IL27897A - Preparation of pyrazinoalguanides and pyrazinoamidoguanidines - Google Patents

Preparation of pyrazinoalguanides and pyrazinoamidoguanidines

Info

Publication number: IL27897A
Authority: IL; Israel
Prior art keywords: guanidine; lower alkyl; amino; alkyl; diamino
Prior art date: 1966-08-25

Application number

IL2789767A

Other languages

English (en)

Hebrew (he)

Original Assignee

Merck & Co Inc

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.)

1966-08-25

Filing date

1967-05-02

Publication date

1972-02-29

1967-05-02 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1972-02-29 Publication of IL27897A publication Critical patent/IL27897A/en

Links

238000002360 preparation method Methods 0.000 title description 5
WNBSDCKJFDZMHT-UHFFFAOYSA-N n-(diaminomethylidene)pyrazine-2-carboxamide Chemical class NC(N)=NC(=O)C1=CN=CC=N1 WNBSDCKJFDZMHT-UHFFFAOYSA-N 0.000 title description 2
USVSPZQIBAJOIQ-UHFFFAOYSA-N n-(diaminomethylideneamino)pyrazine-2-carboxamide Chemical class NC(=N)NNC(=O)C1=CN=CC=N1 USVSPZQIBAJOIQ-UHFFFAOYSA-N 0.000 title description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 59
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 32
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 28
238000000034 method Methods 0.000 claims description 27
-1 diaminopyrazinamido Chemical group 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
238000005660 chlorination reaction Methods 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
235000019253 formic acid Nutrition 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
RXMUPNVSYKGKMY-UHFFFAOYSA-N 3-amino-6-chloro-n-(diaminomethylidene)-5-(dimethylamino)pyrazine-2-carboxamide Chemical compound CN(C)C1=NC(N)=C(C(=O)N=C(N)N)N=C1Cl RXMUPNVSYKGKMY-UHFFFAOYSA-N 0.000 claims 1
CEEBFRBDJOXNEF-UHFFFAOYSA-N 3-amino-n-(diaminomethylidene)-5-(dimethylamino)pyrazine-2-carboxamide Chemical compound CN(C)C1=CN=C(C(=O)N=C(N)N)C(N)=N1 CEEBFRBDJOXNEF-UHFFFAOYSA-N 0.000 claims 1
238000013019 agitation Methods 0.000 claims 1
125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
239000002904 solvent Substances 0.000 claims 1
229960004198 guanidine Drugs 0.000 description 24
239000000047 product Substances 0.000 description 14
125000004432 carbon atom Chemical group C* 0.000 description 11
239000000376 reactant Substances 0.000 description 8
HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
235000017168 chlorine Nutrition 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
238000003756 stirring Methods 0.000 description 4
125000001309 chloro group Chemical class Cl* 0.000 description 3
239000007858 starting material Substances 0.000 description 3
KEWLVUBYGUZFKX-UHFFFAOYSA-N 2-ethylguanidine Chemical compound CCNC(N)=N KEWLVUBYGUZFKX-UHFFFAOYSA-N 0.000 description 2
DOADNPZTVBOYFT-UHFFFAOYSA-N 3-amino-5-(benzylamino)-6-chloro-n-(diaminomethylidene)pyrazine-2-carboxamide Chemical compound N1=C(N)C(C(=O)NC(=N)N)=NC(Cl)=C1NCC1=CC=CC=C1 DOADNPZTVBOYFT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000002934 diuretic Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
238000000746 purification Methods 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
LINDOXZENKYESA-UHFFFAOYSA-N 1,2-dimethylguanidine Chemical compound CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 1
LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
ABSNGNUGFQIDDO-UHFFFAOYSA-N 2-benzylguanidine Chemical compound NC(N)=NCC1=CC=CC=C1 ABSNGNUGFQIDDO-UHFFFAOYSA-N 0.000 description 1
LSESKQAQXCAXMF-UHFFFAOYSA-N 3,5-diamino-n-(diaminomethylidene)pyrazine-2-carboxamide Chemical compound NC(=N)NC(=O)C1=NC=C(N)N=C1N LSESKQAQXCAXMF-UHFFFAOYSA-N 0.000 description 1
IBLOAFCONPAYDW-UHFFFAOYSA-N 3-(methylamino)pyrazine-2-carboxylic acid Chemical compound CNC1=NC=CN=C1C(O)=O IBLOAFCONPAYDW-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
230000015572 biosynthetic process 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
239000007795 chemical reaction product Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
LMGVITOFKPGSPZ-UHFFFAOYSA-N methyl 3,5-diaminopyrazine-2-carboxylate Chemical compound COC(=O)C1=NC=C(N)N=C1N LMGVITOFKPGSPZ-UHFFFAOYSA-N 0.000 description 1
230000001452 natriuretic effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000001473 noxious effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

IL2789767A 1966-08-25 1967-05-02 Preparation of pyrazinoalguanides and pyrazinoamidoguanidines IL27897A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US57492266A	1966-08-25	1966-08-25

Publications (1)

Publication Number	Publication Date
IL27897A true IL27897A (en)	1972-02-29

Family

ID=24298194

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL2789767A IL27897A (en)	1966-08-25	1967-05-02	Preparation of pyrazinoalguanides and pyrazinoamidoguanidines

Country Status (8)

Country	Link
BE (1)	BE699438A (de)
CH (1)	CH487169A (de)
DE (1)	DE1695421A1 (de)
ES (1)	ES341324A1 (de)
GB (1)	GB1145934A (de)
IL (1)	IL27897A (de)
NL (1)	NL6707570A (de)
SE (1)	SE333146B (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6858615B2 (en)	2002-02-19	2005-02-22	Parion Sciences, Inc.	Phenyl guanidine sodium channel blockers
MX2010006421A (es)	2007-12-10	2010-06-25	Novartis Ag	Compuestos organicos.
AR086745A1 (es)	2011-06-27	2014-01-22	Parion Sciences Inc	3,5-diamino-6-cloro-n-(n-(4-(4-(2-(hexil(2,3,4,5,6-pentahidroxihexil)amino)etoxi)fenil)butil)carbamimidoil)pirazina-2-carboxamida
CA2895512C (en)	2012-12-17	2021-10-19	Parion Sciences, Inc.	Chloro-pyrazine carboxamide derivatives useful for the treatment of diseases favoured by insufficient mucosal hydration
CN108658876A (zh)	2012-12-17	2018-10-16	帕里昂科学公司	3,5-二氨基-6-氯-n-(n-(4-苯基丁基)甲脒基)吡嗪-2-甲酰胺化合物
US9102633B2 (en)	2013-12-13	2015-08-11	Parion Sciences, Inc.	Arylalkyl- and aryloxyalkyl-substituted epithelial sodium channel blocking compounds

1967
- 1967-05-02 IL IL2789767A patent/IL27897A/en unknown
- 1967-05-31 NL NL6707570A patent/NL6707570A/xx unknown
- 1967-06-02 BE BE699438D patent/BE699438A/xx unknown
- 1967-06-02 DE DE19671695421 patent/DE1695421A1/de active Pending
- 1967-06-02 ES ES341324A patent/ES341324A1/es not_active Expired
- 1967-06-07 CH CH804067A patent/CH487169A/de not_active IP Right Cessation
- 1967-06-07 GB GB2621767A patent/GB1145934A/en not_active Expired
- 1967-06-09 SE SE813267A patent/SE333146B/xx unknown

Also Published As

Publication number	Publication date
CH487169A (de)	1970-03-15
DE1695421A1 (de)	1971-04-15
BE699438A (de)	1967-12-04
ES341324A1 (es)	1968-10-01
NL6707570A (de)	1968-02-26
SE333146B (sv)	1971-03-08
GB1145934A (en)	1969-03-19

Publication	Publication Date	Title
US2933502A (en)	1960-04-19	Benzimidazolone derivatives
CH653989A5 (de)	1986-01-31	Cyclobutendion-verbindungen.
IL27897A (en)	1972-02-29	Preparation of pyrazinoalguanides and pyrazinoamidoguanidines
EP0052333B1 (de)	1985-05-08	4-Fluor-5-oxypyrazol-Derivate und Verfahren zu ihrer Herstellung
US2980665A (en)	1961-04-18	Pyrimidines
US3966728A (en)	1976-06-29	Benzoguanamine derivatives
US3244723A (en)	1966-04-05	Certain 4-aminothiazole compounds and their preparation
US3911012A (en)	1975-10-07	Method of preparing 4-chloro-derivatives of phenylformamidine and salts thereof
US3417080A (en)	1968-12-17	Sulfamylanthranilic acid amides and process for preparing them
JPS6236366A (ja)	1987-02-17	２−シアノアミノ−ピリミジン誘導体の製造方法
JPH0217163A (ja)	1990-01-22	ジアミノマレオニトリル及びジアミノアクリロニトリル誘導体の製造方法
IE46671B1 (en)	1983-08-24	Preparation of isobutyramide derivatives
US3128273A (en)	1964-04-07	4-amino-pteridine-7-carboxamides and method of preparation
AT394193B (de)	1992-02-10	Verfahren zur herstellung von neuen 5fluornicotins\|uren oder von deren derivaten und salzen
JPH04120055A (ja)	1992-04-21	アシルアリールスルフェニルセレニド誘導体及びその製法
US3106555A (en)	1963-10-08	Novel amino chlorosulfenyl-s-triazines, their hydrochlorides and process for their production
JPS6354707B2 (de)	1988-10-28
DE2306001C3 (de)	1977-11-03	Pyrimidinderivate, Verfahren zu deren Herstellung und diese enthaltende Geflügelfutterzusammensetzungen
AT234685B (de)	1964-07-10	Verfahren zur Herstellung neuer 3-Phenyl-sydnonimine
CH369457A (de)	1963-05-31	Verfahren zur Herstellung von Pyrimidinen
AT258916B (de)	1967-12-27	Verfahren zur Herstellung von neuen Alkyl-3-amino-5-chlor-6-X-pyrazinoaten
US3225058A (en)	1965-12-21	Substituted n-(4-pyrimidinyl)-6-aminopenicillanic acids
DE2306112A1 (de)	1974-08-15	Thioharnstoffderivate der vitamin-asaeure
JPS60152450A (ja)	1985-08-10	α−アミノケトンの製造方法
EP0495313A1 (de)	1992-07-22	Verfahren zur Herstellung von Acylaminoverbindungen