CA1036606A - 2-acyl-4-oxo-pyrazino-isoquinoline derivatives and process for the preparation thereof - Google Patents
2-acyl-4-oxo-pyrazino-isoquinoline derivatives and process for the preparation thereofInfo
- Publication number
- CA1036606A CA1036606A CA216,069A CA216069A CA1036606A CA 1036606 A CA1036606 A CA 1036606A CA 216069 A CA216069 A CA 216069A CA 1036606 A CA1036606 A CA 1036606A
- Authority
- CA
- Canada
- Prior art keywords
- hpi
- oxo
- pyrazino
- isoquinoline
- hexahydro
- 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
- 238000000034 method Methods 0.000 title claims description 52
- 238000002360 preparation method Methods 0.000 title description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 79
- 239000002253 acid Substances 0.000 claims abstract description 38
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000002596 lactones Chemical class 0.000 claims abstract description 7
- 239000005711 Benzoic acid Substances 0.000 claims abstract description 5
- 150000001540 azides Chemical class 0.000 claims abstract description 5
- 235000010233 benzoic acid Nutrition 0.000 claims abstract description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 4
- GTRDOUXISKJZGL-UHFFFAOYSA-N 1,2,3,6,7,11b-hexahydropyrazino[2,1-a]isoquinolin-4-one Chemical compound C1=CC=C2C3CNCC(=O)N3CCC2=C1 GTRDOUXISKJZGL-UHFFFAOYSA-N 0.000 claims abstract 3
- -1 acyl radical Chemical class 0.000 claims description 272
- 150000001875 compounds Chemical class 0.000 claims description 99
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 230000000875 corresponding effect Effects 0.000 claims description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 29
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- 239000000126 substance Substances 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 239000011737 fluorine Substances 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 150000007513 acids Chemical class 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 9
- 150000003863 ammonium salts Chemical class 0.000 claims description 9
- 150000008064 anhydrides Chemical class 0.000 claims description 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 230000003287 optical effect Effects 0.000 claims description 9
- 239000002262 Schiff base Substances 0.000 claims description 8
- 150000004753 Schiff bases Chemical class 0.000 claims description 8
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 8
- 125000000468 ketone group Chemical group 0.000 claims description 8
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 150000003141 primary amines Chemical class 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
- FSVJFNAIGNNGKK-UHFFFAOYSA-N 2-[cyclohexyl(oxo)methyl]-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one Chemical group C1C(C2=CC=CC=C2CC2)N2C(=O)CN1C(=O)C1CCCCC1 FSVJFNAIGNNGKK-UHFFFAOYSA-N 0.000 claims 3
- KTRPEDSWLBXJKC-UHFFFAOYSA-N 1-(pyridine-2-carbonyl)-1,2,3,6,7,11b-hexahydropyrazino[2,1-a]isoquinolin-4-one Chemical compound N1CC(=O)N2CCC3=CC=CC=C3C2C1C(=O)C1=CC=CC=N1 KTRPEDSWLBXJKC-UHFFFAOYSA-N 0.000 claims 2
- BYNWNSPFVZKHAP-UHFFFAOYSA-N 2-(2-fluorobenzoyl)-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one Chemical group FC1=CC=CC=C1C(=O)N1CC(=O)N(CCC=2C3=CC=CC=2)C3C1 BYNWNSPFVZKHAP-UHFFFAOYSA-N 0.000 claims 2
- YHVXIGITKMANAK-UHFFFAOYSA-N 2-(2-methylpropanoyl)-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1=CC=C2C3CN(C(=O)C(C)C)CC(=O)N3CCC2=C1 YHVXIGITKMANAK-UHFFFAOYSA-N 0.000 claims 2
- HQFCQXREAJIDQF-UHFFFAOYSA-N 2-(3-aminobenzoyl)-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one Chemical group NC1=CC=CC(C(=O)N2CC(=O)N3C(C4=CC=CC=C4CC3)C2)=C1 HQFCQXREAJIDQF-UHFFFAOYSA-N 0.000 claims 2
- ZUJZQFWOJYTTJE-UHFFFAOYSA-N 2-(3-fluorobenzoyl)-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one Chemical group FC1=CC=CC(C(=O)N2CC(=O)N3C(C4=CC=CC=C4CC3)C2)=C1 ZUJZQFWOJYTTJE-UHFFFAOYSA-N 0.000 claims 2
- ISZJJLUQBKDSNQ-UHFFFAOYSA-N 2-(4-aminobenzoyl)-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one Chemical group C1=CC(N)=CC=C1C(=O)N1CC(=O)N(CCC=2C3=CC=CC=2)C3C1 ISZJJLUQBKDSNQ-UHFFFAOYSA-N 0.000 claims 2
- RWQQSRDAZCPNIB-UHFFFAOYSA-N 2-(4-fluorobenzoyl)-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one Chemical group C1=CC(F)=CC=C1C(=O)N1CC(=O)N(CCC=2C3=CC=CC=2)C3C1 RWQQSRDAZCPNIB-UHFFFAOYSA-N 0.000 claims 2
- OKTGUGBZQBTMHZ-UHFFFAOYSA-N 2-(4-hydroxycyclohexanecarbonyl)-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1CC(O)CCC1C(=O)N1CC(=O)N(CCC=2C3=CC=CC=2)C3C1 OKTGUGBZQBTMHZ-UHFFFAOYSA-N 0.000 claims 2
- UGUUPDMTEOEELN-UHFFFAOYSA-N 2-(4-nitrobenzoyl)-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one Chemical group C1=CC([N+](=O)[O-])=CC=C1C(=O)N1CC(=O)N(CCC=2C3=CC=CC=2)C3C1 UGUUPDMTEOEELN-UHFFFAOYSA-N 0.000 claims 2
- HNIDYTQURQDBHQ-UHFFFAOYSA-N 2-(4-oxocyclohexanecarbonyl)-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1C(C2=CC=CC=C2CC2)N2C(=O)CN1C(=O)C1CCC(=O)CC1 HNIDYTQURQDBHQ-UHFFFAOYSA-N 0.000 claims 2
- BXODIXWTKRLZEO-UHFFFAOYSA-N 2-(cyclobutanecarbonyl)-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1C(C2=CC=CC=C2CC2)N2C(=O)CN1C(=O)C1CCC1 BXODIXWTKRLZEO-UHFFFAOYSA-N 0.000 claims 2
- TYINGBVLPBITAY-UHFFFAOYSA-N 2-(cycloheptanecarbonyl)-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1C(C2=CC=CC=C2CC2)N2C(=O)CN1C(=O)C1CCCCCC1 TYINGBVLPBITAY-UHFFFAOYSA-N 0.000 claims 2
- VWFZWCLLTSCGTQ-UHFFFAOYSA-N 2-(cyclohex-3-ene-1-carbonyl)-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1C(C2=CC=CC=C2CC2)N2C(=O)CN1C(=O)C1CCC=CC1 VWFZWCLLTSCGTQ-UHFFFAOYSA-N 0.000 claims 2
- JGIKIBLSNIFOGF-UHFFFAOYSA-N 2-(cyclopentanecarbonyl)-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1C(C2=CC=CC=C2CC2)N2C(=O)CN1C(=O)C1CCCC1 JGIKIBLSNIFOGF-UHFFFAOYSA-N 0.000 claims 2
- WQFOCHFXTXVWCZ-UHFFFAOYSA-N 2-(cyclopropanecarbonyl)-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1C(C2=CC=CC=C2CC2)N2C(=O)CN1C(=O)C1CC1 WQFOCHFXTXVWCZ-UHFFFAOYSA-N 0.000 claims 2
- CEUBACFSGQHTJO-UHFFFAOYSA-N 2-[4-(dimethylamino)benzoyl]-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1=CC(N(C)C)=CC=C1C(=O)N1CC(=O)N(CCC=2C3=CC=CC=2)C3C1 CEUBACFSGQHTJO-UHFFFAOYSA-N 0.000 claims 2
- BXKBULYSFQRCPX-UHFFFAOYSA-N 2-[4-(methylamino)benzoyl]-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1=CC(NC)=CC=C1C(=O)N1CC(=O)N(CCC=2C3=CC=CC=2)C3C1 BXKBULYSFQRCPX-UHFFFAOYSA-N 0.000 claims 2
- YRRCEEUJIHMQFB-UHFFFAOYSA-N 2-acetyl-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1=CC=C2C3CN(C(=O)C)CC(=O)N3CCC2=C1 YRRCEEUJIHMQFB-UHFFFAOYSA-N 0.000 claims 2
- KYPNGFZZGICLHT-UHFFFAOYSA-N 2-methoxy-n-[3-(4-oxo-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinoline-2-carbonyl)phenyl]acetamide Chemical compound COCC(=O)NC1=CC=CC(C(=O)N2CC(=O)N3C(C4=CC=CC=C4CC3)C2)=C1 KYPNGFZZGICLHT-UHFFFAOYSA-N 0.000 claims 2
- LPWKVXGUINODDK-UHFFFAOYSA-N 2-methoxy-n-[4-(4-oxo-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinoline-2-carbonyl)phenyl]acetamide Chemical compound C1=CC(NC(=O)COC)=CC=C1C(=O)N1CC(=O)N(CCC=2C3=CC=CC=2)C3C1 LPWKVXGUINODDK-UHFFFAOYSA-N 0.000 claims 2
- LRHVNSQAAMMPLW-UHFFFAOYSA-N 2-propanoyl-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1=CC=C2C3CN(C(=O)CC)CC(=O)N3CCC2=C1 LRHVNSQAAMMPLW-UHFFFAOYSA-N 0.000 claims 2
- 125000004185 ester group Chemical group 0.000 claims 2
- IROUTQZWQQADMD-UHFFFAOYSA-N n-[3-(4-oxo-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinoline-2-carbonyl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C(=O)N2CC(=O)N3C(C4=CC=CC=C4CC3)C2)=C1 IROUTQZWQQADMD-UHFFFAOYSA-N 0.000 claims 2
- HBIWZWLCSUXHTE-UHFFFAOYSA-N n-[4-(4-oxo-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinoline-2-carbonyl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(=O)N1CC(=O)N(CCC=2C3=CC=CC=2)C3C1 HBIWZWLCSUXHTE-UHFFFAOYSA-N 0.000 claims 2
- LRYZVHZMORRBFD-UHFFFAOYSA-N n-[4-(4-oxo-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinoline-2-carbonyl)phenyl]formamide Chemical group C1=CC(NC=O)=CC=C1C(=O)N1CC(=O)N(CCC=2C3=CC=CC=2)C3C1 LRYZVHZMORRBFD-UHFFFAOYSA-N 0.000 claims 2
- JLFCQSOHRCCHMW-UHFFFAOYSA-N 2-(pyridine-3-carbonyl)-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1C(C2=CC=CC=C2CC2)N2C(=O)CN1C(=O)C1=CC=CN=C1 JLFCQSOHRCCHMW-UHFFFAOYSA-N 0.000 claims 1
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- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
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- 125000004429 atom Chemical group 0.000 claims 1
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- KBGFVFRWGMVLGQ-UHFFFAOYSA-N n-[3-(4-oxo-3,6,7,11b-tetrahydro-1h-pyrazino[2,1-a]isoquinoline-2-carbonyl)phenyl]formamide Chemical group O=CNC1=CC=CC(C(=O)N2CC(=O)N3C(C4=CC=CC=C4CC3)C2)=C1 KBGFVFRWGMVLGQ-UHFFFAOYSA-N 0.000 claims 1
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- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- RZFBEFUNINJXRQ-UHFFFAOYSA-M sodium ethyl xanthate Chemical compound [Na+].CCOC([S-])=S RZFBEFUNINJXRQ-UHFFFAOYSA-M 0.000 description 1
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- 125000001302 tertiary amino group Chemical group 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
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- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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- 125000003944 tolyl group Chemical group 0.000 description 1
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- AECHPKVYOLOZLF-UHFFFAOYSA-N trifluoro(phenyl)-$l^{4}-sulfane Chemical compound FS(F)(F)C1=CC=CC=C1 AECHPKVYOLOZLF-UHFFFAOYSA-N 0.000 description 1
- LEMQFBIYMVUIIG-UHFFFAOYSA-N trifluoroborane;hydrofluoride Chemical compound F.FB(F)F LEMQFBIYMVUIIG-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
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- NSBGJRFJIJFMGW-UHFFFAOYSA-N trisodium;stiborate Chemical compound [Na+].[Na+].[Na+].[O-][Sb]([O-])([O-])=O NSBGJRFJIJFMGW-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Fodder In General (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2362539A DE2362539C2 (de) | 1973-12-17 | 1973-12-17 | 2-Acyl-4-oxo-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isochinoline, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1036606A true CA1036606A (en) | 1978-08-15 |
Family
ID=5900929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA216,069A Expired CA1036606A (en) | 1973-12-17 | 1974-12-16 | 2-acyl-4-oxo-pyrazino-isoquinoline derivatives and process for the preparation thereof |
Country Status (35)
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4196291A (en) * | 1973-12-17 | 1980-04-01 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | 2-Acyl-4-oxo-pyrazino-isoquinoline derivatives and process for the preparation thereof |
| US4141978A (en) * | 1973-12-17 | 1979-02-27 | Merck Patent Gesellschaft Mit Beschrankter Haftung | 2-Acyl-4-oxo-pyrazino-isoquinoline derivatives and process for the preparation thereof |
| DE2441261A1 (de) * | 1974-08-28 | 1976-03-18 | Merck Patent Gmbh | Ringsubstituierte pyrazino-isochinolin-derivat und verfahren zu ihrer herstellung |
| US4120961A (en) * | 1974-08-28 | 1978-10-17 | E. Merck | Ring substituted pyrazino-isoquinoline derivatives and their preparation |
| US4162319A (en) * | 1974-08-28 | 1979-07-24 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Ring substituted pyrazino-isoquinoline derivatives and their preparation |
| DE2841668A1 (de) * | 1978-09-25 | 1980-04-10 | Bayer Ag | Medikiertes tierfutter auf basis lebermehl |
| US4303659A (en) | 1979-08-22 | 1981-12-01 | Pfizer Inc. | Schistosomicidal compositions |
| FR2520740A1 (fr) * | 1982-01-29 | 1983-08-05 | Sanofi Sa | Procede pour la preparation d'acyl-2-hexahydro-1,3,4,6,7,11b-2h-pyrazino (2,1-a) isoquinoleinones-4 et intermediaires |
| EP0134984B1 (en) * | 1983-07-16 | 1988-07-13 | Beecham Group Plc | Benzazepine and benzoxazepine derivatives |
| DE3634755A1 (de) * | 1986-10-11 | 1988-04-14 | Bayer Ag | Dermale behandlung von wurmerkrankungen der katze mit praziquantel |
| NZ247278A (en) * | 1991-02-12 | 1995-03-28 | Ancare Distributors | Veterinary anthelmintic drench comprising a suspension of praziquantel in a liquid carrier |
| GB9321854D0 (en) * | 1993-10-22 | 1993-12-15 | Zeneca Ltd | Pyridazino quinoline compounds |
| DE19628776A1 (de) | 1996-07-17 | 1998-01-22 | Bayer Ag | Oral applizierbare Granulate von Hexahydropyrazinderivaten |
| US6429211B1 (en) | 2000-05-23 | 2002-08-06 | Bayer Corporation | Praziquantel compounds for treating diseases due to Sarcocystis Neospora Toxoplasma and Isospora |
| US7396819B2 (en) | 2003-08-08 | 2008-07-08 | Virbac Corporation | Anthelmintic formulations |
| DE10358525A1 (de) * | 2003-12-13 | 2005-07-07 | Bayer Healthcare Ag | Endoparasitizide Mittel zur topischen Applikation |
| RU2266906C1 (ru) * | 2004-04-29 | 2005-12-27 | Общество с ограниченной ответственностью "Исследовательский Институт Химического Разнообразия" (ООО "Исследовательский Институт Химического Разнообразия") | Анелированные карбамоилазагетероциклы, способы их получения (варианты), фармацевтическая композиция, фокусированная библиотека |
| DE102004055316A1 (de) * | 2004-11-16 | 2006-05-18 | Bayer Healthcare Ag | Verhinderung vertikaler Endoparasiten-Infektionen |
| KR100682506B1 (ko) * | 2005-01-18 | 2007-02-15 | (주)젠크로스 | 프라지콴텔, 또는 이의 염을 포함하는 약학 조성물 |
| DE102005011779A1 (de) * | 2005-03-11 | 2006-09-14 | Bayer Healthcare Ag | Endoparasitizide Mittel |
| CA2609574A1 (en) * | 2005-06-09 | 2006-12-21 | Schering-Plough Ltd. | Control of parasites in animals by n-[(phenyloxy)phenyl]-1,1,1-trifluoromethanesulfonamide and n-[(phenylsulfanyl)phenyl]-1,1,1-trifluoromethanesulfonamide derivatives |
| FR2912145B1 (fr) * | 2007-02-02 | 2009-03-06 | Servier Lab | Nouveaux derives tricycliques,leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| ITPD20070274A1 (it) * | 2007-08-08 | 2009-02-09 | Sanypet S P A | Crocchetta per animali e metodo per la sua produzione |
| ES2748136T3 (es) | 2007-10-15 | 2020-03-13 | United Animal Health Inc | Método para aumentar el rendimiento de las crías |
| DE102008022520A1 (de) | 2008-05-07 | 2009-11-12 | Bayer Animal Health Gmbh | Feste Arzneimittelformulierung mit verzögerter Freisetzung |
| AP2909A (en) | 2009-03-17 | 2014-05-31 | Concert Pharmaceuticals Inc | Pyrazinoisoquinoline Compounds |
| CN102093346B (zh) * | 2010-03-16 | 2012-09-05 | 浙江金伯士药业有限公司 | 一种吡喹酮的制备方法 |
| US8889687B2 (en) | 2011-03-04 | 2014-11-18 | Concert Pharmaceuticals, Inc. | Deuterated pyrazinoisoquinoline compounds |
| CN103910725B (zh) * | 2013-01-09 | 2015-12-02 | 江南大学 | 一类吡喹酮类似物、其制备方法和用途 |
-
1973
- 1973-12-17 DE DE2362539A patent/DE2362539C2/de not_active Expired
-
1974
- 1974-10-29 LU LU71204A patent/LU71204A1/xx unknown
- 1974-11-12 GB GB4886174A patent/GB1441554A/en not_active Expired
- 1974-11-12 ZA ZA00747253A patent/ZA747253B/xx unknown
- 1974-11-18 IE IE2373/74A patent/IE40124B1/xx unknown
- 1974-11-22 IN IN2601/CAL/74A patent/IN139511B/en unknown
- 1974-11-29 IL IL46162A patent/IL46162A/xx unknown
- 1974-12-11 CS CS748427A patent/CS241002B2/cs unknown
- 1974-12-12 PH PH16619A patent/PH14220A/en unknown
- 1974-12-13 RO RO7480781A patent/RO66907A/ro unknown
- 1974-12-13 AR AR256891A patent/AR208527A1/es active
- 1974-12-13 SE SE7415686A patent/SE422211B/xx not_active IP Right Cessation
- 1974-12-13 AT AT996274A patent/AT346334B/de not_active IP Right Cessation
- 1974-12-16 PL PL1974187324A patent/PL99088B1/pl unknown
- 1974-12-16 DK DK654274A patent/DK141845C/da not_active IP Right Cessation
- 1974-12-16 BE BE151546A patent/BE823400A/xx not_active IP Right Cessation
- 1974-12-16 CA CA216,069A patent/CA1036606A/en not_active Expired
- 1974-12-16 FI FI3632/74A patent/FI59594C/fi active
- 1974-12-16 DD DD183078A patent/DD115908A5/xx unknown
- 1974-12-16 HU HU74ME00001815A patent/HU170858B/hu unknown
- 1974-12-16 NO NO744521A patent/NO142304C/no unknown
- 1974-12-16 PL PL1974176506A patent/PL94074B1/pl unknown
- 1974-12-16 US US05/533,467 patent/US4001411A/en not_active Expired - Lifetime
- 1974-12-16 FR FR7441356A patent/FR2254343B1/fr not_active Expired
- 1974-12-16 ES ES432974A patent/ES432974A1/es not_active Expired
- 1974-12-16 PL PL1974187325A patent/PL99105B1/pl unknown
- 1974-12-17 NL NLAANVRAGE7416432,A patent/NL185406C/xx not_active IP Right Cessation
- 1974-12-17 CH CH1675474A patent/CH612195A5/xx not_active IP Right Cessation
- 1974-12-17 OA OA55366A patent/OA04868A/xx unknown
- 1974-12-17 GR GR5764A patent/GR60708B/el unknown
- 1974-12-17 JP JP49145536A patent/JPS5826352B2/ja not_active Expired
- 1974-12-17 SU SU742084647A patent/SU631070A3/ru active
- 1974-12-17 YU YU3361/74A patent/YU41288B/xx unknown
-
1975
- 1975-09-26 AR AR260558A patent/AR208715A1/es active
- 1975-10-07 ES ES441546A patent/ES441546A1/es not_active Expired
-
1976
- 1976-11-25 SU SU762423403A patent/SU668603A3/ru active
- 1976-11-29 SU SU762423402A patent/SU625613A3/ru active
-
1978
- 1978-02-07 GT GT197850798A patent/GT197850798A/es unknown
- 1978-11-09 CH CH1154278A patent/CH621788A5/de not_active IP Right Cessation
- 1978-11-09 CH CH1154378A patent/CH620442A5/de not_active IP Right Cessation
- 1978-11-20 IT IT7851978A patent/IT7851978A0/it unknown
-
1979
- 1979-03-15 HK HK133/79A patent/HK13379A/xx unknown
- 1979-04-02 KE KE2946A patent/KE2946A/xx unknown
Also Published As
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