NL8702007A - Nieuwe met tritium gemerkte verbinding, haar bereiding en haar toepassing in het bijzonder bij de bepaling van de affiniteit van de retinoiden voor hun celreceptor. - Google Patents

Nieuwe met tritium gemerkte verbinding, haar bereiding en haar toepassing in het bijzonder bij de bepaling van de affiniteit van de retinoiden voor hun celreceptor. Download PDF

Info

Publication number: NL8702007A
Authority: NL; Netherlands
Prior art keywords: tritium; tetrahydro; tetramethyl; naphthyl; benzo
Prior art date: 1986-08-29

Application number

NL8702007A

Other languages

English (en)

Dutch (nl)

Original Assignee

Cird

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.)

1986-08-29

Filing date

1987-08-27

Publication date

1988-03-16

1987-08-27 Application filed by Cird filed Critical Cird

1988-03-16 Publication of NL8702007A publication Critical patent/NL8702007A/nl

Links

150000001875 compounds Chemical class 0.000 title description 22
238000002360 preparation method Methods 0.000 title description 3
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 31
229910052722 tritium Inorganic materials 0.000 claims description 31
230000002285 radioactive effect Effects 0.000 claims description 25
238000000034 method Methods 0.000 claims description 15
239000000047 product Substances 0.000 claims description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
230000009471 action Effects 0.000 claims description 8
QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 6
239000003550 marker Substances 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
VYBLDUKQAWIMMM-UHFFFAOYSA-N 2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1-benzothiophene-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2SC(C=3C=C4C(C)(C)CCC(C4=CC=3)(C)C)=CC2=C1 VYBLDUKQAWIMMM-UHFFFAOYSA-N 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
230000000694 effects Effects 0.000 claims description 5
-1 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl Chemical group 0.000 claims description 4
239000003638 chemical reducing agent Substances 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
230000002140 halogenating effect Effects 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
239000013067 intermediate product Substances 0.000 claims description 2
238000002372 labelling Methods 0.000 claims description 2
229910052697 platinum Inorganic materials 0.000 claims description 2
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 2
101100300786 Xenopus laevis crabp2 gene Proteins 0.000 claims 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000003446 ligand Substances 0.000 description 46
101001099854 Xenopus laevis Cellular retinoic acid-binding protein 2 Proteins 0.000 description 13
SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 12
229930002330 retinoic acid Natural products 0.000 description 12
229960001727 tretinoin Drugs 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 8
210000004027 cell Anatomy 0.000 description 6
229940126062 Compound A Drugs 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000010494 dissociation reaction Methods 0.000 description 3
230000005593 dissociations Effects 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000010828 elution Methods 0.000 description 2
230000007717 exclusion Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
230000035755 proliferation Effects 0.000 description 2
238000011002 quantification Methods 0.000 description 2
239000012217 radiopharmaceutical Substances 0.000 description 2
229940121896 radiopharmaceutical Drugs 0.000 description 2
230000002799 radiopharmaceutical effect Effects 0.000 description 2
230000002441 reversible effect Effects 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VWSAPEXODLCNSQ-UHFFFAOYSA-N 2-(3-bromo-5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1-benzothiophene-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2SC(C=3C=C4C(C)(C)CCC(C4=CC=3Br)(C)C)=CC2=C1 VWSAPEXODLCNSQ-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
230000024245 cell differentiation Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000003831 deregulation Effects 0.000 description 1
230000004069 differentiation Effects 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
210000001339 epidermal cell Anatomy 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000008316 intracellular mechanism Effects 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
238000012417 linear regression Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000006303 photolysis reaction Methods 0.000 description 1
230000015843 photosynthesis, light reaction Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000003608 radiolysis reaction Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
210000001550 testis Anatomy 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Investigating Or Analysing Biological Materials (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Peptides Or Proteins (AREA)

NL8702007A 1986-08-29 1987-08-27 Nieuwe met tritium gemerkte verbinding, haar bereiding en haar toepassing in het bijzonder bij de bepaling van de affiniteit van de retinoiden voor hun celreceptor. NL8702007A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR8612237A FR2603280B1 (fr)	1986-08-29	1986-08-29	Nouveau compose marque au tritium, sa preparation et son application notamment dans la determination de l'affinite des retinoides pour leur recepteur cellulaire
FR8612237		1986-08-29

Publications (1)

Publication Number	Publication Date
NL8702007A true NL8702007A (nl)	1988-03-16

Family

ID=9338587

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8702007A NL8702007A (nl)	1986-08-29	1987-08-27	Nieuwe met tritium gemerkte verbinding, haar bereiding en haar toepassing in het bijzonder bij de bepaling van de affiniteit van de retinoiden voor hun celreceptor.

Country Status (11)

Country	Link
US (1)	US4880941A (fr)
JP (1)	JPS63152376A (fr)
BE (1)	BE1004153A3 (fr)
CA (1)	CA1293733C (fr)
CH (1)	CH673028A5 (fr)
DE (1)	DE3728810C2 (fr)
FR (1)	FR2603280B1 (fr)
GB (1)	GB2194535B (fr)
IT (1)	IT1228949B (fr)
NL (1)	NL8702007A (fr)
SE (1)	SE463714B (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2635683B1 (fr) *	1988-09-01	1990-11-09	Cird	Nouveau compose marque au tritium, sa preparation et son application notamment dans la determination de l'affinite des retinoides pour leurs recepteurs nucleaires et leur proteine de liaison cytosolique
FR2649976B1 (fr) *	1989-07-20	1991-09-27	Cird	Nouveau compose marque au tritium, sa preparation et son application notamment dans le reperage des recepteurs nucleaires des retinoides
US5149631A (en) *	1989-07-20	1992-09-22	Centre International De Recherches Dermatologiques Galderma (Cird Galderma)	Compound marked with tritium, its preparation and its use in the location of nuclear receptors of retinoids
ES2152920T3 (es) *	1990-02-09	2001-02-16	Salk Inst For Biological Studi	Composiciones receptoras de retinoides y metodos.
US5688691A (en) *	1990-03-22	1997-11-18	The Salk Institute For Biological Studies	Insect retinoid-like receptor compositions and methods
US5508456A (en) *	1993-07-30	1996-04-16	Ligand Pharmaceuticals Incorporated	9-cis tritium-labeled retinoids and intermediates, methods for their synthesis and methods for their use in discovering retinoid X receptor ligands
WO1995011217A1 (fr) *	1993-10-22	1995-04-27	Ligand Pharmaceuticals Incorporated	Retinoides marques aux isotopes, leur methode de synthese et leur utilisation
TW200404054A (en) *	2002-07-26	2004-03-16	Wako Pure Chem Ind Ltd	Method for deuteration of aromatic ring
TW200413273A (en) *	2002-11-15	2004-08-01	Wako Pure Chem Ind Ltd	Heavy hydrogenation method of heterocyclic rings
TW200413274A (en) *	2002-12-27	2004-08-01	Wako Pure Chem Ind Ltd	Deuteration or tritiation method
KR20060129284A (ko) *	2004-01-23	2006-12-15	와코 쥰야꾸 고교 가부시키가이샤	혼합촉매를 사용한 중수소화방법
GB201517745D0 (en) *	2015-10-07	2015-11-18	Johnson Matthey Plc	Method of monitoring a parameter of a hydrocarbon well, pipeline or formation

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3142975A1 (de) *	1981-10-29	1983-05-11	Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V., 3400 Göttingen	Verfahren zur herstellung von mit tritium markierterretinsaeure
LU85544A1 (fr) *	1984-09-19	1986-04-03	Cird	Derives heterocycliques aromatiques,leur procede de preparation et leur application dans les domaines therapeutique et cosmetique

1986
- 1986-08-29 FR FR8612237A patent/FR2603280B1/fr not_active Expired
1987
- 1987-08-27 CH CH3293/87A patent/CH673028A5/fr not_active IP Right Cessation
- 1987-08-27 NL NL8702007A patent/NL8702007A/nl not_active Application Discontinuation
- 1987-08-28 SE SE8703336A patent/SE463714B/sv not_active IP Right Cessation
- 1987-08-28 DE DE3728810A patent/DE3728810C2/de not_active Expired - Fee Related
- 1987-08-28 JP JP62213178A patent/JPS63152376A/ja active Pending
- 1987-08-28 GB GB8720397A patent/GB2194535B/en not_active Expired - Lifetime
- 1987-08-28 CA CA000545638A patent/CA1293733C/fr not_active Expired - Lifetime
- 1987-08-28 IT IT8721749A patent/IT1228949B/it active
- 1987-08-28 BE BE8700957A patent/BE1004153A3/fr not_active IP Right Cessation
- 1987-08-28 US US07/090,324 patent/US4880941A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
GB2194535A (en)	1988-03-09
IT1228949B (it)	1991-07-10
BE1004153A3 (fr)	1992-10-06
US4880941A (en)	1989-11-14
JPS63152376A (ja)	1988-06-24
FR2603280A1 (fr)	1988-03-04
CH673028A5 (fr)	1990-01-31
DE3728810C2 (de)	1998-02-26
SE463714B (sv)	1991-01-14
SE8703336D0 (sv)	1987-08-28
GB2194535B (en)	1990-03-21
FR2603280B1 (fr)	1988-10-28
IT8721749A0 (it)	1987-08-28
SE8703336L (sv)	1988-03-01
GB8720397D0 (en)	1987-10-07
DE3728810A1 (de)	1988-03-03
CA1293733C (fr)	1991-12-31

Legal Events

Date	Code	Title	Description
1994-10-03	BV	The patent application has lapsed

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Auberson et al.	2017	Improving nonspecific binding and solubility: bicycloalkyl groups and cubanes as para‐phenyl bioisosteres
Lewis et al.	1980	Identification of the C (6)-S-conjugate of leukotriene A with cysteine as a naturally occurring slow reacting substance of anaphylaxis (SRS-A). Importance of the 11-cis-geometry for biological activity
Hall et al.	1997	Autoradiographic localization of 5-HT1A receptors in the post-mortem human brain using [3H] WAY-100635 and [11C] way-100635
NL8702007A (nl)	1988-03-16	Nieuwe met tritium gemerkte verbinding, haar bereiding en haar toepassing in het bijzonder bij de bepaling van de affiniteit van de retinoiden voor hun celreceptor.
US5196577A (en)	1993-03-23	Compound marked with tritium, its preparation and its use in particular in the determination of the affinity of retinoids for their nuclear receptors and their cytosolic binding protein
Bigott et al.	2005	Design and synthesis of functionalized cyclopentadienyl tricarbonylmetal complexes for technetium-94m PET imaging of estrogen receptors
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EP0409740B1 (fr)	1993-11-03	Nouveau composé marqué au tritium, sa préparation et son application, notamment dans le repérage des récepteurs nucléaires des rétinoides
Ali et al.	1993	Synthesis of A-ring fluorinated derivatives of (17a, 20E/Z)-[125I] iodovinylestradiols: effect on receptor binding and receptormediated target tissue uptake
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Billault et al.	2022	Advanced methodology combining UPLC-MS, isotopic labelling and H/D exchanges reveals three tyrosine-tyrosine cross-links induced by oxidative radicals evolving to at least four dimeric structures
Kedderis et al.	1994	Chemical characterization and disposition studies with 1, 2, 7, 8‐tetrabromodibenzofuran in the rat
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TANAKA et al.	1976	Analytical Studies on Mepirizole and Its Metabolites. IV. Quantitative Determination of Mepirizole in Human Serum by Mass Fragmentography, and Isotope Effect on Drug Metabolism
Timmers et al.	1990	A rapid versatile microassay for cellular retinol-binding protein using Lipidex-1000 microcolumns.
Sani et al.	1990	Biologically active aromatic retinoids bearing azido photoaffinity-labeling groups and their binding to cellular retinoic acid-binding protein
Bobik et al.	1977	The preparation and purification of 3–(4‐iodophenoxy)‐1‐isopropylamino‐2‐propanol‐125I, a beta adrenergic antagonist
Singer et al.	1985	Chlorthalidone
Zeitler et al.	1978	Improved Preparation and Structural Elucidation of the Tryptophan Cleavage Reagent 2-(2′-Nitro-phenylsulfenyl)-3-methyl-3-bromoindolenine (BNPS-skatole)
Dawson et al.	1985	Conformational restrictions of the retinoid skeleton
Burns et al.	1982	The preparation of carbon‐14 and tritium labelled 1‐[4‐(2‐dimethylaminoethoxy) phenyl]‐1, 2‐diphenyl‐1‐butene [ICI 46,474, tamoxifen (nolvadex)] and the separation of cis‐trans isomers 2. The synthesis of tritium labelled tamoxifen (nolvadex)