NO326158B1 - Nye benzazepiner og beslektede heterocykliske derivater, farmasoytiske preparater inneholdende slike og fremgangsmate for fremstilling av slike samt slike forbindelser for anvendelse som medikament - Google Patents
Nye benzazepiner og beslektede heterocykliske derivater, farmasoytiske preparater inneholdende slike og fremgangsmate for fremstilling av slike samt slike forbindelser for anvendelse som medikament Download PDFInfo
- Publication number
- NO326158B1 NO326158B1 NO20032905A NO20032905A NO326158B1 NO 326158 B1 NO326158 B1 NO 326158B1 NO 20032905 A NO20032905 A NO 20032905A NO 20032905 A NO20032905 A NO 20032905A NO 326158 B1 NO326158 B1 NO 326158B1
- Authority
- NO
- Norway
- Prior art keywords
- dimethoxy
- benzyl
- benzo
- tetrahydro
- azepin
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 60
- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 22
- 239000003814 drug Substances 0.000 title claims description 6
- 150000008038 benzoazepines Chemical class 0.000 title abstract description 12
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 3
- 239000004480 active ingredient Substances 0.000 claims abstract 3
- 125000004321 azepin-2-yl group Chemical group [H]N1C([H])=C([H])C([H])=C([H])C([H])=C1* 0.000 claims description 150
- 239000000203 mixture Substances 0.000 claims description 61
- -1 for example Chemical class 0.000 claims description 48
- ZRJOKIUEJIOAPR-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-2-phenylacetic acid Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCCN1C(C(O)=O)C1=CC=CC=C1 ZRJOKIUEJIOAPR-UHFFFAOYSA-N 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 102000002512 Orexin Human genes 0.000 claims description 16
- 108060005714 orexin Proteins 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 13
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
- 208000008589 Obesity Diseases 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 7
- 125000005605 benzo group Chemical group 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
- 125000001041 indolyl group Chemical group 0.000 claims description 7
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 235000020824 obesity Nutrition 0.000 claims description 7
- 229940080818 propionamide Drugs 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000005493 quinolyl group Chemical group 0.000 claims description 7
- 208000019116 sleep disease Diseases 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- LSBDFXRDZJMBSC-UHFFFAOYSA-N Amide-Phenylacetic acid Natural products NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 5
- ZDGREJASPPCBKV-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-2-phenyl-n-(pyrazin-2-ylmethyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCCN1C(C=1C=CC=CC=1)C(=O)NCC1=CN=CC=N1 ZDGREJASPPCBKV-UHFFFAOYSA-N 0.000 claims description 5
- OODOKBUERXZTEM-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-n-(3-ethoxypropyl)-2-phenylacetamide Chemical compound C=1C=CC=CC=1C(C(=O)NCCCOCC)N1CCCC2=CC(OC)=C(OC)C=C2C1CC1=CC=C(OC)C(OC)=C1 OODOKBUERXZTEM-UHFFFAOYSA-N 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- RXOMTHSWBRHWFB-UHFFFAOYSA-N ethyl 2-[[2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-2-phenylacetyl]amino]acetate Chemical compound C=1C=CC=CC=1C(C(=O)NCC(=O)OCC)N1CCCC2=CC(OC)=C(OC)C=C2C1CC1=CC=C(OC)C(OC)=C1 RXOMTHSWBRHWFB-UHFFFAOYSA-N 0.000 claims description 5
- KUSBLETVJOWRFU-UHFFFAOYSA-N methyl 3-[[2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-2-phenylacetyl]amino]propanoate Chemical compound C=1C=CC=CC=1C(C(=O)NCCC(=O)OC)N1CCCC2=CC(OC)=C(OC)C=C2C1CC1=CC=C(OC)C(OC)=C1 KUSBLETVJOWRFU-UHFFFAOYSA-N 0.000 claims description 5
- UHKAJLSKXBADFT-UHFFFAOYSA-N 1,3-indandione Chemical compound C1=CC=C2C(=O)CC(=O)C2=C1 UHKAJLSKXBADFT-UHFFFAOYSA-N 0.000 claims description 4
- UDQSXTNTGLMCLG-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-2-phenyl-n-(pyridin-3-ylmethyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCCN1C(C=1C=CC=CC=1)C(=O)NCC1=CC=CN=C1 UDQSXTNTGLMCLG-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- HKQKTAMBBMTGDD-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-1-yl)-2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCCN1CC(=O)NC1C2=CC=CC=C2CC1 HKQKTAMBBMTGDD-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- MPFLOPTYHIWHPE-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-2-phenyl-n-(quinolin-2-ylmethyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCCN1C(C=1C=CC=CC=1)C(=O)NCC1=CC=C(C=CC=C2)C2=N1 MPFLOPTYHIWHPE-UHFFFAOYSA-N 0.000 claims description 3
- UKXTXTNECPGUOU-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-2-phenylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCCN1C(C(N)=O)C1=CC=CC=C1 UKXTXTNECPGUOU-UHFFFAOYSA-N 0.000 claims description 3
- GLKGMBLBUXTRNS-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-n-(furan-2-ylmethyl)-2-phenylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCCN1C(C=1C=CC=CC=1)C(=O)NCC1=CC=CO1 GLKGMBLBUXTRNS-UHFFFAOYSA-N 0.000 claims description 3
- UFYDEPGYHVIHIO-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-n-[(1-methylindazol-3-yl)methyl]-2-phenylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCCN1C(C=1C=CC=CC=1)C(=O)NCC1=NN(C)C2=CC=CC=C12 UFYDEPGYHVIHIO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
- POSPYQBWALZTKG-UHFFFAOYSA-N methyl 2-[[2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-2-phenylacetyl]amino]-3-hydroxypropanoate Chemical compound C=1C=CC=CC=1C(C(=O)NC(CO)C(=O)OC)N1CCCC2=CC(OC)=C(OC)C=C2C1CC1=CC=C(OC)C(OC)=C1 POSPYQBWALZTKG-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- QUWWIIRDEGPVPH-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-1-yl)-2-[1-[(3,4-dimethoxyphenyl)methyl]-7-methoxy-8-propan-2-yloxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC(C)C)=C(OC)C=C2CCCN1CC(=O)NC1C2=CC=CC=C2CC1 QUWWIIRDEGPVPH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 2
- UXSNPWRWHWVTBA-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-n-(3-hydroxypropyl)-2-phenylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCCN1C(C(=O)NCCCO)C1=CC=CC=C1 UXSNPWRWHWVTBA-UHFFFAOYSA-N 0.000 claims description 2
- RJJZERINOZZCMV-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-n-(3-phenyl-2,3-dihydro-1h-inden-1-yl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCCN1CC(=O)NC1C2=CC=CC=C2C(C=2C=CC=CC=2)C1 RJJZERINOZZCMV-UHFFFAOYSA-N 0.000 claims description 2
- BETUUILLOVSEAL-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-n-(naphthalen-1-ylmethyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCCN1CC(=O)NCC1=CC=CC2=CC=CC=C12 BETUUILLOVSEAL-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- LKLCKJXNZVHPQW-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-2-yl)-2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCCN1CC(=O)NC1CC2=CC=CC=C2C1 LKLCKJXNZVHPQW-UHFFFAOYSA-N 0.000 claims description 2
- QKODOALLIMEFAQ-UHFFFAOYSA-N n-(cyanomethyl)-2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-2-phenylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCCN1C(C(=O)NCC#N)C1=CC=CC=C1 QKODOALLIMEFAQ-UHFFFAOYSA-N 0.000 claims description 2
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 claims 3
- NQKCJVGYQMQDNT-UHFFFAOYSA-N n-cyclopentyl-2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-2-phenylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCCN1C(C=1C=CC=CC=1)C(=O)NC1CCCC1 NQKCJVGYQMQDNT-UHFFFAOYSA-N 0.000 claims 2
- BNUAZZNLMVATQP-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-2-phenyl-n-prop-2-ynylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCCN1C(C(=O)NCC#C)C1=CC=CC=C1 BNUAZZNLMVATQP-UHFFFAOYSA-N 0.000 claims 1
- ZSRYAVUNNADOFU-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-n-[(1-methylbenzimidazol-2-yl)methyl]-2-phenylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCCN1C(C=1C=CC=CC=1)C(=O)NCC1=NC2=CC=CC=C2N1C ZSRYAVUNNADOFU-UHFFFAOYSA-N 0.000 claims 1
- 239000012876 carrier material Substances 0.000 claims 1
- MBTRBDRYULFSCA-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-2-phenylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCCN1C(C=1C=CC=CC=1)C(=O)NCC1=CC=C(OCO2)C2=C1 MBTRBDRYULFSCA-UHFFFAOYSA-N 0.000 claims 1
- MEFSKYLTPHEZTC-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-2-[8-(2,2-difluoroethoxy)-1-[(3,4-dimethoxyphenyl)methyl]-7-methoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-2-phenylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OCC(F)F)=C(OC)C=C2CCCN1C(C=1C=CC=CC=1)C(=O)NCC1=CC=C(OCO2)C2=C1 MEFSKYLTPHEZTC-UHFFFAOYSA-N 0.000 claims 1
- CIKPTGFKVJUBIX-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-1-yl)-2-[1-[(3,4-dimethoxyphenyl)methyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]-2-phenylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCCN1C(C=1C=CC=CC=1)C(=O)NC1C2=CC=CC=C2CC1 CIKPTGFKVJUBIX-UHFFFAOYSA-N 0.000 claims 1
- BTDLTVCMYAYRDQ-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-1-yl)-2-[1-[(3,4-dimethoxyphenyl)methyl]-7-methoxy-8-phenylmethoxy-1,3,4,5-tetrahydro-2-benzazepin-2-yl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OCC=3C=CC=CC=3)=C(OC)C=C2CCCN1CC(=O)NC1C2=CC=CC=C2CC1 BTDLTVCMYAYRDQ-UHFFFAOYSA-N 0.000 claims 1
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- 125000003226 pyrazolyl group Chemical group 0.000 description 1
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- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- XPAZBFLKFMBGMF-UHFFFAOYSA-N quinolin-2-ylmethanamine;dihydrochloride Chemical compound Cl.Cl.C1=CC=CC2=NC(CN)=CC=C21 XPAZBFLKFMBGMF-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
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- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 239000011734 sodium Substances 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
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
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- 239000003765 sweetening agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000006068 taste-masking agent Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
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- APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical class NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 0.000 description 1
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Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/14—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D281/10—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D403/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D417/12—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 chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Child & Adolescent Psychology (AREA)
- Anesthesiology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/EP2000/013289 WO2002051232A2 (en) | 2000-12-27 | 2000-12-27 | Novel benzazepines and related heterocyclic derivatives |
PCT/EP2001/015074 WO2002051838A1 (en) | 2000-12-27 | 2001-12-19 | Novel benzazepines and related heterocyclic derivatives which are useful as orexin receptor antagonists |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20032905D0 NO20032905D0 (no) | 2003-06-24 |
NO20032905L NO20032905L (no) | 2003-06-24 |
NO326158B1 true NO326158B1 (no) | 2008-10-13 |
Family
ID=8164232
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20032905A NO326158B1 (no) | 2000-12-27 | 2003-06-24 | Nye benzazepiner og beslektede heterocykliske derivater, farmasoytiske preparater inneholdende slike og fremgangsmate for fremstilling av slike samt slike forbindelser for anvendelse som medikament |
Country Status (18)
Country | Link |
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US (1) | US7192950B2 (ko) |
EP (1) | EP1347967B1 (ko) |
JP (1) | JP4219166B2 (ko) |
KR (1) | KR100849569B1 (ko) |
CN (1) | CN1261430C (ko) |
AT (1) | ATE381560T1 (ko) |
AU (1) | AU2002240855B2 (ko) |
BR (1) | BR0116505A (ko) |
CA (1) | CA2431982C (ko) |
DE (1) | DE60132017T2 (ko) |
ES (1) | ES2296825T3 (ko) |
HU (1) | HUP0301665A3 (ko) |
IL (2) | IL155806A0 (ko) |
MX (1) | MXPA03004779A (ko) |
NO (1) | NO326158B1 (ko) |
NZ (1) | NZ525613A (ko) |
WO (2) | WO2002051232A2 (ko) |
ZA (1) | ZA200303697B (ko) |
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US3236838A (en) * | 1964-06-09 | 1966-02-22 | Hoffmann La Roche | Certain 1-substituted-benzodiazepin-2-one compounds |
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NO20032905D0 (no) | 2003-06-24 |
AU2002240855B2 (en) | 2006-08-17 |
KR100849569B1 (ko) | 2008-07-31 |
NO20032905L (no) | 2003-06-24 |
CA2431982A1 (en) | 2002-07-04 |
EP1347967A1 (en) | 2003-10-01 |
DE60132017D1 (de) | 2008-01-31 |
CA2431982C (en) | 2010-07-20 |
MXPA03004779A (es) | 2003-09-25 |
NZ525613A (en) | 2005-01-28 |
JP4219166B2 (ja) | 2009-02-04 |
US20040058912A1 (en) | 2004-03-25 |
IL155806A0 (en) | 2003-12-23 |
EP1347967B1 (en) | 2007-12-19 |
ATE381560T1 (de) | 2008-01-15 |
DE60132017T2 (de) | 2008-12-04 |
CN1481380A (zh) | 2004-03-10 |
ZA200303697B (en) | 2004-08-13 |
WO2002051232A2 (en) | 2002-07-04 |
WO2002051838A1 (en) | 2002-07-04 |
HUP0301665A3 (en) | 2008-12-29 |
IL155806A (en) | 2008-03-20 |
HUP0301665A2 (en) | 2008-07-28 |
BR0116505A (pt) | 2004-02-03 |
ES2296825T3 (es) | 2008-05-01 |
JP2004516324A (ja) | 2004-06-03 |
CN1261430C (zh) | 2006-06-28 |
US7192950B2 (en) | 2007-03-20 |
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