UA76969C2

UA76969C2 - Lactams and their pharmaceutical use

Lactams and their pharmaceutical use Download PDF

Info

Publication number: UA76969C2
Authority: UA; Ukraine
Prior art keywords: substituent; group; acyl; alkyl; carbamoyl
Prior art date: 2000-12-01

Application number

UA2003055026A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Ajinomoto Kk

Priority date

2000-12-01

Filing date

2001-11-29

Publication date

2006-10-16

2001-11-29 Application filed by Ajinomoto Kk filed Critical Ajinomoto Kk

2006-10-16 Publication of UA76969C2 publication Critical patent/UA76969C2/uk

Links

150000003951 lactams Chemical class 0.000 title claims description 24
-1 lactam compounds Chemical class 0.000 claims abstract description 98
150000003839 salts Chemical class 0.000 claims abstract description 26
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 14
239000004480 active ingredient Substances 0.000 claims abstract description 11
208000007342 Diabetic Nephropathies Diseases 0.000 claims abstract description 7
208000032131 Diabetic Neuropathies Diseases 0.000 claims abstract description 7
208000008589 Obesity Diseases 0.000 claims abstract description 7
208000033679 diabetic kidney disease Diseases 0.000 claims abstract description 7
235000020824 obesity Nutrition 0.000 claims abstract description 7
125000001424 substituent group Chemical group 0.000 claims description 144
125000000217 alkyl group Chemical group 0.000 claims description 54
125000003118 aryl group Chemical group 0.000 claims description 54
125000002252 acyl group Chemical group 0.000 claims description 41
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
235000000346 sugar Nutrition 0.000 claims description 37
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 33
125000004432 carbon atom Chemical group C* 0.000 claims description 33
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 32
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
125000004423 acyloxy group Chemical group 0.000 claims description 25
125000003545 alkoxy group Chemical group 0.000 claims description 24
125000003282 alkyl amino group Chemical group 0.000 claims description 24
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 23
125000004414 alkyl thio group Chemical group 0.000 claims description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
238000012546 transfer Methods 0.000 claims description 22
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
125000004093 cyano group Chemical group *C#N 0.000 claims description 21
125000003396 thiol group Chemical class [H]S* 0.000 claims description 21
125000003277 amino group Chemical group 0.000 claims description 15
125000000623 heterocyclic group Chemical group 0.000 claims description 15
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
125000001931 aliphatic group Chemical group 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
150000004820 halides Chemical class 0.000 claims description 13
125000005843 halogen group Chemical group 0.000 claims description 13
125000001072 heteroaryl group Chemical group 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 11
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
125000004104 aryloxy group Chemical group 0.000 claims description 8
230000002093 peripheral effect Effects 0.000 claims description 8
125000001769 aryl amino group Chemical group 0.000 claims description 7
125000003609 aryl vinyl group Chemical group 0.000 claims description 7
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
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 7
125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
206010063547 Diabetic macroangiopathy Diseases 0.000 claims description 6
206010012689 Diabetic retinopathy Diseases 0.000 claims description 6
208000002705 Glucose Intolerance Diseases 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 6
201000009104 prediabetes syndrome Diseases 0.000 claims description 6
230000002265 prevention Effects 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 4
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
239000003472 antidiabetic agent Substances 0.000 claims description 3
229940126904 hypoglycaemic agent Drugs 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
238000012876 topography Methods 0.000 claims 1
239000008103 glucose Substances 0.000 abstract description 9
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract description 6
239000003814 drug Substances 0.000 abstract description 6
229940079593 drug Drugs 0.000 abstract description 5
230000003389 potentiating effect Effects 0.000 abstract description 2
230000003449 preventive effect Effects 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 183
238000000034 method Methods 0.000 description 79
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
239000007858 starting material Substances 0.000 description 40
239000000243 solution Substances 0.000 description 38
230000000694 effects Effects 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
230000015572 biosynthetic process Effects 0.000 description 32
239000000203 mixture Substances 0.000 description 32
238000003786 synthesis reaction Methods 0.000 description 32
238000005160 1H NMR spectroscopy Methods 0.000 description 30
WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 30
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 29
238000005481 NMR spectroscopy Methods 0.000 description 26
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
150000001299 aldehydes Chemical class 0.000 description 23
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 20
239000000741 silica gel Substances 0.000 description 19
229910002027 silica gel Inorganic materials 0.000 description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
229940125396 insulin Drugs 0.000 description 15
IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 14
RUXHWBMJNBBYNL-UHFFFAOYSA-N 3-hydroxy-1,2-dihydropyrrol-5-one Chemical compound OC1=CC(=O)NC1 RUXHWBMJNBBYNL-UHFFFAOYSA-N 0.000 description 14
102000004877 Insulin Human genes 0.000 description 14
108090001061 Insulin Proteins 0.000 description 14
150000001923 cyclic compounds Chemical class 0.000 description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
229910052740 iodine Inorganic materials 0.000 description 13
229910052700 potassium Inorganic materials 0.000 description 13
239000002904 solvent Substances 0.000 description 13
239000000126 substance Substances 0.000 description 13
RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
238000001914 filtration Methods 0.000 description 12
239000000047 product Substances 0.000 description 11
239000007787 solid Substances 0.000 description 11
238000012360 testing method Methods 0.000 description 11
239000008280 blood Substances 0.000 description 10
210000004369 blood Anatomy 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 10
ZBEGLEYBWGNZJA-UHFFFAOYSA-N 4-dodecoxybenzaldehyde Chemical compound CCCCCCCCCCCCOC1=CC=C(C=O)C=C1 ZBEGLEYBWGNZJA-UHFFFAOYSA-N 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
238000000746 purification Methods 0.000 description 9
ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 8
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
125000004122 cyclic group Chemical group 0.000 description 8
238000000605 extraction Methods 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
239000004698 Polyethylene Substances 0.000 description 7
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
210000001789 adipocyte Anatomy 0.000 description 7
150000002081 enamines Chemical class 0.000 description 7
238000001308 synthesis method Methods 0.000 description 7
238000004809 thin layer chromatography Methods 0.000 description 7
230000032258 transport Effects 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
241000700159 Rattus Species 0.000 description 5
235000011054 acetic acid Nutrition 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
125000004433 nitrogen atom Chemical group N* 0.000 description 5
DOQJUNNMZNNQAD-UHFFFAOYSA-N pyrrolidine-2,4-dione Chemical compound O=C1CNC(=O)C1 DOQJUNNMZNNQAD-UHFFFAOYSA-N 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 4
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
NRKQMDLBMZFWDM-UHFFFAOYSA-N 4-tert-butyl-2-chlorobenzaldehyde Chemical compound CC(C)(C)C1=CC=C(C=O)C(Cl)=C1 NRKQMDLBMZFWDM-UHFFFAOYSA-N 0.000 description 4
235000010469 Glycine max Nutrition 0.000 description 4
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
241001424341 Tara spinosa Species 0.000 description 4
238000007792 addition Methods 0.000 description 4
KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
238000002560 therapeutic procedure Methods 0.000 description 4
229930192474 thiophene Natural products 0.000 description 4
238000005406 washing Methods 0.000 description 4
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 3
FIZIXTUCOMHSRX-UHFFFAOYSA-N 2,4-dibutoxybenzaldehyde Chemical compound CCCCOC1=CC=C(C=O)C(OCCCC)=C1 FIZIXTUCOMHSRX-UHFFFAOYSA-N 0.000 description 3
AUTGLFSBJLERMV-UHFFFAOYSA-N 2-phenylpyrimidine-5-carbaldehyde Chemical compound N1=CC(C=O)=CN=C1C1=CC=CC=C1 AUTGLFSBJLERMV-UHFFFAOYSA-N 0.000 description 3
SYCFYQFCFHKYPI-UHFFFAOYSA-N 4-(2-phenylethynyl)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1C#CC1=CC=CC=C1 SYCFYQFCFHKYPI-UHFFFAOYSA-N 0.000 description 3
MGHIIGWDUVNPPV-UHFFFAOYSA-N 4-(4-nitrophenyl)benzaldehyde Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CC=C(C=O)C=C1 MGHIIGWDUVNPPV-UHFFFAOYSA-N 0.000 description 3
XVBUHGDSGIKMMT-UHFFFAOYSA-N 4-butoxy-2-methoxybenzaldehyde Chemical compound CCCCOC1=CC=C(C=O)C(OC)=C1 XVBUHGDSGIKMMT-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
241000283965 Ochotona princeps Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
239000006285 cell suspension Substances 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
230000002218 hypoglycaemic effect Effects 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
239000012948 isocyanate Substances 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
239000012528 membrane Substances 0.000 description 3
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 3
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
230000008569 process Effects 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000012265 solid product Substances 0.000 description 3
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
208000001072 type 2 diabetes mellitus Diseases 0.000 description 3
235000014101 wine Nutrition 0.000 description 3
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 2
VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 2
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