NO763812L - - Google Patents

Info

Publication number: NO763812L
Authority: NO; Norway
Prior art keywords: formula; het; compound; methyl; reacted
Prior art date: 1975-11-12

Application number

NO763812A

Other languages

English (en)

Norwegian (no)

Inventor

G J Durant

C R Ganellin

Original Assignee

Smith Kline French Lab

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.)

1975-11-12

Filing date

1976-11-09

Publication date

1977-05-13

1976-11-09 Application filed by Smith Kline French Lab filed Critical Smith Kline French Lab

1977-05-13 Publication of NO763812L publication Critical patent/NO763812L/no

Links

150000001875 compounds Chemical class 0.000 claims description 31
150000001412 amines Chemical class 0.000 claims description 13
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
239000005864 Sulphur Substances 0.000 claims description 4
150000001350 alkyl halides Chemical class 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Chemical group 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
-1 4-imidazolyl Chemical group 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 5
239000003485 histamine H2 receptor antagonist Substances 0.000 description 5
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
239000003456 ion exchange resin Substances 0.000 description 4
229920003303 ion-exchange polymer Polymers 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
XLPKHGNAYJQMRC-UHFFFAOYSA-N 1-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]-2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]propyl]guanidine;trihydrochloride Chemical compound Cl.Cl.Cl.N1C=NC(C)=C1CSC(C)CNC(=N)NCCSCC=1NC=NC=1C XLPKHGNAYJQMRC-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
102000003710 Histamine H2 Receptors Human genes 0.000 description 2
108090000050 Histamine H2 Receptors Proteins 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
229960001340 histamine Drugs 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
UBHDUFNPQJWPRQ-UHFFFAOYSA-N (5-methyl-1h-imidazol-3-ium-4-yl)methanol;chloride Chemical compound Cl.CC=1NC=NC=1CO UBHDUFNPQJWPRQ-UHFFFAOYSA-N 0.000 description 1
KCOYHFNCTWXETP-UHFFFAOYSA-N (carbamothioylamino)thiourea Chemical class NC(=S)NNC(N)=S KCOYHFNCTWXETP-UHFFFAOYSA-N 0.000 description 1
FNNQKDIXJANKOJ-UHFFFAOYSA-N 1,2-bis[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]propyl]guanidine Chemical compound N1C=NC(C)=C1CSC(C)CNC(=N)NCC(C)SCC=1NC=NC=1C FNNQKDIXJANKOJ-UHFFFAOYSA-N 0.000 description 1
CHCIGVSHMUCKSA-UHFFFAOYSA-N 1,2-bis[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]propyl]guanidine;trihydrochloride Chemical compound Cl.Cl.Cl.N1C=NC(C)=C1CSC(C)CNC(=N)NCC(C)SCC=1NC=NC=1C CHCIGVSHMUCKSA-UHFFFAOYSA-N 0.000 description 1
XSAXLPYZTXJUDU-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethylthiourea Chemical compound CC=1N=CNC=1CSCCNC(N)=S XSAXLPYZTXJUDU-UHFFFAOYSA-N 0.000 description 1
HYSZRUJKUKKFRL-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]propan-1-amine Chemical compound NCC(C)SCC=1N=CNC=1C HYSZRUJKUKKFRL-UHFFFAOYSA-N 0.000 description 1
BKYGRLQMOFGPPF-UHFFFAOYSA-N 2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]propan-1-amine;dihydrobromide Chemical compound Br.Br.NCC(C)SCC=1N=CNC=1C BKYGRLQMOFGPPF-UHFFFAOYSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
HCZBCEYVAPRCDV-UHFFFAOYSA-N 2-sulfanylpropylazanium;chloride Chemical compound Cl.CC(S)CN HCZBCEYVAPRCDV-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
OVFUUSPKWADLNJ-UHFFFAOYSA-N 5-methyl-4-nitro-2-(4-nitrophenyl)-4h-pyrazol-3-one Chemical compound O=C1C([N+]([O-])=O)C(C)=NN1C1=CC=C([N+]([O-])=O)C=C1 OVFUUSPKWADLNJ-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 1
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
NPPYCTSQYCMZIB-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]azanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CSC(N)=[NH+]CCSCC=1N=CNC=1C.CSC(N)=[NH+]CCSCC=1N=CNC=1C NPPYCTSQYCMZIB-UHFFFAOYSA-N 0.000 description 1
150000001351 alkyl iodides Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 1
UHNOAGDNODCLKN-UHFFFAOYSA-N bromine;pyridine Chemical group [Br].C1=CC=NC=C1 UHNOAGDNODCLKN-UHFFFAOYSA-N 0.000 description 1
RIMGDBZXWSGBQN-UHFFFAOYSA-N burimamide Chemical compound CNC(=S)NCCCCC1=CN=C[N]1 RIMGDBZXWSGBQN-UHFFFAOYSA-N 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
238000010828 elution Methods 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
210000004211 gastric acid Anatomy 0.000 description 1
230000027119 gastric acid secretion Effects 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
150000002541 isothioureas Chemical class 0.000 description 1
YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 1
229960000582 mepyramine Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
OPGQGYQPVOWUOO-UHFFFAOYSA-N methyl n'-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]carbamimidothioate;hydroiodide Chemical compound I.CSC(=N)NCCSCC=1N=CNC=1C OPGQGYQPVOWUOO-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
MCWKMMXOIRBRQD-UHFFFAOYSA-N n-(dichloromethylidene)benzamide Chemical compound ClC(Cl)=NC(=O)C1=CC=CC=C1 MCWKMMXOIRBRQD-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO763812A 1975-11-12 1976-11-09 NO763812L (xx)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB46732/75A GB1573611A (en)	1975-11-12	1975-11-12	Heterocyclic thioalkyl-amines-guanidines and -thioureas

Publications (1)

Publication Number	Publication Date
NO763812L true NO763812L (xx)	1977-05-13

Family

ID=10442384

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO763812A NO763812L (xx)	1975-11-12	1976-11-09

Country Status (22)

Country	Link
JP (1)	JPS5262274A (xx)
AT (1)	AT350583B (xx)
AU (1)	AU508143B2 (xx)
BE (1)	BE848108A (xx)
CA (1)	CA1070316A (xx)
DE (1)	DE2649546A1 (xx)
DK (1)	DK503176A (xx)
ES (1)	ES453263A1 (xx)
FI (1)	FI763209A (xx)
FR (1)	FR2331342A1 (xx)
GB (1)	GB1573611A (xx)
HU (1)	HU175667B (xx)
IE (1)	IE44103B1 (xx)
IL (1)	IL50748A0 (xx)
LU (1)	LU76162A1 (xx)
NL (1)	NL7611590A (xx)
NO (1)	NO763812L (xx)
NZ (1)	NZ182309A (xx)
PT (1)	PT65759B (xx)
SE (1)	SE7611405L (xx)
SU (1)	SU634668A3 (xx)
ZA (1)	ZA766201B (xx)

1975
- 1975-11-12 GB GB46732/75A patent/GB1573611A/en not_active Expired
1976
- 1976-10-12 NZ NZ182309A patent/NZ182309A/xx unknown
- 1976-10-14 SE SE7611405A patent/SE7611405L/xx unknown
- 1976-10-18 ZA ZA766201A patent/ZA766201B/xx unknown
- 1976-10-19 CA CA263,718A patent/CA1070316A/en not_active Expired
- 1976-10-20 NL NL7611590A patent/NL7611590A/xx not_active Application Discontinuation
- 1976-10-21 AU AU18900/76A patent/AU508143B2/en not_active Expired
- 1976-10-22 IL IL50748A patent/IL50748A0/xx unknown
- 1976-10-26 PT PT65759A patent/PT65759B/pt unknown
- 1976-10-26 IE IE2363/76A patent/IE44103B1/en unknown
- 1976-10-29 DE DE19762649546 patent/DE2649546A1/de not_active Withdrawn
- 1976-11-04 AT AT819776A patent/AT350583B/de active
- 1976-11-08 BE BE172167A patent/BE848108A/xx not_active IP Right Cessation
- 1976-11-08 DK DK503176A patent/DK503176A/da not_active Application Discontinuation
- 1976-11-09 FI FI763209A patent/FI763209A/fi not_active Application Discontinuation
- 1976-11-09 NO NO763812A patent/NO763812L/no unknown
- 1976-11-10 FR FR7633962A patent/FR2331342A1/fr active Granted
- 1976-11-10 JP JP51135826A patent/JPS5262274A/ja active Pending
- 1976-11-10 LU LU76162A patent/LU76162A1/xx unknown
- 1976-11-11 HU HU76SI1548A patent/HU175667B/hu unknown
- 1976-11-11 SU SU762418884A patent/SU634668A3/ru active
- 1976-11-12 ES ES453263A patent/ES453263A1/es not_active Expired

Also Published As

Publication number	Publication date
IE44103B1 (en)	1981-08-12
DK503176A (da)	1977-05-13
PT65759B (en)	1978-04-27
NZ182309A (en)	1978-07-10
HU175667B (hu)	1980-09-28
AT350583B (de)	1979-06-11
AU508143B2 (en)	1980-03-13
ES453263A1 (es)	1978-01-16
CA1070316A (en)	1980-01-22
FR2331342A1 (fr)	1977-06-10
DE2649546A1 (de)	1977-05-26
BE848108A (fr)	1977-05-09
AU1890076A (en)	1978-04-27
IE44103L (en)	1977-05-12
SU634668A3 (ru)	1978-11-25
JPS5262274A (en)	1977-05-23
FR2331342B1 (xx)	1980-03-07
PT65759A (en)	1976-11-01
NL7611590A (nl)	1977-05-16
ATA819776A (de)	1978-11-15
SE7611405L (sv)	1977-05-13
ZA766201B (en)	1977-09-28
GB1573611A (en)	1980-08-28
LU76162A1 (xx)	1977-05-18
IL50748A0 (en)	1976-12-31
FI763209A (xx)	1977-05-13

Publication	Publication Date	Title
US4013678A (en)	1977-03-22	Process for preparing heterocyclicalkylthioalkyl-n-cyanoguanidines
EP0128736B1 (en)	1987-02-25	Novel 2-guanidinothiazoline compounds, their preparation, and their use as intermediates
SE416049B (sv)	1980-11-24	Forfarande for framstellning av 1,1-diaminoctylenderivat, som kan anvendas for hemning av vissa histaminverkningar
NO143942B (no)	1981-02-02	Analogifremgangsmaate for fremstilling av farmakologisk aktive heterocyklisk substituerte guanidiner
US4301165A (en)	1981-11-17	Pharmacologically active compounds
US4049671A (en)	1977-09-20	Process for preparing N-cyanoguanidines
CS199255B2 (en)	1980-07-31	Method of preparing pharmacologically active compounds
US4070472A (en)	1978-01-24	Guanidino, thioureido, isothioureido and nitrovinylamino derivatives of pyridine
DE2604056A1 (de)	1976-08-05	Thiocarbaminsaeure-derivate
US4093621A (en)	1978-06-06	Process for preparing heterocyclicalkylthioalkyl-N-cyanoguanidines and thioureas
US4285952A (en)	1981-08-25	Pyridyl, thiazolyl and isothiazolyl alkyl bisamidines
NO762659L (xx)	1977-02-01
FI79301B (fi)	1989-08-31	Foerfarande foer framstaellning av 4-metyl-5- alkyltiometylimidazoler.
HU176611B (en)	1981-03-28	Process for producing substituted amidino derivatives
NO763812L (xx)	1977-05-13
EP0054409B1 (en)	1985-09-18	Preparation of thiazolidine derivatives
US4728655A (en)	1988-03-01	Sulfonamidines, process for the production thereof and pharmaceutical compositions containing the same
CA1263120A (en)	1989-11-21	Process for the preparation of n-sulfamyl-3-(2- guanidino-thiazol-4-yl-methylthio)-propionamidine
US4166856A (en)	1979-09-04	Thiazole and isothiazole derivative as blockers of histamine H2 -receptors
CS207750B2 (en)	1981-08-31	Method of making the n'-cyano-n'-alcyl-n-2-/5-methyl-1h-imidazol-4-yl/methyl thicethyl guanidines
US4137319A (en)	1979-01-30	Guanidino, thioureido, isothioureido and nitrovinylamino derivatives of pyridine
EP0215639B1 (en)	1990-08-29	Propionamidine derivatives
JPS5936674A (ja)	1984-02-28	Ｎ−置換グアニジノチアゾ−ル誘導体およびその製造法
US4151289A (en)	1979-04-24	Nitromethylene amidino derivatives containing imidazole groups
US4171325A (en)	1979-10-16	Chemical process