JPS6047259B2 - グアニジン化合物の製法 - Google Patents

グアニジン化合物の製法

Info

Publication number: JPS6047259B2
Authority: JP; Japan
Prior art keywords: formula; methyl; cyanamide; ethyl; methylthio
Prior art date: 1974-09-02
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

JP50106458A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5154561A (en

Inventor

ジヨンデユラントグラハム

ロビンガネリンチヤ−ロン

レイモンドホワイトジヨ−ジ

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.)

GSK PLC

Original Assignee

GlaxoSmithKline PLC

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.)

1974-09-02

Filing date

1975-09-01

Publication date

1985-10-21

1975-09-01 Application filed by GlaxoSmithKline PLC filed Critical GlaxoSmithKline PLC

1976-05-13 Publication of JPS5154561A publication Critical patent/JPS5154561A/ja

1985-10-21 Publication of JPS6047259B2 publication Critical patent/JPS6047259B2/ja

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 5
150000002357 guanidines Chemical class 0.000 title description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 17
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 6
ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
-1 guanidine compound Chemical class 0.000 claims description 4
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
150000001875 compounds Chemical class 0.000 description 7
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
238000000034 method Methods 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
150000001718 carbodiimides Chemical class 0.000 description 4
239000000203 mixture Substances 0.000 description 4
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
150000001661 cadmium Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
ATMYQJHPCACNAV-UHFFFAOYSA-N ethyl acetate;propan-1-ol Chemical compound CCCO.CCOC(C)=O ATMYQJHPCACNAV-UHFFFAOYSA-N 0.000 description 1
ANFZRGMDGDYNGA-UHFFFAOYSA-N ethyl acetate;propan-2-ol Chemical compound CC(C)O.CCOC(C)=O ANFZRGMDGDYNGA-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000027119 gastric acid secretion Effects 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 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
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)

JP50106458A 1974-09-02 1975-09-01 グアニジン化合物の製法 Expired JPS6047259B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB3822374A GB1531221A (en)	1974-09-02	1974-09-02	Process for preparing guanidine derivatives
GB38223/74		1974-09-02

Publications (2)

Publication Number	Publication Date
JPS5154561A JPS5154561A (en)	1976-05-13
JPS6047259B2 true JPS6047259B2 (ja)	1985-10-21

Family

ID=10402061

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
JP50106458A Expired JPS6047259B2 (ja)	1974-09-02	1975-09-01	グアニジン化合物の製法
JP60078249A Pending JPS60231660A (ja)	1974-09-02	1985-04-11	グアニジン化合物の製法
JP60078248A Pending JPS60231659A (ja)	1974-09-02	1985-04-11	イソチオウレア化合物の製法

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
JP60078249A Pending JPS60231660A (ja)	1974-09-02	1985-04-11	グアニジン化合物の製法
JP60078248A Pending JPS60231659A (ja)	1974-09-02	1985-04-11	イソチオウレア化合物の製法

Country Status (3)

Country	Link
JP (3)	JPS6047259B2 (fr)
BE (1)	BE832665A (fr)
GB (1)	GB1531221A (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DD129906A5 (de) *	1976-09-21	1978-02-15	Smith Kline French Lab	Verfahren zur herstellung einer kristallographisch reinen polymorphen form von cimetidin(cimetidin a)
US4165378A (en)	1977-04-20	1979-08-21	Ici Americas Inc.	Guanidine derivatives of imidazoles and thiazoles
NZ186965A (en)	1977-04-20	1980-02-21	Ici Ltd	Guanidino derivatives and pharmaceutical compositions
CA1110251A (fr) *	1977-06-03	1981-10-06	Ronnie R. Crenshaw	Agents de blocage du recepteur de h.sub.2 des h- cyano-n'- 2-¬(4-methyl-5- imidazolyl)methylthio\|ethyl -n"-alkynylguanidines
YU40716B (en) *	1978-07-19	1986-04-30	Pliva Pharm & Chem Works	Process for obtaining n-cyano-n'-methyl-n'-û2-\|5-metylimidazole4-yl)-methyl¨-thioethylù guanidine
US4309435A (en) *	1978-10-16	1982-01-05	Imperial Chemical Industries Ltd.	Antisecretory guanidine derivatives and pharmaceutical compositions containing them
EP0014057B1 (fr)	1979-01-18	1985-01-02	Imperial Chemical Industries Plc	Dérivés de la guanidine, procédés pour leur préparation et compositions pharmaceutiques les contenant
US4242351A (en) *	1979-05-07	1980-12-30	Imperial Chemical Industries Limited	Antisecretory oxadiazoles and pharmaceutical compositions containing them
US4220654A (en) *	1979-06-04	1980-09-02	Merck & Co., Inc.	Cyclic imidazole cyanoguanidines
FR2686084B1 (fr) *	1992-01-10	1995-12-22	Bioprojet Soc Civ	Nouveaux derives de l'imidazole, leur preparation et leurs applications therapeutiques.
USRE37303E1 (en) *	1992-01-10	2001-07-31	Institut National Del La Sante Et De La Recherche Medicale	Imidazole compounds and their therapeutic applications
CN102633701B (zh) *	2012-04-05	2014-07-23	山东京博控股股份有限公司	一种s-甲基异硫脲盐的合成方法
JP7437932B2 (ja) *	2019-12-27	2024-02-26	三井化学株式会社	廃水処理方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ200641A (en) *	1981-07-13	1985-12-13	Merck & Co Inc	Pharmaceutical compositions containing(+)and(-)enantiomers of indacrinone

1974
- 1974-09-02 GB GB3822374A patent/GB1531221A/en not_active Expired
1975
- 1975-08-22 BE BE159395A patent/BE832665A/fr not_active IP Right Cessation
- 1975-09-01 JP JP50106458A patent/JPS6047259B2/ja not_active Expired
1985
- 1985-04-11 JP JP60078249A patent/JPS60231660A/ja active Pending
- 1985-04-11 JP JP60078248A patent/JPS60231659A/ja active Pending

Also Published As

Publication number	Publication date
BE832665A (fr)	1976-02-23
JPS60231659A (ja)	1985-11-18
JPS5154561A (en)	1976-05-13
JPS60231660A (ja)	1985-11-18
GB1531221A (en)	1978-11-08

Publication	Publication Date	Title
JPS5940829B2 (ja)	1984-10-03	メルカプトエチル置換グアニジンの製法
JPS60231660A (ja)	1985-11-18	グアニジン化合物の製法
JPS5946222B2 (ja)	1984-11-10	グアニジン化合物の製法
US3391189A (en)	1968-07-02	Nu-allyl-guanidines and salts thereof
LeBlond et al.	1974	Fluoro [imidobis (sulphuryl fluoride)] xenon. An example of a xenon–nitrogen bond
JPS6343390B2 (fr)	1988-08-30
JPS632264B2 (fr)	1988-01-18
US2748122A (en)	1956-05-29	2-anilino-4, 6-dimethylpyrimidines
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
CS207750B2 (en)	1981-08-31	Method of making the n'-cyano-n'-alcyl-n-2-/5-methyl-1h-imidazol-4-yl/methyl thicethyl guanidines
GB1578219A (en)	1980-11-05	Isothioureas
CA1108142A (fr)	1981-09-01	Procede d'obtention de 2-isopropylamino-pyrimidine
JP3161690B2 (ja)	2001-04-25	２−メルカプトイミダゾール縮合環化合物の製造法
JPS5910345B2 (ja)	1984-03-08	チオウレア化合物の製法
JPS63201165A (ja)	1988-08-19	シアノグアニジン誘導体及びその製造法
JPS62138479A (ja)	1987-06-22	Ｎ−シアノ−ｎ′−メチル−ｎ″−〔２−〔〔（５−メチル−１ｈ−イミダゾ−ル−４−イル）メチル〕チオ〕エチル〕グアニジンの製造法
JPH0113476B2 (fr)	1989-03-06
JPS6030310B2 (ja)	1985-07-16	イミダゾールの製法
SU923370A3 (ru)	1982-04-23	Способ получени 3,4-диметокси-6-/4-(2-фуроил)-1-пиперазинилтиокарбамидо/-бензонитрила
JPS5910346B2 (ja)	1984-03-08	チオウレアの製法
KR820002364B1 (ko)	1982-12-27	2-이소프로필아미노 피리미딘의 제조방법
JPS6327339B2 (fr)	1988-06-02
JPS5920676B2 (ja)	1984-05-15	新規なピリミド〔４，５−ｄ〕ピリミジン誘導体の製造法
US4703121A (en)	1987-10-27	Process for the preparation of 5-fluorocytosine
US2676175A (en)	1954-04-20	Process for manufacturing thiamine