IL44831A - ) - (-2- Benzoyl-4-oxo-B111,2,3,6,7- Hexahyuro-H4- Pira-Zeno] A, 1-2 [- Isoquoquinoline, its preparation and anti-worm mixtures against worms containing it - Google Patents
) - (-2- Benzoyl-4-oxo-B111,2,3,6,7- Hexahyuro-H4- Pira-Zeno] A, 1-2 [- Isoquoquinoline, its preparation and anti-worm mixtures against worms containing itInfo
- Publication number
- IL44831A IL44831A IL44831A IL4483174A IL44831A IL 44831 A IL44831 A IL 44831A IL 44831 A IL44831 A IL 44831A IL 4483174 A IL4483174 A IL 4483174A IL 44831 A IL44831 A IL 44831A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- hexahydro
- benzoyl
- oxo
- llb
- Prior art date
Links
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000843044 Stilesia Species 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 241001672171 Taenia hydatigena Species 0.000 description 1
- 241000356557 Taenia serialis Species 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 241001247909 Theileria cervi Species 0.000 description 1
- 241000999614 Thysaniezia Species 0.000 description 1
- 241000242541 Trematoda Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 210000000683 abdominal cavity Anatomy 0.000 description 1
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 210000000013 bile duct Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229920003123 carboxymethyl cellulose sodium Polymers 0.000 description 1
- 229940063834 carboxymethylcellulose sodium Drugs 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000001055 chewing effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 210000000188 diaphragm Anatomy 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 210000001165 lymph node Anatomy 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960000901 mepacrine Drugs 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- RJMUSRYZPJIFPJ-UHFFFAOYSA-N niclosamide Chemical compound OC1=CC=C(Cl)C=C1C(=O)NC1=CC=C([N+]([O-])=O)C=C1Cl RJMUSRYZPJIFPJ-UHFFFAOYSA-N 0.000 description 1
- 229960001920 niclosamide Drugs 0.000 description 1
- 229960005130 niridazole Drugs 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000011474 orchiectomy Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 210000004303 peritoneum Anatomy 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 210000004224 pleura Anatomy 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- CCSONKKTCMHYFI-UHFFFAOYSA-N pyrido[3,4-f]quinoxaline Chemical class C1=NC=C2C3=NC=CN=C3C=CC2=C1 CCSONKKTCMHYFI-UHFFFAOYSA-N 0.000 description 1
- GPKJTRJOBQGKQK-UHFFFAOYSA-N quinacrine Chemical compound C1=C(OC)C=C2C(NC(C)CCCN(CC)CC)=C(C=CC(Cl)=C3)C3=NC2=C1 GPKJTRJOBQGKQK-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- DZFMIYUMNRPCAB-UHFFFAOYSA-F stibophen Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C([O-])=C1O[Sb]1OC2=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C=C2O1 DZFMIYUMNRPCAB-UHFFFAOYSA-F 0.000 description 1
- 229940117007 stibophen Drugs 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2331713A DE2331713A1 (de) | 1973-06-22 | 1973-06-22 | Pyrazinoisochinolin-derivat |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL44831A0 IL44831A0 (en) | 1974-07-31 |
| IL44831A true IL44831A (en) | 1977-02-28 |
Family
ID=5884721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL44831A IL44831A (en) | 1973-06-22 | 1974-05-15 | ) - (-2- Benzoyl-4-oxo-B111,2,3,6,7- Hexahyuro-H4- Pira-Zeno] A, 1-2 [- Isoquoquinoline, its preparation and anti-worm mixtures against worms containing it |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3993760A (ja) |
| JP (1) | JPS5036497A (ja) |
| AU (1) | AU474590B2 (ja) |
| BE (1) | BE816607A (ja) |
| CH (2) | CH602725A5 (ja) |
| DE (1) | DE2331713A1 (ja) |
| DK (1) | DK137388C (ja) |
| EG (1) | EG14680A (ja) |
| ES (1) | ES427583A1 (ja) |
| FR (1) | FR2234005B1 (ja) |
| GB (1) | GB1417359A (ja) |
| HU (1) | HU170191B (ja) |
| IL (1) | IL44831A (ja) |
| NL (1) | NL7408395A (ja) |
| ZA (1) | ZA743084B (ja) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2508947C3 (de) * | 1975-03-01 | 1982-02-25 | Merck Patent Gmbh, 6100 Darmstadt | Verfahren zur Herstellung von 4-Oxo-1,2,3,6,7, 11b-hexahydro-4H-pyrazino [2,1-a] isochinolinen |
| IN157936B (ja) * | 1982-07-08 | 1986-07-26 | Korea Advanced Inst Sci & Tech | |
| WO1987006132A1 (en) * | 1986-04-07 | 1987-10-22 | The Upjohn Company | Anthelmintic quaternaryalkyl acylhydrazones, method of use and compositions |
| US9932337B2 (en) * | 2014-11-21 | 2018-04-03 | Merck Patent Gmbh | Method for the production of Praziquantel and precursors thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1470062A1 (de) * | 1964-02-06 | 1969-05-08 | E Merck Ag Fa | Verfahren zur Herstellung von 1,2,3,6,7,11 b-Hexahydro-4 H-pyrazino-[2,1-a]-isochinolinen |
-
1973
- 1973-06-22 DE DE2331713A patent/DE2331713A1/de not_active Withdrawn
-
1974
- 1974-05-14 ZA ZA00743084A patent/ZA743084B/xx unknown
- 1974-05-15 IL IL44831A patent/IL44831A/en unknown
- 1974-06-07 CH CH781974A patent/CH602725A5/xx not_active IP Right Cessation
- 1974-06-07 CH CH999277A patent/CH601297A5/xx not_active IP Right Cessation
- 1974-06-07 GB GB2533774A patent/GB1417359A/en not_active Expired
- 1974-06-18 AU AU70156/74A patent/AU474590B2/en not_active Expired
- 1974-06-19 JP JP49070782A patent/JPS5036497A/ja active Pending
- 1974-06-20 HU HUME1746A patent/HU170191B/hu unknown
- 1974-06-20 BE BE145661A patent/BE816607A/xx unknown
- 1974-06-21 US US05/481,792 patent/US3993760A/en not_active Expired - Lifetime
- 1974-06-21 NL NL7408395A patent/NL7408395A/xx not_active Application Discontinuation
- 1974-06-21 DK DK334274A patent/DK137388C/da active
- 1974-06-22 ES ES427583A patent/ES427583A1/es not_active Expired
- 1974-06-22 EG EG235/74A patent/EG14680A/xx active
- 1974-06-24 FR FR7421811A patent/FR2234005B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| HU170191B (ja) | 1977-04-28 |
| US3993760A (en) | 1976-11-23 |
| FR2234005B1 (ja) | 1978-03-24 |
| CH602725A5 (ja) | 1978-07-31 |
| GB1417359A (en) | 1975-12-10 |
| FR2234005A1 (ja) | 1975-01-17 |
| CH601297A5 (ja) | 1978-07-14 |
| BE816607A (fr) | 1974-12-20 |
| DK137388B (da) | 1978-02-27 |
| JPS5036497A (ja) | 1975-04-05 |
| DE2331713A1 (de) | 1975-01-23 |
| ZA743084B (en) | 1975-05-28 |
| AU474590B2 (en) | 1976-07-29 |
| NL7408395A (ja) | 1974-12-24 |
| DK137388C (da) | 1978-08-07 |
| EG14680A (en) | 1984-09-30 |
| DK334274A (ja) | 1975-02-17 |
| IL44831A0 (en) | 1974-07-31 |
| ES427583A1 (es) | 1976-11-16 |
| AU7015674A (en) | 1975-12-18 |
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