NO333505B1 - 4,4-difluor-1,2,3,4-tetrahydro-5H-1-benzazepinderivat eller salt derav, og anvendelse derav for fremstilling av et medikament - Google Patents
4,4-difluor-1,2,3,4-tetrahydro-5H-1-benzazepinderivat eller salt derav, og anvendelse derav for fremstilling av et medikament Download PDFInfo
- Publication number
- NO333505B1 NO333505B1 NO20055602A NO20055602A NO333505B1 NO 333505 B1 NO333505 B1 NO 333505B1 NO 20055602 A NO20055602 A NO 20055602A NO 20055602 A NO20055602 A NO 20055602A NO 333505 B1 NO333505 B1 NO 333505B1
- Authority
- NO
- Norway
- Prior art keywords
- tetrahydro
- trifluoromethyl
- compound
- ylidene
- benzoyl
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims abstract description 29
- 239000003814 drug Substances 0.000 title claims description 27
- DTSDJGNXLLPHFA-UHFFFAOYSA-N 4,4-difluoro-1,2,3,5-tetrahydro-1-benzazepine Chemical class C1C(F)(F)CCNC2=CC=CC=C21 DTSDJGNXLLPHFA-UHFFFAOYSA-N 0.000 title abstract description 15
- 238000002360 preparation method Methods 0.000 title description 18
- 201000010064 diabetes insipidus Diseases 0.000 claims abstract description 12
- 206010029446 nocturia Diseases 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 136
- 229940079593 drug Drugs 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 208000003450 Neurogenic Diabetes Insipidus Diseases 0.000 claims description 11
- 208000028235 central diabetes insipidus Diseases 0.000 claims description 11
- 201000005119 neurohypophyseal diabetes insipidus Diseases 0.000 claims description 11
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- CXOCDYOSOJLLRS-AQTBWJFISA-N (2z)-2-[1-[4-(2,2-difluoropropoxy)-2-(trifluoromethyl)benzoyl]-4,4-difluoro-2,3-dihydro-1-benzazepin-5-ylidene]-n-(2-hydroxyethyl)acetamide Chemical compound FC(F)(F)C1=CC(OCC(F)(F)C)=CC=C1C(=O)N1C2=CC=CC=C2C(=C/C(=O)NCCO)/C(F)(F)CC1 CXOCDYOSOJLLRS-AQTBWJFISA-N 0.000 claims description 3
- VSXSHTIGQAUGMW-VCRXTVNUSA-N (2z)-n-(2-hydroxyethyl)-2-[4,4,7-trifluoro-1-[4-[(2r)-2-fluoropropoxy]-2-(trifluoromethyl)benzoyl]-2,3-dihydro-1-benzazepin-5-ylidene]acetamide Chemical compound FC(F)(F)C1=CC(OC[C@H](F)C)=CC=C1C(=O)N1C2=CC=C(F)C=C2C(=C/C(=O)NCCO)/C(F)(F)CC1 VSXSHTIGQAUGMW-VCRXTVNUSA-N 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- JMCFRZPWDILQBV-PDGQHHTCSA-N (2z)-2-[1-[4-(2,2-difluoropropoxy)-2-(trifluoromethyl)benzoyl]-4,4,7-trifluoro-2,3-dihydro-1-benzazepin-5-ylidene]-n-(2-hydroxyethyl)acetamide Chemical compound FC(F)(F)C1=CC(OCC(F)(F)C)=CC=C1C(=O)N1C2=CC=C(F)C=C2C(=C/C(=O)NCCO)/C(F)(F)CC1 JMCFRZPWDILQBV-PDGQHHTCSA-N 0.000 claims description 2
- NIEQTZFARNZVGF-JPVKTXQWSA-N (2z)-2-[4,4-difluoro-1-[4-[(2r)-2-fluoropropoxy]-2-(trifluoromethyl)benzoyl]-2,3-dihydro-1-benzazepin-5-ylidene]-n-(2-hydroxyethyl)acetamide Chemical compound FC(F)(F)C1=CC(OC[C@H](F)C)=CC=C1C(=O)N1C2=CC=CC=C2C(=C/C(=O)NCCO)/C(F)(F)CC1 NIEQTZFARNZVGF-JPVKTXQWSA-N 0.000 claims description 2
- FYBNGXISSSDXFG-SMEDBKPVSA-N (2z)-2-[4,4-difluoro-1-[4-propoxy-2-(trifluoromethyl)benzoyl]-2,3-dihydro-1-benzazepin-5-ylidene]-n-[(2s)-2,3-dihydroxypropyl]acetamide Chemical compound FC(F)(F)C1=CC(OCCC)=CC=C1C(=O)N1C2=CC=CC=C2C(=C/C(=O)NC[C@H](O)CO)/C(F)(F)CC1 FYBNGXISSSDXFG-SMEDBKPVSA-N 0.000 claims description 2
- YNOKDAFPXAGMBS-TWPYZAKFSA-N (2z)-n-[(2r)-2,3-dihydroxypropyl]-2-[4,4,7-trifluoro-1-[4-[(2r)-2-fluoropropoxy]-2-(trifluoromethyl)benzoyl]-2,3-dihydro-1-benzazepin-5-ylidene]acetamide Chemical compound FC(F)(F)C1=CC(OC[C@H](F)C)=CC=C1C(=O)N1C2=CC=C(F)C=C2C(=C/C(=O)NC[C@@H](O)CO)/C(F)(F)CC1 YNOKDAFPXAGMBS-TWPYZAKFSA-N 0.000 claims description 2
- YNOKDAFPXAGMBS-FXAPXLFGSA-N (2z)-n-[(2r)-2,3-dihydroxypropyl]-2-[4,4,7-trifluoro-1-[4-[(2s)-2-fluoropropoxy]-2-(trifluoromethyl)benzoyl]-2,3-dihydro-1-benzazepin-5-ylidene]acetamide Chemical compound FC(F)(F)C1=CC(OC[C@@H](F)C)=CC=C1C(=O)N1C2=CC=C(F)C=C2C(=C/C(=O)NC[C@@H](O)CO)/C(F)(F)CC1 YNOKDAFPXAGMBS-FXAPXLFGSA-N 0.000 claims description 2
- AGLYQHFXGAHYRJ-VQIMKDEXSA-N 2-[[(2z)-2-[4,4,7-trifluoro-1-[4-[(2s)-2-fluoropropoxy]-2-(trifluoromethyl)benzoyl]-2,3-dihydro-1-benzazepin-5-ylidene]acetyl]amino]acetamide Chemical compound FC(F)(F)C1=CC(OC[C@@H](F)C)=CC=C1C(=O)N1C2=CC=C(F)C=C2C(=C/C(=O)NCC(N)=O)/C(F)(F)CC1 AGLYQHFXGAHYRJ-VQIMKDEXSA-N 0.000 claims description 2
- QHPAABHLCSZTGH-FASCHPMRSA-N (2z)-2-[4,4-difluoro-1-[4-[(2r)-2-fluoropropoxy]-2-(trifluoromethyl)benzoyl]-2,3-dihydro-1-benzazepin-5-ylidene]-n-[(2r)-2,3-dihydroxypropyl]acetamide Chemical compound FC(F)(F)C1=CC(OC[C@H](F)C)=CC=C1C(=O)N1C2=CC=CC=C2C(=C/C(=O)NC[C@@H](O)CO)/C(F)(F)CC1 QHPAABHLCSZTGH-FASCHPMRSA-N 0.000 claims 1
- QHPAABHLCSZTGH-ABYGMBSDSA-N (2z)-2-[4,4-difluoro-1-[4-[(2r)-2-fluoropropoxy]-2-(trifluoromethyl)benzoyl]-2,3-dihydro-1-benzazepin-5-ylidene]-n-[(2s)-2,3-dihydroxypropyl]acetamide Chemical compound FC(F)(F)C1=CC(OC[C@H](F)C)=CC=C1C(=O)N1C2=CC=CC=C2C(=C/C(=O)NC[C@H](O)CO)/C(F)(F)CC1 QHPAABHLCSZTGH-ABYGMBSDSA-N 0.000 claims 1
- QHPAABHLCSZTGH-LIEIOVMRSA-N (2z)-2-[4,4-difluoro-1-[4-[(2s)-2-fluoropropoxy]-2-(trifluoromethyl)benzoyl]-2,3-dihydro-1-benzazepin-5-ylidene]-n-[(2s)-2,3-dihydroxypropyl]acetamide Chemical compound FC(F)(F)C1=CC(OC[C@@H](F)C)=CC=C1C(=O)N1C2=CC=CC=C2C(=C/C(=O)NC[C@H](O)CO)/C(F)(F)CC1 QHPAABHLCSZTGH-LIEIOVMRSA-N 0.000 claims 1
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- AZVGAXMUJCVNIU-PDGQHHTCSA-N 3-[[(2z)-2-[1-[4-(2,2-difluoropropoxy)-2-(trifluoromethyl)benzoyl]-4,4,7-trifluoro-2,3-dihydro-1-benzazepin-5-ylidene]acetyl]amino]propanamide Chemical compound FC(F)(F)C1=CC(OCC(F)(F)C)=CC=C1C(=O)N1C2=CC=C(F)C=C2C(=C/C(=O)NCCC(N)=O)/C(F)(F)CC1 AZVGAXMUJCVNIU-PDGQHHTCSA-N 0.000 claims 1
- JIYIAXGCGNHSKR-VCRXTVNUSA-N 3-[[(2z)-2-[4,4,7-trifluoro-1-[4-[(2r)-2-fluoropropoxy]-2-(trifluoromethyl)benzoyl]-2,3-dihydro-1-benzazepin-5-ylidene]acetyl]amino]propanamide Chemical compound FC(F)(F)C1=CC(OC[C@H](F)C)=CC=C1C(=O)N1C2=CC=C(F)C=C2C(=C/C(=O)NCCC(N)=O)/C(F)(F)CC1 JIYIAXGCGNHSKR-VCRXTVNUSA-N 0.000 claims 1
- JIYIAXGCGNHSKR-YQNUULROSA-N 3-[[(2z)-2-[4,4,7-trifluoro-1-[4-[(2s)-2-fluoropropoxy]-2-(trifluoromethyl)benzoyl]-2,3-dihydro-1-benzazepin-5-ylidene]acetyl]amino]propanamide Chemical compound FC(F)(F)C1=CC(OC[C@@H](F)C)=CC=C1C(=O)N1C2=CC=C(F)C=C2C(=C/C(=O)NCCC(N)=O)/C(F)(F)CC1 JIYIAXGCGNHSKR-YQNUULROSA-N 0.000 claims 1
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- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
- 229960004844 lovastatin Drugs 0.000 description 1
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- VJEZQFBMNPYTFJ-CYVLTUHYSA-N methyl (2Z)-2-[1-[4-butoxy-2-(trifluoromethyl)benzoyl]-4,4-difluoro-2,3-dihydro-1-benzazepin-5-ylidene]acetate Chemical compound FC(F)(F)C1=CC(OCCCC)=CC=C1C(=O)N1C2=CC=CC=C2C(=C/C(=O)OC)/C(F)(F)CC1 VJEZQFBMNPYTFJ-CYVLTUHYSA-N 0.000 description 1
- HNTTUOZVNTUYCD-NTMALXAHSA-N methyl (2z)-2-(4,4-difluoro-2,3-dihydro-1h-1-benzazepin-5-ylidene)acetate Chemical compound N1CCC(F)(F)C(=C/C(=O)OC)\C2=CC=CC=C21 HNTTUOZVNTUYCD-NTMALXAHSA-N 0.000 description 1
- ANTJAYJTRVRLKQ-UHFFFAOYSA-N methyl 4-(2,2-difluoropropoxy)-2-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(OCC(C)(F)F)C=C1C(F)(F)F ANTJAYJTRVRLKQ-UHFFFAOYSA-N 0.000 description 1
- KEQAIZDSEAQKCL-UHFFFAOYSA-N methyl 4-(2-oxopropoxy)-2-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(OCC(C)=O)C=C1C(F)(F)F KEQAIZDSEAQKCL-UHFFFAOYSA-N 0.000 description 1
- RKWMPCKVLWSYBZ-MRVPVSSYSA-N methyl 4-[(2r)-2-acetyloxypropoxy]-2-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(OC[C@@H](C)OC(C)=O)C=C1C(F)(F)F RKWMPCKVLWSYBZ-MRVPVSSYSA-N 0.000 description 1
- SYACAOYHJOOMSP-SSDOTTSWSA-N methyl 4-[(2r)-2-fluoropropoxy]-2-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(OC[C@@H](C)F)C=C1C(F)(F)F SYACAOYHJOOMSP-SSDOTTSWSA-N 0.000 description 1
- LXGADNRGIAYYDZ-SSDOTTSWSA-N methyl 4-[(2r)-2-hydroxypropoxy]-2-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(OC[C@@H](C)O)C=C1C(F)(F)F LXGADNRGIAYYDZ-SSDOTTSWSA-N 0.000 description 1
- SYACAOYHJOOMSP-ZETCQYMHSA-N methyl 4-[(2s)-2-fluoropropoxy]-2-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(OC[C@H](C)F)C=C1C(F)(F)F SYACAOYHJOOMSP-ZETCQYMHSA-N 0.000 description 1
- LXGADNRGIAYYDZ-ZETCQYMHSA-N methyl 4-[(2s)-2-hydroxypropoxy]-2-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(OC[C@H](C)O)C=C1C(F)(F)F LXGADNRGIAYYDZ-ZETCQYMHSA-N 0.000 description 1
- GNSLLTXJQSPNOD-UHFFFAOYSA-N methyl 4-[methyl(propyl)amino]-2-(trifluoromethyl)benzoate Chemical compound CCCN(C)C1=CC=C(C(=O)OC)C(C(F)(F)F)=C1 GNSLLTXJQSPNOD-UHFFFAOYSA-N 0.000 description 1
- OLSWKTCQCZAEOW-UHFFFAOYSA-N methyl 4-hydroxy-2-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(O)C=C1C(F)(F)F OLSWKTCQCZAEOW-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
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- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 230000027939 micturition Effects 0.000 description 1
- DDLIGBOFAVUZHB-UHFFFAOYSA-N midazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NC=C2CN=C1C1=CC=CC=C1F DDLIGBOFAVUZHB-UHFFFAOYSA-N 0.000 description 1
- 229960003793 midazolam Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229960001783 nicardipine Drugs 0.000 description 1
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
- 229960001597 nifedipine Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 208000005346 nocturnal enuresis Diseases 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
- 229960002855 simvastatin Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
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- 239000008223 sterile water Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- RVNORSADYXUMRK-RGEXLXHISA-N tert-butyl 2-[4-[(5Z)-4,4-difluoro-5-(2-methoxy-2-oxoethylidene)-2,3-dihydro-1-benzazepine-1-carbonyl]-3-(trifluoromethyl)phenoxy]acetate Chemical compound C1CC(F)(F)C(=C/C(=O)OC)\C2=CC=CC=C2N1C(=O)C1=CC=C(OCC(=O)OC(C)(C)C)C=C1C(F)(F)F RVNORSADYXUMRK-RGEXLXHISA-N 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 108010047303 von Willebrand Factor Proteins 0.000 description 1
- 208000012137 von Willebrand disease (hereditary or acquired) Diseases 0.000 description 1
- 102100036537 von Willebrand factor Human genes 0.000 description 1
- 229960001134 von willebrand factor Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003123032 | 2003-04-28 | ||
| JP2003401126 | 2003-12-01 | ||
| PCT/JP2004/005998 WO2004096775A1 (ja) | 2003-04-28 | 2004-04-26 | ４，４－ジフルオロ－１，２，３，４－テトラヒドロ－５ｈ－１－ベンゾアゼピン誘導体又はその塩 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20055602D0 NO20055602D0 (no) | 2005-11-25 |
| NO20055602L NO20055602L (no) | 2006-01-24 |
| NO333505B1 true NO333505B1 (no) | 2013-06-24 |
Family
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|---|---|---|---|
| NO20055602A NO333505B1 (no) | 2003-04-28 | 2005-11-25 | 4,4-difluor-1,2,3,4-tetrahydro-5H-1-benzazepinderivat eller salt derav, og anvendelse derav for fremstilling av et medikament |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US7183271B2 (pl) |
| EP (1) | EP1619185B1 (pl) |
| KR (1) | KR100882154B1 (pl) |
| AT (1) | ATE512951T1 (pl) |
| AU (1) | AU2004234258B2 (pl) |
| BR (1) | BRPI0409718A (pl) |
| CA (1) | CA2521492C (pl) |
| DK (1) | DK1619185T3 (pl) |
| IL (1) | IL171332A (pl) |
| MX (1) | MXPA05011521A (pl) |
| NO (1) | NO333505B1 (pl) |
| NZ (1) | NZ542815A (pl) |
| PL (1) | PL1619185T3 (pl) |
| PT (1) | PT1619185E (pl) |
| RU (1) | RU2326868C2 (pl) |
| SI (1) | SI1619185T1 (pl) |
| WO (1) | WO2004096775A1 (pl) |
Families Citing this family (9)
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| GB0210397D0 (en) | 2002-05-07 | 2002-06-12 | Ferring Bv | Pharmaceutical formulations |
| BRPI0409718A (pt) | 2003-04-28 | 2006-05-02 | Astellas Pharma Inc | derivado de 4,4-difluoro-1,2,3,4-tetraidro-5h-1-benzazepina ou seu sal |
| US7910751B2 (en) | 2005-07-22 | 2011-03-22 | Mochida Pharmaceutical Co., Ltd. | Heterocyclidene acetamide derivative |
| KR101522747B1 (ko) | 2007-08-06 | 2015-05-26 | 알레간 인코포레이티드 | 데스모프레신 약물 전달을 위한 방법 및 장치 |
| US20100286045A1 (en) | 2008-05-21 | 2010-11-11 | Bjarke Mirner Klein | Methods comprising desmopressin |
| LT2712622T (lt) * | 2008-05-21 | 2016-09-26 | Ferring B.V. | Burnoje disperguojamas desmopresinas, skirtas nikturijos netrikdomo miego pirminio periodo pailginimui |
| US11963995B2 (en) | 2008-05-21 | 2024-04-23 | Ferring B.V. | Methods comprising desmopressin |
| HUE035391T2 (en) | 2012-06-11 | 2018-05-02 | Tacurion | Process for the preparation of 4,4,7-trifluoro-1,2,3,4-tetrahydro-5H-1-benzazepine compound and intermediate of synthesis |
| EP3484876A1 (en) | 2016-07-14 | 2019-05-22 | Pfizer Inc | Novel pyrimidine carboxamides as inhibitors of vanin-1 enzyme |
Family Cites Families (16)
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| RU2137760C1 (ru) | 1993-08-26 | 1999-09-20 | Яманоути Фармасьютикал Ко., Лтд. | Производное бензазепина, фармацевтическая композиция, производное дифторбензазепина и производное (замещенного) аминобензоилдифторбензазепина |
| JPH11349570A (ja) | 1994-06-15 | 1999-12-21 | Otsuka Pharmaceut Co Ltd | ベンゾヘテロ環誘導体 |
| JP3215910B2 (ja) * | 1994-06-15 | 2001-10-09 | 大塚製薬株式会社 | ベンゾヘテロ環誘導体 |
| CN100384825C (zh) | 1994-06-15 | 2008-04-30 | 大塚制药株式会社 | 苯并杂环衍生物 |
| JPH09221476A (ja) * | 1995-12-15 | 1997-08-26 | Otsuka Pharmaceut Co Ltd | 医薬組成物 |
| TW359669B (en) | 1995-12-15 | 1999-06-01 | Otsuka Pharma Co Ltd | Benzazepine derivatives |
| JPH09221475A (ja) | 1996-02-13 | 1997-08-26 | Yamanouchi Pharmaceut Co Ltd | 新規なオキシム誘導体 |
| AR011913A1 (es) | 1997-03-06 | 2000-09-13 | Yamano Masaki | Derivados de 4,4-difluoro-2,3,4,5-tetrahidro-1h-1-benzoazepina y composiciones farmaceuticas de los mismos. |
| JP2926335B2 (ja) | 1997-06-13 | 1999-07-28 | 大塚製薬株式会社 | 医薬組成物 |
| NZ502448A (en) | 1997-07-30 | 2002-12-20 | Wyeth Corp | Tricyclic vasopressin agonists and medicaments containing these compounds |
| IL133788A0 (en) | 1997-07-30 | 2001-04-30 | American Home Prod | Tricyclic vasopressin agonists |
| US6547395B1 (en) | 1998-02-06 | 2003-04-15 | Wavefront Sciences, Inc. | Methods of measuring moving objects and reducing exposure during wavefront measurements |
| DE60001054T2 (de) | 1999-02-04 | 2003-07-24 | Wyeth, Madison | Trizyclische pyridin n-oxide vasopressin agonisten |
| GB0000079D0 (en) | 2000-01-05 | 2000-02-23 | Ferring Bv | Novel antidiuretic agents |
| MXPA04004501A (es) | 2001-11-16 | 2004-08-11 | Yamanouchi Pharma Co Ltd | Derivados de 4-4-difluoro-1,2,3,4-tetrahidro-5h-1-benzazepina o sales de los mismos. |
| BRPI0409718A (pt) | 2003-04-28 | 2006-05-02 | Astellas Pharma Inc | derivado de 4,4-difluoro-1,2,3,4-tetraidro-5h-1-benzazepina ou seu sal |
-
2004
- 2004-04-26 BR BRPI0409718-1A patent/BRPI0409718A/pt not_active IP Right Cessation
- 2004-04-26 KR KR1020057020359A patent/KR100882154B1/ko active IP Right Grant
- 2004-04-26 WO PCT/JP2004/005998 patent/WO2004096775A1/ja not_active Application Discontinuation
- 2004-04-26 MX MXPA05011521A patent/MXPA05011521A/es active IP Right Grant
- 2004-04-26 US US10/554,150 patent/US7183271B2/en not_active Expired - Lifetime
- 2004-04-26 PT PT04729502T patent/PT1619185E/pt unknown
- 2004-04-26 AU AU2004234258A patent/AU2004234258B2/en not_active Ceased
- 2004-04-26 NZ NZ542815A patent/NZ542815A/en not_active IP Right Cessation
- 2004-04-26 CA CA2521492A patent/CA2521492C/en not_active Expired - Fee Related
- 2004-04-26 PL PL04729502T patent/PL1619185T3/pl unknown
- 2004-04-26 AT AT04729502T patent/ATE512951T1/de active
- 2004-04-26 DK DK04729502.7T patent/DK1619185T3/da active
- 2004-04-26 RU RU2005136863/04A patent/RU2326868C2/ru not_active IP Right Cessation
- 2004-04-26 EP EP04729502A patent/EP1619185B1/en not_active Expired - Lifetime
- 2004-04-26 SI SI200431724T patent/SI1619185T1/sl unknown
-
2005
- 2005-10-10 IL IL171332A patent/IL171332A/en active IP Right Grant
- 2005-11-25 NO NO20055602A patent/NO333505B1/no not_active IP Right Cessation
-
2006
- 2006-11-14 US US11/598,732 patent/US7807664B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| SI1619185T1 (sl) | 2011-09-30 |
| IL171332A (en) | 2011-03-31 |
| KR20060007402A (ko) | 2006-01-24 |
| RU2005136863A (ru) | 2006-04-20 |
| PL1619185T3 (pl) | 2011-12-30 |
| RU2326868C2 (ru) | 2008-06-20 |
| CA2521492A1 (en) | 2004-11-11 |
| AU2004234258B2 (en) | 2009-04-09 |
| NO20055602L (no) | 2006-01-24 |
| US7807664B2 (en) | 2010-10-05 |
| NO20055602D0 (no) | 2005-11-25 |
| EP1619185B1 (en) | 2011-06-15 |
| PT1619185E (pt) | 2011-08-25 |
| US20060122170A1 (en) | 2006-06-08 |
| NZ542815A (en) | 2009-01-31 |
| MXPA05011521A (es) | 2006-01-23 |
| DK1619185T3 (da) | 2011-07-18 |
| EP1619185A1 (en) | 2006-01-25 |
| BRPI0409718A (pt) | 2006-05-02 |
| EP1619185A4 (en) | 2008-07-23 |
| US7183271B2 (en) | 2007-02-27 |
| AU2004234258A1 (en) | 2004-11-11 |
| ATE512951T1 (de) | 2011-07-15 |
| CA2521492C (en) | 2010-09-21 |
| KR100882154B1 (ko) | 2009-02-06 |
| WO2004096775A1 (ja) | 2004-11-11 |
| US20070167429A1 (en) | 2007-07-19 |
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