HK26788A - Guanidine derivatives and pharmaceutical compositions containing them - Google Patents

Guanidine derivatives and pharmaceutical compositions containing them

Info

Publication number
HK26788A
HK26788A HK267/88A HK26788A HK26788A HK 26788 A HK26788 A HK 26788A HK 267/88 A HK267/88 A HK 267/88A HK 26788 A HK26788 A HK 26788A HK 26788 A HK26788 A HK 26788A
Authority
HK
Hong Kong
Prior art keywords
alkyl
guanidine
hydrogen
methoxycarbonyl
compounds
Prior art date
Application number
HK267/88A
Other languages
German (de)
English (en)
Inventor
Mohammad Mehdi Nafissi-Varchei
Original Assignee
Schering Corporation
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.)
Filing date
Publication date
Application filed by Schering Corporation filed Critical Schering Corporation
Publication of HK26788A publication Critical patent/HK26788A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
    • C07C279/24—Y being a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/28—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to cyano groups, e.g. cyanoguanidines, dicyandiamides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
    • C07C323/43—Y being a hetero atom
    • C07C323/44—X or Y being nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D211/56—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
    • C07D309/14—Nitrogen atoms not forming part of a nitro radical

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyridine Compounds (AREA)
  • Quick-Acting Or Multi-Walled Pipe Joints (AREA)

Claims (10)

1. Composés caractérisés en ce qu'ils sont représentés par la formule générale leurs isomères aux groupes guanidines et des sels pharmaceutiquement acceptables de tels composés, dans laquelle
R6 est alkyle C1 à C6 ou alkyle C1 à C6 substitué par alkoxy C1 à C6, hydroxy ou amino;
un des X et Y est CR5 et l'autre est CH ou N;
R1 est hydrogène, halogène, nitro, amino, NHCOR8 ou NHSO2R8;
R2 et R3 sont indépendamment choisis parmi hydrogène, N-alkyl-pipéridyle (dans lequel le groupe alkyle a 1 à 4 atomes de carbone), tétrahydropyranyle, morpholinyle, pipéridyle et alkyle C1 à C6 substitué par un ou plusieurs substituants choisis parmi OH, SCH3, COR9, OSO3H, SO3H, COOR10, pipérazinyle, pyridyle et à condition que R2 et R3 ne soient pas simultanément l'hydrogène;
un des R4 et R5 est choisi parmi hydrogène, alkyle C1 à C6 et alkoxy C1 à C6 et l'autre parmi hydrogène, alkyle C1 à C6 et R14Z dans lequel R14 est alkyle C1 à C6 ou phényle et Z représente O, S, SOn ou SO2NR15, n valant 1, 2 ou 3 et R15 étant hydrogène ou alkyle C1 à C6; dans les définitions ci-dessus;
R8 est alkyle C1 à C6, alkyle C1 à C6 substitué par phényle ou halogène, phényle ou phényle substitué par alkyle C1 à C6 ou par halogène;
R9 est alkyle C1 à C6, acyle C1 à C6 ou un résidu peptide ayant jusqu'à trois amino acides;
R10 est hydrogène ou alkyle C1 à C6;
R12 et R13 sont indépendamment choisi parmi hydrogène, alkyle C1 à C6,R11 étant alkyle C1 à C6.
2. Composés suivant la revendication 1, caractérisés en ce que R4 est l'hydrogène, X est CR5 et Y est CH ou N.
3. Composés suivant la revendication 2, caractérisés en ce que R1 est choisi parmi NO2, NH2 et NHCOR 8 .
4. Composés suivant la revendication 3, caractérisés en ce que R2 est l'hydrogène, R3 représente un groupe alkyle C1 à C6 substitué et R5 est R14Z.
5. Composés suivant la revendication 4, caractérisés en ce que R3 représente un groupe alkyle C1 à C6 substitué par COOR10, pipérazinyle, pyridyle, SO3H ou OSO3H.
6. Composés suivant la revendication 5, caractérisés en ce qu'ils sont représentés par la formule dans laquelle
R1 est NO2, NH2 ou NHCOCH3 et
R3 est alkyle C1 à C3 substitué par un substituant choisi parmi pipérazinyle, COOH, diéthylamino, SO3H et OSO3H.
7. Composés suivant la revendication 6, caractérisés en ce qu'ils sont:
N-méthoxycarbonyl-N'-(2-nitro-5-propylthiophényl)-N"-[2-(N-pipérazinyl)éthyl]guanidine;
N-méthoxycarbonyl-N'-[2(N'-cyano-N"-méthylguanidino)éthyl]-N"-[2-nitro-5-propylthiophényl]guanidine;
N-méthoxycarbonyl-N'-(2-nitro-5-propylthiophényl)-N"-(2-diéthylaminoéthyl)guanidine;
N-méthoxycarbonyl-N'-(2-nitro-5-propylthiophényl)-N"-(2-carboxyéthyl)guanidine;
N-méthoxycarbonyl-N'-[2-(N'-cyano-N"-méthylguanidino)éthyl]-N"-(2-amino-5-propylthiophényl)guanidine;
N-méthoxycarbonyl-N'-[2-(N'-cyano-N"-méthylguanidino)éthyl]-N"-[2-acétamido-5-propylthiophényl]guanidine;
N-méthoxycarbonyl-N'-(3-carboxypropyl)-N"-(2-nitro-5-propylthiophényl)guanidine; et
sel sodique de N-méthoxycarbonyl-N'-carboxyméthyl-N"-(2-nitro-5-propylthiophényl)guanidine.
8. Compositions pharmaceutiques caractérisées en ce qu'elles comprennent comme ingrédient actif un composé comme défini dans n'importe laquelle des revendications 1 à 7.
9. Procédé de préparation de composés de formule I, comme définis dans la revendication 1, caractérisé en ce qu'on fait réagir une isothiourée de formule IIIavec une amine de formule IV, dans lesquelles R1, R2, R3, R4, R6, X et Y sont comme définis dans la revendication 1, puis, si on le désire, transforme en un sel.
10. Procédé de préparation de compositions pharmaceutiques commes définies dans la revendication 8, caractérisé en ce qu'un composé suivant n'importe laquelle des revendications 1 à 7 est mis sous une forme appropriée pour application pharmaceutique.
HK267/88A 1980-10-20 1988-04-14 Guanidine derivatives and pharmaceutical compositions containing them HK26788A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US06/198,424 US4348406A (en) 1980-10-20 1980-10-20 Novel guanidine derivatives

Publications (1)

Publication Number Publication Date
HK26788A true HK26788A (en) 1988-04-22

Family

ID=22733331

Family Applications (1)

Application Number Title Priority Date Filing Date
HK267/88A HK26788A (en) 1980-10-20 1988-04-14 Guanidine derivatives and pharmaceutical compositions containing them

Country Status (20)

Country Link
US (3) US4348406A (fr)
EP (2) EP0063158A1 (fr)
JP (2) JPH0323540B2 (fr)
AT (1) ATE13423T1 (fr)
AU (1) AU548628B2 (fr)
CA (1) CA1248949A (fr)
CY (1) CY1424A (fr)
DE (1) DE3170623D1 (fr)
DK (1) DK255682A (fr)
ES (1) ES506337A0 (fr)
HK (1) HK26788A (fr)
HU (1) HU183749B (fr)
IE (1) IE51871B1 (fr)
IL (1) IL64081A (fr)
MY (1) MY8700682A (fr)
NZ (1) NZ198679A (fr)
PT (1) PT73841B (fr)
SG (1) SG112187G (fr)
WO (1) WO1982001367A1 (fr)
ZA (1) ZA817265B (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0147537A1 (fr) * 1983-09-23 1985-07-10 Schering Corporation Phenylguanidines
US4701447A (en) * 1983-09-23 1987-10-20 Schering Corporation N-((2-nitro)phenyl)-N' (organic acid) guanidine anthelmintics
US4723029A (en) * 1983-09-23 1988-02-02 Schering Corporation Organic acid-substituted guanidine anthelmintics
AT401086B (de) * 1985-11-28 1996-06-25 Gossler Ewald Verfahren zum verdichten von gasen
GB8903592D0 (en) * 1989-02-16 1989-04-05 Boots Co Plc Therapeutic agents
HU205343B (en) * 1989-06-21 1992-04-28 Chinoin Gyogyszer Es Vegyeszet New process for producing guanidine derivatives
GB9915709D0 (en) 1999-07-05 1999-09-08 Guilden Ltd Vehicle suspension systems
CA2616512A1 (fr) * 2005-07-28 2007-02-08 Intervet International B.V. Nouveaux benzimidazolyl(thio)carbamates ayant une activite antiparasitaire et synthese de ceux-ci
WO2007144362A1 (fr) 2006-06-14 2007-12-21 Intervet International B.V. Suspension contenant du carbamate de benzimidazole et un polysorbate
WO2008091358A1 (fr) * 2006-06-12 2008-07-31 Smith And Nephew Inc Systèmes, procédés et dispositifs pour une résection tibiale

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL38933A0 (en) * 1971-03-17 1972-05-30 Ciba Geigy Ag New carbamates,their manufacture and their use in plant protection
US4097673A (en) * 1974-11-01 1978-06-27 E. I. Du Pont De Nemours And Company Herbicidal carbamates and thiolcarbamates
US3941824A (en) * 1973-05-02 1976-03-02 E. I. Du Pont De Nemours & Co. Herbicidal carbamates and thiolcarbamates
AR213309A1 (es) * 1976-05-05 1979-01-15 Rohm & Haas Procedimiento para preparar 2-amino-isotioureidobencenos substituidos
DE2651467A1 (de) * 1976-11-11 1978-05-18 Bayer Ag Substituierte o-phenylendiaminderivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
US4293569A (en) * 1978-05-12 1981-10-06 E. R. Squibb & Sons, Inc. Substituted phenylguanindines and method
DE2836385A1 (de) 1978-08-19 1980-03-06 Hoechst Ag Monocarboxylate von phenylguanidinsulfonsaeureestern, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
US4217358A (en) 1979-04-18 1980-08-12 E. R. Squibb & Sons, Inc. Substituted phenylguanidines and method

Also Published As

Publication number Publication date
CA1248949A (fr) 1989-01-17
JPH0323540B2 (fr) 1991-03-29
SG112187G (en) 1988-05-20
MY8700682A (en) 1987-12-31
IL64081A0 (en) 1982-01-31
DE3170623D1 (en) 1985-06-27
EP0050286B1 (fr) 1985-05-22
NZ198679A (en) 1985-02-28
EP0063158A1 (fr) 1982-10-27
ZA817265B (en) 1982-09-29
DK255682A (da) 1982-06-07
JPH0432051B2 (fr) 1992-05-28
PT73841A (en) 1981-11-01
US4435398A (en) 1984-03-06
ES8206455A1 (es) 1982-08-16
ATE13423T1 (de) 1985-06-15
JPH03264527A (ja) 1991-11-25
EP0050286A2 (fr) 1982-04-28
EP0050286A3 (en) 1982-05-26
IE812453L (en) 1982-04-20
IL64081A (en) 1985-12-31
PT73841B (en) 1983-11-07
WO1982001367A1 (fr) 1982-04-29
US4348406A (en) 1982-09-07
ES506337A0 (es) 1982-08-16
HU183749B (en) 1984-05-28
AU7809281A (en) 1982-05-11
AU548628B2 (en) 1985-12-19
CY1424A (en) 1988-09-02
JPS57501850A (fr) 1982-10-14
US4406893A (en) 1983-09-27
IE51871B1 (en) 1987-04-15

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PC Patent ceased (i.e. patent has lapsed due to the failure to pay the renewal fee)