CS273314B2 - Method of polycyclic aromatic alkanol derivatives preparation - Google Patents
Method of polycyclic aromatic alkanol derivatives preparation Download PDFInfo
- Publication number
- CS273314B2 CS273314B2 CS364584A CS364584A CS273314B2 CS 273314 B2 CS273314 B2 CS 273314B2 CS 364584 A CS364584 A CS 364584A CS 364584 A CS364584 A CS 364584A CS 273314 B2 CS273314 B2 CS 273314B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- methyl
- mixture
- amino
- grams
- nitro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 56
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 98
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 77
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 54
- -1 hydroxy, methyl Chemical group 0.000 claims abstract description 44
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 105
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 84
- 239000000243 solution Substances 0.000 claims description 70
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 68
- 229910052799 carbon Inorganic materials 0.000 claims description 54
- 239000002904 solvent Substances 0.000 claims description 51
- 238000000921 elemental analysis Methods 0.000 claims description 48
- 239000000047 product Substances 0.000 claims description 40
- 238000002844 melting Methods 0.000 claims description 38
- 230000008018 melting Effects 0.000 claims description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 32
- 239000000460 chlorine Substances 0.000 claims description 32
- 239000007787 solid Substances 0.000 claims description 31
- 239000011541 reaction mixture Substances 0.000 claims description 29
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- 235000019439 ethyl acetate Nutrition 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 238000000746 purification Methods 0.000 claims description 13
- 238000001914 filtration Methods 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- 239000000706 filtrate Substances 0.000 claims description 10
- 239000007810 chemical reaction solvent Substances 0.000 claims description 9
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 8
- 229960000583 acetic acid Drugs 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 239000012362 glacial acetic acid Substances 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 5
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 5
- 239000006188 syrup Substances 0.000 claims description 5
- 235000020357 syrup Nutrition 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 239000001569 carbon dioxide Substances 0.000 claims description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 238000003818 flash chromatography Methods 0.000 claims description 3
- 230000022244 formylation Effects 0.000 claims description 3
- 238000006170 formylation reaction Methods 0.000 claims description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 3
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 2
- 244000309464 bull Species 0.000 claims description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- 239000002027 dichloromethane extract Substances 0.000 claims description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 claims description 2
- KREJIEGRPQSQAG-UHFFFAOYSA-N 4-ethylfluoranthene-3-carbaldehyde Chemical compound C12=CC=CC=C2C2=CC=C(C=O)C3=C2C1=CC=C3CC KREJIEGRPQSQAG-UHFFFAOYSA-N 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 3
- JXUOLJXLPIIRTP-UHFFFAOYSA-N 3-ethylfluoranthene Chemical compound C12=CC=CC=C2C2=CC=CC3=C2C1=CC=C3CC JXUOLJXLPIIRTP-UHFFFAOYSA-N 0.000 claims 2
- VFXDNQYXLCNZGA-UHFFFAOYSA-N 3-methyl-3-nitropentane-2,4-diol Chemical compound CC(O)C(C)(C(C)O)[N+]([O-])=O VFXDNQYXLCNZGA-UHFFFAOYSA-N 0.000 claims 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (1R)-1,3-butanediol Natural products CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 1
- PCNWBUOSTLGPMI-UHFFFAOYSA-N 2-nitro-1-propanol Chemical compound OCC(C)[N+]([O-])=O PCNWBUOSTLGPMI-UHFFFAOYSA-N 0.000 claims 1
- KFSOKSKYVDCQOY-UHFFFAOYSA-N 3-amino-3-methylpentane-2,4-diol Chemical compound CC(O)C(C)(N)C(C)O KFSOKSKYVDCQOY-UHFFFAOYSA-N 0.000 claims 1
- AHCOSHUPTJVUDA-UHFFFAOYSA-N 3-ethylfluoranthene-7-carbaldehyde Chemical compound C12=CC=CC(C=O)=C2C2=CC=CC3=C2C1=CC=C3CC AHCOSHUPTJVUDA-UHFFFAOYSA-N 0.000 claims 1
- OJVOGABFNZDOOZ-UHFFFAOYSA-N 3-nitrobutan-2-ol Chemical compound CC(O)C(C)[N+]([O-])=O OJVOGABFNZDOOZ-UHFFFAOYSA-N 0.000 claims 1
- FBUPBJQUGLBFFY-UHFFFAOYSA-N 4-ethylfluoranthene-7-carbaldehyde Chemical compound C1=CC=C(C=O)C2=C1C1=CC=CC3=C1C2=CC=C3CC FBUPBJQUGLBFFY-UHFFFAOYSA-N 0.000 claims 1
- MMKZTXUXSPHNRG-UHFFFAOYSA-N 4-ethylfluoranthene-8-carbaldehyde Chemical compound C12=CC(C=O)=CC=C2C2=CC=CC3=C2C1=CC=C3CC MMKZTXUXSPHNRG-UHFFFAOYSA-N 0.000 claims 1
- 239000012267 brine Substances 0.000 claims 1
- 230000000704 physical effect Effects 0.000 claims 1
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 claims 1
- 239000012264 purified product Substances 0.000 claims 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims 1
- 239000003039 volatile agent Substances 0.000 claims 1
- 238000010626 work up procedure Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 33
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 20
- 150000003839 salts Chemical class 0.000 abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 18
- 125000001424 substituent group Chemical group 0.000 abstract description 17
- 150000002148 esters Chemical class 0.000 abstract description 14
- 125000000217 alkyl group Chemical group 0.000 abstract description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 10
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract description 10
- 230000000259 anti-tumor effect Effects 0.000 abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 abstract description 7
- 150000002170 ethers Chemical class 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 5
- 230000003115 biocidal effect Effects 0.000 abstract description 4
- 125000005843 halogen group Chemical group 0.000 abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 3
- 125000002837 carbocyclic group Chemical group 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 125000005842 heteroatom Chemical group 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 22
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- 206010028980 Neoplasm Diseases 0.000 description 16
- 239000003921 oil Substances 0.000 description 14
- 239000003480 eluent Substances 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 239000010410 layer Substances 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- SHYBXXMECBHHFH-UHFFFAOYSA-N 10-chloroanthracene-9-carbaldehyde Chemical compound C1=CC=C2C(Cl)=C(C=CC=C3)C3=C(C=O)C2=C1 SHYBXXMECBHHFH-UHFFFAOYSA-N 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 6
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 201000011510 cancer Diseases 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000013058 crude material Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- CCFAKBRKTKVJPO-UHFFFAOYSA-N 1-anthroic acid Chemical compound C1=CC=C2C=C3C(C(=O)O)=CC=CC3=CC2=C1 CCFAKBRKTKVJPO-UHFFFAOYSA-N 0.000 description 4
- SIEYYGAWDCFHPO-UHFFFAOYSA-N 10-methylsulfanylanthracene-9-carbaldehyde Chemical compound C1=CC=C2C(SC)=C(C=CC=C3)C3=C(C=O)C2=C1 SIEYYGAWDCFHPO-UHFFFAOYSA-N 0.000 description 4
- DDMHWNHZNBNNAN-UHFFFAOYSA-N 4-chloroanthracene-9-carbaldehyde Chemical compound C1=CC=C2C=C3C(Cl)=CC=CC3=C(C=O)C2=C1 DDMHWNHZNBNNAN-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 210000004881 tumor cell Anatomy 0.000 description 4
- LGZWQUKBPLPMLI-UHFFFAOYSA-N (10-bromoanthracen-1-yl)methanol Chemical compound C1=CC=C2C=C3C(CO)=CC=CC3=C(Br)C2=C1 LGZWQUKBPLPMLI-UHFFFAOYSA-N 0.000 description 3
- NCYGRBUUKZQQSE-UHFFFAOYSA-N (10-chloroanthracen-1-yl)methanol Chemical compound C1=CC=C2C=C3C(CO)=CC=CC3=C(Cl)C2=C1 NCYGRBUUKZQQSE-UHFFFAOYSA-N 0.000 description 3
- FXKASOSOVAVXTA-UHFFFAOYSA-N 2-(2-iodoethoxy)oxane Chemical compound ICCOC1CCCCO1 FXKASOSOVAVXTA-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- YMGMUMVXYIDTGO-UHFFFAOYSA-N 3-chloroanthracene-9-carbaldehyde Chemical compound C1=CC=CC2=CC3=CC(Cl)=CC=C3C(C=O)=C21 YMGMUMVXYIDTGO-UHFFFAOYSA-N 0.000 description 3
- RSHAKWUMVHQORJ-UHFFFAOYSA-N 3-nitropentane-2,4-diol Chemical compound CC(O)C(C(C)O)[N+]([O-])=O RSHAKWUMVHQORJ-UHFFFAOYSA-N 0.000 description 3
- SAGGALJEKVRKJT-UHFFFAOYSA-N 4,10-dichloroanthracene-9-carbaldehyde Chemical compound C1=CC=C2C(Cl)=C3C(Cl)=CC=CC3=C(C=O)C2=C1 SAGGALJEKVRKJT-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- XCCCHWWMLSAIOH-UHFFFAOYSA-N anthracen-1-ylmethanol Chemical compound C1=CC=C2C=C3C(CO)=CC=CC3=CC2=C1 XCCCHWWMLSAIOH-UHFFFAOYSA-N 0.000 description 3
- XJDFBLQCLSBCGQ-UHFFFAOYSA-N anthracene-1-carbaldehyde Chemical compound C1=CC=C2C=C3C(C=O)=CC=CC3=CC2=C1 XJDFBLQCLSBCGQ-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 3
- 229910010277 boron hydride Inorganic materials 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 210000004027 cell Anatomy 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
- 239000012230 colorless oil Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- GPJKGQJJBMLUHM-UHFFFAOYSA-N ethyl 2-(benzylideneamino)-2-methyl-4-(oxan-2-yloxy)butanoate Chemical compound C=1C=CC=CC=1C=NC(C)(C(=O)OCC)CCOC1CCCCO1 GPJKGQJJBMLUHM-UHFFFAOYSA-N 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000004262 preparative liquid chromatography Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
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- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
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- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
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- 150000007523 nucleic acids Chemical class 0.000 description 1
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- 229940055726 pantothenic acid Drugs 0.000 description 1
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- 239000011713 pantothenic acid Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
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- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 201000009410 rhabdomyosarcoma Diseases 0.000 description 1
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- 239000002002 slurry Substances 0.000 description 1
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000007944 thiolates Chemical class 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- NXDGVEYXRSKONY-UHFFFAOYSA-N triphenylene-2-carbaldehyde Chemical compound C1=CC=C2C3=CC(C=O)=CC=C3C3=CC=CC=C3C2=C1 NXDGVEYXRSKONY-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/20—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated the carbon skeleton being saturated and containing rings
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
- C07C205/14—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to acyclic carbon atoms
- C07C205/15—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to acyclic carbon atoms of a saturated carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/10—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with one amino group and at least two hydroxy groups bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/42—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/48—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
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- 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
- C07C323/31—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 atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/32—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 atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/62—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings
- C07D263/64—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems having two or more ring systems containing condensed 1,3-oxazole rings linked in positions 2 and 2' by chains containing six-membered aromatic rings or ring systems containing such rings
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- 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
- C07D295/12—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 or doubly bound nitrogen atoms
- C07D295/135—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings 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
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- 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
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
-
- 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
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
-
- 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
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
-
- 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
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
-
- 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
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/48—Chrysenes; Hydrogenated chrysenes
-
- 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
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/50—Pyrenes; Hydrogenated pyrenes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CS108789A CS273347B2 (en) | 1983-05-17 | 1989-02-20 | Method of polycyclic aromatic alkanol derivatives preparation |
CS108889A CS273348B2 (en) | 1983-05-17 | 1989-02-20 | Method of polycyclic aromatic alkanol derivatives preparation |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB838313571A GB8313571D0 (en) | 1983-05-17 | 1983-05-17 | Chemical compounds |
APAP/P/1984/000003A AP1A (en) | 1983-05-17 | 1984-07-16 | Polycyclic aromatic compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
CS364584A2 CS364584A2 (en) | 1990-08-14 |
CS273314B2 true CS273314B2 (en) | 1991-03-12 |
Family
ID=39791481
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CS364584A CS273314B2 (en) | 1983-05-17 | 1984-05-16 | Method of polycyclic aromatic alkanol derivatives preparation |
Country Status (30)
Country | Link |
---|---|
US (6) | US4530800A (en]) |
EP (2) | EP0125702B1 (en]) |
JP (3) | JPS59225149A (en]) |
KR (1) | KR910000854B1 (en]) |
AP (1) | AP1A (en]) |
AU (2) | AU572509B2 (en]) |
CA (1) | CA1222750A (en]) |
CS (1) | CS273314B2 (en]) |
CY (1) | CY1486A (en]) |
DD (1) | DD223439A5 (en]) |
DE (2) | DE3473141D1 (en]) |
DK (1) | DK242284A (en]) |
EG (1) | EG17595A (en]) |
ES (3) | ES8603376A1 (en]) |
FI (1) | FI85263C (en]) |
GB (2) | GB8313571D0 (en]) |
GR (1) | GR82278B (en]) |
HK (1) | HK45089A (en]) |
HU (1) | HU197875B (en]) |
IE (1) | IE58416B1 (en]) |
IL (1) | IL71851A (en]) |
MC (1) | MC1595A1 (en]) |
NO (1) | NO157416C (en]) |
NZ (1) | NZ208168A (en]) |
PH (1) | PH22265A (en]) |
PL (3) | PL145420B1 (en]) |
PT (1) | PT78586A (en]) |
SG (1) | SG22389G (en]) |
SU (3) | SU1535377A3 (en]) |
ZA (1) | ZA843708B (en]) |
Families Citing this family (51)
Publication number | Priority date | Publication date | Assignee | Title |
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US4803221A (en) * | 1977-03-15 | 1989-02-07 | Burroughs Wellcome Co. | Anthracene derivatives |
GB8313571D0 (en) * | 1983-05-17 | 1983-06-22 | Wellcome Found | Chemical compounds |
US4719046A (en) * | 1983-05-17 | 1988-01-12 | Burroughs Wellcome Co. | Crysene derivatives |
US4719055A (en) * | 1983-05-17 | 1988-01-12 | Burroughs Wellcome Co. | Phenanthrene derivatives |
US4810727A (en) * | 1983-05-17 | 1989-03-07 | Burroughs Wellcome Co. | Chrysene compound |
US4808632A (en) * | 1983-05-17 | 1989-02-28 | Burroughs Wellcome Co. | Fluoranthene derivatives |
US4808625A (en) * | 1983-05-17 | 1989-02-28 | Burroughs Wellcome Co. | Phenanthrene derivatives |
US4803226A (en) * | 1983-05-17 | 1989-02-07 | Burroughs Wellcome Co. | Anthracene derivatives |
US4719048A (en) * | 1983-05-17 | 1988-01-12 | Burroughs Wellcome Co. | Crysene compound |
US4829090A (en) * | 1983-05-17 | 1989-05-09 | Burroughs Wellcome Co. | Chrysene derivatives |
US4803222A (en) * | 1983-05-17 | 1989-02-07 | Burroughs Wellcome Co. | Fluoranthene derivatives |
US4717729A (en) * | 1983-05-31 | 1988-01-05 | Burroughs Wellcome Co. | Triphenylene derivatives |
ES8702905A1 (es) * | 1984-11-15 | 1987-01-16 | Wellcome Found | Un procedimiento para preparar derivados de alcanoles hete- ropoliciclicos |
GB8428932D0 (en) * | 1984-11-15 | 1984-12-27 | Wellcome Found | Polycyclic biocidal compounds |
GB8428930D0 (en) * | 1984-11-15 | 1984-12-27 | Wellcome Found | Polycyclic biocidal compounds |
GB8428931D0 (en) * | 1984-11-15 | 1984-12-27 | Wellcome Found | Polycyclic biocidal compounds |
US4818443A (en) * | 1985-11-22 | 1989-04-04 | Burroughs Wellcome Co. | Carbocyclic derivatives |
US4810823A (en) * | 1985-11-22 | 1989-03-07 | Burroughs Wellcome Co. | Carbocyclic derivatives |
US4791233A (en) * | 1985-11-22 | 1988-12-13 | Burroughs Wellcome Co. | Carbocyclic derivatives |
US4808753A (en) * | 1985-11-22 | 1989-02-28 | Burroughs Wellcome Co. | Carbocyclic derivatives |
US4827034A (en) * | 1985-11-22 | 1989-05-02 | Burroughs Wellcome Co. | Carbocyclic derivatives |
US4791231A (en) * | 1985-11-22 | 1988-12-13 | Burroughs Wellcome Co. | Carbocyclic derivatives |
US4814502A (en) * | 1985-11-22 | 1989-03-21 | Burroughs Wellcome Co. | Carbocyclic derivatives |
US5008286A (en) * | 1985-11-22 | 1991-04-16 | Burroughs Wellcome Co. | Certain substituted naphthofurans with anti-tumor properties |
US4882358A (en) * | 1985-11-22 | 1989-11-21 | Burroughs Wellcome Co. | Carbocyclic derivatives |
US4791232A (en) * | 1985-11-22 | 1988-12-13 | Burroughs Wellcome Co. | Carbocyclic derivatives |
US5435667A (en) * | 1986-02-20 | 1995-07-25 | Slickbar Products Corp. | Protection of piles |
JP2735609B2 (ja) * | 1989-03-31 | 1998-04-02 | 協和醗酵工業株式会社 | Ucn―1028d誘導体 |
US5416244A (en) * | 1991-09-30 | 1995-05-16 | Ohmeda Pharmaceutical Products Division Inc. | Preparation of isoflurane |
JPH06329679A (ja) * | 1993-01-20 | 1994-11-29 | Nissan Chem Ind Ltd | 光学活性β−アミノアルコキシボラン錯体 |
WO1998039287A1 (en) * | 1997-03-05 | 1998-09-11 | Trimeris, Inc. | Benzanthrone compounds and antiviral uses thereof |
FR2775286B1 (fr) * | 1998-02-20 | 2001-09-07 | Centre Nat Rech Scient | Derives du triphenylene contre le sida |
US6015811A (en) * | 1998-10-27 | 2000-01-18 | Board Of Regents, The University Of Texas System | Antitumor Chrysene derivatives |
KR100722890B1 (ko) * | 1999-12-30 | 2007-05-30 | 킴벌리-클라크 월드와이드, 인크. | 항바이러스성 로션 티슈, 및 이의 제조 방법 및 사용 방법 |
US6372785B1 (en) * | 2000-05-04 | 2002-04-16 | Keith Chan, President Globoasia, Llc | Synthesis of 1,8-dichloro-anthracene analogues and pharmaceutical compositions based thereon |
US20050107430A1 (en) * | 2003-10-29 | 2005-05-19 | Banik Bimal K. | Antimicrobial and antiviral compounds |
WO2005089094A2 (en) * | 2003-11-21 | 2005-09-29 | The Board Of Regents Of The University And Community College System Of Nevada | Materials and methods for the preparation of anisotropically-ordered solids |
WO2005119223A1 (en) * | 2004-04-14 | 2005-12-15 | Bioprocessors Corp. | Compositions of matter useful as ph indicators and related methods |
KR100872692B1 (ko) * | 2006-03-06 | 2008-12-10 | 주식회사 엘지화학 | 신규한 안트라센 유도체 및 이를 이용한 유기 전자 소자 |
RU2349311C1 (ru) * | 2007-08-02 | 2009-03-20 | Михаил Владимирович Кутушов | Применение дериватов нафталина в качестве средств для лечения онкологических заболеваний |
US9090638B2 (en) | 2008-04-17 | 2015-07-28 | Thomas Daly | Biological buffers with wide buffering ranges |
US8334402B2 (en) * | 2008-04-17 | 2012-12-18 | Thomas Daly | Biological buffers with wide buffering ranges |
US7939659B2 (en) * | 2008-04-17 | 2011-05-10 | Thomas Daly | Biological buffers with wide buffering ranges |
US8034951B2 (en) | 2008-04-17 | 2011-10-11 | Thomas Daly | Biological buffers with wide buffering ranges |
US9447310B2 (en) | 2008-04-17 | 2016-09-20 | Thomas P. Daly | Biological buffers with wide buffering ranges |
US8822728B2 (en) | 2008-04-17 | 2014-09-02 | Thomas Daly | Biological buffers with wide buffering ranges |
US7635791B2 (en) * | 2008-04-17 | 2009-12-22 | Tpat Ip Llc | Biological buffers with wide buffering ranges |
US20170313920A1 (en) | 2010-10-06 | 2017-11-02 | Thomas P. Daly | Biological Buffers with Wide Buffering Ranges |
US8519141B2 (en) | 2008-04-17 | 2013-08-27 | Thomas Daly | Biological buffers with wide buffering ranges |
US9475754B2 (en) | 2011-10-06 | 2016-10-25 | Thomas P. Daly | Biological buffers with wide buffering ranges |
CN103086975A (zh) * | 2013-02-05 | 2013-05-08 | 广西师范大学 | 9-羟甲基-10-咪蒽腙及其合成方法和应用 |
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US2734920A (en) * | 1956-02-14 | New chemical compounds and their | ||
CH135949A (de) * | 1927-02-02 | 1929-10-15 | Ig Farbenindustrie Ag | Verfahren zur Herstellung einer chlorhaltigen Aldehydverbindung. |
US2194294A (en) * | 1938-07-16 | 1940-03-19 | Du Pont | Preparation of n-substituted alkylol amines |
US2865925A (en) * | 1956-03-23 | 1958-12-23 | Sterling Drug Inc | Process for preparing n-(2-hydroxyethyl)-n-(lower-alkyl)-9-aminomethylanthracenes and intermediates therein |
US3052722A (en) * | 1958-06-24 | 1962-09-04 | May & Baker Ltd | Aminophenoxyalkane derivatives |
US3198794A (en) * | 1960-07-25 | 1965-08-03 | Sterling Drug Inc | Pyrenylmethyl quaternary ammonium salts |
US3198835A (en) * | 1960-07-25 | 1965-08-03 | Sterling Drug Inc | Pyrenyl methyl tertiary amino amines |
FR95908E (fr) * | 1963-11-09 | 1972-01-31 | Degussa | Procédé de préparation de nouvelles aminocétones et des alcools secondaires correspondants. |
DE2123992C3 (de) * | 1971-05-14 | 1981-03-19 | Richardson-Merrell Inc., New York, N.Y. | 3,9-Bis-äther des Fluoranthens und deren Herstellung |
US4034040A (en) * | 1971-05-24 | 1977-07-05 | Pfizer Inc. | Xylene-diamines as antiviral agents |
US3882113A (en) * | 1972-12-21 | 1975-05-06 | Richardson Merrell Inc | Fluoranthene derivatives |
US4197149A (en) * | 1975-11-05 | 1980-04-08 | Sigri Elektrographit Gmbh | Method for joining together shaped bodies of polytetrafluoroethylene |
US4062958A (en) * | 1976-09-22 | 1977-12-13 | American Cyanamid Company | Method of treating anxiety and compositions therefor |
US4197249A (en) * | 1977-08-15 | 1980-04-08 | American Cyanamid Company | 1,4-Bis(substituted-amino)-5,8-dihydroxyanthraquinones and leuco bases thereof |
US4258181A (en) * | 1978-09-05 | 1981-03-24 | American Cyanamid Company | Substituted 9,10-anthracenebishydrazones |
EP0014434B1 (de) * | 1979-02-02 | 1983-05-18 | Ciba-Geigy Ag | Neues rechts-drehendes, basisches Derivat des 9,10-Aethano-anthracens, Verfahren zu dessen Herstellung und dieses enthaltende pharmazeutische Präparate |
US4211726A (en) * | 1979-02-16 | 1980-07-08 | American Cyanamid Company | Synthesis of substituted 9,10-anthracene-dicarboxaldehydes and 9,10-dihydro-9,10-anthracenedicarboxaldehydes |
JPS5999656A (ja) * | 1982-11-30 | 1984-06-08 | Toshiba Corp | 筒形空気電池 |
GB8313571D0 (en) * | 1983-05-17 | 1983-06-22 | Wellcome Found | Chemical compounds |
US4511582A (en) * | 1983-06-01 | 1985-04-16 | Burroughs Wellcome Co. | Phenanthrene derivatives |
US4532344A (en) * | 1983-05-23 | 1985-07-30 | Burroughs Wellcome Co. | Fluoranthene derivatives |
US4551282A (en) * | 1983-05-31 | 1985-11-05 | Burroughs Wellcome Co. | Triphenylene derivatives |
US4997249A (en) * | 1990-02-26 | 1991-03-05 | The United States Of America As Represented By The Secretary Of The Navy | Variable weight fiber optic transversal filter |
-
1983
- 1983-05-17 GB GB838313571A patent/GB8313571D0/en active Pending
- 1983-06-01 US US06/499,813 patent/US4530800A/en not_active Expired - Lifetime
-
1984
- 1984-05-16 EP EP84105585A patent/EP0125702B1/en not_active Expired
- 1984-05-16 EG EG315/84A patent/EG17595A/xx active
- 1984-05-16 IL IL71854A patent/IL71851A/xx not_active IP Right Cessation
- 1984-05-16 CS CS364584A patent/CS273314B2/cs unknown
- 1984-05-16 DD DD84263086A patent/DD223439A5/de not_active IP Right Cessation
- 1984-05-16 CA CA000454514A patent/CA1222750A/en not_active Expired
- 1984-05-16 JP JP59099655A patent/JPS59225149A/ja active Pending
- 1984-05-16 NO NO841954A patent/NO157416C/no unknown
- 1984-05-16 SU SU843744951A patent/SU1535377A3/ru active
- 1984-05-16 NZ NZ208168A patent/NZ208168A/en unknown
- 1984-05-16 DE DE8484105584T patent/DE3473141D1/de not_active Expired
- 1984-05-16 PH PH30683A patent/PH22265A/en unknown
- 1984-05-16 ZA ZA843708A patent/ZA843708B/xx unknown
- 1984-05-16 FI FI841966A patent/FI85263C/fi not_active IP Right Cessation
- 1984-05-16 GR GR74735A patent/GR82278B/el unknown
- 1984-05-16 MC MC841705A patent/MC1595A1/xx unknown
- 1984-05-16 JP JP59099656A patent/JPS59225150A/ja active Granted
- 1984-05-16 AU AU28098/84A patent/AU572509B2/en not_active Ceased
- 1984-05-16 DK DK242284A patent/DK242284A/da not_active Application Discontinuation
- 1984-05-16 KR KR1019840002647A patent/KR910000854B1/ko not_active Expired
- 1984-05-16 HU HU841886A patent/HU197875B/hu not_active IP Right Cessation
- 1984-05-16 ES ES532512A patent/ES8603376A1/es not_active Expired
- 1984-05-16 IE IE120384A patent/IE58416B1/en unknown
- 1984-05-16 PT PT78586A patent/PT78586A/pt not_active IP Right Cessation
- 1984-05-16 DE DE8484105585T patent/DE3465296D1/de not_active Expired
- 1984-05-16 EP EP84105584A patent/EP0125701B1/en not_active Expired
- 1984-05-16 GB GB08412485A patent/GB2140416B/en not_active Expired
- 1984-05-17 PL PL1984254244A patent/PL145420B1/pl unknown
- 1984-05-17 PL PL1984247759A patent/PL144294B1/pl unknown
- 1984-05-17 PL PL1984254245A patent/PL145421B1/pl unknown
- 1984-07-16 AP APAP/P/1984/000003A patent/AP1A/en active
- 1984-10-17 US US06/661,674 patent/US4720587A/en not_active Expired - Fee Related
- 1984-10-17 US US06/661,802 patent/US4719049A/en not_active Expired - Fee Related
- 1984-10-17 US US06/661,803 patent/US4719236A/en not_active Expired - Fee Related
-
1985
- 1985-02-06 ES ES540160A patent/ES8604487A1/es not_active Expired
- 1985-02-06 ES ES540161A patent/ES8603801A1/es not_active Expired
- 1985-04-22 US US06/725,157 patent/US4719047A/en not_active Expired - Fee Related
- 1985-08-30 SU SU853947162A patent/SU1466648A3/ru active
- 1985-12-02 SU SU853982431A patent/SU1447277A3/ru active
-
1987
- 1987-09-28 US US07/102,275 patent/US4820873A/en not_active Expired - Fee Related
-
1988
- 1988-03-11 AU AU13052/88A patent/AU599215B2/en not_active Ceased
-
1989
- 1989-04-08 SG SG223/89A patent/SG22389G/en unknown
- 1989-06-01 HK HK450/89A patent/HK45089A/en not_active IP Right Cessation
- 1989-12-08 CY CY1486A patent/CY1486A/xx unknown
-
1990
- 1990-06-01 JP JP2144246A patent/JPH0684336B2/ja not_active Expired - Lifetime
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