JPS625915B2 - - Google Patents

Info

Publication number: JPS625915B2
Authority: JP; Japan
Prior art keywords: group; compound; acid; lower alkyl; substituent
Prior art date: 1977-07-08
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

JP52080960A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5416497A (en

Inventor

Giichi Genda

Nobuo Tomita

Masaru Ito

Saburo Kano

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.)

Nippon Soda Co Ltd

Original Assignee

Nippon 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.)

1977-07-08

Filing date

1977-07-08

Publication date

1987-02-07

1977-07-08 Application filed by Nippon Soda Co Ltd filed Critical Nippon Soda Co Ltd

1977-07-08 Priority to JP8096077A priority Critical patent/JPS5416497A/ja

1979-02-07 Publication of JPS5416497A publication Critical patent/JPS5416497A/ja

1987-02-07 Publication of JPS625915B2 publication Critical patent/JPS625915B2/ja

Status Granted legal-status Critical Current

Links

-1 4b]pyrazine compound Chemical class 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 24
239000002253 acid Substances 0.000 claims description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
229910052783 alkali metal Inorganic materials 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
150000004703 alkoxides Chemical class 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000001072 heteroaryl group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
238000006386 neutralization reaction Methods 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims 1
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
235000019441 ethanol Nutrition 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 8
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
239000011734 sodium Substances 0.000 description 4
DPZSNGJNFHWQDC-ARJAWSKDSA-N (z)-2,3-diaminobut-2-enedinitrile Chemical compound N#CC(/N)=C(/N)C#N DPZSNGJNFHWQDC-ARJAWSKDSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000000034 method Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
230000003472 neutralizing effect Effects 0.000 description 3
239000000049 pigment Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
238000005406 washing Methods 0.000 description 3
USDIRSJFHPHMAS-UHFFFAOYSA-N ClC1=NC=C(C=2C1=NC=CN=2)F Chemical compound ClC1=NC=C(C=2C1=NC=CN=2)F USDIRSJFHPHMAS-UHFFFAOYSA-N 0.000 description 2
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 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
IYXMNTLBLQNMLM-UHFFFAOYSA-N benzene-1,4-diamine;hydron;dichloride Chemical compound Cl.Cl.NC1=CC=C(N)C=C1 IYXMNTLBLQNMLM-UHFFFAOYSA-N 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000007789 gas Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
150000003949 imides Chemical group 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
238000004949 mass spectrometry Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
239000011684 sodium molybdate Substances 0.000 description 2
235000015393 sodium molybdate Nutrition 0.000 description 2
TVXXNOYZHKPKGW-UHFFFAOYSA-N sodium molybdate (anhydrous) Chemical compound [Na+].[Na+].[O-][Mo]([O-])(=O)=O TVXXNOYZHKPKGW-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
STQPCKPKAIRSEL-UHFFFAOYSA-N 2-cyanobenzamide Chemical compound NC(=O)C1=CC=CC=C1C#N STQPCKPKAIRSEL-UHFFFAOYSA-N 0.000 description 1
MMBYJYAFFGKUDC-UHFFFAOYSA-N 3-aminoisoindol-1-one Chemical compound C1=CC=C2C(N)=NC(=O)C2=C1 MMBYJYAFFGKUDC-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
VPRRXMCIOHZBCX-UHFFFAOYSA-N 5,6-dimethylpyrazine-2,3-dicarbonitrile Chemical compound CC1=NC(C#N)=C(C#N)N=C1C VPRRXMCIOHZBCX-UHFFFAOYSA-N 0.000 description 1
RHYUBLSWHDYKAO-UHFFFAOYSA-N 5-methylpyrazine-2,3-dicarbonitrile Chemical compound CC1=CN=C(C#N)C(C#N)=N1 RHYUBLSWHDYKAO-UHFFFAOYSA-N 0.000 description 1
125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
101150095408 CNMD gene Proteins 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000003172 aldehyde group Chemical group 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000006298 dechlorination reaction Methods 0.000 description 1
SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003216 pyrazines Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000010998 test method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229910000314 transition metal oxide Inorganic materials 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1

Landscapes

Nitrogen Condensed Heterocyclic Rings (AREA)

JP8096077A 1977-07-08 1977-07-08 Aminooxopyrrolopyrazine compounds and their preparation Granted JPS5416497A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP8096077A JPS5416497A (en)	1977-07-08	1977-07-08	Aminooxopyrrolopyrazine compounds and their preparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP8096077A JPS5416497A (en)	1977-07-08	1977-07-08	Aminooxopyrrolopyrazine compounds and their preparation

Publications (2)

Publication Number	Publication Date
JPS5416497A JPS5416497A (en)	1979-02-07
JPS625915B2 true JPS625915B2 (it)	1987-02-07

Family

ID=13733070

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP8096077A Granted JPS5416497A (en)	1977-07-08	1977-07-08	Aminooxopyrrolopyrazine compounds and their preparation

Country Status (1)

Country	Link
JP (1)	JPS5416497A (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2003284981B2 (en) *	2002-10-30	2009-05-28	Merck Sharp & Dohme Corp.	Inhibitors of Akt activity

1977
- 1977-07-08 JP JP8096077A patent/JPS5416497A/ja active Granted

Also Published As

Publication number	Publication date
JPS5416497A (en)	1979-02-07

Publication	Publication Date	Title
JPH03115265A (ja)	1991-05-16	ピラゾール及びその誘導体の製造方法
US5498711A (en)	1996-03-12	Synthesis of 4,10-dinitro-2,6,8,12-tetraoxa-4,10-diazatetracyclo[5.5.0.05,903,11]dodecane
JPS625915B2 (it)	1987-02-07
JPS5949221B2 (ja)	1984-12-01	３−アシルアミノ−４−ホモイソツイスタンの製造法
US2813868A (en)	1957-11-19	Heterocyclic quinones
US3410852A (en)	1968-11-12	Process for preparing 3, 4-dihydro-2, 4-dioxo-2h-pyrido[2, 3-e][1, 3]oxazine
FR2604707A1 (fr)	1988-04-08	Procede de preparation d'un compose therapeutique actif
JPS5928546B2 (ja)	1984-07-13	ヒドラゾジカルボンアミドの製造法
JPH0573738B2 (it)	1993-10-15
US3052687A (en)	1962-09-04	Process for the production of
NO149027B (no)	1983-10-24	Innretning til aa paafoere et belegg paa en neddykket overflate
JPS5916878A (ja)	1984-01-28	２，４−ジヒドロキシ−３−アセチルキノリン類の製造方法
JP4351316B2 (ja)	2009-10-28	ベンゾオキサゾール誘導体およびその製造法
SU487878A1 (ru)	1975-10-15	Способ получени -дифенил- -пикрилгидразина
JPS59176234A (ja)	1984-10-05	ｐ‐ニトロフエニル３−ブロモ−２，２−ジエトキシ−プロピオネート
JP2937387B2 (ja)	1999-08-23	５―置換２―アミノ―３―シアノピラジン類の製法
US3349086A (en)	1967-10-24	Process for the preparation of asymmetric amino triazine derivatives
SU280482A1 (ru)		Способ получения 7-галоген- или 7,7-дигалоген- пиразино
JP2565372B2 (ja)	1996-12-18	チオール化合物の製造方法
JPS638942B2 (it)	1988-02-25
JP2710636B2 (ja)	1998-02-10	ピラゾロ〔５．１−ｂ〕キナゾロンの製法
JPS61268688A (ja)	1986-11-28	２，６−ジアミノベンゾ−〔１，２−ｄ：４，５−ｄ′〕−ビスチアゾ−ルの製造法
US3814763A (en)	1974-06-04	Process for making orotic acid
SU1188169A1 (ru)	1985-10-30	Способ получени 2-(2-аминотиазолил-5)-3,5,6-трихлор-1,4-бензохинонов
US1660178A (en)	1928-02-21	Albert rothmann