LV11327B - Imidazodiazepine - Google Patents

Info

Publication number

LV11327B

LV11327B LVP-95-59A LV950059A LV11327B LV 11327 B LV11327 B LV 11327B LV 950059 A LV950059 A LV 950059A LV 11327 B LV11327 B LV 11327B

Authority

LV

Latvia

Prior art keywords

imidazo

dihydro

mmol

oxadiazol

wurde

Prior art date

1994-03-16

Links

• Espacenet
• Global Dossier
• Discuss

• BMGXAZCDDYTVFV-UHFFFAOYSA-N imidazo[4,5-c]diazepine Chemical compound C1=CN=NC2=NC=NC2=C1 BMGXAZCDDYTVFV-UHFFFAOYSA-N 0.000 title claims description 6
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 95
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
• 150000003839 salts Chemical class 0.000 claims abstract description 6
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract 3
• -1 isoindolin-2-yl Chemical group 0.000 claims description 440
• QIMDWIBCKKVBRU-UHFFFAOYSA-N imidazo[1,5-a][1,4]benzodiazepin-9-one Chemical compound N1=CC2=CN=CN2C2=CC(=O)C=CC2=C1 QIMDWIBCKKVBRU-UHFFFAOYSA-N 0.000 claims description 122
• KSSXNHGPIDAUAS-UHFFFAOYSA-N 1,4-benzodiazepin-6-one Chemical compound N1=CC=NC=C2C(=O)C=CC=C21 KSSXNHGPIDAUAS-UHFFFAOYSA-N 0.000 claims description 69
• IEZFHFAOJFVULZ-UHFFFAOYSA-N 1,4-benzodiazepin-9-one Chemical compound C1=NC=CN=C2C(=O)C=CC=C21 IEZFHFAOJFVULZ-UHFFFAOYSA-N 0.000 claims description 69
• YZPAKBGVJIVPEU-UHFFFAOYSA-N 1,2-benzodiazepin-6-one Chemical compound N1=NC=CC=C2C(=O)C=CC=C21 YZPAKBGVJIVPEU-UHFFFAOYSA-N 0.000 claims description 47
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 28
• 239000002253 acid Substances 0.000 claims description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
• 150000001875 compounds Chemical class 0.000 claims description 20
• 125000003342 alkenyl group Chemical group 0.000 claims description 19
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 17
• 230000002829 reductive effect Effects 0.000 claims description 14
• 239000001257 hydrogen Substances 0.000 claims description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 125000003282 alkyl amino group Chemical group 0.000 claims description 5
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• 239000002249 anxiolytic agent Substances 0.000 claims description 4
• 125000003118 aryl group Chemical group 0.000 claims description 4
• RQWUBEUSGOXDIL-UHFFFAOYSA-N 3-[5-[(dipropylamino)methyl]-1,2,4-oxadiazol-3-yl]-5-methyl-7-(trifluoromethyl)-4h-imidazo[1,5-a][1,4]benzodiazepin-6-one Chemical compound O1C(CN(CCC)CCC)=NC(C2=C3N(C4=C(C(=CC=C4)C(F)(F)F)C(=O)N(C)C3)C=N2)=N1 RQWUBEUSGOXDIL-UHFFFAOYSA-N 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• QKGRESFVCPTLIF-UHFFFAOYSA-N 2,4,10-triazatetracyclo[10.4.0.02,6.07,10]hexadeca-1(16),3,5,7,12,14-hexaen-11-one Chemical compound O=C1N2CC=C2C2=CN=CN2C2=CC=CC=C12 QKGRESFVCPTLIF-UHFFFAOYSA-N 0.000 claims description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
• 229910052731 fluorine Inorganic materials 0.000 claims description 2
• 150000002527 isonitriles Chemical class 0.000 claims description 2
• 238000000034 method Methods 0.000 claims description 2
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 7
• LVWUPEUAJYNZGD-UHFFFAOYSA-N 1,4-benzodiazepin-8-one Chemical compound N1=CC=NC=C2C1=CC(C=C2)=O LVWUPEUAJYNZGD-UHFFFAOYSA-N 0.000 claims 5
• 125000004663 dialkyl amino group Chemical group 0.000 claims 4
• 230000001773 anti-convulsant effect Effects 0.000 claims 3
• 239000001961 anticonvulsive agent Substances 0.000 claims 3
• 229960003965 antiepileptics Drugs 0.000 claims 3
• 230000000949 anxiolytic effect Effects 0.000 claims 3
• 239000003814 drug Substances 0.000 claims 3
• 239000003158 myorelaxant agent Substances 0.000 claims 3
• 125000006239 protecting group Chemical group 0.000 claims 3
• 230000004799 sedative–hypnotic effect Effects 0.000 claims 3
• 125000001153 fluoro group Chemical group F* 0.000 claims 2
• DOKTYBSEOBESKA-INIZCTEOSA-N (s)-8-chloro-1-(5-dipropylaminomethyl-1,3,4-oxadiazol-2-yl)-12,12a-dihydro-9h,11h-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepin-9-one Chemical compound O1C(CN(CCC)CCC)=NN=C1C1=C([C@H]2N(CC2)C(=O)C=2C3=CC=CC=2Cl)N3C=N1 DOKTYBSEOBESKA-INIZCTEOSA-N 0.000 claims 1
• YKWRYJUFCLMQAW-UHFFFAOYSA-N 3-[5-(1,3-dihydroisoindol-2-ylmethyl)-1,2,4-oxadiazol-3-yl]-8-fluoro-5-methyl-4h-imidazo[1,5-a][1,4]benzodiazepin-6-one Chemical compound O=C1N(C)CC2=C(C=3N=C(CN4CC5=CC=CC=C5C4)ON=3)N=CN2C2=CC=C(F)C=C21 YKWRYJUFCLMQAW-UHFFFAOYSA-N 0.000 claims 1
• NOQIYRGMEFBZTI-UHFFFAOYSA-N 3-[5-[(dipropylamino)methyl]-1,2,4-oxadiazol-3-yl]-8-fluoro-5-methyl-4h-imidazo[1,5-a][1,4]benzodiazepin-6-one Chemical compound O1C(CN(CCC)CCC)=NC(C2=C3N(C4=CC=C(F)C=C4C(=O)N(C)C3)C=N2)=N1 NOQIYRGMEFBZTI-UHFFFAOYSA-N 0.000 claims 1
• MFOMCCCPIDRAJY-UHFFFAOYSA-N ClC1=CC=CC2=C1CN(CC=1N2C=NC1C1=NOC(=N1)CN(CC)CC)C Chemical compound ClC1=CC=CC2=C1CN(CC=1N2C=NC1C1=NOC(=N1)CN(CC)CC)C MFOMCCCPIDRAJY-UHFFFAOYSA-N 0.000 claims 1
• 150000007513 acids Chemical class 0.000 claims 1
• 239000004480 active ingredient Substances 0.000 claims 1
• 239000013543 active substance Substances 0.000 claims 1
• 150000001408 amides Chemical class 0.000 claims 1
• 150000001412 amines Chemical class 0.000 claims 1
• 125000003277 amino group Chemical group 0.000 claims 1
• 125000004429 atom Chemical group 0.000 claims 1
• 229910052799 carbon Inorganic materials 0.000 claims 1
• 150000001735 carboxylic acids Chemical class 0.000 claims 1
• 229910052801 chlorine Inorganic materials 0.000 claims 1
• 125000001309 chloro group Chemical group Cl* 0.000 claims 1
• 125000002897 diene group Chemical group 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
• 229940124597 therapeutic agent Drugs 0.000 claims 1
• 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
• 125000005843 halogen group Chemical group 0.000 abstract description 2
• MBDPOXAMXCPREM-UHFFFAOYSA-N 4-imidazo[4,5-c]diazepin-3-yloxadiazole Chemical class N1=NC2=NC=NC2=CC=C1C1=CON=N1 MBDPOXAMXCPREM-UHFFFAOYSA-N 0.000 abstract 1
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 898
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 829
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 753
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 354
• 239000000243 solution Substances 0.000 description 246
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 225
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 179
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 144
• 239000000725 suspension Substances 0.000 description 143
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 142
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 112
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 110
• 239000000499 gel Substances 0.000 description 105
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 100
• 239000013078 crystal Substances 0.000 description 99
• 229940073584 methylene chloride Drugs 0.000 description 97
• ZSUUCLLIOSUIFH-UHFFFAOYSA-N n,n-di(propan-2-yl)acetamide Chemical compound CC(C)N(C(C)C)C(C)=O ZSUUCLLIOSUIFH-UHFFFAOYSA-N 0.000 description 80
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 74
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 72
• 238000006243 chemical reaction Methods 0.000 description 58
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 55
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 47
• 235000019341 magnesium sulphate Nutrition 0.000 description 47
• 239000000706 filtrate Substances 0.000 description 46
• 239000005862 Whey Substances 0.000 description 44
• 102000007544 Whey Proteins Human genes 0.000 description 44
• 108010046377 Whey Proteins Proteins 0.000 description 44
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 43
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 42
• NVBIQLHPGVJBCA-UHFFFAOYSA-N 1H-thieno[3,2-e][1,4]diazepin-8-one Chemical compound N1C=CN=CC2=C1C(CS2)=O NVBIQLHPGVJBCA-UHFFFAOYSA-N 0.000 description 38
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 36
• 229910052786 argon Inorganic materials 0.000 description 36
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
• BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 35
• 239000000203 mixture Substances 0.000 description 35
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 34
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 27
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 25
• 239000011541 reaction mixture Substances 0.000 description 25
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 24
• 229910052757 nitrogen Inorganic materials 0.000 description 24
• 229910052708 sodium Inorganic materials 0.000 description 24
• 239000011734 sodium Substances 0.000 description 24
• JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 23
• 241000283011 Rangifer Species 0.000 description 22
• 229910000029 sodium carbonate Inorganic materials 0.000 description 21
• WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 20
• 235000019441 ethanol Nutrition 0.000 description 20
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• 239000000047 product Substances 0.000 description 18
• VRPJIFMKZZEXLR-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NCC(O)=O VRPJIFMKZZEXLR-UHFFFAOYSA-N 0.000 description 16
• 235000014676 Phragmites communis Nutrition 0.000 description 16
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 16
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• 235000011152 sodium sulphate Nutrition 0.000 description 16
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 150000002148 esters Chemical class 0.000 description 15
• LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 description 14
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• 201000004624 Dermatitis Diseases 0.000 description 14
• SEWLRCANWRSSPY-UHFFFAOYSA-N N'-hydroxy-1,2-benzodiazepine-1-carboximidamide Chemical compound N1(N=CC=CC2=C1C=CC=C2)C(N)=NO SEWLRCANWRSSPY-UHFFFAOYSA-N 0.000 description 14
• 229910000104 sodium hydride Inorganic materials 0.000 description 14
• CFMIOXCGQIHWJP-UHFFFAOYSA-N 1,2-benzodiazepine-1-carboxylic acid Chemical compound OC(=O)N1N=CC=CC2=CC=CC=C12 CFMIOXCGQIHWJP-UHFFFAOYSA-N 0.000 description 13
• 108010010803 Gelatin Proteins 0.000 description 12
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• 238000004587 chromatography analysis Methods 0.000 description 12
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• 235000019322 gelatine Nutrition 0.000 description 12
• 235000011852 gelatine desserts Nutrition 0.000 description 12
• 150000004028 organic sulfates Chemical class 0.000 description 12
• JXYPNRIYAMXJSE-UHFFFAOYSA-N 1,4-diazepin-6-one Chemical compound O=C1C=NC=CN=C1 JXYPNRIYAMXJSE-UHFFFAOYSA-N 0.000 description 11
• 241000209219 Hordeum Species 0.000 description 11
• 235000007340 Hordeum vulgare Nutrition 0.000 description 11
• 150000008064 anhydrides Chemical class 0.000 description 11
• MXBFSAYTTZBUBY-UHFFFAOYSA-N n-chlorohydroxylamine Chemical compound ONCl MXBFSAYTTZBUBY-UHFFFAOYSA-N 0.000 description 11
• AAUUCDYRPRKIOH-UHFFFAOYSA-N 1,4-benzodiazepin-6-one;hydrochloride Chemical compound Cl.N1=CC=NC=C2C(=O)C=CC=C21 AAUUCDYRPRKIOH-UHFFFAOYSA-N 0.000 description 10
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
• JUAZIBRVRMDBOR-UHFFFAOYSA-N N'-hydroxy-1H-imidazo[1,5-a][1,4]benzodiazepine-1-carboximidamide Chemical compound C1(N=CC=2N1C1=C(C=NC2)C=CC=C1)C(N)=NO JUAZIBRVRMDBOR-UHFFFAOYSA-N 0.000 description 10
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
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• 229910052763 palladium Inorganic materials 0.000 description 9
• FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 8
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• 239000002585 base Substances 0.000 description 8
• 238000002425 crystallisation Methods 0.000 description 8
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• 239000002904 solvent Substances 0.000 description 8
• HOLSFJRLBIUPFK-JTQLQIEISA-N (s)-1-(3-aminomethyl-1,2,4-oxadiazol-5-yl)-8-chloro-12,12a-dihydro-9h,11h-azeto[2,1-c]-imidazo[1,5-a][1,4]benzodiazepin-9-one Chemical compound NCC1=NOC(C2=C3N(C4=CC=CC(Cl)=C4C(=O)N4CC[C@H]43)C=N2)=N1 HOLSFJRLBIUPFK-JTQLQIEISA-N 0.000 description 7
• XBBSCQFBTXPTRV-UHFFFAOYSA-N 1,2-benzodiazepin-9-one Chemical compound C1=CC=NN=C2C(=O)C=CC=C21 XBBSCQFBTXPTRV-UHFFFAOYSA-N 0.000 description 7
• VXOWLWOYKRQXOT-UHFFFAOYSA-N 1,4-benzodiazepine-1-carbonitrile Chemical compound N#CN1C=CN=CC2=CC=CC=C12 VXOWLWOYKRQXOT-UHFFFAOYSA-N 0.000 description 7
• CEHKKWWXELBNPS-UHFFFAOYSA-N 1,4-benzodiazepine-1-carboxylic acid Chemical compound OC(=O)N1C=CN=CC2=CC=CC=C12 CEHKKWWXELBNPS-UHFFFAOYSA-N 0.000 description 7
• 239000004677 Nylon Substances 0.000 description 7
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• 239000012312 sodium hydride Substances 0.000 description 7
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 7
• GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 description 7
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