TWI488854B - 二苯并噻氮呯衍生物及其用途 - Google Patents

Info

Publication number

TWI488854B

TWI488854B TW098120494A TW98120494A TWI488854B TW I488854 B TWI488854 B TW I488854B TW 098120494 A TW098120494 A TW 098120494A TW 98120494 A TW98120494 A TW 98120494A TW I488854 B TWI488854 B TW I488854B

Authority

TW

Taiwan

Prior art keywords

fluoro

dibenzo

compound

thiazepine

formula

Prior art date

2008-06-20

Links

• Espacenet
• Global Dossier
• Discuss

• 150000008509 dibenzothiazepines Chemical class 0.000 title 1
• 238000000034 method Methods 0.000 claims description 51
• -1 5-fluoro-2-(2-nitro-phenylthio)-benzene Ethyl formate Chemical compound 0.000 claims description 47
• 150000003839 salts Chemical class 0.000 claims description 43
• 208000020925 Bipolar disease Diseases 0.000 claims description 30
• 238000011282 treatment Methods 0.000 claims description 29
• 239000003814 drug Substances 0.000 claims description 27
• CXKQSMUCGLKJEI-UHFFFAOYSA-N 8-fluoro-6-piperazin-1-ylbenzo[b][1,4]benzothiazepine Chemical compound C12=CC(F)=CC=C2SC2=CC=CC=C2N=C1N1CCNCC1 CXKQSMUCGLKJEI-UHFFFAOYSA-N 0.000 claims description 24
• UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims description 21
• 201000000980 schizophrenia Diseases 0.000 claims description 20
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 18
• 238000006243 chemical reaction Methods 0.000 claims description 18
• 208000020016 psychiatric disease Diseases 0.000 claims description 14
• 208000019022 Mood disease Diseases 0.000 claims description 11
• 239000002585 base Substances 0.000 claims description 11
• 208000019901 Anxiety disease Diseases 0.000 claims description 10
• 150000002148 esters Chemical class 0.000 claims description 10
• 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 claims description 8
• RFXCQLRFGHQGCI-UHFFFAOYSA-N 6-chloro-8-fluorobenzo[b][1,4]benzothiazepine Chemical compound N1=C(Cl)C2=CC(F)=CC=C2SC2=CC=CC=C21 RFXCQLRFGHQGCI-UHFFFAOYSA-N 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 230000008569 process Effects 0.000 claims description 7
• BHJJFXMGSTZHIG-UHFFFAOYSA-N 8-fluoro-5h-benzo[b][1,4]benzothiazepin-6-one Chemical compound N1C(=O)C2=CC(F)=CC=C2SC2=CC=CC=C21 BHJJFXMGSTZHIG-UHFFFAOYSA-N 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 5
• PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• SWLWFGHLXXGBNA-UHFFFAOYSA-N 4-fluoro-2-phenylsulfanylaniline Chemical compound NC1=CC=C(F)C=C1SC1=CC=CC=C1 SWLWFGHLXXGBNA-UHFFFAOYSA-N 0.000 claims description 3
• VKHYKHAWFZNIKB-UHFFFAOYSA-N benzo[b][1,4]benzothiazepine Chemical compound C1=NC2=CC=CC=C2SC2=CC=CC=C21 VKHYKHAWFZNIKB-UHFFFAOYSA-N 0.000 claims description 3
• BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 claims description 2
• VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 claims description 2
• OKIHXNKYYGUVTE-UHFFFAOYSA-N 4-Fluorothiophenol Chemical compound FC1=CC=C(S)C=C1 OKIHXNKYYGUVTE-UHFFFAOYSA-N 0.000 claims description 2
• HFANPBYTXDKUDJ-UHFFFAOYSA-N 4-fluoro-1-nitro-2-phenylsulfanylbenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1SC1=CC=CC=C1 HFANPBYTXDKUDJ-UHFFFAOYSA-N 0.000 claims description 2
• MJLXBSNNVFYQFP-UHFFFAOYSA-N CCOC(=O)C1=C(C=CC(=C1)F)C2=CC3=CC=CC=C3N2 Chemical compound CCOC(=O)C1=C(C=CC(=C1)F)C2=CC3=CC=CC=C3N2 MJLXBSNNVFYQFP-UHFFFAOYSA-N 0.000 claims description 2
• 229910052783 alkali metal Inorganic materials 0.000 claims description 2
• 150000001340 alkali metals Chemical class 0.000 claims description 2
• OBCJCDDVWWAXJW-UHFFFAOYSA-N ethyl 2-(2-aminophenyl)sulfanyl-5-fluorobenzoate Chemical compound CCOC(=O)C1=CC(F)=CC=C1SC1=CC=CC=C1N OBCJCDDVWWAXJW-UHFFFAOYSA-N 0.000 claims description 2
• UDBLTZWJCWPYBA-UHFFFAOYSA-N methyl 2,5-difluorobenzoate Chemical compound COC(=O)C1=CC(F)=CC=C1F UDBLTZWJCWPYBA-UHFFFAOYSA-N 0.000 claims description 2
• ZAEAPAVGRSYYRT-UHFFFAOYSA-N phenyl n-[2-(4-fluorophenyl)sulfanylphenyl]carbamate Chemical compound C1=CC(F)=CC=C1SC1=CC=CC=C1NC(=O)OC1=CC=CC=C1 ZAEAPAVGRSYYRT-UHFFFAOYSA-N 0.000 claims description 2
• 230000009467 reduction Effects 0.000 claims description 2
• 230000003340 mental effect Effects 0.000 claims 3
• JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 claims 1
• FBIATHVJVUXRQJ-UHFFFAOYSA-N C1=CC=C(C(=C1)[N+](=O)[O-])SC2=CC=CC(=C2)F Chemical compound C1=CC=C(C(=C1)[N+](=O)[O-])SC2=CC=CC(=C2)F FBIATHVJVUXRQJ-UHFFFAOYSA-N 0.000 claims 1
• XHUNKCWICZXHKQ-UHFFFAOYSA-N ethyl 5-fluoro-2-(2-nitrophenyl)sulfanylbenzoate Chemical compound CCOC(=O)C1=CC(F)=CC=C1SC1=CC=CC=C1[N+]([O-])=O XHUNKCWICZXHKQ-UHFFFAOYSA-N 0.000 claims 1
• PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims 1
• 238000007363 ring formation reaction Methods 0.000 claims 1
• 239000003451 thiazide diuretic agent Substances 0.000 claims 1
• 150000001875 compounds Chemical class 0.000 description 106
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 41
• 239000000203 mixture Substances 0.000 description 31
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 235000019439 ethyl acetate Nutrition 0.000 description 19
• 125000000217 alkyl group Chemical group 0.000 description 16
• 229940079593 drug Drugs 0.000 description 16
• 239000002207 metabolite Substances 0.000 description 16
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
• 102000008092 Norepinephrine Plasma Membrane Transport Proteins Human genes 0.000 description 15
• 108010049586 Norepinephrine Plasma Membrane Transport Proteins Proteins 0.000 description 15
• 230000002829 reductive effect Effects 0.000 description 15
• 230000000694 effects Effects 0.000 description 14
• 239000000243 solution Substances 0.000 description 14
• 125000003118 aryl group Chemical group 0.000 description 13
• 239000011541 reaction mixture Substances 0.000 description 13
• 239000007787 solid Substances 0.000 description 13
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
• 230000008485 antagonism Effects 0.000 description 12
• 239000003960 organic solvent Substances 0.000 description 12
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 11
• 239000000725 suspension Substances 0.000 description 11
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
• 206010026749 Mania Diseases 0.000 description 10
• 239000004480 active ingredient Substances 0.000 description 10
• 238000002360 preparation method Methods 0.000 description 10
• 239000002904 solvent Substances 0.000 description 10
• 238000003786 synthesis reaction Methods 0.000 description 10
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
• 238000005481 NMR spectroscopy Methods 0.000 description 9
• 239000002253 acid Substances 0.000 description 9
• 230000015572 biosynthetic process Effects 0.000 description 9
• 238000005859 coupling reaction Methods 0.000 description 9
• 125000000753 cycloalkyl group Chemical group 0.000 description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
• 238000004128 high performance liquid chromatography Methods 0.000 description 9
• KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 9
• 229960005017 olanzapine Drugs 0.000 description 9
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
• 241001465754 Metazoa Species 0.000 description 8
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• 125000001072 heteroaryl group Chemical group 0.000 description 8
• 125000000592 heterocycloalkyl group Chemical group 0.000 description 8
• 239000000543 intermediate Substances 0.000 description 8
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• 239000003153 chemical reaction reagent Substances 0.000 description 7
• 239000002552 dosage form Substances 0.000 description 7
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• 208000024891 symptom Diseases 0.000 description 7
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• KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 6
• 241000124008 Mammalia Species 0.000 description 6
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• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 239000005557 antagonist Substances 0.000 description 6
• 125000004432 carbon atom Chemical group C* 0.000 description 6
• FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 6
• 230000008878 coupling Effects 0.000 description 6
• 238000010168 coupling process Methods 0.000 description 6
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• PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 6
• 229960004431 quetiapine Drugs 0.000 description 6
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