BG65184B1 - Метод и реагенти за количествено определяне на твърдофазовите реакции, използвайки флуорен ямр - Google Patents
Метод и реагенти за количествено определяне на твърдофазовите реакции, използвайки флуорен ямр Download PDFInfo
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- BG65184B1 BG65184B1 BG104614A BG10461400A BG65184B1 BG 65184 B1 BG65184 B1 BG 65184B1 BG 104614 A BG104614 A BG 104614A BG 10461400 A BG10461400 A BG 10461400A BG 65184 B1 BG65184 B1 BG 65184B1
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- Prior art keywords
- fluorine
- solid
- group
- synthetic resin
- phase reaction
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- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 82
- 238000003746 solid phase reaction Methods 0.000 title claims abstract description 77
- 239000011737 fluorine Substances 0.000 title claims abstract description 76
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 70
- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims description 38
- 238000011002 quantification Methods 0.000 title claims description 3
- 239000007790 solid phase Substances 0.000 claims abstract description 26
- -1 imidazole- 1-yl Chemical group 0.000 claims description 146
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 239000007787 solid Substances 0.000 claims description 19
- 239000007795 chemical reaction product Substances 0.000 claims description 18
- 125000001153 fluoro group Chemical group F* 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 125000000524 functional group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000006242 amine protecting group Chemical group 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 6
- 238000009987 spinning Methods 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 230000000977 initiatory effect Effects 0.000 claims description 2
- 230000004044 response Effects 0.000 claims description 2
- 238000005070 sampling Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 6
- 150000002825 nitriles Chemical class 0.000 claims 1
- 238000004293 19F NMR spectroscopy Methods 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 description 116
- 229920003002 synthetic resin Polymers 0.000 description 115
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 100
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 52
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- 238000006243 chemical reaction Methods 0.000 description 37
- 125000001072 heteroaryl group Chemical group 0.000 description 36
- 238000005481 NMR spectroscopy Methods 0.000 description 31
- 238000002360 preparation method Methods 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 125000006413 ring segment Chemical group 0.000 description 29
- 229910052757 nitrogen Inorganic materials 0.000 description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 21
- 125000006239 protecting group Chemical group 0.000 description 21
- 150000001413 amino acids Chemical class 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 20
- 125000000623 heterocyclic group Chemical group 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- 229910052717 sulfur Inorganic materials 0.000 description 20
- 235000001014 amino acid Nutrition 0.000 description 19
- 229940024606 amino acid Drugs 0.000 description 19
- 150000002148 esters Chemical class 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
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- 239000000470 constituent Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 125000002947 alkylene group Chemical group 0.000 description 16
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- 239000000376 reactant Substances 0.000 description 16
- 125000003710 aryl alkyl group Chemical group 0.000 description 15
- 239000000523 sample Substances 0.000 description 15
- 125000004434 sulfur atom Chemical group 0.000 description 15
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
- 238000005859 coupling reaction Methods 0.000 description 13
- 125000000753 cycloalkyl group Chemical group 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 13
- 238000011068 loading method Methods 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 11
- 150000001204 N-oxides Chemical class 0.000 description 11
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 11
- 125000004122 cyclic group Chemical group 0.000 description 11
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 11
- 125000004475 heteroaralkyl group Chemical group 0.000 description 11
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
- 125000003342 alkenyl group Chemical group 0.000 description 10
- 125000000304 alkynyl group Chemical group 0.000 description 10
- 230000008878 coupling Effects 0.000 description 10
- 238000010168 coupling process Methods 0.000 description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 9
- 241000534944 Thia Species 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 102000004196 processed proteins & peptides Human genes 0.000 description 8
- 125000002252 acyl group Chemical group 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 125000004350 aryl cycloalkyl group Chemical group 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 238000012544 monitoring process Methods 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- NXWTWYULZRDBSA-UHFFFAOYSA-N 2-fluoro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1F NXWTWYULZRDBSA-UHFFFAOYSA-N 0.000 description 6
- YPIGHNIIXYSPKF-UHFFFAOYSA-N 3-fluorobenzamide Chemical compound NC(=O)C1=CC=CC(F)=C1 YPIGHNIIXYSPKF-UHFFFAOYSA-N 0.000 description 6
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000004450 alkenylene group Chemical group 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- FTLHGQOBAPTEHE-UHFFFAOYSA-N 2,3,5,6-tetrafluoro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=C(F)C(F)=C(O)C(F)=C1F FTLHGQOBAPTEHE-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000004419 alkynylene group Chemical group 0.000 description 5
- QWCKQJZIFLGMSD-UHFFFAOYSA-N alpha-aminobutyric acid Chemical compound CCC(N)C(O)=O QWCKQJZIFLGMSD-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 5
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 description 5
- 208000014041 isolated anophthalmia-microphthalmia syndrome Diseases 0.000 description 5
- 238000010647 peptide synthesis reaction Methods 0.000 description 5
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- 206010067484 Adverse reaction Diseases 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 230000006838 adverse reaction Effects 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
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- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 125000005544 phthalimido group Chemical group 0.000 description 4
- 238000010532 solid phase synthesis reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- SVOCAUJZDPIIKV-UHFFFAOYSA-N C1N=CN(S1)O Chemical compound C1N=CN(S1)O SVOCAUJZDPIIKV-UHFFFAOYSA-N 0.000 description 3
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 230000003213 activating effect Effects 0.000 description 3
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- 125000000539 amino acid group Chemical group 0.000 description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
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- 238000011161 development Methods 0.000 description 3
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 3
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- 238000006116 polymerization reaction Methods 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 3
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- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
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- OQEBBZSWEGYTPG-UHFFFAOYSA-N 3-aminobutanoic acid Chemical compound CC(N)CC(O)=O OQEBBZSWEGYTPG-UHFFFAOYSA-N 0.000 description 2
- QCHPKSFMDHPSNR-UHFFFAOYSA-N 3-aminoisobutyric acid Chemical compound NCC(C)C(O)=O QCHPKSFMDHPSNR-UHFFFAOYSA-N 0.000 description 2
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- 102100038239 Protein Churchill Human genes 0.000 description 2
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- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
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- 239000003054 catalyst Substances 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
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- 125000000000 cycloalkoxy group Chemical group 0.000 description 2
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- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000006173 tetrahydropyranylmethyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical compound C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N24/00—Investigating or analyzing materials by the use of nuclear magnetic resonance, electron paramagnetic resonance or other spin effects
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/12—Hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/20—Halogenation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/26—Removing halogen atoms or halogen-containing groups from the molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/20—Copolymer characterised by the proportions of the comonomers expressed as weight or mass percentages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2810/00—Chemical modification of a polymer
- C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N24/00—Investigating or analyzing materials by the use of nuclear magnetic resonance, electron paramagnetic resonance or other spin effects
- G01N24/08—Investigating or analyzing materials by the use of nuclear magnetic resonance, electron paramagnetic resonance or other spin effects by using nuclear magnetic resonance
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Pathology (AREA)
- High Energy & Nuclear Physics (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Steroid Compounds (AREA)
- Catalysts (AREA)
- Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1997/023920 WO1998029376A1 (en) | 1996-12-19 | 1997-12-17 | Process for the solid phase synthesis of aldehydes, ketones, oximes, amines and hydroxamic acid compounds |
| US9056398P | 1998-06-24 | 1998-06-24 | |
| US9055898P | 1998-06-24 | 1998-06-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG104614A BG104614A (en) | 2001-10-31 |
| BG65184B1 true BG65184B1 (bg) | 2007-05-31 |
Family
ID=27376603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG104614A BG65184B1 (bg) | 1997-12-17 | 2000-07-14 | Метод и реагенти за количествено определяне на твърдофазовите реакции, използвайки флуорен ямр |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP1044364B8 (enExample) |
| JP (1) | JP2003522934A (enExample) |
| CN (1) | CN1205468C (enExample) |
| AT (1) | ATE364837T1 (enExample) |
| AU (1) | AU748529C (enExample) |
| BG (1) | BG65184B1 (enExample) |
| BR (1) | BR9813701A (enExample) |
| CA (1) | CA2315152A1 (enExample) |
| DE (1) | DE69837936T2 (enExample) |
| DK (1) | DK1044364T3 (enExample) |
| ES (1) | ES2288310T3 (enExample) |
| HU (1) | HUP0200726A2 (enExample) |
| IL (1) | IL136718A0 (enExample) |
| MX (1) | MXPA00006050A (enExample) |
| PL (1) | PL197620B1 (enExample) |
| WO (1) | WO1999031491A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2280272A1 (en) * | 2000-09-27 | 2011-02-02 | Universiteit Leiden | Method for applying NMR for ligand discovery or as a drug screening tool |
| FR2955862B1 (fr) * | 2010-02-02 | 2012-07-13 | Commissariat Energie Atomique | Materiau polymere fluorocarbone et procede de synthese |
| CN103487455B (zh) * | 2013-09-24 | 2016-04-27 | 上海大学 | 一种快速定量检测橄榄油中含羟基化合物的方法 |
| CN108593696B (zh) * | 2018-04-26 | 2020-11-03 | 南京明捷生物医药检测有限公司 | 一种利用定量核磁测定多肽中三氟乙酸残留的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5565324A (en) * | 1992-10-01 | 1996-10-15 | The Trustees Of Columbia University In The City Of New York | Complex combinatorial chemical libraries encoded with tags |
| US5566324A (en) * | 1992-12-24 | 1996-10-15 | Ncr Corporation | Computer apparatus including a main memory prefetch cache and method of operation thereof |
| GB9515070D0 (en) * | 1995-07-22 | 1995-09-20 | Zeneca Ltd | Label |
| US6355490B1 (en) * | 1996-09-13 | 2002-03-12 | Jill Edie Hochlowski | Attached tags for use in combinatorial chemistry synthesis |
-
1998
- 1998-12-14 AU AU25569/99A patent/AU748529C/en not_active Ceased
- 1998-12-14 CA CA002315152A patent/CA2315152A1/en not_active Abandoned
- 1998-12-14 HU HU0200726A patent/HUP0200726A2/hu unknown
- 1998-12-14 DK DK98966876T patent/DK1044364T3/da active
- 1998-12-14 BR BR9813701-8A patent/BR9813701A/pt not_active Application Discontinuation
- 1998-12-14 PL PL341357A patent/PL197620B1/pl not_active IP Right Cessation
- 1998-12-14 MX MXPA00006050A patent/MXPA00006050A/es active IP Right Grant
- 1998-12-14 WO PCT/US1998/026512 patent/WO1999031491A1/en not_active Ceased
- 1998-12-14 AT AT98966876T patent/ATE364837T1/de not_active IP Right Cessation
- 1998-12-14 CN CNB988133334A patent/CN1205468C/zh not_active Expired - Fee Related
- 1998-12-14 ES ES98966876T patent/ES2288310T3/es not_active Expired - Lifetime
- 1998-12-14 IL IL13671898A patent/IL136718A0/xx active IP Right Grant
- 1998-12-14 DE DE69837936T patent/DE69837936T2/de not_active Expired - Lifetime
- 1998-12-14 EP EP98966876A patent/EP1044364B8/en not_active Expired - Lifetime
- 1998-12-14 JP JP2000539340A patent/JP2003522934A/ja active Pending
-
2000
- 2000-07-14 BG BG104614A patent/BG65184B1/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL197620B1 (pl) | 2008-04-30 |
| EP1044364A1 (en) | 2000-10-18 |
| PL341357A1 (en) | 2001-04-09 |
| BG104614A (en) | 2001-10-31 |
| WO1999031491A1 (en) | 1999-06-24 |
| DE69837936D1 (de) | 2007-07-26 |
| CN1205468C (zh) | 2005-06-08 |
| AU748529C (en) | 2002-10-17 |
| MXPA00006050A (es) | 2004-05-21 |
| DK1044364T3 (da) | 2007-09-24 |
| BR9813701A (pt) | 2000-12-12 |
| EP1044364B1 (en) | 2007-06-13 |
| CN1284165A (zh) | 2001-02-14 |
| ES2288310T3 (es) | 2008-01-01 |
| DE69837936T2 (de) | 2008-02-28 |
| IL136718A0 (en) | 2001-06-14 |
| AU748529B2 (en) | 2002-06-06 |
| ATE364837T1 (de) | 2007-07-15 |
| HUP0200726A2 (en) | 2002-06-29 |
| AU2556999A (en) | 1999-07-05 |
| EP1044364B8 (en) | 2008-01-02 |
| JP2003522934A (ja) | 2003-07-29 |
| EP1044364A4 (en) | 2004-10-06 |
| CA2315152A1 (en) | 1999-06-24 |
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