KR950032224A - 아미노붕산 유도체, 그 제법 및 합성중간체로서 그것의 사용 - Google Patents
아미노붕산 유도체, 그 제법 및 합성중간체로서 그것의 사용 Download PDFInfo
- Publication number
- KR950032224A KR950032224A KR1019950008355A KR19950008355A KR950032224A KR 950032224 A KR950032224 A KR 950032224A KR 1019950008355 A KR1019950008355 A KR 1019950008355A KR 19950008355 A KR19950008355 A KR 19950008355A KR 950032224 A KR950032224 A KR 950032224A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- formula
- group
- alkyl group
- butanediol
- Prior art date
Links
- 239000000543 intermediate Substances 0.000 title abstract 2
- FMNFAXVBAQEWCV-UHFFFAOYSA-N aminooxyboronic acid Chemical class NOB(O)O FMNFAXVBAQEWCV-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 7
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 claims abstract 6
- 150000003839 salts Chemical class 0.000 claims abstract 4
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 claims abstract 3
- VUVZASHBYYMLRC-UHFFFAOYSA-N heptane-2,3-diol Chemical compound CCCCC(O)C(C)O VUVZASHBYYMLRC-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims 3
- -1 3-bromopropyl Chemical group 0.000 claims 2
- 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 1
- 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 1
- 239000002253 acid Substances 0.000 claims 1
- 239000000010 aprotic solvent Substances 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
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 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 1
- 150000002009 diols Chemical class 0.000 claims 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 235000009518 sodium iodide Nutrition 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
-
- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
본 발명은 식(I)의 화합물과 그 염, 합성중간체로서 그것의 사용에 관한 것이다.
상기식에서, R3와 R4는 함께, 예를들면 2,3-부탄디올, 2,3-디메틸-2,3-부탄디올 또는 (1α,3α,5α)-2,6,6-트리메틸비시클로[3.1.1] 헵탄-2,3-디올[(+)-α-피난디올]과 같은 디히드록실화 화합물의 잔기를 나타내며, R3는 수소원자 또는 순수하거나 혼합물의 형태인 광학적 또는 기하학적 이성질체 형태의 (C1-C4)알킬기를 나타낸다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (4)
- 식(I)의 화합물 또는 그 염상기식에서, R3와 R4는 함께, 디히드록시 화합물의 잔기를 나타내며, R5는 수소원자 또는 (C1-C4)알킬기를 나타낸다.
- 제1항에 있어서, R3와 R4는 함께, 2,3-부탄디올, 2,3-디메틸-2,3-부탄디올 또는 (1α,3α,5α)-2,6,6-트리메틸비시클로[3.1.1] 헵탄-2,3-디올[(+)-α-피난디올]의 잔기를 나타내는 것을 특징으로 하는 화합물 또는 그 염.
- 식(IV)의 [3aS-(3aα,4β,6β,7aα)]-2-(3-브로모프로필)-3a,5,5-트리메틸헥사히드로-4,6-메탄오-1,3,2-벤조디옥사보롤을 비양성자성 용매내에서 요오드화 나트륨과 반응시키고, 그 다음 이와같이 얻어진 식(V)의 [3aS-(3aα,4β,6β,7aα)]-2-(3-요오도프로필)-3a,5,5-트리메틸헥사히드로-4,6-메탄오-1,3,2-벤조디옥사보롤을 식(VI)(상기식에서 R5는 수소원자 또는 (C1-C4)알킬기를 나타낸다)의 화합물과 축합시켜 식(VII)의 화합물을 형성하고, 이것을 디클로로메틸리튬과 반응시켜서 식(VIII)의 화합물을 얻고, 이것을 리튬 비스(트리메틸실릴) 아미드와 반응시켜서 화합물을 형성하고 이것을 염산으로 처리하여 식(IX)의 염산염을 얻고 이것을 가수분해하여 식(X)의 (R)-α-아미노붕산의 이염산염을 얻고 이것을 R3와 R4가 함께, 제1항에 정의된 바와같은 디히록실화 화합물의 잔기를 나타내는 식(XI)의 디올과 반응시켜서 식(I)의 화합물을 얻는것을 특징으로 하는 제1항에 따른 화합물의 제조방법.
- 식(1)의 호합물의 합성을 위한 제1항에 따른 화합물의 사용.상기식에서, R은 수소원자이거나 직쇄 또는 분지쇄(C1-C4)알킬기, -COR′기(식중 R′은 직쇄 또는 분지쇄(C1-C4)알킬기이다), 및 -(CH2)nCO2R″기 (식중 R″은 수소운자이거나 직쇄 또는 분지쇄(C1-C4)알킬기 또는 페닐메틸기이며 n은 0 내지 2이다)로 부터 선택된 기를 나타내며, R1은 페닐기 또는 1-나프틸기 또는 2-나프틸기 또는 시클로헥실기를 나타내며, R3와 R4는 함께, 예를들면 2,3-부탄디올, 2,3-디메틸-2,3-부탄디올 또는 (1α,3α,5α)-2,6,6-트리메틸비시클로[3.1.1] 헵탄-2,3-디올[(+)-α-피난디올]과 같은 디히드록실화 화합물의 잔기를 나타내며, R5는 수소원자 또는 (C1-C4)알킬기를 나타낸다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR94.04287 | 1994-04-12 | ||
| FR9404287A FR2718448B3 (fr) | 1994-04-12 | 1994-04-12 | Dérivés d'acides aminoboroniques, leur préparation et leur utilisation comme intermédiaires de synthèse. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR950032224A true KR950032224A (ko) | 1995-12-20 |
Family
ID=9461980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019950008355A KR950032224A (ko) | 1994-04-12 | 1995-04-11 | 아미노붕산 유도체, 그 제법 및 합성중간체로서 그것의 사용 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5543526A (ko) |
| EP (1) | EP0677525A1 (ko) |
| JP (1) | JPH07278155A (ko) |
| KR (1) | KR950032224A (ko) |
| CA (1) | CA2146832A1 (ko) |
| FI (1) | FI951725A (ko) |
| FR (1) | FR2718448B3 (ko) |
| IL (1) | IL113331A (ko) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5639739A (en) * | 1995-03-24 | 1997-06-17 | The Dupont Merck Pharmaceutical Company | Imidazole containing aminoboronic acids |
| FR2758326B1 (fr) * | 1997-01-16 | 1999-02-12 | Synthelabo | Derives de pyridone, leur prepaparation et leur utilisation comme intermediaires de synthese |
| US6008353A (en) * | 1997-10-07 | 1999-12-28 | Rhone-Poulenc Inc. | Pesticidal 1-arylpyrazole boranes |
| WO2002054931A2 (en) * | 2001-01-10 | 2002-07-18 | Bristol Myers Squibb Company P | Alpha-aminoboronic acids prepared by novel synthetic methods |
| US7537827B1 (en) * | 2006-12-13 | 2009-05-26 | Henkel Corporation | Prepreg laminates |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4298486A (en) * | 1979-11-23 | 1981-11-03 | Mobil Oil Corporation | Friction reducing additives and compositions thereof |
| US4537773A (en) * | 1983-12-05 | 1985-08-27 | E. I. Du Pont De Nemours And Company | α-Aminoboronic acid derivatives |
| EP0157969B2 (en) * | 1984-04-05 | 2000-01-12 | The Lubrizol Corporation | Organo-borate compositions and their use in lubricants |
| US4554086A (en) * | 1984-04-26 | 1985-11-19 | Texaco Inc. | Borate esters of hydrocarbyl-substituted mono- and bis-succinimides containing polyamine chain linked hydroxyacyl groups and lubricating oil compositions containing same |
| US5187157A (en) * | 1987-06-05 | 1993-02-16 | Du Pont Merck Pharmaceutical Company | Peptide boronic acid inhibitors of trypsin-like proteases |
| US4963655A (en) * | 1988-05-27 | 1990-10-16 | Mayo Foundation For Medical Education And Research | Boron analogs of amino acid/peptide protease inhibitors |
| JPH05239069A (ja) * | 1992-02-28 | 1993-09-17 | Canon Inc | 液晶性化合物、これを含む液晶組成物、それを有する液晶素子、それらを用いた表示方法および表示装置 |
-
1994
- 1994-04-12 FR FR9404287A patent/FR2718448B3/fr not_active Expired - Lifetime
-
1995
- 1995-04-07 EP EP95400775A patent/EP0677525A1/fr not_active Withdrawn
- 1995-04-11 KR KR1019950008355A patent/KR950032224A/ko not_active Application Discontinuation
- 1995-04-11 CA CA002146832A patent/CA2146832A1/fr not_active Abandoned
- 1995-04-11 IL IL11333195A patent/IL113331A/xx not_active IP Right Cessation
- 1995-04-11 US US08/419,923 patent/US5543526A/en not_active Expired - Fee Related
- 1995-04-11 FI FI951725A patent/FI951725A/fi unknown
- 1995-04-11 JP JP7085414A patent/JPH07278155A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FI951725A (fi) | 1995-10-13 |
| IL113331A0 (en) | 1995-07-31 |
| FI951725A0 (fi) | 1995-04-11 |
| CA2146832A1 (fr) | 1995-10-13 |
| FR2718448A3 (fr) | 1995-10-13 |
| JPH07278155A (ja) | 1995-10-24 |
| IL113331A (en) | 1999-11-30 |
| EP0677525A1 (fr) | 1995-10-18 |
| US5543526A (en) | 1996-08-06 |
| FR2718448B3 (fr) | 1996-02-09 |
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| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |