타내고, R2는 저급 알킬기 또는 저급 알킬로 치환될 수 있는 벤질기를 나타내며, R3은 R2가 저급 알킬일 때, p-히드록시페닐 또는 2-히드록시-3-저급 알콕시페닐기를 나타내거나, R2가 저급 알킬로 치환될 수 있는 벤질일 때 p-히드록시페닐기를 나타내고, C*는 부제 탄소원자를 나타낸다).
- 제12항에 있어서, R1이 나프틸, 시클로헥실, 페닐, o-, m- 또는 p-클로로페닐, o-, m- 또는 p-브로모페닐, o-, m- 또는 p-니트로페닐, o-, m- 또는 p-톨릴, o-, m- 또는 p-에틸페닐, o-, m- 또는 p-프로필페닐, o-, m- 또는 p-메톡시페닐, o-, m- 또는 p-에톡시페닐 또는 o-, m- 또는 p-프로폭시페닐인 이민 화합물.
- 제12항에 있어서, R2가 메틸, 에틸, 프로필, 부틸, 펜틸, 벤질, o-, m- 또는 p-톨릴메틸, o-, m- 또는 p-에틸페닐메틸, o-, m- 또는 p-프로필페닐메틸, o-, m- 또는 p-부틸페닐메틸 또는 o-, m- 또는 p-펜틸페닐메틸인 이민 화합물.
- 제12항에 있어서, R3이 p-히드록시페닐, 2-히드록시-3-메톡시페닐, 2-히드록시-3-에톡시페닐, 2-히드록시-3-프로폭시페닐, 2-히드록시-3-부톡시페닐 또는 2-히드록시-3-펜톡시펜닐인 이민 화합물.
- 하기 일반식(Ⅰ)의 광학 활성 2차 아민 화합물을 (±)-크리산템산, (±)-이부프로펜, (±)-나프록센, (±)-플루르비프로펜, (±)-케토프로펜, (±)-2-(4-클로로페닐)이소발레르산, (±)-만델산, (±)-2-히드록시-4-페닐부탄산 및 (±)-페르메쓰르산으로 구성된 군으로부터 선택한 라세믹 카르복실산과 반응시키고 생성된 아민 염을 광학 분해 조작함을 특징으로 하는 광학 활성 카르복실산의 제조방법:(상기식에서, R1은 나프틸 또는 시클로헥실기, 또는 할로겐, 니트로, 저급 알킬 또는 저급 알콕시로 치환될 수 있는 페닐기를 나타내고, R2는 저급 알킬기 또는 저급 알킬로 치환될 수 있는 벤질기를 나타내며, R3은 R2가 저급 알킬일 때, p-히드록시페닐 또는 2-히드록시-3-저급 알콕시페닐기를 나타내거나, R2가 저급 알킬로 치환될 수 있는 벤질일 때 p-히드록시페닐기를 나타내고, C*는 부제 탄소원자를 나타낸다).
- 제16항에 있어서, 라세믹 카르복실산이 (±)-크리산템산인 방법.
- 제17항에 있어서, (±)-크리산템산이 (±)-트란스-크리산템산 또는 (±)-시스/트란스-혼합 크리산템산인 방법.
- 제16항에 있어서, 라세믹 카르복실산이 (±)-페르메쓰르산인 방법.
- 제19항에 있어서, (±)-페르메쓰르산이 (±)-트란스-페르메쓰르산 또는 (±)-시스-페르메쓰르산인 방법.
- 제16항에 있어서, 라세믹 카르복실산이 (±)-케토프로펜인 방법.
- 제16항에 있어서, 라세믹 카르복실산이 (±)-만델산인 방법.
- 제16항에 있어서, 라세믹 카르복실산이 (±)-2-(4-클로로페닐)-이소발레르산인 방법.
- 제16항에 있어서, R1이 나프틸, 시클로헥실, 페닐, o-, m- 또는 p-클로로페닐, o-, m- 또는 p-브로모페닐, o-, m- 또는 p-니트로페닐, o-, m- 또는 p-톨릴, o-, m- 또는 p-에틸페닐, o-, m- 또는 p-프로필페닐, o-, m- 또는 p-메톡시페닐, o-, m- 또는 p-에톡시페닐 또는 o-, m- 또는 p-프로폭시페닐인 방법.
- 제16항에 있어서, R2가 메틸, 에틸, 프로필, 부틸, 펜틸, 벤질, o-, m- 또는 p-톨릴메틸, o-, m- 또는 p-에틸페닐메틸, o-, m- 또는 p-프로필페닐메틸, o-, m- 또는 p-부틸페닐메틸 또는 o-, m- 또는 p-펜틸페닐메틸인 방법.
- 제16항에 있어서, R3이 p-히드록시페닐, 2-히드록시-3-메톡시페닐, 2-히드록시-3-에톡시페닐, 2-히드록시-3-프로폭시페닐, 2-히드록시-3-부톡시페닐 또는 2-히드록시-3-펜톡시펜닐인 방법.
- 제16항에 있어서, 광학 활성 2차 아민 화합물(Ⅰ)이 N-(p-히드록시벤질)-1-페닐에틸아민, N-(p-히드록시벤질)-1-(p-톨릴)에틸아민, N-(p-히드록시벤질)-1-(p-이소프로필페닐)에틸아민, N-(p-히드록시벤질)-1-(p-브로모페닐)에틸아민, N-(p-히드록시벤질)-1-(1-나프틸)에틸아민, N-(p-히드록시벤질)-1-(P-니트로페닐)에틸아민, N-(P-히드록시벤질)-1-시클로헥실에틸아민, N-(p-히드록시벤질)-1-(p-메록시페닐)에틸아민, N-(2-히드록시-3-메톡시벤질)-1-페닐에틸아민, N-(2-히드록시-3-메톡시벤질)-1-(p-톨릴)에틸아민, N-(2-히드록시-3-메톡시벤질)-1-(p-이소프로필페닐)에틸아민, N-(2-히드록시-3-메톡시벤질)-1-(p-니트로페닐)에틸아민, N-(2-히드록시-3-메톡시벤질)-1-(p-브로모페닐)에틸아민, N-(2-히드록시-3-메톡시벤질)-1-(p-나프틸)에틸아민, N-(2-히드록시-3-메톡시벤질)-1-시클로헥실에틸아민, N-(2-히드록시-3-메톡시벤질)-1-(p-메톡시페닐)에틸아민 또는 N-p-히드록시벤질-α-페닐-β-p-톨릴에틸아민인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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| US6313146B1 (en) | 1991-08-23 | 2001-11-06 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6001884A (en) * | 1991-08-23 | 1999-12-14 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| CA2173747C (en) * | 1991-08-23 | 2006-05-23 | Edward F. Nemeth | Calcium receptor-active arylalkyl amines |
| US6031003A (en) * | 1991-08-23 | 2000-02-29 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US5858684A (en) * | 1991-08-23 | 1999-01-12 | The Brigham And Women's Hospital, Inc. | Method of screening calcium receptor-active molecules |
| US6011068A (en) * | 1991-08-23 | 2000-01-04 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US5763569A (en) * | 1991-08-23 | 1998-06-09 | The Brigham And Women's Hospital, Inc | Calcium receptor-active molecules |
| US5688938A (en) * | 1991-08-23 | 1997-11-18 | The Brigham & Women's Hospital, Inc. | Calcium receptor-active molecules |
| US5962314A (en) * | 1993-02-23 | 1999-10-05 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| CN1312116C (zh) * | 1994-10-21 | 2007-04-25 | Nps药物有限公司 | 钙受体活性化合物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4834736B1 (ko) * | 1969-05-14 | 1973-10-23 | ||
| US3739019A (en) * | 1969-07-02 | 1973-06-12 | Sumitomo Chemical Co | Preparation of optically active trans chrysanthemic acid |
| JPS5123497B2 (ko) * | 1972-01-07 | 1976-07-17 | ||
| JPS49109344A (ko) * | 1973-02-27 | 1974-10-17 | ||
| DE2826952A1 (de) * | 1978-06-20 | 1980-01-10 | Bayer Ag | Enantiomerentrennung von chiralen carbonsaeuren |
| JPS5910724B2 (ja) * | 1979-08-24 | 1984-03-10 | 旭化成株式会社 | エチレンの連続重合法 |
| US4259521A (en) * | 1979-10-09 | 1981-03-31 | American Cyanamid Company | Process for resolving DL-mandelic acid |
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| JPH0667871B2 (ja) * | 1986-07-31 | 1994-08-31 | 住友化学工業株式会社 | 第一菊酸の光学分割法 |
| US5011996A (en) * | 1988-07-20 | 1991-04-30 | Bayer Aktiengesellschaft | Process for the preparation of amines |
| US5191112A (en) * | 1989-10-17 | 1993-03-02 | Nissan Chemical Industries, Ltd. | Process for optical resolution of (±)-2-(3-benzoyl)-phenylpropionic acid |
-
1992
- 1992-04-02 DE DE69206306T patent/DE69206306T2/de not_active Expired - Lifetime
- 1992-04-02 DK DK92105682.6T patent/DK0508307T3/da active
- 1992-04-02 EP EP92105682A patent/EP0508307B1/en not_active Expired - Lifetime
- 1992-04-03 JP JP4081993A patent/JP3031048B2/ja not_active Expired - Fee Related
- 1992-04-06 US US07/863,976 patent/US5298660A/en not_active Expired - Lifetime
- 1992-04-07 CA CA002065476A patent/CA2065476C/en not_active Expired - Lifetime
- 1992-04-08 KR KR1019920005857A patent/KR100220266B1/ko not_active IP Right Cessation
- 1992-04-08 HU HU9201186A patent/HU214741B/hu unknown
-
1993
- 1993-12-13 US US08/165,716 patent/US5510519A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| HU9201186D0 (en) | 1992-07-28 |
| US5298660A (en) | 1994-03-29 |
| EP0508307B1 (en) | 1995-11-29 |
| EP0508307A3 (en) | 1993-02-03 |
| US5510519A (en) | 1996-04-23 |
| DE69206306D1 (de) | 1996-01-11 |
| JPH05201938A (ja) | 1993-08-10 |
| HU214741B (hu) | 1998-10-28 |
| JP3031048B2 (ja) | 2000-04-10 |
| EP0508307A2 (en) | 1992-10-14 |
| KR100220266B1 (ko) | 1999-10-01 |
| DK0508307T3 (da) | 1995-12-27 |
| CA2065476C (en) | 2003-10-14 |
| CA2065476A1 (en) | 1992-10-09 |
| HUT60995A (en) | 1992-11-30 |
| DE69206306T2 (de) | 1996-06-13 |
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