TW200946524A - Certain chemical entities, compositions and methods - Google Patents

Info

Publication number

TW200946524A

TW200946524A TW098103382A TW98103382A TW200946524A TW 200946524 A TW200946524 A TW 200946524A TW 098103382 A TW098103382 A TW 098103382A TW 98103382 A TW98103382 A TW 98103382A TW 200946524 A TW200946524 A TW 200946524A

Authority

TW

Taiwan

Prior art keywords

chloro

group

ethylpropyl

imidazo

pyridin

Prior art date

2008-02-04

Links

• Espacenet
• Global Dossier
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• 238000000034 method Methods 0.000 title claims abstract description 39
• 239000000203 mixture Substances 0.000 title claims description 49
• 150000005829 chemical entities Chemical class 0.000 title abstract 2
• 210000002027 skeletal muscle Anatomy 0.000 claims abstract description 45
• 108060008487 Myosin Proteins 0.000 claims abstract description 35
• 102000003505 Myosin Human genes 0.000 claims abstract description 35
• 102000007469 Actins Human genes 0.000 claims abstract description 22
• 108010085238 Actins Proteins 0.000 claims abstract description 22
• 238000011282 treatment Methods 0.000 claims abstract description 21
• 210000002235 sarcomere Anatomy 0.000 claims abstract description 14
• 206010028289 Muscle atrophy Diseases 0.000 claims abstract description 13
• 201000000585 muscular atrophy Diseases 0.000 claims abstract description 13
• 206010049565 Muscle fatigue Diseases 0.000 claims abstract description 9
• 230000020763 muscle atrophy Effects 0.000 claims abstract description 9
• 108090000362 Lymphotoxin-beta Proteins 0.000 claims abstract description 8
• 208000001145 Metabolic Syndrome Diseases 0.000 claims abstract description 8
• 102000013534 Troponin C Human genes 0.000 claims abstract description 8
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims abstract description 8
• 208000018360 neuromuscular disease Diseases 0.000 claims abstract description 7
• 102000013394 Troponin I Human genes 0.000 claims abstract description 3
• 108010065729 Troponin I Proteins 0.000 claims abstract description 3
• 206010022562 Intermittent claudication Diseases 0.000 claims abstract 2
• 208000024980 claudication Diseases 0.000 claims abstract 2
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 189
• 125000000217 alkyl group Chemical group 0.000 claims description 130
• -1 methoxy, methyl Chemical group 0.000 claims description 124
• 239000000126 substance Substances 0.000 claims description 100
• 150000001875 compounds Chemical class 0.000 claims description 87
• 210000003205 muscle Anatomy 0.000 claims description 75
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
• 125000001072 heteroaryl group Chemical group 0.000 claims description 57
• 229910052739 hydrogen Inorganic materials 0.000 claims description 46
• 239000001257 hydrogen Substances 0.000 claims description 46
• 229910052799 carbon Inorganic materials 0.000 claims description 44
• 210000000988 bone and bone Anatomy 0.000 claims description 42
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 39
• 210000001087 myotubule Anatomy 0.000 claims description 38
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 34
• 150000003839 salts Chemical class 0.000 claims description 34
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 33
• 201000010099 disease Diseases 0.000 claims description 33
• VUZCWTUAXNDZSX-UHFFFAOYSA-N acridin-2-ol Chemical compound C1=CC=CC2=CC3=CC(O)=CC=C3N=C21 VUZCWTUAXNDZSX-UHFFFAOYSA-N 0.000 claims description 32
• 125000003118 aryl group Chemical group 0.000 claims description 32
• 239000007789 gas Substances 0.000 claims description 29
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 29
• 125000005843 halogen group Chemical group 0.000 claims description 28
• 150000002431 hydrogen Chemical group 0.000 claims description 27
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 27
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 24
• 125000004093 cyano group Chemical class *C#N 0.000 claims description 23
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 21
• 102000004903 Troponin Human genes 0.000 claims description 20
• 108090001027 Troponin Proteins 0.000 claims description 20
• 125000003277 amino group Chemical group 0.000 claims description 20
• 125000003107 substituted aryl group Chemical group 0.000 claims description 20
• 125000004076 pyridyl group Chemical group 0.000 claims description 19
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 18
• 230000001965 increasing effect Effects 0.000 claims description 18
• 239000002253 acid Substances 0.000 claims description 16
• BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 16
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
• 102000004169 proteins and genes Human genes 0.000 claims description 16
• 108090000623 proteins and genes Proteins 0.000 claims description 16
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 16
• 230000027455 binding Effects 0.000 claims description 15
• 230000000694 effects Effects 0.000 claims description 15
• 239000000835 fiber Substances 0.000 claims description 15
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 15
• BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 14
• 229910001424 calcium ion Inorganic materials 0.000 claims description 14
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
• 239000011737 fluorine Substances 0.000 claims description 13
• 229910052731 fluorine Inorganic materials 0.000 claims description 13
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
• 241000209094 Oryza Species 0.000 claims description 12
• 235000007164 Oryza sativa Nutrition 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 150000002500 ions Chemical class 0.000 claims description 12
• 235000009566 rice Nutrition 0.000 claims description 12
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 12
• 235000019640 taste Nutrition 0.000 claims description 12
• 239000000460 chlorine Substances 0.000 claims description 11
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 150000003573 thiols Chemical group 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
• 150000001412 amines Chemical class 0.000 claims description 9
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 210000003296 saliva Anatomy 0.000 claims description 9
• GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 8
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 8
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 7
• WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 7
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 7
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
• 244000294411 Mirabilis expansa Species 0.000 claims description 6
• 235000015429 Mirabilis expansa Nutrition 0.000 claims description 6
• 235000013536 miso Nutrition 0.000 claims description 6
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 230000004044 response Effects 0.000 claims description 6
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
• 150000001721 carbon Chemical class 0.000 claims description 5
• 150000002923 oximes Chemical class 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 125000001153 fluoro group Chemical group F* 0.000 claims description 4
• 150000002460 imidazoles Chemical class 0.000 claims description 4
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 239000002689 soil Substances 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
• 125000000524 functional group Chemical group 0.000 claims description 3
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
• 230000035945 sensitivity Effects 0.000 claims description 3
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• 239000000052 vinegar Substances 0.000 claims description 3
• 235000021419 vinegar Nutrition 0.000 claims description 3
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
• 208000029578 Muscle disease Diseases 0.000 claims description 2
• 239000005864 Sulphur Substances 0.000 claims description 2
• 125000003342 alkenyl group Chemical group 0.000 claims description 2
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
• 229910052794 bromium Inorganic materials 0.000 claims description 2
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• 150000002367 halogens Chemical group 0.000 claims description 2
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
• 239000001294 propane Substances 0.000 claims description 2
• 230000001235 sensitizing effect Effects 0.000 claims description 2
• 239000007921 spray Substances 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 5
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims 4
• 230000002708 enhancing effect Effects 0.000 claims 3
• DANLZOIRUUHIIX-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F DANLZOIRUUHIIX-UHFFFAOYSA-N 0.000 claims 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims 2
• 125000001041 indolyl group Chemical group 0.000 claims 2
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
• 125000003944 tolyl group Chemical group 0.000 claims 2
• FESCOPRULBSKEL-UHFFFAOYSA-N 1-sulfanylpropane-1,3-diol Chemical compound OCCC(O)S FESCOPRULBSKEL-UHFFFAOYSA-N 0.000 claims 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 1
• QXEFZHFOEXCGGS-UHFFFAOYSA-N 2-(6-chloro-2-oxo-1-pentan-3-yl-3h-imidazo[4,5-b]pyridin-7-yl)benzamide Chemical compound ClC1=CN=C2NC(=O)N(C(CC)CC)C2=C1C1=CC=CC=C1C(N)=O QXEFZHFOEXCGGS-UHFFFAOYSA-N 0.000 claims 1
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
• QADLIMTUDQPESU-UHFFFAOYSA-N 3-propan-2-yl-1h-pyridin-2-one Chemical compound CC(C)C1=CC=CN=C1O QADLIMTUDQPESU-UHFFFAOYSA-N 0.000 claims 1
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 1
• KPQWJMBSWIKWOP-UHFFFAOYSA-N 4-(6-chloro-2-oxo-1-pentan-3-yl-3h-imidazo[4,5-b]pyridin-7-yl)benzoic acid Chemical compound ClC1=CN=C2NC(=O)N(C(CC)CC)C2=C1C1=CC=C(C(O)=O)C=C1 KPQWJMBSWIKWOP-UHFFFAOYSA-N 0.000 claims 1
• BMDWOFRPWOGVFM-UHFFFAOYSA-N 6-chloro-1-pentan-3-yl-7-(1h-pyrazol-5-yl)-3h-imidazo[4,5-b]pyridin-2-one Chemical compound ClC1=CN=C2NC(=O)N(C(CC)CC)C2=C1C1=CC=NN1 BMDWOFRPWOGVFM-UHFFFAOYSA-N 0.000 claims 1
• DXAZOKMFWXNGDP-UHFFFAOYSA-N 6-chloro-1-pentan-3-yl-7-pyridin-3-yl-3h-imidazo[4,5-b]pyridin-2-one Chemical compound ClC1=CN=C2NC(=O)N(C(CC)CC)C2=C1C1=CC=CN=C1 DXAZOKMFWXNGDP-UHFFFAOYSA-N 0.000 claims 1
• FHALJWCXXHGPHH-UHFFFAOYSA-N 6-chloro-1-pentan-3-yl-7-pyridin-4-yl-3h-imidazo[4,5-b]pyridin-2-one Chemical compound ClC1=CN=C2NC(=O)N(C(CC)CC)C2=C1C1=CC=NC=C1 FHALJWCXXHGPHH-UHFFFAOYSA-N 0.000 claims 1
• RIPHYAKSQVGIMZ-NSHDSACASA-N 6-chloro-7-(4-fluorophenyl)-1-[(2s)-1-hydroxybutan-2-yl]-3h-imidazo[4,5-b]pyridin-2-one Chemical compound ClC1=CN=C2NC(=O)N([C@H](CO)CC)C2=C1C1=CC=C(F)C=C1 RIPHYAKSQVGIMZ-NSHDSACASA-N 0.000 claims 1
• KQCHFZKFXNKNTM-UHFFFAOYSA-N 6-chloro-7-[3-(2-hydroxypropan-2-yl)phenyl]-1-pentan-3-yl-3h-imidazo[4,5-b]pyridin-2-one Chemical compound ClC1=CN=C2NC(=O)N(C(CC)CC)C2=C1C1=CC=CC(C(C)(C)O)=C1 KQCHFZKFXNKNTM-UHFFFAOYSA-N 0.000 claims 1
• 229920001661 Chitosan Polymers 0.000 claims 1
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
• YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical class [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims 1
• KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 1
• 208000021642 Muscular disease Diseases 0.000 claims 1
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 1
• 101710167936 Troponin T, skeletal muscle Proteins 0.000 claims 1
• METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 1
• 125000000068 chlorophenyl group Chemical group 0.000 claims 1
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
• 239000000796 flavoring agent Substances 0.000 claims 1
• 125000001207 fluorophenyl group Chemical group 0.000 claims 1
• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims 1
• 150000002825 nitriles Chemical class 0.000 claims 1
• 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 1
• 239000001397 quillaja saponaria molina bark Substances 0.000 claims 1
• 229930182490 saponin Natural products 0.000 claims 1
• 150000007949 saponins Chemical class 0.000 claims 1
• 238000004611 spectroscopical analysis Methods 0.000 claims 1
• 230000004936 stimulating effect Effects 0.000 claims 1
• 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 1
• 102000001708 Protein Isoforms Human genes 0.000 abstract description 6
• 108010029485 Protein Isoforms Proteins 0.000 abstract description 6
• 239000012634 fragment Substances 0.000 abstract description 6
• 102000005937 Tropomyosin Human genes 0.000 abstract description 2
• 108010030743 Tropomyosin Proteins 0.000 abstract description 2
• 208000036119 Frailty Diseases 0.000 abstract 1
• 102000004987 Troponin T Human genes 0.000 abstract 1
• 108090001108 Troponin T Proteins 0.000 abstract 1
• 206010003549 asthenia Diseases 0.000 abstract 1
• 239000002585 base Substances 0.000 description 52
• XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 44
• 239000000243 solution Substances 0.000 description 35
• 238000006243 chemical reaction Methods 0.000 description 30
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
• 235000019439 ethyl acetate Nutrition 0.000 description 22
• 125000001424 substituent group Chemical group 0.000 description 20
• 239000000047 product Substances 0.000 description 19
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
• 239000007787 solid Substances 0.000 description 17
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
• 125000005037 alkyl phenyl group Chemical group 0.000 description 16
• 239000003795 chemical substances by application Substances 0.000 description 16
• 239000000843 powder Substances 0.000 description 16
• 125000004432 carbon atom Chemical group C* 0.000 description 14
• 125000001188 haloalkyl group Chemical group 0.000 description 14
• 125000000623 heterocyclic group Chemical group 0.000 description 14
• 238000002360 preparation method Methods 0.000 description 14
• 235000018102 proteins Nutrition 0.000 description 14
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 14
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