EA004935B1 - Производные изотиазола, применимые в качестве противораковых агентов - Google Patents

Info

Publication number

EA004935B1

EA004935B1 EA200001146A EA200001146A EA004935B1 EA 004935 B1 EA004935 B1 EA 004935B1 EA 200001146 A EA200001146 A EA 200001146A EA 200001146 A EA200001146 A EA 200001146A EA 004935 B1 EA004935 B1 EA 004935B1

Authority

EA

Eurasian Patent Office

Prior art keywords

isothiazole

carboxylic acid

ureido

acid amide

methylbenzyloxy

Prior art date

1998-06-04

Links

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• 239000002246 antineoplastic agent Substances 0.000 title claims description 4
• 150000003854 isothiazoles Chemical class 0.000 title description 3
• -1 micro Chemical group 0.000 claims abstract description 340
• 150000001875 compounds Chemical class 0.000 claims abstract description 264
• 238000000034 method Methods 0.000 claims abstract description 102
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 61
• 150000003839 salts Chemical class 0.000 claims abstract description 46
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 42
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 36
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 26
• 241000124008 Mammalia Species 0.000 claims abstract description 25
• 201000011510 cancer Diseases 0.000 claims abstract description 22
• 208000035475 disorder Diseases 0.000 claims abstract description 22
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract description 21
• 125000003118 aryl group Chemical group 0.000 claims abstract description 21
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 21
• 125000001424 substituent group Chemical group 0.000 claims abstract description 21
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
• 125000004122 cyclic group Chemical group 0.000 claims abstract description 20
• 229940002612 prodrug Drugs 0.000 claims abstract description 18
• 239000000651 prodrug Substances 0.000 claims abstract description 18
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 17
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 13
• 210000002307 prostate Anatomy 0.000 claims abstract description 12
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
• 210000000481 breast Anatomy 0.000 claims abstract description 8
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 8
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims abstract description 7
• 208000024770 Thyroid neoplasm Diseases 0.000 claims abstract description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
• 239000003937 drug carrier Substances 0.000 claims abstract description 7
• ZQMFJMRCBGOLED-UHFFFAOYSA-N 3-[(2,5-difluoro-4-methylphenyl)methoxy]-5-[4-(3,4-dihydroxypyrrolidin-1-yl)butylcarbamoylamino]-1,2-thiazole-4-carboxamide Chemical compound C1=C(F)C(C)=CC(F)=C1COC1=NSC(NC(=O)NCCCCN2CC(O)C(O)C2)=C1C(N)=O ZQMFJMRCBGOLED-UHFFFAOYSA-N 0.000 claims abstract description 6
• PNLQTLDEFBVYHM-UHFFFAOYSA-N 5-(4-pyrrolidin-1-ylbutylcarbamoylamino)-3-[(2,3,6-trifluoro-4-methylphenyl)methoxy]-1,2-thiazole-4-carboxamide Chemical compound FC1=C(F)C(C)=CC(F)=C1COC1=NSC(NC(=O)NCCCCN2CCCC2)=C1C(N)=O PNLQTLDEFBVYHM-UHFFFAOYSA-N 0.000 claims abstract description 6
• 210000004072 lung Anatomy 0.000 claims abstract description 6
• 201000002510 thyroid cancer Diseases 0.000 claims abstract description 6
• WKCLDWBEDQOPTO-UHFFFAOYSA-N 3-[(2,5-difluoro-4-methylphenyl)methoxy]-5-[4-[2-(hydroxymethyl)pyrrolidin-1-yl]butylcarbamoylamino]-1,2-thiazole-4-carboxamide Chemical compound C1=C(F)C(C)=CC(F)=C1COC1=NSC(NC(=O)NCCCCN2C(CCC2)CO)=C1C(N)=O WKCLDWBEDQOPTO-UHFFFAOYSA-N 0.000 claims abstract description 5
• QYQQDBQNTUOFJL-UHFFFAOYSA-N 3-[(2,6-difluoro-4-methylphenyl)methoxy]-5-(3-pyrrolidin-1-ylpropylcarbamoylamino)-1,2-thiazole-4-carboxamide Chemical compound FC1=CC(C)=CC(F)=C1COC1=NSC(NC(=O)NCCCN2CCCC2)=C1C(N)=O QYQQDBQNTUOFJL-UHFFFAOYSA-N 0.000 claims abstract description 5
• ARMSUXIOUXKTQE-UHFFFAOYSA-N 3-[(2,6-difluoro-4-methylphenyl)methoxy]-5-[2-(1-methylpyrrolidin-2-yl)ethylcarbamoylamino]-1,2-thiazole-4-carboxamide Chemical compound CN1CCCC1CCNC(=O)NC1=C(C(N)=O)C(OCC=2C(=CC(C)=CC=2F)F)=NS1 ARMSUXIOUXKTQE-UHFFFAOYSA-N 0.000 claims abstract description 5
• HCYLBNPHRUPOIC-UHFFFAOYSA-N 3-[(4-bromo-2,3,6-trifluorophenyl)methoxy]-5-(4-pyrrolidin-1-ylbutylcarbamoylamino)-1,2-thiazole-4-carboxamide Chemical compound S1N=C(OCC=2C(=C(F)C(Br)=CC=2F)F)C(C(=O)N)=C1NC(=O)NCCCCN1CCCC1 HCYLBNPHRUPOIC-UHFFFAOYSA-N 0.000 claims abstract description 5
• AHTAYKWZFAVPQM-UHFFFAOYSA-N 5-(3-pyrrolidin-1-ylpropylcarbamoylamino)-3-[(2,3,6-trifluoro-4-methylphenyl)methoxy]-1,2-thiazole-4-carboxamide Chemical compound FC1=C(F)C(C)=CC(F)=C1COC1=NSC(NC(=O)NCCCN2CCCC2)=C1C(N)=O AHTAYKWZFAVPQM-UHFFFAOYSA-N 0.000 claims abstract description 5
• SKYJJHBJQTTWCK-UHFFFAOYSA-N 5-[2-(1-methylpyrrolidin-2-yl)ethylcarbamoylamino]-3-[(2,3,6-trifluoro-4-methylphenyl)methoxy]-1,2-thiazole-4-carboxamide Chemical compound CN1CCCC1CCNC(=O)NC1=C(C(N)=O)C(OCC=2C(=C(F)C(C)=CC=2F)F)=NS1 SKYJJHBJQTTWCK-UHFFFAOYSA-N 0.000 claims abstract description 5
• 206010020718 hyperplasia Diseases 0.000 claims abstract description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
• 239000012453 solvate Substances 0.000 claims abstract description 5
• GRIBVKFHFTZOCK-UHFFFAOYSA-N 3-[(2,5-difluoro-4-methylphenyl)methoxy]-5-[4-(3-hydroxypyrrolidin-1-yl)butylcarbamoylamino]-1,2-thiazole-4-carboxamide Chemical compound C1=C(F)C(C)=CC(F)=C1COC1=NSC(NC(=O)NCCCCN2CC(O)CC2)=C1C(N)=O GRIBVKFHFTZOCK-UHFFFAOYSA-N 0.000 claims abstract description 4
• ZGACOKVBPWMCTI-UHFFFAOYSA-N 3-[(4-chloro-2,3,6-trifluorophenyl)methoxy]-5-[4-[2-(hydroxymethyl)pyrrolidin-1-yl]butylcarbamoylamino]-1,2-thiazole-4-carboxamide Chemical compound S1N=C(OCC=2C(=C(F)C(Cl)=CC=2F)F)C(C(=O)N)=C1NC(=O)NCCCCN1CCCC1CO ZGACOKVBPWMCTI-UHFFFAOYSA-N 0.000 claims abstract description 4
• AVBLJLMYGYPZBD-UHFFFAOYSA-N 3-[(4-chloro-2,6-difluorophenyl)methoxy]-5-(4-imidazol-1-ylbutylcarbamoylamino)-1,2-thiazole-4-carboxamide Chemical compound S1N=C(OCC=2C(=CC(Cl)=CC=2F)F)C(C(=O)N)=C1NC(=O)NCCCCN1C=CN=C1 AVBLJLMYGYPZBD-UHFFFAOYSA-N 0.000 claims abstract description 4
• KBASJCBTQBVBOG-UHFFFAOYSA-N 3-[(4-chloro-2,6-difluorophenyl)methoxy]-5-(4-pyrrolidin-1-ylbutylcarbamoylamino)-1,2-thiazole-4-carboxamide Chemical compound S1N=C(OCC=2C(=CC(Cl)=CC=2F)F)C(C(=O)N)=C1NC(=O)NCCCCN1CCCC1 KBASJCBTQBVBOG-UHFFFAOYSA-N 0.000 claims abstract description 4
• NYYQETQHPXRWLV-UHFFFAOYSA-N 3-[(4-chloro-2,6-difluorophenyl)methoxy]-5-[2-(1-methylpyrrolidin-2-yl)ethylcarbamoylamino]-1,2-thiazole-4-carboxamide Chemical compound CN1CCCC1CCNC(=O)NC1=C(C(N)=O)C(OCC=2C(=CC(Cl)=CC=2F)F)=NS1 NYYQETQHPXRWLV-UHFFFAOYSA-N 0.000 claims abstract description 4
• ZHELHOUQIKLLQE-UHFFFAOYSA-N 3-[(4-chloro-2,6-difluorophenyl)methoxy]-5-[4-(3,4-dihydroxypyrrolidin-1-yl)butylcarbamoylamino]-1,2-thiazole-4-carboxamide Chemical compound S1N=C(OCC=2C(=CC(Cl)=CC=2F)F)C(C(=O)N)=C1NC(=O)NCCCCN1CC(O)C(O)C1 ZHELHOUQIKLLQE-UHFFFAOYSA-N 0.000 claims abstract description 4
• 210000003734 kidney Anatomy 0.000 claims abstract description 4
• NKGBEPBSPHYERX-UHFFFAOYSA-N 3-[(4-chloro-2,3,6-trifluorophenyl)methoxy]-5-[(3-hydroxy-5-pyrrolidin-1-ylpentyl)carbamoylamino]-1,2-thiazole-4-carboxamide Chemical compound S1N=C(OCC=2C(=C(F)C(Cl)=CC=2F)F)C(C(=O)N)=C1NC(=O)NCCC(O)CCN1CCCC1 NKGBEPBSPHYERX-UHFFFAOYSA-N 0.000 claims abstract description 3
• ZPNJGUBDUYTZLI-UHFFFAOYSA-N 3-[(4-chloro-2,6-difluorophenyl)methoxy]-5-[4-[2-(hydroxymethyl)pyrrolidin-1-yl]butylcarbamoylamino]-1,2-thiazole-4-carboxamide Chemical compound S1N=C(OCC=2C(=CC(Cl)=CC=2F)F)C(C(=O)N)=C1NC(=O)NCCCCN1CCCC1CO ZPNJGUBDUYTZLI-UHFFFAOYSA-N 0.000 claims abstract description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract 11
• CRBQHUZGHXBQOI-UHFFFAOYSA-N 3-[(4-chloro-2,3,6-trifluorophenyl)methoxy]-5-(4-imidazol-1-ylbutylcarbamoylamino)-1,2-thiazole-4-carboxamide Chemical compound S1N=C(OCC=2C(=C(F)C(Cl)=CC=2F)F)C(C(=O)N)=C1NC(=O)NCCCCN1C=CN=C1 CRBQHUZGHXBQOI-UHFFFAOYSA-N 0.000 claims abstract 2
• 150000003536 tetrazoles Chemical class 0.000 claims abstract 2
• 150000001408 amides Chemical class 0.000 claims description 129
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 64
• 125000004429 atom Chemical group 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
• 229910052794 bromium Inorganic materials 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 9
• 150000002367 halogens Chemical class 0.000 claims description 9
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 239000000460 chlorine Substances 0.000 claims description 7
• 239000003112 inhibitor Substances 0.000 claims description 7
• 210000000496 pancreas Anatomy 0.000 claims description 7
• 206010005003 Bladder cancer Diseases 0.000 claims description 6
• 206010009944 Colon cancer Diseases 0.000 claims description 6
• 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 6
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 6
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 6
• 206010017758 gastric cancer Diseases 0.000 claims description 6
• 201000011549 stomach cancer Diseases 0.000 claims description 6
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 6
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
• 102000004190 Enzymes Human genes 0.000 claims description 5
• 108090000790 Enzymes Proteins 0.000 claims description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 5
• 229910052801 chlorine Inorganic materials 0.000 claims description 5
• 201000004101 esophageal cancer Diseases 0.000 claims description 5
• 239000011737 fluorine Substances 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 208000020816 lung neoplasm Diseases 0.000 claims description 5
• RDWLAZKXPUAJLU-UHFFFAOYSA-N 3-[(2,6-difluoro-4-methylphenyl)methoxy]-5-[(3-hydroxy-5-pyrrolidin-1-ylpentyl)carbamoylamino]-1,2-thiazole-4-carboxamide Chemical compound FC1=CC(C)=CC(F)=C1COC1=NSC(NC(=O)NCCC(O)CCN2CCCC2)=C1C(N)=O RDWLAZKXPUAJLU-UHFFFAOYSA-N 0.000 claims description 4
• PJXPORIRXYJDLD-UHFFFAOYSA-N 3-[(4-bromo-2,6-difluorophenyl)methoxy]-5-(4-pyrrolidin-1-ylbutylcarbamoylamino)-1,2-thiazole-4-carboxylic acid Chemical compound S1N=C(OCC=2C(=CC(Br)=CC=2F)F)C(C(=O)O)=C1NC(=O)NCCCCN1CCCC1 PJXPORIRXYJDLD-UHFFFAOYSA-N 0.000 claims description 4
• JZKSAVFKXZDXTQ-UHFFFAOYSA-N 5-[(3-hydroxy-5-pyrrolidin-1-ylpentyl)carbamoylamino]-3-[(2,3,6-trifluoro-4-methylphenyl)methoxy]-1,2-thiazole-4-carboxamide Chemical compound FC1=C(F)C(C)=CC(F)=C1COC1=NSC(NC(=O)NCCC(O)CCN2CCCC2)=C1C(N)=O JZKSAVFKXZDXTQ-UHFFFAOYSA-N 0.000 claims description 4
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 4
• 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 4
• 230000000340 anti-metabolite Effects 0.000 claims description 4
• 229940100197 antimetabolite Drugs 0.000 claims description 4
• 239000002256 antimetabolite Substances 0.000 claims description 4
• 239000003102 growth factor Substances 0.000 claims description 4
• 210000003128 head Anatomy 0.000 claims description 4
• 201000005202 lung cancer Diseases 0.000 claims description 4
• IDFPCZGRESLUMB-UHFFFAOYSA-N 3-[(4-chloro-2,6-difluorophenyl)methoxy]-5-[(3-hydroxy-5-pyrrolidin-1-ylpentyl)carbamoylamino]-1,2-thiazole-4-carboxamide Chemical compound S1N=C(OCC=2C(=CC(Cl)=CC=2F)F)C(C(=O)N)=C1NC(=O)NCCC(O)CCN1CCCC1 IDFPCZGRESLUMB-UHFFFAOYSA-N 0.000 claims description 3
• 239000002168 alkylating agent Substances 0.000 claims description 3
• 229940100198 alkylating agent Drugs 0.000 claims description 3
• 230000002280 anti-androgenic effect Effects 0.000 claims description 3
• 230000003388 anti-hormonal effect Effects 0.000 claims description 3
• 239000000051 antiandrogen Substances 0.000 claims description 3
• 210000003739 neck Anatomy 0.000 claims description 3
• 206010041823 squamous cell carcinoma Diseases 0.000 claims description 3
• YRXZENYHAZGPBF-UHFFFAOYSA-N 3-[(4-chloro-2,3,6-trifluorophenyl)methoxy]-5-(4-pyrrolidin-1-ylbutylcarbamoylamino)-1,2-thiazole-4-carboxamide Chemical compound S1N=C(OCC=2C(=C(F)C(Cl)=CC=2F)F)C(C(=O)N)=C1NC(=O)NCCCCN1CCCC1 YRXZENYHAZGPBF-UHFFFAOYSA-N 0.000 claims description 2
• 125000003342 alkenyl group Chemical group 0.000 claims description 2
• 125000000304 alkynyl group Chemical group 0.000 claims description 2
• 239000003534 dna topoisomerase inhibitor Substances 0.000 claims description 2
• 230000011278 mitosis Effects 0.000 claims description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
• 229940044693 topoisomerase inhibitor Drugs 0.000 claims description 2
• ATXPSRAGQHXUCP-UHFFFAOYSA-N 3-[(4-bromo-2,6-difluorophenyl)methoxy]-5-(4-pyrrolidin-1-ylbutylcarbamoylamino)-1,2-thiazole-4-carboxamide;methanesulfonic acid Chemical compound CS(O)(=O)=O.N=1SC(NC(=O)NCCCCN2CCCC2)=C(C(=O)N)C=1OCC1=C(F)C=C(Br)C=C1F ATXPSRAGQHXUCP-UHFFFAOYSA-N 0.000 claims 2
• 210000001672 ovary Anatomy 0.000 claims 2
• 208000017572 squamous cell neoplasm Diseases 0.000 claims 2
• NNPJZJJMQDXYGN-UHFFFAOYSA-N 3-[(4-bromo-2,6-difluorophenyl)methoxy]-5-(4-pyrrolidin-1-ylbutylcarbamoylamino)-1,2-thiazole-4-carboxamide;hydrochloride Chemical compound Cl.S1N=C(OCC=2C(=CC(Br)=CC=2F)F)C(C(=O)N)=C1NC(=O)NCCCCN1CCCC1 NNPJZJJMQDXYGN-UHFFFAOYSA-N 0.000 claims 1
• KXZQJNNZLZSZEA-UHFFFAOYSA-N 3-[(4-chloro-2,3,6-trifluorophenyl)methoxy]-5-[2-(1-methylpyrrolidin-2-yl)ethylcarbamoylamino]-1,2-thiazole-4-carboxylic acid Chemical compound CN1CCCC1CCNC(=O)NC1=C(C(O)=O)C(OCC=2C(=C(F)C(Cl)=CC=2F)F)=NS1 KXZQJNNZLZSZEA-UHFFFAOYSA-N 0.000 claims 1
• 239000005557 antagonist Substances 0.000 claims 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
• 230000022131 cell cycle Effects 0.000 claims 1
• 229940111134 coxibs Drugs 0.000 claims 1
• 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims 1
• 239000000367 immunologic factor Substances 0.000 claims 1
• 239000012444 intercalating antibiotic Substances 0.000 claims 1
• 239000002464 receptor antagonist Substances 0.000 claims 1
• 229940044551 receptor antagonist Drugs 0.000 claims 1
• HXHAJRMTJXHJJZ-UHFFFAOYSA-N 3-[(4-bromo-2,6-difluorophenyl)methoxy]-5-(4-pyrrolidin-1-ylbutylcarbamoylamino)-1,2-thiazole-4-carboxamide Chemical compound S1N=C(OCC=2C(=CC(Br)=CC=2F)F)C(C(=O)N)=C1NC(=O)NCCCCN1CCCC1 HXHAJRMTJXHJJZ-UHFFFAOYSA-N 0.000 abstract description 8
• 229910052717 sulfur Inorganic materials 0.000 abstract description 8
• DYTGJDKRYVLILD-UHFFFAOYSA-N 3-[(2,6-difluoro-4-methylphenyl)methoxy]-5-(4-pyrrolidin-1-ylbutylcarbamoylamino)-1,2-thiazole-4-carboxamide Chemical compound FC1=CC(C)=CC(F)=C1COC1=NSC(NC(=O)NCCCCN2CCCC2)=C1C(N)=O DYTGJDKRYVLILD-UHFFFAOYSA-N 0.000 abstract description 6
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 abstract description 6
• 125000005843 halogen group Chemical group 0.000 abstract description 6
• 125000005842 heteroatom Chemical group 0.000 abstract description 6
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 abstract description 5
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract description 4
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• 230000002611 ovarian Effects 0.000 abstract description 2
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• 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 3
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• 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
• 229910006069 SO3H Inorganic materials 0.000 abstract 1
• 210000004556 brain Anatomy 0.000 abstract 1
• 125000001246 bromo group Chemical group Br* 0.000 abstract 1
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 abstract 1
• 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
• 230000002496 gastric effect Effects 0.000 abstract 1
• 239000000203 mixture Substances 0.000 description 106
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• 239000007787 solid Substances 0.000 description 56
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 43
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• 238000005160 1H NMR spectroscopy Methods 0.000 description 36
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• BEPMYBTTZSNHPS-UHFFFAOYSA-N 1,2-thiazole-4-carboxamide Chemical compound NC(=O)C=1C=NSC=1 BEPMYBTTZSNHPS-UHFFFAOYSA-N 0.000 description 27
• 238000006243 chemical reaction Methods 0.000 description 27
• 238000005481 NMR spectroscopy Methods 0.000 description 26
• 238000003756 stirring Methods 0.000 description 24
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• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
• 230000014759 maintenance of location Effects 0.000 description 22
• 239000000047 product Substances 0.000 description 21
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
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