CA1177069A - Phenyl ketones - Google Patents
Phenyl ketonesInfo
- Publication number
- CA1177069A CA1177069A CA000233720A CA233720A CA1177069A CA 1177069 A CA1177069 A CA 1177069A CA 000233720 A CA000233720 A CA 000233720A CA 233720 A CA233720 A CA 233720A CA 1177069 A CA1177069 A CA 1177069A
- Authority
- CA
- Canada
- Prior art keywords
- group
- glycinamide
- methyl
- obvious chemical
- starting material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000008366 benzophenones Chemical class 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 48
- 239000002253 acid Chemical group 0.000 claims abstract description 42
- -1 substituted-phenyl ketones Chemical class 0.000 claims abstract description 40
- 125000002252 acyl group Chemical group 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 19
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 17
- 150000001413 amino acids Chemical class 0.000 claims abstract description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
- 125000005059 halophenyl group Chemical group 0.000 claims abstract description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 107
- 150000001875 compounds Chemical class 0.000 claims description 82
- 239000007858 starting material Substances 0.000 claims description 44
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims description 27
- 239000012965 benzophenone Substances 0.000 claims description 22
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 125000006239 protecting group Chemical group 0.000 claims description 18
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
- 229940024606 amino acid Drugs 0.000 claims description 15
- 235000001014 amino acid Nutrition 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 13
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 125000003412 L-alanyl group Chemical group [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 235000017168 chlorine Nutrition 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000012458 free base Substances 0.000 claims description 9
- 125000003440 L-leucyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C(C([H])([H])[H])([H])C([H])([H])[H] 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Chemical group 0.000 claims description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 6
- 230000000802 nitrating effect Effects 0.000 claims description 6
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 5
- 125000002435 L-phenylalanyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 239000004472 Lysine Substances 0.000 claims description 5
- 229960005190 phenylalanine Drugs 0.000 claims description 5
- 150000008575 L-amino acids Chemical class 0.000 claims description 4
- 125000003580 L-valyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(C([H])([H])[H])(C([H])([H])[H])[H] 0.000 claims description 4
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 4
- 125000001998 leucyl group Chemical group 0.000 claims description 4
- 229910052705 radium Inorganic materials 0.000 claims description 4
- 229910052701 rubidium Inorganic materials 0.000 claims description 4
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- DWVJBXQITWMYAJ-SFHVURJKSA-N (2s)-2-amino-n-[2-[4-bromo-2-(pyridine-2-carbonyl)anilino]-2-oxoethyl]-3-phenylpropanamide Chemical compound C([C@H](N)C(=O)NCC(=O)NC=1C(=CC(Br)=CC=1)C(=O)C=1N=CC=CC=1)C1=CC=CC=C1 DWVJBXQITWMYAJ-SFHVURJKSA-N 0.000 claims description 3
- FYUPTROPMDKDPF-UHFFFAOYSA-N 2-amino-n-[2-(2-benzoyl-4-nitroanilino)-2-oxoethyl]acetamide Chemical compound NCC(=O)NCC(=O)NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 FYUPTROPMDKDPF-UHFFFAOYSA-N 0.000 claims description 3
- NCVBBNHPRGOHFA-UHFFFAOYSA-N 2-amino-n-[2-[4-bromo-2-(pyridine-2-carbonyl)anilino]-2-oxoethyl]acetamide Chemical compound NCC(=O)NCC(=O)NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=N1 NCVBBNHPRGOHFA-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- VDKALJALMRQMMZ-NRFANRHFSA-N (2s)-2-amino-n-[2-(2-benzoyl-4-chloro-n-methylanilino)-2-oxoethyl]-3-phenylpropanamide Chemical compound C([C@H](N)C(=O)NCC(=O)N(C)C=1C(=CC(Cl)=CC=1)C(=O)C=1C=CC=CC=1)C1=CC=CC=C1 VDKALJALMRQMMZ-NRFANRHFSA-N 0.000 claims description 2
- HTTNOVKQUPAUQD-INIZCTEOSA-N (2s)-2-amino-n-[2-(2-benzoyl-4-chloroanilino)-2-oxoethyl]-5-(diaminomethylideneamino)pentanamide Chemical compound NC(=N)NCCC[C@H](N)C(=O)NCC(=O)NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 HTTNOVKQUPAUQD-INIZCTEOSA-N 0.000 claims description 2
- FQLKUIGLPXMZIK-FQEVSTJZSA-N (2s)-2-amino-n-[2-(2-benzoyl-4-nitroanilino)-2-oxoethyl]-3-phenylpropanamide Chemical compound C([C@H](N)C(=O)NCC(=O)NC=1C(=CC(=CC=1)[N+]([O-])=O)C(=O)C=1C=CC=CC=1)C1=CC=CC=C1 FQLKUIGLPXMZIK-FQEVSTJZSA-N 0.000 claims description 2
- ZFIAFMFNIYHLTG-LBPRGKRZSA-N (2s)-2-amino-n-[2-(2-benzoyl-n-methyl-4-nitroanilino)-2-oxoethyl]propanamide Chemical compound C[C@H](N)C(=O)NCC(=O)N(C)C1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 ZFIAFMFNIYHLTG-LBPRGKRZSA-N 0.000 claims description 2
- ZRPOIQKPOONDHX-HNNXBMFYSA-N (2s)-2-amino-n-[2-[4-bromo-2-(pyridine-2-carbonyl)anilino]-2-oxoethyl]-4-methylpentanamide Chemical compound CC(C)C[C@H](N)C(=O)NCC(=O)NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=N1 ZRPOIQKPOONDHX-HNNXBMFYSA-N 0.000 claims description 2
- LFCYDGUHINTBOJ-AWEZNQCLSA-N (2s)-2-amino-n-[2-[4-bromo-2-(pyridine-2-carbonyl)anilino]-2-oxoethyl]-5-(diaminomethylideneamino)pentanamide Chemical compound NC(N)=NCCC[C@H](N)C(=O)NCC(=O)NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=N1 LFCYDGUHINTBOJ-AWEZNQCLSA-N 0.000 claims description 2
- WJUAYYOOYTWICN-JTQLQIEISA-N (2s)-2-amino-n-[2-[4-bromo-2-(pyridine-2-carbonyl)anilino]-2-oxoethyl]propanamide Chemical compound C[C@H](N)C(=O)NCC(=O)NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=N1 WJUAYYOOYTWICN-JTQLQIEISA-N 0.000 claims description 2
- NJCDDPBDHUIUKP-KRWDZBQOSA-N (2s)-n-[2-(2-benzoyl-4-nitroanilino)-2-oxoethyl]pyrrolidine-2-carboxamide Chemical compound C=1C=CC=CC=1C(=O)C1=CC([N+](=O)[O-])=CC=C1NC(=O)CNC(=O)[C@@H]1CCCN1 NJCDDPBDHUIUKP-KRWDZBQOSA-N 0.000 claims description 2
- OAEQXIARJNDJTL-UHFFFAOYSA-N 2-amino-n-[2-(2-benzoyl-4-chloro-n-methylanilino)-2-oxoethyl]acetamide Chemical compound NCC(=O)NCC(=O)N(C)C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 OAEQXIARJNDJTL-UHFFFAOYSA-N 0.000 claims description 2
- BGLIWPFJQFGODW-UHFFFAOYSA-N 2-amino-n-[2-(2-benzoyl-4-chloroanilino)-2-oxoethyl]acetamide Chemical compound NCC(=O)NCC(=O)NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 BGLIWPFJQFGODW-UHFFFAOYSA-N 0.000 claims description 2
- LTKOVYBBGBGKTA-SFHVURJKSA-N Avizafone Chemical compound NCCCC[C@H](N)C(=O)NCC(=O)N(C)C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 LTKOVYBBGBGKTA-SFHVURJKSA-N 0.000 claims description 2
- 235000019766 L-Lysine Nutrition 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 45
- 229940024874 benzophenone Drugs 0.000 claims 9
- 229940060038 chlorine Drugs 0.000 claims 7
- CRPXPIPMMOKSAG-SGTLLEGYSA-N (2S,3S)-2-amino-N-[2-[4-bromo-2-(pyridine-2-carbonyl)anilino]-2-oxoethyl]-3-methylpentanamide Chemical compound N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)NC1=C(C=C(C=C1)Br)C(C1=NC=CC=C1)=O CRPXPIPMMOKSAG-SGTLLEGYSA-N 0.000 claims 1
- NVOGGKXDMDDFEG-HNNXBMFYSA-N (2s)-2,6-diamino-n-[2-[4-bromo-2-(pyridine-2-carbonyl)anilino]-2-oxoethyl]hexanamide Chemical compound NCCCC[C@H](N)C(=O)NCC(=O)NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=N1 NVOGGKXDMDDFEG-HNNXBMFYSA-N 0.000 claims 1
- DXJQHCBNBNVNLR-IBGZPJMESA-N (2s)-2,6-diamino-n-[[4-(2-benzoyl-4-chlorophenyl)-5-methyl-1,2,4-triazol-3-yl]methyl]hexanamide Chemical compound CC1=NN=C(CNC(=O)[C@@H](N)CCCCN)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 DXJQHCBNBNVNLR-IBGZPJMESA-N 0.000 claims 1
- PSLVVDKNIOXMEJ-IBGZPJMESA-N (2s)-2,6-diamino-n-[[4-[4-chloro-2-(2-chlorobenzoyl)phenyl]-5-methyl-1,2,4-triazol-3-yl]methyl]hexanamide Chemical compound CC1=NN=C(CNC(=O)[C@@H](N)CCCCN)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl PSLVVDKNIOXMEJ-IBGZPJMESA-N 0.000 claims 1
- HRBYXALSEDXTQE-LBPRGKRZSA-N (2s)-2-amino-n-[[3-[4-chloro-2-(2-fluorobenzoyl)phenyl]-2-methylimidazol-4-yl]methyl]propanamide Chemical compound C[C@H](N)C(=O)NCC1=CN=C(C)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1F HRBYXALSEDXTQE-LBPRGKRZSA-N 0.000 claims 1
- TZXDVHUYNBXTQV-QFIPXVFZSA-N (2s)-2-amino-n-[[4-(2-benzoyl-4-chlorophenyl)-5-methyl-1,2,4-triazol-3-yl]methyl]-3-phenylpropanamide Chemical compound C([C@H](N)C(=O)NCC1=NN=C(N1C=1C(=CC(Cl)=CC=1)C(=O)C=1C=CC=CC=1)C)C1=CC=CC=C1 TZXDVHUYNBXTQV-QFIPXVFZSA-N 0.000 claims 1
- XYXUMFWVLVISNG-QFIPXVFZSA-N (2s)-2-amino-n-[[4-[4-chloro-2-(2-chlorobenzoyl)phenyl]-5-methyl-1,2,4-triazol-3-yl]methyl]-3-phenylpropanamide Chemical compound C([C@H](N)C(=O)NCC1=NN=C(N1C=1C(=CC(Cl)=CC=1)C(=O)C=1C(=CC=CC=1)Cl)C)C1=CC=CC=C1 XYXUMFWVLVISNG-QFIPXVFZSA-N 0.000 claims 1
- 241000555028 Sternidius alpha Species 0.000 claims 1
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 4
- 230000001773 anti-convulsant effect Effects 0.000 abstract description 3
- 239000001961 anticonvulsive agent Substances 0.000 abstract description 3
- 229960003965 antiepileptics Drugs 0.000 abstract description 3
- 239000003158 myorelaxant agent Substances 0.000 abstract description 3
- 239000000932 sedative agent Substances 0.000 abstract description 2
- 230000001624 sedative effect Effects 0.000 abstract description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 abstract 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 71
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 65
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- 239000000203 mixture Substances 0.000 description 47
- 238000002844 melting Methods 0.000 description 41
- 230000008018 melting Effects 0.000 description 41
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 38
- 150000002500 ions Chemical class 0.000 description 35
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- 238000004458 analytical method Methods 0.000 description 30
- 239000000047 product Substances 0.000 description 23
- 239000007787 solid Substances 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000000354 decomposition reaction Methods 0.000 description 18
- 229960000583 acetic acid Drugs 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000012362 glacial acetic acid Substances 0.000 description 13
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
- 235000011167 hydrochloric acid Nutrition 0.000 description 10
- 229960000443 hydrochloric acid Drugs 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000006260 foam Substances 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 229940073584 methylene chloride Drugs 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
- 150000007524 organic acids Chemical class 0.000 description 6
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 5
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
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- XOHKQMLLOMJLJP-UHFFFAOYSA-N n-[[7-chloro-5-(2-fluorophenyl)-2,3-dihydro-1h-1,4-benzodiazepin-2-yl]methyl]acetamide Chemical compound C12=CC(Cl)=CC=C2NC(CNC(=O)C)CN=C1C1=CC=CC=C1F XOHKQMLLOMJLJP-UHFFFAOYSA-N 0.000 description 1
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- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
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- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 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 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
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- 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
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
- C07K5/06043—Leu-amino acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06086—Dipeptides with the first amino acid being basic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06086—Dipeptides with the first amino acid being basic
- C07K5/06095—Arg-amino acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06165—Dipeptides with the first amino acid being heterocyclic and Pro-amino acid; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB36567/74A GB1517164A (en) | 1974-08-20 | 1974-08-20 | Substituted-phenyl ketones and a process for the manufacture thereof |
| GB36567 | 1974-08-20 | ||
| GB21821/75 | 1975-05-21 | ||
| GB2182175 | 1975-05-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1177069A true CA1177069A (en) | 1984-10-30 |
Family
ID=26255542
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000233720A Expired CA1177069A (en) | 1974-08-20 | 1975-08-19 | Phenyl ketones |
Country Status (19)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2754112A1 (de) * | 1977-12-05 | 1979-06-13 | Kali Chemie Pharma Gmbh | 1,4-benzodiazepinderivate, ihre salze und diese verbindungen enthaltende arzneipraeparate |
| IN184976B (enrdf_load_html_response) * | 1996-06-13 | 2000-10-14 | Ranbaxy Lab Ltd |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3709898A (en) * | 1971-02-09 | 1973-01-09 | Upjohn Co | Process for the production of triazolobenzodiazepines and intermediates |
| JPS526861B2 (enrdf_load_html_response) * | 1972-05-27 | 1977-02-25 | ||
| ZA735932B (en) * | 1972-09-21 | 1974-07-31 | Hoffmann La Roche | Benzodiazepine derivatives |
-
1974
- 1974-08-20 GB GB36567/74A patent/GB1517164A/en not_active Expired
-
1975
- 1975-08-13 CH CH1053375A patent/CH620900A5/de not_active IP Right Cessation
- 1975-08-18 PH PH17475A patent/PH16616A/en unknown
- 1975-08-18 IL IL47936A patent/IL47936A/xx unknown
- 1975-08-19 AT AT642175A patent/AT348985B/de not_active IP Right Cessation
- 1975-08-19 FR FR7525632A patent/FR2282261A1/fr active Granted
- 1975-08-19 ES ES440315A patent/ES440315A1/es not_active Expired
- 1975-08-19 NO NO752876A patent/NO150199C/no unknown
- 1975-08-19 AR AR260048A patent/AR217041A1/es active
- 1975-08-19 JP JP50099885A patent/JPS6018656B2/ja not_active Expired
- 1975-08-19 DK DK373975A patent/DK149284C/da active
- 1975-08-19 CA CA000233720A patent/CA1177069A/en not_active Expired
- 1975-08-19 SE SE7509268A patent/SE426319B/xx not_active IP Right Cessation
- 1975-08-19 LU LU73219A patent/LU73219A1/xx unknown
- 1975-08-19 AU AU84074/75A patent/AU502104B2/en not_active Expired
- 1975-08-19 DD DD187930A patent/DD123086A5/xx unknown
- 1975-08-20 FI FI752350A patent/FI66592C/fi not_active IP Right Cessation
- 1975-08-20 NL NL7509884A patent/NL7509884A/xx not_active Application Discontinuation
- 1975-08-20 DE DE19752537069 patent/DE2537069A1/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| AU8407475A (en) | 1977-02-24 |
| JPS6018656B2 (ja) | 1985-05-11 |
| DE2537069C2 (enrdf_load_html_response) | 1988-09-08 |
| IL47936A0 (en) | 1975-11-25 |
| DK373975A (da) | 1976-02-21 |
| DK149284B (da) | 1986-04-21 |
| LU73219A1 (enrdf_load_html_response) | 1977-04-15 |
| FI752350A7 (enrdf_load_html_response) | 1976-02-21 |
| ES440315A1 (es) | 1977-09-16 |
| ATA642175A (de) | 1978-08-15 |
| CH620900A5 (en) | 1980-12-31 |
| NO150199B (no) | 1984-05-28 |
| DD123086A5 (enrdf_load_html_response) | 1976-11-20 |
| DE2537069A1 (de) | 1976-03-04 |
| FR2282261B1 (enrdf_load_html_response) | 1978-11-10 |
| SE426319B (sv) | 1982-12-27 |
| AT348985B (de) | 1979-03-12 |
| GB1517164A (en) | 1978-07-12 |
| NO752876L (enrdf_load_html_response) | 1976-02-23 |
| NL7509884A (nl) | 1976-02-24 |
| IL47936A (en) | 1980-01-31 |
| FR2282261A1 (fr) | 1976-03-19 |
| AR217041A1 (es) | 1980-02-29 |
| NO150199C (no) | 1984-09-05 |
| FI66592B (fi) | 1984-07-31 |
| AU502104B2 (en) | 1979-07-12 |
| DK149284C (da) | 1986-10-13 |
| PH16616A (en) | 1983-11-28 |
| JPS51125048A (en) | 1976-11-01 |
| SE7509268L (sv) | 1976-02-23 |
| FI66592C (fi) | 1984-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |