JPS6213347B2 - - Google Patents

Info

Publication number: JPS6213347B2
Authority: JP; Japan
Prior art keywords: mmol; general formula; diphenyl; substituted; solution
Prior art date: 1983-06-17
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.): Expired

Application number

JP58109807A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6075458A (ja

Inventor

Kiwa Takehira

Hajime Fujimura

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.)

1983-06-17

Filing date

1983-06-17

Publication date

1987-03-25

1983-06-17 Application filed by Osaka Soda Co Ltd filed Critical Osaka Soda Co Ltd

1983-06-17 Priority to JP58109807A priority Critical patent/JPS6075458A/ja

1985-04-27 Publication of JPS6075458A publication Critical patent/JPS6075458A/ja

1987-03-25 Publication of JPS6213347B2 publication Critical patent/JPS6213347B2/ja

Status Granted legal-status Critical Current

Links

-1 4-substituted benzylamine Chemical class 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
HCIBTBXNLVOFER-UHFFFAOYSA-N diphenylcyclopropenone Chemical compound O=C1C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 HCIBTBXNLVOFER-UHFFFAOYSA-N 0.000 claims description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
150000001875 compounds Chemical class 0.000 description 7
238000000034 method Methods 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 6
238000000921 elemental analysis Methods 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
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 4
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical group O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
ARCFAMFPEOETGL-UHFFFAOYSA-N 2,3-diphenylcycloprop-2-en-1-one;hydrate Chemical compound O.O=C1C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 ARCFAMFPEOETGL-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003814 drug Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 2
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
239000002253 acid Substances 0.000 description 2
229940121363 anti-inflammatory agent Drugs 0.000 description 2
239000002260 anti-inflammatory agent Substances 0.000 description 2
229940124599 anti-inflammatory drug Drugs 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 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
230000002401 inhibitory effect Effects 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000002994 raw material Substances 0.000 description 2
230000001629 suppression Effects 0.000 description 2
YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 description 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
QOEUNLQGZBSTBB-UHFFFAOYSA-N 1-methylazetidin-2-one Chemical compound CN1CCC1=O QOEUNLQGZBSTBB-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
206010039897 Sedation Diseases 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000003556 anti-epileptic effect Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000002221 antipyretic Substances 0.000 description 1
229940125717 barbiturate Drugs 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000003950 cyclic amides Chemical group 0.000 description 1
238000006352 cycloaddition reaction Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000001469 hydantoins Chemical class 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 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
229940121354 immunomodulator Drugs 0.000 description 1
229960000905 indomethacin Drugs 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
230000001379 nervous effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000003642 reactive oxygen metabolite Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
230000036280 sedation Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP58109807A 1983-06-17 1983-06-17 ３，４−ジフエニル−１−（４−置換）アリ−ルメチルアゼチジン−２−オンの製法 Granted JPS6075458A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP58109807A JPS6075458A (ja)	1983-06-17	1983-06-17	３，４−ジフエニル−１−（４−置換）アリ−ルメチルアゼチジン−２−オンの製法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP58109807A JPS6075458A (ja)	1983-06-17	1983-06-17	３，４−ジフエニル−１−（４−置換）アリ−ルメチルアゼチジン−２−オンの製法

Publications (2)

Publication Number	Publication Date
JPS6075458A JPS6075458A (ja)	1985-04-27
JPS6213347B2 true JPS6213347B2 (2)	1987-03-25

Family

ID=14519700

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58109807A Granted JPS6075458A (ja)	1983-06-17	1983-06-17	３，４−ジフエニル−１−（４−置換）アリ−ルメチルアゼチジン−２−オンの製法

Country Status (1)

Country	Link
JP (1)	JPS6075458A (2)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2193155T3 (es) *	1993-03-22	2003-11-01	Univ Florida State	Taxanos que tienen la cadena lateral sustituida por furilo o tienilo.

1983
- 1983-06-17 JP JP58109807A patent/JPS6075458A/ja active Granted

Also Published As

Publication number	Publication date
JPS6075458A (ja)	1985-04-27

Publication	Publication Date	Title
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MA27660A1 (fr)	2005-12-01	Derive heteroarylcarbamoylbenzene
US4699992A (en)	1987-10-13	3-amino-2-benzoylacrylic acid derivatives
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