NO820201L - Fremgangsmaate til fremstilling av nye n-substituerte polyglycidyl-urazolforbindelser - Google Patents

Fremgangsmaate til fremstilling av nye n-substituerte polyglycidyl-urazolforbindelser

Info

Publication number: NO820201L
Authority: NO; Norway
Prior art keywords: residue; urazole; reaction; residues; glycidyl
Prior art date: 1981-01-24

Application number

NO820201A

Other languages

English (en)

Norwegian (no)

Inventor

Herbert Fischer

Brigitte Hase

Hinrich Moeller

Hans-Christoph Wilk

Ulrich Zeidler

Original Assignee

Henkel Kgaa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1981-01-24

Filing date

1982-01-22

Publication date

1982-07-26

1982-01-22 Application filed by Henkel Kgaa filed Critical Henkel Kgaa

1982-07-26 Publication of NO820201L publication Critical patent/NO820201L/no

Links

238000000034 method Methods 0.000 title claims description 25
238000002360 preparation method Methods 0.000 title claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 25
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
239000001257 hydrogen Substances 0.000 claims abstract description 21
UDATXMIGEVPXTR-UHFFFAOYSA-N 1,2,4-triazolidine-3,5-dione Chemical class O=C1NNC(=O)N1 UDATXMIGEVPXTR-UHFFFAOYSA-N 0.000 claims abstract description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
125000005842 heteroatom Chemical group 0.000 claims abstract description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052799 carbon Inorganic materials 0.000 claims abstract description 7
-1 monosubstituted urazole Chemical class 0.000 claims description 63
150000001875 compounds Chemical class 0.000 claims description 50
238000006243 chemical reaction Methods 0.000 claims description 36
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 35
ZTXDHEQQZVFGPK-UHFFFAOYSA-N 1,2,4-tris(oxiran-2-ylmethyl)-1,2,4-triazolidine-3,5-dione Chemical compound C1OC1CN1C(=O)N(CC2OC2)C(=O)N1CC1CO1 ZTXDHEQQZVFGPK-UHFFFAOYSA-N 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 15
229910052736 halogen Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 12
239000007795 chemical reaction product Substances 0.000 claims description 10
150000002924 oxiranes Chemical group 0.000 claims description 10
238000006735 epoxidation reaction Methods 0.000 claims description 7
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
230000035484 reaction time Effects 0.000 claims description 4
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
239000011541 reaction mixture Substances 0.000 claims description 3
150000001735 carboxylic acids Chemical class 0.000 claims description 2
125000003700 epoxy group Chemical group 0.000 claims description 2
150000003949 imides Chemical class 0.000 claims description 2
150000002466 imines Chemical class 0.000 claims description 2
150000003141 primary amines Chemical class 0.000 claims description 2
150000003335 secondary amines Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
208000032839 leukemia Diseases 0.000 abstract description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
125000001424 substituent group Chemical group 0.000 description 19
239000000203 mixture Substances 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
241000699666 Mus <mouse, genus> Species 0.000 description 11
239000002253 acid Substances 0.000 description 11
125000000623 heterocyclic group Chemical group 0.000 description 10
239000000243 solution Substances 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000013543 active substance Substances 0.000 description 8
125000003118 aryl group Chemical group 0.000 description 8
238000004440 column chromatography Methods 0.000 description 8
239000000047 product Substances 0.000 description 8
125000003545 alkoxy group Chemical group 0.000 description 7
230000001085 cytostatic effect Effects 0.000 description 7
238000007344 nucleophilic reaction Methods 0.000 description 7
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000000126 substance Substances 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 5
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 5
125000004423 acyloxy group Chemical group 0.000 description 5
239000012043 crude product Substances 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
150000004965 peroxy acids Chemical group 0.000 description 5
230000002829 reductive effect Effects 0.000 description 5
238000000926 separation method Methods 0.000 description 5
235000011121 sodium hydroxide Nutrition 0.000 description 5
239000007858 starting material Substances 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
125000005332 alkyl sulfoxy group Chemical group 0.000 description 4
125000004414 alkyl thio group Chemical group 0.000 description 4
125000003710 aryl alkyl group Chemical group 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
238000006704 dehydrohalogenation reaction Methods 0.000 description 4
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 4
239000003480 eluent Substances 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000002808 molecular sieve Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
238000001953 recrystallisation Methods 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
238000003786 synthesis reaction Methods 0.000 description 4
230000007306 turnover Effects 0.000 description 4
WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 3
QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
206010028980 Neoplasm Diseases 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000002877 alkyl aryl group Chemical group 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
235000019439 ethyl acetate Nutrition 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000011049 filling Methods 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
239000003444 phase transfer catalyst Substances 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 2
ZRKMQKLGEQPLNS-UHFFFAOYSA-N 1-Pentanethiol Chemical compound CCCCCS ZRKMQKLGEQPLNS-UHFFFAOYSA-N 0.000 description 2
ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 2
BDFAOUQQXJIZDG-UHFFFAOYSA-N 2-methylpropane-1-thiol Chemical compound CC(C)CS BDFAOUQQXJIZDG-UHFFFAOYSA-N 0.000 description 2
MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000001502 aryl halides Chemical class 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-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
201000011510 cancer Diseases 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
239000000824 cytostatic agent Substances 0.000 description 2
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
230000006735 deficit Effects 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
238000002955 isolation Methods 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
MKUWVMRNQOOSAT-UHFFFAOYSA-N methylvinylmethanol Natural products CC(O)C=C MKUWVMRNQOOSAT-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 2
AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
238000003408 phase transfer catalysis Methods 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000003880 polar aprotic solvent Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000000547 substituted alkyl group Chemical group 0.000 description 2
230000004083 survival effect Effects 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
125000005023 xylyl group Chemical group 0.000 description 2
OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
229940043375 1,5-pentanediol Drugs 0.000 description 1
HYACHWAAHOWKLJ-UHFFFAOYSA-N 1-(2-hydroxy-3-morpholin-4-ylpropyl)-2,4-bis(oxiran-2-ylmethyl)-1,2,4-triazolidine-3,5-dione Chemical compound C1OC1CN1C(=O)N(CC2OC2)C(=O)N1CC(O)CN1CCOCC1 HYACHWAAHOWKLJ-UHFFFAOYSA-N 0.000 description 1
FCWPYNQXXSPACI-UHFFFAOYSA-N 1-(oxiran-2-ylmethyl)-1,2,4-triazolidine-3,5-dione Chemical compound O=C1NC(=O)NN1CC1OC1 FCWPYNQXXSPACI-UHFFFAOYSA-N 0.000 description 1
PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 1
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
FAXJFVQAGPWKHQ-UHFFFAOYSA-N 2,2,3-trichlorobutanoic acid Chemical compound CC(Cl)C(Cl)(Cl)C(O)=O FAXJFVQAGPWKHQ-UHFFFAOYSA-N 0.000 description 1
VGVRPFIJEJYOFN-UHFFFAOYSA-N 2,3,4,6-tetrachlorophenol Chemical class OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl VGVRPFIJEJYOFN-UHFFFAOYSA-N 0.000 description 1
XRUGBBIQLIVCSI-UHFFFAOYSA-N 2,3,4-trimethylphenol Chemical compound CC1=CC=C(O)C(C)=C1C XRUGBBIQLIVCSI-UHFFFAOYSA-N 0.000 description 1
YVKJJOQJKFNVEI-UHFFFAOYSA-N 2,3-dichlorobutanoic acid Chemical compound CC(Cl)C(Cl)C(O)=O YVKJJOQJKFNVEI-UHFFFAOYSA-N 0.000 description 1
GKFWNPPZHDYVLI-UHFFFAOYSA-N 2,3-dichloropropanoic acid Chemical compound OC(=O)C(Cl)CCl GKFWNPPZHDYVLI-UHFFFAOYSA-N 0.000 description 1
IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical class CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical class CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 1
NZZYVDKRZFWNRJ-UHFFFAOYSA-N 2-chloro-2-methylbutanoic acid Chemical compound CCC(C)(Cl)C(O)=O NZZYVDKRZFWNRJ-UHFFFAOYSA-N 0.000 description 1
MYCXCBCDXVFXNE-UHFFFAOYSA-N 2-chloro-2-methylpropanoic acid Chemical compound CC(C)(Cl)C(O)=O MYCXCBCDXVFXNE-UHFFFAOYSA-N 0.000 description 1
DDTJFSPKEIAZAM-UHFFFAOYSA-N 2-chloro-3-methylbutanoic acid Chemical compound CC(C)C(Cl)C(O)=O DDTJFSPKEIAZAM-UHFFFAOYSA-N 0.000 description 1
RVBUZBPJAGZHSQ-UHFFFAOYSA-N 2-chlorobutanoic acid Chemical compound CCC(Cl)C(O)=O RVBUZBPJAGZHSQ-UHFFFAOYSA-N 0.000 description 1
WZZRDRYYUVHLRD-UHFFFAOYSA-N 2-chloropentanoic acid Chemical compound CCCC(Cl)C(O)=O WZZRDRYYUVHLRD-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
UIERETOOQGIECD-UHFFFAOYSA-N 2-methylbut-2-enoic acid Chemical compound CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 1
BIWVHGWGBMHTTP-UHFFFAOYSA-N 2-methylbutane-1,1-diol Chemical compound CCC(C)C(O)O BIWVHGWGBMHTTP-UHFFFAOYSA-N 0.000 description 1
LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical class CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 description 1
HFPLCFMATPQWMD-UHFFFAOYSA-N 3,3-dichloro-propionic acid Chemical compound OC(=O)CC(Cl)Cl HFPLCFMATPQWMD-UHFFFAOYSA-N 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
YBJGQSNSAWZZHL-UHFFFAOYSA-N 3-chloro-2,2-dimethylpropanoic acid Chemical compound ClCC(C)(C)C(O)=O YBJGQSNSAWZZHL-UHFFFAOYSA-N 0.000 description 1
WADQOGCINABPRT-UHFFFAOYSA-N 3-chloro-2-methylphenol Chemical class CC1=C(O)C=CC=C1Cl WADQOGCINABPRT-UHFFFAOYSA-N 0.000 description 1
AWSSTZZQBPIWKZ-UHFFFAOYSA-N 3-chloro-2-methylpropanoic acid Chemical compound ClCC(C)C(O)=O AWSSTZZQBPIWKZ-UHFFFAOYSA-N 0.000 description 1
OVLLWBPWBDJZIZ-UHFFFAOYSA-N 3-chloropentanoic acid Chemical compound CCC(Cl)CC(O)=O OVLLWBPWBDJZIZ-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
QEYMMOKECZBKAC-UHFFFAOYSA-N 3-chloropropanoic acid Chemical compound OC(=O)CCCl QEYMMOKECZBKAC-UHFFFAOYSA-N 0.000 description 1
FRDAATYAJDYRNW-UHFFFAOYSA-N 3-methyl-3-pentanol Chemical compound CCC(C)(O)CC FRDAATYAJDYRNW-UHFFFAOYSA-N 0.000 description 1
SPVVMXMTSODFPU-UHFFFAOYSA-N 3-methyl-n-(3-methylbutyl)butan-1-amine Chemical compound CC(C)CCNCCC(C)C SPVVMXMTSODFPU-UHFFFAOYSA-N 0.000 description 1
BFQPCKPYOLVRAM-UHFFFAOYSA-N 4-butyl-1,2,4-triazolidine-3,5-dione Chemical compound CCCCN1C(=O)NNC1=O BFQPCKPYOLVRAM-UHFFFAOYSA-N 0.000 description 1
LDLHZRKZQVFLRK-UHFFFAOYSA-N 4-butyl-1,2-bis(oxiran-2-ylmethyl)-1,2,4-triazolidine-3,5-dione Chemical compound C1OC1CN1C(=O)N(CCCC)C(=O)N1CC1CO1 LDLHZRKZQVFLRK-UHFFFAOYSA-N 0.000 description 1
IPLKGJHGWCVSOG-UHFFFAOYSA-N 4-chlorobutanoic acid Chemical compound OC(=O)CCCCl IPLKGJHGWCVSOG-UHFFFAOYSA-N 0.000 description 1
LTGIPHNDQJAHEO-UHFFFAOYSA-N 4-chloropentanoic acid Chemical compound CC(Cl)CCC(O)=O LTGIPHNDQJAHEO-UHFFFAOYSA-N 0.000 description 1
SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
KOVAQMSVARJMPH-UHFFFAOYSA-N 4-methoxybutan-1-ol Chemical compound COCCCCO KOVAQMSVARJMPH-UHFFFAOYSA-N 0.000 description 1
XJOOWWMZMXBLAO-UHFFFAOYSA-N 4-methyl-1,2,4-triazolidine-3,5-dione Chemical compound CN1C(=O)NNC1=O XJOOWWMZMXBLAO-UHFFFAOYSA-N 0.000 description 1
SZJJDASHSUBSJO-UHFFFAOYSA-N 4-methyl-1,2-bis(oxiran-2-ylmethyl)-1,2,4-triazolidine-3,5-dione Chemical compound C1OC1CN1C(=O)N(C)C(=O)N1CC1CO1 SZJJDASHSUBSJO-UHFFFAOYSA-N 0.000 description 1
WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 1
GOSUFRDROXZXLN-UHFFFAOYSA-N 4-phenyl-1,2,4-triazolidine-3,5-dione Chemical compound O=C1NNC(=O)N1C1=CC=CC=C1 GOSUFRDROXZXLN-UHFFFAOYSA-N 0.000 description 1
OJFZXRZZXBFEAP-UHFFFAOYSA-N 5-chloro-1,6-dimethylcyclohexa-2,4-dien-1-ol Chemical class ClC=1C(C(C=CC1)(C)O)C OJFZXRZZXBFEAP-UHFFFAOYSA-N 0.000 description 1
YSXDKDWNIPOSMF-UHFFFAOYSA-N 5-chloropentanoic acid Chemical compound OC(=O)CCCCCl YSXDKDWNIPOSMF-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
206010009944 Colon cancer Diseases 0.000 description 1
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
WSWCOQWTEOXDQX-MQQKCMAXSA-N E-Sorbic acid Chemical compound C\C=C\C=C\C(O)=O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
240000000731 Fagus sylvatica Species 0.000 description 1
235000010099 Fagus sylvatica Nutrition 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
206010058467 Lung neoplasm malignant Diseases 0.000 description 1
XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
206010039491 Sarcoma Diseases 0.000 description 1
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
SWEDAZLCYJDAGW-UHFFFAOYSA-N Thiophene-2-thiol Chemical compound SC1=CC=CS1 SWEDAZLCYJDAGW-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
125000000746 allylic group Chemical group 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000003868 ammonium compounds Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
159000000032 aromatic acids Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
WYLQRHZSKIDFEP-UHFFFAOYSA-N benzene-1,4-dithiol Chemical compound SC1=CC=C(S)C=C1 WYLQRHZSKIDFEP-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000001559 benzoic acids Chemical class 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
DLDJFQGPPSQZKI-UHFFFAOYSA-N but-2-yne-1,4-diol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 description 1
RVOWKOVQKFONKL-UHFFFAOYSA-N but-3-ene-2,2-diol Chemical compound CC(O)(O)C=C RVOWKOVQKFONKL-UHFFFAOYSA-N 0.000 description 1
GKPOMITUDGXOSB-UHFFFAOYSA-N but-3-yn-2-ol Chemical compound CC(O)C#C GKPOMITUDGXOSB-UHFFFAOYSA-N 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
LOCHFZBWPCLPAN-UHFFFAOYSA-N butane-2-thiol Chemical compound CCC(C)S LOCHFZBWPCLPAN-UHFFFAOYSA-N 0.000 description 1
WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 1
PXGPQCBSBQOPLZ-UHFFFAOYSA-N butanoic acid;propanoic acid Chemical compound CCC(O)=O.CCCC(O)=O PXGPQCBSBQOPLZ-UHFFFAOYSA-N 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
239000000969 carrier Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000002648 combination therapy Methods 0.000 description 1
239000013065 commercial product Substances 0.000 description 1
150000001896 cresols Chemical class 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical compound NC1CCCCCCC1 HSOHBWMXECKEKV-UHFFFAOYSA-N 0.000 description 1
229960004397 cyclophosphamide Drugs 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
125000004990 dihydroxyalkyl group Chemical group 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229960002949 fluorouracil Drugs 0.000 description 1
WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000003944 halohydrins Chemical class 0.000 description 1
ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000009413 insulation Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
235000021190 leftovers Nutrition 0.000 description 1
201000005296 lung carcinoma Diseases 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
201000001441 melanoma Diseases 0.000 description 1
239000000155 melt Substances 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
OBYVIBDTOCAXSN-UHFFFAOYSA-N n-butan-2-ylbutan-2-amine Chemical compound CCC(C)NC(C)CC OBYVIBDTOCAXSN-UHFFFAOYSA-N 0.000 description 1
JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 1
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
150000002829 nitrogen Chemical class 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical class CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000000039 preparative column chromatography Methods 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 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
239000000376 reactant Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
238000005245 sintering Methods 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000005415 substituted alkoxy group Chemical group 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000002023 wood Substances 0.000 description 1
150000003739 xylenols Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Epoxy Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Epoxy Resins (AREA)
Phenolic Resins Or Amino Resins (AREA)
Saccharide Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO820201A 1981-01-24 1982-01-22 Fremgangsmaate til fremstilling av nye n-substituerte polyglycidyl-urazolforbindelser NO820201L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19813102373 DE3102373A1 (de)	1981-01-24	1981-01-24	"neue n-substituierte polyglycidyl-urazolverbindungen, verfahren zu ihrer herstellung sowie pharmzeutische zubereitungen

Publications (1)

Publication Number	Publication Date
NO820201L true NO820201L (no)	1982-07-26

Family

ID=6123305

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO820201A NO820201L (no)	1981-01-24	1982-01-22	Fremgangsmaate til fremstilling av nye n-substituerte polyglycidyl-urazolforbindelser

Country Status (21)

Country	Link
US (1)	US4801601A (es)
EP (1)	EP0056962B1 (es)
JP (1)	JPS57142982A (es)
KR (1)	KR880001106B1 (es)
AT (1)	ATE15898T1 (es)
AU (1)	AU548803B2 (es)
CA (1)	CA1197847A (es)
CS (1)	CS252809B2 (es)
DD (1)	DD202025A5 (es)
DE (2)	DE3102373A1 (es)
DK (1)	DK27882A (es)
ES (1)	ES508992A0 (es)
FI (1)	FI71934C (es)
HU (1)	HU189557B (es)
IE (1)	IE51930B1 (es)
IL (1)	IL64844A (es)
NO (1)	NO820201L (es)
NZ (1)	NZ199485A (es)
PL (1)	PL135459B1 (es)
SU (2)	SU1118287A3 (es)
ZA (1)	ZA82451B (es)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3330640A1 (de) *	1983-08-25	1985-03-14	Henkel KGaA, 4000 Düsseldorf	Verfahren zur addition von saeuren an glycidylverbindungen
DE3336693A1 (de) *	1983-10-08	1985-04-25	Henkel KGaA, 4000 Düsseldorf	Antitumormittel
WO2012050591A1 (en)	2010-10-15	2012-04-19	Rutgers, The State University Of New Jersey	Hydrogel formulation for dermal and ocular delivery
US20090104254A1 (en)	2004-12-22	2009-04-23	Rutgers, The State University Of New Jersey	Controlled Release Hydrogels

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2935354A1 (de) *	1979-09-01	1981-03-19	Bayer Ag, 5090 Leverkusen	Triglycidyl-triazolidin-3,5-dione und verfahren zu ihrer herstellung
ATE22080T1 (de) *	1980-01-31	1986-09-15	Henkel Kgaa	Arzneimittel mit cytostatischer wirkung sowie verwendung von mehrfach mit glycidylgruppen substituierten n-heterocyclischen ringverbindungen in pharmazeutischen zubereitungen.
DE3027623A1 (de) *	1980-07-21	1982-02-18	Bayer Ag, 5090 Leverkusen	Neue glycidyl-1,2,4-triazolidin-3,5-dione und ein verfahren zu ihrer herstellung

1981
- 1981-01-24 DE DE19813102373 patent/DE3102373A1/de not_active Withdrawn
1982
- 1982-01-14 NZ NZ199485A patent/NZ199485A/en unknown
- 1982-01-16 DE DE8282100279T patent/DE3266588D1/de not_active Expired
- 1982-01-16 EP EP82100279A patent/EP0056962B1/de not_active Expired
- 1982-01-16 AT AT82100279T patent/ATE15898T1/de not_active IP Right Cessation
- 1982-01-20 SU SU823381945A patent/SU1118287A3/ru active
- 1982-01-20 CA CA000394555A patent/CA1197847A/en not_active Expired
- 1982-01-22 NO NO820201A patent/NO820201L/no unknown
- 1982-01-22 IL IL64844A patent/IL64844A/xx unknown
- 1982-01-22 AU AU79743/82A patent/AU548803B2/en not_active Ceased
- 1982-01-22 IE IE133/82A patent/IE51930B1/en unknown
- 1982-01-22 ZA ZA82451A patent/ZA82451B/xx unknown
- 1982-01-22 DK DK27882A patent/DK27882A/da not_active Application Discontinuation
- 1982-01-22 ES ES508992A patent/ES508992A0/es active Granted
- 1982-01-22 HU HU82190A patent/HU189557B/hu unknown
- 1982-01-22 FI FI820201A patent/FI71934C/fi not_active IP Right Cessation
- 1982-01-23 KR KR8200297A patent/KR880001106B1/ko active
- 1982-01-25 JP JP57010815A patent/JPS57142982A/ja active Pending
- 1982-01-25 CS CS82507A patent/CS252809B2/cs unknown
- 1982-01-25 DD DD82236947A patent/DD202025A5/de unknown
- 1982-01-25 PL PL1982234828A patent/PL135459B1/pl unknown
- 1982-09-29 SU SU823495515A patent/SU1074405A3/ru active
1986
- 1986-02-20 US US06/831,373 patent/US4801601A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
KR830009063A (ko)	1983-12-17
SU1118287A3 (ru)	1984-10-07
ES8302695A1 (es)	1982-12-01
ATE15898T1 (de)	1985-10-15
IL64844A (en)	1986-10-31
IE51930B1 (en)	1987-04-29
CS252809B2 (en)	1987-10-15
ES508992A0 (es)	1982-12-01
FI71934B (fi)	1986-11-28
AU7974382A (en)	1982-08-05
EP0056962B1 (de)	1985-10-02
ZA82451B (en)	1982-12-29
PL234828A1 (en)	1983-04-11
EP0056962A3 (en)	1982-08-25
IE820133L (en)	1982-07-24
AU548803B2 (en)	1986-01-02
NZ199485A (en)	1984-05-31
EP0056962A2 (de)	1982-08-04
DK27882A (da)	1982-07-25
CS50782A2 (en)	1986-12-18
DD202025A5 (de)	1983-08-24
IL64844A0 (en)	1982-03-31
CA1197847A (en)	1985-12-10
DE3266588D1 (en)	1985-11-07
FI820201L (fi)	1982-07-25
SU1074405A3 (ru)	1984-02-15
DE3102373A1 (de)	1982-08-26
FI71934C (fi)	1987-03-09
JPS57142982A (en)	1982-09-03
HU189557B (en)	1986-07-28
KR880001106B1 (ko)	1988-06-29
US4801601A (en)	1989-01-31
PL135459B1 (en)	1985-10-31

Publication	Publication Date	Title
AU2019346118B2 (en)	2024-05-16	Manufacture of compounds and compositions for inhibiting the activity of SHP2
US4393060A (en)	1983-07-12	Isocyanuric acid derivatives, method of preparation, therapeutic compositions with a cytostatic action and therapeutic method
DE68911417T2 (de)	1994-04-14	Cyclohexan-Derivate.
JPH0649697B2 (ja)	1994-06-29	放射線治療または化学療法に有用な化合物
NO820201L (no)	1982-07-26	Fremgangsmaate til fremstilling av nye n-substituerte polyglycidyl-urazolforbindelser
NO155880B (no)	1987-03-09	Analogifremgangsmaate til fremstilling av terapeutisk aktivt 2-(2'hydroksy-3'-(1,1-dimetylpropylamino)-propoksy)-beta-fenylpropionfenon.
US4376120A (en)	1983-03-08	Therapeutic compositions with a cytostatic action containing isocyanuric acid derivatives and process of manufacture
WO1998052551A1 (fr)	1998-11-26	Composes bisaryle et remedes contre le cancer contenant ces composes
JPS6058747B2 (ja)	1985-12-21	アミノ化合物の製法
Kim et al.	1983	Synthesis and antileukemic activity of 2-(2-methylthio-2-aminovinyl)-1-methylquinolinium iodides
FI61871C (fi)	1982-10-11	Analogifoerfarande foer framstaellning av antidepressivt verkande trifluormetylsubstituerade aralkylestrar av alanin
CA1179266A (en)	1984-12-11	Isocyanuric acid derivatives, method of preparation, therapeutic compositions with a cytostatic action and therapeutic method
AU2021222332A1 (en)	2022-10-20	Macrocyclic indole derivatives as inhibitors of MCL-1
CS212669B1 (en)	1982-03-26	Basic esters of the 7-oxo-7h-benzo/c/fluorene and method of preparation thereof
Gleiter et al.	1987	A [1, 2] and a [1, 4] shift in a Wittig thioether rearrangement. Isolation of a [1.1](2, 8) naphthalenophane tautomer
JPS5829785A (ja)	1983-02-22	新規ジグリシジル−プテリジン化合物、その製造法、及びこれを含有し細胞静止作用を有する薬剤調合物
CS202007B2 (en)	1980-12-31	Method of producing aminoderivatives of 4-hydroxy-1,2-benzoisothiazole
JPH049386A (ja)	1992-01-14	６Ｈ―チオピラノ［３，２―ｄ］ピリミジン誘導体およびその製造法
JPS6293272A (ja)	1987-04-28	ピペラジン誘導体及びその製法
FR2570376A1 (fr)	1986-03-21	Nouveaux (isopropyl-5 (((methoxy-2 phenyl) piperazinyl)-2 ethoxy)-4 methyl-2 phenoxy)-1 alkylamino-3 propanols-2, leur methode de preparation et leur application therapeutique
JPS62116568A (ja)	1987-05-28	チアゾリジン誘導体及びその製法
PL98225B1 (pl)	1978-04-29	Sposob wytwarzania nowych pochodnych 1-fenoksy-2-hydroksy-3-aminopropanu