CS272225B2 - Method of new pyrimidine derivatives production - Google Patents
Method of new pyrimidine derivatives production Download PDFInfo
- Publication number
- CS272225B2 CS272225B2 CS875834A CS583487A CS272225B2 CS 272225 B2 CS272225 B2 CS 272225B2 CS 875834 A CS875834 A CS 875834A CS 583487 A CS583487 A CS 583487A CS 272225 B2 CS272225 B2 CS 272225B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- dideoxy
- ethyluridine
- ethyl
- uridine
- acetamido
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 4
- 150000003230 pyrimidines Chemical class 0.000 title description 4
- -1 2,4-dichloro-phenoxy Chemical group 0.000 claims description 62
- 150000001875 compounds Chemical class 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims description 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 claims 24
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 claims 12
- DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 claims 12
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 claims 12
- 229940045145 uridine Drugs 0.000 claims 12
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 claims 6
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 6
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 claims 6
- 229940104230 thymidine Drugs 0.000 claims 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 4
- 229940080818 propionamide Drugs 0.000 claims 4
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- NDPWPXGWGDIEJL-VPCXQMTMSA-N 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-ethylpyrimidine-2,4-dione Chemical compound C(C)C=1C(NC(N([C@H]2[C@H](O)[C@H](O)[C@@H](C)O2)C=1)=O)=O NDPWPXGWGDIEJL-VPCXQMTMSA-N 0.000 claims 1
- CRYOBSXYQNJFNR-UHFFFAOYSA-N 2-(2,6-dimethylphenyl)acetamide Chemical compound CC1=CC=CC(C)=C1CC(N)=O CRYOBSXYQNJFNR-UHFFFAOYSA-N 0.000 claims 1
- QHOOQLXZKWMYCC-UHFFFAOYSA-N 2-(2-methoxyphenyl)acetamide Chemical compound COC1=CC=CC=C1CC(N)=O QHOOQLXZKWMYCC-UHFFFAOYSA-N 0.000 claims 1
- HLGMJBADUQKGAW-RRFJBIMHSA-N 2-bromo-n-[[(2r,3s,5r)-5-(5-ethyl-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl]benzamide Chemical compound O=C1NC(=O)C(CC)=CN1[C@@H]1O[C@H](CNC(=O)C=2C(=CC=CC=2)Br)[C@@H](O)C1 HLGMJBADUQKGAW-RRFJBIMHSA-N 0.000 claims 1
- TVLXILQUDKDOIC-BFHYXJOUSA-N n-[[(2r,3s,5r)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl]benzamide Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CNC(=O)C=2C=CC=CC=2)[C@@H](O)C1 TVLXILQUDKDOIC-BFHYXJOUSA-N 0.000 claims 1
- ZJDOZXNSYQLVDI-QZNHQXDQSA-N n-[[(2r,3s,5r)-5-(5-ethyl-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl]-2-(4-phenylphenyl)acetamide Chemical compound O=C1NC(=O)C(CC)=CN1[C@@H]1O[C@H](CNC(=O)CC=2C=CC(=CC=2)C=2C=CC=CC=2)[C@@H](O)C1 ZJDOZXNSYQLVDI-QZNHQXDQSA-N 0.000 claims 1
- YBIPXNGIZQPUCU-RRFJBIMHSA-N n-[[(2r,3s,5r)-5-(5-ethyl-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl]benzamide Chemical compound O=C1NC(=O)C(CC)=CN1[C@@H]1O[C@H](CNC(=O)C=2C=CC=CC=2)[C@@H](O)C1 YBIPXNGIZQPUCU-RRFJBIMHSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 229910052731 fluorine Chemical group 0.000 description 2
- 239000011737 fluorine Chemical group 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- MLMQPDHYNJCQAO-UHFFFAOYSA-N 3,3-dimethylbutyric acid Chemical compound CC(C)(C)CC(O)=O MLMQPDHYNJCQAO-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- DNVJGJUGFFYUPT-UHFFFAOYSA-N 9h-fluorene-9-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)C3=CC=CC=C3C2=C1 DNVJGJUGFFYUPT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 108010011222 cyclo(Arg-Pro) Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB868620070A GB8620070D0 (en) | 1986-08-18 | 1986-08-18 | Pyrimidine derivatives |
| GB878711336A GB8711336D0 (en) | 1986-08-18 | 1987-05-14 | Pyrimidine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS583487A2 CS583487A2 (en) | 1990-03-14 |
| CS272225B2 true CS272225B2 (en) | 1991-01-15 |
Family
ID=26291195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS875834A CS272225B2 (en) | 1986-08-18 | 1987-08-05 | Method of new pyrimidine derivatives production |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US4851519A (pt) |
| EP (1) | EP0257378B1 (pt) |
| JP (1) | JPH0794453B2 (pt) |
| CN (1) | CN1020106C (pt) |
| AU (1) | AU602909B2 (pt) |
| CA (1) | CA1303031C (pt) |
| CS (1) | CS272225B2 (pt) |
| DE (1) | DE3771146D1 (pt) |
| DK (1) | DK375787A (pt) |
| ES (1) | ES2040715T3 (pt) |
| FI (1) | FI86639C (pt) |
| GR (1) | GR3002636T3 (pt) |
| HU (1) | HU199500B (pt) |
| IE (1) | IE61061B1 (pt) |
| IL (1) | IL83509A (pt) |
| MC (1) | MC1846A1 (pt) |
| MX (1) | MX174238B (pt) |
| NO (1) | NO170884C (pt) |
| NZ (1) | NZ221412A (pt) |
| PH (1) | PH24653A (pt) |
| PT (1) | PT85551B (pt) |
| ZW (1) | ZW14187A1 (pt) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK163128C (da) * | 1986-08-12 | 1992-06-15 | Hoffmann La Roche | Pyrimidinnucleosider, fremgangsmaade til fremstilling deraf, farmaceutiske praeparater indeholdende pyrimidinnucleosiderne og anvendelse af pyrimidinnucleosiderne |
| NO170884C (no) * | 1986-08-18 | 1992-12-23 | Hoffmann La Roche | Analogifremgangsmaate ved fremstilling av terapeutisk aktive pyrimidinderivater |
| US5312961A (en) * | 1989-02-14 | 1994-05-17 | Elf Sanofi | 2-amino-7-hydroxytetralin carboxylalkyl ethers |
| US5652335A (en) * | 1990-02-28 | 1997-07-29 | Teikoku Seiyaku Kabushiki Kaisha | Physiologically active substance well capable of permeating biomembrane |
| DE69120397T2 (de) * | 1990-02-28 | 1996-11-07 | Teikoku Seiyaku Kk | Physiologisch aktive substanzen, die gut zum durchdringen biologischer membranen befähigt sind |
| US5306722A (en) * | 1992-09-02 | 1994-04-26 | Bristol-Myers Squibb Company | Thymidine derivatives and therapeutic method of use |
| US6040298A (en) * | 1992-12-23 | 2000-03-21 | Oclassen Pharmaceuticals, Inc. | Methods for treatment with compositions effective against acyclovir-resistant strains of herpes viruses |
| GB9606264D0 (en) * | 1995-07-13 | 1996-05-29 | Hoffmann La Roche | Pyrimidine nucleoside derivatives |
| GB9514268D0 (en) * | 1995-07-13 | 1995-09-13 | Hoffmann La Roche | Pyrimidine nucleoside |
| GB9608199D0 (en) * | 1995-08-04 | 1996-06-26 | Hoffmann La Roche | Pyrimide nucleoside derivatives |
| US5783689A (en) * | 1996-11-12 | 1998-07-21 | University Of Notre Dame | Antibacterial and antifungal nucleosides |
| CA2579756C (en) * | 2004-06-19 | 2013-04-30 | Human Biomolecular Research Institute | Modulators of central nervous system neurotransmitters |
| JP5205873B2 (ja) * | 2006-09-12 | 2013-06-05 | 和光純薬工業株式会社 | 新規なジデオキシヌクレオシド誘導体 |
| US7629447B2 (en) * | 2006-09-12 | 2009-12-08 | Wako Pure Chemical Industries, Ltd. | Dideoxynucleoside derivatives |
| EP3165234B1 (de) * | 2009-07-31 | 2019-04-03 | ethris GmbH | Rna mit einer kombination aus unmodifizierten und modifizierten nucleotiden zur proteinexpression |
| DE102013225402A1 (de) | 2013-12-10 | 2015-06-11 | BSH Hausgeräte GmbH | Haushaltsgerät mit einer in einem Stauraum versenkbaren Tür und verschiebbarer Drehachse einer Lagereinheit sowie Verfahren zum öffnen und Schließen einer derartigen Tür |
| DE102013225403A1 (de) | 2013-12-10 | 2015-06-11 | BSH Hausgeräte GmbH | Haushaltsgerät mit einer in einem Verstauraum versenkbaren Tür mit vertikaler Lageveränderungsmöglichkeit einer Drehachse einer Lagereinheit sowie Verfahren zum öffnen und Schließen einer Tür |
| DE102013225401A1 (de) | 2013-12-10 | 2015-06-11 | BSH Hausgeräte GmbH | Haushaltsgerät mit einer in einen Verstauraum einfahrbaren Tür und Verfahren zum öffnen und Schließen einer Tür eines Haushaltsgeräts |
| DE102015206577B4 (de) | 2015-04-13 | 2025-01-16 | BSH Hausgeräte GmbH | Haushaltsgerät mit einer in einem Verstauraum versenkbaren Tür mit elliptischer Kulisse zur Bewegung eines Lagerbügels einer Tür-Lagereinheit |
| DE102015206576A1 (de) | 2015-04-13 | 2016-10-13 | BSH Hausgeräte GmbH | Haushaltsgerät mit einer in einem Verstauraum versenkbaren Tür mit spezifischer Lagereinheit |
| MX389242B (es) | 2015-06-15 | 2025-03-20 | Nmd Pharma As | Compuestos para su uso en el tratamiento de trastornos neuromusculares |
| US12440477B2 (en) | 2017-12-14 | 2025-10-14 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
| US11730714B2 (en) | 2017-12-14 | 2023-08-22 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
| US10385028B2 (en) | 2017-12-14 | 2019-08-20 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
| US11147788B2 (en) | 2017-12-14 | 2021-10-19 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
| DE102018201949A1 (de) | 2018-02-08 | 2019-08-08 | BSH Hausgeräte GmbH | Gargerät mit einer in einen Verstauraum versenkbaren Tür mit einem spezifischen Koppelmodul, sowie Verfahren zum Bewegen einer Tür |
| DE102018201950A1 (de) | 2018-02-08 | 2019-08-08 | BSH Hausgeräte GmbH | Gargerät mit einem Technikteil für eine versenkbare Tür, welches eine Führungsbahn in einer oberen Höhenhälfte des Technikteils aufweist |
| WO2025149479A1 (en) * | 2024-01-12 | 2025-07-17 | Roche Diagnostics Gmbh | Synthesis of modified nucleoside triphosphates |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4128639A (en) * | 1977-12-14 | 1978-12-05 | Research Corporation | Nitrosourea analogs of thymidine |
| US4211773A (en) * | 1978-10-02 | 1980-07-08 | Sloan Kettering Institute For Cancer Research | 5-Substituted 1-(2'-Deoxy-2'-substituted-β-D-arabinofuranosyl)pyrimidine nucleosides |
| DE3045375A1 (de) * | 1980-12-02 | 1982-07-01 | Robugen Gmbh Pharmazeutische Fabrik Esslingen A.N., 7300 Esslingen | Neue substituierte pyrimidin-nukleoside mit antiviraler wirkung, verfahren zu deren herstellung und daraus zubereitete arzneiformen |
| DE3045342A1 (de) * | 1980-12-02 | 1982-07-01 | Robugen Gmbh Pharmazeutische Fabrik Esslingen A.N., 7300 Esslingen | Neue substituierte pyrimidin-nukleoside mit antiviraler und cytostatischer wirkung, verfahren zu deren herstellung und daraus bereitete arzneiformen |
| US4762823A (en) * | 1985-10-16 | 1988-08-09 | Sloan-Kettering Institute For Cancer Research | Nucleosides of 5-monofluoromethyluracil and 5-difluoromethyluracil |
| DK363987A (da) * | 1986-08-08 | 1988-02-09 | Hoffmann La Roche | Pyrimidinderivater |
| DK163128C (da) * | 1986-08-12 | 1992-06-15 | Hoffmann La Roche | Pyrimidinnucleosider, fremgangsmaade til fremstilling deraf, farmaceutiske praeparater indeholdende pyrimidinnucleosiderne og anvendelse af pyrimidinnucleosiderne |
| NO170884C (no) * | 1986-08-18 | 1992-12-23 | Hoffmann La Roche | Analogifremgangsmaate ved fremstilling av terapeutisk aktive pyrimidinderivater |
-
1987
- 1987-07-15 NO NO872961A patent/NO170884C/no unknown
- 1987-07-17 DK DK375787A patent/DK375787A/da not_active Application Discontinuation
- 1987-07-31 US US07/080,021 patent/US4851519A/en not_active Expired - Lifetime
- 1987-08-03 ZW ZW141/87A patent/ZW14187A1/xx unknown
- 1987-08-04 ES ES198787111280T patent/ES2040715T3/es not_active Expired - Lifetime
- 1987-08-04 DE DE8787111280T patent/DE3771146D1/de not_active Expired - Lifetime
- 1987-08-04 EP EP87111280A patent/EP0257378B1/de not_active Expired - Lifetime
- 1987-08-05 CS CS875834A patent/CS272225B2/cs unknown
- 1987-08-07 CA CA000543985A patent/CA1303031C/en not_active Expired - Lifetime
- 1987-08-11 NZ NZ221412A patent/NZ221412A/en unknown
- 1987-08-12 IL IL8350987A patent/IL83509A/en not_active IP Right Cessation
- 1987-08-13 MC MC871907A patent/MC1846A1/fr unknown
- 1987-08-13 AU AU76841/87A patent/AU602909B2/en not_active Ceased
- 1987-08-14 PH PH35679A patent/PH24653A/en unknown
- 1987-08-17 FI FI873555A patent/FI86639C/fi not_active IP Right Cessation
- 1987-08-17 MX MX776987A patent/MX174238B/es unknown
- 1987-08-17 JP JP62203963A patent/JPH0794453B2/ja not_active Expired - Fee Related
- 1987-08-17 HU HU873687A patent/HU199500B/hu not_active IP Right Cessation
- 1987-08-17 CN CN87105758A patent/CN1020106C/zh not_active Expired - Fee Related
- 1987-08-17 IE IE219187A patent/IE61061B1/en not_active IP Right Cessation
- 1987-08-18 PT PT85551A patent/PT85551B/pt not_active IP Right Cessation
-
1989
- 1989-04-24 US US07/342,277 patent/US5010060A/en not_active Expired - Fee Related
-
1991
- 1991-08-30 GR GR91401256T patent/GR3002636T3/el unknown
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