NO135180B - - Google Patents
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- Publication number
- NO135180B NO135180B NO3704/71A NO370471A NO135180B NO 135180 B NO135180 B NO 135180B NO 3704/71 A NO3704/71 A NO 3704/71A NO 370471 A NO370471 A NO 370471A NO 135180 B NO135180 B NO 135180B
- Authority
- NO
- Norway
- Prior art keywords
- dibenzo
- dihydro
- cyclohepten
- imine
- chloro
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 29
- NYIODHFKZFKMSU-UHFFFAOYSA-N n,n-bis(methylamino)ethanamine Chemical compound CCN(NC)NC NYIODHFKZFKMSU-UHFFFAOYSA-N 0.000 claims description 18
- -1 ethylene, vinylene, oxymethylene Chemical group 0.000 claims description 15
- 150000002466 imines Chemical class 0.000 claims description 14
- BMVWCPGVLSILMU-UHFFFAOYSA-N 5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=CC=C21 BMVWCPGVLSILMU-UHFFFAOYSA-N 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- UARWLAOATPMYKK-UHFFFAOYSA-N 4-chloro-5,6-dihydrodibenzo[2,1-b:3',2'-f][7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2 UARWLAOATPMYKK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- IXNZARLZBMCANF-UHFFFAOYSA-N 2-chloro-5,6-dihydrodibenzo[3,1-[7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC(Cl)=CC=C21 IXNZARLZBMCANF-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- YPLIFKZBNCNJJN-UHFFFAOYSA-N n,n-bis(ethylamino)ethanamine Chemical compound CCNN(CC)NCC YPLIFKZBNCNJJN-UHFFFAOYSA-N 0.000 claims description 6
- 239000002841 Lewis acid Substances 0.000 claims description 5
- 150000007517 lewis acids Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- GJKOOIPYOZMUTN-UHFFFAOYSA-N 2-[(4-chloro-5,6-dihydrodibenzo[2,1-b:3',2'-f][7]annulen-11-ylidene)amino]-n,n-dimethylethanamine Chemical compound C1CC2=C(Cl)C=CC=C2C(=NCCN(C)C)C2=CC=CC=C21 GJKOOIPYOZMUTN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- BNWYIUQZSZZQMO-UHFFFAOYSA-N 2-[(2-chloro-5,6-dihydrodibenzo[3,1-[7]annulen-11-ylidene)amino]-n,n-diethylethanamine Chemical compound C1CC2=CC=C(Cl)C=C2C(=NCCN(CC)CC)C2=CC=CC=C21 BNWYIUQZSZZQMO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- ZWEGWMZBISODMV-UHFFFAOYSA-N 2-[(4-chloro-5,6-dihydrodibenzo[2,1-b:3',2'-f][7]annulen-11-ylidene)amino]-n,n-diethylethanamine Chemical compound C1CC2=C(Cl)C=CC=C2C(=NCCN(CC)CC)C2=CC=CC=C21 ZWEGWMZBISODMV-UHFFFAOYSA-N 0.000 claims 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 49
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
- 239000000155 melt Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- SWVGZFQJXVPIKM-UHFFFAOYSA-N n,n-bis(methylamino)propan-1-amine Chemical compound CCCN(NC)NC SWVGZFQJXVPIKM-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 8
- 235000006408 oxalic acid Nutrition 0.000 description 8
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000012259 ether extract Substances 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000012300 argon atmosphere Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- SNVTZAIYUGUKNI-UHFFFAOYSA-N dibenzo[1,2-a:1',2'-e][7]annulen-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=CC=CC=C21 SNVTZAIYUGUKNI-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000002808 molecular sieve Substances 0.000 description 5
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- NBOTVTKJRBAJLU-UHFFFAOYSA-N 3-(5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-ylideneamino)-n,n-dimethylpropan-1-amine Chemical compound C1CC2=CC=CC=C2C(=NCCCN(C)C)C2=CC=CC=C21 NBOTVTKJRBAJLU-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 230000001430 anti-depressive effect Effects 0.000 description 4
- 239000000935 antidepressant agent Substances 0.000 description 4
- 229940005513 antidepressants Drugs 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 230000000737 periodic effect Effects 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- IJCTUMVTHTWIOG-UHFFFAOYSA-N 2-(5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-ylideneamino)ethanol Chemical compound C1CC2=CC=CC=C2C(=NCCO)C2=CC=CC=C21 IJCTUMVTHTWIOG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
- 230000001078 anti-cholinergic effect Effects 0.000 description 3
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- WUKMXVXFFIHIFW-UHFFFAOYSA-N cyclohept-4-en-1-imine Chemical compound N=C1CCC=CCC1 WUKMXVXFFIHIFW-UHFFFAOYSA-N 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- SJRAWAYUPQULHD-UHFFFAOYSA-N 11-oxo-5,6-dihydrodibenzo[2,1-b:3',1'-f][7]annulene-4-carbonitrile Chemical compound C1CC2=C(C#N)C=CC=C2C(=O)C2=CC=CC=C21 SJRAWAYUPQULHD-UHFFFAOYSA-N 0.000 description 2
- AVFKLLDPNGZKBX-UHFFFAOYSA-N 11-oxo-5,6-dihydrodibenzo[3,1-[7]annulene-2-carbonitrile Chemical compound C1CC2=CC=C(C#N)C=C2C(=O)C2=CC=CC=C21 AVFKLLDPNGZKBX-UHFFFAOYSA-N 0.000 description 2
- WYNVGOWIBKNNRK-UHFFFAOYSA-N 2,4-dichloro-5,6-dihydrodibenzo[2,1-b:4',1'-f][7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC(Cl)=CC(Cl)=C21 WYNVGOWIBKNNRK-UHFFFAOYSA-N 0.000 description 2
- MQXAEYLTGZJZNP-UHFFFAOYSA-N 2-(5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-ylideneamino)ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCN=C1C2=CC=CC=C2CCC2=CC=CC=C21 MQXAEYLTGZJZNP-UHFFFAOYSA-N 0.000 description 2
- SYGVEAINKHSXQM-UHFFFAOYSA-N 2-[(2,4-dichloro-5,6-dihydrodibenzo[2,1-b:4',1'-f][7]annulen-11-ylidene)amino]-n,n-dimethylethanamine Chemical compound C1CC2=C(Cl)C=C(Cl)C=C2C(=NCCN(C)C)C2=CC=CC=C21 SYGVEAINKHSXQM-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 229960005333 tetrabenazine Drugs 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- BFIMWLBHXWBHBQ-UHFFFAOYSA-N 1-methyl-2-propylhydrazine Chemical compound CCCNNC BFIMWLBHXWBHBQ-UHFFFAOYSA-N 0.000 description 1
- RRQHLOZQFPWDCA-UHFFFAOYSA-N 1-n,1-n-dimethylpropane-1,2-diamine Chemical compound CC(N)CN(C)C RRQHLOZQFPWDCA-UHFFFAOYSA-N 0.000 description 1
- XKZKTBQUPKINBS-UHFFFAOYSA-N 11-[3-(dimethylamino)propylimino]-5,6-dihydrodibenzo[2,1-b:3',1'-f][7]annulene-4-carbonitrile Chemical compound C1CC2=C(C#N)C=CC=C2C(=NCCCN(C)C)C2=CC=CC=C21 XKZKTBQUPKINBS-UHFFFAOYSA-N 0.000 description 1
- WLMACKDAAQMPOY-UHFFFAOYSA-N 2-(5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-ylideneamino)-n,n-dimethylethanamine Chemical compound C1CC2=CC=CC=C2C(=NCCN(C)C)C2=CC=CC=C21 WLMACKDAAQMPOY-UHFFFAOYSA-N 0.000 description 1
- RQTREMNRLMOSTE-UHFFFAOYSA-N 2-(5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-ylideneamino)ethanamine Chemical compound C1CC2=CC=CC=C2C(=NCCN)C2=CC=CC=C21 RQTREMNRLMOSTE-UHFFFAOYSA-N 0.000 description 1
- AUEARLNWWBYZQC-UHFFFAOYSA-N 2-(dibenzo[1,2-a:1',2'-e][7]annulen-11-ylideneamino)-n,n-diethylethanamine Chemical compound C1=CC2=CC=CC=C2C(=NCCN(CC)CC)C2=CC=CC=C21 AUEARLNWWBYZQC-UHFFFAOYSA-N 0.000 description 1
- XMWUMXZFPJNLQO-UHFFFAOYSA-N 2-(dibenzo[1,2-a:1',2'-e][7]annulen-11-ylideneamino)-n,n-dimethylethanamine Chemical compound C1=CC2=CC=CC=C2C(=NCCN(C)C)C2=CC=CC=C21 XMWUMXZFPJNLQO-UHFFFAOYSA-N 0.000 description 1
- BGCQURJQCRIOFH-UHFFFAOYSA-N 2-[(2-chloro-5,6-dihydrodibenzo[3,1-[7]annulen-11-ylidene)amino]-n,n-dimethylethanamine Chemical compound C1CC2=CC=C(Cl)C=C2C(=NCCN(C)C)C2=CC=CC=C21 BGCQURJQCRIOFH-UHFFFAOYSA-N 0.000 description 1
- QGHMFIZYXLHANB-UHFFFAOYSA-N 2-[(2-chloro-5,6-dihydrodibenzo[3,1-[7]annulen-11-ylidene)amino]ethanamine Chemical compound C1CC2=CC=C(Cl)C=C2C(=NCCN)C2=CC=CC=C21 QGHMFIZYXLHANB-UHFFFAOYSA-N 0.000 description 1
- WNMYNNUOQAMCPS-UHFFFAOYSA-N 2-[(2-chlorodibenzo[1,3-e:1',2'-f][7]annulen-11-ylidene)amino]-n,n-dimethylethanamine Chemical compound C1=CC2=CC=C(Cl)C=C2C(=NCCN(C)C)C2=CC=CC=C21 WNMYNNUOQAMCPS-UHFFFAOYSA-N 0.000 description 1
- BSQWSGBVHUBVRE-UHFFFAOYSA-N 2-[(4-bromo-5,6-dihydrodibenzo[2,1-b:3',2'-f][7]annulen-11-ylidene)amino]-n,n-dimethylethanamine Chemical compound C1CC2=C(Br)C=CC=C2C(=NCCN(C)C)C2=CC=CC=C21 BSQWSGBVHUBVRE-UHFFFAOYSA-N 0.000 description 1
- QBXSOWYAYREWCZ-UHFFFAOYSA-N 2-[(4-chloro-5,6-dihydrodibenzo[2,1-b:3',2'-f][7]annulen-11-ylidene)amino]-n-methylethanamine Chemical compound C1CC2=C(Cl)C=CC=C2C(=NCCNC)C2=CC=CC=C21 QBXSOWYAYREWCZ-UHFFFAOYSA-N 0.000 description 1
- IPMSEHLVXZZGEM-UHFFFAOYSA-N 2-[(4-fluoro-5,6-dihydrodibenzo[2,1-b:3',2'-f][7]annulen-11-ylidene)amino]-n,n-dimethylethanamine Chemical compound C1CC2=C(F)C=CC=C2C(=NCCN(C)C)C2=CC=CC=C21 IPMSEHLVXZZGEM-UHFFFAOYSA-N 0.000 description 1
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- KAXICSUBAQRCGJ-UHFFFAOYSA-N 3-[(2-chloro-5,6-dihydrodibenzo[3,1-[7]annulen-11-ylidene)amino]-n,n-dimethylpropan-1-amine Chemical compound C1CC2=CC=C(Cl)C=C2C(=NCCCN(C)C)C2=CC=CC=C21 KAXICSUBAQRCGJ-UHFFFAOYSA-N 0.000 description 1
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- IKUNSMJUUWYQEC-UHFFFAOYSA-N 4-chlorodibenzo[1,2-a:3',2'-e][7]annulen-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2 IKUNSMJUUWYQEC-UHFFFAOYSA-N 0.000 description 1
- JGJDEWXZEIHBNW-UHFFFAOYSA-N 6h-benzo[c][1]benzothiepin-11-one Chemical compound C1SC2=CC=CC=C2C(=O)C2=CC=CC=C21 JGJDEWXZEIHBNW-UHFFFAOYSA-N 0.000 description 1
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- 241000699670 Mus sp. Species 0.000 description 1
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- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000947853 Vibrionales Species 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
- 229960000836 amitriptyline Drugs 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 230000001022 anti-muscarinic effect Effects 0.000 description 1
- 230000000648 anti-parkinson Effects 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- OEYOHULQRFXULB-UHFFFAOYSA-N arsenic trichloride Chemical compound Cl[As](Cl)Cl OEYOHULQRFXULB-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 208000030499 combat disease Diseases 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- XHRNQDMNINGCES-UHFFFAOYSA-N cyclohept-4-en-1-one Chemical compound O=C1CCC=CCC1 XHRNQDMNINGCES-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- IQDXNHZDRQHKEF-UHFFFAOYSA-N dialuminum;dicalcium;dioxido(oxo)silane Chemical compound [Al+3].[Al+3].[Ca+2].[Ca+2].[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O IQDXNHZDRQHKEF-UHFFFAOYSA-N 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
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- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000013401 experimental design Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 201000003004 ptosis Diseases 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 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
- IEXRMSFAVATTJX-UHFFFAOYSA-N tetrachlorogermane Chemical compound Cl[Ge](Cl)(Cl)Cl IEXRMSFAVATTJX-UHFFFAOYSA-N 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/34—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups polycyclic
- C07C65/36—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups polycyclic containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D313/12—[b,e]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D337/12—[b,e]-condensed
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1497270A CH541545A (de) | 1970-10-09 | 1970-10-09 | Verfahren zur Herstellung von tricyclischen Iminen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135180B true NO135180B (hu) | 1976-11-15 |
| NO135180C NO135180C (hu) | 1977-02-23 |
Family
ID=4405292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3704/71A NO135180C (hu) | 1970-10-09 | 1971-10-08 |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US3803234A (hu) |
| KR (1) | KR780000028B1 (hu) |
| AR (1) | AR194102A1 (hu) |
| AT (2) | AT313252B (hu) |
| AU (1) | AU458443B2 (hu) |
| BE (1) | BE773649A (hu) |
| BG (2) | BG20559A3 (hu) |
| BR (1) | BR7106595D0 (hu) |
| CA (1) | CA967150A (hu) |
| CH (1) | CH541545A (hu) |
| CS (1) | CS179960B2 (hu) |
| DE (1) | DE2150079A1 (hu) |
| DK (1) | DK138641B (hu) |
| ES (2) | ES395844A1 (hu) |
| FI (1) | FI54100C (hu) |
| FR (1) | FR2110323B1 (hu) |
| GB (1) | GB1334967A (hu) |
| HU (1) | HU162983B (hu) |
| IE (1) | IE35691B1 (hu) |
| IL (1) | IL37705A (hu) |
| NL (1) | NL7113295A (hu) |
| NO (1) | NO135180C (hu) |
| PH (1) | PH9973A (hu) |
| PL (1) | PL83435B1 (hu) |
| RO (1) | RO61541A (hu) |
| SE (1) | SE374912B (hu) |
| SU (2) | SU495830A3 (hu) |
| ZA (1) | ZA716071B (hu) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4003915A (en) * | 1970-10-09 | 1977-01-18 | Hoffmann-La Roche Inc. | Tricyclic imines |
| US3954865A (en) * | 1972-04-27 | 1976-05-04 | E. I. Du Pont De Nemours And Company | N-cycloalkyl substituted-10,11-dihydro 5H-dibenzo[a,d] cyclohepten-5-imines |
| US3901945A (en) * | 1972-09-28 | 1975-08-26 | Du Pont | 1,1a,6,10b-tetrahydrodibenzo (a,e) cyclopropa (c) cyclohepten-6-imines |
| US3985895A (en) * | 1974-03-20 | 1976-10-12 | Hoffmann-La Roche Inc. | N,N-diethyl-N'-{dibenzo[b,e]thiepin-11(6H)-ylidene}-1,3-propanediamine and derivatives thereof |
| US4035509A (en) * | 1974-04-22 | 1977-07-12 | Syntex (U.S.A.) Inc. | Methods and compositions for the use of 2-carboxy-5-oxo-5H-dibenzo[a,d]cycloheptenes, salts and esters thereof |
| US4020094A (en) * | 1974-04-22 | 1977-04-26 | Syntex (U.S.A.) Inc. | 2-Substituted-5-oxo-5H-dibenzo[a,d]cycloheptenes, the salts and esters thereof, having pharmaceutical activity |
| US4041173A (en) * | 1975-10-06 | 1977-08-09 | Syntex (U.S.A.) Inc. | 2-Carboxy-(7-,8- and 9-substituted)-5-oxo-5H-dibenzo (a,d) cycloheptenes and the corresponding 10,11-dihydro compounds |
| US4795822A (en) * | 1984-05-23 | 1989-01-03 | Syntex (U.S.A.) Inc. | Nortriptyline conjugates to antigenic proteins and enzymes |
| WO1996040664A2 (en) * | 1995-06-07 | 1996-12-19 | Dade Chemistry Systems Inc. | Preparation of immunogens and other conjugates of drugs |
| HRP970649B1 (en) * | 1997-12-01 | 2004-12-31 | Belupo Lijekovi I Kozmetika D | Dibenzosuberone derivatives and processes for their preparation |
-
1970
- 1970-10-09 CH CH1497270A patent/CH541545A/de not_active IP Right Cessation
-
1971
- 1971-09-10 ZA ZA716071A patent/ZA716071B/xx unknown
- 1971-09-13 IL IL37705A patent/IL37705A/xx unknown
- 1971-09-13 AU AU33403/71A patent/AU458443B2/en not_active Expired
- 1971-09-16 PH PH12843A patent/PH9973A/en unknown
- 1971-09-22 FI FI2650/71A patent/FI54100C/fi active
- 1971-09-24 BG BG20940A patent/BG20559A3/xx unknown
- 1971-09-24 BG BG18627A patent/BG20775A3/xx unknown
- 1971-09-28 NL NL7113295A patent/NL7113295A/xx unknown
- 1971-09-29 US US00184901A patent/US3803234A/en not_active Expired - Lifetime
- 1971-10-04 IE IE1243/71A patent/IE35691B1/xx unknown
- 1971-10-05 BR BR006595/71A patent/BR7106595D0/pt unknown
- 1971-10-06 SE SE7112643A patent/SE374912B/xx unknown
- 1971-10-07 CS CS7100007092A patent/CS179960B2/cs unknown
- 1971-10-07 DE DE19712150079 patent/DE2150079A1/de active Pending
- 1971-10-07 GB GB4675171A patent/GB1334967A/en not_active Expired
- 1971-10-07 KR KR7301448A patent/KR780000028B1/ko active
- 1971-10-08 HU HUHO1425A patent/HU162983B/hu unknown
- 1971-10-08 AT AT1098072A patent/AT313252B/de not_active IP Right Cessation
- 1971-10-08 SU SU1704970A patent/SU495830A3/ru active
- 1971-10-08 RO RO68410A patent/RO61541A/ro unknown
- 1971-10-08 BE BE773649A patent/BE773649A/xx unknown
- 1971-10-08 NO NO3704/71A patent/NO135180C/no unknown
- 1971-10-08 FR FR7136264A patent/FR2110323B1/fr not_active Expired
- 1971-10-08 ES ES395844A patent/ES395844A1/es not_active Expired
- 1971-10-08 CA CA124,752A patent/CA967150A/en not_active Expired
- 1971-10-08 DK DK491271AA patent/DK138641B/da unknown
- 1971-10-08 AT AT871371A patent/AT312575B/de active
- 1971-10-09 PL PL1971150975A patent/PL83435B1/pl unknown
-
1972
- 1972-05-08 AR AR241872A patent/AR194102A1/es active
-
1973
- 1973-05-25 SU SU1923838A patent/SU519124A3/ru active
- 1973-11-02 ES ES420179A patent/ES420179A1/es not_active Expired
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