TW201038572A - Substituted spiro-amide compounds - Google Patents

Info

Publication number

TW201038572A

TW201038572A TW099108105A TW99108105A TW201038572A TW 201038572 A TW201038572 A TW 201038572A TW 099108105 A TW099108105 A TW 099108105A TW 99108105 A TW99108105 A TW 99108105A TW 201038572 A TW201038572 A TW 201038572A

Authority

TW

Taiwan

Prior art keywords

carbonyl

dihydro

group

ind

diazaspiro

Prior art date

2009-03-25

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 claims abstract description 139
• 238000002360 preparation method Methods 0.000 claims abstract description 19
• 239000003814 drug Substances 0.000 claims abstract description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 592
• -1 amide compound Chemical class 0.000 claims description 491
• 125000003118 aryl group Chemical group 0.000 claims description 216
• 125000001072 heteroaryl group Chemical group 0.000 claims description 173
• 125000000217 alkyl group Chemical group 0.000 claims description 167
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 144
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 132
• 125000002947 alkylene group Chemical group 0.000 claims description 123
• 125000001424 substituent group Chemical group 0.000 claims description 119
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 116
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 114
• MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 106
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 79
• 229910052731 fluorine Inorganic materials 0.000 claims description 78
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 76
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 74
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 73
• 229910052801 chlorine Inorganic materials 0.000 claims description 73
• 239000011737 fluorine Substances 0.000 claims description 72
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 71
• 239000000460 chlorine Substances 0.000 claims description 71
• 125000004429 atom Chemical group 0.000 claims description 69
• 125000003277 amino group Chemical group 0.000 claims description 68
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 66
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 66
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 58
• 125000003545 alkoxy group Chemical group 0.000 claims description 56
• 150000001412 amines Chemical class 0.000 claims description 56
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 56
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 55
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 55
• 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 51
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 51
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 50
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 49
• 125000005842 heteroatom Chemical group 0.000 claims description 49
• 125000000623 heterocyclic group Chemical group 0.000 claims description 48
• 239000000203 mixture Substances 0.000 claims description 48
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 47
• 239000002253 acid Substances 0.000 claims description 44
• 229910052757 nitrogen Inorganic materials 0.000 claims description 41
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 40
• 239000007789 gas Substances 0.000 claims description 36
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 35
• DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 34
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 34
• 229910052799 carbon Inorganic materials 0.000 claims description 33
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 33
• HBZHNVUMFPGVHW-UHFFFAOYSA-N 2-chloro-1h-indole Chemical compound C1=CC=C2NC(Cl)=CC2=C1 HBZHNVUMFPGVHW-UHFFFAOYSA-N 0.000 claims description 32
• 150000001721 carbon Chemical group 0.000 claims description 32
• 208000002193 Pain Diseases 0.000 claims description 31
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 31
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 30
• GWRSATNRNFYMDI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound FC=1C=C(NC=2N=C3N(C4CCCC4)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCN(C)CC1 GWRSATNRNFYMDI-UHFFFAOYSA-N 0.000 claims description 29
• 239000004202 carbamide Substances 0.000 claims description 29
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 28
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 28
• 229910052794 bromium Inorganic materials 0.000 claims description 28
• 229920006395 saturated elastomer Polymers 0.000 claims description 27
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 26
• RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 26
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
• 125000004076 pyridyl group Chemical group 0.000 claims description 24
• 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 23
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
• 125000001624 naphthyl group Chemical group 0.000 claims description 21
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 21
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 21
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 18
• 239000001257 hydrogen Substances 0.000 claims description 17
• 229910052739 hydrogen Inorganic materials 0.000 claims description 17
• 125000004419 alkynylene group Chemical group 0.000 claims description 16
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 16
• 239000000126 substance Substances 0.000 claims description 16
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 15
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 15
• MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 15
• 125000004450 alkenylene group Chemical group 0.000 claims description 15
• 125000000524 functional group Chemical group 0.000 claims description 15
• 125000001544 thienyl group Chemical group 0.000 claims description 15
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 14
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 13
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
• GEDMZUMBTQBBQW-UHFFFAOYSA-N C(CCCCCCCCC)N.CCCCCCCC(CC)C(=O)O Chemical compound C(CCCCCCCCC)N.CCCCCCCC(CC)C(=O)O GEDMZUMBTQBBQW-UHFFFAOYSA-N 0.000 claims description 12
• 125000004122 cyclic group Chemical group 0.000 claims description 12
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
• 150000003839 salts Chemical class 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims description 9
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
• 125000001153 fluoro group Chemical group F* 0.000 claims description 9
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 9
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 8
• 229940079593 drug Drugs 0.000 claims description 8
• YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 8
• 125000004434 sulfur atom Chemical group 0.000 claims description 8
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 7
• 241000237858 Gastropoda Species 0.000 claims description 7
• 229940077388 benzenesulfonate Drugs 0.000 claims description 7
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• 201000001119 neuropathy Diseases 0.000 claims description 7
• 230000007823 neuropathy Effects 0.000 claims description 7
• 125000004043 oxo group Chemical group O=* 0.000 claims description 7
• 230000036961 partial effect Effects 0.000 claims description 7
• 208000033808 peripheral neuropathy Diseases 0.000 claims description 7
• 239000005711 Benzoic acid Substances 0.000 claims description 6
• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
• 125000005529 alkyleneoxy group Chemical group 0.000 claims description 6
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
• 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 125000004212 difluorophenyl group Chemical group 0.000 claims description 6
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• 239000004305 biphenyl Substances 0.000 claims description 5
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 239000008267 milk Substances 0.000 claims description 5
• 235000019391 nitrogen oxide Nutrition 0.000 claims description 5
• 150000003254 radicals Chemical class 0.000 claims description 5
• XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 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 4
• ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 101150020251 NR13 gene Proteins 0.000 claims description 4
• 208000008589 Obesity Diseases 0.000 claims description 4
• 206010036790 Productive cough Diseases 0.000 claims description 4
• 206010040070 Septic Shock Diseases 0.000 claims description 4
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 4
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
• 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 4
• 229960003753 nitric oxide Drugs 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 235000020824 obesity Nutrition 0.000 claims description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 230000036303 septic shock Effects 0.000 claims description 4
• 210000003802 sputum Anatomy 0.000 claims description 4
• 208000024794 sputum Diseases 0.000 claims description 4
• 208000011580 syndromic disease Diseases 0.000 claims description 4
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 4
• 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 3
• LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims description 3
• VVZRKVYGKNFTRR-UHFFFAOYSA-N 12h-benzo[a]xanthene Chemical class C1=CC=CC2=C3CC4=CC=CC=C4OC3=CC=C21 VVZRKVYGKNFTRR-UHFFFAOYSA-N 0.000 claims description 3
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
• QOQGUYAEXRBZQN-UHFFFAOYSA-N 2,3-dichloro-1h-indole Chemical compound C1=CC=C2C(Cl)=C(Cl)NC2=C1 QOQGUYAEXRBZQN-UHFFFAOYSA-N 0.000 claims description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 201000004624 Dermatitis Diseases 0.000 claims description 3
• 206010065390 Inflammatory pain Diseases 0.000 claims description 3
• XUYPXLNMDZIRQH-LURJTMIESA-N N-acetyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-LURJTMIESA-N 0.000 claims description 3
• 208000012902 Nervous system disease Diseases 0.000 claims description 3
• 208000025966 Neurological disease Diseases 0.000 claims description 3
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 3
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 3
• 238000001354 calcination Methods 0.000 claims description 3
• 206010012601 diabetes mellitus Diseases 0.000 claims description 3
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 3
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• 230000002757 inflammatory effect Effects 0.000 claims description 3
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical group CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 3
• 210000004185 liver Anatomy 0.000 claims description 3
• 235000013336 milk Nutrition 0.000 claims description 3
• 210000004080 milk Anatomy 0.000 claims description 3
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
• 230000010410 reperfusion Effects 0.000 claims description 3
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• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
• VVHQVXXPZDALDV-BOXHHOBZSA-N (3s)-3-[7-[[4-(morpholin-4-ylmethyl)phenyl]methoxy]-3-oxo-1h-isoindol-2-yl]piperidine-2,6-dione;hydrochloride Chemical compound Cl.O=C1N([C@@H]2C(NC(=O)CC2)=O)CC2=C1C=CC=C2OCC(C=C1)=CC=C1CN1CCOCC1 VVHQVXXPZDALDV-BOXHHOBZSA-N 0.000 claims description 2
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
• ISUSFJKIFZLDJI-UHFFFAOYSA-N 2-fluoro-4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C(F)=C1 ISUSFJKIFZLDJI-UHFFFAOYSA-N 0.000 claims description 2
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 2
• UFKLYTOEMRFKAD-SHTZXODSSA-N C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NCC1=O Chemical compound C1C[C@@H](OC)CC[C@@H]1N1C2=NC(C=3C=NC(=CC=3)C(C)(C)O)=CN=C2NCC1=O UFKLYTOEMRFKAD-SHTZXODSSA-N 0.000 claims description 2
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
• 208000019695 Migraine disease Diseases 0.000 claims description 2
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
• PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 2
• 102100040791 Zona pellucida-binding protein 1 Human genes 0.000 claims description 2
• 150000001408 amides Chemical class 0.000 claims description 2
• 230000033115 angiogenesis Effects 0.000 claims description 2
• 125000005002 aryl methyl group Chemical group 0.000 claims description 2
• 125000002837 carbocyclic group Chemical group 0.000 claims description 2
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 2
• 239000010949 copper Substances 0.000 claims description 2
• 125000004802 cyanophenyl group Chemical group 0.000 claims description 2
• 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
• LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 2
• 239000003112 inhibitor Substances 0.000 claims description 2
• XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
• 206010027599 migraine Diseases 0.000 claims description 2
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• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
• 239000002244 precipitate Substances 0.000 claims description 2
• 125000006413 ring segment Chemical group 0.000 claims description 2
• PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 2
• 235000021286 stilbenes Nutrition 0.000 claims description 2
• 229940124530 sulfonamide Drugs 0.000 claims description 2
• 150000003456 sulfonamides Chemical class 0.000 claims description 2
• 125000004149 thio group Chemical group *S* 0.000 claims description 2
• 125000002948 undecyl group Chemical group [H]C([*])([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])[H] 0.000 claims description 2
• 229930182817 methionine Natural products 0.000 claims 5
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