TW201242956A - Heterocyclic compounds - Google Patents

Info

Publication number

TW201242956A

TW201242956A TW100136019A TW100136019A TW201242956A TW 201242956 A TW201242956 A TW 201242956A TW 100136019 A TW100136019 A TW 100136019A TW 100136019 A TW100136019 A TW 100136019A TW 201242956 A TW201242956 A TW 201242956A

Authority

TW

Taiwan

Prior art keywords

group

compound

substituted

alkyl

optionally

Prior art date

2010-10-07

Links

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• 150000002391 heterocyclic compounds Chemical class 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 539
• 125000001424 substituent group Chemical group 0.000 claims abstract description 232
• 125000003118 aryl group Chemical group 0.000 claims abstract description 79
• 150000003839 salts Chemical class 0.000 claims abstract description 72
• -1 Trimethylmethyl Chemical group 0.000 claims description 424
• 125000000217 alkyl group Chemical group 0.000 claims description 194
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 151
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 140
• 125000003545 alkoxy group Chemical group 0.000 claims description 106
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 103
• 125000003277 amino group Chemical group 0.000 claims description 101
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 96
• 150000001412 amines Chemical class 0.000 claims description 74
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 70
• 239000003814 drug Substances 0.000 claims description 64
• 229940079593 drug Drugs 0.000 claims description 60
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 58
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 48
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
• 239000007789 gas Substances 0.000 claims description 45
• 229910052731 fluorine Inorganic materials 0.000 claims description 39
• 125000001153 fluoro group Chemical group F* 0.000 claims description 38
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 35
• 125000000623 heterocyclic group Chemical group 0.000 claims description 26
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 22
• 229910052801 chlorine Inorganic materials 0.000 claims description 21
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• 208000002193 Pain Diseases 0.000 claims description 17
• 206010066218 Stress Urinary Incontinence Diseases 0.000 claims description 17
• 230000036407 pain Effects 0.000 claims description 17
• 239000000126 substance Substances 0.000 claims description 17
• 125000004104 aryloxy group Chemical group 0.000 claims description 15
• 208000019901 Anxiety disease Diseases 0.000 claims description 14
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
• 230000036506 anxiety Effects 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 239000001301 oxygen Substances 0.000 claims description 12
• 206010046543 Urinary incontinence Diseases 0.000 claims description 11
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 11
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 10
• 230000002265 prevention Effects 0.000 claims description 10
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 8
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 7
• 208000017657 Menopausal disease Diseases 0.000 claims description 7
• 208000035475 disorder Diseases 0.000 claims description 7
• 230000002485 urinary effect Effects 0.000 claims description 7
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 6
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 6
• 230000005764 inhibitory process Effects 0.000 claims description 6
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 5
• 208000013403 hyperactivity Diseases 0.000 claims description 5
• SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 claims description 5
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
• 125000005577 anthracene group Chemical group 0.000 claims description 4
• 125000000068 chlorophenyl group Chemical group 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 3
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
• ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 3
• 230000006735 deficit Effects 0.000 claims description 3
• 230000009103 reabsorption Effects 0.000 claims description 3
• 206010021639 Incontinence Diseases 0.000 claims description 2
• 125000004188 dichlorophenyl group Chemical group 0.000 claims description 2
• AQNQGBUEVCAVML-UHFFFAOYSA-N oxazepane Chemical compound C1CCNOCC1 AQNQGBUEVCAVML-UHFFFAOYSA-N 0.000 claims description 2
• 241000894007 species Species 0.000 claims description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
• 208000020401 Depressive disease Diseases 0.000 claims 1
• 150000001555 benzenes Chemical group 0.000 claims 1
• 150000001735 carboxylic acids Chemical class 0.000 claims 1
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
• 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims 1
• 230000002401 inhibitory effect Effects 0.000 abstract description 14
• 230000000407 monoamine reuptake Effects 0.000 abstract description 11
• 238000000034 method Methods 0.000 description 216
• 239000002585 base Substances 0.000 description 138
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
• 239000000203 mixture Substances 0.000 description 66
• 239000000243 solution Substances 0.000 description 66
• 125000005843 halogen group Chemical group 0.000 description 62
• 125000006239 protecting group Chemical group 0.000 description 60
• 125000003396 thiol group Chemical group [H]S* 0.000 description 59
• 125000004429 atom Chemical group 0.000 description 57
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
• 239000010949 copper Substances 0.000 description 51
• 235000019439 ethyl acetate Nutrition 0.000 description 51
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 49
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
• 238000006243 chemical reaction Methods 0.000 description 48
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 48
• 230000002829 reductive effect Effects 0.000 description 48
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
• 125000004122 cyclic group Chemical group 0.000 description 40
• 125000005049 dihydrooxadiazolyl group Chemical group O1N(NC=C1)* 0.000 description 36
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 32
• 239000011541 reaction mixture Substances 0.000 description 31
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
• 101000879840 Homo sapiens Serglycin Proteins 0.000 description 30
• 101000999079 Homo sapiens Radiation-inducible immediate-early gene IEX-1 Proteins 0.000 description 28
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
• 102100030368 Phospholipid phosphatase-related protein type 4 Human genes 0.000 description 28
• 239000004305 biphenyl Substances 0.000 description 26
• 125000006612 decyloxy group Chemical group 0.000 description 26
• 238000005160 1H NMR spectroscopy Methods 0.000 description 25
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 25
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
• 239000013078 crystal Substances 0.000 description 24
• 238000006722 reduction reaction Methods 0.000 description 23
• 239000002904 solvent Substances 0.000 description 23
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 21
• 239000003795 chemical substances by application Substances 0.000 description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 20
• 239000003112 inhibitor Substances 0.000 description 20
• VIHDTGHDWPVSMM-UHFFFAOYSA-N ruthenium;triphenylphosphane Chemical compound [Ru].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VIHDTGHDWPVSMM-UHFFFAOYSA-N 0.000 description 20
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 20
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 19
• 239000000460 chlorine Substances 0.000 description 19
• 230000003287 optical effect Effects 0.000 description 19
• 101150041968 CDC13 gene Proteins 0.000 description 18
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• 238000003786 synthesis reaction Methods 0.000 description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 17
• 229910052799 carbon Inorganic materials 0.000 description 17
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 17
• 238000002360 preparation method Methods 0.000 description 17
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 17
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
• 239000012267 brine Substances 0.000 description 16
• 125000001041 indolyl group Chemical group 0.000 description 16
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 16
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• 239000002253 acid Substances 0.000 description 15
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 15
• 229910052739 hydrogen Inorganic materials 0.000 description 15
• 238000007254 oxidation reaction Methods 0.000 description 15
• 239000008194 pharmaceutical composition Substances 0.000 description 15
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
• 125000003282 alkyl amino group Chemical group 0.000 description 14
• 125000003710 aryl alkyl group Chemical group 0.000 description 14
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 14
• 238000009472 formulation Methods 0.000 description 14
• 239000001257 hydrogen Substances 0.000 description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 14
• 238000006467 substitution reaction Methods 0.000 description 14
• SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 13
• 229910052783 alkali metal Inorganic materials 0.000 description 13
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 13
• 230000015572 biosynthetic process Effects 0.000 description 13
• 238000001816 cooling Methods 0.000 description 13
• 201000010099 disease Diseases 0.000 description 13
• 239000012153 distilled water Substances 0.000 description 13
• 238000010828 elution Methods 0.000 description 13
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 13
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 12
• 239000004202 carbamide Substances 0.000 description 12
• 235000013877 carbamide Nutrition 0.000 description 12
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
• 125000000753 cycloalkyl group Chemical group 0.000 description 12
• 238000004949 mass spectrometry Methods 0.000 description 12
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 11
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 11
• 238000000926 separation method Methods 0.000 description 11
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 10
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
• 150000001340 alkali metals Chemical class 0.000 description 10
• 150000001540 azides Chemical class 0.000 description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
• 125000004744 butyloxycarbonyl group Chemical group 0.000 description 10
• 239000003638 chemical reducing agent Substances 0.000 description 10
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
• QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 10
• 229910052707 ruthenium Inorganic materials 0.000 description 10
• 125000001425 triazolyl group Chemical group 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• 101100422872 Arabidopsis thaliana SWEET8 gene Proteins 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• 101100118563 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) RPG1 gene Proteins 0.000 description 9
• 238000007259 addition reaction Methods 0.000 description 9
• 125000004414 alkyl thio group Chemical group 0.000 description 9
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 9
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 9
• 238000002425 crystallisation Methods 0.000 description 9
• 238000005984 hydrogenation reaction Methods 0.000 description 9
• 238000006053 organic reaction Methods 0.000 description 9
• 150000002923 oximes Chemical class 0.000 description 9
• 229940076279 serotonin Drugs 0.000 description 9
• 239000011734 sodium Substances 0.000 description 9
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 8
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
• 150000001342 alkaline earth metals Chemical class 0.000 description 8
• 239000005557 antagonist Substances 0.000 description 8
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
• 230000000694 effects Effects 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 8
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 8
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 8
• 229910052708 sodium Inorganic materials 0.000 description 8
• 229940124530 sulfonamide Drugs 0.000 description 8
• 150000003456 sulfonamides Chemical class 0.000 description 8
• 125000003831 tetrazolyl group Chemical group 0.000 description 8
• 101001095043 Homo sapiens Bone marrow proteoglycan Proteins 0.000 description 7
• 101001131990 Homo sapiens Peroxidasin homolog Proteins 0.000 description 7
• 101000582986 Homo sapiens Phospholipid phosphatase-related protein type 3 Proteins 0.000 description 7
• 102100030383 Phospholipid phosphatase-related protein type 3 Human genes 0.000 description 7
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 7
• 229960003638 dopamine Drugs 0.000 description 7
• 230000032050 esterification Effects 0.000 description 7
• 238000005886 esterification reaction Methods 0.000 description 7
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 7
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 7
• 238000002844 melting Methods 0.000 description 7
• 229910052751 metal Inorganic materials 0.000 description 7
• 239000002184 metal Substances 0.000 description 7
• CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 7
• 125000001715 oxadiazolyl group Chemical group 0.000 description 7
• 238000000746 purification Methods 0.000 description 7
• 125000004076 pyridyl group Chemical group 0.000 description 7
• 238000001953 recrystallisation Methods 0.000 description 7
• 238000003756 stirring Methods 0.000 description 7
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• 102100028491 Growth arrest and DNA damage-inducible proteins-interacting protein 1 Human genes 0.000 description 6
• 101001061336 Homo sapiens Growth arrest and DNA damage-inducible proteins-interacting protein 1 Proteins 0.000 description 6
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
• 239000000556 agonist Substances 0.000 description 6
• 150000001335 aliphatic alkanes Chemical class 0.000 description 6
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 6
• AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 6
• 229910052786 argon Inorganic materials 0.000 description 6
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
• UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 6
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
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