CA2027022A1 - Composes utiles pour la mesure de faibles concentrations de sulfonyluree par une methode immunologique - Google Patents

Composes utiles pour la mesure de faibles concentrations de sulfonyluree par une methode immunologique

Info

Publication number: CA2027022A1
Authority: CA; Canada
Prior art keywords: alkyl; sulfonylurea; conjugate; alkoxy; haloalkoxy
Prior art date: 1989-10-06
Legal status (The legal status 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 status listed.): Abandoned

Application number

CA 2027022

Other languages

English (en)

Inventor

Bruce L. Finkelstein

Janice K. Sharp

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

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.)

1989-10-06

Filing date

1990-10-05

Publication date

1991-04-07

1990-10-05 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1991-04-07 Publication of CA2027022A1 publication Critical patent/CA2027022A1/fr

Status Abandoned legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 63
229940100389 Sulfonylurea Drugs 0.000 title claims abstract description 48
238000003018 immunoassay Methods 0.000 title abstract description 9
102000004169 proteins and genes Human genes 0.000 claims abstract description 48
108090000623 proteins and genes Proteins 0.000 claims abstract description 48
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims abstract description 37
-1 Sulfonylurea carboxylic acids Chemical class 0.000 claims abstract description 19
238000002965 ELISA Methods 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 65
125000000217 alkyl group Chemical group 0.000 claims description 55
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 53
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 50
239000011248 coating agent Substances 0.000 claims description 33
238000000576 coating method Methods 0.000 claims description 33
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
125000003545 alkoxy group Chemical group 0.000 claims description 18
108010058846 Ovalbumin Proteins 0.000 claims description 17
125000004438 haloalkoxy group Chemical group 0.000 claims description 17
229940092253 ovalbumin Drugs 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 16
108010045069 keyhole-limpet hemocyanin Proteins 0.000 claims description 16
150000002367 halogens Chemical class 0.000 claims description 15
238000003556 assay Methods 0.000 claims description 13
102000006395 Globulins Human genes 0.000 claims description 12
108010044091 Globulins Proteins 0.000 claims description 12
125000001188 haloalkyl group Chemical group 0.000 claims description 12
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 11
230000002163 immunogen Effects 0.000 claims description 11
239000005496 Chlorsulfuron Substances 0.000 claims description 10
229910052717 sulfur Inorganic materials 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 9
108091003079 Bovine Serum Albumin Proteins 0.000 claims description 8
229940098773 bovine serum albumin Drugs 0.000 claims description 8
241000408747 Lepomis gibbosus Species 0.000 claims description 7
VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
235000020236 pumpkin seed Nutrition 0.000 claims description 7
239000007790 solid phase Substances 0.000 claims description 7
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000004995 haloalkylthio group Chemical group 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000005472 Bensulfuron methyl Substances 0.000 claims description 5
244000025254 Cannabis sativa Species 0.000 claims description 5
235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 claims description 5
235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 claims description 5
241000283973 Oryctolagus cuniculus Species 0.000 claims description 5
XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical group COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 claims description 5
125000004966 cyanoalkyl group Chemical group 0.000 claims description 5
239000005584 Metsulfuron-methyl Substances 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 3
125000005108 alkenylthio group Chemical group 0.000 claims description 3
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
NSWAMPCUPHPTTC-UHFFFAOYSA-N chlorimuron-ethyl Chemical group CCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 NSWAMPCUPHPTTC-UHFFFAOYSA-N 0.000 claims description 3
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
229910052705 radium Inorganic materials 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
238000012360 testing method Methods 0.000 claims description 3
229940127121 immunoconjugate Drugs 0.000 claims description 2
230000006872 improvement Effects 0.000 claims description 2
125000005083 alkoxyalkoxy group Chemical group 0.000 claims 6
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
125000003831 tetrazolyl group Chemical group 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 1
230000000536 complexating effect Effects 0.000 claims 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
230000004044 response Effects 0.000 abstract description 5
239000004009 herbicide Substances 0.000 abstract 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 45
239000000243 solution Substances 0.000 description 43
235000018102 proteins Nutrition 0.000 description 38
239000002253 acid Substances 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 21
239000000523 sample Substances 0.000 description 21
230000015572 biosynthetic process Effects 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
239000007787 solid Substances 0.000 description 16
238000003786 synthesis reaction Methods 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
239000012491 analyte Substances 0.000 description 14
239000000427 antigen Substances 0.000 description 14
102000036639 antigens Human genes 0.000 description 14
108091007433 antigens Proteins 0.000 description 14
229940124530 sulfonamide Drugs 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
150000003456 sulfonamides Chemical class 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
230000004913 activation Effects 0.000 description 11
150000001412 amines Chemical class 0.000 description 11
239000000872 buffer Substances 0.000 description 11
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
239000000463 material Substances 0.000 description 10
239000000575 pesticide Substances 0.000 description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
229910052739 hydrogen Inorganic materials 0.000 description 9
125000003588 lysine group Chemical class [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 9
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 9
239000002671 adjuvant Substances 0.000 description 8
229940125773 compound 10 Drugs 0.000 description 8
238000005859 coupling reaction Methods 0.000 description 8
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000010790 dilution Methods 0.000 description 7
239000012895 dilution Substances 0.000 description 7
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 7
239000002953 phosphate buffered saline Substances 0.000 description 7
239000002689 soil Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 6
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
230000008878 coupling Effects 0.000 description 6
238000010168 coupling process Methods 0.000 description 6
235000018977 lysine Nutrition 0.000 description 6
239000000758 substrate Substances 0.000 description 6
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
125000003277 amino group Chemical group 0.000 description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 description 5
229940125904 compound 1 Drugs 0.000 description 5
229940125797 compound 12 Drugs 0.000 description 5
238000001514 detection method Methods 0.000 description 5
230000003053 immunization Effects 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
239000011593 sulfur Substances 0.000 description 5
102000014914 Carrier Proteins Human genes 0.000 description 4
108010078791 Carrier Proteins Proteins 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
108090000790 Enzymes Proteins 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
230000008859 change Effects 0.000 description 4
229940088598 enzyme Drugs 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000002649 immunization Methods 0.000 description 4
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
230000008569 process Effects 0.000 description 4
150000003335 secondary amines Chemical class 0.000 description 4
238000001179 sorption measurement Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
239000003039 volatile agent Substances 0.000 description 4
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 3
108700000434 Cannabis sativa edestin Proteins 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
241000124008 Mammalia Species 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
239000004793 Polystyrene Substances 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000000890 antigenic effect Effects 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
239000002585 base Substances 0.000 description 3
230000021615 conjugation Effects 0.000 description 3
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
235000013305 food Nutrition 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
239000011521 glass Substances 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
230000028993 immune response Effects 0.000 description 3
210000000987 immune system Anatomy 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
238000003760 magnetic stirring Methods 0.000 description 3
238000005259 measurement Methods 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
238000011587 new zealand white rabbit Methods 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000008363 phosphate buffer Substances 0.000 description 3
229920002223 polystyrene Polymers 0.000 description 3
150000003141 primary amines Chemical class 0.000 description 3
239000012266 salt solution Substances 0.000 description 3
UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000283690 Bos taurus Species 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
241000283707 Capra Species 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
238000002835 absorbance Methods 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000003213 activating effect Effects 0.000 description 2
235000001014 amino acid Nutrition 0.000 description 2
229940024606 amino acid Drugs 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000003125 aqueous solvent Substances 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
230000000903 blocking effect Effects 0.000 description 2
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210000004027 cell Anatomy 0.000 description 2
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238000005660 chlorination reaction Methods 0.000 description 2
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ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
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239000008367 deionised water Substances 0.000 description 2
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238000001914 filtration Methods 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 2
230000008611 intercellular interaction Effects 0.000 description 2
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
KJYKABTWCXRMTA-UHFFFAOYSA-N phenyl n-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamate Chemical compound COC1=NC(C)=NC(NC(=O)OC=2C=CC=CC=2)=N1 KJYKABTWCXRMTA-UHFFFAOYSA-N 0.000 description 2
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LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000011550 stock solution Substances 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
125000003396 thiol group Chemical class [H]S* 0.000 description 2
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 2
SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 2
NKUZQMZWTZAPSN-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2-bromoacetate Chemical compound BrCC(=O)ON1C(=O)CCC1=O NKUZQMZWTZAPSN-UHFFFAOYSA-N 0.000 description 1
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HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 1
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CA 2027022 1989-10-06 1990-10-05 Composes utiles pour la mesure de faibles concentrations de sulfonyluree par une methode immunologique Abandoned CA2027022A1 (fr)

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Application Number	Priority Date	Filing Date
US41840489A	1989-10-06	1989-10-06
US418,404		1989-10-06
US56967290A	1990-08-22	1990-08-22
US569,672		1990-08-22

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CA2027022A1 true CA2027022A1 (fr)	1991-04-07

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CA 2027022 Abandoned CA2027022A1 (fr)	1989-10-06	1990-10-05	Composes utiles pour la mesure de faibles concentrations de sulfonyluree par une methode immunologique

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7521473B2 (en)	2004-02-25	2009-04-21	Wyeth	Inhibitors of protein tyrosine phosphatase 1B

1990
- 1990-10-05 CA CA 2027022 patent/CA2027022A1/fr not_active Abandoned

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7521473B2 (en)	2004-02-25	2009-04-21	Wyeth	Inhibitors of protein tyrosine phosphatase 1B

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US5830770A (en)	1998-11-03	Hapten-protein conjugates for use in detection of organophosphorus compounds
CA2027022A1 (fr)	1991-04-07	Composes utiles pour la mesure de faibles concentrations de sulfonyluree par une methode immunologique
WO1991004967A1 (fr)	1991-04-18	Composes utiles pour mesurer de faibles taux de sulfonylurees par analyse immunologique
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US12163955B2 (en)	2024-12-10	Antibodies to methotrexate and uses thereof
CA1273572A (fr)	1990-09-04	Preparation d'anticorps, procede de fabrication et application
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1994-04-05	FZDE	Dead

CA2027022A1 - Composes utiles pour la mesure de faibles concentrations de sulfonyluree par une methode immunologique - Google Patents

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