JP2000226373A

JP2000226373A - アミン誘導体、その製造法および剤

アミン誘導体、その製造法および剤

Info

Publication number: JP2000226373A
Authority: JP; Japan
Prior art keywords: alkyl; methyl; ring; substituent; ethyl acetate
Prior art date: 1998-04-08
Legal status : Abandoned

Application number

JP11100828A

Other languages

English (en)

Japanese (ja)

Other versions

JP2000226373A5 (enrdf_load_stackoverflow

Inventor

Nobuhiro Suzuki

伸宏鈴木

Kaneyoshi Katou

金芳加藤

Shiro Takekawa

志郎竹河

Atsushi Terauchi

淳寺内

Satoshi Endo

聡史遠藤

Current Assignee

Takeda Pharmaceutical Co Ltd

Original Assignee

Takeda Chemical Industries Ltd

Priority date

1998-04-08

Filing date

1999-04-08

Publication date

2000-08-15

1999-04-08 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1999-04-08 Priority to JP11100828A priority Critical patent/JP2000226373A/ja

2000-08-15 Publication of JP2000226373A publication Critical patent/JP2000226373A/ja

2006-04-27 Publication of JP2000226373A5 publication Critical patent/JP2000226373A5/ja

Status Abandoned legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title abstract description 13
150000001412 amines Chemical class 0.000 title abstract description 5
150000001875 compounds Chemical class 0.000 claims abstract description 300
125000000217 alkyl group Chemical group 0.000 claims abstract description 120
125000003118 aryl group Chemical group 0.000 claims abstract description 115
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 23
108050001286 Somatostatin Receptor Proteins 0.000 claims abstract description 17
102000011096 Somatostatin receptor Human genes 0.000 claims abstract description 17
125000006850 spacer group Chemical group 0.000 claims abstract description 14
125000006574 non-aromatic ring group Chemical group 0.000 claims abstract description 13
230000027455 binding Effects 0.000 claims abstract description 12
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 11
125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims abstract 8
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract 6
-1 5-oxazolyl Chemical group 0.000 claims description 593
125000001424 substituent group Chemical group 0.000 claims description 191
150000003839 salts Chemical class 0.000 claims description 110
239000000203 mixture Substances 0.000 claims description 86
125000003545 alkoxy group Chemical group 0.000 claims description 63
125000005843 halogen group Chemical group 0.000 claims description 61
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
238000000034 method Methods 0.000 claims description 43
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 35
125000002947 alkylene group Chemical group 0.000 claims description 33
229910052757 nitrogen Inorganic materials 0.000 claims description 33
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 33
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 29
125000004433 nitrogen atom Chemical group N* 0.000 claims description 29
125000003710 aryl alkyl group Chemical group 0.000 claims description 28
125000004093 cyano group Chemical group *C#N 0.000 claims description 27
125000005129 aryl carbonyl group Chemical group 0.000 claims description 26
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 26
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 25
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 24
125000000623 heterocyclic group Chemical group 0.000 claims description 24
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 23
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 20
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 20
125000004450 alkenylene group Chemical group 0.000 claims description 20
239000003814 drug Substances 0.000 claims description 20
206010028980 Neoplasm Diseases 0.000 claims description 19
125000002252 acyl group Chemical group 0.000 claims description 18
125000005530 alkylenedioxy group Chemical group 0.000 claims description 18
229910005965 SO 2 Inorganic materials 0.000 claims description 17
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 17
125000004429 atom Chemical group 0.000 claims description 16
125000004442 acylamino group Chemical group 0.000 claims description 15
125000004104 aryloxy group Chemical group 0.000 claims description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 12
239000003112 inhibitor Substances 0.000 claims description 12
125000003003 spiro group Chemical group 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
229940124597 therapeutic agent Drugs 0.000 claims description 11
206010012601 diabetes mellitus Diseases 0.000 claims description 10
125000004076 pyridyl group Chemical group 0.000 claims description 9
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
229940002612 prodrug Drugs 0.000 claims description 7
239000000651 prodrug Substances 0.000 claims description 7
125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
208000010412 Glaucoma Diseases 0.000 claims description 5
239000000470 constituent Substances 0.000 claims description 5
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
208000002249 Diabetes Complications Diseases 0.000 claims description 4
206010012655 Diabetic complications Diseases 0.000 claims description 4
229910052727 yttrium Inorganic materials 0.000 claims description 4
125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 3
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 3
CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 3
206010000599 Acromegaly Diseases 0.000 claims description 3
229940123051 Somatostatin receptor agonist Drugs 0.000 claims description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 3
230000000202 analgesic effect Effects 0.000 claims description 3
229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
230000000069 prophylactic effect Effects 0.000 claims description 3
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
229940121856 Somatostatin receptor antagonist Drugs 0.000 claims description 2
150000003857 carboxamides Chemical class 0.000 claims description 2
201000010099 disease Diseases 0.000 abstract description 17
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 17
230000028327 secretion Effects 0.000 abstract description 11
229940088597 hormone Drugs 0.000 abstract description 8
239000005556 hormone Substances 0.000 abstract description 8
230000002401 inhibitory effect Effects 0.000 abstract description 8
230000005856 abnormality Effects 0.000 abstract description 5
230000010261 cell growth Effects 0.000 abstract description 2
238000012546 transfer Methods 0.000 abstract description 2
241001601725 Sthenias Species 0.000 abstract 1
210000004962 mammalian cell Anatomy 0.000 abstract 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
230000001988 toxicity Effects 0.000 abstract 1
231100000419 toxicity Toxicity 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 516
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 273
239000000243 solution Substances 0.000 description 184
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 154
238000006243 chemical reaction Methods 0.000 description 146
239000002904 solvent Substances 0.000 description 134
238000002844 melting Methods 0.000 description 113
230000008018 melting Effects 0.000 description 113
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 111
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 111
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 99
235000002639 sodium chloride Nutrition 0.000 description 98
229910001868 water Inorganic materials 0.000 description 98
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 97
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 89
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 78
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 73
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
239000012044 organic layer Substances 0.000 description 60
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 46
238000001953 recrystallisation Methods 0.000 description 46
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 45
239000013078 crystal Substances 0.000 description 43
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 34
238000003756 stirring Methods 0.000 description 34
125000005115 alkyl carbamoyl group Chemical group 0.000 description 30
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 30
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 28
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
239000000460 chlorine Substances 0.000 description 28
229910052801 chlorine Inorganic materials 0.000 description 28
238000005160 1H NMR spectroscopy Methods 0.000 description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
238000010992 reflux Methods 0.000 description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
238000001816 cooling Methods 0.000 description 22
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 21
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 21
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 21
229910052794 bromium Inorganic materials 0.000 description 21
239000011737 fluorine Substances 0.000 description 21
229910052731 fluorine Inorganic materials 0.000 description 21
238000010898 silica gel chromatography Methods 0.000 description 20
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 19
125000005431 alkyl carboxamide group Chemical group 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
239000002585 base Substances 0.000 description 18
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 16
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 16
230000003287 optical effect Effects 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 15
229910052739 hydrogen Inorganic materials 0.000 description 15
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
239000012442 inert solvent Substances 0.000 description 15
125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 14
125000005196 alkyl carbonyloxy group Chemical group 0.000 description 14
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 14
238000004440 column chromatography Methods 0.000 description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
235000017557 sodium bicarbonate Nutrition 0.000 description 14
238000011282 treatment Methods 0.000 description 14
125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 description 13
125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 13
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 13
125000006615 aromatic heterocyclic group Chemical group 0.000 description 13
125000005161 aryl oxy carbonyl group Chemical group 0.000 description 13
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 13
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 12
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 12
102000018997 Growth Hormone Human genes 0.000 description 12
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
102000005157 Somatostatin Human genes 0.000 description 12
108010056088 Somatostatin Proteins 0.000 description 12
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 12
229910052784 alkaline earth metal Inorganic materials 0.000 description 12
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 12
239000003054 catalyst Substances 0.000 description 12
239000003795 chemical substances by application Substances 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
239000003480 eluent Substances 0.000 description 12
125000005842 heteroatom Chemical group 0.000 description 12
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 12
239000011259 mixed solution Substances 0.000 description 12
NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 description 12
229960000553 somatostatin Drugs 0.000 description 12
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 11
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
229910052783 alkali metal Inorganic materials 0.000 description 11
125000005116 aryl carbamoyl group Chemical group 0.000 description 11
XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 11
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 11
239000000706 filtrate Substances 0.000 description 11
239000000122 growth hormone Substances 0.000 description 11
150000002430 hydrocarbons Chemical group 0.000 description 11
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 11
238000002360 preparation method Methods 0.000 description 11
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
229920006395 saturated elastomer Polymers 0.000 description 11
239000012312 sodium hydride Substances 0.000 description 11
229910000104 sodium hydride Inorganic materials 0.000 description 11
229910052717 sulfur Inorganic materials 0.000 description 11
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 10
206010012735 Diarrhoea Diseases 0.000 description 10
108010051696 Growth Hormone Proteins 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 10
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
150000001408 amides Chemical class 0.000 description 10
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 10
238000001035 drying Methods 0.000 description 10
239000001257 hydrogen Substances 0.000 description 10
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 10
229910052987 metal hydride Inorganic materials 0.000 description 10
150000004681 metal hydrides Chemical class 0.000 description 10
125000004430 oxygen atom Chemical group O* 0.000 description 10
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 10
125000004742 propyloxycarbonyl group Chemical group 0.000 description 10
239000000126 substance Substances 0.000 description 10
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 9
238000005917 acylation reaction Methods 0.000 description 9
150000001340 alkali metals Chemical class 0.000 description 9
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
238000001914 filtration Methods 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
235000011181 potassium carbonates Nutrition 0.000 description 9
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 8
MQDSLTHIZQWWLE-UHFFFAOYSA-N 3-[3-(1-benzofuran-2-yl)-1,2,4-oxadiazol-5-yl]propanoic acid Chemical compound O1C(CCC(=O)O)=NC(C=2OC3=CC=CC=C3C=2)=N1 MQDSLTHIZQWWLE-UHFFFAOYSA-N 0.000 description 8
125000006618 5- to 10-membered aromatic heterocyclic group Chemical group 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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 8
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 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
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