NO128224B - - Google Patents
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- Publication number
- NO128224B NO128224B NO01944/70A NO194470A NO128224B NO 128224 B NO128224 B NO 128224B NO 01944/70 A NO01944/70 A NO 01944/70A NO 194470 A NO194470 A NO 194470A NO 128224 B NO128224 B NO 128224B
- Authority
- NO
- Norway
- Prior art keywords
- triazine
- mol
- alkyl
- trimethyl
- substituted
- Prior art date
Links
- -1 methyl-substituted-adamantyl Chemical group 0.000 claims description 95
- 238000002360 preparation method Methods 0.000 claims description 80
- 150000001875 compounds Chemical class 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 18
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000003513 alkali Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical class NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 239000011968 lewis acid catalyst Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000000539 dimer Substances 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims description 2
- 239000013638 trimer Substances 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 112
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 89
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 67
- 239000000203 mixture Substances 0.000 description 66
- 239000000047 product Substances 0.000 description 63
- 239000000243 solution Substances 0.000 description 58
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 51
- 239000008096 xylene Substances 0.000 description 51
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 39
- 238000010992 reflux Methods 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 239000007787 solid Substances 0.000 description 33
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 30
- 150000001412 amines Chemical class 0.000 description 26
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 238000001953 recrystallisation Methods 0.000 description 24
- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 23
- 238000001914 filtration Methods 0.000 description 23
- 239000012043 crude product Substances 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 19
- 238000001816 cooling Methods 0.000 description 18
- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 14
- 241000699670 Mus sp. Species 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000007983 Tris buffer Substances 0.000 description 11
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 10
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- NFQMVGPOLFABQN-UHFFFAOYSA-N 6-chloro-2-n,4-n-bis(2,4,4-trimethylpentan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound CC(C)(C)CC(C)(C)NC1=NC(Cl)=NC(NC(C)(C)CC(C)(C)C)=N1 NFQMVGPOLFABQN-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000002002 slurry Substances 0.000 description 9
- DBUFHHJVYLAZLZ-UHFFFAOYSA-N 2-n,4-n,6-n-tris(2,4,4-trimethylpentan-2-yl)-1,3,5-triazine-2,4,6-triamine Chemical compound CC(C)(C)CC(C)(C)NC1=NC(NC(C)(C)CC(C)(C)C)=NC(NC(C)(C)CC(C)(C)C)=N1 DBUFHHJVYLAZLZ-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 6
- WOLHOYHSEKDWQH-UHFFFAOYSA-N amantadine hydrochloride Chemical compound [Cl-].C1C(C2)CC3CC2CC1([NH3+])C3 WOLHOYHSEKDWQH-UHFFFAOYSA-N 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 235000000891 standard diet Nutrition 0.000 description 6
- SDGKUVSVPIIUCF-UHFFFAOYSA-N 2,6-dimethylpiperidine Chemical compound CC1CCCC(C)N1 SDGKUVSVPIIUCF-UHFFFAOYSA-N 0.000 description 5
- 239000013067 intermediate product Substances 0.000 description 5
- 150000007974 melamines Chemical class 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 5
- ASKDWVZYNOOCIP-UHFFFAOYSA-N 2,4,6-trimethylcyclohexan-1-amine Chemical compound CC1CC(C)C(N)C(C)C1 ASKDWVZYNOOCIP-UHFFFAOYSA-N 0.000 description 4
- QHZRZIWCGRXBRY-UHFFFAOYSA-N 2-methylhexan-2-amine Chemical compound CCCCC(C)(C)N QHZRZIWCGRXBRY-UHFFFAOYSA-N 0.000 description 4
- MFVQBTPSCNUNAI-UHFFFAOYSA-N 2-n,4-n,6-n-tris(1-adamantyl)-1,3,5-triazine-2,4,6-triamine Chemical compound C1C(C2)CC(C3)CC2CC13NC1=NC(NC23CC4CC(C3)CC(C2)C4)=NC(NC23CC4CC(CC(C4)C2)C3)=N1 MFVQBTPSCNUNAI-UHFFFAOYSA-N 0.000 description 4
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 4
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 125000005073 adamantyl group Chemical class C12(CC3CC(CC(C1)C3)C2)* 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000005829 trimerization reaction Methods 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- ZEBFPAXSQXIPNF-UHFFFAOYSA-N 2,5-dimethylpyrrolidine Chemical compound CC1CCC(C)N1 ZEBFPAXSQXIPNF-UHFFFAOYSA-N 0.000 description 3
- DXSUORGKJZADET-UHFFFAOYSA-N 3,3-dimethylbutan-2-amine Chemical compound CC(N)C(C)(C)C DXSUORGKJZADET-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 150000003973 alkyl amines Chemical class 0.000 description 3
- 238000005576 amination reaction Methods 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- HBXNJMZWGSCKPW-UHFFFAOYSA-N octan-2-amine Chemical compound CCCCCCC(C)N HBXNJMZWGSCKPW-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 description 2
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- YQNVPNRHJFZONU-UHFFFAOYSA-N 2,3-dimethylbutan-2-amine Chemical compound CC(C)C(C)(C)N YQNVPNRHJFZONU-UHFFFAOYSA-N 0.000 description 2
- HKUBFVROJMSGFI-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ylcyanamide Chemical compound CC(C)(C)CC(C)(C)NC#N HKUBFVROJMSGFI-UHFFFAOYSA-N 0.000 description 2
- GELMWIVBBPAMIO-UHFFFAOYSA-N 2-methylbutan-2-amine Chemical compound CCC(C)(C)N GELMWIVBBPAMIO-UHFFFAOYSA-N 0.000 description 2
- XYKRYUFUYDCUFM-UHFFFAOYSA-N 2-n,4-n,6-n-tritert-butyl-1,3,5-triazine-2,4,6-triamine Chemical compound CC(C)(C)NC1=NC(NC(C)(C)C)=NC(NC(C)(C)C)=N1 XYKRYUFUYDCUFM-UHFFFAOYSA-N 0.000 description 2
- RKMAYERHOYIOBY-UHFFFAOYSA-N 6-chloro-2-n,4-n-bis(2,3,3-trimethylbutan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound CC(C)(C)C(C)(C)NC1=NC(Cl)=NC(NC(C)(C)C(C)(C)C)=N1 RKMAYERHOYIOBY-UHFFFAOYSA-N 0.000 description 2
- PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001646725 Mycobacterium tuberculosis H37Rv Species 0.000 description 2
- 108700035964 Mycobacterium tuberculosis HsaD Proteins 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- VYGQUTWHTHXGQB-FFHKNEKCSA-N Retinol Palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C VYGQUTWHTHXGQB-FFHKNEKCSA-N 0.000 description 2
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 150000001912 cyanamides Chemical class 0.000 description 2
- HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical compound NC1CCCCCCC1 HSOHBWMXECKEKV-UHFFFAOYSA-N 0.000 description 2
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 2
- 229940038472 dicalcium phosphate Drugs 0.000 description 2
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
- IBQCYUBVFOFMRI-UHFFFAOYSA-N tert-butylcyanamide Chemical compound CC(C)(C)NC#N IBQCYUBVFOFMRI-UHFFFAOYSA-N 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- ZZJREAPISLZYCW-UHFFFAOYSA-N 1,3,5-triazine-2,4,6-tricarbonitrile Chemical compound N#CC1=NC(C#N)=NC(C#N)=N1 ZZJREAPISLZYCW-UHFFFAOYSA-N 0.000 description 1
- UQYYBDRECPZRSP-UHFFFAOYSA-N 1-adamantylcyanamide Chemical compound C1C(C2)CC3CC2CC1(NC#N)C3 UQYYBDRECPZRSP-UHFFFAOYSA-N 0.000 description 1
- VBLHYILVPSSTFU-UHFFFAOYSA-N 2,3,3-trimethylbutan-2-amine;hydrochloride Chemical compound Cl.CC(C)(C)C(C)(C)N VBLHYILVPSSTFU-UHFFFAOYSA-N 0.000 description 1
- GIFULPYOUNQWML-UHFFFAOYSA-N 2,3,3-trimethylbutan-2-ylcyanamide Chemical compound CC(C)(C)C(C)(C)NC#N GIFULPYOUNQWML-UHFFFAOYSA-N 0.000 description 1
- BJPDXMOHQOQSGJ-UHFFFAOYSA-N 2,3-dimethylhexan-2-amine Chemical compound CCCC(C)C(C)(C)N BJPDXMOHQOQSGJ-UHFFFAOYSA-N 0.000 description 1
- LZOPUSYIUDCHIT-UHFFFAOYSA-N 2,3-dimethylpentan-3-amine Chemical compound CCC(C)(N)C(C)C LZOPUSYIUDCHIT-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82704869A | 1969-05-22 | 1969-05-22 | |
| US82703269A | 1969-05-22 | 1969-05-22 | |
| US82703169A | 1969-05-22 | 1969-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO128224B true NO128224B (ja) | 1973-10-15 |
Family
ID=27420190
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO01944/70A NO128224B (ja) | 1969-05-22 | 1970-05-21 |
Country Status (17)
| Country | Link |
|---|---|
| JP (2) | JPS4839945B1 (ja) |
| AT (1) | AT306041B (ja) |
| BG (1) | BG20376A3 (ja) |
| BR (1) | BR6915234D0 (ja) |
| CH (1) | CH549589A (ja) |
| CS (2) | CS167921B2 (ja) |
| DE (1) | DE2025080A1 (ja) |
| FR (1) | FR2051553B1 (ja) |
| GB (1) | GB1308811A (ja) |
| HU (1) | HU164355B (ja) |
| IE (1) | IE34877B1 (ja) |
| IL (1) | IL34286A (ja) |
| NL (1) | NL7007103A (ja) |
| NO (1) | NO128224B (ja) |
| OA (1) | OA04242A (ja) |
| RO (1) | RO57534A (ja) |
| ZM (1) | ZM4370A1 (ja) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA791262B (en) * | 1978-04-12 | 1980-07-30 | American Cyanamid Co | Novel anti-arthritic 2,4,6-tris.(substituted-amino)-striazines |
| JPS576367A (en) * | 1980-06-12 | 1982-01-13 | Chubu Electric Power Co Inc | Method for detecting partial discharge of power cable |
| JPS5991376A (ja) * | 1982-11-16 | 1984-05-26 | Kansai Electric Power Co Inc:The | 電力ケ−ブルの絶縁劣化診断方法 |
| DE3611427A1 (de) * | 1986-04-05 | 1987-10-08 | Hoechst Ag | Bis-tertiaerbutylamino-substituierte 1,3,5-triazinderivate, verfahren zu ihrer herstellung, diese verbindungen enthaltende arzneimittel und ihre verwendung |
| JPS62155323A (ja) * | 1986-12-27 | 1987-07-10 | Nippon Seiko Kk | 動圧形複合軸受装置 |
| JPS63150914U (ja) * | 1987-03-24 | 1988-10-04 | ||
| AT389303B (de) * | 1987-10-08 | 1989-11-27 | Hoechst Ag | Neue bis-tertiaerbutylamino-substituierte 1,3,5-triazinderivate, verfahren zu ihrer herstellung, diese verbindungen enthaltende arzneimittel und ihre verwendung |
| AU621082B2 (en) * | 1988-02-08 | 1992-03-05 | Ciba-Geigy Ag | Tetramethylpiperidino-s-triazines |
| AR036375A1 (es) | 2001-08-30 | 2004-09-01 | Novartis Ag | Compuestos pirrolo [2,3-d] pirimidina -2- carbonitrilo, un proceso para su preparacion, una composicion farmaceutica y el uso de dichos compuestos para la preparacion de medicamentos |
| SE0201976D0 (sv) * | 2002-06-24 | 2002-06-24 | Astrazeneca Ab | Novel compounds |
| WO2009028891A2 (en) * | 2007-08-31 | 2009-03-05 | Hanall Pharmaceutical Company. Ltd | 1,3,5-triazine-2,4,6-triamine compound or pharmaceutical acceptable salt thereof, and pharmaceutical composition comprising the same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2691021A (en) * | 1954-10-05 | Trimerization of t |
-
1969
- 1969-12-16 BR BR215234/69A patent/BR6915234D0/pt unknown
-
1970
- 1970-04-03 IE IE421/70A patent/IE34877B1/xx unknown
- 1970-04-09 IL IL34286A patent/IL34286A/xx unknown
- 1970-04-14 ZM ZM43/70A patent/ZM4370A1/xx unknown
- 1970-05-15 NL NL7007103A patent/NL7007103A/xx unknown
- 1970-05-19 CS CS3481A patent/CS167921B2/cs unknown
- 1970-05-19 BG BG23461A patent/BG20376A3/xx unknown
- 1970-05-19 CS CS4959*A patent/CS167922B2/cs unknown
- 1970-05-19 RO RO63393A patent/RO57534A/ro unknown
- 1970-05-21 CH CH753270A patent/CH549589A/xx not_active IP Right Cessation
- 1970-05-21 NO NO01944/70A patent/NO128224B/no unknown
- 1970-05-21 HU HUAE319A patent/HU164355B/hu unknown
- 1970-05-22 AT AT463170A patent/AT306041B/de not_active IP Right Cessation
- 1970-05-22 FR FR7018738A patent/FR2051553B1/fr not_active Expired
- 1970-05-22 OA OA53930A patent/OA04242A/xx unknown
- 1970-05-22 GB GB2497470A patent/GB1308811A/en not_active Expired
- 1970-05-22 JP JP45043955A patent/JPS4839945B1/ja active Pending
- 1970-05-22 DE DE19702025080 patent/DE2025080A1/de not_active Withdrawn
-
1971
- 1971-12-23 JP JP46105126A patent/JPS4917272B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| HU164355B (ja) | 1974-02-28 |
| BR6915234D0 (pt) | 1973-06-07 |
| BG20376A3 (ja) | 1975-11-05 |
| CS167922B2 (ja) | 1976-05-28 |
| IL34286A0 (en) | 1970-12-24 |
| RO57534A (ja) | 1975-01-15 |
| CS167921B2 (ja) | 1976-05-28 |
| NL7007103A (ja) | 1970-11-24 |
| ZM4370A1 (en) | 1971-02-22 |
| FR2051553A1 (ja) | 1971-04-09 |
| JPS4917272B1 (ja) | 1974-04-27 |
| DE2025080A1 (de) | 1970-11-26 |
| IE34877L (en) | 1975-09-17 |
| OA04242A (fr) | 1979-12-31 |
| JPS4839945B1 (ja) | 1973-11-28 |
| CH549589A (de) | 1974-05-31 |
| AT306041B (de) | 1973-03-26 |
| IE34877B1 (en) | 1975-09-17 |
| FR2051553B1 (ja) | 1976-04-16 |
| GB1308811A (en) | 1973-03-07 |
| IL34286A (en) | 1974-03-14 |
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