CY1229A - Guanidine derivatives - Google Patents

Guanidine derivatives Download PDF

Info

Publication number: CY1229A
Authority: CY; Cyprus
Prior art keywords: cyano; guanidine; compound; methyl; butyn
Prior art date: 1977-06-03

Application number

CY1229A

Other languages

English (en)

Original Assignee

Bristol Myers Co

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.)

1977-06-03

Filing date

1978-05-26

Publication date

1984-06-29

1977-11-07 Priority claimed from US05/848,959 external-priority patent/US4112234A/en

1978-05-26 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1984-06-29 Publication of CY1229A publication Critical patent/CY1229A/en

Links

229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 2
150000002357 guanidines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 73
239000002253 acid Substances 0.000 claims description 51
238000000034 method Methods 0.000 claims description 50
150000003839 salts Chemical class 0.000 claims description 41
-1 4-methyl-5-imidazolyl Chemical group 0.000 claims description 32
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 29
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 28
231100000252 nontoxic Toxicity 0.000 claims description 27
230000003000 nontoxic effect Effects 0.000 claims description 27
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
230000008569 process Effects 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 19
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 14
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 14
JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000000304 alkynyl group Chemical group 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
239000012458 free base Chemical group 0.000 claims description 6
ACCDPTZPTFHVIV-UHFFFAOYSA-N 1-cyano-2-prop-2-ynyl-3-(2-sulfanylethyl)guanidine Chemical compound SCCNC(NC#N)=NCC#C ACCDPTZPTFHVIV-UHFFFAOYSA-N 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
125000003107 substituted aryl group Chemical group 0.000 claims description 5
KEDVUOWPLAHMLZ-UHFFFAOYSA-N 1-cyano-3-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]-2-prop-2-ynylguanidine Chemical compound CC=1NC=NC=1CSCCNC(NC#N)=NCC#C KEDVUOWPLAHMLZ-UHFFFAOYSA-N 0.000 claims description 4
239000002585 base Substances 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
CUKCVGDXLGQNOQ-UHFFFAOYSA-N 2-but-2-ynyl-1-cyano-3-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound CC#CCN=C(NC#N)NCCSCC=1N=CNC=1C CUKCVGDXLGQNOQ-UHFFFAOYSA-N 0.000 claims description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
XSBPYGDBXQXSCU-UHFFFAOYSA-N but-3-yn-1-amine Chemical compound NCCC#C XSBPYGDBXQXSCU-UHFFFAOYSA-N 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
230000027119 gastric acid secretion Effects 0.000 claims description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
LMDDPGHBJXJGAC-UHFFFAOYSA-N pent-4-yn-1-amine Chemical compound NCCCC#C LMDDPGHBJXJGAC-UHFFFAOYSA-N 0.000 claims description 3
ZQANEVLLTIIVTQ-UHFFFAOYSA-N 2-but-3-ynyl-1-cyano-3-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound CC=1NC=NC=1CSCCNC(NC#N)=NCCC#C ZQANEVLLTIIVTQ-UHFFFAOYSA-N 0.000 claims description 2
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
229940125773 compound 10 Drugs 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
230000002401 inhibitory effect Effects 0.000 claims description 2
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims description 2
RRSAAPWSPSWDIC-UHFFFAOYSA-N 1-but-3-yn-2-yl-3-cyano-2-(2-sulfanylethyl)guanidine Chemical compound C#CC(C)NC(NC#N)=NCCS RRSAAPWSPSWDIC-UHFFFAOYSA-N 0.000 claims 2
QEPHEFKVMHIVPD-UHFFFAOYSA-N 1-but-3-yn-2-yl-3-cyano-2-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine Chemical compound C#CC(C)NC(NC#N)=NCCSCC=1N=CNC=1C QEPHEFKVMHIVPD-UHFFFAOYSA-N 0.000 claims 2
LUUPYKRXMACHKV-UHFFFAOYSA-N 1-cyano-2-pent-4-ynyl-3-(2-sulfanylethyl)guanidine Chemical compound SCCNC(NC#N)=NCCCC#C LUUPYKRXMACHKV-UHFFFAOYSA-N 0.000 claims 2
DMWFSYFUGOVMOO-UHFFFAOYSA-N 2-but-3-ynyl-1-cyano-3-(2-sulfanylethyl)guanidine Chemical compound SCCNC(NC#N)=NCCC#C DMWFSYFUGOVMOO-UHFFFAOYSA-N 0.000 claims 2
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims 1
WTTRIOHOBKKNAU-UHFFFAOYSA-N 1-cyano-3-(2-methylbut-3-yn-2-yl)-2-(2-sulfanylethyl)guanidine Chemical compound C#CC(C)(C)NC(NC#N)=NCCS WTTRIOHOBKKNAU-UHFFFAOYSA-N 0.000 claims 1
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
VUGCBIWQHSRQBZ-UHFFFAOYSA-N 2-methylbut-3-yn-2-amine Chemical compound CC(C)(N)C#C VUGCBIWQHSRQBZ-UHFFFAOYSA-N 0.000 claims 1
PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 claims 1
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 44
CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 37
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238000006243 chemical reaction Methods 0.000 description 31
229960001380 cimetidine Drugs 0.000 description 27
239000000047 product Substances 0.000 description 25
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
229960001340 histamine Drugs 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 12
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239000007787 solid Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 6
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 6
210000004211 gastric acid Anatomy 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
208000008469 Peptic Ulcer Diseases 0.000 description 5
IULFXBLVJIPESI-UHFFFAOYSA-N bis(methylsulfanyl)methylidenecyanamide Chemical compound CSC(SC)=NC#N IULFXBLVJIPESI-UHFFFAOYSA-N 0.000 description 5
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238000001953 recrystallisation Methods 0.000 description 5
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
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GFNVWKLZHQYCOP-UHFFFAOYSA-N 2-but-2-ynylguanidine Chemical compound CC#CCN=C(N)N GFNVWKLZHQYCOP-UHFFFAOYSA-N 0.000 description 3
FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 3
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KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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AOQBTOKIEVBYSK-UHFFFAOYSA-N methyl n-cyano-n'-prop-2-ynylcarbamimidothioate Chemical compound N#CNC(SC)=NCC#C AOQBTOKIEVBYSK-UHFFFAOYSA-N 0.000 description 3
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OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 2
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229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 1
230000001746 atrial effect Effects 0.000 description 1
RIMGDBZXWSGBQN-UHFFFAOYSA-N burimamide Chemical compound CNC(=S)NCCCCC1=CN=C[N]1 RIMGDBZXWSGBQN-UHFFFAOYSA-N 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
230000002057 chronotropic effect Effects 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
230000008602 contraction Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000001186 cumulative effect Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000011067 equilibration Methods 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
210000004051 gastric juice Anatomy 0.000 description 1
210000001156 gastric mucosa Anatomy 0.000 description 1
230000005484 gravity Effects 0.000 description 1
239000000938 histamine H1 antagonist Substances 0.000 description 1
229960004931 histamine dihydrochloride Drugs 0.000 description 1
PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 description 1
229940077716 histamine h2 receptor antagonists for peptic ulcer and gord Drugs 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
150000002541 isothioureas Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
238000013289 male long evans rat Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
ILBIXZPOMJFOJP-UHFFFAOYSA-N n,n-dimethylprop-2-yn-1-amine Chemical compound CN(C)CC#C ILBIXZPOMJFOJP-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000012264 purified product Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000006215 rectal suppository Substances 0.000 description 1
229940100618 rectal suppository Drugs 0.000 description 1
238000000611 regression analysis Methods 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
210000005245 right atrium Anatomy 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
210000003462 vein Anatomy 0.000 description 1

Classifications

- 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
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants

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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CY1229A 1977-06-03 1978-05-26 Guanidine derivatives CY1229A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US80300977A	1977-06-03	1977-06-03
US82679677A	1977-08-22	1977-08-22
US05/848,959 US4112234A (en)	1977-08-22	1977-11-07	Imidazolylmethylthioethyl alkynyl guanidines

Publications (1)

Publication Number	Publication Date
CY1229A true CY1229A (en)	1984-06-29

Family

ID=27419995

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CY1231A CY1231A (en)	1977-06-03	1978-05-26	N-cyano-n'-alkynyl-s-substituted isothioureas
CY1229A CY1229A (en)	1977-06-03	1978-05-26	Guanidine derivatives
CY1230A CY1230A (en)	1977-06-03	1978-05-26	N-cyano-n'-alkynyl-n''-(2-mercaptoethyl)-guanidines

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
CY1231A CY1231A (en)	1977-06-03	1978-05-26	N-cyano-n'-alkynyl-s-substituted isothioureas

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CY1230A CY1230A (en)	1977-06-03	1978-05-26	N-cyano-n'-alkynyl-n''-(2-mercaptoethyl)-guanidines

Country Status (26)

Country	Link
JP (1)	JPS543067A (xx)
AR (2)	AR222797A1 (xx)
CA (1)	CA1110251A (xx)
CH (2)	CH641167A5 (xx)
CY (3)	CY1231A (xx)
DD (1)	DD140038A5 (xx)
DE (1)	DE2824066A1 (xx)
DK (1)	DK243178A (xx)
ES (3)	ES470474A1 (xx)
FI (1)	FI69069C (xx)
FR (2)	FR2401143A1 (xx)
GB (3)	GB1598628A (xx)
GR (1)	GR73860B (xx)
HK (3)	HK38284A (xx)
HU (1)	HU186766B (xx)
IE (1)	IE47543B1 (xx)
IL (1)	IL54819A (xx)
KE (1)	KE3373A (xx)
LU (1)	LU79725A1 (xx)
MY (3)	MY8500451A (xx)
NL (1)	NL7805935A (xx)
NO (3)	NO152214C (xx)
NZ (1)	NZ187376A (xx)
SE (3)	SE443784B (xx)
SG (1)	SG8584G (xx)
YU (4)	YU129778A (xx)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS568352A (en) *	1979-07-03	1981-01-28	Shionogi & Co Ltd	Aminoalkylvenzene derivative
US4339439A (en) *	1981-01-19	1982-07-13	Bristol-Myers Company	Pharmaceutical methods and compositions
JPS6018010U (ja) *	1983-07-18	1985-02-07	日産自動車株式会社	車両用空気調和装置の温度調整機構
JPS60113211U (ja) *	1984-01-06	1985-07-31	松下電器産業株式会社	自動車用空気調和装置
ES2007948A6 (es) *	1988-07-06	1989-07-01	Vinas Lab	Procedimiento para la obtencion de derivados propargilguanidicos.

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4024271A (en) *	1971-03-09	1977-05-17	Smith Kline & French Laboratories Limited	Pharmacologically active guanidine compounds
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
GB1531221A (en) *	1974-09-02	1978-11-08	Smith Kline French Lab	Process for preparing guanidine derivatives
GB1531231A (en) *	1974-09-02	1978-11-08	Smith Kline French Lab	Process for the production of cyanoguanidine derivatives
GB1533380A (en) *	1974-09-02	1978-11-22	Smith Kline French Lab	Process for the preparation of heterocyclic substituted thioureas and h-cyanoguanidines

1978
- 1978-05-25 NZ NZ187376A patent/NZ187376A/xx unknown
- 1978-05-25 CA CA304,045A patent/CA1110251A/en not_active Expired
- 1978-05-26 CY CY1231A patent/CY1231A/en unknown
- 1978-05-26 GB GB23611/78A patent/GB1598628A/en not_active Expired
- 1978-05-26 CY CY1229A patent/CY1229A/en unknown
- 1978-05-26 GB GB18923/80A patent/GB1598630A/en not_active Expired
- 1978-05-26 GB GB27637/79A patent/GB1598629A/en not_active Expired
- 1978-05-26 CY CY1230A patent/CY1230A/en unknown
- 1978-05-29 GR GR56374A patent/GR73860B/el unknown
- 1978-05-29 LU LU79725A patent/LU79725A1/xx unknown
- 1978-05-31 IL IL54819A patent/IL54819A/xx unknown
- 1978-05-31 DK DK243178A patent/DK243178A/da not_active Application Discontinuation
- 1978-05-31 YU YU01297/78A patent/YU129778A/xx unknown
- 1978-05-31 NL NL7805935A patent/NL7805935A/xx not_active Application Discontinuation
- 1978-05-31 AR AR272401A patent/AR222797A1/es active
- 1978-05-31 FI FI781737A patent/FI69069C/fi not_active IP Right Cessation
- 1978-06-01 DE DE19782824066 patent/DE2824066A1/de not_active Withdrawn
- 1978-06-02 IE IE1112/78A patent/IE47543B1/en unknown
- 1978-06-02 ES ES470474A patent/ES470474A1/es not_active Expired
- 1978-06-02 HU HU811135A patent/HU186766B/hu unknown
- 1978-06-02 JP JP6590078A patent/JPS543067A/ja active Granted
- 1978-06-02 NO NO781928A patent/NO152214C/no unknown
- 1978-06-02 FR FR7816601A patent/FR2401143A1/fr active Granted
- 1978-06-02 CH CH609278A patent/CH641167A5/de not_active IP Right Cessation
- 1978-06-02 SE SE7806525A patent/SE443784B/sv unknown
- 1978-06-05 DD DD78205794A patent/DD140038A5/de unknown
1979
- 1979-03-01 ES ES478202A patent/ES478202A1/es not_active Expired
- 1979-03-01 ES ES478203A patent/ES478203A1/es not_active Expired
- 1979-03-05 YU YU530/79A patent/YU41620B/xx unknown
- 1979-05-16 NO NO791637A patent/NO791637L/no unknown
- 1979-10-26 AR AR278645A patent/AR222503A1/es active
- 1979-11-23 FR FR7928943A patent/FR2436138A1/fr active Granted
1982
- 1982-09-27 YU YU2155/82A patent/YU40625B/xx unknown
- 1982-09-27 YU YU2154/82A patent/YU40624B/xx unknown
1983
- 1983-09-12 NO NO833255A patent/NO151824C/no unknown
- 1983-10-07 CH CH549283A patent/CH644591A5/de not_active IP Right Cessation
1984
- 1984-01-30 SG SG85/84A patent/SG8584G/en unknown
- 1984-02-10 KE KE3373A patent/KE3373A/xx unknown
- 1984-03-16 SE SE8401492A patent/SE8401492D0/xx not_active Application Discontinuation
- 1984-03-16 SE SE8401491A patent/SE8401491L/xx not_active Application Discontinuation
- 1984-05-03 HK HK382/84A patent/HK38284A/xx unknown
- 1984-05-03 HK HK380/84A patent/HK38084A/xx unknown
- 1984-05-03 HK HK381/84A patent/HK38184A/xx unknown
1985
- 1985-12-30 MY MY451/85A patent/MY8500451A/xx unknown
- 1985-12-30 MY MY452/85A patent/MY8500452A/xx unknown
- 1985-12-30 MY MY453/85A patent/MY8500453A/xx unknown

Also Published As

Publication number	Publication date
JPS543067A (en)	1979-01-11
HK38284A (en)	1984-05-11
SE8401492L (sv)	1984-03-16
DE2824066A1 (de)	1978-12-14
YU215582A (en)	1983-02-28
IL54819A (en)	1983-03-31
MY8500452A (en)	1985-12-31
FR2436138B1 (xx)	1982-12-03
NO151824B (no)	1985-03-04
AR222503A1 (es)	1981-05-29
CY1231A (en)	1984-06-29
SG8584G (en)	1985-02-08
HU186766B (en)	1985-09-30
YU41620B (en)	1987-12-31
YU53079A (en)	1983-09-30
YU40625B (en)	1986-02-28
MY8500453A (en)	1985-12-31
FI69069C (fi)	1985-12-10
GR73860B (xx)	1984-05-08
YU129778A (en)	1983-02-28
GB1598628A (en)	1981-09-23
SE8401492D0 (sv)	1984-03-16
FI69069B (fi)	1985-08-30
IE781112L (en)	1978-12-03
FI781737A7 (fi)	1978-12-04
ES478203A1 (es)	1979-06-01
NO833255L (no)	1978-12-05
CY1230A (en)	1984-06-29
CH644591A5 (en)	1984-08-15
FR2401143B1 (xx)	1981-12-11
FR2436138A1 (fr)	1980-04-11
FR2401143A1 (fr)	1979-03-23
KE3373A (en)	1984-03-23
GB1598629A (en)	1981-09-23
SE8401491D0 (sv)	1984-03-16
YU40624B (en)	1986-02-28
YU215482A (en)	1983-02-28
ES470474A1 (es)	1979-09-01
NO152214B (no)	1985-05-13
HK38084A (en)	1984-05-11
SE8401491L (sv)	1984-03-16
NO791637L (no)	1978-12-05
NO152214C (no)	1985-08-28
AR222797A1 (es)	1981-06-30
GB1598630A (en)	1981-09-23
NZ187376A (en)	1981-05-29
IL54819A0 (en)	1978-07-31
SE443784B (sv)	1986-03-10
JPS5639313B2 (xx)	1981-09-11
CH641167A5 (en)	1984-02-15
HK38184A (en)	1984-05-11
NO781928L (no)	1978-12-05
LU79725A1 (fr)	1979-02-02
SE7806525L (sv)	1978-12-04
NL7805935A (nl)	1978-12-05
CA1110251A (en)	1981-10-06
IE47543B1 (en)	1984-04-18
MY8500451A (en)	1985-12-31
DK243178A (da)	1978-12-04
NO151824C (no)	1985-06-12
DD140038A5 (de)	1980-02-06
ES478202A1 (es)	1979-06-01

Publication	Publication Date	Title
USRE33024E (en)	1989-08-15	Bronchodilating 8-hydroxy-5-(1R)-1-hydroxy-2-(N-((1R)-2-(p-methoxyphenyl)-1-methylethyl)-amino)ethyl) carbostyril and intermediates thereof
US4112234A (en)	1978-09-05	Imidazolylmethylthioethyl alkynyl guanidines
SU1380614A3 (ru)	1988-03-07	Способ получени производных арилтиазолов или их хлористоводородных или бромистоводородных солей
IE53274B1 (en)	1988-09-28	Chemical compounds derived from cyclobutene
EP0053407B1 (en)	1986-12-30	New imidazolylphenyl amidines, processes for their preparation and their pharmaceutical use, and intermediates of preparation
JPH0655728B2 (ja)	1994-07-27	ヒスタミン誘導体及びその製造方法並びに該誘導体を含有する医薬
KR840001075B1 (ko)	1984-07-31	티아졸 유도체의 제조방법
US4157347A (en)	1979-06-05	N-cyano isothioureas
US4499286A (en)	1985-02-12	Derivatives of thienylacetic acid amides and their pharmaceutically acceptable acid salts and a process for the preparation thereof
EP0294973A1 (en)	1988-12-14	Dopamine-beta-hydroxylase inhibitors
CY1229A (en)	1984-06-29	Guanidine derivatives
EP0038784A2 (en)	1981-10-28	3,8-Dialkylxanthines, processes for their preparation and compositions containing them
US4157340A (en)	1979-06-05	N,N'-[Bis(N-cyanoguanyl)]cystamine derivatives
US3449357A (en)	1969-06-10	2-((2,6-substituted)phenoxymethyl)-2-imidazolines
EP0105458B1 (en)	1989-11-23	Alpha-aryl-alpha-pyridylalkanoic acid derivatives, process for preparation thereof and pharmaceutical composition comprising the same
USRE31588E (en)	1984-05-22	Imidazolylmethylthioethyl alkynyl guanidines
US4310532A (en)	1982-01-12	Methods and piperidinyl-alkyl-benzamide composition for inhibiting H2 histamine receptors
US4200760A (en)	1980-04-29	Imidazolylalkylthioalkylamino-ethylene derivatives
SU1311621A3 (ru)	1987-05-15	Способ получени 2-гуанидино-4-триазолил-тиазолов
CA1142544A (en)	1983-03-08	N-cyano-n'-(2-[(4-methyl-5-imidazolyl) methylthio]ethyl) - n"-alkynylguanidines h.sub.2 receptor blocking agents
KR810000632B1 (ko)	1981-06-10	히스타민 h₂수용기 길항제 또는 비독성인 그의 약조제 가능한 산 첨가염의 제조방법
CA1130306A (en)	1982-08-24	N-cyano-n'-[2-[(4-methyl-5-imidazolyl) methylthio]ethyl]- n"-alkynylguanidines h.sub.2 receptor blocking agents
US4221737A (en)	1980-09-09	1-(Alkynyl)amino-1-(mercaptoalkyl)amino ethylenes
DE2605824A1 (de)	1976-08-26	N-acylaniline, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
US4703058A (en)	1987-10-27	β-methylene furanethanamines and use as anti-hypertensive agents