JPH0359905B2 - - Google Patents

Info

Publication number: JPH0359905B2
Authority: JP; Japan
Prior art keywords: general formula; formula; mentioned meaning; represented; acid
Prior art date: 1982-11-26
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

JP20602282A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5998076A (ja

Inventor

Masatoshi Ban

Kenji Hamase

Tomoo Suzuki

Hiromoto Kimura

Tadashi Terada

Masatsune Kurono

Hiroyoshi Hidaka

Nobuyuki Ito

Shuji Ando

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.)

Sanwa Kagaku Kenkyusho Co Ltd

Original Assignee

Sanwa Kagaku Kenkyusho 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.)

1982-11-26

Filing date

1982-11-26

Publication date

1991-09-12

1982-11-26 Application filed by Sanwa Kagaku Kenkyusho Co Ltd filed Critical Sanwa Kagaku Kenkyusho Co Ltd

1982-11-26 Priority to JP20602282A priority Critical patent/JPS5998076A/ja

1984-06-06 Publication of JPS5998076A publication Critical patent/JPS5998076A/ja

1991-09-12 Publication of JPH0359905B2 publication Critical patent/JPH0359905B2/ja

Status Granted legal-status Critical Current

Links

239000002253 acid Substances 0.000 claims description 19
-1 β-nicotinoylaminoethyl group Chemical group 0.000 claims description 15
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 11
235000010288 sodium nitrite Nutrition 0.000 claims description 6
229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
239000011707 mineral Substances 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 3
125000005219 aminonitrile group Chemical group 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 2
150000002148 esters Chemical class 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000000034 method Methods 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
238000000921 elemental analysis Methods 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
150000002825 nitriles Chemical class 0.000 description 4
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
GSKDBLIBBOYOFU-UHFFFAOYSA-N oxadiazol-5-amine Chemical class NC1=CN=NO1 GSKDBLIBBOYOFU-UHFFFAOYSA-N 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000003480 eluent Substances 0.000 description 2
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
150000004682 monohydrates Chemical class 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
BKILPAYYYRJTPP-UHFFFAOYSA-M sodium;formaldehyde;hydrogen sulfite;hydrate Chemical compound O.[Na+].O=C.OS([O-])=O BKILPAYYYRJTPP-UHFFFAOYSA-M 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000004004 anti-anginal agent Substances 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
229940124345 antianginal agent Drugs 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
RTIXFTKDETURTM-UHFFFAOYSA-N n-(2-aminoethyl)pyridine-3-carboxamide Chemical compound NCCNC(=O)C1=CC=CN=C1 RTIXFTKDETURTM-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
230000000304 vasodilatating effect Effects 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)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP20602282A 1982-11-26 1982-11-26 新規なシドノンイミン化合物及びその製法 Granted JPS5998076A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP20602282A JPS5998076A (ja)	1982-11-26	1982-11-26	新規なシドノンイミン化合物及びその製法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP20602282A JPS5998076A (ja)	1982-11-26	1982-11-26	新規なシドノンイミン化合物及びその製法

Publications (2)

Publication Number	Publication Date
JPS5998076A JPS5998076A (ja)	1984-06-06
JPH0359905B2 true JPH0359905B2 (fr)	1991-09-12

Family

ID=16516599

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP20602282A Granted JPS5998076A (ja)	1982-11-26	1982-11-26	新規なシドノンイミン化合物及びその製法

Country Status (1)

Country	Link
JP (1)	JPS5998076A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3820210A1 (de) *	1988-06-14	1989-12-21	Cassella Ag	Substituierte 3-aminosydnonimine, verfahren zu ihrer herstellung und ihre verwendung

1982
- 1982-11-26 JP JP20602282A patent/JPS5998076A/ja active Granted

Also Published As

Publication number	Publication date
JPS5998076A (ja)	1984-06-06

Publication	Publication Date	Title
US10730876B2 (en)	2020-08-04	Synthesis of a compound that modulates kinases
JP3179515B2 (ja)	2001-06-25	２−クロロチアゾール類の製造方法
JPS626718B2 (fr)	1987-02-13
NO328627B1 (no)	2010-04-12	Fremgangsmate for fremstillingen av iopamidol og de nye intermediater deri
KR920002295B1 (ko)	1992-03-21	프롤리디논 유도체의 제조방법
JP3712619B2 (ja)	2005-11-02	カテコールヒドラゾン誘導体、製造方法及びこれを含む医薬組成物
JPH0359905B2 (fr)	1991-09-12
JP2771257B2 (ja)	1998-07-02	イミダゾール誘導体の製法
JP3759411B2 (ja)	2006-03-22	４−シアノ−３−ヒドロキシブタノイルヒドラジン類、その誘導体およびその製造方法
JP2767295B2 (ja)	1998-06-18	インドール―３―カルボニトリル化合物の製造方法
WO2001044165A1 (fr)	2001-06-21	Procedes de production de derives de (aminomethyl)trifluorocarbinol
SU1531854A3 (ru)	1989-12-23	Способ получени ранитидина или его гидрохлорида
JP4425366B2 (ja)	2010-03-03	Ｎ−ベンジル−３−ヒドロキシアゼチジンの製造法
KR100361824B1 (ko)	2003-01-29	2-아미노티아졸카르복사미드유도체의제조방법
SU471711A3 (ru)	1975-05-25	Способ получени производных -аминоакриловой кислоты
JP2001261647A5 (fr)	2007-06-21
JP2671401B2 (ja)	1997-10-29	α‐アミノチオアセトアミド誘導体およびその製造法
JP3216673B2 (ja)	2001-10-09	３−ヒドロキシイソオキサゾールの製造法
JP3127505B2 (ja)	2001-01-29	ピラゾロピリジン誘導体の製造法
KR800001549B1 (ko)	1980-12-27	티아졸릴초산 화합물의 제조 방법
JP2563864B2 (ja)	1996-12-18	２−（３，４−ジメトキシスチリル）−３，１−ベンゾオキサジン−４−オンの製造方法
JPS6054342A (ja)	1985-03-28	バニリルアミン塩酸塩の製造方法
JPS6317869A (ja)	1988-01-25	２−低級アルキル−４−アミノ−５−ホルミルピリミジンの製造法
JPH01186874A (ja)	1989-07-26	３−メルカプト−５−アミノ−（１ｈ）−１，２，４−トリアゾールの製造法
JPH06157497A (ja)	1994-06-03	メルカプトイミダゾール誘導体の製造方法