WO1994021616A1 - Heterocycle-containing amidine derivatives, their preparation and use - Google Patents
Heterocycle-containing amidine derivatives, their preparation and use Download PDFInfo
- Publication number
- WO1994021616A1 WO1994021616A1 PCT/EP1994/000856 EP9400856W WO9421616A1 WO 1994021616 A1 WO1994021616 A1 WO 1994021616A1 EP 9400856 W EP9400856 W EP 9400856W WO 9421616 A1 WO9421616 A1 WO 9421616A1
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- alkyl
- formula
- alkoxy
- compounds
- phenyl
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- 0 CC1*(C)CCCC1 Chemical compound CC1*(C)CCCC1 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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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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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
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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
- C07D233/66—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 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
- C07D233/84—Sulfur atoms
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- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
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- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/26—Oxygen atoms
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
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- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
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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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- 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
- C07D263/34—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 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
- C07D263/36—One oxygen atom
- C07D263/38—One oxygen atom attached in position 2
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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
- C07D263/34—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 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
- C07D263/46—Sulfur atoms
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
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- 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
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/16—Sulfur atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D277/32—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 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
- C07D277/34—Oxygen 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
- C07D277/32—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 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
- C07D277/36—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
- C07D277/32—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 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/70—Sulfur atoms
- C07D277/74—Sulfur atoms substituted by carbon 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
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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
- C07D285/13—Oxygen atoms
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Definitions
- the invention relates to new, heterocycle-containing amidine derivatives, their preparation by conventional methods and their use as active ingredients in
- a 1 is a straight-chain or branched double-bonded aliphatic C 2 -C 6 group, which can also contain a double or triple bond, or one of the groups
- X 1 for O, S, SO, SO 2 , CH 2 , NH or
- Chiral compounds of the formula I can be in the form of racemates, in enantiomerically pure or enriched form and in each case as a base or as salts with inorganic or organic, in particular physiologically
- R 1 and R 2 which are the same or different
- C 1 -C 4 alkyl can be substituted for halogen, OH, CF 3 , R 5 , OR 6 , COR 6 ,
- R 5 represents a heterocyclic five-membered ring with 1 to 3 heteroatoms and the formula
- D, E and G which may be the same or different, are CH, N, C- (C 1 -C 4 alkyl) or
- C is phenyl and L is Ooer S
- R 4 for H, halogen, NH 2 , NH- (C 1 -C 4 alkyl), C 1 -C 4 alkyl, N (C 1 -C 4 alkyl) 2 , OH, C 1 -C 4 - Alkoxy, phenyl,
- R 5 is H, C 1 -C 12 alkyl, pydridyl, phenyl, optionally by halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy
- R 6 for C 1 -C 12 alkyl, phenyl or optionally
- R 7 is H or C 1 -C 12 alkyl
- R 8 , R 9 (which may be the same or different)
- R 10 is H or C 1 -C 4 alkyl
- R 11 , R 12 which can be the same or different
- R 13 , R 14 which may be the same or different,
- radicals from the group fluorine, chlorine, bromine, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or pseudohalogens such as CN, CF 3 may be substituted, or for pyridyl.
- a 1 contains a double or triple bond, this is generally not a hetero atom
- R 3 generally means hydrogen only if at least one of the radicals R 1 , R 2 is not hydrogen.
- a 1 ' (CH 2 ) 2-6 , CH 2 -C 6 H 4 -CH 2 ,
- CH 2 -C C-CH 2 ;
- X 1 ' O, S;
- Het ' a group of the above formulas a, b, e, f, g, k, n, where R 1 , R 2 , R 3 , the may be the same or different, mean H, R 5 , OR 5 or COR 5 and
- R 1 and R 2 together also one
- condensed ring can mean.
- Ammonia in an alcohol such as methanol, ethanol, n-propanol, i-propanol, or in an inert solvent, such as dichloromethane,
- Tetrahydrofuran, dioxane at temperatures between about 0 and 50 ° C, preferably at about 20 ° C. 2. Reduction of an amidoxime of the formula
- Het, R 4 , A and B have the above meaning
- a catalyst such as Raney nickel, palladium or platinum.
- O or S can also be according to the scheme
- Metal hydroxides, metal hydrides at temperatures between about 0 and 140 ° C or the boiling point of the reaction mixture.
- the phenols or thiophenols can also be used in the form of salts, for example the alkali salts.
- Suitable as a nucleofugic leaving group eg halogens, such as Br, Cl or residues of
- Sulfonic acids such as methanesulfonic acid
- the starting materials X and XI are preferably from the corresponding nitriles of the formula
- the further synthetic route consists in the reaction of the corresponding nitriles with HCl via the stage of the imide chlorides or the direct reaction with eg
- reaction can also be carried out with a trialkyloxonium salt such as
- nitriles XVI can be reacted with hydroxylamine in alcohols, for example methanol, ethanol, Propanol, isopropanol, the corresponding amidoximes of the formula XI obtained.
- the starting materials of the formulas XII, XIII, XIV and XV can also be prepared by conventional processes.
- the compounds according to the invention can be used therapeutically, in particular because of their
- LTB 4 -antagonistic effect are therefore particularly suitable for use in those diseases in which inflammatory and / or allergic processes play a role, for example IBD (inflammatory bowel diseases), allergic rhinitis; ARDS (adult respiratory distress syndron), asthma, colitis
- IBD inflammatory bowel diseases
- ARDS adult respiratory distress syndron
- asthma chronic respiratory distress syndron
- ulcerative pain, psoriasis also used to treat gastropathy induced by nonsteroidal anti-inflammatory drugs (NSAID).
- NSAID nonsteroidal anti-inflammatory drugs
- the new compounds can also be used in combination with other active ingredients, e.g. B. with antiallergics, secretolytics,
- Antihistamines and / or PAF antagonists are included in the composition.
- Administration can be topical, oral, transdermal, nasal, parenteral or inhalative.
- the therapeutic or prophylactic dose is - apart from the potency of the individual compounds and the body weight of the patient - dependent on the nature and seriousness of the
- the new compounds can be administered topically, orally,
- compositions consisting essentially of an inert pharmaceutical carrier and a
- an effective dose of the active ingredient e.g. Tablets, coated tablets, capsules, wafers, powders, solutions, suspensions, inhalation aerosols, ointments, emulsions, syrups, suppositories, etc.
- An effective dose of the compounds according to the invention is oral
- Inhalation should be used in powders or solutions containing 0.5% to 5% active ingredient, with each dose containing approximately 2 to 20 mg active ingredient.
- the new compounds can be combined, inter alia, with antiallergics, secretolytics, ⁇ 2 -adrenergics, inhalable steroids or antihistamines.
- Active ingredient according to the invention 20 parts by weight
- the ingredients are processed in the usual way to tablets of 500 mg weight.
- the active ingredient content can be increased or decreased and the amount of glucose reduced or increased accordingly.
- Active ingredient according to the invention 100 parts by weight
- the ingredients are processed in the usual way into suppositories weighing 1.7 g.
- Micronized active ingredient powder (compound of formula I; particle size approx. 0.5 to 7 ⁇ m) is added in an amount of 5 mg, optionally with the addition of micronized lactose
- Bottled hard gelatin capsules The powder is inhaled from conventional inhalation devices, for example according to DE-A 3 345 722.
- the compounds of the invention were examined, inter alia, for their action in the tests below. a) LTB 4 receptor connection test
- U937 cells differentiated, human monocytic cell line with naturally expressed
- Concentration of the test substance is dose-dependent inhibited (incubation 2 h at 0 ° C).
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
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- Pain & Pain Management (AREA)
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Abstract
Description
Claims
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU63780/94A AU6378094A (en) | 1993-03-23 | 1994-03-18 | Heterocycle-containing amidine derivatives, their preparation and use |
JP6520657A JPH08508467A (en) | 1993-03-23 | 1994-03-18 | Amidine derivative containing heterocyclic group, method for producing the same and use thereof |
EP94911191A EP0690849A1 (en) | 1993-03-23 | 1994-03-18 | Heterocycle-containing amidine derivatives, their preparation and use |
SK1174-95A SK117495A3 (en) | 1993-03-23 | 1994-03-18 | Heterocycle containing amidine derivatives, their preparation and use |
KR1019950704014A KR960701026A (en) | 1993-03-23 | 1995-09-21 | Heterocycle-containing amidine derivatives, their preparation and use |
FI954491A FI954491A (en) | 1993-03-23 | 1995-09-22 | Heterocycles containing imidine derivatives, their preparation and use |
LVP-95-291A LV11465B (en) | 1993-03-23 | 1995-09-22 | Heterocycle-containing amidine derivatives, their preparation and use |
NO953763A NO953763L (en) | 1993-03-23 | 1995-09-22 | Heterocycle-containing amidine derivatives, their preparation and use |
BG100069A BG100069A (en) | 1993-03-23 | 1995-10-17 | Amidine derivatives containing heterocylic groups, their preparation and application |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4309285A DE4309285A1 (en) | 1993-03-23 | 1993-03-23 | Heterocyclic-containing amidine derivatives, their preparation and use |
DEP4309285.3 | 1993-03-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1994021616A1 true WO1994021616A1 (en) | 1994-09-29 |
Family
ID=6483550
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1994/000856 WO1994021616A1 (en) | 1993-03-23 | 1994-03-18 | Heterocycle-containing amidine derivatives, their preparation and use |
Country Status (18)
Country | Link |
---|---|
EP (1) | EP0690849A1 (en) |
JP (1) | JPH08508467A (en) |
KR (1) | KR960701026A (en) |
CN (1) | CN1124486A (en) |
AU (1) | AU6378094A (en) |
BG (1) | BG100069A (en) |
CA (1) | CA2158994A1 (en) |
CZ (1) | CZ246695A3 (en) |
DE (1) | DE4309285A1 (en) |
FI (1) | FI954491A (en) |
HU (1) | HUT73968A (en) |
IL (1) | IL109073A0 (en) |
LV (1) | LV11465B (en) |
NO (1) | NO953763L (en) |
PL (1) | PL310806A1 (en) |
SK (1) | SK117495A3 (en) |
WO (1) | WO1994021616A1 (en) |
ZA (1) | ZA941993B (en) |
Cited By (5)
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US6380259B2 (en) | 1997-12-12 | 2002-04-30 | Novartis Ag | Use of substituted amidino compounds in the treatment of chronic obstructive pulmonary disease |
US8030305B2 (en) | 2005-12-21 | 2011-10-04 | Janssen Pharmaceutica N.V. | Triazolopyridazines as kinase modulators |
US8178688B2 (en) | 2004-08-04 | 2012-05-15 | Dong Wha Pharmaceutical Co., Ltd. | Benzamidine derivatives, process for the preparation thereof and pharmaceutical composition comprising the same |
CN102993109A (en) * | 2012-12-03 | 2013-03-27 | 浙江工业大学 | Preparation method of amidine compound |
US9187439B2 (en) | 2011-09-21 | 2015-11-17 | Inception Orion, Inc. | Tricyclic compounds useful as neurogenic and neuroprotective agents |
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DE19546452A1 (en) * | 1995-12-13 | 1997-06-19 | Boehringer Ingelheim Kg | New phenylamidine derivatives, process for their preparation and their use as medicaments |
US20080200526A1 (en) * | 2004-07-05 | 2008-08-21 | Jin Soo Lee | Composition for the Prevention and Treatment of Allergic Inflammatory Disease |
TW200817410A (en) | 2006-08-07 | 2008-04-16 | Incyte Corp | Triazolotriazines as kinase inhibitors |
ME02372B (en) | 2006-11-22 | 2016-06-20 | Incyte Holdings Corp | Imidazotriazines and imidazopyrimidines as kinase inhibitors |
CN108586463A (en) | 2008-05-21 | 2018-09-28 | 因西特控股公司 | The salt of the fluoro- N- methyl -4- of 2- [7- (quinoline -6- ylmethyls) imidazo [1,2-b] [1,2,4] triazine -2- bases] benzamide and relative preparation method |
EP2531509B1 (en) | 2010-02-03 | 2016-10-05 | Incyte Holdings Corporation | Imidazo[1,2-b][1,2,4]triazines as c-met inhibitors |
KR101216274B1 (en) * | 2011-06-17 | 2012-12-28 | 이화여자대학교 산학협력단 | New compounds for alleviation, prevention or treatment of osteoporosis, the preparation thereof and pharmaceutical composition comprising the same |
WO2023144450A1 (en) * | 2022-01-28 | 2023-08-03 | Oulun Yliopisto | Compounds for use in the treatment of cancer and inflammatory conditions |
US11912675B1 (en) | 2023-10-11 | 2024-02-27 | King Faisal University | N'-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-3,4-dimethoxybenzimidamide as an antimicrobial compound |
US11919872B1 (en) | 2023-10-11 | 2024-03-05 | King Faisal University | N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)benzimidamide as an antimicrobial compound |
US11897850B1 (en) | 2023-10-11 | 2024-02-13 | King Faisal University | N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-4-methoxybenzimidamide as an antimicrobial compound |
US11976050B1 (en) | 2023-10-11 | 2024-05-07 | King Faisal University | N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)-1-naphthimidamide as an antimicrobial compound |
US11891366B1 (en) | 2023-10-12 | 2024-02-06 | King Faisal University | 4-methoxy-n′-(2-(5-phenyl-1,3,4-oxadiazol-2-ylthio)acetoxy)benzimidamide as an antimicrobial compound |
US11932632B1 (en) | 2023-10-13 | 2024-03-19 | King Faisal University | N'-(2-(5-phenyl-1,3,4-oxadiazol-2-ylthio)acetoxy)benzo[d][1,3]dioxole-5 carboximidamide as an antimicrobial compound |
US11999706B1 (en) | 2023-10-13 | 2024-06-04 | King Faisal University | 4-chloro-N′-(2-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-ylthio)acetoxy)benzimidamide as an antimicrobial compound |
US11905263B1 (en) | 2023-10-13 | 2024-02-20 | King Faisal University | 4-nitro-N′-(2-(5-phenyl-1,3,4-oxadiazol-2-ylthio)acetoxy)benzimidamide as an antimicrobial compound |
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GB868552A (en) * | 1957-12-03 | 1961-05-17 | Wellcome Found | Improvements in or relating to novel amidines and the preparation thereof |
DE3445691A1 (en) * | 1983-12-16 | 1985-07-04 | Torii & Co., Ltd., Tokio/Tokyo | AMIDINE DERIVATIVES, METHOD FOR THEIR PRODUCTION AND PHARMACEUTICAL AGENTS |
EP0292977A1 (en) * | 1987-05-29 | 1988-11-30 | G.D. Searle & Co. | Alkoxy-substituted dihydrobenzopyran-2-carboxylate derivatives |
EP0518818A2 (en) * | 1991-06-11 | 1992-12-16 | Ciba-Geigy Ag | Arylethers, their manufacture and use as medicament |
EP0518819A2 (en) * | 1991-06-11 | 1992-12-16 | Ciba-Geigy Ag | Amidino compounds, their manufacture and use as medicament |
EP0542363A2 (en) * | 1991-11-14 | 1993-05-19 | Glaxo Group Limited | Piperidineacetic acid derivatives as inhibitors of fibrinogen-dependent blood platelet aggregation |
WO1993016036A1 (en) * | 1992-02-05 | 1993-08-19 | Boehringer Ingelheim Kg | Novel amidine derivatives, their preparation and their use as mediaments with ltb-4 antagonistic effect |
-
1993
- 1993-03-23 DE DE4309285A patent/DE4309285A1/en not_active Withdrawn
-
1994
- 1994-03-18 CA CA002158994A patent/CA2158994A1/en not_active Abandoned
- 1994-03-18 HU HU9502778A patent/HUT73968A/en unknown
- 1994-03-18 PL PL94310806A patent/PL310806A1/en unknown
- 1994-03-18 WO PCT/EP1994/000856 patent/WO1994021616A1/en not_active Application Discontinuation
- 1994-03-18 JP JP6520657A patent/JPH08508467A/en active Pending
- 1994-03-18 SK SK1174-95A patent/SK117495A3/en unknown
- 1994-03-18 EP EP94911191A patent/EP0690849A1/en not_active Ceased
- 1994-03-18 CN CN94192207A patent/CN1124486A/en active Pending
- 1994-03-18 AU AU63780/94A patent/AU6378094A/en not_active Abandoned
- 1994-03-18 CZ CZ952466A patent/CZ246695A3/en unknown
- 1994-03-22 ZA ZA941993A patent/ZA941993B/en unknown
- 1994-03-22 IL IL10907394A patent/IL109073A0/en unknown
-
1995
- 1995-09-21 KR KR1019950704014A patent/KR960701026A/en not_active Application Discontinuation
- 1995-09-22 NO NO953763A patent/NO953763L/en unknown
- 1995-09-22 LV LVP-95-291A patent/LV11465B/en unknown
- 1995-09-22 FI FI954491A patent/FI954491A/en not_active Application Discontinuation
- 1995-10-17 BG BG100069A patent/BG100069A/en unknown
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GB868552A (en) * | 1957-12-03 | 1961-05-17 | Wellcome Found | Improvements in or relating to novel amidines and the preparation thereof |
DE3445691A1 (en) * | 1983-12-16 | 1985-07-04 | Torii & Co., Ltd., Tokio/Tokyo | AMIDINE DERIVATIVES, METHOD FOR THEIR PRODUCTION AND PHARMACEUTICAL AGENTS |
EP0292977A1 (en) * | 1987-05-29 | 1988-11-30 | G.D. Searle & Co. | Alkoxy-substituted dihydrobenzopyran-2-carboxylate derivatives |
EP0518818A2 (en) * | 1991-06-11 | 1992-12-16 | Ciba-Geigy Ag | Arylethers, their manufacture and use as medicament |
EP0518819A2 (en) * | 1991-06-11 | 1992-12-16 | Ciba-Geigy Ag | Amidino compounds, their manufacture and use as medicament |
EP0542363A2 (en) * | 1991-11-14 | 1993-05-19 | Glaxo Group Limited | Piperidineacetic acid derivatives as inhibitors of fibrinogen-dependent blood platelet aggregation |
WO1993016036A1 (en) * | 1992-02-05 | 1993-08-19 | Boehringer Ingelheim Kg | Novel amidine derivatives, their preparation and their use as mediaments with ltb-4 antagonistic effect |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6380259B2 (en) | 1997-12-12 | 2002-04-30 | Novartis Ag | Use of substituted amidino compounds in the treatment of chronic obstructive pulmonary disease |
US8178688B2 (en) | 2004-08-04 | 2012-05-15 | Dong Wha Pharmaceutical Co., Ltd. | Benzamidine derivatives, process for the preparation thereof and pharmaceutical composition comprising the same |
US8030305B2 (en) | 2005-12-21 | 2011-10-04 | Janssen Pharmaceutica N.V. | Triazolopyridazines as kinase modulators |
US8173654B2 (en) | 2005-12-21 | 2012-05-08 | Janssen Pharmaceutica N.V. | Triazolopyridazine compounds |
US9187439B2 (en) | 2011-09-21 | 2015-11-17 | Inception Orion, Inc. | Tricyclic compounds useful as neurogenic and neuroprotective agents |
CN102993109A (en) * | 2012-12-03 | 2013-03-27 | 浙江工业大学 | Preparation method of amidine compound |
Also Published As
Publication number | Publication date |
---|---|
NO953763L (en) | 1995-09-25 |
IL109073A0 (en) | 1994-06-24 |
CN1124486A (en) | 1996-06-12 |
HUT73968A (en) | 1996-10-28 |
JPH08508467A (en) | 1996-09-10 |
NO953763D0 (en) | 1995-09-22 |
ZA941993B (en) | 1994-09-23 |
DE4309285A1 (en) | 1994-09-29 |
CA2158994A1 (en) | 1994-09-29 |
HU9502778D0 (en) | 1995-11-28 |
CZ246695A3 (en) | 1996-02-14 |
EP0690849A1 (en) | 1996-01-10 |
FI954491A0 (en) | 1995-09-22 |
PL310806A1 (en) | 1996-01-08 |
BG100069A (en) | 1996-04-30 |
FI954491A (en) | 1995-09-22 |
SK117495A3 (en) | 1996-01-10 |
KR960701026A (en) | 1996-02-24 |
AU6378094A (en) | 1994-10-11 |
LV11465B (en) | 1996-12-20 |
LV11465A (en) | 1996-08-20 |
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