JP4426792B2

JP4426792B2 - 縮合ベンゼン誘導体および用途

縮合ベンゼン誘導体および用途 Download PDF

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Publication number: JP4426792B2
Authority: JP; Japan
Prior art keywords: group; mixture; optionally substituted; ring; methyl
Prior art date: 2002-08-12
Legal status : Expired - Fee Related

Application number

JP2003291584A

Other languages

English (en)

Japanese (ja)

Other versions

JP2004091486A5 (enExample

JP2004091486A (ja

Inventor

充白石

原　　隆人

雅美日下

直之神崎

哲史山本

敏雄宮脇

Current Assignee

Takeda Pharmaceutical Co Ltd

Original Assignee

Takeda Pharmaceutical Co Ltd

Priority date

2002-08-12

Filing date

2003-08-11

Publication date

2010-03-03

2003-08-11 Application filed by Takeda Pharmaceutical Co Ltd filed Critical Takeda Pharmaceutical Co Ltd

2003-08-11 Priority to JP2003291584A priority Critical patent/JP4426792B2/ja

2004-03-25 Publication of JP2004091486A publication Critical patent/JP2004091486A/ja

2006-09-21 Publication of JP2004091486A5 publication Critical patent/JP2004091486A5/ja

2010-03-03 Application granted granted Critical

2010-03-03 Publication of JP4426792B2 publication Critical patent/JP4426792B2/ja

2023-08-11 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

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125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title description 29
-1 3-hydroxy-2-methyl- 1-pyrrolidinyl Chemical group 0.000 claims description 336
150000001875 compounds Chemical class 0.000 claims description 158
239000003814 drug Substances 0.000 claims description 122
150000003839 salts Chemical class 0.000 claims description 84
239000003795 chemical substances by application Substances 0.000 claims description 62
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 53
229940124011 Androgen receptor agonist Drugs 0.000 claims description 42
206010028980 Neoplasm Diseases 0.000 claims description 40
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 39
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 38
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
125000004093 cyano group Chemical group *C#N 0.000 claims description 34
201000011510 cancer Diseases 0.000 claims description 31
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 30
229940088597 hormone Drugs 0.000 claims description 30
239000005556 hormone Substances 0.000 claims description 30
239000000556 agonist Substances 0.000 claims description 24
XLXSAKCOAKORKW-UHFFFAOYSA-N gonadorelin Chemical group C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 XLXSAKCOAKORKW-UHFFFAOYSA-N 0.000 claims description 23
208000016691 refractory malignant neoplasm Diseases 0.000 claims description 22
206010060862 Prostate cancer Diseases 0.000 claims description 21
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 21
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 15
229910052717 sulfur Inorganic materials 0.000 claims description 12
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
238000011282 treatment Methods 0.000 claims description 9
101000904173 Homo sapiens Progonadoliberin-1 Proteins 0.000 claims description 8
102100024028 Progonadoliberin-1 Human genes 0.000 claims description 8
101000996723 Sus scrofa Gonadotropin-releasing hormone receptor Proteins 0.000 claims description 8
239000000849 selective androgen receptor modulator Substances 0.000 claims description 8
125000004434 sulfur atom Chemical group 0.000 claims description 6
ONJLFPJXEMBCFJ-UHFFFAOYSA-N 4-[3-(2-hydroxypropan-2-yl)-2-methylpyrrolidin-1-yl]naphthalene-1-carbonitrile Chemical compound CC1C(C(C)(C)O)CCN1C1=CC=C(C#N)C2=CC=CC=C12 ONJLFPJXEMBCFJ-UHFFFAOYSA-N 0.000 claims description 4
208000001132 Osteoporosis Diseases 0.000 claims description 4
239000013543 active substance Substances 0.000 claims description 4
LWQKZNNGOSPTCG-UHFFFAOYSA-N 4-(3-hydroxy-2-methylpyrrolidin-1-yl)naphthalene-1-carbonitrile Chemical compound CC1C(O)CCN1C1=CC=C(C#N)C2=CC=CC=C12 LWQKZNNGOSPTCG-UHFFFAOYSA-N 0.000 claims description 3
JSTCOEQWNFSKDJ-UHFFFAOYSA-N 4-(3-methoxy-2-methylpyrrolidin-1-yl)naphthalene-1-carbonitrile Chemical compound CC1C(OC)CCN1C1=CC=C(C#N)C2=CC=CC=C12 JSTCOEQWNFSKDJ-UHFFFAOYSA-N 0.000 claims description 3
230000009245 menopause Effects 0.000 claims description 3
JVHQZMHIDCYVQV-UHFFFAOYSA-N 1-(4-cyanonaphthalen-1-yl)-2-methylpyrrolidine-3-carbonitrile Chemical compound CC1C(C#N)CCN1C1=CC=C(C#N)C2=CC=CC=C12 JVHQZMHIDCYVQV-UHFFFAOYSA-N 0.000 claims description 2
XPNGEQGQTHAJCS-UHFFFAOYSA-N 1-(4-cyanonaphthalen-1-yl)-2-methylpyrrolidine-3-carboxamide Chemical compound CC1C(C(N)=O)CCN1C1=CC=C(C#N)C2=CC=CC=C12 XPNGEQGQTHAJCS-UHFFFAOYSA-N 0.000 claims description 2
238000011321 prophylaxis Methods 0.000 claims description 2
ACYXDSBSDZXJHI-UHFFFAOYSA-N 4-[3-(hydroxymethyl)-2-methylpyrrolidin-1-yl]naphthalene-1-carbonitrile Chemical compound CC1C(CO)CCN1C1=CC=C(C#N)C2=CC=CC=C12 ACYXDSBSDZXJHI-UHFFFAOYSA-N 0.000 claims 1
125000001424 substituent group Chemical group 0.000 description 157
239000000203 mixture Substances 0.000 description 148
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 126
235000002639 sodium chloride Nutrition 0.000 description 94
229940079593 drug Drugs 0.000 description 86
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 86
238000002360 preparation method Methods 0.000 description 76
238000005160 1H NMR spectroscopy Methods 0.000 description 67
125000002252 acyl group Chemical group 0.000 description 64
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
238000000034 method Methods 0.000 description 60
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 54
125000005843 halogen group Chemical group 0.000 description 54
229910052757 nitrogen Inorganic materials 0.000 description 54
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 50
125000000217 alkyl group Chemical group 0.000 description 50
238000010898 silica gel chromatography Methods 0.000 description 50
239000000243 solution Substances 0.000 description 49
125000004433 nitrogen atom Chemical group N* 0.000 description 44
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 40
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
125000003277 amino group Chemical group 0.000 description 34
239000000284 extract Substances 0.000 description 34
239000012267 brine Substances 0.000 description 33
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 33
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 31
239000000126 substance Substances 0.000 description 31
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 30
235000019441 ethanol Nutrition 0.000 description 29
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 29
XLXSAKCOAKORKW-AQJXLSMYSA-N gonadorelin Chemical group C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 XLXSAKCOAKORKW-AQJXLSMYSA-N 0.000 description 29
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
239000003098 androgen Substances 0.000 description 27
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
239000011248 coating agent Substances 0.000 description 25
238000003756 stirring Methods 0.000 description 25
101000857870 Squalus acanthias Gonadoliberin Proteins 0.000 description 24
238000001816 cooling Methods 0.000 description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
101000904177 Clupea pallasii Gonadoliberin-1 Proteins 0.000 description 22
239000000579 Gonadotropin-Releasing Hormone Substances 0.000 description 22
125000003118 aryl group Chemical group 0.000 description 22
125000000623 heterocyclic group Chemical group 0.000 description 22
150000002430 hydrocarbons Chemical group 0.000 description 22
239000000546 pharmaceutical excipient Substances 0.000 description 22
239000007787 solid Substances 0.000 description 22
239000002904 solvent Substances 0.000 description 22
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 21
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 21
125000003710 aryl alkyl group Chemical group 0.000 description 21
210000004027 cell Anatomy 0.000 description 21
229910052801 chlorine Inorganic materials 0.000 description 21
238000002347 injection Methods 0.000 description 21
239000007924 injection Substances 0.000 description 21
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
241000124008 Mammalia Species 0.000 description 19
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 19
125000004453 alkoxycarbonyl group Chemical group 0.000 description 18
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 18
229910052794 bromium Inorganic materials 0.000 description 18
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 18
229910052799 carbon Inorganic materials 0.000 description 18
239000000460 chlorine Substances 0.000 description 18
238000000576 coating method Methods 0.000 description 18
229910052731 fluorine Inorganic materials 0.000 description 18
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 18
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 17
125000004430 oxygen atom Chemical group O* 0.000 description 17
125000000547 substituted alkyl group Chemical group 0.000 description 17
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
125000003545 alkoxy group Chemical group 0.000 description 16
150000001721 carbon Chemical group 0.000 description 16
229940002612 prodrug Drugs 0.000 description 16
239000000651 prodrug Substances 0.000 description 16
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 16
238000001356 surgical procedure Methods 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
239000002246 antineoplastic agent Substances 0.000 description 15
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
239000012044 organic layer Substances 0.000 description 15
229920000642 polymer Polymers 0.000 description 15
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 14
229920002472 Starch Polymers 0.000 description 14
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 14
125000006615 aromatic heterocyclic group Chemical group 0.000 description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 14
239000011737 fluorine Substances 0.000 description 14
239000000314 lubricant Substances 0.000 description 14
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
239000008107 starch Substances 0.000 description 14
235000019698 starch Nutrition 0.000 description 14
229940124597 therapeutic agent Drugs 0.000 description 14
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
230000009471 action Effects 0.000 description 13
125000003342 alkenyl group Chemical group 0.000 description 13
229920002678 cellulose Polymers 0.000 description 13
239000003405 delayed action preparation Substances 0.000 description 13
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 description 13
239000012729 immediate-release (IR) formulation Substances 0.000 description 13
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 13
229920000036 polyvinylpyrrolidone Polymers 0.000 description 13
239000001267 polyvinylpyrrolidone Substances 0.000 description 13
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 13
229920006395 saturated elastomer Polymers 0.000 description 13
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
235000010980 cellulose Nutrition 0.000 description 12
239000001913 cellulose Substances 0.000 description 12
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 12
201000010099 disease Diseases 0.000 description 12
239000008187 granular material Substances 0.000 description 12
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 12
239000001863 hydroxypropyl cellulose Substances 0.000 description 12
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 12
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 12
235000010355 mannitol Nutrition 0.000 description 12
239000008194 pharmaceutical composition Substances 0.000 description 12
229920001223 polyethylene glycol Polymers 0.000 description 12
239000003381 stabilizer Substances 0.000 description 12
239000002202 Polyethylene glycol Substances 0.000 description 11
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 11
125000005530 alkylenedioxy group Chemical group 0.000 description 11
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 11
229930195733 hydrocarbon Natural products 0.000 description 11
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 11
239000002198 insoluble material Substances 0.000 description 11
239000012452 mother liquor Substances 0.000 description 11
230000003637 steroidlike Effects 0.000 description 11
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 10
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 10
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 10
HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 10
229930006000 Sucrose Natural products 0.000 description 10
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 10
239000000654 additive Substances 0.000 description 10
239000012300 argon atmosphere Substances 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
125000002619 bicyclic group Chemical group 0.000 description 10
235000015165 citric acid Nutrition 0.000 description 10
230000000694 effects Effects 0.000 description 10
239000002434 gonadorelin derivative Substances 0.000 description 10
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 10
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 10
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 10
125000006239 protecting group Chemical group 0.000 description 10
229960004793 sucrose Drugs 0.000 description 10
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 10
229940086542 triethylamine Drugs 0.000 description 10
125000004844 (C1-C6) alkoxyimino group Chemical group 0.000 description 9
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 9
239000004215 Carbon black (E152) Substances 0.000 description 9
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 9
230000010261 cell growth Effects 0.000 description 9
239000007884 disintegrant Substances 0.000 description 9
239000003755 preservative agent Substances 0.000 description 9
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 8
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 8
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 8
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 8
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
229910052783 alkali metal Inorganic materials 0.000 description 8
125000000304 alkynyl group Chemical group 0.000 description 8
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 8
125000005161 aryl oxy carbonyl group Chemical group 0.000 description 8
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
239000011230 binding agent Substances 0.000 description 8
239000001768 carboxy methyl cellulose Substances 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
125000000753 cycloalkyl group Chemical group 0.000 description 8
230000001419 dependent effect Effects 0.000 description 8
238000001035 drying Methods 0.000 description 8
238000009472 formulation Methods 0.000 description 8
239000008101 lactose Substances 0.000 description 8
239000010410 layer Substances 0.000 description 8
238000002156 mixing Methods 0.000 description 8
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