RU2017135541A - Гетероциклические амины и их применения - Google Patents
Гетероциклические амины и их применения Download PDFInfo
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- RU2017135541A RU2017135541A RU2017135541A RU2017135541A RU2017135541A RU 2017135541 A RU2017135541 A RU 2017135541A RU 2017135541 A RU2017135541 A RU 2017135541A RU 2017135541 A RU2017135541 A RU 2017135541A RU 2017135541 A RU2017135541 A RU 2017135541A
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- RU
- Russia
- Prior art keywords
- pyridin
- imidazo
- optionally substituted
- amino
- piperazin
- Prior art date
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- 150000001412 amines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 6
- 102000006940 Interleukin-1 Receptor-Associated Kinases Human genes 0.000 claims 5
- 108010072621 Interleukin-1 Receptor-Associated Kinases Proteins 0.000 claims 5
- -1 (6-cyanoimidazo [1,2-a] pyridin-2-yl) amino Chemical group 0.000 claims 4
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 3
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 3
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 208000017520 skin disease Diseases 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- UXIXQKWFZMRQAY-UHFFFAOYSA-N 1-[4-[[2-[(6-pyridin-3-ylimidazo[1,2-a]pyridin-2-yl)amino]pyridin-4-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC1=CC=NC(NC=2N=C3C=CC(=CN3C=2)C=2C=NC=CC=2)=C1 UXIXQKWFZMRQAY-UHFFFAOYSA-N 0.000 claims 1
- UVNOZNSJQYLLSG-UHFFFAOYSA-N 1-[4-[[2-[(6-pyridin-4-ylimidazo[1,2-a]pyridin-2-yl)amino]pyridin-4-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC1=CC=NC(NC=2N=C3C=CC(=CN3C=2)C=2C=CN=CC=2)=C1 UVNOZNSJQYLLSG-UHFFFAOYSA-N 0.000 claims 1
- HJIXHJQFJCYQFZ-UHFFFAOYSA-N 2-[[4-(hydroxymethyl)pyridin-2-yl]amino]imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound OCC1=CC=NC(NC=2N=C3C=CC(=CN3C=2)C#N)=C1 HJIXHJQFJCYQFZ-UHFFFAOYSA-N 0.000 claims 1
- CQSGRBXJPFLJTQ-UHFFFAOYSA-N 2-[[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]amino]imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C=1N2C=C(C#N)C=CC2=NC=1NC(N=CC=1)=CC=1CN1CCCC1 CQSGRBXJPFLJTQ-UHFFFAOYSA-N 0.000 claims 1
- HTTORECBYPSUCQ-UHFFFAOYSA-N 2-methoxy-1-[4-[2-[(6-pyridin-4-ylimidazo[1,2-a]pyridin-2-yl)amino]pyridin-4-yl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)COC)CCN1C1=CC=NC(NC=2N=C3C=CC(=CN3C=2)C=2C=CN=CC=2)=C1 HTTORECBYPSUCQ-UHFFFAOYSA-N 0.000 claims 1
- FQWGCMSZNAOHDT-UHFFFAOYSA-N 6-(1h-pyrazol-4-yl)-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]imidazo[1,2-a]pyridin-2-amine Chemical compound C=1C=NC(NC=2N=C3C=CC(=CN3C=2)C2=CNN=C2)=CC=1CN1CCCC1 FQWGCMSZNAOHDT-UHFFFAOYSA-N 0.000 claims 1
- NNYGUJKGXRYTKL-UHFFFAOYSA-N 6-pyridin-3-yl-n-[4-(pyrrolidin-1-ylmethyl)pyridin-2-yl]imidazo[1,2-a]pyridin-2-amine Chemical compound C=1C=NC(NC=2N=C3C=CC(=CN3C=2)C=2C=NC=CC=2)=CC=1CN1CCCC1 NNYGUJKGXRYTKL-UHFFFAOYSA-N 0.000 claims 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
- 206010001889 Alveolitis Diseases 0.000 claims 1
- 206010065452 Angiodermatitis Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 206010011224 Cough Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 206010014950 Eosinophilia Diseases 0.000 claims 1
- 206010015150 Erythema Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010028735 Nasal congestion Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000003251 Pruritus Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 206010040943 Skin Ulcer Diseases 0.000 claims 1
- 208000024780 Urticaria Diseases 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- 206010047115 Vasculitis Diseases 0.000 claims 1
- JLFXNCTUAAAIKM-UHFFFAOYSA-N [2-[(6-pyridin-3-ylimidazo[1,2-a]pyridin-2-yl)amino]pyridin-4-yl]methanol Chemical compound OCC1=CC=NC(NC=2N=C3C=CC(=CN3C=2)C=2C=NC=CC=2)=C1 JLFXNCTUAAAIKM-UHFFFAOYSA-N 0.000 claims 1
- XNNLWBHHLXXJGS-UHFFFAOYSA-N [2-[(6-pyridin-4-ylimidazo[1,2-a]pyridin-2-yl)amino]pyridin-4-yl]methanol Chemical compound OCC1=CC=NC(NC=2N=C3C=CC(=CN3C=2)C=2C=CN=CC=2)=C1 XNNLWBHHLXXJGS-UHFFFAOYSA-N 0.000 claims 1
- SQLFUDFJDSKYCD-UHFFFAOYSA-N [2-[[6-(1h-pyrazol-4-yl)imidazo[1,2-a]pyridin-2-yl]amino]pyridin-4-yl]methanol Chemical compound OCC1=CC=NC(NC=2N=C3C=CC(=CN3C=2)C2=CNN=C2)=C1 SQLFUDFJDSKYCD-UHFFFAOYSA-N 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 201000007717 corneal ulcer Diseases 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 231100000321 erythema Toxicity 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 201000001155 extrinsic allergic alveolitis Diseases 0.000 claims 1
- 208000022098 hypersensitivity pneumonitis Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 201000011486 lichen planus Diseases 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- HAEAXHNPMCKGNW-UHFFFAOYSA-N n-[4-(4-methylsulfonylpiperazin-1-yl)pyridin-2-yl]-6-(1h-pyrazol-4-yl)imidazo[1,2-a]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1C1=CC=NC(NC=2N=C3C=CC(=CN3C=2)C2=CNN=C2)=C1 HAEAXHNPMCKGNW-UHFFFAOYSA-N 0.000 claims 1
- SMBZKUOVUIECEC-UHFFFAOYSA-N n-[4-(4-methylsulfonylpiperazin-1-yl)pyridin-2-yl]-6-pyridin-4-ylimidazo[1,2-a]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1C1=CC=NC(NC=2N=C3C=CC(=CN3C=2)C=2C=CN=CC=2)=C1 SMBZKUOVUIECEC-UHFFFAOYSA-N 0.000 claims 1
- LYNMJHLIBHMSCM-UHFFFAOYSA-N n-[4-(piperazin-1-ylmethyl)pyridin-2-yl]-6-(1h-pyrazol-4-yl)imidazo[1,2-a]pyridin-2-amine Chemical compound C=1C=NC(NC=2N=C3C=CC(=CN3C=2)C2=CNN=C2)=CC=1CN1CCNCC1 LYNMJHLIBHMSCM-UHFFFAOYSA-N 0.000 claims 1
- YQNMCHMOOBVYAQ-UHFFFAOYSA-N n-[4-(piperazin-1-ylmethyl)pyridin-2-yl]-6-pyridin-4-ylimidazo[1,2-a]pyridin-2-amine Chemical compound C=1C=NC(NC=2N=C3C=CC(=CN3C=2)C=2C=CN=CC=2)=CC=1CN1CCNCC1 YQNMCHMOOBVYAQ-UHFFFAOYSA-N 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 208000015768 polyposis Diseases 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000008054 signal transmission Effects 0.000 claims 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
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- A61K31/5375—1,4-Oxazines, e.g. morpholine
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D269/00—Heterocyclic compounds containing rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms according to more than one of groups C07D261/00 - C07D267/00
- C07D269/02—Heterocyclic compounds containing rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms according to more than one of groups C07D261/00 - C07D267/00 having the hetero atoms in positions 1 and 3
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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- 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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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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- 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
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- C07D471/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
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- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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- C07D513/00—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
- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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2011
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