KR20190000592A - 알킬 디에틸렌 트리아민 유도체 및 이의 제조방법 - Google Patents
알킬 디에틸렌 트리아민 유도체 및 이의 제조방법 Download PDFInfo
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- KR20190000592A KR20190000592A KR1020170079784A KR20170079784A KR20190000592A KR 20190000592 A KR20190000592 A KR 20190000592A KR 1020170079784 A KR1020170079784 A KR 1020170079784A KR 20170079784 A KR20170079784 A KR 20170079784A KR 20190000592 A KR20190000592 A KR 20190000592A
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- 238000000034 method Methods 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 Alkyl diethylene triamine derivatives Chemical class 0.000 title abstract description 9
- 150000001412 amines Chemical class 0.000 claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 150000003973 alkyl amines Chemical class 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000005658 halogenation reaction Methods 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000004065 semiconductor Substances 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 239000003446 ligand Substances 0.000 abstract description 3
- 150000004696 coordination complex Chemical class 0.000 abstract description 2
- 230000008021 deposition Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 0 *C(CN(*)CC(*)O)O Chemical compound *C(CN(*)CC(*)O)O 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- HYSQEYLBJYFNMH-UHFFFAOYSA-N n'-(2-aminoethyl)-n'-methylethane-1,2-diamine Chemical compound NCCN(C)CCN HYSQEYLBJYFNMH-UHFFFAOYSA-N 0.000 description 2
- KHUIPWWXWPKLEF-UHFFFAOYSA-N n-(2-iodoethyl)-n,4-dimethylbenzenesulfonamide Chemical compound ICCN(C)S(=O)(=O)C1=CC=C(C)C=C1 KHUIPWWXWPKLEF-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- KGLJRLNYNFBIME-UHFFFAOYSA-N CN(CCN(C)S(c1ccccc1[N+]([O-])=O)(=O)=O)CCN(C)S(c(cccc1)c1[N+]([O-])=O)(=O)=O Chemical compound CN(CCN(C)S(c1ccccc1[N+]([O-])=O)(=O)=O)CCN(C)S(c(cccc1)c1[N+]([O-])=O)(=O)=O KGLJRLNYNFBIME-UHFFFAOYSA-N 0.000 description 1
- VDWWEGDRUZXEEA-UHFFFAOYSA-N CN(CCN)CCNS(c1ccccc1[N+]([O-])=O)(=O)=O Chemical compound CN(CCN)CCNS(c1ccccc1[N+]([O-])=O)(=O)=O VDWWEGDRUZXEEA-UHFFFAOYSA-N 0.000 description 1
- KCDDRDWVTQAVKH-UHFFFAOYSA-N CN(CCNS(c(cccc1)c1[N+]([O-])=O)(=O)=O)CCNS(c1ccccc1[N+]([O-])=O)(=O)=O Chemical compound CN(CCNS(c(cccc1)c1[N+]([O-])=O)(=O)=O)CCNS(c1ccccc1[N+]([O-])=O)(=O)=O KCDDRDWVTQAVKH-UHFFFAOYSA-N 0.000 description 1
- ODZZIKZQNODXFS-UHFFFAOYSA-N CNCCN(C)CCNC Chemical compound CNCCN(C)CCNC ODZZIKZQNODXFS-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- WPHUUIODWRNJLO-UHFFFAOYSA-N [O-][N+](c(cccc1)c1S(Cl)(=O)=O)=O Chemical compound [O-][N+](c(cccc1)c1S(Cl)(=O)=O)=O WPHUUIODWRNJLO-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/90—Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/13—Amines containing three or more amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C211/15—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins
-
- 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
- C07C215/10—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 with one amino group and at least two hydroxy groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
-
- H01L51/005—
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (8)
- 알킬 디에틸렌 트리아민 유도체의 제조방법에 있어서,
a) 하기 반응식 1로 표시되고, 하기 화학식 4로 나타내는 에틸렌옥사이드을 알킬아민과 반응시켜 하기 화학식 2로 나타내는 디하이드록시 디에틸렌 아민을 제조하는 단계;
<반응식 1>
b) 하기 반응식 2로 표시되고, 하기 화학식 2로 나타내는 디하이드록시 디에틸렌 아민의 수산기(OH)를 할로겐기로 치환하는 단계;
<반응식 2>
<반응식 3>
c) 상기 반응식 3으로 표시되고, 할로겐기로 치환된 디에틸렌 아민과 알킬아민 수용액을 반응시켜 상기 화학식 1로 표시되는 알킬 디에틸렌 트리아민 유도체를 제조하는 단계;를 포함하는 것을 특징으로 하는 알킬 디에틸렌 트리아민 유도체의 제조방법
{상기 반응식 2 및 3에서,
X는 Cl, Br 또는 I를 나타내고,
R, R1 및 R2는 각각 독립적으로 수소, C1-C6 알킬기로 치환 또는 비치환된 C1-C6 알킬기를 나타낸다.}
- 제 1항에 있어서,
상기 에틸렌옥사이드 1 당량에 상기 알킬아민 2 당량을 반응시키는 것을 특징으로 하는 알킬 디에틸렌 트리아민 유도체의 제조방법
- 제 1항에 있어서,
상기 반응식 2 및 3에서 X는 Cl인 것을 특징으로 하는 알킬 디에틸렌 트리아민 유도체의 제조방법
- 제 3항에 있어서,
상기 반응식 2에서 할로겐화 반응은 SOCl2로 하는 것을 특징으로 하는 알킬 디에틸렌 트리아민 유도체의 제조방법
- 제 1항에 있어서,
상기 화학식 1의 R 및 R1은 동시에 메틸인 것을 특징으로 하는 알킬 디에틸렌 트리아민 유도체의 제조방법
- 제 1항에 있어서,
상기 화학식 1의 R2는 메틸, 에틸, 프로필, 이소프로필 또는 t-부틸인 것을 특징으로 하는 알킬 디에틸렌 트리아민 유도체의 제조방법
- 제 1항에 있어서,
상기 화학식 1의 R 및 R1은 동시에 메틸이고, R2는 메틸, 에틸, 이소프로필 또는 t-부틸인 것을 특징으로 하는 알킬 디에틸렌 트리아민 유도체의 제조방법
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Citations (3)
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---|---|---|---|---|
US2619502A (en) | 1950-06-23 | 1952-11-25 | Gen Aniline & Film Corp | N,n''-dibenzyl-n,n',n''-trialkyl-dialkylene triamines |
EP0670316A1 (en) | 1994-03-01 | 1995-09-06 | MITSUI TOATSU CHEMICALS, Inc. | 1,3,6-Trialkylhexahydro-1,3,6-triazocine-2-one and preparation process thereof |
WO2010003658A1 (en) | 2008-07-08 | 2010-01-14 | Tibotec Pharmaceuticals | Macrocyclic indole derivatives useful as hepatitis c virus inhibitors |
-
2017
- 2017-06-23 KR KR1020170079784A patent/KR101974388B1/ko active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2619502A (en) | 1950-06-23 | 1952-11-25 | Gen Aniline & Film Corp | N,n''-dibenzyl-n,n',n''-trialkyl-dialkylene triamines |
EP0670316A1 (en) | 1994-03-01 | 1995-09-06 | MITSUI TOATSU CHEMICALS, Inc. | 1,3,6-Trialkylhexahydro-1,3,6-triazocine-2-one and preparation process thereof |
WO2010003658A1 (en) | 2008-07-08 | 2010-01-14 | Tibotec Pharmaceuticals | Macrocyclic indole derivatives useful as hepatitis c virus inhibitors |
Non-Patent Citations (2)
Title |
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Tetrahedron Letters, Vol. 33, No. 16, 2203-2206(1992). |
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