JPS6075457A - ３，４−ジフェニル−１−ベンジルアゼチジン−２−オンの製法 - Google Patents

３，４−ジフェニル−１−ベンジルアゼチジン−２−オンの製法

Info

Publication number: JPS6075457A
Authority: JP; Japan
Prior art keywords: diphenyl; formula; benzylamine; room temperature; compound
Prior art date: 1983-06-11
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

JP58104639A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6217998B2 (2

Inventor

Kiwa Takehira

竹平　喜和

Fumio Toda

芙三夫戸田

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.)

Osaka Soda Co Ltd

Original Assignee

Osaka Soda 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.)

1983-06-11

Filing date

1983-06-11

Publication date

1985-04-27

1983-06-11 Application filed by Osaka Soda Co Ltd filed Critical Osaka Soda Co Ltd

1983-06-11 Priority to JP58104639A priority Critical patent/JPS6075457A/ja

1985-04-27 Publication of JPS6075457A publication Critical patent/JPS6075457A/ja

1987-04-21 Publication of JPS6217998B2 publication Critical patent/JPS6217998B2/ja

Status Granted legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 7
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims abstract description 16
HCIBTBXNLVOFER-UHFFFAOYSA-N diphenylcyclopropenone Chemical compound O=C1C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 HCIBTBXNLVOFER-UHFFFAOYSA-N 0.000 claims abstract description 3
RAEHAMXZQABPBO-UHFFFAOYSA-N 1-benzyl-3,4-diphenylazetidin-2-one Chemical compound O=C1C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)N1CC1=CC=CC=C1 RAEHAMXZQABPBO-UHFFFAOYSA-N 0.000 claims description 5
150000001875 compounds Chemical class 0.000 abstract description 9
238000000034 method Methods 0.000 abstract description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 7
238000006243 chemical reaction Methods 0.000 abstract description 7
239000001301 oxygen Substances 0.000 abstract description 7
229910052760 oxygen Inorganic materials 0.000 abstract description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
239000002260 anti-inflammatory agent Substances 0.000 abstract description 5
239000003795 chemical substances by application Substances 0.000 abstract description 4
230000002401 inhibitory effect Effects 0.000 abstract description 4
239000002253 acid Substances 0.000 abstract description 3
239000003960 organic solvent Substances 0.000 abstract description 3
229910052783 alkali metal Inorganic materials 0.000 abstract description 2
150000001340 alkali metals Chemical class 0.000 abstract description 2
230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
230000001754 anti-pyretic effect Effects 0.000 abstract description 2
239000002221 antipyretic Substances 0.000 abstract description 2
-1 e.g. Substances 0.000 abstract description 2
239000012433 hydrogen halide Substances 0.000 abstract description 2
229910000039 hydrogen halide Inorganic materials 0.000 abstract description 2
230000001105 regulatory effect Effects 0.000 abstract description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
230000000202 analgesic effect Effects 0.000 abstract 1
230000003266 anti-allergic effect Effects 0.000 abstract 1
230000001741 anti-phlogistic effect Effects 0.000 abstract 1
238000004587 chromatography analysis Methods 0.000 abstract 1
230000001900 immune effect Effects 0.000 abstract 1
239000000463 material Substances 0.000 abstract 1
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
229940121363 anti-inflammatory agent Drugs 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000126 substance Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000000370 acceptor Substances 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 2
238000007429 general method Methods 0.000 description 2
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000002994 raw material Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
FYLYJFHGDNQLJJ-UHFFFAOYSA-N 1-benzylazetidin-2-one Chemical compound O=C1CCN1CC1=CC=CC=C1 FYLYJFHGDNQLJJ-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000003556 anti-epileptic effect Effects 0.000 description 1
230000000573 anti-seizure effect Effects 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
150000003950 cyclic amides Chemical group 0.000 description 1
238000006352 cycloaddition reaction Methods 0.000 description 1
229960001193 diclofenac sodium Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
229940091173 hydantoin Drugs 0.000 description 1
230000000147 hypnotic effect Effects 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
239000002955 immunomodulating agent Substances 0.000 description 1
230000002584 immunomodulator Effects 0.000 description 1
229940121354 immunomodulator Drugs 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000000203 mixture Substances 0.000 description 1
210000003024 peritoneal macrophage Anatomy 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000003642 reactive oxygen metabolite Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
JGMJQSFLQWGYMQ-UHFFFAOYSA-M sodium;2,6-dichloro-n-phenylaniline;acetate Chemical compound [Na+].CC([O-])=O.ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 JGMJQSFLQWGYMQ-UHFFFAOYSA-M 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000001629 suppression Effects 0.000 description 1
SBUXRMKDJWEXRL-ZWKOTPCHSA-N trans-body Chemical compound O=C([C@@H]1N(C2=O)[C@H](C3=C(C4=CC=CC=C4N3)C1)CC)N2C1=CC=C(F)C=C1 SBUXRMKDJWEXRL-ZWKOTPCHSA-N 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP58104639A 1983-06-11 1983-06-11 ３，４−ジフェニル−１−ベンジルアゼチジン−２−オンの製法 Granted JPS6075457A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP58104639A JPS6075457A (ja)	1983-06-11	1983-06-11	３，４−ジフェニル−１−ベンジルアゼチジン−２−オンの製法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP58104639A JPS6075457A (ja)	1983-06-11	1983-06-11	３，４−ジフェニル−１−ベンジルアゼチジン−２−オンの製法

Publications (2)

Publication Number	Publication Date
JPS6075457A true JPS6075457A (ja)	1985-04-27
JPS6217998B2 JPS6217998B2 (2)	1987-04-21

Family

ID=14386016

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58104639A Granted JPS6075457A (ja)	1983-06-11	1983-06-11	３，４−ジフェニル−１−ベンジルアゼチジン−２−オンの製法

Country Status (1)

Country	Link
JP (1)	JPS6075457A (2)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2008033468A3 (en) *	2006-09-15	2008-08-14	Schering Corp	Azetidine and azetidone derivatives useful in treating pain and disorders of lipid metabolism
US7638526B2 (en)	2006-09-15	2009-12-29	Schering Corporation	Azetidine derivatives useful in treating pain, diabetes and disorders of lipid metabolism

1983
- 1983-06-11 JP JP58104639A patent/JPS6075457A/ja active Granted

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2008033468A3 (en) *	2006-09-15	2008-08-14	Schering Corp	Azetidine and azetidone derivatives useful in treating pain and disorders of lipid metabolism
US7638526B2 (en)	2006-09-15	2009-12-29	Schering Corporation	Azetidine derivatives useful in treating pain, diabetes and disorders of lipid metabolism
US7902157B2 (en)	2006-09-15	2011-03-08	Schering Corporation	Azetidine and azetidone derivatives useful in treating pain and disorders of lipid metabolism

Also Published As

Publication number	Publication date
JPS6217998B2 (2)	1987-04-21

Publication	Publication Date	Title
DE69717268T2 (de)	2003-09-04	M-amidinophenyl-analoga als faktor-xa-inhibitoren
JP3262810B2 (ja)	2002-03-04	ケトンの還元用キラル触媒とその製法
JPS6075457A (ja)	1985-04-27	３，４−ジフェニル−１−ベンジルアゼチジン−２−オンの製法
Lee et al.	2002	Investigation of the Cyclization of N-(2-Hydroxyethyl)-N'-phenylthioureas: Mitsunobu Conditions vs TsCl/NaOH System
US4172946A (en)	1979-10-30	Method for manufacture of fluoroalkyl pyridines
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JPS61286394A (ja)	1986-12-16	オレフイン性シラザンの製造方法
CN120647641B (zh)	2026-03-13	一种噁二唑取代的1,2,3-三唑类化合物的制备方法
Mazurkiewicz et al.	2000	A NEW SYNTHESIS OF α-AMINO ACID DERIVATIVES BY REACTION OF N-ACYL-α-TRIPHENYLPHOSPHOSPHONIO-GLYCINATES WITH CARBON NUCLEOPHILES
SU642299A1 (ru)	1979-01-15	Способ получени трицина
JPS62230759A (ja)	1987-10-09	新規アクリルまたはメタクリルアミド誘導体
JPS6310143B2 (2)	1988-03-04
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US4162264A (en)	1979-07-24	Process for preparing diphenylphosphinylacetic acid hydrazide
KR890002556B1 (ko)	1989-07-18	아지드 화합물의 제조방법
JPH0124788B2 (2)	1989-05-15
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NO144887B (no)	1981-08-24	Fremgangsmaate for fremstilling av 1-(tetrahydro-2-furyl)-5-fluoruracil, av 1,3-bis-(tetrahydro-2-furyl)-5-fluor-uracil eller av en blanding av disse
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JPH01313471A (ja)	1989-12-18	Ｎ−スルフアモイルアミジン化合物の製造法
JPH06145168A (ja)	1994-05-24	４−（４−クロロベンジル）−２−〔ｎ−メチル−パーヒドロアゼピニル−（４）〕−１−（２ｈ）−フタラジノン及びその酸付加塩の製造方法
JPS63192747A (ja)	1988-08-10	ホルムアミジンのギ酸塩