HU193799B - Process for producing 3-acyl-amino-methyl-imidazo-square bracket opened-1,2-a-square bracket closed-pyridine derivatives and pharmaceutical compositions containing them - Google Patents
Process for producing 3-acyl-amino-methyl-imidazo-square bracket opened-1,2-a-square bracket closed-pyridine derivatives and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- HU193799B HU193799B HU852991A HU299185A HU193799B HU 193799 B HU193799 B HU 193799B HU 852991 A HU852991 A HU 852991A HU 299185 A HU299185 A HU 299185A HU 193799 B HU193799 B HU 193799B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- compound
- methyl
- hydrogen
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 47
- 239000000460 chlorine Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- -1 methoxy, methylthio, ethylthio, methylsulfonyl Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229920002866 paraformaldehyde Polymers 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 230000002921 anti-spasmodic effect Effects 0.000 claims description 2
- 125000002785 azepinyl group Chemical group 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000000932 sedative agent Substances 0.000 claims description 2
- 230000001624 sedative effect Effects 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
- 206010029897 Obsessive thoughts Diseases 0.000 claims 2
- 125000006017 1-propenyl group Chemical group 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 241000700159 Rattus Species 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- IHXCPOUKJROXJU-UHFFFAOYSA-N 2-(4-chlorophenyl)-6-methylimidazo[1,2-a]pyridine Chemical compound C=1N2C=C(C)C=CC2=NC=1C1=CC=C(Cl)C=C1 IHXCPOUKJROXJU-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- XYGBKMMCQDZQOZ-UHFFFAOYSA-M sodium;4-hydroxybutanoate Chemical compound [Na+].OCCCC([O-])=O XYGBKMMCQDZQOZ-UHFFFAOYSA-M 0.000 description 4
- 206010053398 Clonic convulsion Diseases 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000003444 anaesthetic effect Effects 0.000 description 2
- 239000002249 anxiolytic agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000004622 sleep time Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- PJEXUIKBGBSHBS-UHFFFAOYSA-N 1-(hydroxymethyl)pyrrolidin-2-one Chemical compound OCN1CCCC1=O PJEXUIKBGBSHBS-UHFFFAOYSA-N 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- RFONJRMUUALMBA-UHFFFAOYSA-N 2-methanidylpropane Chemical compound CC(C)[CH2-] RFONJRMUUALMBA-UHFFFAOYSA-N 0.000 description 1
- KDHWCFCNNGUJCP-UHFFFAOYSA-N 2-phenylimidazo[1,2-a]pyridine Chemical class N1=C2C=CC=CN2C=C1C1=CC=CC=C1 KDHWCFCNNGUJCP-UHFFFAOYSA-N 0.000 description 1
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical class C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- QSHDDUUPEYYXMP-UHFFFAOYSA-N CC1=C(N2C(=C(N=C2C=C1)C3=CC=C(C=C3)Cl)C)N4CCCC4=O Chemical compound CC1=C(N2C(=C(N=C2C=C1)C3=CC=C(C=C3)Cl)C)N4CCCC4=O QSHDDUUPEYYXMP-UHFFFAOYSA-N 0.000 description 1
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 1
- 206010043994 Tonic convulsion Diseases 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- CPYGBGOXCJJJGC-GKLGUMFISA-L alcuronium chloride Chemical compound [Cl-].[Cl-].C/1([C@@H]23)=C\N([C@H]4\5)C6=CC=CC=C6[C@]4(CC[N@@+]4(CC=C)C\C6=C\CO)[C@@H]4C[C@@H]6C/5=C/N3C3=CC=CC=C3[C@@]22CC[N@@+]3(CC=C)C/C(=C/CO)[C@@H]\1C[C@H]32 CPYGBGOXCJJJGC-GKLGUMFISA-L 0.000 description 1
- 230000036626 alertness Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 238000002690 local anesthesia Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- UOUBPDZUBVJZOQ-UHFFFAOYSA-N n-(hydroxymethyl)benzamide Chemical compound OCNC(=O)C1=CC=CC=C1 UOUBPDZUBVJZOQ-UHFFFAOYSA-N 0.000 description 1
- KZQXMTDYABQGLL-UHFFFAOYSA-N n-[[2-(4-chlorophenyl)-6-methylimidazo[1,2-a]pyridin-3-yl]methyl]-2-methylpropanamide Chemical compound N1=C2C=CC(C)=CN2C(CNC(=O)C(C)C)=C1C1=CC=C(Cl)C=C1 KZQXMTDYABQGLL-UHFFFAOYSA-N 0.000 description 1
- YWDPEPUZYVNESQ-UHFFFAOYSA-N n-[[2-(4-chlorophenyl)-6-methylimidazo[1,2-a]pyridin-3-yl]methyl]benzamide Chemical compound N12C=C(C)C=CC2=NC(C=2C=CC(Cl)=CC=2)=C1CNC(=O)C1=CC=CC=C1 YWDPEPUZYVNESQ-UHFFFAOYSA-N 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 210000001331 nose Anatomy 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 230000036387 respiratory rate Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 210000003625 skull Anatomy 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 208000009999 tuberous sclerosis Diseases 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229940072358 xylocaine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8412447A FR2568880B1 (fr) | 1984-08-07 | 1984-08-07 | Derives d'acylaminomethyl-3 imidazo(1,2-a)pyridines, leur preparation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT38637A HUT38637A (en) | 1986-06-30 |
| HU193799B true HU193799B (en) | 1987-11-30 |
Family
ID=9306856
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU852991A HU193799B (en) | 1984-08-07 | 1985-08-06 | Process for producing 3-acyl-amino-methyl-imidazo-square bracket opened-1,2-a-square bracket closed-pyridine derivatives and pharmaceutical compositions containing them |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4650796A (OSRAM) |
| EP (1) | EP0172096B1 (OSRAM) |
| JP (1) | JPS6147485A (OSRAM) |
| KR (1) | KR910004450B1 (OSRAM) |
| AR (1) | AR241185A1 (OSRAM) |
| AT (1) | ATE40365T1 (OSRAM) |
| AU (1) | AU575190B2 (OSRAM) |
| CA (1) | CA1261830A (OSRAM) |
| CZ (1) | CZ357691A3 (OSRAM) |
| DE (1) | DE3567867D1 (OSRAM) |
| DK (1) | DK163923C (OSRAM) |
| ES (1) | ES8604592A1 (OSRAM) |
| FI (1) | FI80696C (OSRAM) |
| FR (1) | FR2568880B1 (OSRAM) |
| GR (1) | GR851928B (OSRAM) |
| HU (1) | HU193799B (OSRAM) |
| IE (1) | IE58347B1 (OSRAM) |
| IL (1) | IL76020A (OSRAM) |
| MX (1) | MX160845A (OSRAM) |
| NO (1) | NO162189C (OSRAM) |
| NZ (1) | NZ213013A (OSRAM) |
| PT (1) | PT80921B (OSRAM) |
| ZA (1) | ZA855939B (OSRAM) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3769333D1 (de) * | 1986-01-22 | 1991-05-23 | Synthelabo | Acylaminomethylimidazo(1,2-a)pyrimidinderivate, ihre herstellung und therapeutische verwendung. |
| FR2593818B1 (fr) * | 1986-02-05 | 1988-04-29 | Synthelabo | Derives d'acylaminomethyl-3 imidazo(1,2-a)pyridine, leur preparation et leur application en therapeutique |
| FR2593180B1 (fr) * | 1986-01-22 | 1990-10-26 | Synthelabo | Derives d'acylaminomethyl-1 imidazo (1,2-a)quinoleines, leur preparation et leur application en therapeutique |
| US4990506A (en) * | 1986-02-05 | 1991-02-05 | Synthelabo | 3-(acylaminomethyl)imidazo[1,2-a]pyridine derivatives and their application in therapy |
| FR2606409B1 (fr) * | 1986-11-07 | 1989-05-05 | Synthelabo | Derives d'imidazopyridine, leur preparation et leur application en therapeutique |
| ES2026666T3 (es) * | 1987-03-27 | 1992-05-01 | Synthelabo | Procedimiento para preparar derivados de imidazopiridinas. |
| FR2615513B1 (fr) * | 1987-05-21 | 1989-07-13 | Synthelabo | Derives d'acylaminomethyl-3 tetrahydro-5,6,7,8 imidazo(1,2-a)pyridines, leur preparation et leur application en therapeutique |
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| JP2007509960A (ja) * | 2003-10-28 | 2007-04-19 | セプラコア インコーポレーテッド | イミダゾ［１，２−ａ］ピリジン抗不安薬 |
| WO2005081749A2 (en) * | 2004-01-23 | 2005-09-09 | Avanir Pharmaceuticals, Inc. | Neutralizing human antibodies to anthraxtoxin |
| FR2874611B1 (fr) * | 2004-08-31 | 2006-11-17 | Servier Lab | Nouveaux derives d'imidazopyridine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| EP1814880B1 (en) * | 2004-11-11 | 2009-01-28 | Ferrer Internacional, S.A. | Imidazo[1,2-a]pyridine compounds, compositions, uses and methods related thereto |
| ES2441178T3 (es) | 2005-06-01 | 2014-02-03 | Ucb Pharma, S.A. | Derivados de 2-oxo-1-pirrolidina, procedimientos para prepararlos y el uso terapéutico de los mismos sobre el sistema nervioso central |
| EP2152262A2 (en) * | 2007-04-27 | 2010-02-17 | UCB Pharma, S.A. | New heterocyclic derivatives useful for the treatment of cns disorders |
| WO2009143156A2 (en) * | 2008-05-19 | 2009-11-26 | Sepracor Inc. | IMIDAZO[1,2-a]PYRIDINE COMPOUNDS |
| DK2376490T3 (da) * | 2008-12-04 | 2013-04-15 | Proximagen Ltd | Imidazopyridinforbindelser |
| SG11201509650YA (en) | 2013-05-24 | 2015-12-30 | Iomet Pharma Ltd | Slc2a transporter inhibitors |
| US12282014B2 (en) | 2015-11-19 | 2025-04-22 | Dana-Farber Cancer Institute, Inc. | Methods of identifying compounds that interfere with ERG-driven misguidance of BAF complexes in TMPRSS2-ERG driven prostate cancers |
| EP3746124A4 (en) | 2018-01-30 | 2021-10-27 | Foghorn Therapeutics Inc. | COMPOUNDS AND THEIR USES |
| US12473334B2 (en) | 2018-10-17 | 2025-11-18 | Dana-Farber Cancer Institute, Inc. | SWI/SNF family chromatin remodeling complexes and uses thereof |
| JP2022515879A (ja) * | 2018-12-29 | 2022-02-22 | 武漢朗来科技発展有限公司 | 複素環式化合物、中間体、その製造方法及び応用 本願は、出願日が２０１８年１２月２９日の中国特許出願ｃｎ ２０１８１１６４２３１９、出願日が２０１９年０５月２４日の中国特許出願ｃｎ２０１９１０４４０２１４．３及び出願日が２０１９年１０月２４日の中国特許出願ｃｎ２０１９１１０１６１５８．７に基づいて優先権を主張する。また、上記中国特許出願の全文は本願に援用される。 |
| WO2020160196A1 (en) | 2019-01-29 | 2020-08-06 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| BR112022015004A2 (pt) | 2020-01-29 | 2022-09-20 | Foghorn Therapeutics Inc | Composto, composição farmacêutica, métodos para diminuir a atividade de um complexo baf, induzir apoptose, reduzir o crescimento tumoral, suprimir a progressão e a colonização metastática do câncer e reduzir o nível e/ou a atividade de brg1 e/ou brm em um câncer e métodos de tratamento e de inibição de brm e brg1 |
| EP4096668A4 (en) * | 2020-01-29 | 2024-02-28 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
| US12383555B2 (en) | 2020-05-20 | 2025-08-12 | Foghorn Therapeutics Inc. | Methods of treating cancers |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB991589A (en) * | 1963-04-30 | 1965-05-12 | Selvi & C Lab Bioterapico | Novel [1,2-ª‡]imidazopyridines and a process for the manufacture thereof |
| GB1076089A (en) * | 1965-11-09 | 1967-07-19 | Selvi & C Lab Bioterapico | New derivatives of imidazo [1,2-a]-pyridine and a process for the manufacture thereof |
-
1984
- 1984-08-07 FR FR8412447A patent/FR2568880B1/fr not_active Expired
-
1985
- 1985-07-30 DE DE8585401554T patent/DE3567867D1/de not_active Expired
- 1985-07-30 AT AT85401554T patent/ATE40365T1/de not_active IP Right Cessation
- 1985-07-30 EP EP85401554A patent/EP0172096B1/fr not_active Expired
- 1985-08-06 GR GR851928A patent/GR851928B/el unknown
- 1985-08-06 ES ES545928A patent/ES8604592A1/es not_active Expired
- 1985-08-06 HU HU852991A patent/HU193799B/hu not_active IP Right Cessation
- 1985-08-06 PT PT80921A patent/PT80921B/pt not_active IP Right Cessation
- 1985-08-06 ZA ZA855939A patent/ZA855939B/xx unknown
- 1985-08-06 IE IE193785A patent/IE58347B1/en not_active IP Right Cessation
- 1985-08-06 AU AU45809/85A patent/AU575190B2/en not_active Ceased
- 1985-08-06 NZ NZ213013A patent/NZ213013A/en unknown
- 1985-08-06 MX MX206217A patent/MX160845A/es unknown
- 1985-08-06 NO NO853100A patent/NO162189C/no unknown
- 1985-08-06 IL IL76020A patent/IL76020A/xx not_active IP Right Cessation
- 1985-08-06 FI FI853026A patent/FI80696C/fi not_active IP Right Cessation
- 1985-08-06 AR AR85301203A patent/AR241185A1/es active
- 1985-08-06 JP JP60173977A patent/JPS6147485A/ja active Granted
- 1985-08-06 KR KR1019850005660A patent/KR910004450B1/ko not_active Expired
- 1985-08-06 DK DK356885A patent/DK163923C/da not_active IP Right Cessation
- 1985-08-06 CA CA000488165A patent/CA1261830A/en not_active Expired
-
1986
- 1986-02-07 US US06/826,966 patent/US4650796A/en not_active Expired - Lifetime
-
1991
- 1991-11-25 CZ CS913576A patent/CZ357691A3/cs unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |