FI110944B - Menetelmä terapeuttisesti käyttökelpoisten pyrrolo-, pyratsolo- ja imidatso[2,1-c][1,4]diatsepiinien valmistamiseksi - Google Patents

Info

Publication number

FI110944B

FI110944B FI943543A FI943543A FI110944B FI 110944 B FI110944 B FI 110944B FI 943543 A FI943543 A FI 943543A FI 943543 A FI943543 A FI 943543A FI 110944 B FI110944 B FI 110944B

Authority

FI

Finland

Prior art keywords

pyrrolo

benzodiazepine

ylcarbonyl

phenyl

give

Prior art date

1993-07-29

Links

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• 238000000034 method Methods 0.000 title claims description 20
• 238000002360 preparation method Methods 0.000 title claims description 14
• 230000008569 process Effects 0.000 title claims description 8
• JGEMFVRZSFKXSR-UHFFFAOYSA-N N1=CCN2C1=CN=CC=C2 Chemical class N1=CCN2C1=CN=CC=C2 JGEMFVRZSFKXSR-UHFFFAOYSA-N 0.000 title claims description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 208
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 71
• 150000003839 salts Chemical class 0.000 claims abstract description 14
• 125000003118 aryl group Chemical group 0.000 claims abstract description 6
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
• 229910052760 oxygen Inorganic materials 0.000 claims abstract 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 578
• -1 5H-pyrrolo [2,1-c] [1,4] benzodiazepine-10 (11H) -ylcarbonyl Chemical group 0.000 claims description 222
• 150000001875 compounds Chemical class 0.000 claims description 82
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 75
• 150000002367 halogens Chemical class 0.000 claims description 33
• 229910052739 hydrogen Inorganic materials 0.000 claims description 32
• 229910052736 halogen Inorganic materials 0.000 claims description 31
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
• 239000000460 chlorine Substances 0.000 claims description 29
• 239000001257 hydrogen Substances 0.000 claims description 28
• 229910052786 argon Inorganic materials 0.000 claims description 26
• 239000002253 acid Substances 0.000 claims description 17
• 238000006243 chemical reaction Methods 0.000 claims description 15
• 150000002431 hydrogen Chemical class 0.000 claims description 15
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 125000001424 substituent group Chemical group 0.000 claims description 8
• 239000003086 colorant Substances 0.000 claims description 7
• 150000001412 amines Chemical class 0.000 claims description 5
• 150000008064 anhydrides Chemical class 0.000 claims description 5
• 239000003153 chemical reaction reagent Substances 0.000 claims description 5
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 5
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 5
• 239000002002 slurry Substances 0.000 claims description 5
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 3
• 125000003435 aroyl group Chemical group 0.000 claims description 2
• 239000000571 coke Substances 0.000 claims description 2
• 125000002541 furyl group Chemical group 0.000 claims description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
• 239000012026 peptide coupling reagents‎ Substances 0.000 claims description 2
• 230000001225 therapeutic effect Effects 0.000 claims description 2
• 125000001544 thienyl group Chemical group 0.000 claims description 2
• 229910052721 tungsten Inorganic materials 0.000 claims description 2
• 241000277284 Salvelinus fontinalis Species 0.000 claims 1
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
• PPHTXRNHTVLQED-UHFFFAOYSA-N lixivaptan Chemical compound CC1=CC=C(F)C=C1C(=O)NC(C=C1Cl)=CC=C1C(=O)N1C2=CC=CC=C2CN2C=CC=C2C1 PPHTXRNHTVLQED-UHFFFAOYSA-N 0.000 claims 1
• 230000001338 necrotic effect Effects 0.000 claims 1
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 46
• 229910052757 nitrogen Inorganic materials 0.000 abstract description 8
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract description 6
• LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 abstract description 3
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• 229910052799 carbon Inorganic materials 0.000 abstract description 2
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 2
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• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 1
• 229940002612 prodrug Drugs 0.000 abstract 1
• 239000000651 prodrug Substances 0.000 abstract 1
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• 239000007787 solid Substances 0.000 description 281
• 239000000203 mixture Substances 0.000 description 258
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• 239000000243 solution Substances 0.000 description 170
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• 239000000047 product Substances 0.000 description 134
• 239000011541 reaction mixture Substances 0.000 description 128
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 123
• 235000019439 ethyl acetate Nutrition 0.000 description 118
• 239000011734 sodium Substances 0.000 description 113
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• 239000000706 filtrate Substances 0.000 description 96
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• 239000012267 brine Substances 0.000 description 84
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 84
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 75
• 238000003756 stirring Methods 0.000 description 74
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 67
• HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 56
• 239000000391 magnesium silicate Substances 0.000 description 56
• 229910052919 magnesium silicate Inorganic materials 0.000 description 56
• 235000019792 magnesium silicate Nutrition 0.000 description 56
• 239000003039 volatile agent Substances 0.000 description 51
• 239000012044 organic layer Substances 0.000 description 50
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• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 48
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
• 239000013078 crystal Substances 0.000 description 45
• 239000000741 silica gel Substances 0.000 description 43
• 229910002027 silica gel Inorganic materials 0.000 description 43
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
• 238000003818 flash chromatography Methods 0.000 description 42
• 235000019441 ethanol Nutrition 0.000 description 38
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 36
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 34
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• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
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