JPS60152483A - チオフエン誘導体及びその製造方法 - Google Patents

チオフエン誘導体及びその製造方法

Info

Publication number: JPS60152483A
Authority: JP; Japan
Prior art keywords: formula; general formula; carbon atoms; derivative; thiophene
Prior art date: 1984-01-20
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

JP930384A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0262553B2 (de

Inventor

Michihiro Kobayashi

通洋小林

Makio Kitazawa

牧雄北澤

Takenao Saito

齊藤　武直

Ryoji Yamamoto

亮治山本

Hiroshi Harada

弘原田

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.)

Kissei Pharmaceutical Co Ltd

Original Assignee

Kissei Pharmaceutical Co Ltd

Kissei Yakuhin Kogyo KK

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.)

1984-01-20

Filing date

1984-01-20

Publication date

1985-08-10

1984-01-20 Application filed by Kissei Pharmaceutical Co Ltd, Kissei Yakuhin Kogyo KK filed Critical Kissei Pharmaceutical Co Ltd

1984-01-20 Priority to JP930384A priority Critical patent/JPS60152483A/ja

1985-08-10 Publication of JPS60152483A publication Critical patent/JPS60152483A/ja

1990-12-26 Publication of JPH0262553B2 publication Critical patent/JPH0262553B2/ja

Status Granted legal-status Critical Current

Links

150000003577 thiophenes Chemical class 0.000 title claims description 7
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
125000002947 alkylene group Chemical group 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims 2
150000001875 compounds Chemical class 0.000 abstract description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 9
LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 abstract description 8
-1 phenylalkyl carboxylic acid Chemical class 0.000 abstract description 5
HVLUYXIJZLDNIS-UHFFFAOYSA-N 2-thiophen-2-ylethanamine Chemical compound NCCC1=CC=CS1 HVLUYXIJZLDNIS-UHFFFAOYSA-N 0.000 abstract description 3
208000025865 Ulcer Diseases 0.000 abstract description 2
231100000397 ulcer Toxicity 0.000 abstract description 2
VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 abstract 1
239000003795 chemical substances by application Substances 0.000 abstract 1
210000001198 duodenum Anatomy 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
230000002401 inhibitory effect Effects 0.000 abstract 1
239000000463 material Substances 0.000 abstract 1
210000002784 stomach Anatomy 0.000 abstract 1
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
238000000034 method Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
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 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000002994 raw material Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
208000007107 Stomach Ulcer Diseases 0.000 description 2
238000000862 absorption spectrum Methods 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
230000003110 anti-inflammatory effect Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
208000000718 duodenal ulcer Diseases 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
230000002265 prevention Effects 0.000 description 2
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 2
VAYWLNRNWZOIAG-UHFFFAOYSA-N 2-(5-methylthiophen-2-yl)ethanamine Chemical compound CC1=CC=C(CCN)S1 VAYWLNRNWZOIAG-UHFFFAOYSA-N 0.000 description 1
XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
OANLWIQYRRVBPY-UHFFFAOYSA-N 2-thiophen-3-ylethanamine Chemical compound NCCC=1C=CSC=1 OANLWIQYRRVBPY-UHFFFAOYSA-N 0.000 description 1
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 1
241001282110 Pagrus major Species 0.000 description 1
241000700159 Rattus Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
208000002399 aphthous stomatitis Diseases 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000037396 body weight Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
229940047583 cetamide Drugs 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000003756 stirring Methods 0.000 description 1
FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1

Landscapes

Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP930384A 1984-01-20 1984-01-20 チオフエン誘導体及びその製造方法 Granted JPS60152483A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP930384A JPS60152483A (ja)	1984-01-20	1984-01-20	チオフエン誘導体及びその製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP930384A JPS60152483A (ja)	1984-01-20	1984-01-20	チオフエン誘導体及びその製造方法

Publications (2)

Publication Number	Publication Date
JPS60152483A true JPS60152483A (ja)	1985-08-10
JPH0262553B2 JPH0262553B2 (de)	1990-12-26

Family

ID=11716698

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP930384A Granted JPS60152483A (ja)	1984-01-20	1984-01-20	チオフエン誘導体及びその製造方法

Country Status (1)

Country	Link
JP (1)	JPS60152483A (de)

1984
- 1984-01-20 JP JP930384A patent/JPS60152483A/ja active Granted

Also Published As

Publication number	Publication date
JPH0262553B2 (de)	1990-12-26

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