US3876647A - Certain n-cyanoguanidines - Google Patents
Certain n-cyanoguanidines Download PDFInfo
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- US3876647A US3876647A US384993A US38499373A US3876647A US 3876647 A US3876647 A US 3876647A US 384993 A US384993 A US 384993A US 38499373 A US38499373 A US 38499373A US 3876647 A US3876647 A US 3876647A
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
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- C—CHEMISTRY; METALLURGY
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C—CHEMISTRY; METALLURGY
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- 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
- C07D241/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
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- C—CHEMISTRY; METALLURGY
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/26—Radicals substituted by sulfur atoms
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
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- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Definitions
- ABSTRACT Primary E. ⁇ aminerAlan L. Rotman Allurney. Agent. or Firm-Joan S. Keps; Richard D. Foggio; William H. Edg'erton [57] ABSTRACT
- the compounds are cyanoguanidines, for example N- cyano-N'-methyl-N"-[2-((3-hydroxy-2-pyridyl)methylthio-ethyll-guanidine. which are inhibitors of histamine activity.
- This invention relates to pharmacologically active compounds, in particular to pharmacologically active cyanoguanidines, to processes of preparing these compounds and methods of inhibiting H2 histamine receptors with these compounds.
- the compounds of the invention can exist as the addition salts but. for convenience, reference will be made throughout this specification to the parent compounds.
- Histamine is a compound which is believed to act in such a way but. since the actions of histamine fall into more than one type, it is believed that there is more than one type of histamine receptor.
- antihistamines drugs commonly called antihistamines" (of which mepyramine is a typical example) is believed to involve a receptor which has been designated as H-l.
- a further group of substances has recently been described by Black et al. (Nature 1972, 236.
- H-2 receptors which are distinguished by the fact that they act at his tamine receptors other than the H-l receptor and these other receptors have been designated as H-2 receptors.
- H-2 receptors his tamine receptors other than the H-l receptor and these other receptors have been designated as H-2 receptors.
- This latter group of substances, to certain of which the present invention relates. are thus of utility in inhibiting certain actions of histamine which are not inhibited by the above-mentioned antihistamines".
- the substances of this invention may also be of utility as inhibitors of certain actions of gastrin. 1
- lower alkyl we mean an alkyl group containing from l to 4 carbon atoms.
- the cyanoguanidines with which the present invention is concerned may be represented by the following general formula:
- R is hydrogen or lower alkyl such as methyl
- X is hydrogen, lower alkyl, trifluoromethyl, hydroxyl, halogen or amino
- Z is sulphur or oxygen
- In is 0, l or 2 and n is 2 or 3, the sum of m and n being 3 or 4; or pharmaceutically acceptable acid addition salts thereof.
- R is methyl or ethyl.
- m is l and n is 2.
- Particularly useful specific compounds are N-cyano-N'-methyl-N"-[2-((3-hydroxy-2- pyridyl)methylthio)ethyl]guanidine, N-cyano-N'- methyl-N"-[2-((3-bromo-2-pyridyl)methylthio)ethyl]- guanidine and N-cyano-N '-ethyl-N 2-( 3-bromo-2 pyridyl )methylthio )ethyl ]guanidine.
- the compounds of the present invention may be produced from an amine of the Formula II:
- R, Z, X, m and n have the same significance as in Formula I
- a heavy metal salt of cyanamide such as the lead, mercury or cadmium salt.
- This process may be conveniently carried out in a solvent such as acetonitrile or oimethylformamide.
- a desulphurising agent such as a heavy metal salt or oxide and then treated cyanamide.
- the amine of Formula [I may be reacted with a metal salt of dicyanamide of formula MN (CN): wherein M is a metal eg an alkali metal such as sodium in an appropriate solvent and in the presence of an equivalent amount of a strong acid.
- M is a metal eg an alkali metal such as sodium in an appropriate solvent and in the presence of an equivalent amount of a strong acid.
- the compounds represented by Formula l have been found to have pharmacological activity in the animal body as antagonists to certain actions of histamine which are not blocked by antihistamines such as mepyramine. For example, they have been found to inhibit selectively the histaminestimulated secretion of gastric acid from the perfused stomachs of rats anaesthetised with urethane, at doses of from 0.5 to 256 micromoles per kilogram intravenously. Similarly, the action of these compounds may, in many cases, be demonstrated by their antagonism to the effects of histamine on other tissueswhich, according to the above-mentioned paper of Black et., al., are H-2 receptors.
- tissues are perfused isolated guinea-pig heart, isolated guinea-pig right atrium and isolated rat uterus.
- the compounds of the invention have been found to inhibit the secretion of gastric acid stimulated by pentagastrin or by food. In addition to the above the compounds of the invention also show some anti-inflammatory activity in conventional tests.
- the level of activity found for the compounds of the present invention is illustrated by the effective dose range in the anaesthetised rat, as mentioned above, of from 0.5 to 256 micromoles per kilogram, given intravenously. Many ofthe compounds of the present invention produce a 50% inhibition in this test at a dose of from 2 to micromoles per kilogram.
- compositions comprising a pharmaceutical carrier and a compound of Formula I or a pharmaceutically acceptable acid addition salt thereof and methods of inhibiting H-2 histamine receptors which comprise administering to an animal a compound of Formula I or a pharmaceutically acceptable acid addition salt thereof are also objects of this invention.
- the pharmaceutical carrier employed may be, for example. either a solid or liquid.
- solid carriers are lactose. terra alba, sucrose, talc, gelatin, agar, pectin, acacia, magnesium stearate, stearic acid and the like.
- liquid carriers are syrup, peanut oil, olive oil, water and the like.
- the preparation can be tableted, placed in a hard gelatin capsule in powder or pellet form, or in the form of a troche or lozcnge.
- the amount of solid carrier will vary widely but preferably will be from about 25 mg. to about l gm.
- the preparation may be in the form of a syrup, emulsion, soft gelatin capsule, sterile injectable liquid such as an ampoule, or an aqueous or nonaqueous liquid suspension.
- compositions are prepared by conventional techniques involving procedures such as mixing, granulating and compressing or dissolving the ingredients as appropriate to the desired preparation.
- the active ingredient will be present in the composition in an effective amount to inhibit histamine activity.
- the route of administration may be orally or parenterally.
- each dosage unit will contain the active ingredient in an amount of from about 50 mg. to about 250 mg., most preferably from about mg. to about 200 mg.
- the active ingredient will preferably be administered in equal doses one to three times per day.
- the daily dosage regimen will preferably be from about mg. to about 750 mg., most preferably from about 300 mg. to about 600 mg.
- the pharmacologically active compounds of the present invention will normally be administered as a pharmaceutical composition comprising as the or an essential active ingredient at least one such compound in the basic form or in the form of an addition salt with a pharmaceutically acceptable acid and in association with a pharmaceutical carrier therefor.
- addition salts include those with hydrochloric, hydrobromic, hydriodic, sulphuric, picric and maleic acids.
- compositions will be made up in a dosage unit form appropriate to the desired mode of administration, for example as a tablet, capsule, injectable solution or as a cream for topical administration.
- Example 1 N-Cyano-N-[ 2-( 3-hydroxy-2-pyridyl )methylthio )ethyl]-N"-methyl guanidine i.
- a solution of 2-((Z-aminoethyl)thiomethyl)-3- hydroxypyridine (7.5 g) in ethanol was added slowly to a solution of dimethylcyanodithioimidocarbonate (6.0 g) in ethanol, with stirring at room temperature. The mixture was set aside overnight at room temperature. Filtration afforded N-cyano-N-[2-((3-hydroxy-2- pyridyl)methylthio)ethylI-S-methylisothiourea (4.85 g), m.p.
- EXAMPLE 6 Ingredients Amounts Z-pyridyl )methylthio )ethyl Iguanidine. 150 mg. Sucrose mg. Starch 25 mg. Tale 5 mg. Stearic acid 2 mg.
- the ingredients are screened, mixed and filled into a hard gelatin capsule.
- the ingredients are screened, mixed and filled into a hard gelatin capsule.
- a compound of claim 1 such that m is l and n is N CN (GI-I Z(CI-I NB C I 4.
- a compound of claim 1 said compound being N- whereln R IS hydrogen or lower alkyl; X is hydrogen. cyan0 N,-methyl N,, [2 ((3 bmm0 2 lower alkyl. trifluoromethyl, hydroxyL halogen or amino; Z is sulphur or oxygen; m is O. l or 2 and n is pyndyl)methyhhlo)ethyuguamdme 2 or 3 the sum of m and n being 3 or 4. or a pharma- A C(ImPOUndHOf claim 1, Said comPound being N ceutically acceptable acid addition salt thereof. W 4( 'py y y 2. A compound of claim 1 such that R is methyl or m thyllguilmdlfieethyl.
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- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US523593A US3920822A (en) | 1972-09-05 | 1974-11-14 | Inhibition of histamine activity with cyanoguanidines |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB4116072A GB1397436A (en) | 1972-09-05 | 1972-09-05 | Heterocyclic n-cyanoguinidines |
GB615473 | 1973-02-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3876647A true US3876647A (en) | 1975-04-08 |
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ID=26240478
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
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US385027A Expired - Lifetime US3897444A (en) | 1972-09-05 | 1973-08-02 | Pharmacologically active compounds |
US384993A Expired - Lifetime US3876647A (en) | 1972-09-05 | 1973-08-02 | Certain n-cyanoguanidines |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
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US385027A Expired - Lifetime US3897444A (en) | 1972-09-05 | 1973-08-02 | Pharmacologically active compounds |
Country Status (14)
Country | Link |
---|---|
US (2) | US3897444A (de) |
JP (1) | JPS561309B2 (de) |
AU (1) | AU472456B2 (de) |
CA (1) | CA1045142A (de) |
CY (1) | CY855A (de) |
DE (1) | DE2344779C3 (de) |
FR (1) | FR2199467B2 (de) |
GB (1) | GB1397436A (de) |
HK (1) | HK55276A (de) |
IE (1) | IE38353B1 (de) |
KE (1) | KE2626A (de) |
MY (1) | MY7600229A (de) |
NL (1) | NL187240C (de) |
SG (1) | SG28676G (de) |
Cited By (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3953460A (en) * | 1973-05-17 | 1976-04-27 | Smith Kline & French Laboratories Limited | Ethylene derivatives |
US3979398A (en) * | 1973-02-08 | 1976-09-07 | Smith Kline & French Laboratories Limited | Sulphoxides |
US4002759A (en) * | 1973-05-17 | 1977-01-11 | Smith Kline & French Laboratories Limited | Pyridylbutylamino ethylene compounds |
US4024260A (en) * | 1973-05-17 | 1977-05-17 | Smith Kline & French Laboratories Limited | Ethylene derivatives |
US4028379A (en) * | 1975-05-15 | 1977-06-07 | Smith Kline & French Laboratories Limited | Process for preparing 2-amino-2-alkylthio-1-nitroethylene compounds |
US4049671A (en) * | 1974-09-02 | 1977-09-20 | Smith Kline & French Laboratories Limited | Process for preparing N-cyanoguanidines |
US4067984A (en) * | 1975-11-05 | 1978-01-10 | Smith Kline & French Laboratories Limited | Pyridylbutylamino ethylene compounds |
US4083983A (en) * | 1975-07-31 | 1978-04-11 | Smith Kline & French Laboratories Limited | Alkoxy pyridine compounds |
US4104382A (en) * | 1972-04-20 | 1978-08-01 | Smith Kline & French Laboratories Limited | Pharmaceutical compositions and methods of inhibiting H-1 and H-2 histamine receptors |
US4156727A (en) * | 1975-07-31 | 1979-05-29 | Smith Kline & French Laboratories Limited | Alkoxy pyridine compounds |
US4165378A (en) * | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
US4165377A (en) * | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidino imidazoles and thiazoles |
DE2928857A1 (de) * | 1978-07-19 | 1980-02-07 | Pliva Pharm & Chem Works | Verfahren zur herstellung von n-cyano- n'-methyl-n''- grosse eckige klammer auf 2- geschweifte klammer auf eckige klammer auf (5-methylimidazol-4-yl)-methyl eckige klammer zu -thio geschweifte klammer zu -aethyl grosse eckige klammer zu -guanidin |
US4200761A (en) * | 1978-04-26 | 1980-04-29 | Lek, Tovarna Farmacevtskih In Kemicnih Izdelkov, N.Sol.O. | Process for preparing N-cyano-N'methyl-N"-{2-[(4-methyl-5-imidazolyl)-methylthio]-ethyl} guanidine |
US4250316A (en) * | 1978-11-24 | 1981-02-10 | Bristol-Myers Company | Pyridyl guanidine anti-ulcer agents |
US4256752A (en) * | 1978-02-17 | 1981-03-17 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler | Treatment of ulcers with acylated aminoalkyl cyanoguanidines containing a heterocyclic residue |
US4287198A (en) * | 1971-03-09 | 1981-09-01 | Smith Kline & French Laboratories Limited | Pharmacologically active guanidine compounds |
US4293699A (en) * | 1972-02-03 | 1981-10-06 | Smith Kline & French Laboratories Limited | Pharmacologically active guanidine compounds |
US4342765A (en) * | 1979-01-18 | 1982-08-03 | Imperial Chemical Industries Limited | Guanidine derivatives and pharmaceutical compositions containing them |
US4514413A (en) * | 1982-04-10 | 1985-04-30 | Basf Aktiengesellschaft | Gastric acid secretion inhibiting N-(imidazol-1-ylalkyl)thiourea derivatives |
US20120259094A1 (en) * | 2009-10-15 | 2012-10-11 | Monash University | Affinity ligands and methods for protein purification |
WO2022034121A1 (en) | 2020-08-11 | 2022-02-17 | Université De Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
Families Citing this family (28)
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 |
US4000302A (en) * | 1972-04-20 | 1976-12-28 | Smith Kline & French Laboratories Limited | Pharmaceutical compositions and methods of inhibiting H-1 and H-2 histamine receptors |
GB1421999A (en) * | 1973-02-08 | 1976-01-21 | Smith Kline French Lab | Heterocyclic containing sulphoxides |
GB1489879A (en) * | 1974-12-20 | 1977-10-26 | Leo Pharm Prod Ltd | N'-cyano-n'-3-pyridylguanidines |
IN146736B (de) * | 1975-10-02 | 1979-08-25 | Smith Kline French Lab | |
GB1565966A (en) | 1976-08-04 | 1980-04-23 | Allen & Hanburys Ltd | Aminoalkyl furan derivatives |
DD129906A5 (de) * | 1976-09-21 | 1978-02-15 | Smith Kline French Lab | Verfahren zur herstellung einer kristallographisch reinen polymorphen form von cimetidin(cimetidin a) |
NZ184893A (en) * | 1976-09-21 | 1980-11-28 | Smith Kline French Lab | Pure crystalline form of cimetidine a(n-methyl-n-cyano-n-(-2-(5-methyl-4imidazolyl) methylthio) ethyl)-guanidine andpharmaceutical compositions containing it |
DE2817078C2 (de) * | 1977-04-20 | 1995-06-14 | Zeneca Ltd | Guanidinderivate |
GB1601459A (en) | 1977-05-17 | 1981-10-28 | Allen & Hanburys Ltd | Aminoalkyl thiophene derivatives |
CA1110251A (en) * | 1977-06-03 | 1981-10-06 | Ronnie R. Crenshaw | N-cyano-n'- 2-¬(4-methyl-5- imidazolyl)methylthio|ethyl - n"-alkynylguanidines h.sub.2 receptor blocking agents |
DE2800148A1 (de) | 1978-01-03 | 1979-07-12 | Basf Ag | Verfahren zur herstellung von 4-methyl-5-chlormethyl-imidazol |
DE2963363D1 (en) | 1978-05-24 | 1982-09-09 | Ici Plc | Antisecretory thiadiazole derivatives, processes for their manufacture and pharmaceutical compositions containing them |
JPS5914460B2 (ja) * | 1978-12-27 | 1984-04-04 | 相互薬工株式会社 | H↓2受容体「きつ」抗剤シメチジンの製造法 |
NL8000869A (nl) * | 1979-02-16 | 1980-08-19 | Eisai Co Ltd | Cyanoguanidine-derivaten en werkwijze voor de bereiding daarvan. |
US4220654A (en) * | 1979-06-04 | 1980-09-02 | Merck & Co., Inc. | Cyclic imidazole cyanoguanidines |
DE3107599C2 (de) * | 1981-02-27 | 1982-12-16 | Ludwig Heumann & Co GmbH, 8500 Nürnberg | N-Cyan-N'-methyl-N"-{2-[(5-methylthio-imidazol-4-yl)-methylthio]-äthyl}-guanidin, Verfahren zu seiner Herstellung und diese Verbindung enthaltende Arzneimittel |
JPS5933267A (ja) * | 1982-08-19 | 1984-02-23 | Fujimoto Seiyaku Kk | グアニジン誘導体およびその製造法 |
NL8303965A (nl) * | 1982-12-08 | 1984-07-02 | Degussa | Nieuwe etheendiamine- en guanidine-derivaten; werkwijze voor het bereiden daarvan; geneesmiddelen die ze bevatten; werkwijze voor het bereiden van dergelijke geneesmiddelen; toepassing van de verbindingen voor het bereiden van geneesmiddelen en in de geneeskunde. |
US4565815A (en) * | 1982-12-30 | 1986-01-21 | Biomeasure, Inc. | Pyrazolo[1,5-a]-1,3,5-triazines |
US4495193A (en) * | 1982-12-30 | 1985-01-22 | Biomeasure, Inc. | Imidazole compounds which reduce gastric acid secretion |
US4617311A (en) * | 1985-05-17 | 1986-10-14 | Eli Lilly And Company | Antiasthmatic method |
DE3531504A1 (de) * | 1985-09-04 | 1987-03-12 | Basf Ag | 3-aminomethylpyrrol-1-yl-alkylamine und diese verbindungen enthaltende therapeutische mittel |
IE58373B1 (en) * | 1986-06-18 | 1993-09-08 | Bloomfield Frederick Jacob | 5-Lipoxygenase pathway inhibitors |
JPH085859B2 (ja) * | 1986-07-01 | 1996-01-24 | 日本バイエルアグロケム株式会社 | 新規アルキレンジアミン類 |
IE960441L (en) * | 1988-12-27 | 1990-06-27 | Takeda Chemical Industries Ltd | Guanidine derivatives, their production and insecticides |
US5160549A (en) * | 1990-10-31 | 1992-11-03 | Foster Wheeler Energy Corporation | Tube fin trimming machine and method for use |
IT1299198B1 (it) * | 1998-03-05 | 2000-02-29 | Nicox Sa | Sali nitrati di farmaci antiulcera |
Citations (3)
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US3734924A (en) * | 1970-10-14 | 1973-05-22 | Smith Kline French Lab | Carboxamidines |
US3759944A (en) * | 1970-10-14 | 1973-09-18 | Smith Kline French Lab | Isothioureas and their derivatives |
US3806511A (en) * | 1971-04-30 | 1974-04-23 | Sumitomo Chemical Co | 1-(3-pyridyl)-2-benzylthio-3-loweralkyl-isothio ureas and derivatives thereof |
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US3036083A (en) * | 1959-05-15 | 1962-05-22 | Ciba Geigy Corp | Certain 2-pyridyl lower alkyl guanidines |
US3074955A (en) * | 1960-11-30 | 1963-01-22 | Us Vitamin Pharm Corp | Pyridylalkyl dicyandiamides and guanylureas |
BE758145A (fr) * | 1969-10-29 | 1971-04-28 | Smith Kline French Lab | Iso-thio-urees et derives |
BE758146A (fr) * | 1969-10-29 | 1971-04-28 | Smith Kline French Lab | Derives de l'amidine |
GB1338169A (en) * | 1971-03-09 | 1973-11-21 | Smith Kline French Lab | Ureas thioureas and guanidines |
IE36050B1 (en) * | 1971-03-09 | 1976-08-04 | Smith Kline French Lab | Ureas thioureas and guanidines |
-
1972
- 1972-09-05 GB GB4116072A patent/GB1397436A/en not_active Expired
-
1973
- 1973-07-26 CA CA177,408A patent/CA1045142A/en not_active Expired
- 1973-08-02 US US385027A patent/US3897444A/en not_active Expired - Lifetime
- 1973-08-02 US US384993A patent/US3876647A/en not_active Expired - Lifetime
- 1973-08-03 AU AU58903/73A patent/AU472456B2/en not_active Expired
- 1973-08-21 CY CY855A patent/CY855A/xx unknown
- 1973-08-22 IE IE1466/73A patent/IE38353B1/xx not_active IP Right Cessation
- 1973-09-04 FR FR7331885A patent/FR2199467B2/fr not_active Expired
- 1973-09-04 NL NLAANVRAGE7312198,A patent/NL187240C/xx not_active IP Right Cessation
- 1973-09-05 DE DE2344779A patent/DE2344779C3/de not_active Expired
- 1973-09-05 JP JP10012573A patent/JPS561309B2/ja not_active Expired
-
1976
- 1976-05-18 KE KE2626*UA patent/KE2626A/xx unknown
- 1976-09-08 HK HK552/76*UA patent/HK55276A/xx unknown
- 1976-12-31 MY MY1976229A patent/MY7600229A/xx unknown
- 1976-12-31 SG SG286/76A patent/SG28676G/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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US3734924A (en) * | 1970-10-14 | 1973-05-22 | Smith Kline French Lab | Carboxamidines |
US3759944A (en) * | 1970-10-14 | 1973-09-18 | Smith Kline French Lab | Isothioureas and their derivatives |
US3806511A (en) * | 1971-04-30 | 1974-04-23 | Sumitomo Chemical Co | 1-(3-pyridyl)-2-benzylthio-3-loweralkyl-isothio ureas and derivatives thereof |
Cited By (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4287198A (en) * | 1971-03-09 | 1981-09-01 | Smith Kline & French Laboratories Limited | Pharmacologically active guanidine compounds |
US4293699A (en) * | 1972-02-03 | 1981-10-06 | Smith Kline & French Laboratories Limited | Pharmacologically active guanidine compounds |
US4104382A (en) * | 1972-04-20 | 1978-08-01 | Smith Kline & French Laboratories Limited | Pharmaceutical compositions and methods of inhibiting H-1 and H-2 histamine receptors |
US3979398A (en) * | 1973-02-08 | 1976-09-07 | Smith Kline & French Laboratories Limited | Sulphoxides |
US4002759A (en) * | 1973-05-17 | 1977-01-11 | Smith Kline & French Laboratories Limited | Pyridylbutylamino ethylene compounds |
US4024260A (en) * | 1973-05-17 | 1977-05-17 | Smith Kline & French Laboratories Limited | Ethylene derivatives |
US3953460A (en) * | 1973-05-17 | 1976-04-27 | Smith Kline & French Laboratories Limited | Ethylene derivatives |
US4049671A (en) * | 1974-09-02 | 1977-09-20 | Smith Kline & French Laboratories Limited | Process for preparing N-cyanoguanidines |
US4028379A (en) * | 1975-05-15 | 1977-06-07 | Smith Kline & French Laboratories Limited | Process for preparing 2-amino-2-alkylthio-1-nitroethylene compounds |
US4083983A (en) * | 1975-07-31 | 1978-04-11 | Smith Kline & French Laboratories Limited | Alkoxy pyridine compounds |
US4264608A (en) * | 1975-07-31 | 1981-04-28 | Smith Kline & French Laboratories Limited | Pharmacologically active compounds |
US4426526A (en) | 1975-07-31 | 1984-01-17 | Smith Kline & French Laboratories Limited | Alkoxypyridyl alkylamines |
US4156727A (en) * | 1975-07-31 | 1979-05-29 | Smith Kline & French Laboratories Limited | Alkoxy pyridine compounds |
US4067984A (en) * | 1975-11-05 | 1978-01-10 | Smith Kline & French Laboratories Limited | Pyridylbutylamino ethylene compounds |
US4234735A (en) * | 1977-04-20 | 1980-11-18 | Imperial Chemical Industries Limited | Guanidino imidazoles and thiazoles |
US4262126A (en) * | 1977-04-20 | 1981-04-14 | Imperial Chemical Industries Limited | Guanidine derivatives of imidazoles and thiazoles |
US4165378A (en) * | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
US4165377A (en) * | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidino imidazoles and thiazoles |
US4256752A (en) * | 1978-02-17 | 1981-03-17 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler | Treatment of ulcers with acylated aminoalkyl cyanoguanidines containing a heterocyclic residue |
US4200761A (en) * | 1978-04-26 | 1980-04-29 | Lek, Tovarna Farmacevtskih In Kemicnih Izdelkov, N.Sol.O. | Process for preparing N-cyano-N'methyl-N"-{2-[(4-methyl-5-imidazolyl)-methylthio]-ethyl} guanidine |
DE2928857A1 (de) * | 1978-07-19 | 1980-02-07 | Pliva Pharm & Chem Works | Verfahren zur herstellung von n-cyano- n'-methyl-n''- grosse eckige klammer auf 2- geschweifte klammer auf eckige klammer auf (5-methylimidazol-4-yl)-methyl eckige klammer zu -thio geschweifte klammer zu -aethyl grosse eckige klammer zu -guanidin |
DE2928857B2 (de) | 1978-07-19 | 1981-07-23 | Pliva pharmazeutische und chemische Fabrik, Zagreb | Verfahren zur Herstellung von N-Cyano-N'-methyl-N''-[2-{[(5-methylimidazol-4-yl)-methyl]-thio}-ethyl]-guanidin |
US4250316A (en) * | 1978-11-24 | 1981-02-10 | Bristol-Myers Company | Pyridyl guanidine anti-ulcer agents |
US4342765A (en) * | 1979-01-18 | 1982-08-03 | Imperial Chemical Industries Limited | Guanidine derivatives and pharmaceutical compositions containing them |
US4514413A (en) * | 1982-04-10 | 1985-04-30 | Basf Aktiengesellschaft | Gastric acid secretion inhibiting N-(imidazol-1-ylalkyl)thiourea derivatives |
US20120259094A1 (en) * | 2009-10-15 | 2012-10-11 | Monash University | Affinity ligands and methods for protein purification |
US8748582B2 (en) * | 2009-10-15 | 2014-06-10 | Monash University | Affinity ligands and methods for protein purification |
WO2022034121A1 (en) | 2020-08-11 | 2022-02-17 | Université De Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
Also Published As
Publication number | Publication date |
---|---|
SG28676G (en) | 1987-04-03 |
IE38353B1 (en) | 1978-03-01 |
AU472456B2 (en) | 1976-05-27 |
IE38353L (en) | 1974-03-05 |
HK55276A (en) | 1976-09-17 |
MY7600229A (en) | 1976-12-31 |
KE2626A (en) | 1976-05-28 |
DE2344779C3 (de) | 1981-05-27 |
GB1397436A (en) | 1975-06-11 |
FR2199467B2 (de) | 1977-01-28 |
AU5890373A (en) | 1975-02-06 |
NL7312198A (de) | 1974-03-07 |
DE2344779A1 (de) | 1974-03-14 |
JPS561309B2 (de) | 1981-01-13 |
FR2199467A2 (de) | 1974-04-12 |
JPS4975574A (de) | 1974-07-20 |
CY855A (en) | 1976-09-10 |
US3897444A (en) | 1975-07-29 |
CA1045142A (en) | 1978-12-26 |
DE2344779B2 (de) | 1979-04-26 |
NL187240C (nl) | 1991-07-16 |
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