DE10302787A1 - Hydrophile, Thiol-reaktive Cyaninfarbstoffe und deren Konjugate mit Biomolekülen für die Fluoreszenzdiagnostik - Google Patents

Hydrophile, Thiol-reaktive Cyaninfarbstoffe und deren Konjugate mit Biomolekülen für die Fluoreszenzdiagnostik Download PDF

Info

Publication number: DE10302787A1
Authority: DE; Germany
Prior art keywords: solvates; formula; salts; compound; dye according
Prior art date: 2003-01-24
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.): Ceased

Application number

DE2003102787

Other languages

German (de)

English (en)

Inventor

Kai Licha

Christine Perlitz

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 Pharma AG

Original Assignee

Schering AG

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.)

2003-01-24

Filing date

2003-01-24

Publication date

2004-08-12

2003-01-24 Application filed by Schering AG filed Critical Schering AG

2003-01-24 Priority to DE2003102787 priority Critical patent/DE10302787A1/de

2003-11-14 Priority to AT03767544T priority patent/ATE409209T1/de

2003-11-14 Priority to UAA200508207A priority patent/UA82684C2/uk

2003-11-14 Priority to PL03376459A priority patent/PL376459A1/xx

2003-11-14 Priority to EA200501064A priority patent/EA009386B1/ru

2003-11-14 Priority to KR1020057013493A priority patent/KR20050103907A/ko

2003-11-14 Priority to MXPA05007668A priority patent/MXPA05007668A/es

2003-11-14 Priority to JP2004566758A priority patent/JP2006513293A/ja

2003-11-14 Priority to YUP-2005/0561A priority patent/RS20050561A/sr

2003-11-14 Priority to NZ541414A priority patent/NZ541414A/en

2003-11-14 Priority to CN 200380109197 priority patent/CN1742057A/zh

2003-11-14 Priority to BR0318028-0A priority patent/BR0318028A/pt

2003-11-14 Priority to AU2003292019A priority patent/AU2003292019A1/en

2003-11-14 Priority to PCT/EP2003/012735 priority patent/WO2004065491A1/en

2003-11-14 Priority to CA002514131A priority patent/CA2514131A1/en

2003-11-14 Priority to ES03767544T priority patent/ES2311736T3/es

2003-11-14 Priority to DE60323766T priority patent/DE60323766D1/de

2003-11-14 Priority to EP03767544A priority patent/EP1585791B1/en

2004-01-23 Priority to US10/762,582 priority patent/US20040260072A1/en

2004-08-12 Publication of DE10302787A1 publication Critical patent/DE10302787A1/de

2005-07-28 Priority to CR7925A priority patent/CR7925A/es

2005-08-23 Priority to ZA200506759A priority patent/ZA200506759B/en

2005-08-23 Priority to EC2005005975A priority patent/ECSP055975A/es

2005-08-23 Priority to NO20053919A priority patent/NO20053919L/no

Status Ceased legal-status Critical Current

Links

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AHRDYPOLCRKVMP-UHFFFAOYSA-N tert-butyl 3-pyridin-4-ylpropanoate Chemical compound CC(C)(C)OC(=O)CCC1=CC=NC=C1 AHRDYPOLCRKVMP-UHFFFAOYSA-N 0.000 description 2
VWSUFGICWVWBCL-UHFFFAOYSA-N tert-butyl 5-pyridin-4-ylpentanoate Chemical compound CC(C)(C)OC(=O)CCCCC1=CC=NC=C1 VWSUFGICWVWBCL-UHFFFAOYSA-N 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
UYNSYFDLTSSUNI-UHFFFAOYSA-N tert-butyl n-(2-aminopropyl)carbamate Chemical compound CC(N)CNC(=O)OC(C)(C)C UYNSYFDLTSSUNI-UHFFFAOYSA-N 0.000 description 2
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
239000012581 transferrin Substances 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
PVGATNRYUYNBHO-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 4-(2,5-dioxopyrrol-1-yl)butanoate Chemical class O=C1CCC(=O)N1OC(=O)CCCN1C(=O)C=CC1=O PVGATNRYUYNBHO-UHFFFAOYSA-N 0.000 description 1
AWNXKZVIZARMME-UHFFFAOYSA-N 1-[[5-[2-[(2-chloropyridin-4-yl)amino]pyrimidin-4-yl]-4-(cyclopropylmethyl)pyrimidin-2-yl]amino]-2-methylpropan-2-ol Chemical compound N=1C(NCC(C)(O)C)=NC=C(C=2N=C(NC=3C=C(Cl)N=CC=3)N=CC=2)C=1CC1CC1 AWNXKZVIZARMME-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
INGWEZCOABYORO-UHFFFAOYSA-N 2-(furan-2-yl)-7-methyl-1h-1,8-naphthyridin-4-one Chemical compound N=1C2=NC(C)=CC=C2C(O)=CC=1C1=CC=CO1 INGWEZCOABYORO-UHFFFAOYSA-N 0.000 description 1
JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical group NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 description 1
LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
VHCSBTPOPKFYIU-UHFFFAOYSA-N 2-chloroethanesulfonyl chloride Chemical compound ClCCS(Cl)(=O)=O VHCSBTPOPKFYIU-UHFFFAOYSA-N 0.000 description 1
PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 1
UQIJIZARFFZEEN-UHFFFAOYSA-N CC1(C)C2=CC(S(O)(=O)=O)=CC=C2[N+](CCS(O)(=O)=O)=C1/C=C/C=C(\CCCCCCC(O)=O)/C=C/C=C(/C(C)(C)C1=C2)\N(CCS([O-])(=O)=O)C1=CC=C2S(O)(=O)=O Chemical compound CC1(C)C2=CC(S(O)(=O)=O)=CC=C2[N+](CCS(O)(=O)=O)=C1/C=C/C=C(\CCCCCCC(O)=O)/C=C/C=C(/C(C)(C)C1=C2)\N(CCS([O-])(=O)=O)C1=CC=C2S(O)(=O)=O UQIJIZARFFZEEN-UHFFFAOYSA-N 0.000 description 1
KIFKJRXYRIUYCV-UHFFFAOYSA-N CC1(C)C2=CC(S(O)(=O)=O)=CC=C2[N+](CCS(O)(=O)=O)=C1C=CC=C(CCC(O)=O)C=CC=C(C(C)(C)C1=C2)N(CCS([O-])(=O)=O)C1=CC=C2S(O)(=O)=O Chemical compound CC1(C)C2=CC(S(O)(=O)=O)=CC=C2[N+](CCS(O)(=O)=O)=C1C=CC=C(CCC(O)=O)C=CC=C(C(C)(C)C1=C2)N(CCS([O-])(=O)=O)C1=CC=C2S(O)(=O)=O KIFKJRXYRIUYCV-UHFFFAOYSA-N 0.000 description 1
FPBXQTVVZHZAGB-UHFFFAOYSA-N CC1(C)C2=CC(S(O)(=O)=O)=CC=C2[N+](CCS(O)(=O)=O)=C1C=CC=C(CCCCC(O)=O)C=CC=C(C(C)(C)C1=C2)N(CCS([O-])(=O)=O)C1=CC=C2S(O)(=O)=O Chemical compound CC1(C)C2=CC(S(O)(=O)=O)=CC=C2[N+](CCS(O)(=O)=O)=C1C=CC=C(CCCCC(O)=O)C=CC=C(C(C)(C)C1=C2)N(CCS([O-])(=O)=O)C1=CC=C2S(O)(=O)=O FPBXQTVVZHZAGB-UHFFFAOYSA-N 0.000 description 1
SJTXFTUKIJCAPU-UHFFFAOYSA-N CC1(C)C2=CC(S(O)(=O)=O)=CC=C2[N+](CCS(O)(=O)=O)=C1C=CC=C(CCCOCCC(O)=O)C=CC=C(C(C)(C)C1=C2)N(CCS([O-])(=O)=O)C1=CC=C2S(O)(=O)=O Chemical compound CC1(C)C2=CC(S(O)(=O)=O)=CC=C2[N+](CCS(O)(=O)=O)=C1C=CC=C(CCCOCCC(O)=O)C=CC=C(C(C)(C)C1=C2)N(CCS([O-])(=O)=O)C1=CC=C2S(O)(=O)=O SJTXFTUKIJCAPU-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699660 Mus musculus Species 0.000 description 1
108010064719 Oxyhemoglobins Proteins 0.000 description 1
VFKQWKQWRNVXTA-UHFFFAOYSA-N [3-(anilinomethylidene)-2-chlorocyclohexen-1-yl]methylidene-phenylazanium;chloride Chemical compound Cl.ClC1=C(C=NC=2C=CC=CC=2)CCCC1=CNC1=CC=CC=C1 VFKQWKQWRNVXTA-UHFFFAOYSA-N 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000007792 addition Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
125000000732 arylene group Chemical group 0.000 description 1
230000001588 bifunctional effect Effects 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
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239000006227 byproduct Substances 0.000 description 1
210000004899 c-terminal region Anatomy 0.000 description 1
239000000298 carbocyanine Substances 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
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238000004132 cross linking Methods 0.000 description 1
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YKFKEYKJGVSEIX-UHFFFAOYSA-N cyclohexanone, 4-(1,1-dimethylethyl)- Chemical compound CC(C)(C)C1CCC(=O)CC1 YKFKEYKJGVSEIX-UHFFFAOYSA-N 0.000 description 1
125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 1
150000001945 cysteines Chemical class 0.000 description 1
238000004163 cytometry Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000006735 deficit Effects 0.000 description 1
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230000001419 dependent effect Effects 0.000 description 1
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201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
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238000001035 drying Methods 0.000 description 1
238000001839 endoscopy Methods 0.000 description 1
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230000005284 excitation Effects 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000002073 fluorescence micrograph Methods 0.000 description 1
238000000799 fluorescence microscopy Methods 0.000 description 1
238000002189 fluorescence spectrum Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000003102 growth factor Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000005457 ice water Substances 0.000 description 1
MOFVSTNWEDAEEK-UHFFFAOYSA-M indocyanine green Chemical compound [Na+].[O-]S(=O)(=O)CCCCN1C2=CC=C3C=CC=CC3=C2C(C)(C)C1=CC=CC=CC=CC1=[N+](CCCCS([O-])(=O)=O)C2=CC=C(C=CC=C3)C3=C2C1(C)C MOFVSTNWEDAEEK-UHFFFAOYSA-M 0.000 description 1
229960004657 indocyanine green Drugs 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
230000001678 irradiating effect Effects 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
238000002372 labelling Methods 0.000 description 1
125000005647 linker group Chemical group 0.000 description 1
238000011068 loading method Methods 0.000 description 1
125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
238000009607 mammography Methods 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
238000011580 nude mouse model Methods 0.000 description 1
108010067933 oncofetal fibronectin Proteins 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
102000013415 peroxidase activity proteins Human genes 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
QWYZFXLSWMXLDM-UHFFFAOYSA-M pinacyanol iodide Chemical class [I-].C1=CC2=CC=CC=C2N(CC)C1=CC=CC1=CC=C(C=CC=C2)C2=[N+]1CC QWYZFXLSWMXLDM-UHFFFAOYSA-M 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
238000010188 recombinant method Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000009987 spinning Methods 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
208000001608 teratocarcinoma Diseases 0.000 description 1
SDLSMUZTXNXLFM-UHFFFAOYSA-N tert-butyl 2-(3-pyridin-4-ylpropoxy)acetate Chemical compound CC(C)(C)OC(=O)COCCCC1=CC=NC=C1 SDLSMUZTXNXLFM-UHFFFAOYSA-N 0.000 description 1
BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
LSTISIXQGSVYLB-UHFFFAOYSA-N tert-butyl 8-oxo-6-(2-oxoethyl)oct-6-enoate Chemical compound C(C)(C)(C)OC(=O)CCCCC(=CC=O)CC=O LSTISIXQGSVYLB-UHFFFAOYSA-N 0.000 description 1
RRVXZLSGEQVYGY-UHFFFAOYSA-N tert-butyl n-(1-aminohexyl)carbamate Chemical compound CCCCCC(N)NC(=O)OC(C)(C)C RRVXZLSGEQVYGY-UHFFFAOYSA-N 0.000 description 1
ZXUCBXRTRRIBSO-UHFFFAOYSA-L tetrabutylazanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC ZXUCBXRTRRIBSO-UHFFFAOYSA-L 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000006444 vascular growth Effects 0.000 description 1
230000007998 vessel formation Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0066—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid)
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
- C09B23/086—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines more than five >CH- groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

DE2003102787 2003-01-24 2003-01-24 Hydrophile, Thiol-reaktive Cyaninfarbstoffe und deren Konjugate mit Biomolekülen für die Fluoreszenzdiagnostik Ceased DE10302787A1 (de)

Priority Applications (23)

Application Number	Priority Date	Filing Date	Title
DE2003102787 DE10302787A1 (de)	2003-01-24	2003-01-24	Hydrophile, Thiol-reaktive Cyaninfarbstoffe und deren Konjugate mit Biomolekülen für die Fluoreszenzdiagnostik
AU2003292019A AU2003292019A1 (en)	2003-01-24	2003-11-14	Hydrophilic, thiol-reactive cyanine dyes and conjugates thereof with biomolecules for fluorescence diagnosis
BR0318028-0A BR0318028A (pt)	2003-01-24	2003-11-14	Corantes hidrofìlicos de cianina reativos a tiol e conjugados dos mesmos com biomoléculas para diagnóstico por fluorescência
PL03376459A PL376459A1 (en)	2003-01-24	2003-11-14	Hydrophilic, thiol-reactive cyanine dyes and conjugates thereof with biomolecules for fluorescence diagnosis
EA200501064A EA009386B1 (ru)	2003-01-24	2003-11-14	Гидрофильные, реакционные в отношении тиол-группы цианиновые красители, и их конъюгаты с биомолекулами для флюоресцентной диагностики
KR1020057013493A KR20050103907A (ko)	2003-01-24	2003-11-14	형광 진단을 위한 친수성의 티올-반응성 시아닌 염료 및그의 생체분자와의 접합체
MXPA05007668A MXPA05007668A (es)	2003-01-24	2003-11-14	Colorantes hidrofilicos de cianina, reactivos a tiol y conjugados de los mismos con biomoleculas para diagnostico por fluorescencia.
UAA200508207A UA82684C2 (uk)	2003-01-24	2003-11-14	Гідрофільні, реакційні відносно тіол-групи ціанінові барвники, спосіб їх одержання, їх кон'югати з біомолекулами, спосіб одержання останніх та їх застосування, а також діагностичний набір
YUP-2005/0561A RS20050561A (sr)	2003-01-24	2003-11-14	HIDROFILNE, TIOL-REAKTIVNE CIJANIN BOJE I NjIHOVI KONjUGATI SA BIOMOLEKULIMA ZA FLUORESCENTNU DIJAGNOZU
NZ541414A NZ541414A (en)	2003-01-24	2003-11-14	Indotricarbocyanine dyes and conjugates thereof with biomolecules for fluorescence diagnosis
CN 200380109197 CN1742057A (zh)	2003-01-24	2003-11-14	用于荧光诊断的亲水性硫醇反应性花青染料及其与生物分子的缀合物
AT03767544T ATE409209T1 (de)	2003-01-24	2003-11-14	Hydrophile, thiolreaktive cyaninfarbstoffe und deren konjugate mit biomolekülen für fluoreszenzdiagnose
JP2004566758A JP2006513293A (ja)	2003-01-24	2003-11-14	親水性チオール−反応性シアニン色素及び蛍光診断のための生物分子との接合体
EP03767544A EP1585791B1 (en)	2003-01-24	2003-11-14	Hydrophilic, thiol-reactive cyanine dyes and conjugates thereof with biomolecules for fluorescence diagnosis
CA002514131A CA2514131A1 (en)	2003-01-24	2003-11-14	Hydrophilic, thiol-reactive cyanine dyes and conjugates thereof with biomolecules for fluorescence diagnosis
ES03767544T ES2311736T3 (es)	2003-01-24	2003-11-14	Tintes hidrofilicos de cianina tiol reactivo y conjugados de los mismos con biomoleculas para el diagnostico por fluorescencia.
DE60323766T DE60323766D1 (de)	2003-01-24	2003-11-14	En konjugate mit biomolekülen für fluoreszenzdiagnose
PCT/EP2003/012735 WO2004065491A1 (en)	2003-01-24	2003-11-14	Hydrophilic, thiol-reactive cyanine dyes and conjugates thereof with biomolecules for fluorescence diagnosis
US10/762,582 US20040260072A1 (en)	2003-01-24	2004-01-23	Hydrophilic, thiol-reactive cyanine dyes and conjugates thereof with biomolecules for fluorescence diagnosis
CR7925A CR7925A (es)	2003-01-24	2005-07-28	Tinturas de cianina hidrofilicas, reactivas con tiol y conjugados de las mismas con biomoleculas para diagnostico por fluorescencia
ZA200506759A ZA200506759B (en)	2003-01-24	2005-08-23	Hydrophilic, thiol-reactive cyanine dyes and conjugates thereof with biomolecules for fluorescence diagnosis
EC2005005975A ECSP055975A (es)	2003-01-24	2005-08-23	Tinturas de cianina hidrofílicas, reactivas con tiol y conjugados de las mismas con biomoléculas para diagnóstico por fluorescencia
NO20053919A NO20053919L (no)	2003-01-24	2005-08-23	Hydrofile tiol-reaktive cyaninfargestoffer og konjugater av disse med biomolekyler for fluorisensdiagnostikk.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2003102787 DE10302787A1 (de)	2003-01-24	2003-01-24	Hydrophile, Thiol-reaktive Cyaninfarbstoffe und deren Konjugate mit Biomolekülen für die Fluoreszenzdiagnostik

Publications (1)

Publication Number	Publication Date
DE10302787A1 true DE10302787A1 (de)	2004-08-12

Family

ID=32694952

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE2003102787 Ceased DE10302787A1 (de)	2003-01-24	2003-01-24	Hydrophile, Thiol-reaktive Cyaninfarbstoffe und deren Konjugate mit Biomolekülen für die Fluoreszenzdiagnostik

Country Status (6)

Country	Link
CN (1)	CN1742057A (uk)
DE (1)	DE10302787A1 (uk)
NO (1)	NO20053919L (uk)
RS (1)	RS20050561A (uk)
UA (1)	UA82684C2 (uk)
ZA (1)	ZA200506759B (uk)

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EP3001197A1 (en) *	2014-09-23	2016-03-30	Universität Heidelberg	Fluorescent protein stains

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NZ597512A (en) *	2009-07-16	2014-03-28	Beckman Coulter Inc	Novel fluorescent dyes and uses thereof
CN107488657A (zh) *	2017-08-15	2017-12-19	苏州泽科生物科技有限公司	核酸的活性染料偶联标记、检测及提纯方法
US10968386B2 (en)	2018-01-09	2021-04-06	Shenzhen University	Pentamethine cyanine dye and preparation method therefor
CN108192376A (zh) *	2018-01-09	2018-06-22	深圳大学	一种五甲川菁染料及制备方法
CN108727245B (zh) *	2018-07-02	2021-09-28	广州中医药大学(广州中医药研究院)	一种水杨酸类化合物及其制备方法和应用
CN110201189B (zh) *	2019-06-03	2021-12-07	沈阳药科大学	白蛋白结合型近红外荧光染料-马来酰亚胺共轭物

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2003
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- 2003-11-14 UA UAA200508207A patent/UA82684C2/uk unknown
- 2003-11-14 RS YUP-2005/0561A patent/RS20050561A/sr unknown
2005
- 2005-08-23 ZA ZA200506759A patent/ZA200506759B/en unknown
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Also Published As

Publication number	Publication date
ZA200506759B (en)	2007-01-31
CN1742057A (zh)	2006-03-01
NO20053919L (no)	2005-10-24
UA82684C2 (uk)	2008-05-12
RS20050561A (sr)	2007-09-21
NO20053919D0 (no)	2005-08-23

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2004-08-12	OP8	Request for examination as to paragraph 44 patent law
2007-05-31	8127	New person/name/address of the applicant	Owner name: BAYER SCHERING PHARMA AG, 13353 BERLIN, DE
2008-03-27	8127	New person/name/address of the applicant	Owner name: BAYER SCHERING PHARMA AKIENGESELLSCHAFT, 13353, DE
2009-06-04	8131	Rejection