JPH0557985B2 - - Google Patents

Info

Publication number: JPH0557985B2
Authority: JP; Japan
Prior art keywords: formula; derivative represented; acid amide; group; thiazolecarboxylic acid
Prior art date: 1985-01-16
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 - Lifetime

Application number

JP408885A

Other languages

English (en)

Japanese (ja)

Other versions

JPS61165376A (ja

Inventor

Masahito Takahashi

Toshio Sato

Yoshitaka Kuroda

Toshihiko Kimata

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.)

Godo Shusei KK

Original Assignee

Godo Shusei 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.)

1985-01-16

Filing date

1985-01-16

Publication date

1993-08-25

1985-01-16 Application filed by Godo Shusei KK filed Critical Godo Shusei KK

1985-01-16 Priority to JP408885A priority Critical patent/JPS61165376A/ja

1986-07-26 Publication of JPS61165376A publication Critical patent/JPS61165376A/ja

1993-08-25 Publication of JPH0557985B2 publication Critical patent/JPH0557985B2/ja

Status Granted legal-status Critical Current

Links

-1 carboxyphenyl group Chemical group 0.000 claims description 33
IJVLVRYLIMQVDD-UHFFFAOYSA-N 1,3-thiazole-2-carboxylic acid Chemical compound OC(=O)C1=NC=CS1 IJVLVRYLIMQVDD-UHFFFAOYSA-N 0.000 claims description 20
238000004519 manufacturing process Methods 0.000 claims description 8
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 7
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 3
230000003301 hydrolyzing effect Effects 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
150000004820 halides Chemical class 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
150000001875 compounds Chemical class 0.000 description 7
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 5
238000000746 purification Methods 0.000 description 5
238000000862 absorption spectrum Methods 0.000 description 4
229910001854 alkali hydroxide Inorganic materials 0.000 description 4
150000008044 alkali metal hydroxides Chemical class 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000005457 ice water Substances 0.000 description 4
238000001819 mass spectrum Methods 0.000 description 4
238000000034 method Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
PQQRHWFRZHFGFM-UHFFFAOYSA-N 1,3-thiazole-4-carboxamide Chemical compound NC(=O)C1=CSC=N1 PQQRHWFRZHFGFM-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
206010030113 Oedema Diseases 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003513 alkali Substances 0.000 description 3
239000012670 alkaline solution Substances 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
239000002585 base Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
230000002140 halogenating effect Effects 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000002504 physiological saline solution Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
HMVYYTRDXNKRBQ-UHFFFAOYSA-N 1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC=N1 HMVYYTRDXNKRBQ-UHFFFAOYSA-N 0.000 description 2
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
230000002757 inflammatory effect Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
AETDFAXPCFASDB-UHFFFAOYSA-N pulicatin F Chemical compound NC(=O)C1=CSC(C=2C(=CC=CC=2)O)=N1 AETDFAXPCFASDB-UHFFFAOYSA-N 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
UCVBEULMPJTLLH-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC(C=2C(=CC=CC=2)O)=N1 UCVBEULMPJTLLH-UHFFFAOYSA-N 0.000 description 1
YSKMZPAUCUGNFT-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-1,3-thiazole-4-carboxylic acid Chemical compound OC(=O)C1=CSC(C=2C=CC(O)=CC=2)=N1 YSKMZPAUCUGNFT-UHFFFAOYSA-N 0.000 description 1
QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229960004050 aminobenzoic acid Drugs 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
238000010171 animal model Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
229940113118 carrageenan Drugs 0.000 description 1
235000010418 carrageenan Nutrition 0.000 description 1
229920001525 carrageenan Polymers 0.000 description 1
239000000679 carrageenan Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000010586 diagram Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
XCPXPFNKTCFWTA-UHFFFAOYSA-N ethyl carbonobromidate Chemical compound CCOC(Br)=O XCPXPFNKTCFWTA-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
210000000548 hind-foot Anatomy 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
QQHNGZNHRRLNKI-UHFFFAOYSA-N methyl carbonobromidate Chemical compound COC(Br)=O QQHNGZNHRRLNKI-UHFFFAOYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
210000003200 peritoneal cavity Anatomy 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000011403 purification operation Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
230000001629 suppression Effects 0.000 description 1
238000010998 test method Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

JP408885A 1985-01-16 1985-01-16 チアゾ−ルカルボン酸アミド誘導体及びその製法 Granted JPS61165376A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP408885A JPS61165376A (ja)	1985-01-16	1985-01-16	チアゾ−ルカルボン酸アミド誘導体及びその製法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP408885A JPS61165376A (ja)	1985-01-16	1985-01-16	チアゾ−ルカルボン酸アミド誘導体及びその製法

Publications (2)

Publication Number	Publication Date
JPS61165376A JPS61165376A (ja)	1986-07-26
JPH0557985B2 true JPH0557985B2 (de)	1993-08-25

Family

ID=11575032

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP408885A Granted JPS61165376A (ja)	1985-01-16	1985-01-16	チアゾ−ルカルボン酸アミド誘導体及びその製法

Country Status (1)

Country	Link
JP (1)	JPS61165376A (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1989012047A1 (fr) *	1988-06-03	1989-12-14	Mitsui Toatsu Chemicals, Incorporated	Procede de preparation de chlorures de l'acide thiazolecarboxylique
JPH0539465U (ja) *	1991-11-06	1993-05-28	積水化学工業株式会社	浴槽洗浄装置

1985
- 1985-01-16 JP JP408885A patent/JPS61165376A/ja active Granted

Also Published As

Publication number	Publication date
JPS61165376A (ja)	1986-07-26

Publication	Publication Date	Title
DE2705446C2 (de)	1989-10-12
JPH0353302B2 (de)	1991-08-14
CA1183540A (en)	1985-03-05	[1-(2-benzoxazolyl)hydrazino]alkyl nitrile derivatives
JPH0561269B2 (de)	1993-09-06
JPS6340430B2 (de)	1988-08-11
US3579529A (en)	1971-05-18	Heterocyclic compounds
EP0592664B1 (de)	2000-07-05	Diphenylthiazolderivate mit antiinflammatorischer aktivität
US4987140A (en)	1991-01-22	Pyridines
JPH0649047A (ja)	1994-02-22	フェニルカルボキサミドイソオキサゾールの新誘導体及びそれらの塩類、それらの製造法及びこの製造法の新規な中間体、それらの薬剤としての用途並びにそれらを含有する製薬組成物
US3337576A (en)	1967-08-22	Arylthioalkyltetrazoles
NO780202L (no)	1978-07-21	Fremgangsmaate for fremstilling av nye derivater av isokinolin
KR940003759B1 (ko)	1994-04-30	4-oh 퀴놀린 카르복실산 유도체의 제조방법
JPS60184077A (ja)	1985-09-19	抗炎症性オキシム前駆薬
JPS6044304B2 (ja)	1985-10-02	フエニルプロピオン酸誘導体の製造方法
MC1135A1 (fr)	1977-11-18	Derives de thiazine
JPS61165376A (ja)	1986-07-26	チアゾ−ルカルボン酸アミド誘導体及びその製法
JPS604809B2 (ja)	1985-02-06	新規な２‐（ｍ‐ベンゾイル）フエニルプロピオン酸エステル誘導体
KR920008822B1 (ko)	1992-10-09	위치 2에 α-히드록실쇄가 치환된 4-히드록시-3-퀴놀린 카르복실산으로 부터 유도된 에스테르의 제조방법
JPS6130669B2 (de)	1986-07-15
GB2311066A (en)	1997-09-17	gem-Difluoro compounds useful for treating pain disorders
JPS6033099B2 (ja)	1985-08-01	新規なナフチルプロピオン酸エステル誘導体
PL174822B1 (pl)	1998-09-30	Sposób wytwarzania kwasu [2-(2,6-dichloroanilino)fenylo] acetoksyoctowego
JPS6256862B2 (de)	1987-11-27
KR820000275B1 (ko)	1982-03-15	티아졸린 유도체의 제조법
KR820000411B1 (ko)	1982-03-29	티아진 유도체의 제조방법