MX2015002026A - Nuevos derivados de piridina. - Google Patents
Nuevos derivados de piridina.Info
- Publication number
- MX2015002026A MX2015002026A MX2015002026A MX2015002026A MX2015002026A MX 2015002026 A MX2015002026 A MX 2015002026A MX 2015002026 A MX2015002026 A MX 2015002026A MX 2015002026 A MX2015002026 A MX 2015002026A MX 2015002026 A MX2015002026 A MX 2015002026A
- Authority
- MX
- Mexico
- Prior art keywords
- chloro
- pyridin
- cyclopropanecarbonyl
- amide
- pyrrolidine
- Prior art date
Links
- 150000003222 pyridines Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 133
- 239000003814 drug Substances 0.000 claims abstract description 7
- -1 [1,2,3] -triazolyl Chemical group 0.000 claims description 291
- UIVATUPCWVUVIM-UHFFFAOYSA-N 1-aminocyclopropane-1-carbonitrile Chemical compound N#CC1(N)CC1 UIVATUPCWVUVIM-UHFFFAOYSA-N 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 201000001320 Atherosclerosis Diseases 0.000 claims description 17
- 150000002367 halogens Chemical group 0.000 claims description 15
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 206010012601 diabetes mellitus Diseases 0.000 claims description 10
- 238000011321 prophylaxis Methods 0.000 claims description 10
- 206010002329 Aneurysm Diseases 0.000 claims description 9
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 9
- 208000005764 Peripheral Arterial Disease Diseases 0.000 claims description 9
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 9
- 210000000702 aorta abdominal Anatomy 0.000 claims description 9
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000007822 coupling agent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 3
- MAQAGRJURDEYDQ-UHFFFAOYSA-N 6-methylpyridine Chemical compound CC1=C=CC=C[N]1 MAQAGRJURDEYDQ-UHFFFAOYSA-N 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- FENLDWYGLWOJRX-RISCZKNCSA-N (2s,4r)-1-[1-(5-chloro-3-fluoropyridin-2-yl)cyclopropanecarbonyl]-4-(3-chloropyridin-2-yl)sulfonylpyrrolidine-2-carboxylic acid Chemical compound C([C@@H](C[C@H]1C(=O)O)S(=O)(=O)C=2C(=CC=CN=2)Cl)N1C(=O)C1(C=2C(=CC(Cl)=CN=2)F)CC1 FENLDWYGLWOJRX-RISCZKNCSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 description 39
- 239000011541 reaction mixture Substances 0.000 description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 31
- 108090000613 Cathepsin S Proteins 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
- 102100035654 Cathepsin S Human genes 0.000 description 27
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 239000006260 foam Substances 0.000 description 17
- 239000013058 crude material Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 12
- 108090000624 Cathepsin L Proteins 0.000 description 11
- 102000004172 Cathepsin L Human genes 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 230000009467 reduction Effects 0.000 description 11
- 102000005600 Cathepsins Human genes 0.000 description 10
- 108010084457 Cathepsins Proteins 0.000 description 10
- 238000002953 preparative HPLC Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 208000020832 chronic kidney disease Diseases 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- 102000005927 Cysteine Proteases Human genes 0.000 description 8
- 108010005843 Cysteine Proteases Proteins 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 7
- 206010028980 Neoplasm Diseases 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 201000011510 cancer Diseases 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 6
- 239000007821 HATU Substances 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007832 Na2SO4 Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002671 adjuvant Substances 0.000 description 6
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 6
- 230000007211 cardiovascular event Effects 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 230000002950 deficient Effects 0.000 description 6
- 150000002431 hydrogen Chemical group 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 5
- KLDLRDSRCMJKGM-UHFFFAOYSA-N 3-[chloro-(2-oxo-1,3-oxazolidin-3-yl)phosphoryl]-1,3-oxazolidin-2-one Chemical compound C1COC(=O)N1P(=O)(Cl)N1CCOC1=O KLDLRDSRCMJKGM-UHFFFAOYSA-N 0.000 description 5
- PERMDYZFNQIKBL-UHFFFAOYSA-N 5-chloro-2,3-difluoropyridine Chemical compound FC1=CC(Cl)=CN=C1F PERMDYZFNQIKBL-UHFFFAOYSA-N 0.000 description 5
- 102000035195 Peptidases Human genes 0.000 description 5
- 108091005804 Peptidases Proteins 0.000 description 5
- 239000004365 Protease Substances 0.000 description 5
- 239000012317 TBTU Substances 0.000 description 5
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 5
- 230000003143 atherosclerotic effect Effects 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 230000003246 elastolytic effect Effects 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
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- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 4
- 206010012689 Diabetic retinopathy Diseases 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 230000007812 deficiency Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 208000002780 macular degeneration Diseases 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 3
- AMZIIVAMNBOGAH-UHFFFAOYSA-N 1-(3-fluoro-5-iodopyridin-2-yl)cyclopropane-1-carboxylic acid Chemical compound N=1C=C(I)C=C(F)C=1C1(C(=O)O)CC1 AMZIIVAMNBOGAH-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- 208000037260 Atherosclerotic Plaque Diseases 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
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- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 3
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- 239000001828 Gelatine Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 208000034827 Neointima Diseases 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 230000030741 antigen processing and presentation Effects 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
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- 238000006731 degradation reaction Methods 0.000 description 3
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- 229940079593 drug Drugs 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 3
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- PDNCLRISYVUREF-UHFFFAOYSA-N 1-(5-chloro-3-fluoropyridin-2-yl)cyclopropane-1-carboxylic acid Chemical compound N=1C=C(Cl)C=C(F)C=1C1(C(=O)O)CC1 PDNCLRISYVUREF-UHFFFAOYSA-N 0.000 description 2
- FOQJHZPURACERJ-UHFFFAOYSA-N 2,4,4,5,5-pentamethyl-1,3,2-dioxaborolane Chemical compound CB1OC(C)(C)C(C)(C)O1 FOQJHZPURACERJ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- CLJUYSUDVRFKEL-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)benzenethiol Chemical compound FC(F)(F)C1=CC=C(Cl)C(S)=C1 CLJUYSUDVRFKEL-UHFFFAOYSA-N 0.000 description 2
- WJTZZPVVTSDNJJ-UHFFFAOYSA-N 2-fluorobenzenethiol Chemical compound FC1=CC=CC=C1S WJTZZPVVTSDNJJ-UHFFFAOYSA-N 0.000 description 2
- MBTULFIFECUURA-UHFFFAOYSA-N 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound C1=NC(C)=CC(B2OC(C)(C)C(C)(C)O2)=C1 MBTULFIFECUURA-UHFFFAOYSA-N 0.000 description 2
- ACGSRAAAQJSWLC-UHFFFAOYSA-N 3-(trifluoromethyl)-1h-pyridine-2-thione Chemical compound FC(F)(F)C1=CC=CN=C1S ACGSRAAAQJSWLC-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- VZQDBNWKBKWCFJ-UHFFFAOYSA-N 4-bromo-2-chlorobenzenethiol Chemical compound SC1=CC=C(Br)C=C1Cl VZQDBNWKBKWCFJ-UHFFFAOYSA-N 0.000 description 2
- PXACTUVBBMDKRW-UHFFFAOYSA-M 4-bromobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-M 0.000 description 2
- SPXOTSHWBDUUMT-UHFFFAOYSA-M 4-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=C(S([O-])(=O)=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-M 0.000 description 2
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/08—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 linked by a carbon chain containing alicyclic rings
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D401/14—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 three or more hetero rings
Landscapes
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- Cardiology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12181247 | 2012-08-21 | ||
| PCT/EP2013/067218 WO2014029722A1 (en) | 2012-08-21 | 2013-08-19 | Novel pyridine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2015002026A true MX2015002026A (es) | 2015-06-05 |
Family
ID=46851300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2015002026A MX2015002026A (es) | 2012-08-21 | 2013-08-19 | Nuevos derivados de piridina. |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US9409882B2 (enExample) |
| EP (1) | EP2888244A1 (enExample) |
| JP (1) | JP2015530997A (enExample) |
| KR (1) | KR20150044947A (enExample) |
| CN (1) | CN104583198A (enExample) |
| AR (1) | AR092172A1 (enExample) |
| AU (1) | AU2013305102A1 (enExample) |
| BR (1) | BR112015003217A2 (enExample) |
| CA (1) | CA2879796A1 (enExample) |
| CL (1) | CL2015000354A1 (enExample) |
| CO (1) | CO7200259A2 (enExample) |
| CR (1) | CR20150073A (enExample) |
| EA (1) | EA025166B1 (enExample) |
| HK (1) | HK1206716A1 (enExample) |
| IL (1) | IL237128A0 (enExample) |
| IN (1) | IN2015DN00962A (enExample) |
| MA (1) | MA37893A1 (enExample) |
| MX (1) | MX2015002026A (enExample) |
| PE (1) | PE20150995A1 (enExample) |
| PH (1) | PH12015500262A1 (enExample) |
| SG (1) | SG11201500900YA (enExample) |
| TW (1) | TW201412728A (enExample) |
| WO (1) | WO2014029722A1 (enExample) |
| ZA (1) | ZA201500625B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI3419970T1 (sl) * | 2016-02-26 | 2020-04-30 | F. Hoffmann-La Roche Ag | Novi pirolidinski derivati |
| TWI764976B (zh) | 2017-01-24 | 2022-05-21 | 日商安斯泰來製藥股份有限公司 | 取代苯基二氟甲基之脯胺酸醯胺化合物 |
| WO2026032128A1 (en) * | 2024-08-05 | 2026-02-12 | Biofront Therapeutics (Beijing) Co., Ltd. | Cathepsin l inhibitors |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9903610D0 (sv) | 1999-10-06 | 1999-10-06 | Astra Ab | Novel compounds II |
| WO2006073361A1 (en) | 2005-01-06 | 2006-07-13 | Astrazeneca Ab | Novel pyridine compounds |
| CN101370805B (zh) | 2006-01-24 | 2011-04-27 | 埃科特莱茵药品有限公司 | 吡啶衍生物 |
| EP2164840A2 (en) * | 2007-05-09 | 2010-03-24 | Vertex Pharmaceuticals Incorporated | Modulators of cftr |
| BRPI0820203A2 (pt) | 2007-11-30 | 2015-06-16 | Hoffmann La Roche | Compostos de pirrdina, processo para a sua preparação, composição farmacêutica que os compreende, uso de composto e método para o tratamento e/ou profilaxia de diabetes mellitus do tipo ii e outras enfermidades |
| CN101965345B (zh) | 2008-03-06 | 2014-05-28 | 埃科特莱茵药品有限公司 | 吡啶化合物 |
| MX2011011094A (es) | 2009-04-20 | 2011-11-04 | Hoffmann La Roche | Derivados de prolina como inhibidores de catepsina. |
| US8394834B2 (en) * | 2009-08-25 | 2013-03-12 | Hoffman-La Roche Inc. | Pyrrolidines as NK3 receptor antagonists |
| JP6130383B2 (ja) | 2011-09-30 | 2017-05-17 | エンドゥ ファーマシューティカルズ，インコーポレイティド | ピリジン誘導体 |
-
2013
- 2013-08-19 SG SG11201500900YA patent/SG11201500900YA/en unknown
- 2013-08-19 IN IN962DEN2015 patent/IN2015DN00962A/en unknown
- 2013-08-19 TW TW102129708A patent/TW201412728A/zh unknown
- 2013-08-19 EP EP13750339.7A patent/EP2888244A1/en not_active Withdrawn
- 2013-08-19 HK HK15107145.2A patent/HK1206716A1/xx unknown
- 2013-08-19 BR BR112015003217A patent/BR112015003217A2/pt not_active Application Discontinuation
- 2013-08-19 MA MA37893A patent/MA37893A1/fr unknown
- 2013-08-19 PE PE2015000231A patent/PE20150995A1/es not_active Application Discontinuation
- 2013-08-19 CN CN201380043572.1A patent/CN104583198A/zh active Pending
- 2013-08-19 CA CA2879796A patent/CA2879796A1/en not_active Abandoned
- 2013-08-19 EA EA201590363A patent/EA025166B1/ru not_active IP Right Cessation
- 2013-08-19 MX MX2015002026A patent/MX2015002026A/es unknown
- 2013-08-19 KR KR20157006927A patent/KR20150044947A/ko not_active Withdrawn
- 2013-08-19 AU AU2013305102A patent/AU2013305102A1/en not_active Abandoned
- 2013-08-19 JP JP2015527877A patent/JP2015530997A/ja active Pending
- 2013-08-19 WO PCT/EP2013/067218 patent/WO2014029722A1/en not_active Ceased
- 2013-08-20 AR ARP130102939A patent/AR092172A1/es unknown
-
2015
- 2015-01-27 ZA ZA2015/00625A patent/ZA201500625B/en unknown
- 2015-02-05 IL IL237128A patent/IL237128A0/en unknown
- 2015-02-06 PH PH12015500262A patent/PH12015500262A1/en unknown
- 2015-02-09 CO CO15025964A patent/CO7200259A2/es unknown
- 2015-02-11 CR CR20150073A patent/CR20150073A/es not_active Application Discontinuation
- 2015-02-16 CL CL2015000354A patent/CL2015000354A1/es unknown
- 2015-02-20 US US14/627,175 patent/US9409882B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR20150044947A (ko) | 2015-04-27 |
| PE20150995A1 (es) | 2015-06-29 |
| US20150307472A1 (en) | 2015-10-29 |
| CO7200259A2 (es) | 2015-02-27 |
| MA37893A1 (fr) | 2017-08-31 |
| IN2015DN00962A (enExample) | 2015-06-12 |
| EA201590363A1 (ru) | 2015-06-30 |
| IL237128A0 (en) | 2015-03-31 |
| TW201412728A (zh) | 2014-04-01 |
| CA2879796A1 (en) | 2014-02-27 |
| SG11201500900YA (en) | 2015-03-30 |
| CN104583198A (zh) | 2015-04-29 |
| EA025166B1 (ru) | 2016-11-30 |
| AU2013305102A1 (en) | 2015-02-12 |
| EP2888244A1 (en) | 2015-07-01 |
| CL2015000354A1 (es) | 2015-10-23 |
| US9409882B2 (en) | 2016-08-09 |
| AR092172A1 (es) | 2015-03-25 |
| HK1206716A1 (en) | 2016-01-15 |
| ZA201500625B (en) | 2016-08-31 |
| JP2015530997A (ja) | 2015-10-29 |
| BR112015003217A2 (pt) | 2017-07-04 |
| CR20150073A (es) | 2015-03-13 |
| PH12015500262A1 (en) | 2015-03-30 |
| WO2014029722A1 (en) | 2014-02-27 |
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