DE19645974C1 - (Z)-5-[[3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinyl]methylen]-2-thioxo-4- thiazolidinon, Verfahren zu dessen Herstellung und Verwendung - Google Patents
(Z)-5-[[3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinyl]methylen]-2-thioxo-4- thiazolidinon, Verfahren zu dessen Herstellung und VerwendungInfo
- Publication number
- DE19645974C1 DE19645974C1 DE19645974A DE19645974A DE19645974C1 DE 19645974 C1 DE19645974 C1 DE 19645974C1 DE 19645974 A DE19645974 A DE 19645974A DE 19645974 A DE19645974 A DE 19645974A DE 19645974 C1 DE19645974 C1 DE 19645974C1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- thiazolidinone
- thioxo
- phosphonooxy
- pyridinyl
- Prior art date
- 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 - Fee Related
Links
- WJDPAGLWZIPYMX-WAPJZHGLSA-N [5-hydroxy-6-methyl-4-[(z)-(4-oxo-2-sulfanylidene-1,3-thiazolidin-5-ylidene)methyl]pyridin-3-yl]methyl dihydrogen phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(\C=C/2C(NC(=S)S\2)=O)=C1O WJDPAGLWZIPYMX-WAPJZHGLSA-N 0.000 title claims description 3
- 238000000034 method Methods 0.000 title description 2
- 108020004414 DNA Proteins 0.000 claims description 10
- 102000053602 DNA Human genes 0.000 claims description 9
- 108020004682 Single-Stranded DNA Proteins 0.000 claims description 8
- 108020004707 nucleic acids Proteins 0.000 claims description 8
- 102000039446 nucleic acids Human genes 0.000 claims description 8
- 150000007523 nucleic acids Chemical class 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000001514 detection method Methods 0.000 claims description 4
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical compound O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 238000004458 analytical method Methods 0.000 claims description 3
- NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 claims description 3
- 235000007682 pyridoxal 5'-phosphate Nutrition 0.000 claims description 3
- 239000011589 pyridoxal 5'-phosphate Substances 0.000 claims description 3
- 238000006000 Knoevenagel condensation reaction Methods 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 244000052769 pathogen Species 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 239000008139 complexing agent Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 229940126214 compound 3 Drugs 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000027455 binding Effects 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- CEEQUQSGVRRXQI-UHFFFAOYSA-N Pyridoxal 5-phosphate monohydrate Chemical compound O.CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O CEEQUQSGVRRXQI-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DTQVDTLACAAQTR-DYCDLGHISA-N trifluoroacetic acid-d1 Chemical compound [2H]OC(=O)C(F)(F)F DTQVDTLACAAQTR-DYCDLGHISA-N 0.000 description 3
- RBCOYOYDYNXAFA-UHFFFAOYSA-L (5-hydroxy-4,6-dimethylpyridin-3-yl)methyl phosphate Chemical compound CC1=NC=C(COP([O-])([O-])=O)C(C)=C1O RBCOYOYDYNXAFA-UHFFFAOYSA-L 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000005515 coenzyme Substances 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000010265 fast atom bombardment Methods 0.000 description 2
- 238000001917 fluorescence detection Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- XRCNLLJRVWMRCX-UHFFFAOYSA-N 2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound O=C1CSC(=S)N1.O=C1CSC(=S)N1 XRCNLLJRVWMRCX-UHFFFAOYSA-N 0.000 description 1
- NOIIUHRQUVNIDD-UHFFFAOYSA-N 3-[[oxo(pyridin-4-yl)methyl]hydrazo]-N-(phenylmethyl)propanamide Chemical compound C=1C=CC=CC=1CNC(=O)CCNNC(=O)C1=CC=NC=C1 NOIIUHRQUVNIDD-UHFFFAOYSA-N 0.000 description 1
- 238000004679 31P NMR spectroscopy Methods 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 230000004568 DNA-binding Effects 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 206010015137 Eructation Diseases 0.000 description 1
- 241000700721 Hepatitis B virus Species 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 206010029098 Neoplasm skin Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 208000027687 belching Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000012678 infectious agent Substances 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- -1 pyridoxylidene rhodanine Chemical compound 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000009419 refurbishment Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical group CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Polyesters Or Polycarbonates (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19645974A DE19645974C1 (de) | 1996-11-07 | 1996-11-07 | (Z)-5-[[3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinyl]methylen]-2-thioxo-4- thiazolidinon, Verfahren zu dessen Herstellung und Verwendung |
| NZ335977A NZ335977A (en) | 1996-11-07 | 1997-11-07 | Pyridine derivatives which are knoevenagel condensation products |
| AU54798/98A AU728345B2 (en) | 1996-11-07 | 1997-11-07 | New knoevenagel condensation products, method for their production and their use |
| PCT/EP1997/006184 WO1998020013A1 (fr) | 1996-11-07 | 1997-11-07 | Nouveaux produits de condensation de knoevenagel, leur procede de production et leur utilisation |
| CA002270973A CA2270973A1 (fr) | 1996-11-07 | 1997-11-07 | Nouveaux produits de condensation de knoevenagel, leur procede de production et leur utilisation |
| CZ991609A CZ160999A3 (cs) | 1996-11-07 | 1997-11-07 | Nové Knoevenagelovy kondenzační produkty, způsoby jejich výroby a jejich použití |
| SK617-99A SK61799A3 (en) | 1996-11-07 | 1997-11-07 | New knoevenagel condensation products, method for their production and their use |
| CN97199496A CN1236369A (zh) | 1996-11-07 | 1997-11-07 | 新的诺文葛耳缩合反应产物,其制备方法及应用 |
| PL97333128A PL333128A1 (en) | 1996-11-07 | 1997-11-07 | New products of knoevenagel's condensation, method of manufacturing of them and their applications |
| HU9904289A HUP9904289A3 (en) | 1996-11-07 | 1997-11-07 | Pyridines substituted by heterocyclic groups, method for their production and pharmaceutical compositions containing the same |
| EP97951145A EP0937089A1 (fr) | 1996-11-07 | 1997-11-07 | Nouveaux produits de condensation de knoevenagel, leur procede de production et leur utilisation |
| IL12982697A IL129826A0 (en) | 1996-11-07 | 1997-11-07 | New knoevenagel condensation products method for their production and their use |
| JP52107198A JP2001503752A (ja) | 1996-11-07 | 1997-11-07 | 新規クネベナゲル縮合生成物、その製法及びその使用 |
| KR1019990704073A KR20000053141A (ko) | 1996-11-07 | 1997-11-07 | 신규한 크노에베나겔 축합 생성물, 이의 제조 방법 및 이의 용도 |
| BRPI9712930-5A BR9712930A (pt) | 1996-11-07 | 1997-11-07 | produtos de condensação de knoevenagel, processos para a sua preparação e aplicação |
| TR1999/01733T TR199901733T2 (xx) | 1996-11-07 | 1997-11-07 | Yeni knoevenagel kondansasyon �r�nleri, bunlar�n �retim y�ntemi ve kullan�m�. |
| DE19819820A DE19819820A1 (de) | 1996-11-07 | 1998-05-04 | Neue monomere, oligomere und polymere Kondensationsprodukte biologischer Komponenten, Verfahren zu deren Herstellung und Verwendung |
| NO992209A NO992209L (no) | 1996-11-07 | 1999-05-06 | Nye Knoevenagel-kondensasjonsprodukter, fremgangsmÕte for deres fremstilling samt anvendelse derav |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19645974A DE19645974C1 (de) | 1996-11-07 | 1996-11-07 | (Z)-5-[[3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinyl]methylen]-2-thioxo-4- thiazolidinon, Verfahren zu dessen Herstellung und Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19645974C1 true DE19645974C1 (de) | 1998-08-13 |
Family
ID=7810958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19645974A Expired - Fee Related DE19645974C1 (de) | 1996-11-07 | 1996-11-07 | (Z)-5-[[3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinyl]methylen]-2-thioxo-4- thiazolidinon, Verfahren zu dessen Herstellung und Verwendung |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0937089A1 (fr) |
| JP (1) | JP2001503752A (fr) |
| KR (1) | KR20000053141A (fr) |
| CN (1) | CN1236369A (fr) |
| AU (1) | AU728345B2 (fr) |
| BR (1) | BR9712930A (fr) |
| CA (1) | CA2270973A1 (fr) |
| CZ (1) | CZ160999A3 (fr) |
| DE (1) | DE19645974C1 (fr) |
| HU (1) | HUP9904289A3 (fr) |
| IL (1) | IL129826A0 (fr) |
| NO (1) | NO992209L (fr) |
| NZ (1) | NZ335977A (fr) |
| PL (1) | PL333128A1 (fr) |
| SK (1) | SK61799A3 (fr) |
| TR (1) | TR199901733T2 (fr) |
| WO (1) | WO1998020013A1 (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999057124A1 (fr) * | 1998-05-04 | 1999-11-11 | Andreas Johannes Kesel | Condensats knoevenagel monomeres, oligomeres et polymeres |
| CN1325309A (zh) * | 1998-08-21 | 2001-12-05 | 维洛药品公司 | 用于治疗或预防病毒感染和相关疾病的化合物、组合物和方法 |
| RU2001132323A (ru) * | 1999-04-30 | 2004-02-20 | Вальтер ОБЕРТЮР (DE) | Антиокислительные аналоги витамина B6 |
| US6940497B2 (en) * | 2001-10-16 | 2005-09-06 | Hewlett-Packard Development Company, L.P. | Portable electronic reading apparatus |
| US20030071780A1 (en) * | 2001-10-16 | 2003-04-17 | Vincent Kent D. | High resolution display |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9103776D0 (sv) * | 1991-12-19 | 1991-12-19 | Astra Ab | New compounds |
| IT1266570B1 (it) * | 1993-07-30 | 1997-01-09 | Zambon Spa | Derivati della propanammide n-eteroaril sostituiti utili nel trattamento delle malattie cardiovascolari |
| FR2722790B1 (fr) * | 1994-07-19 | 1996-10-04 | Roussel Uclaf | Nouvelles cephalosporines comportant en position 7 un radical benzyloxymino subtitue, leur procede de preparation leur application comme medicaments |
-
1996
- 1996-11-07 DE DE19645974A patent/DE19645974C1/de not_active Expired - Fee Related
-
1997
- 1997-11-07 CA CA002270973A patent/CA2270973A1/fr not_active Withdrawn
- 1997-11-07 EP EP97951145A patent/EP0937089A1/fr not_active Withdrawn
- 1997-11-07 AU AU54798/98A patent/AU728345B2/en not_active Revoked
- 1997-11-07 BR BRPI9712930-5A patent/BR9712930A/pt not_active IP Right Cessation
- 1997-11-07 JP JP52107198A patent/JP2001503752A/ja active Pending
- 1997-11-07 CZ CZ991609A patent/CZ160999A3/cs unknown
- 1997-11-07 IL IL12982697A patent/IL129826A0/xx unknown
- 1997-11-07 KR KR1019990704073A patent/KR20000053141A/ko not_active Application Discontinuation
- 1997-11-07 TR TR1999/01733T patent/TR199901733T2/xx unknown
- 1997-11-07 WO PCT/EP1997/006184 patent/WO1998020013A1/fr not_active Application Discontinuation
- 1997-11-07 HU HU9904289A patent/HUP9904289A3/hu unknown
- 1997-11-07 NZ NZ335977A patent/NZ335977A/xx unknown
- 1997-11-07 SK SK617-99A patent/SK61799A3/sk unknown
- 1997-11-07 CN CN97199496A patent/CN1236369A/zh active Pending
- 1997-11-07 PL PL97333128A patent/PL333128A1/xx unknown
-
1999
- 1999-05-06 NO NO992209A patent/NO992209L/no not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| Tetrahedron (1996), 52(47), 14787-14800 * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU728345B2 (en) | 2001-01-04 |
| HUP9904289A3 (en) | 2001-08-28 |
| NZ335977A (en) | 2000-12-22 |
| NO992209D0 (no) | 1999-05-06 |
| BR9712930A (pt) | 2006-04-18 |
| IL129826A0 (en) | 2000-02-29 |
| CA2270973A1 (fr) | 1998-05-14 |
| EP0937089A1 (fr) | 1999-08-25 |
| AU5479898A (en) | 1998-05-29 |
| SK61799A3 (en) | 2000-01-18 |
| CN1236369A (zh) | 1999-11-24 |
| KR20000053141A (ko) | 2000-08-25 |
| JP2001503752A (ja) | 2001-03-21 |
| TR199901733T2 (xx) | 1999-09-21 |
| PL333128A1 (en) | 1999-11-22 |
| NO992209L (no) | 1999-07-01 |
| HUP9904289A2 (hu) | 2001-04-28 |
| CZ160999A3 (cs) | 1999-09-15 |
| WO1998020013A1 (fr) | 1998-05-14 |
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