KR100424933B1 - 아미노티아졸유도체,이를함유하는의약및이화합물의중간체 - Google Patents

Info

Publication number

KR100424933B1

KR100424933B1 KR1019970707808A KR19970707808A KR100424933B1 KR 100424933 B1 KR100424933 B1 KR 100424933B1 KR 1019970707808 A KR1019970707808 A KR 1019970707808A KR 19970707808 A KR19970707808 A KR 19970707808A KR 100424933 B1 KR100424933 B1 KR 100424933B1

Authority

KR

South Korea

Prior art keywords

group

alkyl

amino

carbon atoms

thiazole

Prior art date

1995-05-18

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Lifetime

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 103
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 title claims abstract description 14
• 239000003814 drug Substances 0.000 title claims abstract description 13
• 239000000543 intermediate Substances 0.000 title description 23
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 91
• 125000003277 amino group Chemical group 0.000 claims abstract description 47
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 43
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 29
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 26
• 125000005843 halogen group Chemical group 0.000 claims abstract description 19
• 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 15
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
• 210000001035 gastrointestinal tract Anatomy 0.000 claims abstract description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 54
• 125000004432 carbon atom Chemical group C* 0.000 claims description 29
• 239000000203 mixture Substances 0.000 claims description 24
• 150000003839 salts Chemical class 0.000 claims description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
• 125000004122 cyclic group Chemical group 0.000 claims description 10
• 125000003386 piperidinyl group Chemical group 0.000 claims description 10
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 229920006395 saturated elastomer Polymers 0.000 claims description 8
• 125000003282 alkyl amino group Chemical group 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• 238000011282 treatment Methods 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• 208000004998 Abdominal Pain Diseases 0.000 claims description 3
• 206010000060 Abdominal distension Diseases 0.000 claims description 3
• 208000007882 Gastritis Diseases 0.000 claims description 3
• 206010028813 Nausea Diseases 0.000 claims description 3
• 206010047700 Vomiting Diseases 0.000 claims description 3
• 208000022531 anorexia Diseases 0.000 claims description 3
• 208000023652 chronic gastritis Diseases 0.000 claims description 3
• 206010061428 decreased appetite Diseases 0.000 claims description 3
• 208000035475 disorder Diseases 0.000 claims description 3
• 201000006549 dyspepsia Diseases 0.000 claims description 3
• 208000024798 heartburn Diseases 0.000 claims description 3
• 230000008693 nausea Effects 0.000 claims description 3
• 208000000689 peptic esophagitis Diseases 0.000 claims description 3
• 230000002265 prevention Effects 0.000 claims description 3
• 230000008673 vomiting Effects 0.000 claims description 3
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
• 239000004480 active ingredient Substances 0.000 claims description 2
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000006165 cyclic alkyl group Chemical class 0.000 claims description 2
• 238000005984 hydrogenation reaction Methods 0.000 claims description 2
• 125000004043 oxo group Chemical group O=* 0.000 claims description 2
• 239000008194 pharmaceutical composition Substances 0.000 claims description 2
• 229940124597 therapeutic agent Drugs 0.000 claims description 2
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 6
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 4
• 125000005699 methyleneoxy group Chemical group [H]C([H])([*:1])O[*:2] 0.000 claims 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
• 210000001015 abdomen Anatomy 0.000 claims 1
• 230000002159 abnormal effect Effects 0.000 claims 1
• 201000001421 hyperglycemia Diseases 0.000 claims 1
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
• 230000000069 prophylactic effect Effects 0.000 claims 1
• 238000011321 prophylaxis Methods 0.000 claims 1
• 238000002360 preparation method Methods 0.000 abstract description 13
• 230000000694 effects Effects 0.000 abstract description 7
• 125000004430 oxygen atom Chemical group O* 0.000 abstract description 2
• 230000001330 gastroprokinetic effect Effects 0.000 abstract 1
• -1 tert.-butyl Chemical group 0.000 description 508
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
• 238000006243 chemical reaction Methods 0.000 description 39
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 26
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
• 239000000243 solution Substances 0.000 description 16
• 239000013078 crystal Substances 0.000 description 14
• 238000000034 method Methods 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 239000011541 reaction mixture Substances 0.000 description 12
• 238000006467 substitution reaction Methods 0.000 description 12
• 150000007979 thiazole derivatives Chemical class 0.000 description 11
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
• 238000001914 filtration Methods 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
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 9
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 9
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
• 239000002904 solvent Substances 0.000 description 8
• 239000012458 free base Substances 0.000 description 7
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 125000004093 cyano group Chemical group *C#N 0.000 description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
• 125000004448 alkyl carbonyl group Chemical group 0.000 description 5
• 239000002585 base Substances 0.000 description 5
• 125000006309 butyl amino group Chemical group 0.000 description 5
• 238000007796 conventional method Methods 0.000 description 5
• 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 5
• 230000005176 gastrointestinal motility Effects 0.000 description 5
• 238000004519 manufacturing process Methods 0.000 description 5
• AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 5
• 125000001424 substituent group Chemical group 0.000 description 5
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• 239000002253 acid Substances 0.000 description 4
• 230000009471 action Effects 0.000 description 4
• 150000001350 alkyl halides Chemical class 0.000 description 4
• 125000004103 aminoalkyl group Chemical group 0.000 description 4
• 239000007864 aqueous solution Substances 0.000 description 4
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• 201000010099 disease Diseases 0.000 description 4
• LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• 230000008569 process Effects 0.000 description 4
• 125000006308 propyl amino group Chemical group 0.000 description 4
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
• VIOBGCWEHLRBEP-UHFFFAOYSA-N 3,4-dimethoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1OC VIOBGCWEHLRBEP-UHFFFAOYSA-N 0.000 description 3
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 125000005122 aminoalkylamino group Chemical group 0.000 description 3
• 239000001913 cellulose Substances 0.000 description 3
• 229920002678 cellulose Polymers 0.000 description 3
• 229940079593 drug Drugs 0.000 description 3
• BWDNVLPYCMAUGL-UHFFFAOYSA-N ethyl 2-[(2,4,5-trimethoxybenzoyl)amino]-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(NC(=O)C=2C(=CC(OC)=C(OC)C=2)OC)=N1 BWDNVLPYCMAUGL-UHFFFAOYSA-N 0.000 description 3
• WLQDTBDHAVNKQJ-UHFFFAOYSA-N ethyl 2-[(3,4-dimethoxybenzoyl)amino]-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(NC(=O)C=2C=C(OC)C(OC)=CC=2)=N1 WLQDTBDHAVNKQJ-UHFFFAOYSA-N 0.000 description 3
• 235000019253 formic acid Nutrition 0.000 description 3
• 238000009472 formulation Methods 0.000 description 3
• 239000008187 granular material Substances 0.000 description 3
• 238000002844 melting Methods 0.000 description 3
• 230000008018 melting Effects 0.000 description 3
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
• 238000010898 silica gel chromatography Methods 0.000 description 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
• 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 2
• 125000004907 1,2-dimethylbutylamino group Chemical group CC(C(CC)C)N* 0.000 description 2
• UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical group CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
• NJPNBZKMVUGMAU-UHFFFAOYSA-N 2-[(2,4,5-trimethoxybenzoyl)amino]-1,3-thiazole-4-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC(OC)=C1C(=O)NC1=NC(C(O)=O)=CS1 NJPNBZKMVUGMAU-UHFFFAOYSA-N 0.000 description 2
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
• 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 description 2
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• 241000699670 Mus sp. Species 0.000 description 2
• IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
• FKZCLFRXTDSEFX-UHFFFAOYSA-N acetic acid;ethyl 2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-1,3-thiazole-4-carboxylate Chemical compound CC(O)=O.CCOC(=O)C1=CSC(NC(=O)C=2C(=CC(OC)=C(OC)C=2)O)=N1 FKZCLFRXTDSEFX-UHFFFAOYSA-N 0.000 description 2
• 150000001299 aldehydes Chemical class 0.000 description 2
• 238000005804 alkylation reaction Methods 0.000 description 2
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 229910052799 carbon Inorganic materials 0.000 description 2
• 125000006317 cyclopropyl amino group Chemical group 0.000 description 2
• 238000006900 dealkylation reaction Methods 0.000 description 2
• 239000012954 diazonium Substances 0.000 description 2
• 150000001989 diazonium salts Chemical class 0.000 description 2
• 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
• FPJZLOPPFYUYAQ-UHFFFAOYSA-N ethyl 2-(methylamino)-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(NC)=N1 FPJZLOPPFYUYAQ-UHFFFAOYSA-N 0.000 description 2
• BXPHEUUYVZZOCL-UHFFFAOYSA-N ethyl 2-[(3,4-dimethoxybenzoyl)-methylamino]-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(N(C)C(=O)C=2C=C(OC)C(OC)=CC=2)=N1 BXPHEUUYVZZOCL-UHFFFAOYSA-N 0.000 description 2
• 229940015043 glyoxal Drugs 0.000 description 2
• 229910052736 halogen Inorganic materials 0.000 description 2
• 150000002367 halogens Chemical class 0.000 description 2
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
• 239000005457 ice water Substances 0.000 description 2
• 125000002632 imidazolidinyl group Chemical group 0.000 description 2
• 239000007924 injection Substances 0.000 description 2
• 238000002347 injection Methods 0.000 description 2
• 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
• 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 2
• 125000003965 isoxazolidinyl group Chemical group 0.000 description 2
• 239000010410 layer Substances 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
• BLJLTUSYGJUUAD-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-(methylamino)-1,3-thiazole-4-carboxamide Chemical compound CNC1=NC(C(=O)NCCN(C)C)=CS1 BLJLTUSYGJUUAD-UHFFFAOYSA-N 0.000 description 2
• URJRCHXKTZSVQD-UHFFFAOYSA-N n-[2-[di(propan-2-yl)amino]ethyl]-2-[(4-hydroxy-3-methoxybenzoyl)amino]-1,3-thiazole-4-carboxamide;dihydrochloride Chemical compound Cl.Cl.C1=C(O)C(OC)=CC(C(=O)NC=2SC=C(N=2)C(=O)NCCN(C(C)C)C(C)C)=C1 URJRCHXKTZSVQD-UHFFFAOYSA-N 0.000 description 2
• 125000000160 oxazolidinyl group Chemical group 0.000 description 2
• 229910052760 oxygen Inorganic materials 0.000 description 2
• 239000001301 oxygen Substances 0.000 description 2
• 125000003884 phenylalkyl group Chemical group 0.000 description 2
• 125000005543 phthalimide group Chemical group 0.000 description 2
• 229910000027 potassium carbonate Inorganic materials 0.000 description 2
• 235000011181 potassium carbonates Nutrition 0.000 description 2
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
• KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
• 125000004076 pyridyl group Chemical group 0.000 description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
• 238000006722 reduction reaction Methods 0.000 description 2
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
• 235000017557 sodium bicarbonate Nutrition 0.000 description 2
• 229910052717 sulfur Inorganic materials 0.000 description 2
• 125000004434 sulfur atom Chemical group 0.000 description 2
• 239000000725 suspension Substances 0.000 description 2
• 208000024891 symptom Diseases 0.000 description 2
• 125000001984 thiazolidinyl group Chemical group 0.000 description 2
• JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
• VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
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