IL33573A - Bis-basic ethers and thioethers of fluorenone,fluorenol and fluorene - Google Patents
Bis-basic ethers and thioethers of fluorenone,fluorenol and fluoreneInfo
- Publication number
- IL33573A IL33573A IL33573A IL3357368A IL33573A IL 33573 A IL33573 A IL 33573A IL 33573 A IL33573 A IL 33573A IL 3357368 A IL3357368 A IL 3357368A IL 33573 A IL33573 A IL 33573A
- Authority
- IL
- Israel
- Prior art keywords
- bis
- fluoren
- compound
- acid addition
- addition salt
- Prior art date
Links
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 title claims description 24
- 150000002170 ethers Chemical class 0.000 title description 16
- 150000003568 thioethers Chemical class 0.000 title description 15
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 title description 9
- AFMVESZOYKHDBJ-UHFFFAOYSA-N fluoren-9-ol Chemical compound C1=CC=C2C(O)C3=CC=CC=C3C2=C1 AFMVESZOYKHDBJ-UHFFFAOYSA-N 0.000 title description 4
- -1 2 -(dimethylamino)ethoxy Chemical group 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom 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
- WECMFRPBWSBCEU-UHFFFAOYSA-N 2,7-bis(2-piperidin-1-ylethoxy)fluoren-9-one Chemical compound C=1C=C2C3=CC=C(OCCN4CCCCC4)C=C3C(=O)C2=CC=1OCCN1CCCCC1 WECMFRPBWSBCEU-UHFFFAOYSA-N 0.000 claims 1
- MGOKYIJIZHLGCV-UHFFFAOYSA-N 2,7-bis(2-pyrrolidin-1-ylethoxy)fluoren-9-one Chemical compound C=1C=C2C3=CC=C(OCCN4CCCC4)C=C3C(=O)C2=CC=1OCCN1CCCC1 MGOKYIJIZHLGCV-UHFFFAOYSA-N 0.000 claims 1
- OHEIWFHEASNQGT-UHFFFAOYSA-N 2,7-bis(3-piperidin-1-ylpropoxy)fluoren-9-one Chemical compound C=1C=C2C3=CC=C(OCCCN4CCCCC4)C=C3C(=O)C2=CC=1OCCCN1CCCCC1 OHEIWFHEASNQGT-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
- 238000000034 method Methods 0.000 description 55
- 239000000203 mixture Substances 0.000 description 55
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
- 239000004480 active ingredient Substances 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 21
- 230000009467 reduction Effects 0.000 description 21
- 238000006722 reduction reaction Methods 0.000 description 21
- 241001465754 Metazoa Species 0.000 description 19
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- 239000002585 base Substances 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 150000008376 fluorenones Chemical class 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 125000002947 alkylene group Chemical group 0.000 description 11
- 230000002829 reductive effect Effects 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 150000003512 tertiary amines Chemical class 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 150000003335 secondary amines Chemical class 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 150000003141 primary amines Chemical class 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000007126 N-alkylation reaction Methods 0.000 description 7
- 238000010531 catalytic reduction reaction Methods 0.000 description 7
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- CWHPQXRTQSNTRR-UHFFFAOYSA-N 2,7-dihydroxyfluoren-9-one Chemical compound C1=C(O)C=C2C(=O)C3=CC(O)=CC=C3C2=C1 CWHPQXRTQSNTRR-UHFFFAOYSA-N 0.000 description 6
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- 229910000564 Raney nickel Inorganic materials 0.000 description 5
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
- 150000002220 fluorenes Chemical class 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 241000700605 Viruses Species 0.000 description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 239000002808 molecular sieve Substances 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 4
- 125000000101 thioether group Chemical group 0.000 description 4
- MPMFCABZENCRHV-UHFFFAOYSA-N tilorone Chemical compound C1=C(OCCN(CC)CC)C=C2C(=O)C3=CC(OCCN(CC)CC)=CC=C3C2=C1 MPMFCABZENCRHV-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 3
- RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001721 carbon Chemical group 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
- 239000008120 corn starch Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 2
- RFGPJHXJKJTNNX-UHFFFAOYSA-N 2-[[7-(2-aminoethoxy)-9h-fluoren-2-yl]oxy]ethanamine Chemical compound NCCOC1=CC=C2C3=CC=C(OCCN)C=C3CC2=C1 RFGPJHXJKJTNNX-UHFFFAOYSA-N 0.000 description 2
- JJOUYGCJCQAYLZ-UHFFFAOYSA-N 2-[[7-(cyanomethoxy)-9H-fluoren-2-yl]oxy]acetonitrile Chemical compound C(#N)COC1=CC=2CC3=CC(=CC=C3C2C=C1)OCC#N JJOUYGCJCQAYLZ-UHFFFAOYSA-N 0.000 description 2
- QGURJVVCERDMJS-UHFFFAOYSA-N 2-[[7-[2-(dimethylamino)ethoxy]-9h-fluoren-2-yl]oxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOC1=CC=C2C3=CC=C(OCCN(C)C)C=C3CC2=C1 QGURJVVCERDMJS-UHFFFAOYSA-N 0.000 description 2
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 229940018557 citraconic acid Drugs 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 150000004658 ketimines 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
- 239000007788 liquid Substances 0.000 description 2
- 239000006193 liquid solution Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000005932 reductive alkylation reaction Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 2
- 239000007892 solid unit dosage form Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
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- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- BSVYJQAWONIOOU-UHFFFAOYSA-N tilorone dihydrochloride Chemical compound Cl.Cl.C1=C(OCCN(CC)CC)C=C2C(=O)C3=CC(OCCN(CC)CC)=CC=C3C2=C1 BSVYJQAWONIOOU-UHFFFAOYSA-N 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 208000007089 vaccinia Diseases 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oncology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Fodder In General (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US78803868A | 1968-12-30 | 1968-12-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
IL33573A true IL33573A (en) | 1973-10-25 |
Family
ID=25143255
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL33573A IL33573A (en) | 1968-12-30 | 1968-12-19 | Bis-basic ethers and thioethers of fluorenone,fluorenol and fluorene |
IL33573A IL33573A0 (en) | 1968-12-30 | 1969-12-19 | Bis-basic ethers and thioethers of fluorenone,fluorenol and fluorene |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL33573A IL33573A0 (en) | 1968-12-30 | 1969-12-19 | Bis-basic ethers and thioethers of fluorenone,fluorenol and fluorene |
Country Status (17)
Country | Link |
---|---|
US (1) | US3592819A (ja) |
JP (2) | JPS4916421B1 (ja) |
BE (1) | BE743755A (ja) |
BR (1) | BR6915322D0 (ja) |
CH (1) | CH524552A (ja) |
DE (1) | DE1964761C3 (ja) |
DK (1) | DK132403C (ja) |
ES (1) | ES374999A1 (ja) |
FR (1) | FR2027383B1 (ja) |
GB (1) | GB1274479A (ja) |
IE (1) | IE33672B1 (ja) |
IL (2) | IL33573A (ja) |
LU (1) | LU60112A1 (ja) |
NL (1) | NL163501C (ja) |
NO (1) | NO129091B (ja) |
PL (1) | PL80457B1 (ja) |
SE (1) | SE360069B (ja) |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3673191A (en) * | 1970-02-18 | 1972-06-27 | Richardson Merrell Inc | Bis-basic ethers and thioethers of dibenzothiophene |
US3946021A (en) * | 1970-07-23 | 1976-03-23 | Richardson-Merrell Inc. | Bis-basic ketones of carbazole |
CA993795A (en) * | 1970-12-10 | 1976-07-27 | Richardson-Merrell (Canada) Ltd. | Antiviral compositions containing bis-basic ethers and thioethers of xanthene and xanthen-9-ones and methods of treating viruses therewith |
US3923991A (en) * | 1972-05-23 | 1975-12-02 | American Home Prod | 1,6-Bis(2-piperidinoethoxy)xanthene-9-one HCl, hydrate in the treatment of inflammation |
AU6081373A (en) * | 1972-09-28 | 1975-03-27 | Searle & Co | 2,7-bis%2-%4-azatricyclo%4.3.1.13,8<undec-4-yl<ethoxy<- fluoren-9-one and congeners |
US3962451A (en) * | 1972-12-21 | 1976-06-08 | Richardson-Merrell Inc. | Carbazole derivatives |
ZA738207B (en) * | 1972-12-21 | 1975-02-26 | Richardson Merrell Inc | Bis-basic ethers of 9-substituted phenanthrene and related 10-oxa and 10-aza derivatives therof |
US3983124A (en) * | 1972-12-21 | 1976-09-28 | Richardson-Merrell Inc. | Fluorene compounds |
US4008240A (en) * | 1972-12-21 | 1977-02-15 | Richardson-Merrell Inc. | Xanthene and thioxanthene derivatives |
US3869496A (en) * | 1972-12-21 | 1975-03-04 | Richardson Merrell Inc | 2,7-bis-basic esters and ethers of 9-benzylidenefluorence |
US4169897A (en) * | 1972-12-21 | 1979-10-02 | Richardson-Merrell Inc. | 2,7-bis-basic ethers of 9-phenanthrol and 9-loweralkoxy phenanthrol |
US4082744A (en) * | 1973-05-08 | 1978-04-04 | Nihon Iyakuhin Kogyo Co., Ltd. | 4-benzazonine derivatives and process for preparation thereof |
US4041165A (en) * | 1973-06-15 | 1977-08-09 | Richardson-Merrell Inc. | Pharmaceutically useful nitrogen containing heterocyclic derivatives |
US4073904A (en) * | 1973-09-05 | 1978-02-14 | Richardson-Merrell, Inc. | Bis-basic ethers of 2,6,- and 2,7-dihydroxy-anthraquinones |
US3892776A (en) * | 1974-03-08 | 1975-07-01 | Richardson Merrell Inc | N-oxides of bis-basic tricyclic ethers |
US3890328A (en) * | 1974-03-08 | 1975-06-17 | Richardson Merrell Inc | N,N-dioxides of bis-basic cyclic ketones |
JPS5160421U (ja) * | 1974-11-05 | 1976-05-12 | ||
JPS5160420U (ja) * | 1974-11-05 | 1976-05-12 | ||
US4053514A (en) * | 1975-07-28 | 1977-10-11 | E. R. Squibb & Sons, Inc. | 2-[Dialkylaminoalkoxyphenyl]-methylene-2,3-dihydro-1H-inden-1-ones and the salts thereof |
CS212669B1 (en) * | 1980-02-04 | 1982-03-26 | Jiri Krepelka | Basic esters of the 7-oxo-7h-benzo/c/fluorene and method of preparation thereof |
DE3424715A1 (de) * | 1984-07-05 | 1986-02-06 | Standard Elektrik Lorenz Ag, 7000 Stuttgart | Aus traegerplatte und schichtschaltung bestehende baugruppe |
US4696936A (en) * | 1984-11-09 | 1987-09-29 | American Cyanamid Company | 3,6-bis (substituted) acridine N-oxides and N,N-dioxides and methods of restoring, stimulating or enhancing the immune system with them |
DE3790062T (ja) * | 1986-02-06 | 1988-01-28 | ||
US6037362A (en) * | 1996-01-10 | 2000-03-14 | Asahi Kasei Kogyo Kabushiki Kaisha | Tricyclic compounds and drug compositions containing the same |
US6004959A (en) * | 1996-05-30 | 1999-12-21 | Hoechst Marion Roussel, Inc. | Alkyloxyamino substituted fluorenones and their use as protein kinase-C inhibitors |
PT906268E (pt) * | 1996-05-30 | 2002-05-31 | Aventis Pharma Inc | Fluorenonas com substituicao alquiloxiamino e sua utilizacao como inibidores da proteina quinase c |
EP1248777A2 (en) * | 2000-01-07 | 2002-10-16 | Warner-Lambert Company | Tricyclic compounds with antiviral activity |
US8748664B2 (en) | 2010-02-24 | 2014-06-10 | Nitto Denko Corporation | Diamine compound and production method thereof |
RU2521595C2 (ru) * | 2011-12-15 | 2014-06-27 | Закрытое акционерное общество "Активный Компонент" | Кристаллическая форма ii тилорона и способ ее получения (варианты) |
RU2509074C2 (ru) * | 2012-04-10 | 2014-03-10 | Закрытое акционерное общество "Активный Компонент" | Кристаллическая форма iv тилорона дигидрохлорида и промышленный способ ее получения (варианты) |
-
1968
- 1968-12-19 IL IL33573A patent/IL33573A/en unknown
- 1968-12-30 US US788038A patent/US3592819A/en not_active Expired - Lifetime
-
1969
- 1969-12-15 IE IE1668/69A patent/IE33672B1/xx unknown
- 1969-12-17 GB GB61592/69A patent/GB1274479A/en not_active Expired
- 1969-12-19 IL IL33573A patent/IL33573A0/xx unknown
- 1969-12-19 PL PL1969137660A patent/PL80457B1/pl unknown
- 1969-12-19 BR BR215322/69A patent/BR6915322D0/pt unknown
- 1969-12-23 SE SE17885/69A patent/SE360069B/xx unknown
- 1969-12-24 BE BE743755D patent/BE743755A/xx not_active IP Right Cessation
- 1969-12-24 DE DE1964761A patent/DE1964761C3/de not_active Expired
- 1969-12-29 NO NO05155/69A patent/NO129091B/no unknown
- 1969-12-29 ES ES374999A patent/ES374999A1/es not_active Expired
- 1969-12-29 LU LU60112D patent/LU60112A1/xx unknown
- 1969-12-29 DK DK687369A patent/DK132403C/da active
- 1969-12-30 JP JP45002096A patent/JPS4916421B1/ja active Pending
- 1969-12-30 NL NL6919612.A patent/NL163501C/xx not_active IP Right Cessation
- 1969-12-30 FR FR6945443A patent/FR2027383B1/fr not_active Expired
- 1969-12-30 CH CH1946969A patent/CH524552A/fr not_active IP Right Cessation
-
1972
- 1972-11-22 JP JP47117657A patent/JPS4917259B1/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
GB1274479A (en) | 1972-05-17 |
IE33672L (en) | 1970-06-30 |
BR6915322D0 (pt) | 1973-04-05 |
NO129091B (ja) | 1974-02-25 |
PL80457B1 (ja) | 1975-08-30 |
NL6919612A (ja) | 1970-07-02 |
DK132403B (da) | 1975-12-01 |
DE1964761B2 (de) | 1980-06-26 |
DE1964761A1 (de) | 1970-07-16 |
US3592819A (en) | 1971-07-13 |
ES374999A1 (es) | 1972-02-16 |
BE743755A (ja) | 1970-06-24 |
JPS4917259B1 (ja) | 1974-04-27 |
SE360069B (ja) | 1973-09-17 |
DE1964761C3 (de) | 1981-04-16 |
NL163501C (nl) | 1980-09-15 |
FR2027383B1 (ja) | 1974-02-01 |
NL163501B (nl) | 1980-04-15 |
JPS4916421B1 (ja) | 1974-04-22 |
IL33573A0 (en) | 1970-02-19 |
DK132403C (da) | 1976-05-10 |
LU60112A1 (ja) | 1970-07-01 |
FR2027383A1 (ja) | 1970-09-25 |
IE33672B1 (en) | 1974-09-18 |
CH524552A (fr) | 1972-06-30 |
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