NO135173B - - Google Patents
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- Publication number
- NO135173B NO135173B NO1450/71A NO145071A NO135173B NO 135173 B NO135173 B NO 135173B NO 1450/71 A NO1450/71 A NO 1450/71A NO 145071 A NO145071 A NO 145071A NO 135173 B NO135173 B NO 135173B
- Authority
- NO
- Norway
- Prior art keywords
- benzodiazepine
- phenyl
- chloro
- trifluoromethyl
- recrystallized
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 20
- -1 nitro, amino Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 239000012965 benzophenone Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 229940049706 benzodiazepine Drugs 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229940024874 benzophenone Drugs 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 2
- OYOUQHVDCKOOAL-UHFFFAOYSA-N 7-Aminonitrazepam Chemical compound C12=CC(N)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 OYOUQHVDCKOOAL-UHFFFAOYSA-N 0.000 description 2
- PEACRWGRSQUWBX-UHFFFAOYSA-N 7-methoxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(OC)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 PEACRWGRSQUWBX-UHFFFAOYSA-N 0.000 description 2
- 101100520142 Caenorhabditis elegans pin-2 gene Proteins 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CJUMAFVKTCBCJK-UHFFFAOYSA-N N-benzyloxycarbonylglycine Chemical compound OC(=O)CNC(=O)OCC1=CC=CC=C1 CJUMAFVKTCBCJK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NTVANYIWXRUGQR-UHFFFAOYSA-N 5-(4-chlorophenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C1=CC(Cl)=CC=C1C1=NCC(=O)NC2=CC=CC=C12 NTVANYIWXRUGQR-UHFFFAOYSA-N 0.000 description 1
- IVUAAOBNUNMJQC-UHFFFAOYSA-N 5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical class C12=CC=CC=C2NC(=O)CN=C1C1=CC=CC=C1 IVUAAOBNUNMJQC-UHFFFAOYSA-N 0.000 description 1
- AOJRGBWRJGTLDT-UHFFFAOYSA-N 5-phenyl-8-(trifluoromethyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C=1C(C(F)(F)F)=CC=C2C=1NC(=O)CN=C2C1=CC=CC=C1 AOJRGBWRJGTLDT-UHFFFAOYSA-N 0.000 description 1
- LODQZIQLZDHYJG-UHFFFAOYSA-N 7,9-dichloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC(Cl)=C2NC(=O)CN=C1C1=CC=CC=C1 LODQZIQLZDHYJG-UHFFFAOYSA-N 0.000 description 1
- JHTJXLGLYZQIGI-UHFFFAOYSA-N 7-Acetamidonitrazepam Chemical compound C12=CC(NC(=O)C)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 JHTJXLGLYZQIGI-UHFFFAOYSA-N 0.000 description 1
- KMADJPBGARDOAO-UHFFFAOYSA-N 7-bromo-5-(2-fluorophenyl)-1-methyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(C)C2=CC=C(Br)C=C2C=1C1=CC=CC=C1F KMADJPBGARDOAO-UHFFFAOYSA-N 0.000 description 1
- KVXRLJHLTJKYKB-UHFFFAOYSA-N 7-bromo-5-(4-methylphenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C1=CC(C)=CC=C1C1=NCC(=O)NC2=CC=C(Br)C=C12 KVXRLJHLTJKYKB-UHFFFAOYSA-N 0.000 description 1
- SRDIBKOFJZSMMA-UHFFFAOYSA-N 7-bromo-8-methoxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C1=2C=C(Br)C(OC)=CC=2NC(=O)CN=C1C1=CC=CC=C1 SRDIBKOFJZSMMA-UHFFFAOYSA-N 0.000 description 1
- DOGMLEAYMUQBTO-UHFFFAOYSA-N 7-chloro-5-(2-hydroxyphenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound ClC=1C=CC2=C(C(=NCC(N2)=O)C2=C(C=CC=C2)O)C1 DOGMLEAYMUQBTO-UHFFFAOYSA-N 0.000 description 1
- VMRHOEBUTQIEKP-UHFFFAOYSA-N 7-chloro-5-(2-methoxyphenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound COC1=CC=CC=C1C1=NCC(=O)NC2=CC=C(Cl)C=C12 VMRHOEBUTQIEKP-UHFFFAOYSA-N 0.000 description 1
- PLSKGUKSIDTEPG-UHFFFAOYSA-N 7-chloro-5-(2-methoxyphenyl)-1-methyl-3H-1,4-benzodiazepin-2-one Chemical compound COC1=C(C=CC=C1)C1=NCC(=O)N(C)C2=CC=C(Cl)C=C12 PLSKGUKSIDTEPG-UHFFFAOYSA-N 0.000 description 1
- AOOWAUAQVUYDCR-UHFFFAOYSA-N 7-chloro-5-(2-methylphenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound CC1=CC=CC=C1C1=NCC(=O)NC2=CC=C(Cl)C=C12 AOOWAUAQVUYDCR-UHFFFAOYSA-N 0.000 description 1
- JPSGKFVCUQLFJS-UHFFFAOYSA-N 7-chloro-5-(3-methoxyphenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound COC1=CC=CC(C=2C3=CC(Cl)=CC=C3NC(=O)CN=2)=C1 JPSGKFVCUQLFJS-UHFFFAOYSA-N 0.000 description 1
- BWQOGLAANRWTBZ-UHFFFAOYSA-N 7-chloro-5-(4-methoxyphenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C1=CC(OC)=CC=C1C1=NCC(=O)NC2=CC=C(Cl)C=C12 BWQOGLAANRWTBZ-UHFFFAOYSA-N 0.000 description 1
- CWAPDOCJCFWNIE-UHFFFAOYSA-N 7-hydroxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(O)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 CWAPDOCJCFWNIE-UHFFFAOYSA-N 0.000 description 1
- ZZLQGKUTUGIQNL-UHFFFAOYSA-N 7-methyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(C)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 ZZLQGKUTUGIQNL-UHFFFAOYSA-N 0.000 description 1
- PSRFZVMHJDITLA-UHFFFAOYSA-N 7-methylsulfinyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC([S+]([O-])C)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 PSRFZVMHJDITLA-UHFFFAOYSA-N 0.000 description 1
- RXCDCVYRSFPGHQ-UHFFFAOYSA-N 7-methylsulfonyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(S(=O)(=O)C)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 RXCDCVYRSFPGHQ-UHFFFAOYSA-N 0.000 description 1
- ZQNMREXZDXVUPB-UHFFFAOYSA-N 8-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C=1C(Cl)=CC=C2C=1NC(=O)CN=C2C1=CC=CC=C1 ZQNMREXZDXVUPB-UHFFFAOYSA-N 0.000 description 1
- OGDLFFYXUKTNDD-UHFFFAOYSA-N 8-methoxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C=1C(OC)=CC=C2C=1NC(=O)CN=C2C1=CC=CC=C1 OGDLFFYXUKTNDD-UHFFFAOYSA-N 0.000 description 1
- NOJVFPSKPFOJHX-UHFFFAOYSA-N 8-nitro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C=1C([N+](=O)[O-])=CC=C2C=1NC(=O)CN=C2C1=CC=CC=C1 NOJVFPSKPFOJHX-UHFFFAOYSA-N 0.000 description 1
- NUXRLDCCKDXYCK-UHFFFAOYSA-N 9-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound ClC1=CC=CC2=C1NC(=O)CN=C2C1=CC=CC=C1 NUXRLDCCKDXYCK-UHFFFAOYSA-N 0.000 description 1
- YYSSSENOSHKUEM-UHFFFAOYSA-N 9-nitro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound [O-][N+](=O)C1=CC=CC2=C1NC(=O)CN=C2C1=CC=CC=C1 YYSSSENOSHKUEM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- HVVKOBYMMJCFSX-UHFFFAOYSA-N [2-(phenylmethoxycarbonylamino)acetyl] 2-(phenylmethoxycarbonylamino)acetate Chemical compound C=1C=CC=CC=1COC(=O)NCC(=O)OC(=O)CNC(=O)OCC1=CC=CC=C1 HVVKOBYMMJCFSX-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 description 1
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- KVDNWGDSNIDQLB-UHFFFAOYSA-N benzyl n-[2-(2-benzoyl-4-chloroanilino)-2-oxoethyl]carbamate Chemical compound C=1C=CC=CC=1C(=O)C1=CC(Cl)=CC=C1NC(=O)CNC(=O)OCC1=CC=CC=C1 KVDNWGDSNIDQLB-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical class [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- VPAYQWRBBOGGPY-UHFFFAOYSA-N diclazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1Cl VPAYQWRBBOGGPY-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ZRKDDZBVSZLOFS-UHFFFAOYSA-N flubromazepam Chemical compound FC1=CC=CC=C1C1=NCC(=O)NC2=CC=C(Br)C=C12 ZRKDDZBVSZLOFS-UHFFFAOYSA-N 0.000 description 1
- ROYOYTLGDLIGBX-UHFFFAOYSA-N fludiazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F ROYOYTLGDLIGBX-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- GWUSZQUVEVMBPI-UHFFFAOYSA-N nimetazepam Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 GWUSZQUVEVMBPI-UHFFFAOYSA-N 0.000 description 1
- KJONHKAYOJNZEC-UHFFFAOYSA-N nitrazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1 KJONHKAYOJNZEC-UHFFFAOYSA-N 0.000 description 1
- AKPLHCDWDRPJGD-UHFFFAOYSA-N nordazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 AKPLHCDWDRPJGD-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- UUBMOUNXQFMBQF-UHFFFAOYSA-N ro5-2904 Chemical compound C12=CC(C(F)(F)F)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 UUBMOUNXQFMBQF-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65B—MACHINES, APPARATUS OR DEVICES FOR, OR METHODS OF, PACKAGING ARTICLES OR MATERIALS; UNPACKING
- B65B35/00—Supplying, feeding, arranging or orientating articles to be packaged
- B65B35/30—Arranging and feeding articles in groups
- B65B35/50—Stacking one article, or group of articles, upon another before packaging
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65B—MACHINES, APPARATUS OR DEVICES FOR, OR METHODS OF, PACKAGING ARTICLES OR MATERIALS; UNPACKING
- B65B25/00—Packaging other articles presenting special problems
- B65B25/14—Packaging paper or like sheets, envelopes, or newspapers, in flat, folded, or rolled form
- B65B25/145—Packaging paper or like sheets, envelopes, or newspapers, in flat, folded, or rolled form packaging folded articles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65H—HANDLING THIN OR FILAMENTARY MATERIAL, e.g. SHEETS, WEBS, CABLES
- B65H31/00—Pile receivers
- B65H31/34—Apparatus for squaring-up piled articles
- B65H31/38—Apparatus for vibrating or knocking the pile during piling
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65H—HANDLING THIN OR FILAMENTARY MATERIAL, e.g. SHEETS, WEBS, CABLES
- B65H2701/00—Handled material; Storage means
- B65H2701/10—Handled articles or webs
- B65H2701/17—Nature of material
- B65H2701/176—Cardboard
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Making Paper Articles (AREA)
- Supplying Of Containers To The Packaging Station (AREA)
- Container Filling Or Packaging Operations (AREA)
- Attitude Control For Articles On Conveyors (AREA)
- Closing Of Containers (AREA)
- Pile Receivers (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Discharge By Other Means (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO754276A NO754276L (fr) | 1970-04-20 | 1975-12-16 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3006970A | 1970-04-20 | 1970-04-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135173B true NO135173B (fr) | 1976-11-15 |
| NO135173C NO135173C (fr) | 1977-02-23 |
Family
ID=21852342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1450/71A NO135173C (fr) | 1970-04-20 | 1971-04-19 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3656271A (fr) |
| JP (1) | JPS5320914B2 (fr) |
| AT (1) | AT327102B (fr) |
| BE (1) | BE765957A (fr) |
| CA (1) | CA948603A (fr) |
| CH (2) | CH544028A (fr) |
| DE (1) | DE2118998A1 (fr) |
| FR (1) | FR2089885A5 (fr) |
| GB (2) | GB1351182A (fr) |
| LU (1) | LU63014A1 (fr) |
| NL (1) | NL7105253A (fr) |
| NO (1) | NO135173C (fr) |
| SE (2) | SE384831B (fr) |
| ZA (1) | ZA712478B (fr) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE789625A (fr) * | 1971-11-12 | 1973-02-01 | Fmc Corp | Procede et appareil pour emballer des articles flexibles |
| US3805482A (en) * | 1971-12-29 | 1974-04-23 | Union Carbide Corp | Packaging machine |
| US3919827A (en) * | 1974-11-26 | 1975-11-18 | Union Carbide Corp | Method and apparatus for packaging large size bags in cartons |
| DE2908943A1 (de) * | 1979-03-07 | 1980-09-11 | Hans Lehmacher | Vorrichtung zum einbringen eines losen flachstapels in einen verpackungskarton |
| DE2939310A1 (de) * | 1979-09-28 | 1981-04-16 | Bielomatik Leuze Gmbh + Co, 7442 Neuffen | Verfahren und vorrichtung tum verpacken von blattstapeln |
| US4472923A (en) * | 1981-08-06 | 1984-09-25 | Mobil Oil Corporation | Carton loader |
| US4751807A (en) * | 1987-04-17 | 1988-06-21 | C. G. Bretting Manufacturing Co. | Automatic transfer system |
| US5375393A (en) * | 1993-04-07 | 1994-12-27 | Automated Solutions, Inc. | Bag folding system |
| IT1282482B1 (it) * | 1995-04-04 | 1998-03-23 | Tecnomeccanica Srl | Metodo per ripiegare a soffietto uno spezzone tubolare di carta-filtro a forma allungata contenente un prodotto da infusione. ivi disposto |
| US6322315B1 (en) | 1999-10-04 | 2001-11-27 | C.G. Bretting Manufacturing Company, Inc. | Web stacker and separator apparatus and method |
| US6254522B1 (en) | 1999-10-05 | 2001-07-03 | C. G. Bretting Manufacturing Co., Inc. | Separator finger apparatus |
| US6832886B2 (en) | 2001-07-27 | 2004-12-21 | C. G. Bretting Manufacturing Co., Inc. | Apparatus and method for stacking sheets discharged from a starwheel assembly |
| US7470102B2 (en) * | 2001-07-27 | 2008-12-30 | C.G. Bretting Manufacturing Co., Inc. | Apparatus and method for insertion of separating means into a forming stack of sheets discharged from a starwheel assembly |
| US6732492B2 (en) * | 2002-07-23 | 2004-05-11 | Potlatch Corporation | Methods of packaging paper products |
| US6912826B2 (en) * | 2002-10-07 | 2005-07-05 | Zoran Momich | Carrier loading cartoner |
| US6877740B2 (en) * | 2003-07-30 | 2005-04-12 | C.G. Bretting Manufacturing Company, Inc. | Starwheel feed apparatus and method |
| US7497064B2 (en) * | 2004-10-01 | 2009-03-03 | Zoran Momich | Vertical cartoner |
| US7073310B1 (en) * | 2004-12-27 | 2006-07-11 | Kimberly-Clark Worldwide, Inc. | Flexible carton loading apparatus |
| JP5948900B2 (ja) | 2012-01-26 | 2016-07-06 | ブラザー工業株式会社 | 記録媒体後処理装置、該記録媒体後処理装置を備えたプリンタユニット、記録媒体後処理方法及び記録媒体後処理プログラム |
| CN105452108B (zh) * | 2013-08-09 | 2017-06-13 | 户谷技研工业株式会社 | 片状产品包装装置 |
| CN108583957A (zh) * | 2018-06-25 | 2018-09-28 | 歆坤智能装备（昆山）有限公司 | 抓手及包装系统 |
| CN112590297B (zh) * | 2020-12-10 | 2022-06-07 | 合肥派腾智能设备科技有限公司 | 一种高效率纸箱开箱机及其工作方法 |
| CN115231075B (zh) * | 2022-08-09 | 2024-07-09 | 天长市天粤塑胶有限公司 | 编织袋加工用切断打包台 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3053024A (en) * | 1961-04-07 | 1962-09-11 | Wexler Joseph | Machine for folding and wrapping paper bundles |
| US3309834A (en) * | 1963-10-04 | 1967-03-21 | Brown Co | Dispensing carton suitable for plastic bags and the like |
| US3481099A (en) * | 1968-09-09 | 1969-12-02 | Colgate Palmolive Co | Packaging apparatus and method |
-
1970
- 1970-04-20 US US30069A patent/US3656271A/en not_active Expired - Lifetime
-
1971
- 1971-04-16 CA CA110,508A patent/CA948603A/en not_active Expired
- 1971-04-19 GB GB5287272A patent/GB1351182A/en not_active Expired
- 1971-04-19 GB GB996671*[A patent/GB1351181A/en not_active Expired
- 1971-04-19 NL NL7105253A patent/NL7105253A/xx unknown
- 1971-04-19 FR FR7113825A patent/FR2089885A5/fr not_active Expired
- 1971-04-19 NO NO1450/71A patent/NO135173C/no unknown
- 1971-04-19 BE BE765957A patent/BE765957A/fr unknown
- 1971-04-19 ZA ZA712478A patent/ZA712478B/xx unknown
- 1971-04-19 SE SE7105053A patent/SE384831B/xx unknown
- 1971-04-19 CH CH814673A patent/CH544028A/fr not_active IP Right Cessation
- 1971-04-19 AT AT332971A patent/AT327102B/de not_active IP Right Cessation
- 1971-04-19 LU LU63014D patent/LU63014A1/xx unknown
- 1971-04-19 CH CH565771A patent/CH542092A/fr not_active IP Right Cessation
- 1971-04-20 DE DE19712118998 patent/DE2118998A1/de active Pending
-
1974
- 1974-09-30 SE SE7412294A patent/SE7412294L/xx unknown
-
1975
- 1975-11-08 JP JP13461075A patent/JPS5320914B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE765957A (fr) | 1971-10-19 |
| ZA712478B (en) | 1972-01-26 |
| SE384831B (sv) | 1976-05-24 |
| JPS5169874A (fr) | 1976-06-16 |
| CH542092A (fr) | 1973-09-30 |
| JPS5320914B2 (fr) | 1978-06-29 |
| SE7412294L (fr) | 1974-09-30 |
| FR2089885A5 (fr) | 1972-01-07 |
| CH544028A (fr) | 1973-12-28 |
| ATA332971A (de) | 1975-03-15 |
| CA948603A (en) | 1974-06-04 |
| AT327102B (de) | 1976-01-12 |
| US3656271A (en) | 1972-04-18 |
| NO135173C (fr) | 1977-02-23 |
| GB1351181A (en) | 1974-04-24 |
| DE2118998A1 (de) | 1971-12-02 |
| NL7105253A (fr) | 1971-10-22 |
| GB1351182A (en) | 1974-04-24 |
| LU63014A1 (fr) | 1972-03-02 |
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