CS203037B2 - Method of producing n-cyan-n'-methyl-n''-/2-/ methyl-5-imidazolyl/methylthio/ethyl/guanidine - Google Patents

Method of producing n-cyan-n'-methyl-n''-/2-/ methyl-5-imidazolyl/methylthio/ethyl/guanidine Download PDF

Info

Publication number: CS203037B2
Authority: CS; Czechoslovakia
Prior art keywords: methyl; guanidine; ethyl; cyano; imidazolyl
Prior art date: 1978-04-26

Application number

CS792885A

Other languages

Czech (cs)

English (en)

Inventor

Branko Jenko

Igor Langof

Joza Habjan

Original Assignee

Lek Tovarna Farmacevtskih

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.)

1978-04-26

Filing date

1979-04-25

Publication date

1981-02-27

1979-04-25 Application filed by Lek Tovarna Farmacevtskih filed Critical Lek Tovarna Farmacevtskih

1981-02-27 Publication of CS203037B2 publication Critical patent/CS203037B2/cs

Links

238000000034 method Methods 0.000 title claims abstract description 21
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 title description 14
-1 methyl-5-imidazolyl Chemical group 0.000 title description 8
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 title description 7
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 title description 7
125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 title description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 3
239000003444 phase transfer catalyst Substances 0.000 claims description 2
150000004714 phosphonium salts Chemical group 0.000 claims description 2
125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
230000002051 biphasic effect Effects 0.000 claims 1
230000003197 catalytic effect Effects 0.000 claims 1
BTDHNWBIBZPIDZ-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine;hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C[NH+](CC=1C=CC=CC=1)CC1=CC=CC=C1 BTDHNWBIBZPIDZ-UHFFFAOYSA-N 0.000 claims 1
RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 claims 1
238000003408 phase transfer catalysis Methods 0.000 abstract description 2
GAIOTNZPXCFNJU-UHFFFAOYSA-N 1-(2-chloroethyl)-3-cyano-2-methylguanidine Chemical compound N#CNC(=NC)NCCCl GAIOTNZPXCFNJU-UHFFFAOYSA-N 0.000 abstract 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
150000001875 compounds Chemical class 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 9
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
239000000047 product Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 4
238000003756 stirring Methods 0.000 description 4
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000011097 chromatography purification Methods 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
238000002955 isolation Methods 0.000 description 2
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
239000012071 phase Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
WBNQBZKYMUQJMI-UHFFFAOYSA-N 1-(2-chloroethyl)-2-cyano-1-methylguanidine Chemical compound ClCCN(C)C(N)=NC#N WBNQBZKYMUQJMI-UHFFFAOYSA-N 0.000 description 1
JEOZNMMOIBLWLV-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethanamine Chemical compound CC=1N=CNC=1CSCCN JEOZNMMOIBLWLV-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
PDWPOXKSTFGRIT-UHFFFAOYSA-N 4-(chloromethyl)-5-methyl-1h-imidazole;hydrochloride Chemical compound Cl.CC=1NC=NC=1CCl PDWPOXKSTFGRIT-UHFFFAOYSA-N 0.000 description 1
ZOHLKTFCEUOOOQ-UHFFFAOYSA-N 4-(methoxymethyl)-5-methyl-1h-imidazole Chemical compound COCC=1N=CNC=1C ZOHLKTFCEUOOOQ-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
102000000543 Histamine Receptors Human genes 0.000 description 1
108010002059 Histamine Receptors Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
102000057297 Pepsin A Human genes 0.000 description 1
108090000284 Pepsin A Proteins 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 1
102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
239000012043 crude product Substances 0.000 description 1
OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 description 1
229940099500 cystamine Drugs 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
LBVZYUZDHIPGLN-UHFFFAOYSA-N imidazol-1-ylmethanethiol Chemical compound SCN1C=CN=C1 LBVZYUZDHIPGLN-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
HRDFVQLHRAQAKQ-UHFFFAOYSA-N methyl n'-ethylcarbamimidothioate Chemical compound CCNC(=N)SC HRDFVQLHRAQAKQ-UHFFFAOYSA-N 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229940111202 pepsin Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000028327 secretion Effects 0.000 description 1
NNENFOSYDBTCBO-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC NNENFOSYDBTCBO-UHFFFAOYSA-M 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/28—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to cyano groups, e.g. cyanoguanidines, dicyandiamides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen 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)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CS792885A 1978-04-26 1979-04-25 Method of producing n-cyan-n'-methyl-n''-/2-/ methyl-5-imidazolyl/methylthio/ethyl/guanidine CS203037B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
YU998/78A YU40332B (en)	1978-04-26	1978-04-26	Process for preparing n-cyano-n'-methyl-n''-((2-((4-methyl-5-imidazolyl)-methylthio)ethyl)-guanidine

Publications (1)

Publication Number	Publication Date
CS203037B2 true CS203037B2 (en)	1981-02-27

Family

ID=25552339

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS792885A CS203037B2 (en)	1978-04-26	1979-04-25	Method of producing n-cyan-n'-methyl-n''-/2-/ methyl-5-imidazolyl/methylthio/ethyl/guanidine

Country Status (19)

Country	Link
US (1)	US4200761A (de)
JP (1)	JPS5440547B1 (de)
AR (1)	AR219794A1 (de)
AT (1)	AT363956B (de)
BE (1)	BE875845A (de)
CA (2)	CA1121363A (de)
CS (1)	CS203037B2 (de)
DD (1)	DD143256A5 (de)
DE (1)	DE2916610C2 (de)
ES (1)	ES479925A1 (de)
FR (1)	FR2424261A1 (de)
GB (2)	GB2041362B (de)
HU (1)	HU180830B (de)
IT (1)	IT1165198B (de)
PL (1)	PL115342B1 (de)
PT (1)	PT69542A (de)
RO (1)	RO78325A (de)
SU (1)	SU862822A3 (de)
YU (1)	YU40332B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6056139B2 (ja) *	1980-11-26	1985-12-09	藤本製薬株式会社	シアノグアニジン誘導体の製造法
CN111848458B (zh) *	2020-08-05	2022-04-26	原平市同利化工有限责任公司	一种制备3-巯基丙酸的过程中提取双氰胺的工艺
CN115784940B (zh) *	2022-12-07	2023-12-05	内蒙古欣皓医药科技有限公司	一种双氰胺晶体的结晶方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1338169A (en) *	1971-03-09	1973-11-21	Smith Kline French Lab	Ureas thioureas and guanidines
GB1397436A (en) *	1972-09-05	1975-06-11	Smith Kline French Lab	Heterocyclic n-cyanoguinidines
US4025527A (en) *	1973-07-13	1977-05-24	Smith Kline & French Laboratories Limited	Certain thiazoles and oxazoles
GB1533380A (en) *	1974-09-02	1978-11-22	Smith Kline French Lab	Process for the preparation of heterocyclic substituted thioureas and h-cyanoguanidines
GB1531231A (en) *	1974-09-02	1978-11-08	Smith Kline French Lab	Process for the production of cyanoguanidine derivatives
US4112234A (en) *	1977-08-22	1978-09-05	Bristol-Myers Company	Imidazolylmethylthioethyl alkynyl guanidines
IL56265A (en) *	1977-12-28	1982-08-31	Om Lab Sa	Process for preparing imidazolyl methylthio guanidine derivatives and a novel intermediate therefor
CH631971A5 (en) *	1977-12-30	1982-09-15	Crc Ricerca Chim	Process for preparing imidazole derivatives

1978
- 1978-04-26 YU YU998/78A patent/YU40332B/xx unknown
1979
- 1979-04-17 AT AT0282779A patent/AT363956B/de not_active IP Right Cessation
- 1979-04-18 US US06/031,239 patent/US4200761A/en not_active Expired - Lifetime
- 1979-04-20 GB GB8000974A patent/GB2041362B/en not_active Expired
- 1979-04-20 GB GB7913760A patent/GB2019842B/en not_active Expired
- 1979-04-24 IT IT67876/79A patent/IT1165198B/it active
- 1979-04-24 CA CA000326202A patent/CA1121363A/en not_active Expired
- 1979-04-24 PT PT69542A patent/PT69542A/pt unknown
- 1979-04-24 RO RO7997352A patent/RO78325A/ro unknown
- 1979-04-24 AR AR276281A patent/AR219794A1/es active
- 1979-04-24 JP JP4983679A patent/JPS5440547B1/ja active Pending
- 1979-04-24 DE DE2916610A patent/DE2916610C2/de not_active Expired
- 1979-04-25 DD DD79212494A patent/DD143256A5/de not_active IP Right Cessation
- 1979-04-25 SU SU792760898A patent/SU862822A3/ru active
- 1979-04-25 BE BE0/194829A patent/BE875845A/xx not_active IP Right Cessation
- 1979-04-25 CS CS792885A patent/CS203037B2/cs unknown
- 1979-04-25 ES ES479925A patent/ES479925A1/es not_active Expired
- 1979-04-26 HU HU79LE840A patent/HU180830B/hu not_active IP Right Cessation
- 1979-04-26 FR FR7910594A patent/FR2424261A1/fr active Granted
- 1979-04-26 PL PL1979215185A patent/PL115342B1/pl unknown
1985
- 1985-09-24 CA CA000491471A patent/CA1209153B/en not_active Expired

Also Published As

Publication number	Publication date
IT1165198B (it)	1987-04-22
HU180830B (en)	1983-04-29
YU99878A (en)	1982-10-31
GB2041362B (en)	1982-08-18
DE2916610A1 (de)	1979-10-31
GB2019842B (en)	1982-10-13
DE2916610C2 (de)	1986-04-03
SU862822A3 (ru)	1981-09-07
US4200761A (en)	1980-04-29
FR2424261A1 (fr)	1979-11-23
IT7967876A0 (it)	1979-04-24
DD143256A5 (de)	1980-08-13
CA1209153B (en)	1986-08-05
AT363956B (de)	1981-09-10
PL115342B1 (en)	1981-03-31
CA1121363A (en)	1982-04-06
ES479925A1 (es)	1979-12-01
PT69542A (en)	1979-05-01
JPS5440547B1 (de)	1979-12-04
AR219794A1 (es)	1980-09-15
BE875845A (fr)	1979-08-16
GB2019842A (en)	1979-11-07
PL215185A1 (de)	1980-01-28
ATA282779A (de)	1981-02-15
RO78325A (ro)	1982-04-12
GB2041362A (en)	1980-09-10
FR2424261B1 (de)	1983-05-13
YU40332B (en)	1985-12-31

Publication	Publication Date	Title
US4013678A (en)	1977-03-22	Process for preparing heterocyclicalkylthioalkyl-n-cyanoguanidines
US4413129A (en)	1983-11-01	Process for preparing the H2 -receptor antagonist cimetidine
RU1802811C (ru)	1993-03-15	Способ получени N-( @ -замещенный алкил)-N @ -(имидазол-4-ил)-гуанидина или его кислых аддитивных солей
US4032559A (en)	1977-06-28	N,2-dicyanoacetimidates
FI79301C (fi)	1989-12-11	Foerfarande foer framstaellning av 4-metyl-5- alkyltiometylimidazoler.
CS203037B2 (en)	1981-02-27	Method of producing n-cyan-n'-methyl-n''-/2-/ methyl-5-imidazolyl/methylthio/ethyl/guanidine
SU950188A3 (ru)	1982-08-07	Способ получени производных 4(5)-меркаптометилимидазолов
CA1164876A (en)	1984-04-03	Process for the preparation of cimetidine
EP0500952B1 (de)	1999-03-03	Verfahren zur herstellung eines stickstoffhaltigen heterozyklus
US4166184A (en)	1979-08-28	2h-imidazole-2-thione derivatives
US4886910A (en)	1989-12-12	Cyanoguanidine derivative and process for preparation thereof
US4365067A (en)	1982-12-21	Method for preparing pharmacologically active cyanoguanidine derivative
JPS59134781A (ja)	1984-08-02	グアニジン誘導体の製法
SU922108A1 (ru)	1982-04-23	Способ получени производных 6-метил-8 @ -гидразинометилэрголина или их солей
EP0276574B1 (de)	1992-03-11	Alpha-acyloxyketon-Derivate
SU471717A3 (ru)	1975-05-25	Способ получени замещенных гуанидина
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