JPS5883685A - イソキサゾリジン誘導体 - Google Patents

イソキサゾリジン誘導体

Info

Publication number: JPS5883685A
Authority: JP; Japan
Prior art keywords: formula; reacted; give; benzyl; group
Prior art date: 1981-11-12
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

JP56181398A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0160025B2 (2

Inventor

Tetsuji Kametani

亀谷　哲治

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Daiichi Pharmaceutical Co Ltd

Original Assignee

Daiichi Pharmaceutical Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1981-11-12

Filing date

1981-11-12

Publication date

1983-05-19

1981-11-12 Application filed by Daiichi Pharmaceutical Co Ltd filed Critical Daiichi Pharmaceutical Co Ltd

1981-11-12 Priority to JP56181398A priority Critical patent/JPS5883685A/ja

1983-05-19 Publication of JPS5883685A publication Critical patent/JPS5883685A/ja

1989-12-20 Publication of JPH0160025B2 publication Critical patent/JPH0160025B2/ja

Status Granted legal-status Critical Current

Links

150000002546 isoxazolidines Chemical class 0.000 title description 3
-1 (substituted) benzyl group Chemical group 0.000 claims abstract description 13
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
150000001875 compounds Chemical class 0.000 abstract description 13
125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract description 4
150000002443 hydroxylamines Chemical class 0.000 abstract description 3
239000003795 chemical substances by application Substances 0.000 abstract description 2
230000002140 halogenating effect Effects 0.000 abstract description 2
238000000034 method Methods 0.000 abstract description 2
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 abstract description 2
239000003242 anti bacterial agent Substances 0.000 abstract 1
229940088710 antibiotic agent Drugs 0.000 abstract 1
239000000463 material Substances 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 8
239000002904 solvent Substances 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 6
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
238000010898 silica gel chromatography Methods 0.000 description 6
238000010531 catalytic reduction reaction Methods 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
238000010992 reflux Methods 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000003921 oil Substances 0.000 description 3
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000012454 non-polar solvent Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
JJVODHIRRAFJDE-UHFFFAOYSA-N 2-(hydroxyamino)-2-phenylacetic acid Chemical compound ONC(C(O)=O)C1=CC=CC=C1 JJVODHIRRAFJDE-UHFFFAOYSA-N 0.000 description 1
NWIVYGKSHSJHEF-UHFFFAOYSA-N 4-[(4-amino-3,5-diethylphenyl)methyl]-2,6-diethylaniline Chemical compound CCC1=C(N)C(CC)=CC(CC=2C=C(CC)C(N)=C(CC)C=2)=C1 NWIVYGKSHSJHEF-UHFFFAOYSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
239000005973 Carvone Substances 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
102100028138 F-box/WD repeat-containing protein 7 Human genes 0.000 description 1
229910002604 Ga-H Inorganic materials 0.000 description 1
101001060231 Homo sapiens F-box/WD repeat-containing protein 7 Proteins 0.000 description 1
101100080050 Oryza sativa subsp. japonica NIP2-2 gene Proteins 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
WGQKYBSKWIADBV-UHFFFAOYSA-N aminomethyl benzene Natural products NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical group [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000004020 conductor Substances 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
150000002148 esters Chemical group 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
RRJRFNUPXQLYHX-UHFFFAOYSA-N n-(1-phenylethyl)hydroxylamine Chemical compound ONC(C)C1=CC=CC=C1 RRJRFNUPXQLYHX-UHFFFAOYSA-N 0.000 description 1
LVCDXCQFSONNDO-UHFFFAOYSA-N n-benzylhydroxylamine Chemical compound ONCC1=CC=CC=C1 LVCDXCQFSONNDO-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)

JP56181398A 1981-11-12 1981-11-12 イソキサゾリジン誘導体 Granted JPS5883685A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP56181398A JPS5883685A (ja)	1981-11-12	1981-11-12	イソキサゾリジン誘導体

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP56181398A JPS5883685A (ja)	1981-11-12	1981-11-12	イソキサゾリジン誘導体

Publications (2)

Publication Number	Publication Date
JPS5883685A true JPS5883685A (ja)	1983-05-19
JPH0160025B2 JPH0160025B2 (2)	1989-12-20

Family

ID=16100042

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP56181398A Granted JPS5883685A (ja)	1981-11-12	1981-11-12	イソキサゾリジン誘導体

Country Status (1)

Country	Link
JP (1)	JPS5883685A (2)

1981
- 1981-11-12 JP JP56181398A patent/JPS5883685A/ja active Granted

Also Published As

Publication number	Publication date
JPH0160025B2 (2)	1989-12-20

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