CA1137981A - 6-(.omega.-AMINOALKYL)-9-(2'3'-O-ISOPROPYLIDENE- .beta.-D-RIBOFURANOSYL)PURINES - Google Patents

6-(.omega.-AMINOALKYL)-9-(2'3'-O-ISOPROPYLIDENE- .beta.-D-RIBOFURANOSYL)PURINES

Info

Publication number: CA1137981A
Authority: CA; Canada
Prior art keywords: ligand; solution; purine; amino; binding
Prior art date: 1978-06-22
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.): Expired

Application number

CA000390187A

Other languages

English (en)

Inventor

Robert J. Carrico

Richard D. Johnson

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.)

Bayer Corp

Original Assignee

Miles Laboratories Inc

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.)

1978-06-22

Filing date

1981-11-16

Publication date

1982-12-21

1978-06-22 Priority claimed from US05/917,962 external-priority patent/US4171432A/en

1978-10-12 Priority claimed from US05/950,858 external-priority patent/US4213893A/en

1979-06-21 Priority claimed from CA330,232A external-priority patent/CA1128883A/fr

1981-11-16 Application filed by Miles Laboratories Inc filed Critical Miles Laboratories Inc

1981-11-16 Priority to CA000390187A priority Critical patent/CA1137981A/fr

1982-12-21 Application granted granted Critical

1982-12-21 Publication of CA1137981A publication Critical patent/CA1137981A/fr

Status Expired legal-status Critical Current

Links

150000003212 purines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 8
239000000543 intermediate Substances 0.000 abstract description 33
238000000159 protein binding assay Methods 0.000 abstract description 22
230000009870 specific binding Effects 0.000 abstract description 13
238000002360 preparation method Methods 0.000 abstract description 10
AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 abstract description 5
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 abstract 1
229930024421 Adenine Natural products 0.000 abstract 1
229960000643 adenine Drugs 0.000 abstract 1
239000002773 nucleotide Substances 0.000 abstract 1
125000003729 nucleotide group Chemical group 0.000 abstract 1
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 52
239000003446 ligand Substances 0.000 description 49
239000000243 solution Substances 0.000 description 45
239000000562 conjugate Substances 0.000 description 39
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
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VWWQXMAJTJZDQX-UYBVJOGSSA-N flavin adenine dinucleotide Chemical compound C1=NC2=C(N)N=CN=C2N1[C@@H]([C@H](O)[C@@H]1O)O[C@@H]1CO[P@](O)(=O)O[P@@](O)(=O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C2=NC(=O)NC(=O)C2=NC2=C1C=C(C)C(C)=C2 VWWQXMAJTJZDQX-UYBVJOGSSA-N 0.000 description 31
235000019162 flavin adenine dinucleotide Nutrition 0.000 description 30
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VSWSDTLXDWESGZ-AWEZNQCLSA-N (2s)-3-[4-(4-hydroxyphenoxy)phenyl]-2-(iodoamino)propanoic acid Chemical compound C1=CC(C[C@@H](C(=O)O)NI)=CC=C1OC1=CC=C(O)C=C1 VSWSDTLXDWESGZ-AWEZNQCLSA-N 0.000 description 25
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DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 7
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FVTCRASFADXXNN-SCRDCRAPSA-N flavin mononucleotide Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-SCRDCRAPSA-N 0.000 description 7
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ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
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XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 6
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125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 5
239000002126 C01EB10 - Adenosine Substances 0.000 description 5
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
AUYYCJSJGJYCDS-LBPRGKRZSA-N Thyrolar Chemical compound IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-LBPRGKRZSA-N 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 5
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UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 5
238000006482 condensation reaction Methods 0.000 description 5
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229910052740 iodine Inorganic materials 0.000 description 5
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RLFWWDJHLFCNIJ-UHFFFAOYSA-N 4-aminoantipyrine Chemical compound CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 4
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WRLGYAWRGXKSKG-UHFFFAOYSA-M phenobarbital sodium Chemical compound [Na+].C=1C=CC=CC=1C1(CC)C(=O)NC([O-])=NC1=O WRLGYAWRGXKSKG-UHFFFAOYSA-M 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
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150000003138 primary alcohols Chemical class 0.000 description 1
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
229960002393 primidone Drugs 0.000 description 1
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239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
229930002534 steroid glycoside Natural products 0.000 description 1
239000000758 substrate Substances 0.000 description 1
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238000012360 testing method Methods 0.000 description 1
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150000003515 testosterones Chemical class 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 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
MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
229960000604 valproic acid Drugs 0.000 description 1
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235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1
230000036642 wellbeing Effects 0.000 description 1
210000002268 wool Anatomy 0.000 description 1

Landscapes

Saccharide Compounds (AREA)

CA000390187A 1978-06-22 1981-11-16 6-(.omega.-AMINOALKYL)-9-(2'3'-O-ISOPROPYLIDENE- .beta.-D-RIBOFURANOSYL)PURINES Expired CA1137981A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000390187A CA1137981A (fr)	1978-06-22	1981-11-16	6-(.omega.-AMINOALKYL)-9-(2'3'-O-ISOPROPYLIDENE- .beta.-D-RIBOFURANOSYL)PURINES

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US05/917,962 US4171432A (en)	1978-06-22	1978-06-22	Flavin adenine dinucleotide-iodothyronine conjugates
US05/950,858 US4213893A (en)	1978-10-12	1978-10-12	Flavin adenine dinucleotide-labeled conjugates for use in specific binding assays
US950,858		1978-10-12
CA330,232A CA1128883A (fr)	1978-06-22	1979-06-21	Conjugats de flavine-adenine-dinucleotide marques utilises dans les epreuves de fixation
CA000390187A CA1137981A (fr)	1978-06-22	1981-11-16	6-(.omega.-AMINOALKYL)-9-(2'3'-O-ISOPROPYLIDENE- .beta.-D-RIBOFURANOSYL)PURINES
US917,962		1986-10-14

Publications (1)

Publication Number	Publication Date
CA1137981A true CA1137981A (fr)	1982-12-21

Family

ID=27426158

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000390187A Expired CA1137981A (fr)	1978-06-22	1981-11-16	6-(.omega.-AMINOALKYL)-9-(2'3'-O-ISOPROPYLIDENE- .beta.-D-RIBOFURANOSYL)PURINES

Country Status (1)

Country	Link
CA (1)	CA1137981A (fr)

1981
- 1981-11-16 CA CA000390187A patent/CA1137981A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-12-21	MKEX	Expiry
2023-05-26	MKEX	Expiry	Effective date: 19991221

Publication	Publication Date	Title
US4213893A (en)	1980-07-22	Flavin adenine dinucleotide-labeled conjugates for use in specific binding assays
US4331590A (en)	1982-05-25	β-Galactosyl-umbelliferone-labeled protein and polypeptide conjugates
US4279992A (en)	1981-07-21	Specific binding assay employing an enzyme-cleavable substrate as label
US4404366A (en)	1983-09-13	Beta-galactosyl-umbelliferone-labeled hapten conjugates
CA1210758A (fr)	1986-09-02	Derives de n-aminoalkyl iodothyronine, immunogenes et anticorps
CA1213579A (fr)	1986-11-04	Digoxigenine immunogene, anticorps, conjugats marques, et derives
US5595741A (en)	1997-01-21	Aminoalkylmaleimides and hapten and antigen derivatives derived therefrom as well as conjugates with peptides or proteins
US4533493A (en)	1985-08-06	Theophylline immunogens, antibodies, labeled conjugates, and related derivatives
US4495281A (en)	1985-01-22	Tricyclic antidepressant drug immunogens, antibodies, labeled conjugates, and related derivatives
EP0357869A1 (fr)	1990-03-14	Essai à l'aide de substances d'affinité comprenant une étape à base de chromatographie liquide à haute pression
GB2041922A (en)	1980-09-17	Intermediates useful in the synthesis of chemiluminescent- labeled conjugates for use in specific binding assays
Van Vunakis et al.	1974	Radioimmunoassays for adriamycin and daunomycin
GB2026159A (en)	1980-01-30	Chemiluminescent phthalhydrazide-labelled conjugates
CA1152491A (fr)	1983-08-23	Conjugues de proteine et de polypeptide marques a la flavine-adenine-dinucleotide
US4255566A (en)	1981-03-10	Flavin adenine dinucleotide derivatives and labeled conjugates prepared therefrom
US4225485A (en)	1980-09-30	Chemiluminescent naphthalene-1,2-dicarboxylic acid hydrazide-labeled polypeptides and proteins
CA1250099A (fr)	1989-02-14	Immunogenes, anticorps, conjugats marques et derives apparentes contre la lidocaine et ses analogues
US4261893A (en)	1981-04-14	Bis-phthalimide intermediates
CA1128883A (fr)	1982-08-03	Conjugats de flavine-adenine-dinucleotide marques utilises dans les epreuves de fixation
US4608336A (en)	1986-08-26	#3B theophylline immunoassay employing 9-theophylline reagents
US4171432A (en)	1979-10-16	Flavin adenine dinucleotide-iodothyronine conjugates
CH659713A5 (de)	1987-02-13	Spezifisches bindungs-testverfahren und reagenszusammensetzung zur durchfuehrung dieses verfahrens.
US4297273A (en)	1981-10-27	Chemiluminescent phthalhydrazide-labeled protein and polypeptide conjugates
US4460772A (en)	1984-07-17	6-[N-(ω-Carboxyalkyl)amino]-1,3-dimethyl-5-formamidouracils
CA1139303A (fr)	1983-01-11	Conjugues marques aux dinucleotides flavine-adenine pour tests a liaison specifique